Influenza A (H(1)N(1)) Antiviral and Cytotoxic Agents from Ferula assa-foetida

J Nat Prod. 2009 Sep;72(9):1568-72. doi: 10.1021/np900158f.

Abstract

Two new sesquiterpene coumarins, designated 5'-acetoxy-8'-hydroxyumbelliprenin (1) and 10'R-acetoxy-11'-hydroxyumbelliprenin (2), and a new diterpene, 15-hydroxy-6-en-dehydroabietic acid (3), along with 27 known compounds, were isolated from a CHCl(3)-soluble extract of Ferula assa-foetida through bioassay-guided fractionation. The structures of the new metabolites 1-3 were identified by spectroscopic data interpretation and by the Mosher ester method. Compounds 4 and 6-13 showed greater potency against influenza A virus (H(1)N(1)) (IC(50) 0.26-0.86 microg/mL) than amantadine (IC(50) 0.92 microg/mL), and 11 exhibited the best potency (IC(50) 0.51, 2.6, and 3.4 microg/mL) of these compounds against the HepG2, Hep3B, and MCF-7 cancer cell lines, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Antiviral Agents / chemistry
  • Antiviral Agents / isolation & purification*
  • Antiviral Agents / pharmacology*
  • Chlorocebus aethiops
  • Coumarins / chemistry
  • Coumarins / isolation & purification*
  • Coumarins / pharmacology*
  • Ferula / chemistry*
  • Humans
  • Influenza A Virus, H1N1 Subtype / drug effects*
  • Influenza, Human / drug therapy*
  • Molecular Structure
  • Plants, Medicinal / chemistry*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology*

Substances

  • 10'R-acetoxy-11'-hydroxyumbelliprenin
  • 5'-acetoxy-8'-hydroxyumbelliprenin
  • Antineoplastic Agents, Phytogenic
  • Antiviral Agents
  • Coumarins
  • Sesquiterpenes