Schulzeines A-C, new alpha-glucosidase inhibitors from the marine sponge Penares schulzei

Kentaro Takada; Taisuke Uehara; Yoichi Nakao; Shigeki Matsunaga; Rob W M van Soest; Nobuhiro Fusetani

doi:10.1021/ja037368r

Schulzeines A-C, new alpha-glucosidase inhibitors from the marine sponge Penares schulzei

J Am Chem Soc. 2004 Jan 14;126(1):187-93. doi: 10.1021/ja037368r.

Authors

Kentaro Takada¹, Taisuke Uehara, Yoichi Nakao, Shigeki Matsunaga, 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: 14709083
DOI: 10.1021/ja037368r

Abstract

Three new alpha-glucosidase inhibitors, schulzeines A-C (1-3), were isolated from the marine sponge Penares schulzei. Their structures were elucidated by spectral analysis and chemical degradations to be the isoquinoline alkaloids, encompassing two amino acids, and C(28) fatty acid, the last of which was sulfated. Absolute stereochemistry of schulzeines was determined by application of the modified Mosher analysis to fragments obtained by chemical degradation. Schulzeines A-C inhibit alpha-glucosidase with IC(50) values of 48-170 nM.

Publication types

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

MeSH terms

Alkaloids / chemistry
Alkaloids / isolation & purification
Alkaloids / pharmacology
Animals
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / isolation & purification*
Enzyme Inhibitors / pharmacology
Fatty Acids / chemistry
Fatty Acids / isolation & purification
Fatty Acids / pharmacology
Glycoside Hydrolase Inhibitors*
Isoquinolines / chemistry
Isoquinolines / isolation & purification*
Isoquinolines / pharmacology
Models, Molecular
Nuclear Magnetic Resonance, Biomolecular
Porifera / chemistry*

Substances

Alkaloids
Enzyme Inhibitors
Fatty Acids
Glycoside Hydrolase Inhibitors
Isoquinolines