Triterpenoid saponins from the roots of Clematis chinensis Osbeck

A new triterpenoid saponin named clematichinenoside AR₂, along with the six known compounds, was isolated and characterized from Clematis chinensis Osbeck (Ranunculaceae), a commonly used traditional Chinese medicine with anti-inflammatory and anti-rheumatoid activities. The structure of the new saponin was elucidated as 3-O-β-[(O-α-l-rhamnopyranosyl-(1 → 6)-O-β-d-glucopyranosyl-(1 → 4)-O-β-d-glucopyranosyl-(1 → 4)-O-β-d-ribopyranosyl-(1 → 3)-O-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl)oxy]olean-12-en-21α-hydroxy-28-oic acid-O-α-l-rhamnopyranosyl-(1 → 4)-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (1) by spectral analysis and chemical methods. The effects of two major saponins (clematichinenosides AR and AR₂) on the secretion of TNF-α in murine peritoneal macrophages induced by lipopolysaccharides were further investigated. The result indicated that a majority of triterpenoid saponins of this herb may be useful in the exploration of lead compounds for the treatment of some autoimmune diseases.     

Cytotoxic triterpene saponins from Clematis mandshurica

Two new triterpene saponins, mandshunosides A and B (1 and 2), were isolated from the roots and rhizomes of Clematis mandshurica. Their structures were elucidated on the basis of spectroscopic evidence and hydrolysis products. Compounds 1 and 2 showed inhibitory activities against two colorectal human cancer cells HCT 116 (IC₅₀ 2.1 μM for 1 and 2.5 μM for 2) and HT-29 (IC₅₀ 3.7 μM for 1 and 3.3 μM for 2).     

Two new triterpenoid saponins from rhizome of Anemone amurensis

Two new triterpenoid saponins were isolated from the 70% ethanol extract of the rhizome of Anemone amurensis, they are oleanolic acid 28-O-β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (1) and 23,27-dihydroxy oleanolic acid 3-O-α-l-arabinopyranoside (2). The structures of 1 and 2 were elucidated on the basis of chemical and spectral analysis, including 1D and 2D NMR data and HR-ESI-MS. Compounds 1 and 2 were tested for cytotoxicities against three human cancer cell lines (A549, Hep-G2, and MCF-7). Compound 1 showed potent cytotoxicity with IC₅₀ values of 34.76, 41.17, and 28.92 μM, respectively, while compound 2 with IC₅₀>100 μM.     

粗齿铁线莲的化学成分研究

目的研究粗齿铁线莲的化学成分。方法采用大孔树脂、硅胶柱层析、Sephadex LH-20、ODS柱层析、半制备型高效液相等色谱分离方法进行分离纯化,经理化性质和波谱数据分析鉴定化合物结构。结果分离鉴定了6个三萜皂苷类化合物,分别鉴定为saponin CP4(Ⅰ)、saponin CP7(Ⅱ)、clematoside S(Ⅲ)、clematichinenosideA(Ⅳ)、clematichinenoside C(Ⅴ)、saponin PJ3(Ⅵ)。结论化合物Ⅰ~Ⅵ均为首次从该植物中分离得到。     

Triterpenoid saponins from Gynostemma pentaphyllum

Four new dammarane-type triterpene saponins, 1–4, were isolated from the aerial parts of Gynostemma pentaphyllum (Thunb.) Makino. Their structural elucidations were accomplished mainly on the basis of spectroscopic methods, such as IR, HR-TOF-MS, and NMR. Compounds 1–4 showed moderate cytotoxic activities against cancer cell lines HL-60, Colon205, and Du145 in vitro.     

Triterpenoid saponins from the rhizome of Polygonatum sibiricum

Three new triterpenoid saponins, polygonoides C (1), D (2), and E (3), were obtained from the ethanolic extract of the rhizome of Polygonatum sibiricum Redoute. On the basis of NMR and ESI-MS spectra, and chemical evidence, the structures of the three new compounds were elucidated as 3-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranosyl-3β,7β,22β-trihydroxy-oleanolic acid (1), 3-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranosyl-3β,7β,22β-trihydroxy-oleanolic acid methyl ester (2), and 3-O-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 4)-[α-L-rhamno-pyranosyl-(1 → 2)]-β-D-glucopyranosyl-3β,21β-dihydroxy-oleanolic acid 28-O-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranoside (3).     

Triterpenoid saponins from Clematis tangutica

Two new triterpenoid saponins, tanguticoside A and B along with seven known saponins vitalboside B, alpha-hederin, saponin PK, beta-hederin, saponin PJ3, saponin PE, and ciwujianoside A were isolated from aerial part of Clematis tangutica. By chemical and spectral evidences methods, the structures of tanguticoside A and B were elucidated as 3-O-beta-D-glucopyranosylhederagenin 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside and 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosylhederagenin 28-O-alpha-D-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside, respectively.     

Clematomandshurica saponin E,a new triterpenoid saponin from Clematis mandshurica

A new triterpenoid saponin, clematomandshurica saponin E, together with four known saponins were isolated and characterized from the roots and rhizomes of Clematis mandshurica (Ranunculaceae), a commonly used traditional Chinese medicine with anti-inflammatory and antirheumatoid activities. On the basis of spectroscopic analysis, including HR-ESI-MS, IR, 1D, and 2D NMR spectral data and hydrolysis followed by chromatographic analysis, the structure of the new triterpenoid saponin was elucidated as 3-O-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 4)-β-d-ribopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl oleanolic acid 28-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranoside.     

Triterpenoid saponins from Anemone flaccida induce apoptosis activity in HeLa cells

Five triterpenoid saponins were isolated from Anemone flaccida Fr. Schmidt. Their structures were identified as glycoside St-I4a (1), glycoside St-J (2), anhuienoside E (3), hederasaponin B (4), and flaccidoside II (5). Compounds 1–2 were isolated from Anemone family for the first time, and compounds 3–4 were isolated from this plant for the first time. The inhibitory effects of saponins on proliferation of HeLa cells were studied by MTT assay, the apoptosis-induction activity was observed by cell-cycle analysis and caspase-3 expression assay. The antitumor activities of the saponins were ranked in the following order: 5>3>4>1>2. The data presented here indicated that naturally occurring triterpenoid saponins can be regarded as excellent structures for the potential development of new anticancer agents.     

地榆中三萜皂苷类成分及其抗炎活性研究

摘要: 目的 研究地榆中的三萜皂苷类成分及其抗炎活性。方法 利用硅胶、Sephadex LH-20和ODS柱色谱分离纯化，通过理化常数和波谱分析（¹H-NMR和¹³C-NMR）确定结构；采用二甲苯致小鼠耳肿胀模型，对分离得到的三萜皂苷进行体内抗炎活性研究。结果 从体积分数70%乙醇提取物中分离并鉴定5个三萜皂苷，分别是：地榆皂苷 I (1)、niga-ichigoside (2)、3β-[(α-L-arabinopyranosyl)oxy]-29-hydroxyolean-12-en-28-oic acid- β-D-glucopyranosyl ester (3)、3β-[(α-L-arabinopyranosyl)oxy]-urs-12,18-dien-28-oic acid-β-D-glucopyranosyl ester (4)、地榆皂苷II (5)。结论 化合物2和3为首次从地榆属植物中分离得到的已知化合物；皂苷1、2和5显示出一定的抗炎作用。     

Triterpenoid saponins from Vaccaria segetalis

A new triterpenoid saponin, named segetoside C (1), and two known saponins, vaccaroid A (vaccaroside A) (2) and dianoside G (3), have been isolated from the seeds of Vaccaria segetalis. On the basis of chemical reaction and spectral data, the structure of segetoside C (1) has been established as: gypsogenic acid-28-O-[β-D-glucopyranosyl-(1 → 3)]-[6-O-acetyl-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranoside.     

Two new triterpenoid saponins from Glochidion puberum

Two new triterpenoid saponins, puberosides A and B, were isolated from the aerial parts of Glochidion puberum. Their structures were elucidated as 3α-[(O-β-d-glucopyranosyl-(1 → 3)-O-α-l-arabinopyranosyl)oxy]-22α-benzoyloxy-olean-12-ene-16α,28-diol (1) and 3α-[(O-β-d-glucopyranosyl-(1 → 3)-O-α-l-arabinopyranosyl)oxy]-28-benzoyloxy-olean-12-ene-16α,22α-diol (2) by analysis of their spectroscopic data.     

Chemical constituents from rhizome of Anemone amurensis

Phytochemical investigation of the 70% EtOH extract of the rhizome of Anemone amurensis led to the isolation of two new oleanane-type triterpenoid saponins 1 and 2. Their structures were elucidated on the basis of chemical and spectral analysis, including 1D, 2D NMR data, and HR–ESI–MS. Compounds 1 and 2 were tested for cytotoxicities against two human cancer cell lines (A549 and Hep-G2). Compound 2 showed potent cytotoxicity with IC₅₀ values of 38.53 and 66.17 μM, respectively, while compound 1 with IC_50?>?100 μM.     

Triterpenoid glycosides from Stauntonia chinensis

A new bidesmoside triterpenoid saponin, named stauntoside C1 (1), along with three known saponins (2–4) was isolated from Stauntonia chinensis DC. (Lardizabalaceae). Their structures were established by means of spectral and chemical methods as 3-O-β-d-xylopyranosyl-(1 → 2)-O-β-d-xylopyranosyl-(1 → 3)-O-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl oleanolic acid 28-O-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (1), scabiosaponin E (2), sieboldianoside B (3), and kizutasaponin K₁₂ (4).     

Cytotoxic triterpenoid saponins from the defatted seeds of Camellia oleifera Abel

Five new oleanane-type triterpenoid saponins, oleiferasaponins D₁–D₅ (1–5), were isolated from the defatted seeds of Camellia oleifera Abel. Their structures were elucidated by spectroscopic and chemical methods. The cytotoxic activities of compounds 1–5 were evaluated against five human tumor cell lines (HCT-116, HepG2, BGC-823, NCI-H1650, and A2780). Compounds 1–2 exhibited cytotoxic activity against five human cancer cell lines, with IC₅₀ values ranging from 3.31 to 10.23 μM. Compounds 3–5 showed moderate cytotoxic activities toward the tested cell lines.     

紫金牛属植物中三萜皂苷类成分核磁共振波谱学特征

目的对紫金牛属植物近 2 0年的三萜皂苷类成分的结构及波谱学研究内容进行综述。方法查阅国内外研究文献 ,对紫金牛属植物中分离得到的皂苷结构及波谱特征进行归纳、总结。结果目前已从紫金牛属植物中分离鉴定了 32个皂苷 ,通过分析其核磁数据 ,应用烯碳数据和羰基碳的数据可推测基本结构类型 ,根据含氧碳及相邻碳的化学位移值可确定羟基的取代位置。同时也总结了该属植物皂苷中糖的种类和连接位置。结论通过总结紫金牛属三萜皂苷波谱特征规律 ,对进一步鉴定该类化合物结构以及进行波谱数据的归属都起着重要的作用     

Three new dammarane-type triterpene saponins from the leaves of Panax ginseng C.A. Meyer

Three new dammarane-type triterpene ginsenosides, together with six known ginsenosides, were isolated from the leaves of Panax ginseng C.A. Meyer. The new saponins were named as ginsenoside Rh₁₁, ginsenoside Rh₁₂, and ginsenoside Rh₁₃. Their structures were elucidated as (20S)-3β,6α,12β,20-tetrahydroxydammara-25-ene-24-one 20-O-β-d-glucopyranoside (1), (20S)-3β,12β,20,24,25-pentahydroxydammarane 20-O-β-d-glucopyranoside (2), and (20S,23E)-3β,12β,20,25-tetrahydroxydammara-23-ene 20-O-β-d-glucopyranoside (3) on the basis of 1D and 2D NMR experiments and mass spectra. The known ginsenosides were identified as ginsenoside M_7cd, ginsenoside Rg₆, ginsenoside Rb₃, gypenoside XVII, gypenoside IX, and 20-(E)-ginsenoside F₄.     

New oleanane-type triterpenoid saponins isolated from the seeds of Celosia argentea

Three new oleanane-type triterpenoid saponins named celosins H (1), I (2), and J (3) were isolated from the seeds of Celosia argentea L. Their structures were characterized as 3-O-β-d-xylopyranosyl-(1 → 3)-β-d-glucuronopyranosyl-polygalagenin 28-O-β-d-glucopyranosyl ester, 3-O-β-d-glucuronopyranosyl-medicagenic acid 28-O-β-d-xylcopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-β-d-fucopyranosyl ester, and 3-O-β-d-glucuronopyranosyl-medicagenic acid 28-O-α-l-arabinopyranosyl-(1 → 3)-[β-d-xylcopyranosyl-(1 → 4)]-α-l-rhamnopyranosyl-(1 → 2)-β-d-fucopyranosyl ester by NMR, MS, and chemical evidences, respectively. In our opinion, celosins H–J could be used as chemical markers for the quality control of C. argentea seeds.     

New dammarane triterpenoid saponins from the leaves of Cyclocarya paliurus

Abstract

Three new dammarane triterpenoid saponins, cyclocariosides O-Q (1–3), were isolated from the ethanolic extracts of the leaves of Cyclocarya paliurus. The structures of these compounds were elucidated by spectroscopic methods.     

Three triterpenoid saponins acylated with monoterpenic acid from Gymnocladus chinensis

A new triterpenoid saponin acylated with monoterpenic acid, together with two known triterpenoid saponins, has been isolated from the fruit of Gymnocladus chinensis Baill. Their structures were elucidated as 2β,23-dihydroxy-3-O-α-L-rhamnopyranosyl-21-O-{(6S)-2-trans-2,6-dimethyl-6-O-[3-O-(β-D-glucopyranosyl)-4-O-((6S)-2-trans-2,6-dimethyl-6-hydroxy-2,7-octadienoyl)-β-L-arabinopyranosyl]-2,7-octadienoyl}-acacic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 6)]-β-D-glucopyranosyl ester (1), gymnocladus saponin E (2), and gymnocladus saponin F₂ (3).