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 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 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.     

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.     

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.     

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.     

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.     

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.     

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.     

<Emphasis Type="Italic">In vivo</Emphasis> anti-inflammatory effect of a new steroidal saponin,mannioside A,and its derivatives isolated from <Emphasis Type="Italic">Dracaena mannii</Emphasis>

A new steroidal saponin, mannioside A (1), was isolated from the stem bark of Dracaena mannii, together with the known pennogenin (2), pennogenin-3-O-beta-D-glucopyranoside (3) and pennogenin-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->3)]-beta-D-glucopyranoside (4). Their structures were determined using 1D-and 2D-NMR spectroscopy and mass spectrometry. Compounds 1 and 3 significantly inhibited carrageenan-induced paw edema in the rat; compound 4 was moderately active whereas 2 showed very weak activity.     

A novel steroidal glycoside, ophiofurospiside A from Ophiopogon japonicus (Thunb.) Ker-Gawl

A new furospirostanol saponin, ophiofurospiside A (1), was isolated together with the known steroidal glycosides 2, 3, and 4 from the tubers of Ophiopogon japonicus (Thunb.) Ker-Gawl. Using chemical and spectral analyses (IR, MS, 1D NMR, and 2D NMR), the structure of 1 was established as 26-O-beta-d-glucopyranosyl-(22S, 25R)-furospirost-5-ene-3beta, 17alpha, 26-triol-3-O-[alpha-l-rhamnopyranosyl-(1 --> 2)]-[beta-d-xylopyranosyl-(1 --> 4)]-glucopyranoside (1). Three known steroidal saponins 2-4 were identified on the basis of spectroscopic data.     

A new triterpenoid saponin with inhibition of luteal cell from the seeds of Vaccaria segetalis

A new triterpenoid saponin, named segetoside B, showing inhibition of luteal cell activity, has been isolated from the seeds of Vaccaria segetalis. On the basis of chemical reactions and spectral analyses, its structure has been established as 28-O-[beta-D-xylopyranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 2)]-[alpha-L-(5-O-acetyl)arabinofuranosyl-(1 --> 3)]-beta-D-(4-O-acetyl)fucopyranosyl-gypsogenin-3-O-beta-D-galactopyranosyl-(1 --> 2)-beta-D-(6-O-methyl ester)-glucuronopyranoside.     

Monodesmosidic saponins from Herniaria hirsuta

Two new monodesmosidic saponins, herniaria saponins E and F, were isolated from the aerial parts of Herniaria hirsuta. On the basis of chemical and spectral evidence, their structures were established to be 2-O-acetyl medicagenic acid 28-O-beta-D-xylopyranosyl- (1-->4)-alpha-L-rhamnopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->6)]-be ta- D-glucopyranoside (herniaria saponin E, 1) and medicagenic acid 28-O-beta-D-xylopyranosyl(1-->4)-alpha-L- rhamnopyranosyl(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D- glucopyranosyl-(1-->6)]-beta-D-glucopyranoside (herniaria saponin F, compound 2).     

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.     

New acylated triterpene saponins from Polygala tenuifolia willd

Two new acylated presenegenin glycosides E-onjisaponin H (5) and Z-onjisaponin (6) together with seven known saponins were isolated from the roots of Polygala tenuifolia Willd. Compounds 5 and 6 were obtained as a pair of isomers due to trans and cis-p-methoxycinnamoyl. Their structures were elucidated mainly by 2D-NMR techniques including 1H-1HCOSY, TOCSY, HSQC, HMBC as 3-O-(beta-D-glucopyranosyl) presenegenin 28-[O-beta-D-apiofuranosyl-(1 --> 3)-O-[beta-D-xylopyranosyl-(1 --> 4)]-O-alpha-L-rhamnopyranosyl-(1 --> 2)-O-[alpha-L-rhamnopyranosyl-(1 --> 3)]-4-O-[(E)-p-methoxycinnamoyl]-beta-D-fucopyranosyl] ester (5) and its (Z)-isomer (6).     

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.     

穿龙薯蓣总皂苷中甾体皂苷的分离与鉴定

目的研究穿龙薯蓣总皂苷中水溶性甾体皂苷,寻找新的生物活性化合物。方法用硅胶柱色谱、薄层色谱及高效液相色谱等进行分离,通过酸水解、理化常数和波谱学分析(IR,NMR,MS,HMQC,HMBC)鉴定化合物结构。结果从穿龙薯蓣总皂苷中分得2个甾体皂苷(1个水难溶性皂苷和1个水溶性皂苷),其化学结构分别鉴定为薯蓣皂苷元-3-O-{α-L-鼠李糖(1→2)-［β-D-葡萄糖(1→3)］}-β-D-葡糖皂苷(I),薯蓣皂苷元-3-O-［α-L-鼠李糖(1→3)-α-L-鼠李糖(1→4)-α-L-鼠李糖(1→4)］-β-D-葡糖皂苷(II)。结论II为首次从穿龙薯蓣中分离得到的新化合物,命名为穿龙薯蓣皂苷Dc。     

Three new triterpenoid saponins from the seeds of Aesculus turbinata

Three new triterpenoid saponins, named isoescins VIIa (1), VIa (2), and VIIIa (3), were isolated from the seeds of Aesculus turbinata and identified by spectroscopic analysis and chemical hydrolysis. Their structures were established as 21beta-O-tigloyl-28-O-acetylprotoaescigenin 3beta-O-[beta-d-galactopyranosyl(1 --> 2)][beta-d-glucopyranosyl(1 --> 4)]-beta-d-glucopyranosiduronic acid (Isoescin VIIa, 1), 21beta-O-(2-methylbutyryl)-28-O-acetylprotoaescigenin 3beta-O-[beta-d-glucopyranosyl(1 --> 2)] [beta-d-glucopyranosyl(1 --> 4)]-beta-d-glucopyranosiduronic acid (Isoescin VIa, 2), and 21beta-O-angeloyl-28-O-acetylbarringtogenol C 3beta-O-[beta-d-glucopyranosyl(1 --> 2)] [beta-d-glucopyranosyl(1 --> 4)]-beta-d-glucopyranosiduronic acid (Isoescin VIIIa, 3).     

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.