Four new oleanane saponins from Anemone anhuiensis

Four new oleanane triterpene saponins, anhuienosides C-F, together with three known saponins, were isolated from the rhizomes of Anemone anhuiensis (Ranunculaceae). The structures of anhuienosides C-F were elucidated as 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3-O-beta-D-xylopyranosyl oleanolic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl oleanolic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3-O-beta-D-glucopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyl oleanolic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, respectively.     

Four new triterpene glycosides from Nigella damascena

Four new triterpene glycosides, named nigellosides A, B, C, and D, were from the air-dried aerial parts of Nigella damascena L. (Ranunculaceae), and the structures were elucidated on the basis of spectroscopic data including 2D NMR spectra and chemical evidence. Their chemical structures have been characterized as 3-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl gypsogenin 28-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3-O-beta-D-glucopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl gypsogenin 28-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyl hederagenin 28-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, and 3-O-beta-D-glucopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyl hederagenin 28-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester.     

Acetylated triterpene saponins from the Thai medicinal plant, Sapindus emarginatus

From the pericarps of Sapindus emarginatus (Sapindaceae), three new acetylated triterpene saponins were isolated together with hederagenin and five known triterpene saponins, as well as one known sweet acyclic sesquiterpene glycoside, mukurozioside IIb. The structures of new compounds were elucidated as hederagenin 3-O-(2-O-acetyl-beta-D-xylopyranosyl)-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside, 23-O-acetyl-hederagenin 3-O-(4-O-acetyl-beta-D-xylopyranosyl)-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside and oleanolic acid 3-O-(4-O-acetyl-beta-D-xylopyranosyl)-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside by chemical and spectroscopic data.     

A new triterpenoid saponin from Gleditisia sinensis and structure-activity relationships of inhibitory effects on lipopolysaccharide-induced nitric oxide production

A phytochemical investigation of the anomalous fruits of Gleditisia sinensis led to one new oleanane-type triterpenoid saponin acylated with one monoterpenic acid, 3-O-beta-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, named gleditsioside Z (1), together with nine known ones (2-10). Their structural details were mainly established on the basis of 1D, 2D NMR and HR-MS analysis as well as some chemical methods. Structure-activity relationships of the isolated saponins that affected nitric oxide production from cultured mouse macrophages (RAW 264.7 cell lines) induced by lipopolysaccharide were discussed.     

Five new triterpenoid saponins from the roots of Platycodon grandiflorum

Five new triterpenoid saponins, platycoside H [3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], platycoside I [3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], platycoside J [3-O-beta-D-glucopyranosyl-2beta,3beta,16alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], platycoside K [3-O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23,24-pentahydroxyolean-12-en-28-oic acid], and platycoside L [3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23,24-pentahydroxyolean-12-en-28 oic acid], and three known triterpenoid saponins, platycoside F, platycoside B, and platycoside C, were isolated from the roots of Platycodon grandiflorum A. DC. Their chemical structures were elucidated on the basis of their spectral data and chemical evidence.     

Pancreatic lipase-inhibiting triterpenoid saponins from Gypsophila oldhamiana

Three new triterpenoid saponins, gypsosaponins A-C (1-3), were isolated from the roots of Gypsophila oldhamiana (Caryophyllaceae). Their structures were established as 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosyl quillaic acid 28-O-alpha-L-arabinopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (1), 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-methyl-beta-D-glucuronopyranosyl gypsogenin 28-O-beta-D-glucopyranosyl-(1-->3)-[beta-D-xylopyranosyl-(1-->4)]-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (2), and 23-O-beta-D-glucopyranosyl gypsogenic acid 28-O-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranoside (3), on the basis of various spectroscopic analyses and chemical degradations. The biological activities of 1-3 were examined inhibitory activity against pancreatic lipase, which showed inhibition of 58.2%, 99.2% and 50.3% at concentration of 1 mg/ml, respectively.     

Five new phenylethanoid glycosides from the whole plants of Lamium purpureum L

Five new phenylethanoid glycosides, lamiusides A (1), B (2), C (3), D (4) and E (5), were isolated from the whole plants of Lamium purpureum L. (Labiatae) together with seven known compounds (6-12). On the basis of chemical and spectral analyses, the structures of the new compounds were elucidated to be 2-(3,4-dihydroxyphenyl)ethyl-O-beta-D-galactopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->3)-(4-O-trans-caffeoyl)-beta-D-glucopyranoside (1), 2-(3,4-dihydroxyphenyl)ethyl-O-beta-D-galactopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->3)-(4-O-trans-feruloyl)-beta-D-glucopyranoside (2), 2-(3,4-dihydroxyphenyl)ethyl-O-beta-D-galactopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->3)-(6-O-trans-caffeoyl)-beta-D-glucopyranoside (3), 2-(3,4-dihydroxyphenyl)-R,S-methoxy-ethyl-O-beta-D-galactopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->3)-(4-O-trans-caffeoyl)-beta-D-glucopyranoside (4) and 2-(3-hydroxy-4-methoxyphenyl)ethyl-O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->6)-(4-O-cis-feruloyl)-beta-D-glucopyranoside (5). In addition, the radical-scavenging activities of compounds 1-4 on 1,1-diphenyl-2-picrylhydrazyl radical were examined.     

Five new bidesmoside triterpenoid saponins from Stauntonia chinensis

Eleven triterpenoid saponins (1-11) were isolated from Stauntonia chinensis DC. (Lardizabalaceae), including five new compounds, yemuoside YM(21-25) (1-3, 6, 7) structures of which were elucidated by chemical methods and a combination of MS, 1D- and 2D- NMR experiments including DEPT, (1)H--(1)H COSY, HSQC, HMBC, TOCSY, and NOESY as 3-O-alpha-L-arabinopyranosyl-(1 --> 3)-[alpha-L-rhamnopyranosyl-(1 --> 2)-]alpha-L-arabinopyranosyl-akebonicacid-28-O-alpha-L-rhamnopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (1), 3-O-beta-D-xylopyranosyl-(1 --> 3)-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl-akebonic acid-28-O-alpha-L-rhamnopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (2), 3-O-beta-D-glucopyranosyl-(1 --> 3)-alpha-L-arabinopyranosyl-akebonic acid-28-O-alpha-L-rhamnopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (3), 3-O-alpha-L-arabinopyranosyl-(1 --> 3)-[alpha-L-rhamnopyranosyl-(1 --> 2)-]alpha-L-arabinopyranosyl-akebonic acid-28-O-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (6), 3-O-alpha-L-arabinopyranosyl-(1 --> 3)-[alpha-L-arabinopyranosyl-(1 --> 2)-]alpha-L-arabinopyranosyl-akebonic acid-28-O-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (7).     

Four new cycloartane glycosides from Thalictrum fortunei

Four new cycloartane glycosides were isolated from the aerial parts of Thalictrum fortunei (Ranunculaceae). The chemical structures of these new glycosides were elucidated as 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-fucopyranosyl (22S,24Z)-cycloart-24-en-3beta,22,26-triol 26-O-beta-D-glucopyranoside, 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-fucopyranosyl (22S,24Z)-cycloart-24-en-3beta,22,26-triol 26-O-beta-D-quinovopyranosyl-(1-->6)-beta-D-glucopyranoside, 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-fucopyranosyl (22S,24Z)-cycloart-24-en-3beta,22,26-triol 26-O-beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside, and 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-fucopyranosyl (22S,24Z)-cycloart-24-en-3beta,22,26-triol 26-O-alpha-L-arabinopyranosyl-(1-->6)-beta-D-glucopyranoside by extensive NMR methods, HR-ESI-MS, and hydrolysis. This is the first report of (22S,24Z)-3beta,22,26-trihydroxycycloartan-24-ene (thelictogenin A, 5) being glycosylated at C-26.     

Cholestane glycosides from Solanum abutiloides. III

Four new cholestane glycosides, named abutilosides D (1), E (2), F (3) and G (4), were isolated from the fresh roots of Solanum abutiloides. By chemical and spectroscopic evidence, their structures were elucidated as 26-O-beta-D-glucopyranosyl 3beta,16alpha,26-trihydroxy-5alpha-cholestan-22-one 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->4)-beta-D- glucopyranoside and its desxylosyl compound (1 and 3, respectively), 26-O-beta-D-glucopyranosyl 3beta,16alpha,26-trihydroxycholest-5-en-22-one 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->4)-beta-D- glucopyranoside and its desxylosyl compound (2 and 4, respectively). These compounds were regarded as precursors of a dormantinone type compound on a hypothetical pathway of steroid biogenesis.     

New A-ring lactone triterpenoid saponins from the roots of Platycodon grandiflorum

Three new A-ring lactone triterpenoid saponins, platycoside M-1 [3-O-beta-D-glucopyranosyl platycogenic acid A lactone], platycoside M-2 [3-O-beta-D-glucopyranosyl platycogenic acid A lactone 28-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], and platycoside M-3 [3-O-beta-D-glucopyranosyl platycogenic acid A lactone 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], were isolated from the roots of Platycodon grandiflorum A. DC. Their chemical structures were elucidated on the basis of their spectral data and chemical evidence.     

Secondary metabolites from Phlomis oppositiflora

In addition to rare phenylethanoid triglycosides, myricoside and its dimetylether derivative serratumoside A {3-hydroxy,4-methoxy-beta-phenylethoxy-O-beta-D-apiofuranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->3)-4-O-feruloyl-beta-D-glucopyranoside}, a new phenylethanoid glycoside, myricoside-3"-O-methylether {3,4-dihydroxy-beta-phenylethoxy-O-beta-D-apiofuranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->3)-4-O-feruloyl-beta-D-glucopyranoside} along with a new neolignan glucoside, (7S, 8R)-dehydroconiferyl alcohol-8-5'-dehydroconiferyl aldehyde 4-O-beta-D-glucopyranoside were isolated from the aerial parts of Phlomis oppositiflora. The structures of the new compounds were identified by means of spectroscopic (UV, IR, 1D- and 2D-NMR, and LC-ESIMS) methods.     

Bioactive saponins and glycosides. XVI. Nortriterpene oligoglycosides with gastroprotective activity from the fresh leaves of Euptelea polyandra Sieb. et Zucc. (1): structures of Eupteleasaponins I, II, III, IV, V, and V acetate

The saponin fraction from the fresh leaves of Euiptelea polyandra Sieb. et Zucc. was found to exhibit potent gastroprotective activity. Fourteen new nortriterpene saponins called eupteleasaponins were isolated from the saponin fraction with gastroprotective activity. The structures of eupteleasaponins I, I1, III, IV, V, and V acetate were determined on the basis of chemical and physicochemical evidence as 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl(1 -->3)-beta-D-xylopyranosylakebonoic acid 28-O-beta-D-glucopyranosyl ester, 3-O-alpha-L-rhamnopyranosyl(1-->2)-[alpha-L-rhamnopyranosyl(1 -->4)-beta-D-glucopyranosyl(1-->3)-beta-D-xylopyranosylakebonoic acid 28-O-beta-D- D-glucopyranosyl(1-->3)-beta-D-xylopyranosylakebonoic acid 28-O-beta-D-glucopyranosyl ester, 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-rhamnopyranosyl(1 -->4)-beta-D-glucopyranosyl(1-->3)-beta-D-xylopyranosylakebonoic acid 28-O-beta-D-glucopyranosyl ester, 3-O-alpha-L-rhamnopyranosyl(1 -->2)-[alpha-L-arabinopyranosyl(1-->4)-alpha-L-rhamnopyranosyl(1-- >4)]-beta-D- glucopyranosyl(1-->3)-beta-D-xylopyranosylakebonoic acid 28-O-beta-D-glucopyranosyl ester, 3-O-alpha-L-rhamnopyranosvl(1-->2)-[alpha-L-arabinopyranosyl (1 -->4)-beta-L-rhamnopyranosyl(1 -->4)]-beta-D-glucopyranosyl(1 -->3)-beta-D-xylopyranosylakebonoic acid, 3-O-alpha-L-rhamnopyranosyl(1 -->2)-beta-D-glucopyranosvl(1-->3)-beta-D-xylopyranosyleupteleo genin, and 3-O-alpha-L-rhamnopyranosyl(1-->2)-6"-O-acetyl-gamma-D-glucopyranosyl(1 -->3)-beta-D-xylopyranosyleupteleogenin.     

Two new triterpenoid saponins isolated from Polygala japonica

Bioassay guided investigation of whole parts of Polygala japonica afforded two new triterpenoid saponins, characterized as 3-O-beta-D-glucopyranosyl medicagenic acid 28-O-{beta-D-xylopyranosyl(1-->4)-[beta-D-apiofuranosyl(1-->3)]-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl} ester (1), 3-O-beta-D-glucopyranosyl 2-oxo-olean-12-en-23, 28-dioic acid 28-O-{beta-D-xylopyranosyl(1-->4)-[beta-D-apiofuranosyl(1-->3)]-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl} ester (2), together with four known triterpenoid saponins (3-6). Their structures were elucidated by spectroscopic and chemical methods. Saponins 3, 4 and 5 showed significant anti-inflammation effects on carrageenan-induced acute paw edema in mouse.     

Studies on the constituents of Luffa acutangula Roxb. I. Structures of acutosides A--G, oleanane-type triterpene saponins isolated from the herb.

From the herb of Luffa acutangula ROXB. (Cucurbitaceae), seven oleanane-type triterpene saponins, acutosides A--G, were isolated and their structures were determined. Acutoside A is oleanolic acid 3-O-beta-D-glucopyranosyl-(1----2)-beta-D-glucopyranoside. Acutosides B, D, E, F and G have a common prosapogenin structure, acutoside A, and only differ in the structures of the ester-linked sugar moieties. Acutoside B is a 28-O-[O-beta-D-xylopyranosyl-(1----4)-O-alpha-L-rhamnopyranosyl-(1----2) -alpha-L-arabinopyranosyl] ester, D is a 28-O-[O-beta-D-xylopyranosyl-(1----3)-O-beta-D-xylopyranosyl-(1----4)-O- alpha-L-rhamnopyranosyl-(1----2)-alpha-L-arabinopyranosyl] ester, E is a 28-O-[O-alpha-L-arabinopyranosyl-(1----3)-O-beta-D-xylopyranosyl-( 1----4)-O-alpha-L-rhamnopyranosyl-(1----2)-alpha-L-arabinopyranosyl] ester, F is a 28-O-[O-beta-D-xylopyranosyl-(1----3)-[O-beta-D-xylopyranosyl-(1----4)-O -alpha-L-rhamnopyranosyl-(1----2)-alpha-L-arabinopyranosyl] ester, and G is a 28-O-beta-D-xylopyranosyl-(1----3)-[O-alpha-L-arabinopyranosyl-(1- ---3)-O-beta-D-xylopyranosyl-(1----4)]-O-alpha-L- rhamnopyranosyl-(1----2)-alpha-L-arabinopyranosyl] ester. Acutoside C is a machaelinic acid (=21 beta-hydroxyoleanolic acid) saponin having the same sugar moiety as that of acutoside B.     

New triterpenoid saponins from Maesa tenera.

Two new triterpenoid saponins, maetenosides A and B were isolated from the aerial parts of Maesa tenera and were respectively defined as 3-O-[beta-D-glucopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->3)][beta-D-glucopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl camelliagenin A 22-O-angelate (1) and 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->3)][beta-o-glucopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl camelliagenin A 22-O-angelate (2). Their structures were established on the basis of chemical and spectroscopic methods.     

A new flavonol glycoside from the aerial parts of Astragalus vulneraria

A new flavonol glycoside, isorhamnetin 3-O-beta-D-apiofuranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-galactopyranoside, and the known diglycoside, isorhamnetin 3-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-galactopyranoside were isolated from the aerial parts of Astragalus vulneraria. Characterization of the two compounds was done by spectroscopic methods (1D and 2D NMR, and FAB-MS).     

A new steroidal saponin from Dioscorea cayenensis

The new 26-O-beta-D-glucopyranosyl-3beta,26-dihydroxy-20,22-seco-25(R)-furost-5-en-20,22-dione-3-O-alpha-L-rhamnopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranoside (1), along with the known methyl protodioscin (2), asperoside (3) and prosapogenin A of dioscin (4) were isolated from the rhizomes of Dioscorea cayenensis LAM.-HOLL (Dioscoreaceae). Their structures were established mainly on the basis of 600 MHz 2D-NMR spectral data. 4 exhibited antifungal activity against the human pathogenic yeasts Candida albicans, C. glabrata and C. tropicalis (MICs of 20.8, 6.25, 25 microg/ml, respectively), whereas saponins 1-3 were inactive.     

Lupane-triterpene glycosides from the leaves of Acanthopanax gracilistylus

A novel lupane-triterpene glycoside, called wujiapioside B (1), was isolated from the leaves of Acanthopanax gracilistylus (Araliaceae) together with three known lupane-triterpene glycosides, acankoreoside C (2), acantrifoside A (3) and 3-epibetulinic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (4). Based on spectroscopic data, the chemical structure of 1 was determined as 3alpha,23-dihydroxy-lup-20(29)-en-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester. Compounds 2-3 were obtained for the first time from this plant and compound 4 has not been isolated from Acanthopanax genus yet.     

Triterpene glycosides from the stems of Akebia quinata

The stems of Akebia quinata have been analyzed for their triterpene glycoside constituents, resulting in the isolation of six new triterpene glycosides, along with 19 known ones. On the basis of extensive spectroscopic analysis, including 2D NMR data, and chemical evidence, the structures of the new compounds were deter-mined to be 3beta-[(O-beta-D-glucuronopyranosyl-(1-->3)-alpha-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3beta-[(O-beta-D-glucuronopyranosyl-(1-->3)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3beta-[(O-beta-D-glucuronopyranosyl-(1-->3)-alpha-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3beta-[(O-beta-D-glucuronopyranosyl-(1-->3)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]-29-hydroxyolean-12-en-28-oic acid, and 3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]-23,29-dihydroxyolean-12-en-28-oic acid, respectively. The main triterpene glycosides contained in the stems of A. quinata were found to have two sugar units at C-3 and C-28 of the aglycone in this study, whereas those of Akebia trifoliate were reported to possess one sugar unit at C-28 of the aglycone. It may be possible to distinguish between A. quinata and A. trifoliate chemically by comparing their triterpene glycoside constituents.