Structure elucidation of two acylated triterpenoid bisglycosides from Acacia auriculiformis Cunn.

Article abstract of DOI:10.1016/S0040-4020(01)80017-X

Acaciasides A and B, two novel acylated triterpenoid bisglycosides isolated from the fruits of Acacia auriculiformis, were respectively defined to be 3-O-[β-D-glucopyranosyl (1 → 6) {α-L-arabinopyranosyl (1 → 2)}-β-D-glucopyranosyl]-21-O-{6' S)-2'-trans-2',6'-dimethyl-6'-O-β-D-glucopyranosyl-2',7'- octadienoyl} acacic acid 28-O-α-L-rhamnopyranosyl (1 → 6) [β-D-xylopyranosyl (1 → 2)]-β-D-glucopyranoside (1) and 3-O-[β-D-glucopyranosyl (1 → 6) {α-L-arabinopyranosyl (1 → 2)}-β-D-glucopyranosyl]-21-O-[(6' S)-2'-trans-2',6'-dimethyl-6'-O-{β-D-xylopyranosyl (1 → 2)-β-D-glucopyranosyl}-2',7'-octadienoyl] acetic acid 28-O-α-L-rhamnopyranosyl (1 → 6) [β-D-xylopyranosyl (1 → 2)]-β-D-glucopyranoside (2). The structural details were elucidated by a combination of fast-atom-bombardment mass spectrometry, ¹H-, and ¹³C NMR spectroscopy, and some chemical transformations.