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 F(2) (3).     

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.     

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。     

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 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.     

Two new triterpenoid saponins from Symplocos Chinensis

Two new triterpenoid saponins, symplocososides X (1) and Y (2) have been isolated from the roots of Symplocos chinensis, and their structures elucidated as 21β-O- cinnamoyl-22α-O-(2-methylbutanoyl)-15α, 16α, 28-trihydroxyolean-12-ene-3β-O-[β-d-glucopyranosyl (1 → 2)]-α-l-arabinofuranosyl (1 → 4)-β-d-glucuronopyranoside (1) and 21β-O-cinnamoyl-22α-O-(2-methylbutanoyl)-15α, 16α, 28-trihydroxyolean-12-ene-3β-O-(3-O-acetyl)-[β-d-glucopyranosyl (1 → 2)]-α-l-arabinofuranosyl (1 → 4)-β-d-glucuronopyranoside (2) by spectral and chemical methods. Their antitumor activities have also been tested.     

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.     

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.     

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).     

Two new triterpenoid glycosides from the leaves of Anthocephalus chinensis

Nine compounds were isolated from the leaves of Anthocephalus chinensis by column chromatography on silica gel and Sephadex LH-20, and their structures were elucidated by spectroscopic techniques as clethric acid-28-O-β-d-glucopyranosyl ester (1), mussaendoside T (2), β-stigmasterol (3), hederagenin (4), ursolic acid (5), clethric acid (6), 3β,6β,19α,24-tetrahydroxyurs-12-en-28-oic acid (7), mussaendoside I (8), and cadambine (9). Compounds 1 and 2, and 7 and 8 were isolated from the plants of this genus for the first time, and compounds 1 and 2 were new triterpenoid glycosides.     

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.     

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。     

牛膝中三萜皂苷的研究

目的研究中药牛膝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.结果分离鉴定了2个酸性皂苷,结构分别为3-O-(3″-羧甲氧基-3-氧丙酮酸-3′-缩醛-4′-半缩酮)-β-D-吡喃葡萄糖醛酸基齐墩果酸-28-O-β-D-吡喃葡萄糖苷(牛膝皂苷Ⅲ,achyranthoside Ⅲ,1)和齐墩果酸3-O-(3″-羧甲氧基-3-氧丙酮酸-3′-缩醛-4′-半缩酮)-β-D-吡喃葡萄糖醛酸苷(牛膝皂苷Ⅳ,achyranthoside Ⅳ,2).结论两者均为首次从牛膝中得到.     

Three new triterpenoid saponins from the rhizomes of Impatiens pritzellii var. hupehensis

Three new triterpenoid saponins, impatiprins A-C (1-3), together with a known triterpenoid (4) and two known triterpenoid saponins (5, 6), were isolated from the rhizomes of Impatiens pritzellii Hook. f. var. hupehensis Hook. f. The structures of 1-3 were determined by 1D and 2D NMR, FAB-MS techniques and chemical methods. Compounds 1 and 2 showed weak cytotoxicities against S-180, HeLa and HepG2 cell lines.     

Three new acylated flavone C-glycosides from the flowers of Trollius chinensis

Three new flavone C-glycosides with the substitution of the unusual acyl, 2″-O-veratroylisoswertisin (1), 3″-O-2-methylbutyrylisoswertiajaponin (2), and 3″-O-2-methylbutyrylvitexin (3), together with the known compounds of 2″-O-2-methylbutyrylisoswertisin (4), 3″-O-2-methylbutyrylisoswertisin (5), and trollisin I (6) were isolated from the antibacterial fraction of the aqueous extract of the flowers of Trollius chinensis. The structural elucidations of these compounds were carried out by a detailed analysis of the NMR and MS spectra.     

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.     

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.