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A New Cleavage Method for the Sugar – Aglycone Linkage in Saponin
Author(s) -
Higuchi Ryuichi,
Tokimitsu Yoshinori,
Hamada Naoko,
Komori Tetsuya,
Kawasaki Toshio
Publication year - 1985
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198519850609
Subject(s) - aglycone , chemistry , saponin , diazomethane , glycoside , stereochemistry , uronic acid , ether , cleavage (geology) , oleanane , methanol , sugar , triterpene , organic chemistry , polysaccharide , medicine , alternative medicine , geotechnical engineering , pathology , fracture (geology) , engineering
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.