Two diastereomeric saponins with cytotoxic activity from Albizia julibrissin Original Research Article

Two diastereomeric saponins, julibrosides J1 (1) and J9 (2), both of which show cytotoxic activity, were obtained from the stem bark of Albizia julibrissin Durazz. On the basis of chemical and spectral evidence [L.B. Ma et al., Carbohydr. Res., 281 (1996) 35–46], the structure of 1 was revised as 3-O-[β-d-xylopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranosyl]-21-O-{(6S)-2-trans-2-hydroxymethyl-6-methyl-6-O-[4-O-((6R)-2-trans-2,6-dimethyl-6-O-(β-d-quinovopyranosyl)-2,7-octadienoyl)-β-d-quinovopyranosyl]-2,7-octadienoyl}acacic acid-28-O-β-d-glucopyranosyl-(1→3)-[α-l-arabinofuranosyl-(1→4)]-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl ester. The diastereoisomer 2 of 1 was identified as 3-O-[β-d-xylopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranosyl]-21-O-{(6S)-2-trans-2-hydroxymethyl-6-methyl-6-O-[4-O-((6S)-2-trans-2,6-dimethyl-6-O-(β-d-quinovopyranosyl)-2,7-octadienoyl)-β-d-quinovopyranosyl]-2,7-octadienoyl}acacic acid-28-O-β-d-glucopyranosyl-(1→3)-[α-l-arabinofuranosyl-(1→4)]-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl ester. Saponin 2 is a new saponin named julibroside J9. Both julibrosides J1 and J9 show good inhibitory action against the KB cancer cell line in vitro.