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steroidal saponins from the Genus Smilax and Their Biological Activities

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Natural Products and Bioprospecting 2017年第4期7卷 283-298页

作者： Li-Wen Tian Zhen Zhang Hai-Lan Long Ying-Jun Zhang School of Pharmaceutical Sciences Southern Medical UniversityGuangzhou 510515China State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunming 650201China

The Smilax species,widely distributed in tropical region of the world and the warm areas of East Asia and North America,are extensively used as folk medicine to treat inflammatory *** investigation on Smilax species showed they are rich sources of steroidal saponins with diversified structure types,including spirostane,isospirostane,furostane,pregnane,and *** review mainly summarizes the steroidal saponins(1–104)reported from the genus Smilax between 1967 and 2016,and their biological *** relationship between structures of steroidal saponins and related biological activities were briefly discussed.

关键词： Smilax steroidal saponins Biological activities

Advances in the antitumor activities and mechanisms of action of steroidal saponins

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Chinese Journal of Natural Medicines 2018年第10期16卷 732-748页

作者： ZHAO Ya-Zheng ZHANG Yuan-Yuan HAN Han FAN Rui-Ping HU Yang ZHONG Liang KOU Jun-Ping YU Bo-Yang Jiangsu Key Laboratory of TCM Evaluation and Translational Research Department of Complex Prescription of Traditional Chinese MedicineChina Pharmaceutical University

The steroidal saponins are one of the saponin types that exist in an unbound state and have various pharmacological activities,such as anticancer,anti-inflammatory,antiviral,antibacterial and nerves-calming *** is a growing health problem *** progress has been made to understand the antitumor effects of steroidal saponins in recent *** to reported findings,steroidal saponins exert various antitumor activities,such as inhibiting proliferation,inducing apoptosis and autophagy,and regulating the tumor microenvironment,through multiple related signaling *** article focuses on the advances in domestic and foreign studies on the antitumor activity and mechanism of actions of steroidal saponins in the last five years to provide a scientific basis and research ideas for further development and clinical application of steroidal saponins.

关键词： steroidal saponins Tumor Mechanism

Two New steroidal saponins from Tacca plantaginea

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Chinese Chemical Letters 2002年第7期13卷 633-636页

作者： Hai Yang LIU Chang Xiang CHEN Laboratory of Phytochemistry Kunming Insitute of BotanyChinese Academy of ScienceKunming 650204

Two new C27 steroidal glycosides, named taccaoside A (1) and B (2), were isolated from the traditional Chinese herb Tacca plantaginea. The spectroscopic and chemical evidences revealed their structures to be 26-O--D-glucopyranosyl-(25R)-3?26-dihydroxy furost-5,20-diene -3-O-[?L-rhamnopyranosyl(12)]-[?L-rhamnopyranosyl(13)]--D-glucopyranoside (1) and 26-O--D-glucopyranosyl-(25R)-3?26-dihydroxy furost-5,20-diene-3-O-[?L-rhamnopyranosyl- (12)]-[?D-glucopyranosyl(13)--L-rhamnopyranosyl(13)]--D-glucopyranoside (2), res- pectively.

关键词： Tacca plantaginea steroidal saponins taccaoside A and B.

Unraveling the serial glycosylation in the biosynthesis of steroidal saponins in the medicinal plant Paris polyphylla and their antifungal action

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Acta Pharmaceutica Sinica B 2023年第11期13卷 4638-4654页

作者： Yuegui Chen Qin Yan Yunheng Ji Xue Bai Desen Li Rongfang Mu Kai Guo Minjie Yang Yang Tao Jonathan Gershenzon Yan Liu Shenghong Li State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunming 650201China State Key Laboratory of Southwestern Chinese Medicine Resources Innovative Institute of Chinese Medicine and PharmacyChengdu University of Traditional Chinese MedicineChengdu 611137China Key Laboratory for Plant Diversity and Biogeography of East Asia Kunming Institute of BotanyChinese Academy of SciencesKunming 650201China Max Planck Institute for Chemical Ecology Jena D-07745Germany University of Chinese Academy of Sciences Beijing 100049China

Sugar-sugar glycosyltransferases play important roles in constructing complex and bioactive ***,we characterized a series of UDP-glycosyltransferases responsible for biosynthesizing the branched sugar chain of bioactive steroidal saponins from a widely known medicinal plant Paris polyphylla *** them,a 2'-O-rhamnosyltransferase and three 6'-O-glucosyltrasferases catalyzed a cascade of glycosylation to produce steroidal diglycosides and triglycosides,*** UDP-glycosyltransferases showed astonishing substrate promiscuity,resulting in the generation of a panel of 24 terpenoid glycosides including 15 previously undescribed compounds.A mutant library containing 44 variants was constructed based on the identification of critical residues by molecular docking simulations and protein model alignments,and a mutant UGT91AH1^(Y187A)with increased catalytic efficiency was *** steroidal saponins exhibited remarkable antifungal activity against four widespread strains of human pathogenic fungi attributed to ergosterol-dependent damage of fungal cell membranes,and 2'-O-rhamnosylation appeared to correlate with strong antifungal *** findings elucidated the biosynthetic machinery for their production of steroidal saponins and revealed their potential as new antifungal agents.

关键词： Paris polyphylla var.yunnanensis steroidal saponins Glycosyltransferases Sugar chain elongation Antifungal activity

Spirostane steroidal saponins from the Undergroud Parts of Tupistra chinensis

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Chinese Chemical Letters 2005年第7期16卷 911-914页

作者： GuangXuWU XiaoYiWEI WeiXinCHEN GuangdongKeyLaboratoryforPost-harvestScienceofFruitsandVegetables SouthChinaAgricultureUniversityGuangzhou510642／／CollegeofLifeScienceYangtzeUniversityJinzhou434023 SouthChinaBotanicalGarden ChineseAcademyofSciencesGuangzhou510650 GuangdongKeyLaboratoryforPost-harvestScienceofFruitsandVegetables SouthChinaAgricultureUniversityGuangzhou510642

Two new spirostanol saponins, (25S)-spirostane-1β,3β,5β-triol 3-O-β-D-glucopyrano- side 1 and rhodeasapogenin 3-O-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranoside 2, together with a known saponin, rhodeasapogenin 3-O-β-D-glucopyranoside 3, were isolated from the underground parts of Tupistra chinensis Bak.. Their structures were determined by spectroscopic analysis.

关键词： Tupistra chinensis Bak. Liliaceae steroidal saponins (25S)-spirostane-1β,3β,5β-triol 3- O-β-D-glucopyranoside rhodeasapogenin 3-O-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranoside.

Fingerprint analysis of Zhimu-Huangbai herb pair and simultaneous determination of its alkaloids, xanthone glycosides and steroidal saponins by HPLC-DAD-ELSD

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Chinese Journal of Natural Medicines 2014年第7期12卷 525-534页

作者： ZHANG Feng YANG Qi SUN Lian-Na GAO Shou-Hong TAO Xia CHEN Wan-Sheng Department of Pharmacy Changzheng Hospital Second Military Medical University Department of Pharmacognosy School of Pharmacy Second Military Medical University

AIM: To develop and validate a high performance liquid chromatography(HPLC) coupled with diode array and evaporative light scattering detectors(DAD-ELSD) method for the quantitative determination and fingerprint analysis of ten active constituents in three chemical classes(namely, xanthone glycosides, steroidal saponins, and alkaloids) in Zhimu-Huangbai herb pair(ZB). METHOD: Chromatographic separation was performed on a Diamonsil C18 column(4.6 mm × 250 mm, 5 μm, Dikma) by gradient elution using acetic acid in acetonitrile solution at a flow rate of 1.0 mL·min–1 at 260 nm. The drift tube temperature of ELSD was set to 60 ℃ and nebulizer gas pressure was 4.0 Bar. Method validation was performed to assure its linearity, limits of detection and quantification, precision, repeatability, stability, and accuracy. RESULTS: The HPLC-DAD-ELSD method allowed the quantification of ten compounds(phellodendrine, jatrorrhizine, palmatine, berberine, neomangiferin, mangiferin, timosaponin E-I, timosaponin B-II, timosaponin B, and timosaponin A-III), and was successfully applied to fingerprint analysis for ten batches of ZB samples. CONCLUSION: This was the first time to apply the combination of DAD and ELSD for the simultaneous determination of ten active ingredients in ZB. The results showed that the combination of quantitative analysis for marker ingredients and chemical fingerprint for the TCM herb pair provides a potentially powerful, widely introduced, and internationally accepted strategy for assessment of complex TCM formulas.

关键词： Anemarrhena asphodeloides Phellodendron amurense Chromatographic fingerprint HPLC-DAD-ELSD Xanthone glycosides steroidal saponins Alkaloids Simultaneous determination

Two new steroidal saponins from the rhizomes of Dioscorea zingiberensis

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Chinese Journal of Natural Medicines 2014年第2期12卷 142-147页

作者： ZHENG Lu ZHOU Yuan ZHANG Jia-Yu SONG Min YUAN Ye XIAO Yan-Jiao XIANG Ting Research Institute of Traditional Chinese Medicine Yangtze River Pharmaceutical Group Co. Ltd. School of Chinese Pharmacy Beijing University of Chinese Medicine

AIM: To investigate the chemical constituents of Dioscorea zingiberensis C. H. Wright. METHODS: The compounds were isolated by various chromatographic techniques, and the structures of the new steroidal saponins were elucidated by extensive 1D- and 2D-NMR, MS, and IR spectral analysis. RESULTS: The 70% EtOH extract of the rhizomes of Dioscorea zingiberensis afforded two new steroidal saponins, zingiberenosides A(1) and B(2), along with eight known analogues, 3β, 26-dihydroxy-25(R)-furosta-△5, 20(22)-diene-3-O-α-Lrhamnopyranosyl-(1→2)-O-β-D-glucopyranoside(3), methyl parvifloside(4), deltoside(5), methyl deltoside(6), zingiberensis new saponin(7), deltonin(8), progenin III(9) and diosgenin-diglucoside(10). CONCLUSION: Two new steroidal saponins were isolated from Dioscorea zingiberensis and their structures determined.

关键词： Dioscorea zingiberensis Dioscoreaceae steroidal saponins Zingiberenoside

steroidal saponins with anti-inflammatory activity from Tribulus terrestris L.

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Acupuncture and Herbal Medicine 2022年第1期2卷 41-48页

作者： Miaojie Yang Mahmood Brobbey Oppong Jingrui Di Qing Yuan Yanxu Chang Miaomiao Jiang Shijie Cao Pengzhi Dong Lin Li Yan Xie Xiaoying Luan Limin Hu Lijuan Chai Peng Zhang Tianjin State Key Laboratory of Component-based Chinese Medicine Institute of Traditional Chinese MedicineTianjin University of Traditional Chinese MedicineTianjinChina Tianjin Key Laboratory of Phytochemistry and Pharmaceutical Analysis Tianjin University of Traditional Chinese MedicineTianjinChina Department of Pharmaceutical Chemistry School of PharmacyCollege of Health SciencesUniversity of GhanaGhana

Objective:Tribulus terrestris L.(***)is a highly valuable traditional Chinese medicine used to treat stroke,inflammation,pulmonary fibrosis,liver cancer,and *** identify the basic substance responsible for the anti-inflammatory effect of TST(total saponins of Tribulus),its chemical composition was systematically studied,and its effect of inhibiting nitric oxide generation and the expression of related inflammatory factors were ***:To separate chemical constituents from *** by column *** methods,including 1D and 2D nuclear magnetic resonance spectroscopy(NMR)and mass spectrometry(MS)techniques,were used to elucidate the isolated *** anti-inflammatory activities of TST and several compounds were evaluated in ***:Fifteen steroidal saponins,including 9 furostanol steroidal saponins(1,2,3,4,5,6,7,8,and 15)and 6 isospirostanol steroidal saponins(9,10,11,12,13,and 14),were isolated from *** significantly decreased the expression of tumor necrosis factor-a(TNF-a)and interleukin-6(IL-6)in RAW 264.7 cells stimulated by *** 13 and 15 evidently reduced TNF-a *** 6,10,12,13,and 15 markedly reduced IL-6 ***:Compounds 1 was a novel furostanol steroidal saponin,named 26-O-b-D-glucopyranosyl-(25R)-5afurostan-12-carbonyl-20(22)-en-3b,26-diol-3-O-{b-D-xylopyranosyl-(1→2)-[b-D-xylopyranosyl-(1→3)]-b-D-glucopyranosyl-(1→4)-[a-L-rhamnopyranosyl-(1→2)]-b-D-galactopyranoside}.Compounds 2 was isolated from the family Zygophyllaceae for the first time,and 5 and 6 were isolated from the Tribulus *** and compounds 6,10,12,13,and 15 exerts antiinflammatory activity.

关键词： Interleukin-6 Nitric oxide(NO)inhibition steroidal saponins Tribulus terrestris L. Tumor necrosis factor-a

Untiring Researches for Alternative Resources of Rhizoma Paridis

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Natural Products and Bioprospecting 2018年第4期8卷 265-278页

作者： Xu-Jie Qin Wei Ni Chang-Xiang Chen Hai-Yang Liu State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of Sciencesand Yunnan Key Laboratory of Medicinal ChemistryKunming 650201People’s Republic of China

Rhizoma Paridis(RP,M®),a traditional Chinese medicine,is the rhizoma of Paris polyphylla ***(PPY)or *** *** which are widely used as important raw materials for several Chinese patent ***,the wild resources of these herbs have become less and less due to their slow-growing characteristics and previously excessive *** review covers untiring investigations on alternative resources of RP by our research group over the past decades,including non-medicinal parts of PPY as well as other plants of Liliaceae and Liliflorae *** arial parts of PPY and the whole plants of Trillium kamtschaticum might be alternative resources for RP based on the fact that they shared the same or similar saponins and bioactivities.

关键词： Rhizoma Paridis Paris polyphylla Alternative resources steroidal saponins Bioactivities