Quintaquinone, a Merosesquiterpene from the Yellow Sponge Verongula cf. rigida Esper

J Nat Prod. 2020 Feb 28;83(2):532-536. doi: 10.1021/acs.jnatprod.9b00886. Epub 2020 Feb 10.

Abstract

A chemical investigation of the sponge Verongula cf. rigida led to the isolation of 13 merosesquiterpenes, among which quintaquinone (2), 5-epi-nakijiquinone L (3), and 3-farnesyl-2-hydroxy-5-methoxyquinone (4) were isolated and reported here for the first time. Particularly, compound 2 is the first member of merosesquiterpenes with a polyketide side chain substituted on C-19. All of the isolated compounds were examined for steroid 5α-reductase inhibitory activity. Cyclospongiaquinone 1 (5) showed a strong activity in the same range as that of standard finasteride.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 5-alpha Reductase Inhibitors / chemistry
  • 5-alpha Reductase Inhibitors / isolation & purification
  • 5-alpha Reductase Inhibitors / pharmacology*
  • Animals
  • Finasteride / chemistry
  • Finasteride / isolation & purification
  • Finasteride / pharmacology*
  • Humans
  • Male
  • Molecular Structure
  • Porifera / chemistry
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology

Substances

  • 5-alpha Reductase Inhibitors
  • Sesquiterpenes
  • cyclospongiaquinone-1
  • Finasteride