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Three new ( 1–3 ) and two known ( 4–5 ) triterpene glycosides were isolated from the leaves of Acanthopanax japonicus (Araliaceae) and elucidated structurally by mass, 1D, and 2D NMR spectroscopy. All the compounds possessed a nor -oleanene triterpene skeleton as the aglycone. The structures of 1–5 were established as 28- O -α- l - rhamno-pyranosyl-(1→4)-β- d -glucopyranosyl-(1→6)-β- d -glucopyranosyl ester of 3β-hydroxy- 30- nor -olean-12,20(29)-diene-23,28-dioic acid, designated as acanjaposide A, 3β- hydroxy-23-oxo-30- nor -olean-12,20(29)-diene-28-oic acid, named acanjaposide B, 3β,20α-dihydroxy-23-oxo-30- nor -olean-12-en-28-oic acid, named acanjaposide C, and nipponoside E, a known saponin, respectively.

The metabolic pathway of chiisanoside isolated from leaves of Acanthopanax divaricatus var. albeofructus (Araliaceae) by human intestinal bacteria and by the protein fraction of leaves of this plant were investigated, and the cytotoxic and anti-rotaviral activities of chiisanoside and its metabolite, chiisanogenin, were assayed. Chiisanogenin was produced as a main metabolite, when chiisanoside were incubated for 15 h with human intestinal bacteria. This metabolic pathway proceeded more potently with the protein fraction than with human intestinal bacteria. The in vitro cytotoxicity of chiisanogenin was superior to that of chiisanoside. H+/K+ ATPase was more potently inhibited by chiisanogenin than by chiisanoside. However, the anti-rotaviral activity of chiisanoside was more potent than that of chiisanogenin.

Four new 3,4-seco-lupane-type triterpene glycosides (1-4) were isolated from the leaves of Acanthopanax senticosus forma inermis. The structures of 1-4 were established as 11alpha-hydroxy-3, 4-seco-lup-4(23),20(30)-dien-3-oic acid methyl ester 28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1--4)-beta-D-glucopyranosyl-(1--6)-be ta-D-glucopyranoside, designated as inermoside (1); 1-deoxychiisanoside (2); 24-hydroxychiisanoside (3); and 11-deoxyisochiisanoside (4) by (1)H-(1)H COSY and (1)H-(13)C COSY(HMBC, HMQC) methods and FABMS.

Two new lupane-triterpene glycosides named acankoreosides C and D, were isolated from the leaves of Acanthopanax koreanum. Based on spectroscopic data, the chemical structures were determined as 3-O-β- d -glucopyranosyl 3α,11α-dihydroxylup-20(29)-en-28-oic acid 28-O-α- l -rhamnopyranosyl-(1→4)-β- d -glucopyranosyl-(1→6)-β- d -glucopyranosyl ester and 3α,11α-dihydroxylup-23-al-20(29)-en-28-oic acid 28-O-α- l -rhamnopyranosyl-(1→4)-β- d -glucopyranosyl-(1→6)-β- d -glucopyranosyl ester, respectively.

A new lupane triterpene glycoside, acantrifoside A, was isolated from the leaves of Acanthopanax trifoliatus and A. koreanum . Based on spectroscopic data, the compound was identified as 3α,11α-dihydroxylup-20(29)-en-28-oic acid 28- O -α- l -rhamnopyranosyl-(1→4)-β- d -glucopyranosyl-(1→6)-β- d -glucopyranosyl ester.

Two new lupane-triterpene glycosides, acankoreoside A (I) and B (2), were isolated from the leaves of Acanthopanax koreanum NAKAI (Araliaceae). Based on spectroscopic data, the chemical structures of 1 and 2 were determined as 3α-hydroxy-lup-20(29)-en-23,28-dioic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester and 3α,11α,23-trihydroxy-lup-20(29)-en-28-oic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, respectively.

Two 3,4-seco-lupane triterpenoids (1, 2) were isolated from the leaves of Acanthopanax divaricatus var. albeofructus (Araliaceae). Based on the spectroscopic data, the chemical structures of 1 and 2 were characterized as 24-hydroxychiisanogenin and 22alpha-hydroxychiisanogenin, respectively. 1 was a new compound and 2 was isolated for the first time from the natural source, although it had been obtained as an enzymatically hydrolyzed artifact from 22alpha-hydroxychiisanoside.

Two new lupane-triterpene glycosides, acankoreoside A (I) and B (2), were isolated from the leaves of Acanthopanax koreanum NAKAI (Araliaceae). Based on spectroscopic data, the chemical structures of 1 and 2 were determined as 3α-hydroxy-lup-20(29)-en-23,28-dioic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester and 3α,11α,23-trihydroxy-lup-20(29)-en-28-oic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, respectively.

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.

Two 3,4-seco-lupane triterpenoids (1, 2) were isolated from the leaves of Acanthopanax divaricatus var. albeofructus (Araliaceae). Based on the spectroscopic data, the chemical structures of 1 and 2 were characterized as 24-hydroxychiisanogenin and 22alpha-hydroxychiisanogenin, respectively. 1 was a new compound and 2 was isolated for the first time from the natural source, although it had been obtained as an enzymatically hydrolyzed artifact from 22alpha-hydroxychiisanoside.