cis-Dihydrodiol, arene oxide and phenol metabolites of dictamnine: key intermediates in the biodegradation and biosynthesis of furoquinoline alkaloids

Chem Commun (Camb). 2005 Aug 21:(31):3989-91. doi: 10.1039/b506944k. Epub 2005 Jul 11.

Abstract

Biotransformation of the parent furoquinoline alkaloid dictamnine and its 4-chlorofuroquinoline precursor, using the B8/36 bacterial mutant strain of Sphingomonas yanoikuyae, yielded, via biphenyl dioxygenase-catalysed dihydroxylation, the first isolable alkaloid cis-dihydrodiol metabolites; these metabolites were used in the chemoenzymatic synthesis of postulated arene oxide and phenol intermediates, and a range of derived furoquinoline alkaloids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / biosynthesis
  • Alkaloids / chemistry
  • Alkaloids / metabolism*
  • Naphthalenes / metabolism*
  • Oxides / metabolism*
  • Phenols / metabolism*
  • Quinolines / chemistry*
  • Quinolines / metabolism

Substances

  • Alkaloids
  • Naphthalenes
  • Oxides
  • Phenols
  • Quinolines
  • trans-1,2-dihydro-1,2-naphthalenediol
  • dictamnine