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.     

A new phenolic glycoside and cytotoxic constituents from Celosia argentea

A new phenolic glycoside, 4-O-β-D-apifuranosyl-(1 → 2)-β-D-glucopyranosyl-2-hydroxy-6-methoxyacetophenone (2) and 11 known compounds were isolated from the MeOH extract of the plant Celosia argentea. The structures of the compounds were elucidated on the basis of spectroscopic analysis and chemical methods. Among the isolated compounds, stigmasterol (10) showed moderate inhibitory activities against SGC-7901 and BEL-7404 cells.     

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.     

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.     

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     

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.     

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).     

黄连花中两个新的三萜皂苷黄连花中两个新的三萜皂苷

目的对黄连花(Lysimachia davurica Ledeb.)全草的三萜皂苷成分进行分离和结构鉴定。方法通过大孔树脂纯化,硅胶和反相硅胶色谱分离正丁醇萃取物物中的三萜皂苷;利用多种波谱技术并结合酸水解方法鉴定其化学结构。结果分离鉴定了2个三萜皂苷,其结构分别为3β,16α,29-三羟基-13,28-环氧-齐墩果烷-3-O-β-D-吡喃葡糖基-(1→2)-β-D-吡喃葡糖酸甲酯苷(I),3β,16α,28-三羟基-齐墩果-12-烯-3-O-｛β-D-吡喃葡糖基(1→2)-β-D-吡喃葡糖醛酸｝-28-O-β-D-吡喃葡糖苷(II)。结论化合物I和II为新的三萜皂苷,分别命名为黄连花皂苷D和J。     

细梗香草中的两个新三萜皂苷

目的对细梗香草(Lysimachia capillipes Hemsl.)全草的三萜皂苷成分进行分离和结构鉴定。方法通过大孔树脂纯化，硅胶和反相硅胶色谱分离正丁醇萃取物中的三萜皂苷；利用多种波谱技术并结合酸水解方法鉴定其化学结构。结果分离鉴定了2个三萜皂苷，其结构分别为3β，22α-二羟基-16α-当归酰氧基-28→13-内酯-齐墩果烷-3-O-［β-D-吡喃葡糖基-(1→2)-α-L-吡喃阿拉伯糖基］-22-O-(6-乙酰基)-β-D-吡喃葡糖苷(I),3β,13β,22α-三羟基-16α-乙酰氧基-齐墩果烷-28羧酸钠-3-O-［β-D-吡喃葡糖基-(1→2)-α-L-吡喃阿拉伯糖基］-22-O-β-D-吡喃葡糖苷(II)。结论化合物I和II为新的三萜皂苷，分别命名为细梗香草皂苷I和细梗香草皂苷J。     

HPLC-ELSD法测定四季青中三萜及其皂苷的含量

目的建立同时测定四季青中3种三萜及其皂苷——长梗冬青苷、地榆皂苷I和救必应酸含量的HPLC分析方法。方法C₁₈柱；流动相：甲醇-水（59∶41）；流速1.0 mL·min^-1；检测器：Sedex 55蒸发光散射检测器。结果线性范围为长梗冬青苷2.56～25.60　μg（r=0.999.2），地榆皂苷I 1.64～16.40μg（r=0.998　2）和救必应酸3.74～37.40　μg（r=0.999.4）。平均加样回收率为长梗冬青苷96.3%, RSD　1.6%　(n=5); 地榆皂苷I 97.3%, RSD　3.8% (n=5)；救必应酸97.7%, RSD2.1%　(n=5)。3个化合物的精密度RSD　(n=6)均<4%; 重现性RSD　(n=6)均<5%。结论本方法简便、有效、可行，可用于四季青三萜及其皂苷的含量测定。     

东北刺人参叶中四种新三萜皂苷的分离与结构鉴定

目的研究东北刺人参的三萜皂苷化学成分。方法采用大孔树脂、硅胶、ODS柱色谱分离纯化，经理化常数、光谱学方法鉴定结构。结果分离得到了4个新三萜皂苷，其结构分别鉴定为3-O-β-D-吡喃葡糖基3β，23-二羟基羽扇豆-20(29)-烯-28-酸-28-O-α-L-吡喃鼠李糖基(1→4)-β-D-吡喃葡糖基(1→6)-β-D-吡喃葡糖苷(1);3-O-β-D-吡喃葡糖基常春藤皂苷元-28-O-α-L-吡喃鼠李糖基(1→4)-β-D-吡喃葡糖基(1→6)-β-D-吡喃葡糖苷(2);3-O-β-D-吡喃葡糖基3β-羟基齐墩果-9(11)，12-二烯-28-酸-28-O-α-L-吡喃鼠李糖基(1→4)-β-D-吡喃葡糖基(1→6)-β-D-吡喃葡糖苷(3);3α-羟基齐墩果-12-烯-23，28-二酸-28-O-α-L-吡喃鼠李糖基(1→4)-β-D-吡喃葡糖基(1→6)-β-D-吡喃葡糖苷(4)。结论化合物1～4均为新三萜皂苷，首次从东北刺人参叶中分得。     

牛膝中酸性三萜皂苷成分的分离与鉴定

目的研究中药牛膝中的三萜皂苷类成分.方法采用大孔树脂、硅胶、ODS柱色谱分离纯化,经理化常数、光谱学方法鉴定结构.结果分离得到了6个化合物,鉴定了其中的两个,结构分别为3-O-[2′-O-β-D-吡喃葡萄糖基-3′-O-(2″-羟基-1″-羧乙氧基羧丙基)]-β-D-葡萄糖醛酸基齐墩果酸-28-O-β-D-吡喃葡萄糖苷(牛膝皂苷Ⅰ)和齐墩果酸3-O-[3′-O-(2″-羟基-1″-羧乙氧基羧丙基)]-β-D-葡萄糖醛酸苷(牛膝皂苷Ⅱ).结论牛膝皂苷Ⅰ和Ⅱ均为首次从牛膝中得到.     

浙江七叶树种子中三萜皂苷成分的分离和鉴定*

目的:研究浙江七叶树Aesculus chinensis Bunge var.chekiangensis(Huet Fang)Fang种子中的化学成分。方法:采用大孔吸附树脂柱色谱、高效液相色谱等方法进行分离和纯化,根据化合物的谱学数据鉴定其结构。结果:从浙江七叶树种子的70%乙醇提取物中分离得到3个三萜皂苷类化合物,分别鉴定为七叶树皂苷(escins)IVe和IVh及七叶树皂苷(aesculuside)A。结论:这3个化合物皆为首次从浙江七叶树种子中分离得到。     

Four new triterpenoid glycosides from the seed residue of Hippophae rhamnoides subsp. sinensis

Four new triterpenoid saponins (1–4) were isolated from the seed residue of Hippophae rhamnoides subsp. sinensis, named 3-O-[β-d-glucopyranosyl(1 → 2)-β-d-glucopyranosyl-(1 → 3)]-[α-l-rhamnopyranosyl-(1 → 2)]-α-l-arabinopyranosyl-13-ene-19-one-28-oic acid 28-O-β-d-glucopyranosyl ester (1), 3-O-[β-d-glucopyranosyl(1 → 2)-β-d-glucopyranosyl-(1 → 3)]-[α-l-rhamnopyranosyl-(1 → 2)]-α-l-arabinopyranosyl-13-ene-19-one-30-hydroxyolean-28-oic acid 28-O-β-d-glucopyranosyl ester (2), 3-O-[β-d-glucopyranosyl(1 → 2)-β-d-glucopyranosyl-(1 → 3)]-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranosyl-13-ene-19-one-28-oic acid 28-O-β-d-glucopyranosyl ester (3), and 3-O-[β-d-glucopyranosyl(1 → 2)-β-d-glucopyranosyl-(1 → 3)]-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranosyl-13-ene-19-one-30-hydroxyolean-28-oic acid 28-O-β-d-glucopyranosyl ester (4), and their structures were elucidated on the basis of spectroscopic and chemical methods.     

Three new triterpenoid saponins from Albizia julibrissin

Three new triterpenoid saponins, julibrosides A₅–A₇ (1–3), together with five known saponins (4–8), were isolated from the stem bark of Albizia julibrissin. Their structures were elucidated on the basis of extensive spectroscopic data analysis of MS, 1D and 2D NMR, and chemical methods. Compounds 7 and 8 were isolated from the genus Albizia for the first time. The new compounds showed no cytotoxicity and anti-inflammatory activity.     

光果甘草三萜皂苷类化学成分研究

采用聚酰胺—大孔树脂柱色谱、ODS中压柱色谱以及半制备液相色谱分离技术,对光果甘草(Glycyrrhiza glabra L.)水提取物中三萜皂苷类成分进行分离纯化,共获得10个三萜皂苷类化合物,依据理化性质及NMR、MS波谱数据鉴定化合物结构,分别鉴定为3β-O-[β-D-glucuronpyranosyl-(1→2...     

Two triterpenoid glycosides from the roots of Camellia oleifera and their cytotoxic activity

Two new triterpenoid saponins, oleiferoside N and oleiferoside O, were isolated from the EtOH extract from the roots of Camellia oleifera C. Abel. Their structures were elucidated as 16α-acetoxy-21β,22α-O-diangeloyloxy-23,28-dihydroxyolean-12-ene 3β-O-β-d-xylopyranosyl-(1 → 3)-α-l-arabinopyranosyl-(1 → 3)-β-d-glucuronopyranoside (1), 16α-acetoxy-21β-O-angeloyloxy-23,28-dihydroxy-22α-O-(2-methylbutanoyloxy)olean-12-ene 3β-O-β-d-xylopyranosyl-(1 → 3)-α-l-arabinopyranosyl-(1 → 3)-β-d-glucuronopyranoside (2), on the basis of spectroscopic analyses (IR, ESI-MS, HR-ESI-MS, 1D and 2D NMR) and acid hydrolysis. Both were characterized to be oleanane-type saponins with sugar moieties linked to C-3 of the aglycone. Cytotoxic activities of two saponins were evaluated against four human tumor cell lines (A549, B16, BEL-7402, and MCF-7) by using the MTT in vitro assay. Compounds 1 and 2 showed moderate cytotoxic activities toward the tested cell lines.     

Two new oleanane-type pentacyclic triterpenoid saponins from the husks of Xanthoceras sorbifolia Bunge

Two new triterpenoid saponins (1, 2) and a known saponin (3) were isolated from the husks of Xanthoceras sorbifolia Bunge., and their structures were elucidated as 3-O-β-D-glucopyranosyl(1 → 6)-[angeloyl(1 → 2)]-β-D-glucopyranosyl-28-O-α-L-rhamnopyranosyl(1 → 2)-[β-D-glucopyranosyl(1 → 6)]-β-D-glucopyranosyl-21β,22α-dihydroxyl-olean-12-ene (1), 3-O-β-D-glucopyranosyl-28-O-[β-D-glucopyranosyl(1 → 2)]-β-D-glucopyranosyl-21β,22α-dihydroxyl-olean-12-ene (2), and 3-O-β-D-glucopyranosyl-28-O-[α-L-rhamnopyranosyl(1 → 2)]-β-D-glucopyranosyl-21β,22α-dihydroxyl-olean-12-ene (3), on the basis of the spectral analysis of NMR and chemical methods. Cytotoxic assay indicated that none of them showed obvious inhibitory effect on the proliferation of two human tumor cell lines.     

Triterpenoid saponins from the stems of Clematis parviloba

Sixteen triterpenoid saponins (1–16) were isolated from the stems of Clematis parviloba, including a new compound, parvilobaside A (1), which was established as 23-O-acetyl-hederagenin-3-O-β-d-ribopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranoside on the basis of various spectroscopic techniques and chemical evidences. Among the isolated compounds, clematoside S (2) and α-hederin (4) showed moderate cytotoxic activities against four human tumor cell lines (HCT-8, Bel-7402, BGC-823, and A-2780) with IC₅₀ values in the range of 1.44–6.86 μg/ml.