Relative and absolute stereochemistry of quinadoline B, an inhibitor of lipid droplet synthesis in macrophages

Nobuhiro Koyama; Yusuke Inoue; Masae Sekine; Yoichi Hayakawa; Hiroshi Homma; Satoshi Omura; Hiroshi Tomoda

doi:10.1021/ol802089p

Relative and absolute stereochemistry of quinadoline B, an inhibitor of lipid droplet synthesis in macrophages

Org Lett. 2008 Nov 20;10(22):5273-6. doi: 10.1021/ol802089p. Epub 2008 Oct 16.

Authors

Nobuhiro Koyama¹, Yusuke Inoue, Masae Sekine, Yoichi Hayakawa, Hiroshi Homma, Satoshi Omura, Hiroshi Tomoda

Affiliation

¹ School of Pharmacy, Kitasato University, Tokyo, Japan.

PMID: 18922003
DOI: 10.1021/ol802089p

Abstract

New fungal metabolites, designated quinadolines A (1) and B (2), were isolated from culture broth of Aspergillus sp. FKI-1746, and their structures were elucidated by NMR spectroscopy. The complete relative and absolute stereochemistry of 2 was determined by X-ray crystallography and amino acid analysis using a chiral column. Quinadolines moderately inhibited lipid droplet synthesis in mouse macrophages.

Publication types

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

MeSH terms

Animals
Aspergillus / chemistry
Heterocyclic Compounds, 3-Ring / chemistry*
Heterocyclic Compounds, 3-Ring / isolation & purification
Heterocyclic Compounds, 3-Ring / pharmacology*
Lipids / biosynthesis*
Macrophages / drug effects*
Macrophages / metabolism*
Magnetic Resonance Spectroscopy
Mice
Stereoisomerism

Substances

Heterocyclic Compounds, 3-Ring
Lipids
quinadoline B