Glandulosides A-D, triterpene saponins from Acanthophyllum glandulosum

Four novel triterpenoid saponins, glandulosides A (1), B (2), C (3), and D (4), together with two known saponins (5 and 6) have been isolated from the roots of Acanthophyllum glandulosum. Their structures were elucidated using a combination of homo- and heteronuclear 2D NMR techniques (COSY, TOCSY, NOESY, HSQC, and HMBC) and by FABMS. The new compounds were characterized as 23-O-beta-D-galactopyranosylgypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[beta-d-galactopyranosyl-(1-->6)]-beta-D-galactopyranoside (1), 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl-(1-->2)-3-O-acetyl-beta-D-fucopyranoside (2), 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-3,4-di-O-acetyl-beta-D-fucopyranoside (3), and 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl-(1-->2)-[3-O-acetyl-beta-D-quinovopyranosyl-(1-->4)]-beta-D-fucopyranoside (4).     

Three new triterpene saponins from two species of Carpolobia

Three new acetylated triterpene saponins 1-3 were isolated from the roots of Carpolobia alba and C. lutea. Their structures were established mainly by 2D NMR techniques as 3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-galactopyranosyl-(1-->4)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-(3,4-di-O-acetyl)-beta-D-fucopyranosyl ester, 3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-galactopyranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->3)]-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-(3,4-di-O-acetyl)-beta-D-fucopyranosyl ester, and 3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-xylopyranosyl-(1-->4)-[beta-D-apiofuranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-(3,4-di-O-acetyl)-beta-D-fucopyranosyl ester, respectively.     

Junceosides A-C, new triterpene saponins from Arenaria juncea.

Three novel triterpenoid saponins, junceosides A (1), B (2), and C (3), together with two known saponins have been isolated from the roots of Arenaria juncea. Their structures were elucidated using a combination of homo- and heteronuclear 2D NMR techniques (COSY, TOCSY, NOESY, HSQC, and HMBC) and by FABMS. The new compounds were characterized as 3-O-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-glucopyranosyl(1-->3)-[beta-D-xylopyranosyl-(1-->4)]-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (1), 3-O-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (2), and 3-O-beta-D-xylopyranosyl-(1-->3)-[beta-D-galactopyranosyl-(1-->2)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (3).     

Two new biologically active triterpene saponins from Acanthophyllum squarrosum

Two novel triterpenoid saponins (1 and 2) have been isolated from the roots of Acanthophyllum squarrosum. The structures were established mainly by a combination of 2D NMR techniques as 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-be ta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3 )-b eta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L- rhamnopyranosyl-(1-->3)]-beta-D-fucopyranoside (1) and 3-O-beta-D-glucopyranosylgypsogenin-28-O-alpha-L-rhamnopyranosyl-( 1-- >2)-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->6 )]- beta-D-glucopyranoside (2). Compound 1 showed a moderate concentration-dependent immunomodulatory effect in an in vitro lymphocyte proliferation assay.     

Four new triterpenoidal saponins acylated with one monoterpenic acid from Gleditsia sinensis.

Four new oleanane-type triterpenoidal glycosides, named gleditsiosides A-D (1-4), were isolated from the anomalous fruits of Gleditsia sinensis. Using modern NMR techniques, including DQF-COSY, HETCOR, HOHAHA, HMBC, and ROESY experiments and MS analysis as well as chemical methods, their structures were determined as 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)- bet a-D-glucopyranosyl oleanolic acid 28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha- L-rhamnopyranosyl-(1-->2)-[(6S,2E)-6-hydroxy-2,6-dimethyl-2, 7-octadienoyl-(1-->6)]-beta-D-glucopyranosyl ester (1); 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)- bet a-D-glucopyranosyl oleanolic acid 28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha- L-rhamnopyranosyl-(1-->2)-[(2E)-2-hydroxylmethyl-6-hydroxy-6-methy l-2 ,7-octadienoyl-(1-->6)]-beta-D-glucopyranosyl ester (2); 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)- bet a-D-glucopyranosyl echinocystic acid 28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[beta- D-galactopyranosyl-(1-->2)]-alpha-L-rhamnopyranosyl-(1-->2)-[(2E)-2-h ydroxylmethyl-6-hydroxy-6-methyl-2, 7-octadienoyl-(1-->6)]-beta-D-glucopyranosyl ester (3); and 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)- bet a-D-glucopyranosyl echinocystic acid 28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[beta- D-galactopyranosyl-(1-->2)]-alpha-L-rhamnopyranosyl-(1-->2)-[(6S, 2E)-6-hydroxy-2,6-dimethyl-2, 7-octadienoyl-(1-->6)]-beta-D-glucopyranosyl ester (4).     

Four new triterpenoid saponins from Conyza blinii

Three new bisdesmosidic saponins named conyzasaponins A, B, and C (1-3) and one new monodesmosidic saponin, conyzasaponin G (4), were isolated from the aerial parts of Conyza blinii. Their structures were elucidated on the basis of extensive NMR (DEPT, DQF-COSY, HOHAHA, HMQC, HMBC, and NOESY) and MS studies. Compounds 1-3 share a common prosapogenin, bayogenin 3-O-beta-D-xylopyranosyl-(1-->3)-beta-D-glucopyranoside, which is identical with conyzasaponin G (4), and differ in the structures of the ester-linked sugar moieties at C-28. Conyzasaponin A (1) is the 28-O-beta-D-apiofuranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl ester, conyzasaponin B (2), the 28-O-beta-D-apiofurano- syl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl ester, and conyzasaponin C (3), the 28-O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[beta-D-apiofuranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl ester of the prosapogenin, respectively.     

Gleditsiosides N-Q, new triterpenoid saponins from Gleditsia sinensis.

The structures of gleditsiosides N, O, P, and Q (1-4), isolated from anomalous fruits of Gleditsia sinensis, were characterized as novel complex bisdesmosidic triterpenoid glycosides acylated with monoterpenoid units, by means of extensive 1D and 2D NMR studies. The four compounds shared a common structural feature with a trisaccharide [(beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)-be ta- D-glucopyranoside)] affixed to C-3 and a tetrasaccharide [(beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-r hamnopyranosyl-(1-->2)-beta-D-glucopyranosyl ester)] attached to C-28. Gleditsioside P (3) is the first saponin of this type found to date bearing three monoterpenoid units.     

Biologically active triterpene saponins from callus tissue of Polygala amarella.

A new bioactive saponin (1), together with a known saponin (polygalasaponin XXVIII) has been isolated from the callus tissue culture of Polygala amarella. Based on spectroscopic data, especially direct and long-range heteronuclear 2D NMR analysis and on chemical transformations, the structure of 1 was elucidated as 3-O-beta-D-glucopyranosyl presenegenin-28-O-beta-D-galactopyranosyl-(1 --> 3)-beta-D-xylopyranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 3)]-beta-D-fucopyranoside. Both saponins showed significant immunological properties based on the enhancement of granulocyte phagocytosis in vitro.     

Acylated preatroxigenin glycosides from Atroxima congolana

Six new acylated bisdesmosidic preatroxigenin saponins named atroximasaponins E1, E2 (1, 2), F1, F2 (3, 4), and G1, G2 (5, 6) were isolated as three inseparable mixtures of the trans- and cis-p-methoxycinnamoyl derivatives, from the roots of Atroxima congolana. Their structures were established through extensive NMR spectroscopic analysis as 3-O-beta-D-glucopyranosylpreatroxigenin-28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->3)]-[4-O-trans-p-methoxycinnamoyl]-beta-D-fucopyranoside (atroximasaponin E1, 1), and its cis-isomer, atroximasaponin E2 (2), 3-O-beta-D-glucopyranosylpreatroxigenin-28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[6-O-acetyl-beta-D-glucopyranosyl-(1-->3)]-[4-O-trans-p-methoxycinnamoyl]-beta-D-fucopyranoside (atroximasaponin F1, 3), and its cis-isomer, atroximasaponin F2 (4), 3-O-beta-D-glucopyranosylpreatroxigenin-28-O-beta-D-apiofuranosyl-(1-->3)-[alpha-l-rhamnopyranosyl-(1-->2)]-[4-O-trans-p-methoxycinnamoyl]-beta-D-fucopyranoside (atroximasaponin G1, 5), and its cis-isomer, atroximasaponin G2 (6), respectively.     

Saponarioside C, the first alpha-D-galactose containing triterpenoid saponin, and five related compounds from Saponaria officinalis

Six novel triterpenoid saponins, named saponariosides C-H, were isolated from the whole plants of Saponaria officinalis. Their structures were established as saponarioside C (1), 3-O-beta-D-xylopyranosyl-gypsogenic acid-28-O-alpha-D-galactopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-- >6)-[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranoside; saponarioside D (2), 3-O-beta-D-xylopyranosyl-gypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->6) -[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranoside; saponarioside E (3), 3-O-beta-D-glucopyranosyl-gypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->6) -[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranoside; saponarioside F (4), 3-O-beta-D-xylopyranosyl-16alpha-hydroxygypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->6) -[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranoside; saponarioside G (5), 3-O-beta-D-xylopyranosyl-16alpha-hydroxygypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->6)-[beta-D-glucopyranosyl-(1-->3 )]-beta-D-glucopyranoside; and saponarioside H (6), 3-O-beta-D-xylopyranosyl-gypsogenic acid-28-O-beta-D-glucopyranoside, by a combination of extensive NMR (DEPT, COSY, HOHAHA, HETCOR, HMBC, and NOESY) studies and chemical degradation.     

New lignan glycosides with potent antiinflammatory effect, isolated from Justicia ciliata

Two new lignan glycosides, 4-O-[alpha-L-arabinopyranosyl-(1' "-->2' ')-beta-D-xylopyranosyl-(1' " '-->5' ')-beta-D-apiofuranosyl]diphyllin (1), named ciliatoside A (1), and 4-O-?[beta-D-apiofuranosyl-(1' " "-->3' ")-alpha-L-arabinopyranosyl-(1' "-->2' ')][beta-D-xylopyranosyl-(1' " '-->5' ')]-beta-D-apiofuranosyl?diphyllin (2), named ciliatoside B (2), were isolated from the whole plant of Justicia ciliata. The structures of 1 and 2 were determined by spectral and chemical methods. Compounds 1 and 2 strongly inhibited the accumulation of NO(2)(-) in lipopolysaccharide-stimulated RAW 264.7 cells in a concentration-dependent manner with IC(50) values of 27.1 +/- 1.6 and 29.4 +/- 1.4 microM, respectively.     

Phenylethanoid glycosides from Globularia trichosantha.

Five phenylethanoid glycosides, crenatoside (= oraposide) (1), verbascoside (= acteoside) (2), trichosanthoside A (3), rossicaside A (4), and trichosanthoside B (5), were isolated from the aerial parts of Globularia trichosantha. Compounds 3 and 5 are new natural compounds, and their structures were established as 3, 4-dihydroxy-beta-phenylethoxy-O-beta-D-xylopyranosyl-(1-->4)-alpha -L- rhamnopyranosyl-(1-->3)-4-O-caffeoyl-beta-D-glucopyranoside and 3, 4-dihydroxy-beta-phenylethoxy-O-[beta-D-xylopyranosyl-(1-->4)-alph a-L -rhamnopyranosyl-(1-->3)]-[beta-D-xylopyranosyl-(1-->6)]-4-O-caffeoyl -beta-D-glucopyranoside, respectively. The structures of all compounds were established by spectral evidence. Compounds 1-5 also demonstrated scavenging properties toward the 2, 2-diphenyl-1-picrylhydrazyl radical in TLC autographic assays.     

Steroidal saponins from the rhizomes of Polygonatum sibiricum

Four new steroidal saponins, named neosibiricosides A-D (1-4), were isolated from the rhizomes of Polygonatum sibiricum, along with two known spirostanol glycosides. The structures of the new glycosides were elucidated by spectroscopic methods and acid hydrolysis as (23S,24R,25R)-1-O-acetylspirost-5-ene-1beta,3beta,23,24-tetrol 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->4)-beta-D-fucopyranoside (1), (25S)-1-O-acetylspirost-5-ene-1beta,3beta-diol 3-O-beta-D-glucopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside (2), (25S)-spirost-5-en-3beta-ol 3-O-beta-D-glucopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucopyranosyl-(1-->4)-2-O-acetyl-beta-D-galactopyranoside (3), and (25R,S)-spirost-5-en-3beta-ol 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside (4). The cytotoxic activity of the isolated compounds was evaluated with human MCF-7 breast cancer cells.     

Cytotoxic furostanol saponins and a megastigmane glucoside from tribulus parvispinus

Two new furostanol saponins, (25R)-26-O-beta-D-glucopyranosyl-5alpha-furostan-2alpha,3beta,22alpha,26-tetraol 3-O-{beta-D-galactopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside} (1) and (25R)-26-O-beta-D-glucopyranosyl-5alpha-furostan-3beta,22alpha,26-triol 3-O-{beta-D-galactopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside} (2), and their O-methyl derivatives (3 and 4), and a new megastigmane glucoside, (6S,7E,9xi)-6,9,10-trihydroxy-4,7-megastigmadien-3-one 10-O-beta-D-glucopyranoside (6), along with one known spirostanol saponin, gitonin (5), and four known megastigmane glucosides were isolated from the aerial parts of Tribulus parvispinus. Their structures were established by detailed spectroscopic analysis. The cytotoxic activities of 1-6 against U937, MCF7, and HepG2 cells were evaluated. Compounds 2 (IC(50) 0.5 microM) and 5 (IC(50) 0.1 microM) showed the highest activity against U937 cells.     

黄花倒水莲降血脂活性成分研究

从黄花倒水莲Polygala fallaxHem sl.根的降血脂有效部位中分离得到四个皂苷类化合物,分别鉴定为3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl presenegen in 28-O-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)--βD-fucopyransoyl ester(Ⅰ)、3-O--βD-glucopyranosyl-(1→2)--βD-glucopyranosyl presenegen in 28-O-β-D-xy-lopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-(3-O-acetyl)-β-D-fucopyranosyl ester(Ⅱ)、3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl presenegen in 28-O-β-D-xylopyranosyl-(1→4)--αL-rhamnopyranosyl-(1→2)-(4-O-acetyl)-β-D-fucopyranosyl ester(Ⅲ)和3-O-β-D-glucopyranosyl-(1→2)--βD-glucopyranosyl presenegen in 28-O-β-D-xylopyrano-syl-(1→4)-α-L-rhamnopyranosyl-(1→2)-(3,4-d iacetyl)--βD-fucopyranosyl ester(Ⅳ)。     

New triterpenoid saponins from Maesa japonica

New triterpenoid saponins, maejaposides A, B, C, D, and E, were isolated from the roots of Maesa japonica and were, respectively, defined to be 3-O-[beta-D-xylopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->2)-bet a-D-galactopyranosyl-(1-->3)] [beta-D-galactopyranosyl-(1-->2)]beta-D-glucuronopyranosides of 22alpha-[(Z)-2-hexenoyloxy]-13beta,28-oxido-olean++ +-16alpha, 28alpha-diol (1); 22alpha-[2'-methylbutanoyl]-13beta, 28-oxido-olean-16alpha,28alpha-diol (2a) and 22alpha-angeloyloxy-13beta,28-oxido-olean-16a lpha,28alpha-diol (2b); 21beta,22alpha-diangeloyloxy-13beta,28-oxido- olean-16alpha, 28alpha-diol (3); 21beta-angeloyloxy, 22alpha-(2'-methylbutanoyl)-13beta,28-oxido-olean++ +-16alpha, 28alpha-diol (4), and 21beta-angeloyloxy, 22alpha-[(Z)-2'-hexenoyl]-13beta,28-oxido-olean- 16alpha,28alpha-diol (5). Their structures were established on the basis of extensive NMR (DEPT, COSY, HOHAHA, HETCOR, HMBC, and NOESY) and ESIMS/MS studies, along with chemical degradation.     

合欢皂甙J6的结构鉴定

目的 :从合欢皮中分离皂甙。方法 :用色谱法分离 ,波谱法鉴定其结构。结果和结论 :从合欢皮的 95%乙醇提取物中分得 1个三糖链八糖皂甙 ,结构为 3-O [β-D 吡喃木糖基 ( 1→ 2 )-α-L 吡喃阿拉伯糖基 ( 1→ 6)-β-D 2 去氧 2 乙酰胺基 吡喃葡萄糖基 ] 21O {6S2 反式2羟甲基6甲基6-o[4-O ( 6S-2 反式-2 羟甲基 6-甲基 6-羟基 2 ,7 辛二烯酰基 ) β D 吡喃鸡纳糖基 ] 2 ,7 辛二烯酰基 } 金合欢酸-28-O-β-D 吡喃葡萄糖基 (1→ 3)[α- L 呋喃阿拉伯糖基 (1→ 4) ] α L 吡喃鼠李糖基 (1→ 2)-β-D 吡喃葡萄糖酯 ,为新化合物 ,命名为合欢皂甙J6 。     

Saponins from the roots of Nylandtia spinosa

From the roots of Nylandtia spinosa, four new triterpene saponins, 3- O-beta- d-glucopyranosylpresenegenin 28- O-beta- d-galactopyranosyl-(1-->4)-[alpha- l-arabinopyranosyl-(1-->3)]-beta- d-xylopyranosyl-(1-->4)-[beta- d-apiofuranosyl-(1-->3)]-alpha- l-rhamnopyranosyl-(1-->2)-beta- d-fucopyranosyl ester ( 1), 3- O-beta- d-glucopyranosylpresenegenin 28- O-beta- d-galactopyranosyl-(1-->4)-[alpha- l-arabinopyranosyl-(1-->3)]-beta- d-xylopyranosyl-(1-->4)-alpha- l-rhamnopyranosyl-(1-->2)-beta- d-fucopyranosyl ester ( 2), 3- O-beta- d-glucopyranosylpresenegenin 28- O-beta- d-apiofuranosyl-(1-->4)-[beta- d-galactopyranosyl-(1-->2)]-beta- d-xylopyranosyl-(1-->4)-alpha- l-rhamnopyranosyl-(1-->2)-beta- d-fucopyranosyl ester ( 3), and 3- O-beta- d-glucopyranosylpresenegenin 28- O-beta- d-apiofuranosyl-(1-->3)-beta- d-xylopyranosyl-(1-->4)-alpha- l-rhamnopyranosyl-(1-->2)-beta- d-fucopyranosyl ester ( 4), were isolated, together with the known tenuifolin. Their structures were established mainly by 2D NMR techniques and mass spectrometry. Compounds 1- 4 were evaluated for cytotoxicity against HCT 116 and HT-29 human colon cancer cells, but were inactive (IC50 > 5 microg/mL).     

Cytotoxic steroidal saponins from the rhizomes of Asparagus oligoclonos

Two new steroidal saponins, aspaoligonins A (2) and B (3), were isolated from the methanolic extract of the rhizomes of Asparagus oligoclonos together with a known spirostanol saponin, asparanin A (1). Aspaoligonins A and B were characterized as (25S*)-5beta-spirostan-3beta,17alpha-diol 3-O-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranoside and (25S*)-5beta-spirostan-3beta,17alpha-diol 3-O-alpha-L-rhamnopyanosyl (1-->4)-[beta-D-xylopyranosyl-(1-->2)]-beta-D-glucopyranoside, respectively, by spectrometric analyses including HRFABMS and 2D NMR. Compounds 1-3 were cytotoxic against five human tumor cell lines with IC50 values of 2.05-2.84 microg/mL.     

Silenosides A-C, triterpenoid saponins from Silene vulgaris.

Three new triterpenoid saponins named silenosides A-C (1-3) were obtained from the roots of Silene vulgaris. Their structures were elucidated by spectral and chemical methods as beta-D-galactopyranosyl(1-->2)-beta-D-glucuronopyranosyl-3beta- hydrox y-23-oxoolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl(1-->3)-beta-D-xylopyranosyl(1-->4)-alpha-L- rhamnopyranosyl(1-->2)-beta-D-fucopyranoside; 3-O-beta-D-galactopyranosyl(1-->2)-beta-D-glucuronopyranosyl-3beta , 16alpha-dihydroxy-23-oxoolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl(1-->4)-[beta-D-glucopyranosyl(1-->2)]-alpha -L-rhamnopyranosyl(1-->2)-beta-D-fucopyranoside; and 3-O-alpha-L-arabinopyranosyl(1-->3)-[beta-D-galactopyranosyl(1-->2 )]- beta-D-glucuronopyranosyl-3beta, 16alpha-dihydroxy-23-oxoolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl(1-->4)-[beta-D-glucopyranosyl(1-->2)]-alpha -L-rhamnopyranosyl(1-->2)-beta-D-fucopyranoside, respectively.