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  Subjects -> ALTERNATIVE MEDICINE (Total: 111 journals)
Showing 1 - 15 of 15 Journals sorted alphabetically
Acupuncture & Electro-Therapeutics Research     Full-text available via subscription   (Followers: 8)
Acupuncture and Related Therapies     Hybrid Journal   (Followers: 10)
Acupuncture in Medicine     Hybrid Journal   (Followers: 19)
Advanced Herbal Medicine     Open Access   (Followers: 8)
Advances in Traditional Medicine     Hybrid Journal   (Followers: 8)
African Journal of Traditional, Complementary and Alternative Medicines     Open Access   (Followers: 7)
Akupunktur & Aurikulomedizin     Full-text available via subscription   (Followers: 1)
Allgemeine Homöopathische Zeitung     Hybrid Journal   (Followers: 3)
Alternative & Integrative Medicine     Open Access   (Followers: 16)
Alternative and Complementary Therapies     Hybrid Journal   (Followers: 22)
Alternative Medicine     Full-text available via subscription   (Followers: 4)
Alternative Medicine Studies     Open Access   (Followers: 14)
Anales de Hidrología Médica     Open Access   (Followers: 2)
Ancient Science of Life     Open Access   (Followers: 6)
Arabian Journal of Medicinal and Aromatic Plants     Open Access   (Followers: 4)
Arteterapia. Papeles de arteterapia y educación artística para la inclusión social     Open Access   (Followers: 5)
Asian Journal of Plant Pathology     Open Access   (Followers: 4)
Australian Journal of Acupuncture and Chinese Medicine     Full-text available via subscription   (Followers: 4)
Australian Journal of Herbal Medicine     Full-text available via subscription   (Followers: 5)
Australian Journal of Music Therapy     Full-text available via subscription   (Followers: 11)
Avicenna Journal of Phytomedicine     Open Access   (Followers: 1)
AYU : An international quarterly journal of research in Ayurveda     Open Access   (Followers: 6)
BMC Complementary and Alternative Medicine     Open Access   (Followers: 23)
Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas     Open Access   (Followers: 2)
Botanics : Targets and Therapy     Open Access   (Followers: 6)
Cadernos de Naturologia e Terapias Complementares     Open Access   (Followers: 1)
Chinese Herbal Medicines     Full-text available via subscription   (Followers: 1)
Chinese Medicine     Open Access   (Followers: 5)
Cognitive Neuroscience     Hybrid Journal   (Followers: 31)
Complementary Therapies in Clinical Practice     Hybrid Journal   (Followers: 23)
Complementary Therapies in Medicine     Hybrid Journal   (Followers: 19)
Current Traditional Medicine     Hybrid Journal   (Followers: 5)
Deutsche Heilpraktiker-Zeitschrift     Hybrid Journal   (Followers: 3)
Deutsche Zeitschrift für Akupunktur     Full-text available via subscription   (Followers: 2)
Erfahrungsheilkunde     Hybrid Journal   (Followers: 1)
European Journal of Medicinal Plants     Open Access  
Evidence-based Complementary and Alternative Medicine     Open Access   (Followers: 30)
Experimental and Therapeutic Medicine     Full-text available via subscription   (Followers: 1)
Fitoterapia     Hybrid Journal   (Followers: 9)
Focus on Alternative and Complementary Therapies     Hybrid Journal   (Followers: 12)
Global Journal of Integrated Chinese Medicine and Western Medicine     Open Access   (Followers: 1)
Global Journal of Traditional Medicine     Open Access   (Followers: 2)
Herba Polonica     Open Access   (Followers: 1)
Herbal Medicines Journal     Open Access   (Followers: 1)
Indian Journal of Research in Homoeopathy     Open Access   (Followers: 2)
Indian Journal of Traditional Knowledge (IJTK)     Open Access   (Followers: 2)
Innovare Journal of Ayurvedic Sciences     Open Access   (Followers: 10)
Intas Polivet     Full-text available via subscription   (Followers: 5)
Integrative Medicine Research     Open Access   (Followers: 3)
International Journal of Health and Medicine     Open Access   (Followers: 1)
International Journal of High Dilution Research     Open Access  
International Journal of Qualitative Studies on Health and Well-Being     Open Access   (Followers: 22)
International Journal of Yoga     Open Access   (Followers: 17)
International Journal of Yoga : Philosophy, Psychology and Parapsychology     Open Access   (Followers: 7)
Ipnosi     Full-text available via subscription  
Journal of Acupuncture and Herbs     Open Access   (Followers: 3)
Journal of Acupuncture and Meridian Studies     Open Access   (Followers: 1)
Journal of Acupuncture and Tuina Science     Hybrid Journal   (Followers: 4)
Journal of Alternative and Complementary Medicine     Hybrid Journal   (Followers: 17)
Journal of Applied Arts and Health     Hybrid Journal   (Followers: 1)
Journal of Applied Research on Medicinal and Aromatic Plants     Hybrid Journal   (Followers: 1)
Journal of Asian Natural Products Research     Hybrid Journal   (Followers: 5)
Journal of Ayurveda and Integrative Medicine     Open Access   (Followers: 7)
Journal of AYUSH :- Ayurveda, Yoga, Unani, Siddha and Homeopathy     Full-text available via subscription   (Followers: 10)
Journal of Bodywork and Movement Therapies     Hybrid Journal   (Followers: 18)
Journal of Complementary and Alternative Medical Research     Open Access   (Followers: 1)
Journal of Complementary and Integrative Medicine     Hybrid Journal   (Followers: 12)
Journal of Dance Medicine & Science     Full-text available via subscription   (Followers: 14)
Journal of Evidence-Based Integrative Medicine     Open Access   (Followers: 18)
Journal of Fasting and Health     Open Access   (Followers: 1)
Journal of Ginseng Research     Open Access  
Journal of Health Science and Alternative Medicine     Open Access   (Followers: 1)
Journal of Health Sciences Scholarship     Open Access  
Journal of Herbal Drugs (An International Journal on Medicinal Herbs)     Open Access   (Followers: 1)
Journal of Herbal Medicine     Hybrid Journal   (Followers: 2)
Journal of Herbal Science     Full-text available via subscription   (Followers: 6)
Journal of Integrative Medicine     Full-text available via subscription   (Followers: 4)
Journal of Integrative Medicine & Therapy     Open Access   (Followers: 2)
Journal of Manual & Manipulative Therapy     Hybrid Journal   (Followers: 17)
Journal of Medicinal Plants for Economic Development     Open Access  
Journal of Medicinally Active Plants     Open Access   (Followers: 2)
Journal of Natural Remedies     Open Access   (Followers: 3)
Journal of Nutraceuticals and Herbal Medicine     Open Access   (Followers: 4)
Journal of Palliative Medicine     Hybrid Journal   (Followers: 48)
Journal of the Australian Traditional-Medicine Society     Full-text available via subscription   (Followers: 1)
Journal of Traditional and Complementary Medicine     Open Access   (Followers: 4)
Journal of Traditional Chinese Medical Sciences     Open Access   (Followers: 1)
Journal of Yoga & Physical Therapy     Open Access   (Followers: 9)
Lekovite Sirovine     Open Access  
Médecine Palliative : Soins de Support - Accompagnement - Éthique     Full-text available via subscription   (Followers: 2)
Medical Acupuncture     Hybrid Journal   (Followers: 6)
Medicines     Open Access   (Followers: 1)
Mersin Üniversitesi Tıp Fakültesi Lokman Hekim Tıp Tarihi ve Folklorik Tıp Dergisi     Open Access  
Muller Journal of Medical Sciences and Research     Open Access  
Natural solutions     Full-text available via subscription  
Natural Volatiles & Essential Oils     Open Access   (Followers: 1)
Nigerian Journal of Natural Products and Medicine     Full-text available via subscription  
OA Alternative Medicine     Open Access   (Followers: 1)
Oriental Pharmacy and Experimental Medicine     Partially Free   (Followers: 3)
Research Journal of Medicinal Plant     Open Access   (Followers: 2)
Research Journal of Pharmacognosy     Open Access  
Revista Brasileira de Plantas Medicinais     Open Access   (Followers: 1)
Revista Internacional de Acupuntura     Full-text available via subscription  
South African Journal of Plant and Soil     Hybrid Journal   (Followers: 1)
Synfacts     Hybrid Journal   (Followers: 7)
Traditional & Kampo Medicine     Full-text available via subscription  
Traditional Medicine Journal     Open Access   (Followers: 2)
World Journal of Acupuncture - Moxibustion     Full-text available via subscription   (Followers: 1)
World Journal of Traditional Chinese Medicine     Open Access   (Followers: 1)
Yoga Mimamsa     Open Access   (Followers: 2)
Zeitschrift für Orthomolekulare Medizin     Hybrid Journal   (Followers: 2)

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Similar Journals
Journal Cover
Fitoterapia
Journal Prestige (SJR): 0.937
Citation Impact (citeScore): 3
Number of Followers: 9  
 
  Hybrid Journal Hybrid journal (It can contain Open Access articles)
ISSN (Print) 0367-326X - ISSN (Online) 1873-6971
Published by Elsevier Homepage  [3203 journals]
  • Structural modification of trilobolide for upgrading its immunobiological
           properties and reducing its cytotoxic action
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Juraj Harmatha, Miloš Buděšínský, Michal Jurášek, Tomáš Zimmermann, Pavel Drašar, Zdeněk Zídek, Eva Kmoníčková, Lucie VejvodováGraphical abstractScreened for in vitro biological activity demonstrated by cytotoxic and NO-stimulatory effects in rat peritoneal cells, in relation to their expected immunomodulatory action.Unlabelled Image
       
  • Commipholactam A, a cytotoxic sesquiterpenoidal lactam from Resina
           Commiphora
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Si-Si Zhu, Da-Peng Qin, Shao-Xiang Wang, Cui Yang, Gan-Peng Li, Yong-Xian ChengDiverse terpenoids including a novel sesquiterpenoidal lactam, commipholactam A (1), and a structurally related new cadinane sesquiterpenoid, commiphorane H (2), a new eudesmane sesquiterpenoid, commiphorane I (4), a new guaiane sesquiterpenoid, commiphorane J (5), and two new nor-abietane diterpenoids, commiphoranes K1 and K2 (6 and 7) along with two known terpenoids (3 and 8), were isolated from Resina Commiphora. Their structures with absolute configurations were characterized by spectroscopic methods and calculated electronic circular dichroism (ECD). Notably, commipholactam A represents the first example of cadinane sesquiterpene alkaloids isolated from Resina Commiphora. Biological assessment toward human cancer cells showed that the IC50 values of 1 against HepG2 and A549 cells were 21.73 μM and 128.50 μM, respectively.Graphical abstractUnlabelled Image
       
  • Anti-tumor effects and 3D-quantitative structure-activity relationship
           analysis of bufadienolides from toad venom
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Jun-Shan Liu, Li-Juan Deng, Hai-Yan Tian, Zhi-Xiong Ruan, Hui-Hui Cao, Wen-Cai Ye, Dong-Mei Zhang, Zhi-Ling YuToad venom (venenum bufonis, also called Chan'su) has been widely used for centuries in China to treat different diseases, especially for cancer. Bufadienolides are mainly responsible for the anti-cancer effects of toad venom. However, systematic chemical composition and cytotoxicity as well as key pharmacophores of these bufadienolides from toad venom have not yet been defined clearly. To enrich the understanding of the diversity of bufadienolides and to find bufadienolides with better activities from toad venom. This study was carried out to isolate chemical constituents, research their anti-tumor effects and mechanisms by MTT assay, flow cytometry and Western blotting, and develop a CoMFA and CoMSIA quantitative structure-activity relationship (QSAR) model for illustrating the vital relationship between the chemical structures and cytotoxicities. Among 47 natural bufadienolides, most of bufadienolides (21 compounds isolated in this study and 26 compounds isolated previously) could significantly inhibit the proliferation of cancer cells, and compounds 1, 8, 12, 18 and 19 showed the most potent inhibitory activity against four types of human tumor cells. Compound 18 induced G2/M cell cycle arrest and apoptosis. Moreover, 3D contour maps generated from CoMFA and CoMSIA identified several pharmacophores of bufadienolides responsible for the anti-tumor activities. Our study might provide reliable information for future structure modification and rational drug design of bufadienolides with anticancer activities in medical chemistry.Graphical abstractUnlabelled Image
       
  • Triterpenoids from Euphorbia pulcherrima with inhibitory effects
           on osteoclastogenesis
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Yan Dai, Shaonan Liu, Jun Xu, Chao Zhao, Qiong GuThree new compounds (1–3), euphorimaoid A (1), euphorimaoid B (2), 1α-hydroxy-3β-acetoxy-olean-9,12-diene (3), two firstly isolated natural products 3β-acetyloxy-olean-13(18)-en-12-one (4) and 18,19-epoxyolean-3β-ol acetate (5), together with 13 known compounds (6–18) have been identified from the aerial parts of Euphorbia pulcherrima Willd. Structures of compounds 1–5 were elucidated by comprehensive spectroscopic analysis. The absolute configuration of euphorimaoid A (1) was established using single crystal X-ray diffraction analysis. All the isolates were evaluated for their inhibition of osteoclastogenesis in BMMs. Among them, compounds 7 and 10 showed significantly inhibition in a concentration-dependent manner.Graphical abstractUnlabelled Image
       
  • Benzofurans from Eupatorium chinense enhance insulin-stimulated glucose
           uptake in C2C12 myotubes and suppress inflammatory response in RAW264.7
           macrophages
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Jiang-Huan Ke, Li-Sha Zhang, Shi-Xin Chen, Sheng-Nan Shen, Tian Zhang, Chang-Xin Zhou, Jian-Xia Mo, Li-Gen Lin, Li-She GanFourteen acetylbenzofuran derivatives, including three undescribed carbon skeletons with a newly formed hexane or benzene ring on the other side of the benzofuran ring, (±)-eupatonin A (1), (±)-eupatonin B (2), and eupatonin C (3), two new benzofurans (−)-12β-hydroxygynunone (4) and (+)-12-hydroxyl-13-noreuparin (5), as well as 9 known ones (6–14), were isolated from 95% ethanol extract of the roots of Eupatorium chinense. Their structures were determined by spectroscopic methods and quantum chemical DFT and TDDFT calculations of the NMR chemical shifts and ECD spectra, which helped in the determination of the relative configurations of 1 and 2 and the absolute configurations of 4 and 5, respectively. 1 and 2 were further identified to be racemic mixtures by chiral HPLC analysis. All compounds were evaluated for insulin-stimulated glucose uptake in differentiated C2C12 myotubes. Compounds 1, 3, 4, 5, 11, 12, and 13 markedly enhanced insulin-mediated glucose uptake. (±)-Eupatonin A (1) activated the IRS-1/Akt/GSK-3β signaling pathway and enhanced insulin stimulated GLUT4 membrane translocation in C2C12 myotubes. On LPS stimulated RAW264.7 macrophages, several compounds exhibited significant inhibitory effect on NO production with IC50 values ranging from 4.94 to 9.70 μΜ. (±)-Eupatonin A (1) again dose-dependently suppressed LPS-induced NO production and decreased the expression of inducible NO synthase (iNOS), through inhibiting NF-κB activity.Graphical abstractUnlabelled Image
       
  • An unprecedented chlorine-containing piperamide from Piper pseudoarboreum
           as potential leishmanicidal agent
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Ninoska Flores, Juan C. Ticona, Pablo Bilbao-Ramos, M. Auxiliadora Dea-Ayuela, Juan C. Ruiz Macedo, Isabel L. Bazzocchi, Francisco Bolás-Fernández, Ignacio A. JiménezA phytochemical investigation of the ethanolic extract of leaves from Piper pseudoarboreum led to the isolation of 3-chlorosintenpyridone 1, an unprecedented chlorinated piperamide, together with the known compounds 2–12. Their structures were established based on 1D and 2D (COSY, ROESY, HMQC, and HMBC) NMR spectroscopy, in addition to high resolution mass spectrometry. The proposed biosynthetic pathway of compound 1 is discussed. Compounds 1–12 were tested in vitro for their leishmanicidal potential against promastigote stages of Leishmania amazonensis, L braziliensis, L. guyanensis and L. infantum. Two compounds from this series, the alkamide 1 (IC50 3.4–5.2 μM) and the fatty acid 9 (IC50 18.7–29.6 μM) displayed higher or similar potency to Miltefosine, used as the reference drug.Graphical abstractUnlabelled Image
       
  • Antifungal coumarins and lignans from Artemisia annua
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Ke-Ming Li, Xian Dong, Yu-Nan Ma, Ze-Hong Wu, Yong-Ming Yan, Yong-Xian ChengTwo new coumarins (1 and 2), two new lignans (3 and 4), one new phloroglucinol derivative (5), together with eleven known compounds, were isolated from Artemisia annua. Their structures were identified by spectroscopic methods with 1 to be secured by X-ray diffraction. Antifungal activities of the isolates against Fusarium oxysporum, Fusarium solani, and Cylindrocarpon destrutans were evaluated. It was found that compound 1 could inhibit all the fungal strains with respective MIC values of 18.75, and 25.00 μg/mL. In contrast, compounds 4, 5, 7, and 8 are active toward C. destrutans and 14 displays inhibitory property toward F. solani.Graphical abstractUnlabelled Image
       
  • Cytotoxic, antimicrobial and antiviral secondary metabolites produced by
           the plant pathogenic fungus Cytospora sp. CCTU A309
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Abolfazl Narmani, Rémy Bertrand Teponno, Mahdi Arzanlou, Frank Surup, Soleiman E. Helaly, Kathrin Wittstein, Dimas F. Praditya, Asadollah Babai-Ahari, Eike Steinmann, Marc StadlerChemical analysis of extracts from cultures of the plant pathogenic fungus Cytospora sp. strain CCTU A309 collected in Iran led to the isolation of two previously unreported heptanedioic acid derivatives namely (2R,3S) 2-hydroxy-3-phenyl-4-oxoheptanedioic acid (1) and (2S,3S) 2-hydroxy-3-phenyl-4-oxoheptanedioic acid (2) as diastereomers, four previously undescribed prenylated p-terphenyl quinones 3–6 in addition to five known metabolites. Their structures were elucidated on the basis of extensive spectroscopic analysis and high-resolution mass spectrometry. For metabolites 1 and 2, the absolute configurations at C-2 were deduced from comparison of the 1H NMR difference of their (S)- and (R)-phenylglycine methyl ester derivatives while the relative configurations were tentatively assigned by a J-based analysis and confirmed by comparison of 13C chemical shifts to literature data. The isolated compounds were tested for their cytotoxic, antimicrobial (including biofilm inhibition), antiviral, and nematicidal activities. While only moderate antimicrobial effects were observed, the terphenyl quinone derivatives 3–6 and leucomelone (10) exhibited significant cytotoxicity against the mouse fibroblast L929 and cervix carcinoma KB-3-1 cell lines with IC50 values ranging from 2.4 to 26 μg/mL. Furthermore, metabolites 4–6 showed interesting antiviral activity against hepatitis C virus (HCV).Graphical abstractUnlabelled Image
       
  • Target discovery of chlorogenic acid derivatives from the flower buds of
           Lonicera macranthoides and their MAO B inhibitory mechanism
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Yudan Mei, Dabo Pan, Yingnan Jiang, Weiyang Zhang, Xiaojun Yao, Yi Dai, Yang Yu, Xinsheng YaoChlorogenic acids (CGAs), exhibiting health benefits in many foods, also played an important role for their broad bioactive properties in nature. Obtaining more diverse CGAs was helpful to discover their potential edible and medical value. In this study, 11 CGAs, including four new (1–4) and seven known compounds (5–11), were obtained from the flower buds of Lonicera macranthoides Miq.-Hazz. The possible targets of all isolated CGAs were predicted using the ligand-based reverse screening and compound-target network, suggesting that MAO B (monoamine oxidase B) was the primary target of these CGAs. Subsequently, 7 out of 11 CGAs were confirmed to possess inhibitory effects by in vitro assay. The detailed interaction mechanism between compound and MAO B was also announced by molecular docking and molecular dynamics simulation.Graphical abstractUnlabelled Image
       
  • Isolation of a spirolactone norditerpenoid as a yeast Ca2+ signal
           transduction inhibitor from Kuji amber and evaluation of its effects on
           PPM1A activity
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Eisaku Shimizu, Hiroyuki Koshino, Aoi Noro, Miku Maruyama, Nozomu Shimoda, Shota Uesugi, Motoko Ohnishi, Ken-ichi KimuraA different type of biologically active compound from Kuji amber (Late Cretaceous, Japan) before the K-Pg boundary [65 million years ago (Ma)] was isolated based on the growth-restoring activity of a mutant yeast involving Ca2+ signal transduction. It was identified as a spirolactone norditerpenoid, (4R*, 5S*, 8R*, 9R*, 10S*)-14,15,16,19-tetranor-labdan-13,9-olide (1) from spectral analyses with high-resolution electron ionization mass spectrometry (HREIMS), 1D and 2D nuclear magnetic resonance (NMR). Although the planar structure of 1 is known as an artificial derivative from marrubiin, it was isolated as a natural product from Kuji amber and its structure was elucidated for the first time. It had a growth-restoring activity against the mutant yeast through the direct or indirect inhibition of calcineurin activity [protein phosphatase, Mg2+/Mn2+-dependent 1A (PPM1A) activation]. Furthermore, the compound had potent inhibitory effect against the degranulation of rat basophilic leukemia 2H3 (RBL-2H3) cells.Graphical abstractUnlabelled Image
       
  • Chemical constituents of the trunks and roots of Thuja
           sutchuenensis
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Xueying Guo, Miaomiao Wang, Jiafeng Wu, Guiyun Wu, Xiao Zhang, Luqiong Huo, Hongxin Liu, Yihong Chen, Guowen Xie, Haibo Tan, Sheng-Xiang QiuFive new compounds including two stilbenes, designated thujasutchins A (1) and B (2), two phenolic compounds namely thujasutchins C (3) and D (4), as well as one sesquiterpene thujasutchin E (5), were isolated from the 95% ethanolic extract from the trunks and roots of Thuja sutchuenensis. Their structures were determined by means of extensively spectroscopic analysis including UV, IR, HRESIMS, 1H and 13C NMR (COSY, HSQC, HMBC). Moreover, compounds 1, 3–5 were evaluated for in vitro cytotoxic activities against SF-268, MCF-7, HepG-2, and A549 tumor cell lines.Graphical abstractUnlabelled Image
       
  • Sinensiols B-G, six novel neolignans from Selaginella sinensis
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Xi Chen, Ping-Sheng Xu, Zhen-Xing Zou, Yang Liu, Wen-Hao Zhou, Qin Ren, Dan Li, Xiao-Min Li, Kang-Ping Xu, Gui-Shan TanSix new neolignans, sinensiols B-G (1–6), together with three known analogues (7–9) were isolated from the whole plant of Selaginella sinensis. Their planar structures were established by comprehensive spectroscopic analyses including 1D, 2D NMR, IR and HRESIMS data. The absolute configurations of new compounds were elucidated by comparing their experimental CD spectra with known ones and using the reversed helicity rule for the 1Lb band ECD of dihydrobenzofuran neolignans. Sinensiols A-D (7, 1–3) belong to sesquilignan with a dimer of dihydrobenzo[b]furan moiety. The potential precursors of sinensiols A, B, D were also reported in this paper. In addition, all new compounds were screened for their cytotoxicity against A549 and HepG2 human cancer cell lines, and they didn't show inhibition on the growth of cancer cells.Graphical abstractUnlabelled Image
       
  • Australeols A−F, neuroprotective meroterpenoids from Ganoderma
           australe
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Jiao-Jiao Zhang, Yun Dong, Fu-Ying Qin, Yong-Xian ChengSix new meroterpenoids, australeols A−F (1–6), together with nineteen known compounds (7–25), were isolated from the fruiting bodies of Ganoderma australe. Their structures including absolute configurations were assigned by using spectroscopic methods, CD comparison, and X-ray crystallography analysis. Biological evaluation reveals that compounds 13, (–)-19, and 23 exhibit potent neuroprotective activities in glutamate-stimulated SH-SY5Y cells.Graphical abstractUnlabelled Image
       
  • Five novel diarylheptanoids from green walnut husks (Juglans regia
           L
    .)
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Hong Yang, Yan Ma, Changjiu Gao, Baihui Wang, ARuhan, Congcong Lin, Hai Feng, Libo Wang, Jian Huang, Jinhui WangA ethanol extract of green walnut husks (Juglans regia L.) was isolated by various chromatographic techniques yielding 5 previously unknown diarylheptanoids, namely Juglanin F (1), Juglanin G (2), Juglanin H (3), Juglanin I (4) and Juglanin J (5), respectively, together with 12 known diarylheptanoids. The structures of these 17 compounds were elucidation on the basis of spectroscopic analysis. Upon evaluation of compounds 1–5 on the human hepatoma cells HepG2, compound 3 exhibited moderate inhibitory activity with IC50 27.72 μM.Graphical abstractUnlabelled Image
       
  • New cyathane diterpenoids with neurotrophic and anti-neuroinflammatory
           activity from the bird's nest fungus Cyathus africanus
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Xia Yin, Jing Wei, Wei-Wei Wang, Yu-Qi Gao, Marc Stadler, Rong-Wei Kou, Jin-Ming GaoEleven new cyathane diterpenoids, designated cyafricanins A–K (1−11), were isolated from the culture broth of the baisidiomycete Cyathus africanus (Nidulariaceae, Bird's nest fungi). Their structures were elucidated by comprehensive analysis of their NMR and HRESIMS data. Cyafricanins A (1) was found to possess an unusual 3,4-seco‑carbon skeleton. All compounds were evaluated for their neurotrophic activity in PC-12 cells and anti-neuroinflammatory activity in BV2 microglia cells. All of the diterpenoids showed nerve growth factor induced neurite outgrowth-promoting activity at concentration of 20 μM. Among them, cyafricanin B (2) and cyafricanin G (7) exhibited promising neurotrophic activity, and cyafricanin A (1) showed strong inhibitory effects on both inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) expression. Furthermore, molecular docking studies revealed that cyafricanin A (1) showed strong interactions with the iNOs protein in the active cavity.Graphical abstractUnlabelled Image
       
  • Asperfuranones A-C, 3(2H)-furanone derivatives from the fungus Aspergillus
           sp. and the configuration reassignment of their eighteen analogues
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Ya-Rong Wu, Guo-Ping Yin, Hong-Liang Gao, Xiao-Bing Wang, Ming-Hua Yang, Ling-Yi KongThree undescribed 3(2H)-furanone derivatives, asperfuranones A-C (1–3), along with one known compound (4) were isolated from the Aspergillus sp. strain obtained from the intestines of centipede. Their structures were determined by NMR and MS spectroscopic analyses, and the absolute configurations were established by the Snatzke's sector rules, modified Mosher's method and electronic circular dichroism (ECD) calculation. Meanwhile, the application of the sector rules led to the reassignment of the absolute configurations of 4 and other seventeen previously reported analogues (5–21).Graphical abstractUnlabelled Image
       
  • Phragmalin-type limonoids with structural diversity at D-ring from the
           fruit shells of Chukrasia tabularis
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Chengcheng Wang, Yi Li, Rong Xu, Panpan Zhang, Wenyan Zhang, Shanshan Wei, Yun Li, Jun Luo, Lingyi KongTen undescribed phragmalin-type limonoids (Chuktabularoids A-J, 1–10) and four known compounds (11–14) were isolated from the fruit shells of Chukrasia tabularis A. Juss. Their chemical structures were elucidated through a combination of HRESIMS, NMR, and ECD experiments. Their frameworks differed mainly in D-ring, including C-15-acyl, 16-nor C-15 acyl, C-13/14/18-cyclopropane, and Δ14, 15 types. The majority of the isolated compounds were investigated for multidrug resistance (MDR) reversal activity against doxorubicin-resistant human breast carcinoma (MCF-7/DOX) cells, compounds 11 and 12 exhibited a 5.6-fold and 19.7-fold enhancing effect on doxorubicin susceptibility at 30 μM, respectively.Graphical abstractUnlabelled Image
       
  • Five new epoxy-5,6,7,8-tetrahydro-2-(2-phenylethyl)chromones from Chinese
           agarwood by artificial holing
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Wei Li, Ge Liao, Hao Wang, Wen-Hua Dong, Li Yang, Fan-Dong Kong, Cai-Hong Cai, Jun Wang, Attila Mándi, Tibor Kurtán, Wen-Li Mei, Hao-Fu DaiFive optically active epoxy-5,6,7,8-tetrahydro-2-(2-phenylethyl)chromone derivatives (1–5) with four chirality centers in the condensed cyclohexene ring were isolated from artificial holing agarwood originating from Aquilaria sinensis (Lour.) Gilg. Their structures were elucidated by spectroscopic techniques (UV, IR, 1D and 2D NMR) and MS analyses. The absolute configuration of 2 was elucidated by TDDFT-ECD calculations and ECD spectra of 1, 3–5 allowed their configurational assignment as well. All of the new compounds contained a condensed oxirane ring, and compound 1 was the only 6,7-epoxy-2-(2-phenylethyl)-5,6,7,8-tetrahydrochromone derivative that has ever been found in agarwood. AChE inhibitory activity was tested for the first time of these new compounds by using modified Ellman's colorimetric method. Compounds 3 and 5 exhibited inhibitory activity against AChE with IC50 value of 441.6, and 155.6 μM, respectively.Graphical abstractUnlabelled Image
       
  • Therapeutic potential of monoterpene α-thujone, the main compound of
           Thuja occidentalis L. essential oil, against malignant glioblastoma
           multiforme cells in vitro
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Maciej Pudełek, Jessica Catapano, Paweł Kochanowski, Krzysztof Mrowiec, Natalia Janik-Olchawa, Jarosław Czyż, Damian RyszawyThuja occidentalis L. is indigenous for Northern America and commonly cultivated in Europe. Raw materials obtained from this tree are widely applied in the ethnomedicine and phytotherapy of numerous ailments, incl. scurvy, cystitis, rheumatism and cancer. Despite wide medicinal applications of Thuja occidentalis, still little is known on its therapeutic potential in tumor treatment. α-thujone is the main component of Thuja occidentalis essential oil, which has been suggested to possess anti-tumor activities. This monoterpene easily penetrates the blood-brain barrier. Therefore, we examined its effects on the malignancy of glioblastoma multiforme (GBM) cells, with the special emphasis on the mechanisms of its effect on cell viability and invasiveness. α-thujone exerted the attenuating effect on the viability and proliferation of GBM cells when administered at the concentrations between 100 and 500 μg/ml (660 μM – 3.2 mM). This effect was correlated with the induction of apoptosis in GBM cell populations and with considerable inhibition of GBM cells motility. Mechanistic analyses demonstrated the induction of oxidative stress and autophagy in α-thujone-treated tumor cells, whereas normal astrocytes displayed considerably lower sensitivity to α-thujone. Our observations demonstrate that α-thujone exerts pro-apoptotic and anti-invasive effects on GBM cells. They confirm the potential of α-thujone for the treatment of glioblastoma multiforme.Graphical abstractUnlabelled Image
       
  • Anxiolytic effect of a novel 9,10-dihydrophenanthrene, juncuenin H, is
           associated with metabolic changes in cortical serotonin/dopamine levels in
           mice
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Lu Sun, Chanxi Zhang, Chen Xue, Chuanxin Liu, Yumei Wang, Lei Chen, Yanping Deng, Jianmei Huang, Haifeng ZhaiTwo novel phenanthrenoids, juncuenin H (1) and dijuncuenin B (2), together with eight known phenanthrenoids, effusol (3), dehydroeffusol (4), juncusol (5), dehydrojuncusol (6), juncuenin B (7), dehydrojuncuenin B (8), juncuenin A (9), and dehydrojuncuenin A (10), were isolated from the underground parts of Juncus setchuenensis. The structures of the compounds were determined by 1D and 2D NMR and mass spectroscopy. The anxiolytic activities of compounds 1, 6, 9, and 10 were evaluated. In order to explore the mechanisms underlying their anxiolytic activities, the levels of serotonin (5-HT), dopamine (DA), and their metabolites in the cerebral cortex and hippocampus of mice treated with compound 1 were determined by quantitative mass spectrometry. The mice treated with compound 1 had significantly lower levels of 5-HT, 3-methoxytyramine (3-MT), 5-hydroxyindole-3-acetic acid (5-HIAA), homovanillic acid (HVA), and 3, 4-dihydroxyphenylacetic acid (DOPAC) in the cerebral cortex than those of the vehicle control-treated mice. The levels of HVA and 5-HIAA in the hippocampus were also significantly lower in the mice treated with compound 1 than in the control group mice. These results suggest that the metabolic changes, reflected in the levels of DA and/or 5-HT, may contribute to the anxiolytic activity of the phenanthrenoids studied herein.Graphical abstractUnlabelled Image
       
  • Isoforrethins A–D, four ent-abietane diterpenoids from Isodon forrestii
           var. forrestii
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Ling Chen, Qian Yang, Kun Hu, Xiao-Nian Li, Han-Dong Sun, Pema-Tenzin PunoFour new ent-abietane diterpenoids, isoforrethins A–D (1–4), were isolated from the aerial parts of Isodon forrestii var. forrestii by a variety of chromatographic techniques. Their structures were elucidated on the basis of spectroscopic data interpretation, single crystal X-ray diffraction, and quantum chemical calculation. All of these compounds were evaluated for their cytotoxicity against five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW-480), and compound 4 showed significant inhibitory activities against SMMC-7721, A-549, MCF-7, and SW-480.Graphical abstractUnlabelled Image
       
  • Bioassay-guided isolation and structure elucidation of cytotoxic stilbenes
           and flavonols from the leaves of Macaranga barteri
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Peter A. Segun, Omonike O. Ogbole, Fyaz M.D. Ismail, Lutfun Nahar, Andrew R. Evans, Edith O. Ajaiyeoba, Satyajit D. SarkerBioassay-guided fractionation of the leaves of Macaranga barteri collected from Nigeria led to the isolation of three previously undescribed cytotoxic stilbenes, macabartebenes A–C (1–3), together with six known compounds including prenylated stilbenes: vedelianin (4), schweinfurthin G (5), and mappain (7), prenylated flavonols: 8-prenylkaempferol (6), and broussoflavonol F (8), and the geranylated flavonol, isomacarangin (9). The cytotoxicity of the compounds was evaluated against four human cancer cell lines, with vinblastine as the positive control and DMSO vehicle as the negative control. Vedelianin (IC50 = 0.32–0.54 μM) displayed the greatest antiproliferative activity across the panel of cancer cell lines amongst the compounds, while macabartebene A (IC50 = 0.60–0.79 μM) was the most potent of the previously unreported compounds. The compounds displayed varying selectivity towards the cancer cell lines compared to the normal human prostate cell line. The findings of this study revealed that M. barteri leaves contain several cytotoxic compounds.Graphical abstractUnlabelled Image
       
  • Absolute configuration determination of asarinin by synchrotron radiation
           with crystalline sponge method
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Kan Li, Da-Song Yang, Xiao-Fei Gu, Bin DiThe determination of the absolute configuration of natural products still faces many challenges, especially the active pharmaceutical ingredient which is trace, oily and novel structures. Currently, NMR requires chiral reagents in determining the absolute configuration; ECD involves theoretical calculations and requires chromophores. In this study, the absolute configuration of asarinin had successfully identified by using synchrotron radiation with crystalline sponge method and combining MS with NMR. This method could identifying the crystal structure of trace amorphous substances, resolving the problem of absolute configuration of multi-chiral central compounds, and hopefully providing a new idea and approach for structural elucidation of natural products.Graphical abstractUnlabelled Image
       
  • Antimicrobial guaianolide sesquiterpenoids from leaves of the Saudi
           Arabian plant Anvillea garcinii
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Shagufta Perveen, Jawaher Alqahtani, Raha Orfali, Areej Mohammad Al-Taweel, Hasan Soliman Yusufoglu, Maged Saad Abdel-Kader, Orazio Taglialatela-ScafatiAnvillea garcinii is a medicinal plant used in the Arab region for intestinal diseases, lungs and liver diseases, digestive problems, and as an anti-diabetic. Repeated chromatographic purifications of A. garcinii leaves led to the isolation of two undescribed guaiane sesquiterpene lactones (1–2), along with four known germacranolides (3–6). The structures of the new compounds were established using spectroscopic (1D, 2D NMR) and spectrometric methods (ESIMS). Compounds 1 and 2 were shown to possess hydroxyl substituents at position 9, a structural feature rarely reported in guaianolide-type sesquiterpenes. The antimicrobial activity of 1–6 was screened against five different gram-positive/negative bacteria and the fungi Candida albicans and C. parapsilosis. Compounds 1 and 2 displayed remarkable antifungal effect against C. albicans and C. parapsilosis and potent antibacterial activities against Staphylococcus aureus.Graphical abstractUnlabelled Image
       
  • Aromatic monoterpenoid glycosides from rattan stems of Schisandra
           chinensis and their neuroprotective activities
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Yan Liu, Jiang-Tao Guo, Zhi-Bin Wang, Zu-Yi Li, Gui-Xue Zheng, Yong-Gang Xia, Bing-You Yang, Hai-Xue KuangSix new monoterpenoid glycosides, including thymoquinol 5-O-α-L-arabinopyranosyl-(1 → 6)-β-D-glucopyranoside (1), cuminic acid 7-O-α-D-arabinofuranosyl-(1 → 6)-β-d-glucopyranosyl ester (2), p-cymene 7-O-α-D-arabinofuranosyl-(1 → 6)-β-D-glucopyranoside (3), p-methylhyd- ratropic acid 9-O-α-D-arabinofuranosyl-(1 → 6)-β-d-glucopyranosyl ester (4), (R)-p-cymene 9-O-α- D-arabinofuranosyl-(1 → 6)-β-D-glucopyranoside (5), and (R)-p-cymene 9-O-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside (6), together with three known compounds, such as (R)-p-cymene 9-O-β-D-glucopyranoside (7), thymoquinol 5-O-β-D-glucopyranoside (8), and thymoquinol 2-O-β-D-glucopyranoside (9) were isolated from the 70%-EtOH extract of Schisandra chinensis rattan stems. The structures of the new compounds were elucidated by detailed spectroscopic analyses. Meanwhile, the neuroprotective activities of compounds 1–9 were evaluated on the two co-culture models of microglia and neurons cells and astrocytoma and neurons cellsGraphical abstractUnlabelled Image
       
  • Bis-iridoid and iridoid glycosides: Viral protein R inhibitors from
           Picrorhiza kurroa collected in Myanmar
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Nwet Nwet Win, Takeshi Kodama, Khine Zar Wynn Lae, Yi Yi Win, Hla Ngwe, Ikuro Abe, Hiroyuki MoritaFour new bis-iridoid glycosides, saungmaygaosides A-D (1–4), and six known iridoid glycosides (5–10) were isolated from the n-butanol extract of the stems of Picrorhiza kurroa collected in Myanmar. Their structures were elucidated by extensive spectroscopic techniques. All of the isolates were assayed for anti-Vpr activity, using TREx-HeLa-Vpr cells. Among the isolates, saungmaygaoside D (4), sylvestroside IV dimethyl acetal (7), and sweroside (8) were the most potent inhibitors with effective doses of 5 and 10 μM, respectively, without showing any notable cytotoxicities.Graphical abstractUnlabelled Image
       
  • Diverse lignans with anti-inflammatory activity from Urceola
           rosea
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Dou-Dou Dong, Heng Li, Kun Jiang, Shi-Jin Qu, Wei Tang, Chang-Heng Tan, Yi-Ming LiSeventeen structurally diverse lignans, comprising six new compounds, ecdysanols A (1), B (11), C – E (13–15), and F (17), were isolated from the caulis of Urceola rosea. The structures and absolute configurations of these new compounds were elucidated by means of extensive analysis of mass and NMR data, as well as chiroptical properties. A bioassay in vitro showed that all lignans possessed anti-inflammatory effects by inhibiting the production of TNF-α, NO and/or IL-6 in LPS-stimulated RAW264.7 cells. Ecdysanol F (17) showed the most strongly effect against NO and IL-6 levels.Graphic abstractUnlabelled Image
       
  • Trichobisabolins A-H, eight new bisabolane derivatives from the
           marine-alga-epiphytic fungus Trichoderma asperellum Y6–2
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Zhen-Zhen Shi, Feng-Ping Miao, Sheng-Tao Fang, Xiu-Li Yin, Nai-Yun JiEight new bisabolane derivatives, trichobisabolins A-H, along with two known ones, (3R,6R,7R)-1,10-bisaboladien-3-ol (9) and (3R,6R,7S)-1,10-bisaboladien-3,6-diol (10) were isolated from the culture of Trichoderma asperellum Y6–2, obtained from the surface of the marine red alga Chondrus ocellatus. Their structures and relative configurations were identified by interpretation of 1D/2D NMR and MS data. Compounds 1–8 were assayed for inhibiting the growth of some marine-derived organisms, including four marine phytoplankton species, one marine zooplankton species, and five pathogenic bacteria. All of them exhibited inhibition against the marine phytoplanktons with IC50 values ranging from 2.1–78 μg/mL, compounds 4 and 8 showed weak lethality to the marine zooplankton, and none of them had inhibition against the five pathogenic bacteria.Graphical abstractUnlabelled Image
       
  • The protective effects of vernicilignan A, a new flavonolignan isolated
           from Toxicodendron vernicifluum on SH-SY5Y cells against oxidative
           stress-induced injury
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Meichen Li, Yanhua Fan, Ting Zhong, Ping Yi, Chengcheng Fan, Andong Wang, Jianyu Liu, Yongnan XuIn this study, a new flavonolignan vernicilignan A was isolated from Toxicodendron vernicifluum. The neuroprotective effects of this compound against H2O2 induced cell injury in SH-SY5Y cells were evaluated by MTT assay and LDH release assay. Vernicilignan A dose-dependently attenuated the cell injury and LDH release induced by H2O2 in SH-SY5Y cells. Further study indicated that vernicilignan A reduced cell apoptosis caused by H2O2 treatment via regulation of some apoptotic related proteins including Bax, Bcl-2, caspase 3 and caspase 9. Also, vernicilignan A increase the cell viability of H2O2 treated cells via the activation of Akt and GSK3β. Base on the findings, vernicilignan A exhibited neuroprotective effects through the activation of PI3K/Akt signaling and inhibition of mitochondria apoptosis pathway. Vernicilignan A might be a promising therapeutic agent for oxidative stress induced neurodegenerative diseases.Graphical abstractUnlabelled Image
       
  • New knowledge about old drugs; a cardenolide type glycoside with cytotoxic
           effect and unusual secondary metabolites from Digitalis grandiflora Miller
           
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Vahap Murat Kutluay, Toshiaki Makino, Makoto Inoue, Iclal SaracogluPhytochemical investigation of the aerial parts of Digitalis grandiflora Miller (Plantaginaceae) led to the isolation of an undescribed cardenolide type glycoside digigrandifloroside (1) along with five known compounds, rengyoside A (2), rengyoside B (3), cleroindicin A (4), salidroside (5), and cornoside (6), from its aqueous fraction of methanolic extract. Structures of the isolated compounds were determined by means of spectroscopic techniques. 1–6 were isolated for the first time from D. grandiflora. 2 and 3 are being reported for the first time from Digitalis genus and Plantaginaceae family with this study. This is the second report for occurrence of 4 from a Digitalis species. Cytotoxic activity of the aqueous fraction was also tested against HEp-2 (Human larynx epidermoid carcinoma) and HepG2 (Human hepatocellular carcinoma) cancer cell lines and L929 (Mouse fibroblast cell) non-cancerous cell line. Aqueous fraction showed stronger cytotoxicity on HEp-2 cells than HepG2. Therefore, the cytotoxic activity of 1, 2, 4, and 6 were tested against HEp-2 and L929 cell lines. 3 and 5 couldn't be tested due to their insufficient amount. 1 showed the highest cytotoxicity against HEp-2 cells with IC50 value 10.1 μM when compared with the positive control, etoposide and 2–6 (IC50 of etoposide; 39.5 μM).Graphical abstractPhytochemical investigation of the aerial parts of Digitalis grandiflora Miller (Plantaginaceae) led to the isolation of an undescribed cardenolide type glycoside digigrandifloroside along with five known compounds. Digigrandifloroside showed the highest cytotoxicity against HEp-2 cells with IC50 value 10.1 μM.Unlabelled Image
       
  • Bioactive homogentisic acid derivatives from fruits and flowers of
           Miliusa velutina
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Trinop Promgool, Kwanjai Kanokmedhakul, Sarawut Tontapha, Vittaya Amornkitbamrung, Saowanit Tongpim, Winai Jamjan, Somdej KanokmedhakulChromatographic separation of fruits and flowers of the Thai medicinal plant, Miliusa velutina, resulted in the isolation of five new rare homogentisic acid derivatives, miliusanal (1) and miliusanones A-D (2–5), together with fifteen known secondary metabolites (6–20). Their structures were determined through the use of extensive spectroscopic data. The absolute configurations of homogentisic acid derivatives 2–7 were identified using NOESY data and a comparison of experimental and calculated ECD spectral data. Compounds 2, 3, 6, and 7 showed antimalarial activity with IC50 values in the range of 3.3–5.2 μg/mL. Compound 6 also showed activity against Mycobacterium tuberculosis with an MIC value of 50 μg/mL. Compounds 1–3, 6 and 7 exhibited cytotoxicity againt KB, MCF-7, NCI-H187 and Vero cell lines with IC50 values in the range of 5.8–40.4 μg/mL. In addition, compounds 1, 2 and 6 showed moderate antibacterial activities against three Gram-positive bacteria (Bacillus cereus, Staphylococcus aureus, and Methicillin resistant S. aureus) with MICs in the range of 32–64 μg/mL.Graphical abstractUnlabelled Image
       
  • Aromatic constituents from Ganoderma lucidum and their neuroprotective and
           anti-inflammatory activities
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Shuang-Yang Lu, Xing-Rong Peng, Jin-Run Dong, Hui Yan, Qing-Hua Kong, Qiang-Qiang Shi, Da-Shan Li, Lin Zhou, Zhong-Rong Li, Ming-Hua QiuFive new aromatic compounds, designed as lucidumins A-D (1–4) and lucidimine E (9), along with seven known aromatic compounds (5–8, 10–12) were isolated from Ganoderma lucidum. Their structures were determined by spectroscopic method. Bioactive evaluation showed that compounds 2–4 and 6–10 displayed remarkable neuroprotective activities against corticosterone-induced PC12 cell damage, with the cell viability ranging from 69.99% to 126.00%; and compounds 1–4, 9 and 10 exhibited significant anti-inflammatory activities against LPS-induced nitric oxide (NO) production in RAW264.7 macrophages, with IC50 values ranging from 4.68 to 15.49 μM. In particular, compound 10 showed remarkable neuroprotection with EC50 value of 2.49 ± 0.12 μM, and potent anti-inflammation with IC50 value of 4.68 ± 0.09 μM.Graphical abstractUnlabelled Image
       
  • Caesalminaxins O-T, cassane diterpenoids from the seeds of Caesalpinia
           minax and their anti-inflammation
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Qing-Feng Ruan, Xing-Hong Zhou, Shi-Qin Jiang, Bao Yang, Jing Jin, Hui Cui, Zhong-Xiang ZhaoSix previously undescribed cassane diterpenoids, named caesalminaxins O-T (1–6), together with 28 known compounds (7–34), were isolated from the seeds of Caesalpinia minax Hance. Their structures, including their absolute configurations were elucidated by extensive spectroscopic analysis, X-ray diffraction, and quantum chemical calculations. Among the undescribed diterpenoids, compound 6 that possessed an unusual enol group at C-7 with a highly deshielded 1H NMR signal was the first example in cassane diterpenoids. All of the isolates were evaluated for their inhibitory activity against lipopolysaccharide-activated NO production in RAW264.7 cells. Compound 16 showed moderate inhibitory activity with an IC50 value of 17.3 μM, which was more potent than the positive control (indomethacin, IC50 = 29.7 μM).Graphical abstractUnlabelled Image
       
  • Antiproliferative ent-kaurane diterpenoids isolated from the
           roots of Zea mays L.
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Andong Wang, Yanhua Fan, Qing Ouyang, Chengcheng Fan, Bin Lin, Jianyu Liu, Yongnan XuFour new ent-kaurane diterpenoid maizediterpenes A-D (1–4), along with fourteen known compounds were isolated from the roots of Zea mays (maize). Compounds 7, 15, 16 were isolated from this genus for the first time. The planar structures of the new compounds were determined by extensive analysis of their NMR and HR-ESI-MS spectra, and the absolute configurations were established on the basis of specific rotation in association with calculated ECD spectra. Compounds 2, 6 and 18 showed significant antiproliferative effects against five human cancer cell lines (A549, MDA-MB-231, SK-Hep-1, SNU638, HCT116) with IC50 values ranging from 1.99 ± 0.41 μM to 15.18 ± 1.17 μM.Graphical abstractUnlabelled Image
       
  • Antioxidant constituents of chrysanthemum ‘jinsidaju’
           cultivated in Kaifeng
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Fenqin Zhao, Qianqian Zhang, Yan Yan, Haiyan Jia, Xinran Zhao, Xiying Li, Lihua Zheng, Guang HanDendranthema morifolium cv. ‘jinsidaju’, cultivated only in Kaifeng, has been eaten for more than 1000 years. During the antioxidant-activity-guided studies on its chemistry and health care function, two new bisabolane-type sesquiterpenes, (6R,7R)-7-hydroxybisabol-2,9E,11-triene-4-one (jinsidajuol A, 1) and (6R,7R)-7-hydroxy-11-methoxybisabol-2,9E-diene-4-one (jinsidajuol B, 2), and thirteen known compounds (3–15) were isolated from the flowers. Their structures were elucidated by 1D and 2D NMR spectroscopy and HRMS. 1 and 2 are the first example of bisabolane-type sesquiterpenes isolated from the genus Dendranthema. Compounds 6–8, 12 and 13 exhibited strong scavenging activities on the ABTS radical cation with IC50 3.33, 5.67, 2.00, 2.50, 5.33 μg/mL, respectively. The IC50 values of all compounds on HepG2 human hepatoma tumor cell line were higher than 50 μM.Graphical abstractUnlabelled Image
       
  • The antagonism between apigenin and protoapigenone to the PDK-1 target in
           Macrothelypteris torresiana
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Ziwei Liu, Shuang Cao, Can Jin, Yu He, Xiaoshun Zhou, Heng Zhang, Zhimei LiuApigenin and protoapigenone that both have the activities against various cancer cell lines co-exist in Macrothelypteris torresiana, while the extracts of M. torresiana couldn't achieve the fine anti-tumor effects for the existence of potent anti-tumor compounds. This study disclosed an antagonism between the two compounds on the protein level to elucidate the paradox. First, the study established the fingerprint for M. torresiana extract. The following anti-proliferation assay verified that the antagonism occurs between protoapigenone and apigenin. And then Western blot and qt-PCR were applied to evaluate the expression and transcription level of the Akt phosphorylation related targets to validate the antagonism at the protein level. Moreover, CETSA further validated the binding of PDK-1 with apigenin and protoapigenone, as well as the antagonism between the two compounds. Finally, the compound-protein complexes predicted by SYBYL-X gave the visual results for the antagonism. The results demonstrated that: Due to the structural similarity and close binding coefficients to the identical targets, when the cells were treated with apigenin and protoapigenone simultaneously, the Akt phosphorylation inhibition induced by protoapigenone would attenuate significantly. The antagonism disclosed in this paper could be a new explanation for the unsatisfied efficacy of M. torresiana extract.Graphical abstractUnlabelled Image
       
  • Hibiscus acid from Hibiscus sabdariffa (Malvaceae) has a vasorelaxant
           effect on the rat aorta
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Ahmed M. Zheoat, Alexander I. Gray, John O. Igoli, Valerie A. Ferro, Robert M. DrummondHibiscus sabdariffa (Malvaceae) is a plant that is widely recognised for its antihypertensive properties; however the constituent(s) responsible for this biological activity are presently unknown. The aim of this study was to identify the potential compounds that are responsible for the vasorelaxant activity of H. sabdariffa. Thereafter, the mechanisms involved in producing the vasorelaxation were investigated. The plant was extracted consecutively with hexane, ethyl acetate and methanol. The methanolic extract was subjected to bioassay-guided fractionation in order to isolate pure compounds that possessed vasorelaxant activity. The vascular effects of the pure compounds were studied on the rat aorta in vitro using myography techniques. Hibiscus acid produced a concentration-dependent relaxation of the rat aorta pre-contracted with either phenylephrine (3 μM) or KCl (60 mM), irrespective of the presence of the endothelium. When the tissue was pre-contracted with phenylephrine, the concentration required to produce 50% relaxation (IC50), was 0.09 ± 0.01 mg/ml. Hibiscus acid had no effect on the phasic contraction induced by phenylephrine in Ca2+-free physiological solution; but it did affect the component of the contraction that is due to Ca2+ influx. In parallel studies, garcinia acid, a diastereoisomer of hibiscus acid, was found to have an almost identical vasorelaxant effect. The vasorelaxant action of both compounds is most likely due to the inhibition of Ca2+ influx via voltage-dependent Ca2+ channels.Graphical abstractUnlabelled Image
       
  • Fusariumins C and D, two novel antimicrobial agents from Fusarium
           oxysporum ZZP-R1 symbiotic on Rumex madaio Makino
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Jianwei Chen, Xuelian Bai, Yi Hua, Huawei Zhang, Hong WangBioassay-guided fractionation of the crude extract of fermentation broth of one symbiotic strain Fusarium oxysporum ZZP-R1 derived from coastal plant Rumex madaio Makino, one traditional Chinese medicine used as a treatment of inflammation and toxication, yielded two novel compounds, fusariumins C (1) and D (2). Chemical structures of 1 and 2 were respectively determined as one meroterpene with cyclohexanone moiety and a sesquiterpene ester with a conjugated triene and an unusual oxetene ring by a combination of spectroscopic methods, including 1D and 2D NMR, mass spectrometry, and optical rotation analysis, as well as by comparison with literature data. Bioassay results indicated that compound 1 displayed potent activity against Staphyloccocus aureus with an MIC value of 6.25 μM, and compound 2 had a moderate inhibitory effect on S. aureus with an MIC value of 25.0 μM. It was the first report that phytochemical investigation of Fusarium strain from R. madaio Makino led to isolation of new antimicrobial agents.Graphical abstractUnlabelled Image
       
  • Synthesis, biological function and evaluation of Shikonin in cancer
           therapy
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Fangfang Wang, Xinsheng Yao, Youwei Zhang, Jinshan TangShikonin is a natural compound isolated from herbs and traditional medicines that have been used in a number of countries to treat various illnesses including inflammation, virus infection and cancer for centuries. Recent studies have shed light on the molecular mechanisms underlying these biological activities of Shikonin. Here we review the latest advances in our understanding of this compound class in the anti-cancer regimen. We focus on signaling pathways and cellular targets involved in the anticancer activity of Shikonin. We also briefly discuss approaches in evaluating the in vivo bioactivity and drug delivery of Shikonin in the anti-cancer treatment. Subsequently, we highlight recently developed strategies in the chemical and biogenic synthesis of Shikonin and summarize the structure-activity relationship studies of Shikonin. We anticipate that these lines of information would facilitate the functional identification and future clinical development of Shikonin and its derivatives in the combat against cancer.Graphical abstractUnlabelled Image
       
  • The Amaryllidaceae as a source of antiplasmodial crinane alkaloid
           constituents
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Jerald J. Nair, Johannes van StadenMalaria is prevalent in tropical and subtropical regions of the globe. With over 200 million cases reported annually, particularly in sub-Saharan Africa, it is an unnecessary burden to already overworked and ailing healthcare structures. Traditional medicine (TM) remains vibrant in most of these regions wherein plants often serve as the first line of defense against malaria. Given this fact as well as the successes elsewhere of therapies such as Artemisia annua emanating from evidence-based TM, interest in plants as a source of new antimalarial drugs has been rejuvenated. The bulbous plant family Amaryllidaceae is recognized for its structurally-diverse alkaloid constituents which exhibit interesting biological properties. This review focuses on the in vitro activities demonstrated by its crinane alkaloids against various strains of the malaria-causing parasite Plasmodium falciparum. The survey embraces the twelve genera of the Amaryllidaceae whose nineteen representative species have been examined for antiplasmodial crinane alkaloid principles. A total of seventy-two compounds were screened against nine strains of P. falciparum, with the α-crinanes reflecting better overall activities than their corresponding β-crinane subgroup congeners. In terms of potency, an ED50 of 0.14 μg/mL (for augustine in the D-6 strain) and IC50 of 0.35 μg/mL (for haemanthidine in the K1 strain) were the lowest activity indices observed. Structure-activity relationship studies afforded useful insight on the antiplasmodial pharmacophore and the features supporting its efficacy. Overall, crinane alkaloids have provided a useful platform for the study of antiplasmodial effects, not only in terms of potency but also in terms of structural diversity.Graphical abstractThe Amaryllidaceae as a source of antiplasmodial crinane alkaloid constituents. Jerald J. Nair, Johannes van Staden.Unlabelled Image
       
  • Naturally occurring cassane diterpenoids (CAs) of Caesalpinia: A
           systematic review of its biosynthesis, chemistry and pharmacology
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Wenhua Jing, XinXin Zhang, Hongxia Zhou, Ying Wang, Maoqiang Yang, Liping Long, Huiyuan GaoNatural products, especially diterpenoids, are enriched with numerous compounds with a broad spectrum of therapeutic indications, suggesting that functional moieties serve as a core pharmacophore. Cassane diterpenoids (CAs), as the main and characteristic constituents of medical plants in the Caesalpinia genus, have been widely studied due to their bioactivities, and>450 compounds have been reported since the 1960s, including 283 compounds that have been reported in the past decade. There are five main types of structures for these compounds: tricyclic cassane diterpenoids with a fused furan ring (I) or butanolide lactone (II), tricyclic cassane diterpenoids (III), norcassane diterpenoids (IV), and other types (V). CAs derivatives have a wide range of biological properties, including anti-inflammatory, antimalarial, antitumour, antiviral, antimicrobial, antinociceptive, and antioxidant effects. This review highlights the role of the biosynthetic pathway, including those with abnormal skeletons, as well as advances in structure, pharmacological activities and primarily mechanisms of CAs obtained from the Caesalpinia genus. The findings herein provide new insights into the development of this kind of natural diterpenoids.Graphical abstractUnlabelled Image
       
  • The anti-hyperglycemia effects of Rhizoma Coptidis alkaloids: A systematic
           review of modern pharmacological studies of the traditional herbal
           medicine
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Hang Ma, Kai He, Jianwei Zhu, Xuegang Li, Xiaoli YeHyperglycemia is a common endocrine system disease, which seriously affects people's health with a increasing morbidity in recent years. Rhizoma Coptidis (RC), one of the most commonly used traditional Chinese medicines, has been applied to treat diabetes in clinic for thousands of years. Since scientists demonstrated that alkaloids from RC owned the amazing anti-hyperglycemia activities 30 years ago, these compounds have been widely used for the treatment of diabetes and hyperglycemia with unconspicuous toxicities and side effects. With the help of molecular biology, immunology and other techniques, the mechanisms about anti-hyperglycemia effect of RC alkaloids have been extensively discussed. Numerous studies showed that RC alkaloids balanced the glucose homeostasis not only by widely recognizing insulin resistance pathways, but also by promoting insulin secretion, regulating intestinal hormones, ameliorating gut microbiota structures and many other ways. In this review, we combine the latest advances and systematically summarize the mechanisms of RC alkaloids in treating hyperglycemia and diabetic nephropathy to provide a deeper understanding of these natural alkaloids. In addition, the important role of gut microbiota associated with the glucose metabolism is also reviewed.Graphical abstractUnlabelled Image
       
  • Chemistry, bioactivities, extraction and analysis of azadirachtin:
           State-of-the-art
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Sara R. Fernandes, Luisa Barreiros, Rita F. Oliveira, Agostinho Cruz, Cristina Prudêncio, Ana Isabel Oliveira, Cláudia Pinho, Nuno Santos, Joaquim MorgadoAzadirachta indica A. Juss. (Neem) is an Indian tree recognized for its activity as pesticide, as well as several pharmacological properties. Among the various compounds already isolated and studied from Neem tree, azadirachtin (AZA) was identified as the main bioactive compound. Azadirachtin can be found at different parts of the Neem plant but assumes its maximum concentration at the seed level. This compound features a quite complex chemical structure, which justifies the 20-plus-year difficulty to identify the synthetic pathway that subsequently permitted to carry out its artificial synthesis. Azadirachtin is widely used as a basis for production of biopesticides; nevertheless, other properties have been recognized for this substance, among which the anticancer and antimalarial activity stand out. The methods available for azadirachtin extraction are diverse, including solid-liquid extraction and extraction with solvents at high or low temperatures. Alcohol based solvents are associated with higher extraction yields and are therefore preferred for the isolation of azadirachtin from plant parts. Clean-up of the extracts is generally required for further purification. The highest azadirachtin levels have been obtained from Neem seeds but concentration values present a large variation between batches. Therefore, in addition to extraction procedures, it is essential to establish routine methods for azadirachtin identification and quantification. Chromatography-based techniques are preferably selected for detection and quantification of azadirachtin in plant matrices. Overall, this process will guarantee a future reproducible, safe and effective use of the extracts in formulations for commercial applications.Graphical abstractUnlabelled Image
       
  • Possible clues for camptothecin biosynthesis from the metabolites in
           camptothecin-producing plants
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Xiang Pu, Cheng-Rui Zhang, Lin Zhu, Qi-Long Li, Qian-Ming Huang, Li Zhang, Ying-Gang LuoThe plant derived camptothecin (CPT) is a pentacyclic pyrroloquinoline alkaloid with unique antitumor activity. Successive discoveries of new CPT-producing plants occurred in recent years due to market demands. The scattered distribution among angiosperms drew researchers' attention. The aim of this review is to appraise the literature available to date for CPT distribution and the phytochemistry of these CPT-producing plants. Metabolite comparative analyses between the plants were also conducted for tracking of possible clues for CPT biosynthesis. Forty-three plant species in total were reported to possess CPT-producing capability, and one hundred twenty-five alkaloids classified into three major categories are summarized herein. Metabolite comparative analysis between these plants suggests the probability that the formation of the central intermediate for CPT biosynthesis has multiple origins. A more complete biogenetic reasoning for CPT and its structural homolog was delineated based on this fragmentary phytochemical evidence from a chemical point of view. Furthermore, an in-house compound database was constructed for further metabolomic analysis.Graphical abstractUnlabelled Image
       
  • Biological activity, phytochemistry and traditional uses of genus Lobelia
           (Campanulaceae): A systematic review
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Daniela G. Folquitto, Juliane N.D. Swiech, Camila B. Pereira, Vanessa B. Bobek, Gerusa C. Halila Possagno, Paulo V. Farago, Marilis D. Miguel, Juliana L. Duarte, Obdulio G. MiguelGraphical abstractUnlabelled Image
       
  • An anti-inflammatory C-stiryl iridoid from Camptosorus sibiricus
           Rupr.
    • Abstract: Publication date: April 2019Source: Fitoterapia, Volume 134Author(s): Fang Wang, Qing-Wen Jia, Zhen-Hai Yuan, Ling-Yue Lv, Min Li, Zhi-Bo Jiang, Da-Lian Liang, Dai-Zhou ZhangA new iridoid glycoside, named camptoside (1), together with three known compounds as dehydrodiconiferyl alcohol-9′-O-β-d-glucopyranoside (2), aesculetin (3) and vajicoside (4), have been isolated from Camptosorus sibiricus Rupr. (Aspleniaceae). Their structures were established on the basis of spectroscopic analysis, especially 1D- and 2D-NMR data, and by comparison of their spectroscopic and physical data with those reported in the literature. Compounds 1–3 exhibited inhibitions of nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages with IC50 values of 11.2, 8.3 and 9.4 μM, respectively.Graphical abstractUnlabelled Image
       
  • Zizhines G–O, AchE inhibitory meroterpenoids from Ganoderma
           sinensis
    • Abstract: Publication date: Available online 20 March 2019Source: FitoterapiaAuthor(s): Qi Luo, Wen-Wen Cao, Ze-Hong Wu, Shu-Mei Wang, Yong-Xian ChengAbstractZizhines G–O (1–9), nine new meroterpenoids, and seven known analogs (10–16) were isolated from the dried fruiting bodies of Ganoderma sinensis. Their structures were identified by using spectroscopic data and CD curve comparison. The inhibitory activities of the selected new meroterpenoids toward AchE were assessed in vitro. Compounds 1–6 and 10–14 were found to exhibit AchE inhibitory activities at the concentration of 50 μM.
       
  • Bioactive oxaphenalenone dimers from the fungus Talaromyces
           macrosporus
    KKU-1NK8
    • Abstract: Publication date: Available online 18 March 2019Source: FitoterapiaAuthor(s): Boonyanoot Chaiyosang, Kwanjai Kanokmedhakul, Wareerat Sanmanoch, Sophon Boonlue, Sarinya Hadsadee, Siriporn Jungsuttiwong, Somdej KanokmedhakulSix new polyketide-derived oxaphenalenone dimers, talaromycesone C (1) and macrosporusones A-E (2–6), together with eight known analogs, were isolated from the mycelium of the fungus Talaromyces macrosporus KKU-1NK8. Their structures were established based on their spectroscopic data and MS. The absolute configurations of new compounds 1–6 were determined by ECD analyses. Compounds 3 and 8 exhibited antimalarial activity against Plasmodium falciparum. Compound 3 showed activity against NCI-H187 cells, while compound 8 displayed activity against KB, MCF-7 and NCI-H187 cell lines. In addition, compound 11 showed antibacterial activity against Bacillus cereus, Staphylococcus aureus and MRSA.Graphical abstractUnlabelled Image
       
  • New coumarins and monoterpene galloylglycoside from the stem bark of
           Sapium baccatum
    • Abstract: Publication date: Available online 18 March 2019Source: FitoterapiaAuthor(s): Ting Li, Shanshan Wang, Peihong Fan, Hongxiang LouSapium baccatum has been traditionally used as therapeutic remedies. To support its medicinal benefits, our current phytochemical investigation attempted to further discover novel bioactive compounds from S. baccatum. Eight new phenolic compounds, namely, seven coumarins (1–7) and one monoterpene galloylglycoside (8), together with 23 (9–31) known compounds were isolated. Their structures were determined by extensive spectroscopic methods and comparison with literatures. The three pairs of enantiomers of 1, 2 and 7 were confirmed on the basis of HPLC chiral analysis, electronic circular dichroism data and optical rotations. Two coumarins (1–2) were proven to be artifacts through HPLC analysis. The inhibitory effects on TNF-α secretion were examined biologically in LPS-induced BV2 microglia cells and all of the tested compounds exhibited significant inhibitory activity, especially new compound 1 possessed stronger inhibitory effects compared to the positive control quercetin. In addition, compounds 14 and 15 showed weak antifungal activity against Candida albicans SC5314 with MIC values both at 64 μg/mL. The results laid a solid foundation for additional research on S.baccatum related to its anti-inflammatory and antifungal medicinal value.Graphical abstractUnlabelled Image
       
  • Semi-synthesis and structural elucidation of brevicanines A–D, four new
           C19-diterpenoid alkaloids with rotameric phenomenon from Aconitum
           brevicalcaratum
    • Abstract: Publication date: Available online 18 March 2019Source: FitoterapiaAuthor(s): Zhong-Sheng Wang, Wei Chen, Hai-Yue Jiang, Feng Gao, Xian-Li ZhouFour new C19-diterpenoid alkaloids brevicanines A–D (1–4) with rotameric phenomenon were isolated from Aconitum brevicalcaratum. They all possessed an unusual axial chiral phenyl-quinazoline side chain and their structures were elucidated by extensive spectroscopic analysis and chemical methods. Meanwhile, brevicanines A and B were semi-synthesized from their parent compound scaconine to further confirm their structures. Variable-temperature NMR spectroscopy was also used to investigate the atropisomers of brevicanine A, in which two sets of signals in 1H NMR spectra were observed at room temperature and coalesced over 140 °C. It's the first time to determine the atropisomeric preference of diterpenoid alkaloids.Graphical abstractUnlabelled Image
       
  • Adulteration of commercial grape seed extracts and other proanthocyanidins
           (PACs)-rich herbal extracts: Multi-compound HPLC profile patterns provide
           key to detection
    • Abstract: Publication date: Available online 18 March 2019Source: FitoterapiaAuthor(s): Suresh GovindaraghavanGraphical abstractA: Multi-batch signature HPLC fingerprint of GSE; B: HPLC fingerprint overlay of adulterated GSE 1 and 2 over signature GSE fingerprint and EIC 577:578 of adulterated GSE2. Inset: mass spectrum of marked peak in adulterated GSE 1.Unlabelled Image
       
  • Triterpenoid corosolic acid attenuates HIF-1 stabilization upon cobalt
           (II) chloride-induced hypoxia in A549 human lung epithelial cancer cells
    • Abstract: Publication date: Available online 18 March 2019Source: FitoterapiaAuthor(s): Mir Babak Bahadori, Somayeh Vandghanooni, Leila Dinparast, Morteza Eskandani, Seyed Abdulmajid Ayatollahi, Athar Ata, Hossein NazemiyehHypoxia-inducible factor-1 is a target for the management of cancer. Here, the anti-proliferation properties of corosolic acid (CA) against A549 human lung epithelial cancer cells in CoCl2-induced hypoxia is reported. CA was isolated from the roots of Salvia syriaca based on a bioassay-guided isolation platform and identified by 1D and 2D NMR experiments. Several cytotoxicity and genotoxicity analyses were performed using MTT, DAPI, cell cycle, DNA ladder, and annexin V/PI detection. Cobalt chloride (CoCl2) was used to stimulate hypoxia. The adaptation of A549 cells to a stimulated hypoxic condition in the presence of CA was evaluated. CA decreased the growth of A549 cells with an IC50 of 12 μg/mL at 48 h. Also, chromatin condensation and DNA fragmentation were detected as the sign of apoptosis occurrence. CA induced ~85% apoptosis and even 1% necrosis. The expression of hypoxia-inducible factor-1 α (HIF-1α), HIF-1β and downstream genes was strongly suppressed in the presence of CA in CoCl2-stimulated hypoxia condition. Results indicated that CA has remarkable cytotoxicity against cancerous cell in hypoxia condition and may be regarded for preparation of new formulations for possible uses as supplement and medicine in cancer therapy.Graphical abstractUnlabelled Image
       
  • Corrigendum to ‘Dimeric 2-(2-phenylethyl)chromones from the agarwood of
           Aquilaria crassna in Laos’[Fitoterapia 133 (2019) 12–16]
    • Abstract: Publication date: Available online 12 March 2019Source: FitoterapiaAuthor(s): Wei Li, Yang Yang, Wenhua Dong, Hao Wang, Fandong Kong, Caihong Cai, Wenli Mei, Haofu Dai
       
  • Isolation of yeast Ca2+ signal transduction inhibitors from the Early
           Cretaceous Burmese amber
    • Abstract: Publication date: Available online 8 March 2019Source: FitoterapiaAuthor(s): Takeshi Uchida, Hiroyuki Koshino, Junpei Abe, Mayuka Hakozaki, Hidetoshi Yamada, Ken-ichi KimuraTwo kinds of biologically active compounds were isolated from the MeOH extract of the Early Cretaceous Burmese amber [99 million years ago (Ma)], which is older than the K-Pg boundary. These compounds had inhibitory activity against the hypersensitive mutant yeast strain (zds1∆ erg3∆ pdr1∆ pdr3∆) with respect to Ca2+ signal transduction. They were identified as 16,17-bisnordehydroabietic acid (1) and 16,17-bisnorcallitrisic acid (2), respectively, on the basis of spectral analyses including HREIMS, 1D, and 2D NMR. Both have faint growth restoring activities around the clear inhibition zone against the mutant yeast on the 0.31–0.16 μg/spot. This is the first report of direct structural elucidation of 1 and 2 and the biologically active compounds derived from Burmese amber.Graphical abstractUnlabelled Image
       
  • Costatamins A – C, new 4-phenylcoumarins with anti-inflammatory activity
           from the Australian woodland tree Angophora costata (Myrtaceae)
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Ritesh Raju, Ahilya Singh, Frances Bodkin, Gerald MünchThe bioassay-guided isolation of new anti-inflammatory metabolites from the Australian Indigenous plant Angophora costata led to the discovery of three new 4-phenylcoumarins, costatamins A – C (1–3). The structures were determined by detailed spectroscopic analysis. Costatamins A – C were evaluated for their inhibitory effects on (a) NO production and (b) TNF-α release in RAW 264.7 macrophages, displaying an IC(50) value of 20–30 μg/mL for both the inflammatory markers.Graphical abstractUnlabelled Image
       
  • Ent-kauranes from the Chinese Excoecaria agallocha L. and NF-κB
           inhibitory activity
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Zhong-Ping Jiang, Bin-Hua Zou, Xiao-Juan Li, Jun-Jun Liu, Li Shen, Jun WuEleven undescribed ent-kauranes, named agallochanins A–K, were isolated from the stems and twigs of the Chinese semi-mangrove plant, Excoecaria agallocha L.. The absolute configurations of these diterpenoid compounds, except for the chirality of C-4 in agallochanin H, were unequivocally determined by HR-ESIMS, extensive NMR investigations, single-crystal X-ray diffraction analyses with Cu Kα radiation, quantum-chemical electronic circular dichroism (ECD) calculations, the comparison of experimental ECD spectra, and the modified Mosher's α-methoxy-α-(trifluoromethyl)phenylacetyl (MTPA) ester method. Agallochanins A–I are 3,4-seco-ent-kauranes. Agallochanin D represents the first example of 3,4-seco-17-nor-ent-kaurane. Agallochanin K exhibited NF-κB inhibitory activity with the inhibition rate of 79.6% at the concentration of 100.0 μM.Graphical abstractEleven undescribed ent-kauranes, named agallochanins A–K, were isolated and identified. Agallochanin K exhibited NF-κB inhibitory activity.Unlabelled Image
       
  • Gambogenic acid triggers apoptosis in human nasopharyngeal carcinoma
           CNE-2Z cells by activating volume-sensitive outwardly rectifying chloride
           channel
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Jingjing Su, Ting Xu, Genling Jiang, Mei Hou, Mengru Liang, Hui Cheng, Qinglin LiGambogenic acid (GNA) is one of the main components of Gamboge, and its anti-cancer effects have been well confirmed by previous researches. Nasopharyngeal carcinoma (NPC) has not been thoroughly studied, and the pathogenesis of NPC is unclear. Scientists have neither discovered effective therapies nor achieved a desirable prognosis. Some studies have found that the regulation of intra- and extracellular ion channels hinges directly on cell apoptosis, and treatment with GNA brings changes to the volume-sensitive outwardly rectifying chloride (VSOR Cl−) current of CNE-2Z cells recorded by the patch clamp method. Nevertheless, rarely have any researchers probed into the relevance between this variation and the anti-tumor mechanism of GNA. This paper is suggested that 2.0 μmol/L GNA activates VSOR Cl− currents on CNE-2Z cell membranes and that the activation of VSOR Cl− currents by GNA in CNE-2Z cells is blocked by the chloride channel blockers DIDS (400 μmol/L) and DCPIB (20 μmol/L). MQAE experiment further proves that GNA leads to the opening of chloride ion channel, which in turn results in the efflux of VSOR Cl− current; GNA induces the downregulation of GRP78 and the upregulation of ATF4 and CHOP proteins. These effects are correlated with endoplasmic reticulum (ER) stress. GNA can activate VSOR Cl− channels, leading to ER stress, inducing apoptosis and inhibiting proliferation in CNE-2Z cells.Graphical abstractUnlabelled Image
       
  • Three new hopane-type triterpenoids from the aerial part of Adiantum
           capillus-veneris and their antimicrobial activities
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Xia Zhang, Hai-Li Chen, Liu Hong, Lu-Lin Xu, Xiao-Wei Gong, Dong-Lai Zhu, Xiao-Hua Xu, Wei Zhao, Fei Wang, Xiao-Long YangThree new hopane-type triterpenoids (1–3), fern-7(8)-en-19α, 28-diol (1), pteron-14-ene-7α,19α,28-triol (2) and 3β,4α,25-trihydroxyfilican (3), were isolated from the aerial parts of Adiantum capillus-veneris. Their structures were determined by NMR spectroscopic and mass spectrometric data. Compounds 2 and 3 exhibited remarkable antifungal activity against Helminthosporium maydis and Alternaria alternata with MIC values of 12.5–3.125 μg/mL, and compound 3 also against Verticillium dahliae Kleb with an MIC value of 3.125 μg/mL. In addition, compounds 1–3 also displayed weak antibacterial activity against Micrococcus lysodeikticus, Bacterium paratyphosum B and Pseudomonas aeruginosa with an MIC value of 100 μg/mL.Graphical abstractUnlabelled Image
       
  • Discovery of potent indoleamine 2,3-dioxygenase (IDO) inhibitor from
           alkaloids in Picrasma quassioides by virtual screening and in vitro
           evaluation
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Ning Wang, Jie Zhang, Qiao Li, Hui Xu, Geng Chen, Zhiyong Li, Difa Liu, Xin YangIndoleamine 2,3-dioxygenase (IDO) is one of the important targets for cancer immunotherapy through tryptophan pathway. Recently it has being paid great attention to search potent and safe IDO inhibitor from small-molecule compounds. Picrasma quassioides is a kind of medicinal plant abundant with tryptophan-derived indole alkaloids. By virtual screening and kinetic method for enzymatic analysis, lead compounds with potential IDO inhibitory activity were discovered for the first time from PQAs, the natural alkaloids in Picrasma quassioides. The results based on molecular docking analysis and structure-activity relationship (SAR) study demonstrated that coordinating with ferrous ion on the active site of IDO has a great impact on the inhibition potency, and β-carboline with carboxyl substituted on C-1 is the key pharmacophore for IDO inhibition of PQAs. Enzymatic assay provided further evidence for the effectiveness of β-carboline-1-carboxylic acid, which displayed as the most potent competitive inhibitor of IDO among these PQAs, and is even more potent than the recognized positive control 1-methyl tryptophan. This natural tryptophan-derived alkaloid thus deserved further deep research as a promising IDO modulator for cancer immunotherapy.Graphical abstractUnlabelled Image
       
  • Hirtellina lobelii DC. essential oil, its constituents, its combination
           with antimicrobial drugs and its mode of action
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Madona Khoury, Marc El Beyrouthy, Naïm Ouaini, Véronique Eparvier, Didier StienWith the goal of unravelling antimicrobial agents and mixtures inspired by plant defences, we investigated the antibacterial and antifungal efficacy of Hirtellina lobelii DC. essential oil (EO), both alone and in combination with antimicrobial drugs.Hirtellina lobelii DC. EO was analysed by GC, GC–MS and partial fractionation/NMR. It was essentially composed of oxygenated sesquiterpenes (75.2%), with α-bisabolol (34.5%), fokienol (12.0%) and T-muurolol (6.8%) serving as the main components. Microbial susceptibility was determined by the broth microdilution method and was expressed as minimum inhibitory concentration (MIC) and minimum bactericidal or fungicidal concentration (MBC or MFC). This EO was found to possess remarkable bactericidal (MBC/MIC = 2) and fungicidal (MFC/MIC = 1–4) potential, particularly against the Gram (+) bacteria Staphylococcus aureus, including its methicillin-resistant forms, the yeast Cryptococcus neoformans and dermatophytes from the genus Trichophyton (MICs 8–128 μg/ml). The examination of the combined effects of the EO with antimicrobial drugs revealed synergisms of the EO with vancomycin against S. aureus and of the EO with fluconazole and griseofulvin against dermatophytic fungi (FICI 0.2–0.5). The effect of H. lobelii EO on the morphologies of fungal hyphae and bacteria, as determined by scanning electronic microscopy (SEM), showed fungal hyphae swelling and bulging.These results suggest that H. lobelii EO and its major constituent, α-bisabolol, have remarkable antimicrobial potential. Combination therapies of this EO with antifungal drugs could offer a promising alternative for treatment of human mycoses caused by filamentous dermatophytic fungi.Graphical abstractUnlabelled Image
       
  • Two pairs of enantiomeric propylated flavonoids and a new lignan from the
           aerial parts of Abrus precatorius
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Yan Li, Xu-Bing Qin, Hong-Xin Liu, Zhi-Fang Xu, Hai-Bo Tan, Sheng-Xiang QiuTwo pairs of novel enantiomeric flavonoids (1a, 1b and 2a, 2b), along with one new lignan (3), were isolated from the aerial parts of Abrus precatorius. All of these enantiomeric flavonoids featured an unprecedented propylated flavonoid skeleton representing a new family of flavonoid, and the new lignan was found to have an attractive arachidate ester side chain. Their structures were extensively elucidated by means of detailed NMR and mass spectroscopic analysis. Moreover, biological evaluation of antibacterial activity for these compounds against Bacillus cereus and Escherichia coli were conducted.Graphical abstractUnlabelled Image
       
  • Two new meroterpenoids and two new monoterpenoids from the deep
           sea-derived fungus Penicillium sp. YPGA11
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Zhongbin Cheng, Wei Xu, Yanyan Wang, Shangyuan Bai, Lijun Liu, Zhuhua Luo, Wangjun Yuan, Qin LiTwelve terpenoids, including two new 3,5-dimethylorsellinic acid-based meroterpenoids (1 and 2) and two new monoterpenoids (11 and 12), were obtained from the deep-sea fungus Penicillium sp. YPGA11. Their structures were determined by extensive analyses of spectroscopic data, and the absolute configurations of 1 and 2 were determined by comparisons of experimental and calculated ECD spectra. Compounds 1 and 2, bearing a 23-aldehyde or 23-carboxylic acid group, were rarely found in compounds with similar carbon skeleton. All compounds but 11 were evaluated for inhibitory effects towards nitric oxide production induced by lipopolysaccharide in RAW 264.7 macrophage cells. Compound 9 exhibited significant inhibitory effects with an IC50 value of 7.58 μM, being comparable to the positive control, quercetin (10.97 μM).Graphical abstractUnlabelled Image
       
  • New compounds of Siolmatra brasiliensis and inhibition of in vitro protein
           glycation damage
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Carlos Henrique Corrêa dos Santos, Tassiana Cristina Talpo, Bruno Pereira Motta, Anderson Kiyoshi Kaga, Amanda Martins Baviera, Rosane Nora Castro, Virgínia Cláudia da Silva, Paulo Teixeira de Sousa-Junior, Ludger Wessjohann, Mário Geraldo de CarvalhoTwenty compounds were isolated from the hydroethanolic extract of the stems of Siolmatra brasiliensis, five flavonoids, two lignans, one glucosyl phytosterol, seven nor-cucurbitacins, one new phenolic derivative named siolmatrin (1) and four new dammarane-type saponins named siolmatrosides II-V (2–5), the structures of the compounds were assigned by means of 1D and 2D NMR experiments and HRESIMS of the natural compounds and some acetyl derivatives. The effects of the crude hydroethanolic extract (SbExt) and the ethyl acetate fraction (SbEtAc) of Siolmatra brasiliensis stems on the formation of advanced glycation end-products (AGEs) were also investigated. In the in vitro model system of protein glycation using bovine serum albumin (BSA) and glucose, addition of SbExt or SbEtAc inhibited the formation of fluorescent AGEs, in parallel to minor levels of fructosamine (SbEtAc) and markers of tyrosine and tryptophan oxidation (SbExt and SbEtAc). Protein crosslinking, which represents changes of late stages of protein glycation, was reduced in the presence of SbExt and SbEtAc. Siolmatra brasiliensis stems seem to be a promising source of compounds having ability to prevent glycoxidation changes, arising as an interesting option to be studied as a complementary therapy for complications of diabetes.Graphical abstractUnlabelled Image
       
  • Gossypol inhibits 5α-reductase 1 and 3α-hydroxysteroid dehydrogenase:
           Its possible use for the treatment of prostate cancer
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Shuyan Cao, Guimin Wang, Fei Ge, Xiaoheng Li, Qiqi Zhu, Ren-Shan Ge, Yunshan WangGossypol is a yellow polyphenol isolated from cotton seeds. It has the antitumor activity and it is being tested to treat prostate cancer. However, its underlying mechanisms are still not well understood. The present study investigated the inhibitory effects of gossypol acetate on rat 5α-reductase 1, 3α-hydroxysteroid dehydrogenase, and retinol dehydrogenase 2 for androgen metabolism. Rat 5α-reductase 1, 3α-hydroxysteroid dehydrogenase, and retinol dehydrogenase 2 were expressed in COS-1 cells. Immature Leydig cells that contain these enzymes were isolated from 35-day-old male Sprague Dawley rats. The potency and mode of action of gossypol acetate to inhibit these enzymes in both enzyme-expressed preparations and immature Leydig cells were examined. Molecular docking study of gossypol on the crystal structure of 3α-hydroxysteroid dehydrogenase was performed. Gossypol acetate inhibited 5α-reductase 1 and 3α-hydroxysteroid dehydrogenase with IC50 values of 3.33 ± 0.07 and 0.52 ± 0.06 × 10−6 M in the expressed enzymes as well as 8.512 ± 0.079 and 1.032 ± 0.068 × 10−6 M in intact rat immature Leydig cells, respectively. Gossypol acetate inhibited rat 5α-reductase 1 in a noncompetitive mode and 3α-hydroxysteroid dehydrogenase in a mixed mode when steroid substrates were supplied. Gossypol acetate weakly inhibited retinol dehydrogenase 2 with IC50 value over 1 × 10−4 M. Molecular docking analysis showed that gossypol partially bound to the steroid-binding site of the crystal structure of rat 3α-hydroxysteroid dehydrogenase. Gossypol acetate is a potent inhibitor of rat 5α-reductase 1 and 3α-hydroxysteroid dehydrogenase, possibly inhibiting the formation of androgen in the prostate cancer cells.Graphical abstractUnlabelled Image
       
  • Flueggenoids A – E, new dinorditerpenoids from Flueggea
           virosa
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Xiao-Feng Wang, Fei-Fei Liu, Zhengdan Zhu, Qiang-Qiang Fang, Shi-Jin Qu, Weiliang Zhu, Li Yang, Jian-Ping Zuo, Chang-Heng TanA phytochemical investigation on the twigs and leaves of Flueggea virosa (Euphorbiaceae) led to the isolation of flueggenoids A – E (1–5), five new 13-methyl-ent-podocarpanes, together with eleven known compounds (6–16). Their structures and absolute configurations were elucidated on the basis of extensive MS and NMR data analysis, and/or single-crystal X-ray diffraction, time-dependent density functional theory (TDDFT)-based electronic circular dichroism (ECD) calculations, and chemical transformation. All isolates were evaluated for anti-HCV activity, the results showed that terpenoids of F. virosa had nonnegligible contribution for the anti-HCV activity.Graphic abstractUnlabelled Image
       
  • Metabolites identification of (+)-usnic acid in vivo by
           ultra-high-performance liquid chromatography coupled with quadrupole
           time-of-flight mass spectrometry
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Ludan Hou, Yiran Jin, Wenjing Sun, Shuai Guan, Huijun Xu, Qiao Wang, Lantong Zhang, Yingfeng Du(+)-usnic acid (UA) is an active natural phenolic acid ingredient originating from Chinese traditional Tibetan herb. Usnea acid is expected to become a new agent for anticancer and remarkable antitumor. To reveal its metabolic profile, metabolites identification of UA in vivo was studied using ultra-high-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UHPLC-Q-TOF-MS/MS) in this present study. The chromatographic separation was performed on a C18 column with a mobile phase consisted of methanol and water with a flow rate of 0.4 ml/min. The mass spectral analysis conducted in a negative electrospray ionization mode combined with information-dependent acquirement technology (IDA) was used to trace all the potential UA metabolites. Several sensitive and specific multiple data-mining techniques especially key product ions (KPIs) filter were applied to hunt and identify metabolites rapidly. As a result, a total of 36 metabolites were detected after oral administration of UA, including 33, 8 and 16 in rat urine, plasma and bile, respectively. These results showed that the probable metabolite pathways of UA were oxidation, reduction, dihydroxylation, glycine conjugation, glucuronide conjugation, N-acetylcysteine conjugation and methylation. It is the first time to elucidate the profile of UA in vivo. These results not only provided the basis of UA pharmacological properties, but also gave the guidance in clinical medication. Moreover, the analysis strategy and methodology proposed in this paper could be widely used in characterization of other phenolic acids metabolites.Graphical abstractUnlabelled Image
       
  • Pyrone derivatives from Helichrysum italicum
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Julia Werner, Weaam Ebrahim, Ferhat Can Özkaya, Attila Mándi, Tibor Kurtán, Mona El-Neketi, Zhen Liu, Peter ProkschChemical investigation of aerial parts of Helichrysum italicum yielded two new pyrone derivatives (1 and 2) along with ten known compounds. The structures of the new compounds were established by 1D and 2D NMR spectra as well as by HRESIMS data. Compound 1 represented a rare dimer of substituted α- and γ-pyrone units. DFT-NMR and TDDFT-ECD calculations were carried out to determine the absolute configuration of 1 but failed, representing the limitation of TDDFT-ECD calculation for the configurational assignment. All compounds were measured for their antibacterial and cytotoxic activity but proved to be inactive.Graphical abstractUnlabelled Image
       
  • Cytotoxic limonoids from the bark of Walsura cochinchinensis
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Binh T.D. Trinh, Hiep D. Nguyen, Hieu T. Nguyen, Phuoc D. Pham, Ngoc T.N. Ngo, Le-Thu T. Nguyen, Ly T.T. Nguyen, Dzung N. Bui, Son V. Dang, Lien-Hoa D. NguyenThree new limonoids, walsucochinones A-C (1–3), along with eight known compounds, were isolated from an ethyl acetate extract of the bark of Walsura cochinchinensis. Their structures were determined using spectroscopic techniques, mainly 1-D and 2-D NMR. The ethyl acetate extract showed cytotoxic activity against MCF-7 human breast cancer cells and cytotoxicity of the isolated compounds were evaluated in vitro using the SRB assay. Walsucochinone C (3) exhibited the most active effect with IC50 value of 16.4 ± 0.2 μM.Graphical abstractUnlabelled Image
       
  • Three new capnosane-type diterpenoids from the South China Sea soft coral
           Lobophytum sp.
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Quan Zhang, Xu-Wen Li, Li-Gong Yao, Bin Wu, Yue-Wei GuoThree new diterpenoids with an unusual capnosane skeleton named lobophytrols A–C (1–3) were isolated from the South China Sea soft coral Lobophytum sp. along with one known related diterpene, (11S,12S,1E,3E,7E)-11,12-epoxycembra-1,3,7-triene (7). Their structures were elucidated on the basis of spectroscopic analysis and by comparison with those reported in the literature.Graphical abstractUnlabelled Image
       
  • A new byciclic monoterpene glucoside and a new biflavone from the male
           reproduction organs of Wollemia nobilis
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Alessandro Venditti, Claudio Frezza, Giacomo Rossi, Ilaria Serafini, Alessandro Ciccòla, Fabio Sciubba, Sebastiano Foddai, Lamberto Tomassini, Armandodoriano Bianco, Mauro SerafiniIn this work, the fifth part of an ongoing phytochemical study on Wollemia nobilis was reported. The attention was now focused on the male reproduction organs of which the content in both primary and secondary metabolites was analyzed. Twenty compounds, belonging to seven different classes of natural compounds, were identified from the ethanolic extract by means of Column Chromatography and NMR and MS Spectroscopy. They all represent new compounds for the studied organ whereas some of them are also new constituents of the genus or even previously undescribed phytochemicals. Their presence was able to display a general overview of these organs from the phytochemical standpoint and to provide more elements in confirmation with the current botanical classification of the species. Moreover, they add a further experimental evidence of the tendency of this species to accumulate different metabolites in different organs. This characteristic as well as the occurrence of several compounds with added value, make this plant a possible candidate for large scale cultivation with extractive purposes to obtain useful phytochemicals for botanicals and pharmaceutical fields. Moreover, they offer the opportunity to develop an additional method of conservation and protection for this endangered and very rare species.Graphical abstractUnlabelled Image
       
  • Cytotoxic and antibacterial triterpenoids from the roots of Morinda
           officinalis var. officinalis
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Hui-Juan Zhai, Jin-Hai Yu, Qianqian Zhang, Hai-Shan Liu, Jun-Sheng Zhang, Xiu-Qing Song, Yuying Zhang, Hua ZhangSeven new pentacyclic triterpenoids including six ursane-type, marinoids A–F (1–6), and one oleanane-type, marinoid G (7), along with five known analogues (8–12), were separated from the roots of Morinda officinalis var. officinalis. Their structures were assigned by spectroscopic means especially analysis of 2D NMR data, with the absolute configurations of 1 and 2 being determined via comparison of their experimental ECD spectra with the computed ones. Selective compounds displayed cytotoxic activity against two human osteosarcoma cell lines and also antibacterial effects against one Gram positive and one Gram negative strains.Graphical abstractUnlabelled Image
       
  • Amino acid-sesquiterpene lactone conjugates from the aerial parts of
           Centaurea pungens and evaluation of their antimicrobial activity
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Fatiha Labed, Milena Masullo, Virginia Mirra, Filomena Nazzaro, Fadila Benayache, Samir Benayache, Sonia PiacenteTwo new amino acid-sesquiterpene lactone conjugates, named centaureolide A (1) and centaureolide B (2) along with a germacrane derivative (3), five flavonoids (4–8) and one quinic acid derivative (9) have been isolated from the aerial parts of Centaurea pungens (Asteraceae). Their structures were established by a combination of one- and two-dimensional NMR techniques, and mass spectrometry. The never reported sesquiterpene lactones have been determined as germacrane derivatives (1 and 2) characterized by the unusual occurrence of a proline moiety. In order to validate the use of the extract of C. pungens in folk medicine, the antimicrobial activity of the isolated compounds against the Gram-positive strains Bacillus cereus, Staphylococcus aureus and Listeria innocua and the Gram-negative strains Pseudomonas aeruginosa and Pseudomonas fragi was evaluated.Graphical abstractUnlabelled Image
       
  • homo-Adamantane type polycyclic polyprenylated acylphloroglucinols from
           Hypericum hookerianum
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Ye Ye, Xing-Wei Yang, Yan Zhou, Gang XuHookeriones I–Q (1–9), nine new homo-adamantane type polycyclic polyprenylated acylphloroglucinols (PPAPs), were isolated from Hypericum hookerianum, along with twenty known analogues. These structures were determined on the basis of comprehensive NMR and MS spectroscopic data. Comprehensive analysis of the NMR data revealed the correlations between the configuration of H-18 and H-28 and the chemical shifts of related signals. The cytotoxicity and anti-allergic activities of the new isolates were evaluated, and several ones exhibited moderate cytotoxicity against ECA-109 cell lines.Graphical abstractUnlabelled Image
       
  • Lignans with melanogenesis effects from Premna serratifolia wood
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): So-Yeun Woo, Shotaro Hoshino, Chin Piow Wong, Nwet Nwet Win, Maurice Ducret Awouafack, Prema, Hla Ngwe, Huiping Zhang, Fumiaki Hayashi, Ikuro Abe, Hiroyuki MoritaThree new lignoids, premnan A (1), premnan B (2), and tauntangyiol C (3), were isolated from Premna serratifolia wood, a traditional cosmetic plant in Myanmar, together with a new lignoid, premnan C (4) assumed to be an artifact, one natural new lignoid (5), and three known lignoids (6–8). The structures of the new compounds 1–4 were elucidated based on 1D and 2D NMR, IR spectroscopy, and HRESIMS. The absolute configurations of 1–4 were also determined by optical rotation, circular dichroism (CD) data analyses, and comparisons with the reported literature. All isolated compounds were tested for their melanogenesis activities against the B16-F10 mouse melanoma cell line. Compounds 1 and 4 showed melanogenesis enhancing activities of 31% and 50%, respectively, at a 50 μM concentration. Compounds 2, 3, and 6 increased melanin production by 67%, 30%, and 45%, respectively, at a 100 μM concentration, without any cytotoxicity.Graphical abstractUnlabelled Image
       
  • Diverse epoxy grayanane diterpenoids with analgesic activity from the
           roots of Pieris formosa
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Chang-Shan Niu, Yong Li, Yun-Bao Liu, Shuang-Gang Ma, Xiao-Jing Wang, Fei Liu, Sheng Liu, Jing Qu, Shi-Shan YuIn our on-going study to investigate components with analgesic activity, eight new grayanane diterpenoids, epoxypieristoxins A–H (1–8), along with one known compound (9) were isolated from the roots of Pieris formosa. Their structures with absolute configurations were characterized by a series of spectroscopic methods and X-ray diffraction. Notably, compounds 1–5 represented the first example of natural grayanane diterpenoids possessed a 10,14-epoxy group. Whereas, compounds 6–7 were the first example of grayanane diterpenoid with a 7,10-epoxy group. Biological assays showed that compounds 1–3 and 5–8 displayed significant analgesic activity at a dose of 5.0 mg/kg (ip) compared to the vehicle tests (p 
       
  • An indirect competitive enzyme-linked immunosorbent assay toward the
           standardization of Pueraria candollei based on its unique isoflavonoid,
           kwakhurin
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Gorawit Yusakul, Rui Togita, Kei Minami, Kaskamol Chanpokapaiboon, Thaweesak Juengwatanatrakul, Waraporn Putalun, Hiroyuki Tanaka, Seiichi Sakamoto, Satoshi MorimotoKwakhurin (Kwa) is a plant secondary metabolite solely present in Pueraria candollei var. mirifica (P. candollei), which has long been used as a Thai traditional herb for estrogen replacement therapy. Recently, health hazards have arisen in Japan regarding P. candollei-derived products containing potent estrogenic compounds. Therefore, the development of standardization methods for P. candollei materials is an urgent problem requiring resolution. The enzyme-linked immunosorbent assay (ELISA) is an effective analytical technique because it enables the development of sensitive and specific assays of the target compound through antigen−antibody reaction. Here, we produced a monoclonal antibody against Kwa (MAb 11F) by immunizing Kwa-bovine serum albumin (BSA) conjugates prepared using an N,N′-carbonyldiimidazole (CDI) mediated method. Stability and cross-reactivity tests of MAb 11F revealed that the MAb 11F is stable for at least 4 months at 4 °C and is highly specific to Kwa. The detectable concentration range of an indirect competitive ELISA (icELISA) using MAb 11F exhibited values of 1.53–48.8 ng/mL with the limit of detection (LOD) of 1.13 ng/mL. Validation analyses revealed that the developed icELISA is precise, accurate, and reliable enough to be applied to P. candollei-derived samples and products for their standardization.Graphical abstractUnlabelled Image
       
  • Coumarinolignoids and lignanoids from the stems and leaves of Sapium
           discolor
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Yong-Li Zhang, Qi-Min Pan, Hai-Bing Liao, Jiang-Ke Qin, Ning Li, Dong Liang, Gui-Jie ZhangTwo new coumarinolignoids, sapiumins D (1) and E (2), a new lignanoid, lariciresinol 9′-benzoate (3), together with six known coumarinolignoids (4–9) and eight known lignanoids (10–17), were isolated from the stems and leaves of Sapium discolor. The structures of the isolated compounds were elucidated by extensive spectroscopic methods, including NMR, MS, and single crystal X-ray diffraction experiments. Compounds 5, 10, 11, and 13 significantly inhibited nitric oxide production in lipopolysaccharide-induced BV-2 microglial cells, with IC50 values in the range of 2.13–11.37 μM.Graphical abstractUnlabelled Image
       
  • Dimeric 2-(2-phenylethyl)chromones from the agarwood of Aquilaria
           crassna
    in Laos
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Wei Li, Yang Yang, Wenhua Dong, Hao Wang, Fandong Kong, Caihong Cai, Wenli Mei, Haofu DaiFour new dimeric 2-(2-phenylethyl)chromones (1–4) were isolated from the agarwood of Aquilaria crassna in Laos. All structures were determined based on extensive spectroscopic methods including IR, UV, 1D and 2D NMR, ECD, and HRMS. The structures of compounds 1–3 were characterized by two C-O-C linkages between the two chromone moieties, while compound 4 featured one C-O-C linkage and one CC bond connecting with two chromone moieties. Compounds 1 and 3 showed weak cytotoxicity against human hepatocellular carcinoma BEL-7402 cell line with IC50 values of 44.68 and 42.10 μΜ.Graphical abstractThe structures of four new compounds and the sample of agarwood agarwood of Aquilaria crassna in Laos.Unlabelled Image
       
  • Sesquiterpenoids and triterpenoids from Secamone lanceolata blume with
           inhibitory effects on nitric oxide production
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Panpan Yang, Wanfang Zhu, Jian Xu, Wenyuan Liu, Zhenhuan Dong, Takashi Kikuchi, Takeshi Yamada, Ning Xie, Feng Feng, Jie ZhangFive previously undescribed sequiterpenoids, including three guaiane sesquiterpenoids secamonol A (2), secamonester (3), secamonether (4), and one elemanolide sequiterpenoid secamonol B (7), and one eudesmane sesquiterpenoid secamonol C (8) along with nine known compounds were isolated from Secamone lanceolata Blume. Their structures and absolute configurations were established by analyzing of NMR, CD, MS spectrum and single-crystal X-ray diffraction, as well as comparing with the literatures. Compounds 1 and 4–8 exhibited potential inhibition activities of NO production with IC50 values in the range of 27.9–57.5 μM with no obvious cytotoxicities even at the high concentration (100 μM). Whereas, compound 3 showed significant cytotoxicity with CC50 value of 5.6 μM against macrophages RAW264.7 Cells.Graphical abstractUnlabelled Image
       
  • Antibacterial anthraquinone dimers from marine derived fungus
           Aspergillus sp
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Jian Lin Li, Xin Jiang, Xinpei Liu, Caiwei He, Yuxin Di, Saijian Lu, Huilian Huang, Bin Lin, Dong Wang, Boyi FanAs a continue investigation of the bioactive secondary metabolites from marine derived fungi, two new anthraquinone dimers (1, 2), along with three known anthraquinones (3–5) and two known xanthones (6, 7) were isolated from the marine-derived fungus Aspergillus versicolor. Their structures, including the absolute configurations, were elucidated by NMR, HRMS, and comparison with reported ones. Among them, compounds 1 and 2 were identified as anthraquinone dimers which dimerized by a rare C-O-C ether linkage, and both of them showed selective antibacterial activity against Gram-positive Staphylococcus aureus; whilst compound 6 exhibited moderate cytotoxicity against human cancer cell lines.Graphical abstractUnlabelled Image
       
  • Study of antiopisthorchiasis activity of sesquiterpene lactones and their
           derivatives
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): S.M. Adekenov
       
  • Graphical abstract TOC
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s):
       
  • Seven new neuroprotective sesquineolignans isolated from the seeds of
           Crataegus pinnatifida
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Zhuo-Yang Cheng, Li-Li Lou, Pei-Yuan Yang, Xiao-Yu Song, Xiao-Bo Wang, Xiao-Xiao Huang, Shao-Jiang SongThe investigation of the ethanol extract of the seeds of Crataegus pinnatifida led to the isolation of seven new 8-O-4′ type sesquineolignans crasesquineolignan A–G (1–7), along with a reported analogue, leptolepisol B (8). The chemical structures of these compounds were elucidated based on complex analysis of their MS, 1D and 2D NMR data. All the isolated compounds were tested for their neuroprotective effects against the damage of human neuroblastoma SH-SY5Y cells induced by H2O2, and most of them showed significant neuroprotective activity. Among them, compound 4 (77.58%) showed the best protective effect, even better than the positive control (69.26%) at 25 μM.Graphical abstractUnlabelled Image
       
  • Seven new guanacastane-type diterpenoids from the fungus Verticillium
           dahliae
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Hong Zhang, Ming-Hua Yang, Yun Li, Xiao-Bei Cheng, Yue-Hu Pei, Ling-Yi KongSeven new guanacastane-type diterpenoids, namely dahlianes E-K (1–7), and three known ones (8–10) were isolated from the cultures of the fungus Verticillium dahliae. Their structures were established by extensive spectroscopic data analysis along with Rh2(OCOCF3)4- and Mo2(OAc)4-induced electronic circular dichroism (ECD) experiment. Dahliane G showed an 80-fold potentiation effect on the sensitization of doxorubicin at the concentration of 15 μM when screening the reversal activity on doxorubicin-resistant human breast cancer cells (MCF-7/DOX).Graphical abstractUnlabelled Image
       
  • Lewis acid-mediated skeleton transformation of Euphorbia diterpenes: From
           lathyrane to euphoractane and myrsinane
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Jia-Xi Wang, Ling-Li Zheng, Feng Gao, Xian-Li ZhouNatural euphoractane and myrsinane diterpene skeletons, together with an unnatural 5/7/7/4 fused-ring diterpene skeleton were furnished via BF3·Et2O-mediated transformation of lathyrane-type diterpene, Euphorbia factor L1. The skeleton transformation process was mainly involved in the cascade oxirane-opening (cyclopropane-opening)/oxe-Micheal addition reaction. The structures of three diterpenes were confirmed by comprehensive spectra analysis and single crystals X-ray diffraction. Current results proved the biogenesis pathway between lathyrane with euphoractane and myrsinane by chemical transformation for the first time.Graphical abstractUnlabelled Image
       
  • Furoquinolines and dihydrooxazole alkaloids with cytotoxic activity from
           the stem bark of Araliopsis soyauxii
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Blaise Kemajou Nganou, Armelle T. Mbaveng, Serge A.T. Fobofou, Aimé G. Fankam, Gabin Thierry M. Bitchagno, James D. Simo Mpetga, Ludger A. Wessjohann, Victor Kuete, Thomas Efferth, Pierre TaneTwo new furoquinoline alkaloids, maculine B (1) and kokusaginine B (2) and one new dihydrooxazole alkaloid, veprisazole (3), along with four known compounds namely, N13-methyl-3-methoxyrutaecarpine (4), flindersiamine (5), skimmianine (6) and tilianin (7) were isolated from the methanol extract of the stem bark of Araliopsis soyauxii Engl. by various chromatographic methods. Their structures were determined using spectrometry and spectroscopic techniques including NMR and MS. The cytotoxicity of the new compounds compared to that of doxorubicin, the reference anticancer compound, was determined on a panel of nine cancer cell lines including sensitive and drug resistant phenotypes. The three previously undescribed alkaloids displayed selective activities. Maculine B (1), the most active one among the newly described compounds, exhibited IC50 below 30 μM against CCRF-CEM leukemia and U87MG glioblastoma cells.Graphical abstractUnlabelled Image
       
  • Eight new triterpenoid saponins with antioxidant activity from the roots
           of Glycyrrhiza uralensis Fisch
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Yuan-Yuan Liu, Ya-Nan Yang, Zi-Ming Feng, Jian-Shuang Jiang, Pei-Cheng ZhangEight new triterpenoid saponins (1–8), were isolated from the roots of Glycyrrhiza uralensis Fisch., together with 10 known triterpenoid saponins (9–18). Their structures were determined by analysis of their spectroscopic data and comparison with the reference. All of the compounds were evaluated for their antioxidant effects in the in vitro assay. Compounds 2 and 8 showed significant antioxidant activities against Fe2+/cysteine-induced liver microsomal lipid peroxidation at 0.1 μM.Graphical abstractUnlabelled Image
       
  • Aquilariaenes A-H, eight new diterpenoids from Chinese eaglewood
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Lin Yang, Peiyi Guo, Aijing Liu, Songyang Sui, Sha Shi, Shunxing Guo, Jungui DaiAquilariaenes A-H (1–8), eight new diterpenoids and nor-diterpenoids (1–8) belonging to abietane or pimarane, were isolated from the petroleum ether extract of Chinese eaglewood. Their structures were elucidated on the basis of extensive spectroscopic methods including HRESIMS, IR, 1D and 2D NMR spectroscopic data analyses. Antidepressant activities of isolates for in vitro inhibition of serotonin and norepinephrine reuptake in rat brain synaptosomes were evaluated.Graphical abstractUnlabelled Image
       
  • Melosuavine I, an apoptosis-inducing bisindole alkaloid from Melodinus
           suaveolens
    • Abstract: Publication date: March 2019Source: Fitoterapia, Volume 133Author(s): Zhong-Ying Fang, Yi-Dan Ren, Si-Yu Du, Miao Zhang, Yun-Shan Wang, Lei Fang, Hua ZhangA new bisindole alkaloid, melosuavine I (1) possessing an aspidosperma-aspidosperma dimeric skeleton, was isolated from the leaves of Melodinus suaveolens. The structure with absolute configuration of 1 was elucidated by a combination of MS, NMR and computational methods. MTT assays indicated that 1 exhibited significant cytotoxicity on human breast cancer BT549 cells with an IC50 value of 0.89 μM. Further study showed that 1 inhibited BT549 cell proliferation by inducing apoptosis through activation of caspase 3 and p53, and down-regulation of Bcl-2.Graphical abstractUnlabelled Image
       
  • New sesquiterpenoids from the stems of Datura metel L.
    • Abstract: Publication date: Available online 27 February 2019Source: FitoterapiaAuthor(s): Yan Liu, Wei Guan, Zhen-kun Lu, Rui Guo, Yong-Gang Xia, Shao-Wa Lv, Bing-You Yang, Hai-Xue KuangFour new sesquiterpenoids (1–4) and two known ones (5–6) were isolated and identified from the stems of Datura metel L.. The structures of the isolated compounds were established by 1D and 2D NMR spectra, as well as HR-ESI-MS. Additionally, the compounds 1–3 possessed the similar novel skelecton and compounds 5–6 were isolated from the Datura genus for the first time. The hypothetical biogenetic pathway was teased and provided. Meanwhile, the antiproliferative activities were evaluated on the two human cancer cells of HepG2 and Hela, respectively.Graphical abstractUnlabelled Image
       
  • Corrigendum to ‘Epidihydropinidine, the main piperidine alkaloid
           compound of Norway spruce (Picea abies) shows promising antibacterial and
           anti-Candida activity’
    • Abstract: Publication date: Available online 10 February 2019Source: FitoterapiaAuthor(s):
       
  • Epidihydropinidine, the main piperidine alkaloid compound of Norway spruce
           (Picea abies) shows antibacterial and anti-Candida activity
    • Abstract: Publication date: Available online 21 December 2018Source: FitoterapiaAuthor(s): Pia Fyhrquist, Virpi Virjamo, Eveliina Hiltunen, Riitta Julkunen-TiittoAbstractThis study reports for the first time antibacterial and antifungal effects of epidihydropinidine, the major piperidine alkaloid in the needles and bark of Norway spruce, Picea abies (L.) Karsten. Epidihydropinidine was growth inhibitory against all bacterial and fungal strains used in our investigation, showing the lowest MIC value of 5.37 mg/mL against Pseudomonas aeruginosa, Enterococcus faecalis, Candida glabrata and C. albicans. Antibacterial effects were also recorded against Staphylococcus aureus and Bacillus cereus (MIC 10.75 mg/mL) as well as against Salmonella enterica (MIC and MBC 43 mg/mL). Our preliminary results suggest that Norway spruce could be a source for antibacterial piperidine alkaloids.
       
 
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