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 21beta-O- cinnamoyl-22alpha-O-(2-methylbutanoyl)-15alpha, 16alpha, 28-trihydroxyolean-12-ene-3beta-O-[beta-D-glucopyranosyl (1 --> 2)]-alpha-L-arabinofuranosyl (1 --> 4)-beta-D-glucuronopyranoside (1) and 21beta-O-cinnamoyl-22alpha-O-(2-methylbutanoyl)-15alpha, 16alpha, 28-trihydroxyolean-12-ene-3beta-O-(3-O-acetyl)-[beta-D-glucopyranosyl (1 --> 2)]-alpha-L-arabinofuranosyl (1 --> 4)-beta-D-glucuronopyranoside (2) by spectral and chemical methods. Their antitumor activities have also been tested.     

Two new triterpenoid saponins from Sarcandra glabra

Two new triterpenoid saponins, named sarcandroside A and B, have been isolated from Sarcandra glabra (Thunb) Nakai. Their structures have been established as 3β,19α,20β-trihydroxyurs-11,13 (18)-diene-28,20β-lactone-3-O-β-d-glucopyranosyl (1 → 3)-[α-l-rhamnopyranosyl(1 → 2)]-β-d-xylopyranoside (1) and 3-O-β-d-glucopyranosyl (1 → 3)-[α-l-rhamnopyranosyl(1 → 2)]-β-d-xylopyranosyl-pomolic acid 28-O-β-d-glucopyranosyl ester (2) by means of spectral and chemical methods.     

Two new triterpenoid saponins from Ardisia crenata

Two new triterpenoid saponins, ardisicrenoside K (1) and ardisicrenoside L (2), have been isolated from the roots of Ardisia crenata Sims. Their structures have been determined as 3β-O-{α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-[β-d-glucopyranosyl-(1 → 2)]-α-l-arabinopyranosyl}-13β,28-epoxy-16-oxo-30,30-dimethoxyoleanane and 3β-O-{β-d-xylopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-[β-d-glucopyranosyl-(1 → 2)]-α-l-arabinopyranosyl}-13β,28-epoxy-16α,20-dihydroxyoleanane by means of chemical evidences and spectral analysis. Their weak anti-fungal activity against the plant pathogenic fungus Pyricularia oryzae was evaluated in vitro.     

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 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.     

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.     

Four new triterpenoid saponins from Ilex Godajam

Four new triterpenoid saponins, godosides A - D ( 1 - 4 ), along with eight known saponins, have been isolated from the fresh aerial parts of Ilex godajam . Structure elucidation of 1 - 4 was based on NMR, MS, IR and chemical analyses.     

Four new triterpenoid saponins from Ilex godajam

Four new triterpenoid saponins, godosides A - D ( 1 - 4 ), along with eight known saponins, have been isolated from the fresh aerial parts of Ilex godajam . Structure elucidation of 1 - 4 was based on NMR, MS, IR and chemical analyses.     

黄花败酱中三萜皂苷类成分的分离鉴定

目的 研究黄花败酱中的化学成分.方法 将黄花败酱全草的乙醇提取物经大孔树脂、硅胶、ODS柱分离得到6个化合物,通过(1H、13CNMR、ESI-MS等分析和化学方法进行结构鉴定.结果 6个化合物分别被鉴定为3-O-β-D-吡喃木糖-(1→3)-α-L-吡喃鼠李糖-(1→2)-α-L-吡喃阿拉伯糖-常春藤皂苷元-28-O-β-D-吡喃葡萄糖(6→1)-β-D-吡喃葡萄糖-(4→1)-α-L-吡喃鼠李糖酯苷(Ⅰ)、3-O-β-D-α-L-吡喃鼠李糖-(1→2)-α-L-吡喃阿拉伯糖-常春藤皂苷元-28-O-β-D-吡喃葡萄糖(6→1)-β-D-吡喃葡萄糖-(4→1)-α-L-吡喃鼠李糖酯苷 (Ⅱ)、齐墩果酸-3-α-L-吡喃阿拉伯糖-(2→1)-α-L-吡喃鼠李糖-(3→1)-O-β-D-吡喃木糖苷(Ⅲ)、3-O-β-D-吡喃木糖-(1→3)-α-L-吡喃鼠李糖-(1→2)-α-L-吡喃阿拉伯糖-齐墩果酸-28-O-β-D-吡喃葡萄糖酯苷 (Ⅳ)、齐墩果酸-3-O-β-D-吡喃木糖-(2→1)-α-L-吡喃鼠李糖苷(Ⅴ)、常春藤皂苷元-3-O-α-L-吡喃阿拉伯糖-(2→1)-α-L-吡喃鼠李糖苷 (Ⅵ).结论 化合物Ⅳ为一个新的天然产物,化合物Ⅰ和Ⅲ为首次从该植物中分离得到.     

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).     

Five new cytotoxic triterpenoid saponins from the roots of Symplocos chinensis

Five new triterpenoid saponins, named symplocososides G-K, were isolated from the roots of Symplocos chinensis. Their structures were elucidated by spectral and chemical methods as symplocososide G, 3beta-O-{[beta- D-glucopyranosyl(1-->2)][alpha-L-arabinofuranosyl(1-->4)]-beta-D-(3-O-acetyl)-glucuronopyranosyl}-21beta- O-[(2 Z)-3,7-dimethyl-2,6-octadienoyl]-22 alpha-O-(2-methylbutanoyl)-R1-barrigenol, symplocososide H, 3beta-O-{[beta-D-glucopyranosyl(1-->2)][alpha-L-arabinofuranosyl(1-->4)]- beta-D-(3-O-acetyl)-glucuronopyranosyl}-21beta-O-[(2E)3,7-dimethyl-2,6-octadienoyl]-22alpha-O-(2-methylbutanoyl)-R1-barrigenol, symplocososide I, 3beta-O-{[beta-D-glucopyranosyl(1-->2)][ alpha-L-arabinofuranosyl(1-->4)]-beta-D-(3- O-acetyl-6-O-methyl)-glucuronopyranosyl}-21beta-O-[(2 Z)3,7-dimethyl-2,6-octadienoyl]-22alpha-O-(2-methylbutanoyl)-R1-barrigenol, symplocososide J, 3 beta-O-{[ beta-D-glucopyranosyl(1-->2)][alpha-L-arabinofuranosyl(1-->4)]-beta-D-(3- O-acetyl)-glucuronopyranosyl}-21beta-O-[(2 Z)3,7-dimethyl-2,6-octadienoyl]-22alpha-O-benzoyl-R1-barrigenol, and symplocososide K, 3beta-O-{[beta-D-glucopyranosyl (1-->2)][alpha-L-arabinofuranosyl(1-->4)]- beta-D-(3-O-acetyl-6-O-methyl)-glucuronopyranosyl}-21beta-O-[(2Z)3,7-dimethyl-2,6-octadienoyl]-22alpha-O-benzoyl-R1-barrigenol. Symplocososides G-K showed significant cytotoxicity against cancer cell lines KB, HCT-8, Bel-7402, BGC-823 and A549 with IC50 values ranging from 0.82 microM to 5.09 microM, except for symplocososide I against cancer cell lines KB, BGC-823, A549 and symplocososide K against cancer cell line BGC-823 with IC50 values >10.00 microM.     

Two new triterpenoid saponins from Sarcandra glabra

Two new triterpenoid saponins, named sarcandroside A and B, have been isolated from Sarcandra glabra (Thunb) Nakai. Their structures have been established as 3beta,19alpha,20beta-trihydroxyurs-11,13 (18)-diene-28,20beta-lactone-3-O-beta-D-glucopyranosyl (1 --> 3)-[alpha-L-rhamnopyranosyl(1 --> 2)]-beta-D-xylopyranoside (1) and 3-O-beta-D-glucopyranosyl (1 --> 3)-[alpha-L-rhamnopyranosyl(1 --> 2)]-beta-D-xylopyranosyl-pomolic acid 28-O-beta-D-glucopyranosyl ester (2) by means of spectral and chemical methods.     

Two new triterpenoid saponins from Ilex cornuta

Two new triterpenoid saponins (1 and 2) were isolated from the stems of Ilex cornuta, along with two known triterpenoids (3 and 4). The structures of compounds 1 and 2 were determined as ursane-12,19-diene-28-oic acid 3β-O-β-d-glucuronopyranoside-6-O-methyl ester (1), 3α,23α-dihydroxy-olean-9(11),12-diene-28-oic acid 28-O-β-d-glucopyranosyl ester (2), on the basis of hydrolysis and spectral evidence, including 1D and 2D NMR and high resolution electrospray ionization mass spectrometry (HR-ESI-MS) analyses. Protective effects of compounds 1–4 were tested against H₂O₂-induced H9c2 cardiomyocyte injury, and the data showed that all these compounds had no cell-protective effect.     

Two new triterpenoid saponins from Ardisia crenata

Two new triterpenoid saponins, ardisicrenoside K (1) and ardisicrenoside L (2), have been isolated from the roots of Ardisia crenata Sims. Their structures have been determined as 3beta-O-[alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-glucopyranosyl-(1 --> 2)]-alpha-L-arabinopyranosyl]-13beta,28-epoxy-16-oxo-30,30-dimethoxyoleanane and 3beta-O-[beta-D-xylopyranosyl-(1 --> 2)-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-glucopyranosyl-(1 --> 2)]-alpha-L-arabinopyranosyl]-13beta,28-epoxy-16alpha,20-dihydroxyoleanane by means of chemical evidences and spectral analysis. Their weak anti-fungal activity against the plant pathogenic fungus Pyricularia oryzae was evaluated in vitro.     

Two new triterpenoid glycosides from Cyclocarya paliurus

Two new dammarane triterpenoid glycosides named cyclocarosides B (1) and C (2) were isolated from the leaves of Cyclocarya paliurus. Based on FAB-MS, HRESI-MS, IR, ¹H NMR, ¹³C NMR, and 2D-NMR (HMQC, HMBC, COSY, ROESY) data, the structures of cyclocarosides B (1) and C (2) were elucidated as (20S,24R)-epoxydammarane (3β,12β)-25-hydroxyl-12-O-β-d-quinovopyranosyl-3-O-β-d-quinovopyranoside (1), and (20S,24R)-epoxydammarane (3β, 12β)-25-hydroxyl-12-O-α-l-arabinopyranosyl-3-O-(5′-O-acetyl)-α-l-arabinofuranoside (2).     

Two new triterpenoid saponins from Caragana microphylla seeds

Two new triterpenoid saponins, caraganins A and B (1 and 2), structurally characterized by a 22-oxo group, were isolated from the seeds of Caragana microphylla Lam., together with their n-butyl esters as artifacts (1a and 2a). Their structures and configurations were elucidated by detailed spectroscopic analyses on the basis of NMR, IR, and MS data. Compounds 1a and 2a exhibited potent antibacterial activity against Staphylococcus aureus and Bacillus subtilis with minimum inhibitory concentration values ranging from 3.125 to 6.25 μg/ml.     

Cytotoxic triterpenoid saponins from Vaccaria segetalis

By the guidance of bioassay, one new cytotoxic triterpenoid saponin, 3-O-[β-d-galactopyranosyl-(1 → 2)-β-d-glucuronopyranosyl] quillaic acid 28-O-β-d-glucopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-[β-d-fucopyranosyl-(1 → 4)]-β-d-fucopyranoside (1), and five known cytotoxic triterpenoid saponins, vaccaroside E (2), vaccaroside G (3), vaccaroside B (4), segetoside H (5) and segetoside I (6), were isolated from Vaccaria segetalis. Their structures were established on the basis of ESI-MS, IR, extensive NMR (¹H NMR, ¹³C NMR, TOCSY, ¹H–¹H COSY, DEPT, HMQC, HMBC and ROESY) analyses, chemical degradation, and by comparing with previously reported data. Compounds 1–6 showed moderate cytotoxic activities against LNcap, P-388 and A-549 cell lines with IC₅₀ values in the range 0.1–12.9 μM.     

Two new steroidal saponins from Tribulus terrestris

Two new steroidal saponins and two known flavonoid glycosides were isolated from the fruits of Tribulus terrestris. Their structures were assigned by spectroscopic analysis and chemical reaction as 26-O-β-d-glucopyranosyl-(25R)-5α-furostan-12-one-3β,22α,26-triol-3-O-β-d-glucopyranosyl (1 → 2)-β-d-glucopyranosyl(1 → 4)-β-d-galactopyranoside (1), 26-O-β-d-glucopyranosyl-(25S)-5α-furostan-22-methoxy-2α,3β,26-triol-3-O-β-d-glucopyranosyl(1 → 2)-β-d-glucopyranosyl(1 → 4)-β-d-galactopyranoside (2), kaempferol-3-gentiobioside (3), and isorhamnetin-3-gentiobioside (4).     

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.