Anti-proliferative and anti-inflammatory prenylated isoflavones and coumaronochromones from the fruits of Ficus altissima

Bioorg Chem. 2021 Aug:113:104996. doi: 10.1016/j.bioorg.2021.104996. Epub 2021 May 18.

Abstract

Ficus altissima, an evergreen arbor belonging to the Moraceae family, is mainly cultivated in the tropics and subtropics of South and Southeast Asia with the characteristic of exuberant vitality and luxuriant foliage. In this article, four new prenylated isoflavones (1-4), along with ten previously described isoflavones (5-14) and two known prenylated coumaronochromones (15 and 16) were firstly obtained from the fruits of F. altissima. Their structures were identified by various spectroscopic techniques including specific optical rotation, HR-ESI-MS and NMR. The isolated products were evaluated for their anti-proliferative activities against three human tumor cell lines (HepG2, MCF-7 and MDA-MB-231) through MTT assay. Compounds 2, 3 and 16 exhibited obvious anti-proliferative activities against MDA-MB-231 cell line and compounds 3, 13 and 16 showed effective cytotoxic effects on HepG2 cell line in a concentration-dependent manner, as verified by the colony formation assay, cell and nucleus morphological assessment and apoptosis assay. Meanwhile, compounds 5 and 12 exhibited significant inhibition activities on NO production in LPS-stimulated RAW 264.7 cell line compared with positive control indometacin. The phytochemical investigation of the fruits of F. altissima in this study could provide the evidence for the discovery of lead compounds.

Keywords: Anti-inflammatory; Anti-proliferative; Coumaronochromone; Ficus altissima; Fruits; Isoflavone.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Apoptosis / drug effects
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Chromones / chemistry
  • Chromones / isolation & purification
  • Chromones / pharmacology*
  • Coumarins / chemistry
  • Coumarins / isolation & purification
  • Coumarins / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Ficus / chemistry*
  • Fruit / chemistry*
  • Humans
  • Isoflavones / chemistry
  • Isoflavones / isolation & purification
  • Isoflavones / pharmacology*
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Mice
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors
  • Nitric Oxide / biosynthesis
  • RAW 264.7 Cells
  • Structure-Activity Relationship

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Antineoplastic Agents, Phytogenic
  • Chromones
  • Coumarins
  • Isoflavones
  • Lipopolysaccharides
  • Nitric Oxide