Hydroxylation at carbon-2 of ent-16-oxo-17-norkauran-19-oic acid by Fusarium proliferatum

J Nat Prod. 2010 Aug 27;73(8):1431-3. doi: 10.1021/np100134f.

Abstract

A new product of biotransformation of ent-16-oxo-17-norkauran-19-oic acid (1) by Fusarium proliferatum was isolated and identified as a 2beta-hydroxy derivative (2). The structure of 2 was elucidated on the basis of spectroscopic data interpretation and single-crystal X-ray diffraction analysis. The allelopathic activity of compound 2 was evaluated on the growth of radicals and shoots of Lactuca sativa (lettuce). This is the first time that fungal hydroxylation at position C-2 has been reported on an ent-kaurane diterpene skeleton.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biotransformation
  • Brazil
  • Crystallography, X-Ray
  • Diterpenes, Kaurane / chemistry*
  • Fusarium / metabolism*
  • Hydroxylation
  • Lactuca / drug effects*
  • Lactuca / growth & development
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Wedelia / chemistry

Substances

  • 2beta-hydroxy, ent-16-oxo-17-norkauran-19-oic acid
  • Diterpenes, Kaurane
  • ent-16-oxo-17-norkauran-19-oic acid