Isopentenoid synthesis in isolated embryonic Drosophila cells. Farnesol catabolism and omega-oxidation

J Biol Chem. 1988 Jan 25;263(3):1301-6.

Abstract

Kc cells divert minimally 40% of their mevalonate carbon to n-fatty acids and unidentified compounds covalently linked to macromolecules (Havel, C., Rector, E. R., II, and Watson, J. A. (1986) J. Biol. Chem. 261, 10150-10156). Furthermore mevalonate carbon diversion appears to occur at the polyprenyl 1-pyrophosphate level. This report summarizes initial efforts to define the mevalonate carbon diversion pathway. We demonstrate that Kc cell extracts readily metabolize [14C]farnesyl 1-pyrophosphate and [14C]farnesol, via common intermediates, to identical 14C-products. Two of the major 14C-products were identified as trans,trans-3,7,11-trimethyl-2,6,10-dodecatrien-1,12-dioic acid and trans-3,7-dimethyl-2,6-decadien-1,10-dioic acid. Similar acids were also synthesized by supplemented rat liver extracts incubated with [14C]farnesol. We conclude that (a) mevalonate carbon diversion at the level of polyprenyl 1-pyrophosphate is a viable metabolic strategy, (b) polyprenols are oxidized to alpha,omega-prenyl dicarboxylic acids which are catabolized from the omega-terminus, and (c) this metabolic process is not limited to insect cells.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Cell Line
  • Drosophila / metabolism*
  • Farnesol / metabolism*
  • Isomerism
  • Kinetics
  • Liver / metabolism
  • Male
  • Mevalonic Acid / metabolism
  • Oxidation-Reduction
  • Polyisoprenyl Phosphates / metabolism
  • Rats
  • Rats, Inbred Strains
  • Sesquiterpenes

Substances

  • Polyisoprenyl Phosphates
  • Sesquiterpenes
  • Farnesol
  • farnesyl pyrophosphate
  • Mevalonic Acid