Heliotropium bacciferum Forssk. (Boraginaceae) extracts: chemical constituents, antioxidant activity and cytotoxic effect in human cancer cell lines

Nat Prod Res. 2019 Jun;33(12):1813-1818. doi: 10.1080/14786419.2018.1437433. Epub 2018 Feb 12.

Abstract

Heliotropium bacciferum (Boraginaceae) is a perennial herb, growing in the Bechar region of Algeria, where it is traditionally used for skin diseases and tonsillitis. Herein, we report the isolation and characterization of sixteen secondary metabolites from the aerial part extracts. They include a sterol (1), megastigman type nor-isoprenoids (2, 3, 4, 6, 8, 10), C-11 terpene lactones (5 and 9), and a monoterpene (7) from the chloroform extract (HB-C); monoterpene glucoside (14), and phenolic compounds (11-13, 15, 16) from the methanol one (HB-M). Their structures were elucidated by spectroscopic methods including 1D and 2D NMR experiments, and ESIMS analysis. HB-M showed a significant and concentration dependent scavenging activity in vitro against the radicals DPPH and ABTS, related to the phenol derivatives (11-13, and 15-16), and HB-C inhibited the growth of colon cancer cell lines, mainly for the presence of the antiproliferative C-11 terpene lactones (5 and 9).

Keywords: Boraginaceae; antioxidant activity; cytotoxic effect; polyphenols; terpenoids.

Publication types

  • Video-Audio Media

MeSH terms

  • Algeria
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Cell Line, Tumor
  • Colonic Neoplasms / drug therapy
  • Colonic Neoplasms / pathology
  • Drug Evaluation, Preclinical
  • Drug Screening Assays, Antitumor
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / pharmacology
  • HCT116 Cells
  • Heliotropium / chemistry*
  • Heliotropium / metabolism
  • Humans
  • Molecular Structure
  • Phenols / analysis
  • Phenols / chemistry
  • Plant Extracts / chemistry
  • Plants, Medicinal / chemistry
  • Plants, Medicinal / metabolism
  • Secondary Metabolism
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Antineoplastic Agents, Phytogenic
  • Antioxidants
  • Free Radical Scavengers
  • Phenols
  • Plant Extracts