Massadine, a novel geranylgeranyltransferase type I inhibitor from the marine sponge Stylissa aff. massa

Shinichi Nishimura; Shigeki Matsunaga; Mitsuyoshi Shibazaki; Kenichi Suzuki; Kazuo Furihata; Rob W M van Soest; Nobuhiro Fusetani

doi:10.1021/ol034564u

Massadine, a novel geranylgeranyltransferase type I inhibitor from the marine sponge Stylissa aff. massa

Org Lett. 2003 Jun 26;5(13):2255-7. doi: 10.1021/ol034564u.

Authors

Shinichi Nishimura¹, Shigeki Matsunaga, Mitsuyoshi Shibazaki, Kenichi Suzuki, Kazuo Furihata, Rob W M van Soest, Nobuhiro Fusetani

Affiliation

¹ Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan.

PMID: 12816422
DOI: 10.1021/ol034564u

Abstract

Massadine, a highly oxygenated alkaloid, was isolated from the marine sponge Stylissa aff. massa as an inhibitor of geranylgeranyltransferase type I (GGTase I). The structure of massadine has been deduced from spectral data. Massidine inhibited GGTase I from Candida albicans with an IC(50) value of 3.9 microM. [structure: see text]

MeSH terms

Alkaloids / chemistry*
Alkaloids / isolation & purification
Alkaloids / pharmacology*
Alkyl and Aryl Transferases / antagonists & inhibitors*
Animals
Candida albicans / enzymology
Enzyme Inhibitors / chemistry*
Enzyme Inhibitors / isolation & purification
Enzyme Inhibitors / pharmacology*
Inhibitory Concentration 50
Magnetic Resonance Spectroscopy
Molecular Structure
Porifera / chemistry*
Protein Prenylation
Pyrroles / chemistry*
Pyrroles / isolation & purification*

Substances

Alkaloids
Enzyme Inhibitors
Pyrroles
massadine
Alkyl and Aryl Transferases
geranylgeranyltransferase type-I