Regulation of HMGCoA reductase activity by policosanol and octacosadienol, a new synthetic analogue of octacosanol

Simonetta Oliaro-Bosso, Emanuela Calcio Gaudino, Stefano Mantegna, Enrico Giraudo, Claudia Meda, Franca Viola, Giancarlo Cravotto

Research output: Contribution to journalArticlepeer-review

Abstract

Octacosa-10,19-dien-1-ol is a newly synthesized long-chain alcohol, an unsaturated analogue of 1-octacosanol, the major component of policosanol, the purified natural mixture of different higher aliphatic alcohols obtained from sugarcane wax. Our efficient synthetic protocol (five steps with 50% overall yield) is well suited for gram scale preparations and a rapid generation of analogues with different degrees of unsaturation. Beneficial effects of policosanol in the prevention of atherosclerosis and thromboembolic disorders have been reported and related to the inhibition of sterol biosynthesis possibly by the regulation of the activity of HMGCoA reductase mediated by AMP-dependent kinase AMPK. We have compared the effect of octacosadienol and policosanol on the regulation of HMGCoA reductase in HUVEC and HepG2 human hepatoma cells. Octacosadienol was as effective as policosanol in inhibiting the upregulation of HMGCoA reductase, in inducing the phosphorylation of AMPK and in downregulating the HMGCoA reductase mRNA.

Original languageEnglish
Pages (from-to)907-916
Number of pages10
JournalLipids
Volume44
Issue number10
DOIs
Publication statusPublished - Oct 2009

Keywords

  • AMPK phosphorylation
  • HMGCoA reductase
  • Long-chain alcohols synthesis
  • Octacosadienol
  • Octacosanol
  • Policosanol

ASJC Scopus subject areas

  • Biochemistry
  • Cell Biology
  • Organic Chemistry

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