A new oleanolic-type triterpene glycoside from Anchusa italica

Nat Prod Res. 2017 Apr;31(8):959-965. doi: 10.1080/14786419.2016.1258557. Epub 2016 Nov 20.

Abstract

A new oleanolic-type triterpene glycoside, (3β,21β)-21-[(β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl)oxy]-3-hydroxyolean-12-en-28-oic acid (1), together with five analogues, oleanazuroside 1 (2), oleanazuroside 2 (3), 24-hydroxytormentic acid ester glucoside (4), 24-epi-pinfaensin (5), and oleanolic acid 3-O-α-l-arabinoside (6) were isolated from the n-butyl alcohol extract of Anchusa italica. Their structures were determined spectroscopically and compared with previously reported spectral data. Compounds 3-4 and 6 were evaluated for their cytotoxic activities against five human cancer cell lines, but only compound 6 showed moderate cytotoxicity.

Keywords: Anchusa italica; Boraginaceae; cytotoxicity; triterpene glycoside.

MeSH terms

  • Antineoplastic Agents, Alkylating / chemistry
  • Antineoplastic Agents, Alkylating / isolation & purification
  • Antineoplastic Agents, Alkylating / pharmacology*
  • Boraginaceae / chemistry*
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor / methods
  • Glycosides / chemistry*
  • Glycosides / isolation & purification
  • Glycosides / pharmacology
  • Humans
  • Inhibitory Concentration 50
  • MCF-7 Cells / drug effects
  • Molecular Structure
  • Plant Extracts / chemistry
  • Triterpenes / chemistry*
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology

Substances

  • (3beta,21beta)-21-((beta-D-glucopyranosyl-(1-2)-beta-D-glucopyranosyl)oxy)-3-hydroxyolean-12-en-28-oic acid
  • 24-epi-pinfaensin
  • Antineoplastic Agents, Alkylating
  • Glycosides
  • Plant Extracts
  • Triterpenes
  • oleanolic acid 3-O-alpha-L-arabinoside