Structural determination of two new acacic acid-type saponins from the stem barks of Albizia zygia (DC.) J. F. Macbr

Nat Prod Res. 2019 Jan;33(2):180-188. doi: 10.1080/14786419.2018.1440228. Epub 2018 Feb 19.

Abstract

As a continuation of our interest in the study of triterpenoid saponins from Albizia zygia, phytochemical investigation of its stem barks led to the isolation of two new oleanane-type saponins, named zygiaosides C-D (1-2). Their structures were established on the basis of extensive analysis of 1D and 2D NMR (1H-, 13C NMR, DEPT, COSY, TOCSY, ROESY, HSQC and HMBC) experiments, HRESIMS studies, and by chemical evidence as, 3-O-[ β-d-glucopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→6)]-β-d-glucopyranosyl]-21-O-[(2E,6S)-2,6-dimethyl-6-O-(β-d-quinovopyranosyl) octa-2,7-dienoyl]acacic acid 28-O-α-l-arabinofuranosyl-(1→4)-[β-d-glucopyranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl ester (1) and 3- O-[β-d-glucopyranosyl-(1→2) -[ β-d-fucopyranosyl-(1→6)]-β-d-glucopyranosyl]-21-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl) octa-2,7-dienoyl]acacic acid 28-O-α-l-arabinofuranosyl-(1→4)-[β-d-glucopyranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl ester (2).

Keywords: 1D and 2D NMR; acacic acid-type saponins; mimosaceae; triterpenoid saponins.

MeSH terms

  • Albizzia / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oleanolic Acid / analogs & derivatives
  • Oleanolic Acid / chemistry
  • Plant Bark / chemistry
  • Saponins / chemistry*
  • Saponins / isolation & purification
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Saponins
  • oleanane
  • Oleanolic Acid