A new triterpenoid saponin from Albizia julibrissin Durazz

A new triterpenoid, saponin hehuanoside A, was isolated together with the known triterpenoid saponins 2, 3, and 4 from the stem bark of Albizia julibrissin. With the help of chemical and spectral analyzes (IR, MS, 1D-NMR, and 2D-NMR), the structure of the new triterpenoid saponin was elucidated as 21-O-[(6S)-2-trans-2,6-dimethyl-6-O-beta-d-quinovopyranosyl-2,7-octadienoyl]-3-O-beta-d-xylopyranosyl-(1 --> 2)-beta-d-fucopyranosyl-(1 --> 6)-beta-d-2-deoxy-2-acetamidoglucopyrasyl acacic acid 28-O-alpha-l-arabinofuranosyl-(1 --> 4)-[-beta-d-glucopyranosyl-(1 --> 3)]-alpha-l-rhamnopyranosyl-(1 --> 2)-beta-d-glucopyranosyl ester (1). Three known triterpenoid saponins 2-4 were identified on the basis of spectroscopic data.     

A novel triterpenoid saponin from Polygala tenuifolia Willd

A new triterpenoid saponin, tenuifoside A, was isolated together with three known triterpenoid saponins 2, 3, and 4 from the roots of Polygala tenuifolia Willd. With the help of chemical and spectral analyses (IR, MS, 1D-NMR, and 2D-NMR), the structure of the new saponin was elucidated as 3-O-beta-d-glucopyranosyl presenegenin 28-O-beta-d-xylopyranosyl-(1 --> 3)-beta-d-xylopyranosyl-(1 --> 4)-[beta-D-apiofuranosyl-(1 --> 3)]-alpha-L-rhamnopyranosyl-(1 --> 2)-[4-O-p-methoxycinnamoyl]-[alpha-l-rhamnopyranosyl-(1 --> 3)]-beta-d-fucopyranosyl ester (1). Three known triterpenoid saponins (2-4) were identified on the basis of spectroscopic data.     

A novel triterpenoid saponin from Polygala tenuifolia Willd

A new triterpenoid saponin, tenuifoside A, was isolated together with three known triterpenoid saponins 2, 3, and 4 from the roots of Polygala tenuifolia Willd. With the help of chemical and spectral analyses (IR, MS, 1D-NMR, and 2D-NMR), the structure of the new saponin was elucidated as 3-O-beta-d-glucopyranosyl presenegenin 28-O-beta-d-xylopyranosyl-(1 --> 3)-beta-d-xylopyranosyl-(1 --> 4)-[beta-d-apiofuranosyl-(1 --> 3)]-alpha-l-rhamnopyranosyl-(1 --> 2)-[4-O-p-methoxycinnamoyl]-[alpha-l-rhamnopyranosyl-(1 --> 3)]-beta-d-fucopyranosyl ester (1). Three known triterpenoid saponins (2-4) were identified on the basis of spectroscopic data.     

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.     

Two new triterpenoid saponins from Pulsatilla cernua (Thunb.) Bercht. et Opiz

Two new triterpenoid saponins, named cernuaside C and D, have been isolated from Pulsatilla cernua (Thunb.) Bercht. et Opiz. The structures of the two new triterpenoid saponins were elucidated as 3-O-beta-D-xylopyranosyl(1 --> 2)-[alpha-L-rhamnopyranosyl(1 --> 3)]-alpha-L-arabinopyranosyl oleanolic acid 28-alpha-L-rhamnopyranosyl(1 --> 4)-beta-D-glucopyranosyl(1 --> 6)-beta-D-glucopyranoside. (1) and 3-O-alpha-L-arabinopyranosyl (1 --> 3)-alpha-L-rhamnopyranosyl(1 --> 2)-alpha-L-arabinopyranosyl oleanolic acid 28-O-beta-D-glucopyranoside (2) by 1D, 2D-NMR techniques, ESI-MS analysis as well as chemical methods.     

Triterpenoid saponins from Stauntonia chinensis

A new triterpenoid saponin, named stauntoside A (1) along with four known saponins (2,3,4,5) was isolated from Stauntonia chinensis DC., (Lardizabalaceae). Their structures were elucidated by spectroscopic analysis and chemical methods as 3-O-alpha-L-arabinopyranosyl-30-norhederagenin -28-O-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (1), 3-O-alpha-L-arabinopyranosyl-30- norhederagenin-28-O-alpha-L-rhamnopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (2), 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl-30-norhederagenin-28-O-alpha-L- rhamnopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (3), 3-O-alpha-L- arabinopyranosyl-hederagenin-28-O-alpha-L-rhamnopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 6)-beta-D- glucopyranosyl ester (4), 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl-hederagenin -28-O-alpha-L-rhamnopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (5). The (1)H and (13)C NMR data for Glycoside L-G1 or Sinofoside A are paradox in the reported before. Thus, the structure elucidation of saponin 2, known as Glycoside L-G1 or Sinofoside A, was discussed and the unambiguous assignments were given.     

A novel triterpenoid saponin from Polygala tenuifolia Willd.

A new triterpenoid saponin, tenuifoside A, was isolated together with three known triterpenoid saponins 2, 3, and 4 from the roots of Polygala tenuifolia Willd. With the help of chemical and spectral analyses (IR, MS, 1D-NMR, and 2D-NMR), the structure of the new saponin was elucidated as 3-O-β-d-glucopyranosyl presenegenin 28-O-β-d-xylopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 4)-[β-d-apiofuranosyl-(1 → 3)]-α-l-rhamnopyranosyl-(1 → 2)-[4-O-p-methoxycinnamoyl]-[α-l-rhamnopyranosyl-(1 → 3)]-β-d-fucopyranosyl ester (1). Three known triterpenoid saponins (2–4) were identified on the basis of spectroscopic data.     

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.     

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).     

Cytotoxic triterpenoid saponins from Vaccaria segetalis

By the guidance of bioassay, one new cytotoxic triterpenoid saponin, 3-O-[beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl] quillaic acid 28-O-beta-D-glucopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-fucopyranosyl-(1-->4)]-beta-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 ((1)H NMR, (13)C NMR, TOCSY, (1)H-(1)H 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 IC(50) values in the range 0.1-12.9 microM.     

Four new triterpenoid saponins from Ardisia gigantifolia Stapf. and their cytotoxic activity

Four new oleanane-type triterpenoid saponins, cyclamiretin A 3beta-O-alpha-L-rhamnopyranosyl-(1 --> 3)-[beta-D-xylopyranosyl-(1 --> 2)]-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-glucopyranosyl-(1 --> 2)]-alpha-L-arabinopyranoside (1), cyclamiretin A 3beta-O-alpha-L-rhamnopyranosyl-(1 --> 3)-[beta-D-glucopyranosyl-(1 --> 3)-beta-D-xylopyranosyl-(1 --> 2)]-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-glucopyranosyl-(1 --> 2)]-alpha-L-arabinopyranoside (2), cyclamiretin A 3beta-O-alpha-L-rhamnopyranosyl-(1 --> 3)-[beta-D-xylopyranosyl-(1 --> 2)]-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-6-O-acetylglucopyranosyl-(1 --> 2)]-alpha-L-arabinopyranoside (3) and 3beta-O-[alpha-L-rhamnopyranosyl-(1 --> 3)-[beta-D-xylopyranosyl-(1 --> 2)]-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-glucopyranosyl-(1 --> 2)]-alpha-L-arabinopyranoside]-16,28-dihydroxy-30-acetoxyoleana-12-en (4), along with one known triterpene saponin and ardisiacrispin A (5) were isolated from the rhizome of Ardisia gigantifolia. Their structures were established with the help of extensive spectroscopic techniques. Furthermore, the inhibitory effects of compounds on tumor cells (MTT based) in vitro were evaluated, and compounds 1, 2, and 5 showed potent anti-tumor activities.     

Triterpenoid saponins from Dipsacus asper and their activities in vitro

Two new triterpenoid saponins 1 and 2, along with six known saponins 3-8, were isolated from the roots of Dipsacus asper. The structures of new compounds were established as 3-O-β-d-glucopyranosyl-(1?→?4)-[α-l-rhamnopyranosyl-(1?→?3)]-β-d-glucopyranosyl-(1?→?3)-α-l-rhamnopyranosyl-(1?→?2)-α-l-arabinopyranosyl-hederagenin-28-O-β-d-glucopyranoside (dipsacus saponin J, 1) and 3-O-α-l-arabinopyranosyl-hederagenin-28-O-β-d-glucopyranosyl-(1?→?6)-β-d-glucopyranosyl-(1?→?6)-β-d-glucopyranoside (dipsacus saponin K, 2). The structures were determined by extensive analysis of their spectroscopic data. Compounds 6 and 7 could significantly stimulate UMR106 cell proliferation and increase alkaline phosphatase activities in UMR106 cell at the concentration of 4?μM.     

A New Bidesmosidic Triterpenoidal Saponin from the Roots of Symphytum officinale

A new triterpenoidal saponin having hederagenin as the aglycone was isolated from the roots of SYMPHYTUM OFFICINALE L. The structure of this saponin was elucidated by FAB-MS, (1)H-, (13)C-NMR, 2D-NMR analyses and chemical studies as 3- O-[beta- D-glucopyranosyl-(1-->4)-alpha- L-arabinopyranosyl]-hederagenin 28- O-[beta- D-glucopyranosyl-(1-->6)-beta- D-glucopyranosyl] ester.     

卵叶银莲花全草中的新三萜皂苷

目的　对卵叶银莲花（Anemone begoniifolia Lévl.et Vant）全草的的三萜皂苷成分进行分离和结构鉴定。方法　通过正相和反相硅胶柱色谱分离甲醇提取物中的三萜皂苷;利用各种波谱技术并结合化学降解方法鉴定其化学结构。结果　分离鉴定了1个二元混合物和2个单体,二元混合物中的2个成分分别鉴定为3-O-β-D-吡喃葡糖(1→2)-α-L-吡喃阿拉伯糖基-齐墩果酸-28-O-α-L-吡喃鼠李糖(1→4)-β-D-吡喃葡糖(1→6)-β-D-吡喃葡糖苷(1)和3-O-β-D-吡喃葡糖(1→3)-α-L-吡喃阿拉伯糖基-齐墩果酸-28-O-α-L-吡喃鼠李糖(1→4)-β-D-吡喃葡糖(1→6)-β-D-吡喃葡糖苷(2),2个单体分别鉴定为23-O-丙二酸单甲酯单酰基-常春藤配基-28-O-α-L-吡喃鼠李糖(1→4)-β-D-吡喃葡糖(1→6)-β-D-吡喃葡糖苷(3)和3-O-丙二酸单甲酯单酰基-常春藤配基-28-O-α-L-吡喃鼠李糖(1→4)-β-D-吡喃葡糖(1→6)-β-D-吡喃葡糖苷(4)。结论　化合物2,3和4为新三萜皂苷,分别命名为卵叶银莲花苷A,B和C。     

Steroidal glycosides from tubers of Ophiopogon japonicus

A new steroidal saponin, named ophiopogonin E (1), has been isolated from the tubers of Ophiopogon japonicus, along with five known steroidal saponins (2-6). The structure of the new steroidal glycoside was characterized by spectroscopic analysis and acid-catalyzed hydrolysis as pennogenin 3-O-beta-D-xylopyranosyl (1 --> 4)-beta-D-glucopyranoside (1).     

Triterpenoid saponins from Androsace umbellata and their anti-proliferative activities in human hepatoma cells

Two new triterpenoid saponins, along with five known ones, were isolated from the EtOH extract of the whole plants of Androsace umbellata. The structures of the new triterpenoid saponins were identified as 3- O-[ beta- D-xylopyranosyl-(1-->2)- beta- D-glucopyranosyl-(1-->4)-[ beta- D-glucopyranosyl-(1-->2)]- alpha- L-arabinopyranosyl]-3 beta-hydroxy-13 beta,28-epoxy-16-oxo-oleanan-30-al ( 1) and 3- O- beta- D-xylopyranosyl-(1-->2)- beta- D-glucopyranosyl-(1-->4)- alpha- L-arabinopyranosyl-3 beta-hydroxy-13 beta,28-epoxy-16-oxo-oleanan-30-al ( 2) on the basis of their spectral and chemical properties. All these compounds showed significant cytotoxic activities in human hepatoma cells.     

Ginsenoside-Ia: a novel minor saponin from the leaves of Panax ginseng

A new saponin, named ginsenoside-I (a), was isolated from leaves of Panax Ginseng, together with nine known saponins, and its structure was elucidated as 3beta,6alpha,12beta,20(S)-tetrahydroxyldammar-24(25)-ene (20- O-beta-D-glucopyranosyl)-3-O-beta-D-glucopyranoside on the basis of chemical and 2D-NMR methods.     

Three new saponins from the leaves of Ilex hylonoma

Three new triterpenoid saponins, hylonosides III-V (1-3) have been isolated, along with three known oleanolic acid saponins (4-6), from the methanol extract of leaves of Ilex hylonoma. The structures were elucidated using a combination of homo- and hetero-nuclear 2D NMR techniques (COSY, TOCSY, NOESY, HMQC and HMBC) and negative FAB-MS. The new compounds were characterized as 3-O-beta-D-glucopyranosyl-(1 --> 4)-beta-D-glucuronopyranosyl siaresinolic acid-28-O-beta-D-glucopyranosyl ester (1), 3-O-beta-D-glucopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucuronopyranosyl siaresinolic acid-28-O-beta-D-glucopyranosyl ester (2), 3-O-beta-D-glucopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucuronopyranosyl oleanolic acid-28-O-beta-D-glucopyranosyl ester (3).     

Isolation of a new saponin and cytotoxic effect of saponins from the root of Platycodon grandiflorum on human tumor cell lines

A novel triterpenoid saponin, deapioplatycoside E (1) was isolated from the root extract of Platycodon grandiflorum, together with the seven known saponins 2 - 8, i. e., platycoside E (2), deapioplatycodin D3 (3), platycodin D3 (4), polygalacin D2 (5), platycodin D2 (6), deapioplatycodin D (7) and platycodin D (8). The structure of the new saponin 1 was determined on the basis of spectral analysis and chemical evidence. The crude saponin fraction (ED50: ca. 10 - 15 microg/mL) and compounds 6 - 8 (ED50: ca. 4 - 18 microg/mL) exhibited significant inhibition on the proliferation of five kinds of cultured human tumor cell lines, i. e., A549 (non-small cell lung), SK-OV-3 (ovary), SK-MEL-2 (melanoma), XF498 (central nerve system) and HCT-15 (colon), in vitro.     

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。