A New Cleavage Method for the Sugar – Aglycone Linkage in Saponin

✍ Scribed by Higuchi, Ryuichi ;Tokimitsu, Yoshinori ;Hamada, Naoko ;Komori, Tetsuya ;Kawasaki, Toshio

• Publisher: John Wiley and Sons
• Year: 1985
• Tongue: English
• Weight: 531 KB
• Volume: 1985
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.198519850609

✦ Synopsis

Abstract

A new cleavage method for the sugar – aglycone linkage in saponin is described. Treatment of [28‐hydroxy‐23,28‐dioxoolean‐12‐en‐3β‐yl‐O‐β‐D‐galactopoyranosyl‐(1 → 2)‐O‐α‐L‐arabinopyranosyl‐(1 → 3)‐β‐D‐glucopyranosid]uronic acid (1) with diazomethane – ether in methanol gave the aglycone 2 and the sugars 3 and 4. On the basis of chemical and spectral evidence they were determined as methyl 3β,23α‐dihydroxy‐3‐O,23‐methylenolean‐12‐en‐28‐oate (2), methyl [methyl O‐β‐D‐galactopyranosyl‐(1 → 2)‐O‐α‐L‐arabinopyranosyl‐(1 → 3)‐α‐D‐glucopyranosid]uronate (3), and methyl O‐β‐D‐galactopyranosyl‐(1 → 2)‐O‐α‐L‐arabinopyranosyl‐(1 → 3)‐1,4‐anhydro‐α‐D‐glucopyranuronate (4). This method is useful for structure determination of some oleanane triterpenoid saponins and for yielding new oligosaccharides. The cleavage of the quillaic acid 3‐O‐glycoside 10 is also discussed.