Acacia concinna Saponins. II. Structures of monoterpenoid glycosides in the alkaline hydrolysate of the saponin fraction

Fumiyuki Kiuchi, Abdul Gafur, Tohoru Obata, Akiko Tachibana, Yoshisuke Tsuda

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

From the AcOEt-soluble fraction of the alkaline hydrolyzate of the highly polar saponin fraction of pods of Acacia concinna, two monoterpenes, (2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid (menthiafolic acid, 1) and (2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid (4), and their glycosides, (6R)- and (6S)-menthiafolic acid-6-O-β-D-quinovoside (2a and 2b) and (6R)- and (6S)-menthiafolic acid-6-O-β-D-xyloside (3a and 3b), were isolated. A more polar fraction gave, after methylation with diazomethane, (6R)- and (6S)-(2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid- 6-O-β-D-quinovoside as their methyl esters (5a and 5b). Compounds 2a, 3a, 4, 5a, and 5b are new. The structures of the above compounds were determined mainly by the application of spectroscopic methods.

Original languageEnglish
Pages (from-to)807-812
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume45
Issue number5
DOIs
Publication statusPublished - 1997 May

Keywords

  • Acacia concinna
  • C-NMR
  • Menthiafolic acid
  • Monoterpene glycoside
  • β-D- quinovoside
  • β-D-xyloside

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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