Absolute stereochemistry of pentacecilides, new inhibitors of lipid droplet formation in mouse macrophages, produced by Penicillium cecidicola FKI-3765-1

Hiroyuki Yamazaki; Narihiro Ugaki; Daisuke Matsuda; Hiroshi Tomoda

doi:10.1038/ja.2010.39

Absolute stereochemistry of pentacecilides, new inhibitors of lipid droplet formation in mouse macrophages, produced by Penicillium cecidicola FKI-3765-1

J Antibiot (Tokyo). 2010 Jun;63(6):315-8. doi: 10.1038/ja.2010.39. Epub 2010 Apr 23.

Authors

Hiroyuki Yamazaki¹, Narihiro Ugaki, Daisuke Matsuda, Hiroshi Tomoda

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Kitasato University, Minato-ku, Tokyo, Japan.

PMID: 20414320
DOI: 10.1038/ja.2010.39

Abstract

The structure of a new pentacecilide congener, pentacecilide D, produced by Penicillium cecidicola FKI-3765-1 was elucidated by various NMR experiments. The absolute stereochemistry of pentacecilides was elucidated by using the modified Mosher method for pentacecilide C. The inhibitory activity of all pentacecilides against lipid droplet formation and acyl-CoA:cholesterol acyltransferase isozymes was compared.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
CHO Cells / drug effects
Cholesterol Esters / biosynthesis
Cricetinae
Cricetulus
Hypolipidemic Agents / chemistry*
Hypolipidemic Agents / isolation & purification
Hypolipidemic Agents / pharmacology
Lipid Metabolism / drug effects*
Macrophages / drug effects*
Mice
Nuclear Magnetic Resonance, Biomolecular
Penicillium / metabolism*
Sesquiterpenes / chemistry*
Sesquiterpenes / isolation & purification
Sesquiterpenes / pharmacology
Stereoisomerism

Substances

Cholesterol Esters
Hypolipidemic Agents
Sesquiterpenes
pentacecilide A
pentacecilide B
pentacecilide C
pentacecilide D