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Cycloartane triterpenoid and its glucoside isolated from Cassia occidentalis

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Chinese Journal of Natural Medicines 2017年第12期15卷 950-954页

作者： LI Shi-Fei LI Shun-Lin Institute of Molecular Science Shanxi University State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of Botany Chinese Academy of Sciences

In the present study, one new cycloartane triterpenoid, named cycloccidentalic acid C(1) and its glucoside, cycloccidentaliside VI(2) were isolated from the whole plant of Cassia occidentalis. Their structures were elucidated by a combinational analyses of 1D and 2D NMR data and HRMS. Compound 2 showed modest anti-HIV-1 activity with EC_(50) value of 1.44 μmol·L^(-1) and TI(Therapeutic Index) value of 15.59.

关键词： Cycloartane triterpenoid Cassia occidentalis Cycloccidentalic acid C Cycloccidentaliside Ⅵ

triterpenoid of avocado (Persea americana) seed and its cytotoxic activity toward breast MCF-7 and liver HepG2 cancer cells

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Asian Pacific Journal of Tropical Biomedicine 2017年第5期7卷 397-400页

作者： Andi Nur Fitriani Abubakar Suminar Setiati Achmadi Irma Herawati Suparto Laboratory of Organic Chemistry Department of ChemistryFaculty of Mathematics and Natural SciencesBogor Agricultural UniversityBogor 16680Indonesia Laboratory of Microbiology&Immunology Primate Research CenterBogor Agricultural UniversityBogor 16151Indonesia

Objective:To determine the structure of triterpenoid isolated from avocado seeds and the cytotoxic effect on MCF-7 and Hep G2 cells.Methods:The powder sample was macerated with ethanol,followed with separation of the extract by column chromatography.The target compound was monitored on thin layer chromatography plate and reagent Lieberman–Buchard.The isolated compound was characterized by spectral analysis,mainly ultraviolet,infrared,and liquid chromatographymass spectroscopy and their spectroscopic data with those reported in literature were compared.In vitro cytotoxic activity was investigated against Vero,MCF-7,and Hep G2 cell lines using MTT assay.Results:A triterpenoid compound was isolated from ethanol extract.The extracts,fraction(F3),and the isolated compound showed a significant cytotoxic activity against all investigated cell lines.MTT assay showed that the triterpenoid isolate inhibited cell proliferation of MCF-7 and Hep G2 cell line with the IC50 values of 62 mg/m L and 12 mg/m L,respectively,and was safe to normal cells.Conclusions:The results of the present study reveal that triterpenoid from avocado seeds have the potential for further development as anticancer agents.

关键词： Persea americana triterpenoid MCF-7 HepG2 Cancer cells

Immunomodulatory activity of a lupane triterpenoid ester isolated from the eastern Nigeria mistletoe,Loranthus micranthus(Linn)

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Asian Pacific Journal of Tropical Medicine 2011年第7期4卷 514-522页

作者： Omeje Edwin Ogechukwu Osadebe Patience Ogoamaka Nworu Chukwuemeka Sylvester Akira Kawamura Peter Proksch Department of Pharmaceutical and Medicinal Chemistry Faculty of Pharmaceutical SciencesUniversity of Nigeria410001NsukkaNigeria Department of Pharmacology and Toxicology Faculty of Pharmaceutical SciencesUniversity of Nigeria410001NsukkaNigeria Department of Chemistry Hunter College of CUNYThe City University of New YorkU.S.A Department of Pharmaceutical Biology Heinrich-Hein UniversityDusseldorfGermany

Objective:To provide further evidence for the ethnomedicinal use of the Eastern Nigeria mistletoe,Loranthus micranthus(L.micranthus),as an immunostimulant.Methods:Solvent fractions from the crude extract of the mistletoe plant was obtained and screened by the cell mediated delayed type hypersensitivity reaction(DTHR) model in mice.Then the immunomodulatory potentials of a major lupane triterpenoid ester isolated from an active hexane fraction of the Eastern Nigeria mistletoe was investigated.Three lupeol-based triterpenoid esters: 7β15α-dihydroxyl-lup-20(29)-ene-3β-palmitate(Ⅰ),7β,15α-dihydroxyl-lup-20(29)- ene-3β-stearate(Ⅱ) and 7β,15α-dihydroxyl-lup-20(29)-ene-3β-decadecanoate(Ⅲ) were isolated from the plant leaves epiphyting on a local kola nut tree and were characterized. Compound 1 was subjected to cell proliferation studies using C57H1/6 splenocvtes at three dose levels(5.25 and 100μg/mL) in presence of controls.Furthermore,the effect of this compound on IL-8 receptor expression was evaluated at three doses(1,5 and 10μg/mL) using the real time polymerase chain reaction assay.Results:This triterpenoid ester produced some enhancement of the splenocytes at the tested doses but at doses higher than 5μg/mL caused inhibition of the IL-8 receptor expression.Conclusions:The present findings support the ethnomedicinal use of the Eastern Nigeria Mistletoe in the management of diseases affecting the immune system.The trilerpenoid(s) have some immunomodulatory abilities on splenocytes and IL-8 receptors and may partly account lor the overall immunomodulatory activity of this plant.

关键词： Lupane triterpenoid Loranthus micranthus Eastern Nigeria mistletoe Interleukin-8 Cell proliferation Anti-inflammatory

Ginsenoside-Rg_6, a Novel triterpenoid Saponin from the Stem-Leaves of Panax ginseng C. A. Mey.

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Chinese Chemical Letters 2000年第10期11卷 909-912页

作者： Xiu Wei YANG, Long Yun LI, Jian Ming TIAN, Zhi Wei ZHANG, Jin Mei YE, Wei Fang Gu (National Research Laboratory of Natural & Biomimetic Drugs, Peking University, Beijing 100083) (Academy of Chinese Traditional Medicine and Materia Medica of Jilin Provinc Natl. Res. Lab. Nat. Biomimetic D. Peking University Beijing 100083 China Acad. Chinese Traditional Med. M. Changchun 130021 China

A novel dammarane-type triterpene oligoglycoside, named ginsenoside-Rg6 3, was isolated from the stem-leaves of Panax ginseng C. A. Mey., together with two known ones, 20(S)-ginsenoside-Rg2 1 and 20(R)-ginsenoside-Rg2 2. On the basis of chemical and physicochemical evidence , the structure of ginsenoside-Rg6 have been elucidated as 6-O-(-L-rhamnosyl-(1?2)-(-D-glucopyranosyl-dammarane-(E)-20(22), 24-diene-3(, 6(, 12(-triol.

关键词： Panax ginseng C. A. Mey. stem-leaves triterpenoid ginsenoside-Rg_6.

Schisanlactone G,a new 3,4-seco-lanostane triterpenoid from Schisandra sphenanthera

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Chinese Chemical Letters 2009年第5期20卷 601-603页

作者： Rong Ren Guo Jun Luo Hong Mei Li Zhao Yuan Wu Hai Zhou Li Rong Tao Li The College of Life Science and Technology Kunming University of Science and Technology Kunming 650224 PR China

A new 3,4-seco-lanostane triterpenoid, schisanlactone G （1）, was isolated from the fruits of Schisandra sphenanthera. Its structure was established on the basis of extensive spectroscopic analysis.

关键词： Schisandra sphenanthera triterpenoid Schisanlactone G

Studies on triterpenoid Glycosides from Rhizomes ofPanacis majoris and Their Antiplatelet Aggregation Activity

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Chemical Research in Chinese Universities 2016年第6期32卷 943-946页

作者： LI Min JIN Yongri WANG Xiaozhong WU Qian LIU Ying LI Peng LI Xuwen College of Chemistry Jilin University Changchun 130021 P. R. China

A new triterpenoid glycoside（l） and seven known triterpenoid glycosides, pseudoginsenoside RT2（2）,yesanchinoside R2（3）, vinaginsenoside R13（4）, vinaginsenoside R8（5）, notoginsenoside E（6）, 6＂＇-O-acetylginsenosideRe（7）, 6＂-O-acetylginsenoside Rbl（8）, were isolated from the rhizomes of Panaeis maforis. The new triterpenoidglycoside was elucidated as 3-O-[β-D-glucopyranosyl-（l→2）-fl-D-（6＇-O-ethyl）-glucuronopyranosyl]-oleanolicacid-28-O-β-D-glucopyranoside by extensive spectroscopic and phytochemical methods. Compounds 2-8 wereobtained from the plant for the first time. Compounds 3 and 4 displayed good activities against adenosine diphosphate（ADP）-induced platelet aggregation, and compounds 1, 5, 6 and 8 showed moderate activities. Compound 6 exhibitedmoderate antiplatelet aggregation activity induced by arachidonic acid（AA）.

关键词： Panacis majoris Rhizome triterpenoid glycoside Antiplatelet aggregation

Petatrichol B: A Pentacyclic triterpenoid with Unusual Skeleton from Petasites tricholobus

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Chinese Chemical Letters 2005年第10期16卷 1351-1353页

作者： Wei Dong XIE Ping Lin LI Zhong Jian JIA College of Chemistry and Chemical Engineering National Laboratory of Applied Organic Chemistry Lanzhou University Lanzhou 730000

A novel pentacyclic triterpenoid, petatrichol B, was isolated from the rhizome of Petasites tricholobus. Its structure was established by means of spectroscopic analysis （EIMS, HRSIMS, IR, 1D NMR and 2D NMR）.

关键词： Petasites tricholobus Compositae triterpenoid petatrichol B.

Selective and facile deacetylation of pentacyclic triterpenoid under methanolic ammonia condition and unambiguous NMR analysis

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Chinese Chemical Letters 2020年第2期31卷 333-336页

作者： Han Wang Renyang Xu Shuobin Liang Fuxiang Ran Lihe Zhang Yongmin Zhang Demin Zhou Sulong Xiao State Key Laboratory of Natural and Biomimetic Drugs School of Pharmaceutical SciencesPeking UniversityBeijing 100191China State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunming 650201China Department of Pharmacy The Second Affiliated HospitalDalian Medical UniversityDalian 116023China Sorbonne Université Institut Parisien de Chimie MoléculaireCNRS UMR 82324 place Jussieu75005 ParisFrance

The acetyl ester plays an important role for protection of the hydroxyl groups in carbohydrates synthesis.In the present study,we described an efficient deprotection of acetyl group of pentacyclic triterpenoid by using methanolic ammonia in THF solution.Good selectivity for cleaving gal-C2-OAc group of 3β-hydroxy-olean-12-en-28-oic acid 28-N-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside(3) was achieved in the presence of methanolic ammonia within 4 h at low temperature(-60℃) in a yield of 56%.The reaction disclosed here provides a new method for the synthesis of C2 selective modified carbohydrates,which is more useful than conventional synthesis procedure that usually requires many steps including temporary regioselective protection and deprotection.When the reaction temperature was increased from -60℃ to room temperature,the cleavage of the other three acetyl groups of galactose in an order of C4-OAc>C3-OAc>C6-OAc was observed.Based on this study,a plausible route for the deacetylation reaction has been proposed.

关键词： Pentacyclic triterpenoid Deacetylation Methanolic ammonia Selectivity Synthesis

Two triterpenoid Dimers from Rubus pungens Camb var. oldhamii

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Chinese Chemical Letters 2000年第2期11卷 143-146页

作者： Bin Gui WANG1,2 Wei Ming ZHU2 Xiao Ming LI2 Zhong Jian JIA1 Xiao Jiang HAO2 (1 National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 2 Laboratory of Phytochemistry, Kunming Institute of Botany, Academia Sinica, Kunming 6 Natl. Lab. of Appl. Organ. Chemistry Lanzhou University Lanzhou 730000 China Laboratory of Phytochemistry Kunming Institute of Botany Academia Sinica Kunming 650204 China

Two new triterpenoid saponin dimers, named rubupungenoside A (1) and B (2), have been isolated from the aerial parts of Rubus pungens Camb. var. oldhamii. Their structures have been established on the basis of spectro... 详细信息

关键词： Rubus pungens Camb. var oldhamii ursene triterpenoid dimer