B-535a, b and c, new sphingosine kinase inhibitors, produced by a marine bacterium; taxonomy, fermentation, isolation, physico-chemical properties and structure determination

K Kono; M Tanaka; T Mizuno; K Kodama; T Ogita; T Kohama

doi:10.7164/antibiotics.53.753

B-535a, b and c, new sphingosine kinase inhibitors, produced by a marine bacterium; taxonomy, fermentation, isolation, physico-chemical properties and structure determination

J Antibiot (Tokyo). 2000 Aug;53(8):753-8. doi: 10.7164/antibiotics.53.753.

Authors

K Kono¹, M Tanaka, T Mizuno, K Kodama, T Ogita, T Kohama

Affiliation

¹ Pharmacology and Molecular Biology Research Laboratories, Research Institute, Sankyo Co., Ltd., Shinagawa, Tokyo, Japan.

PMID: 11079796
DOI: 10.7164/antibiotics.53.753

Abstract

In the course of our screening for inhibitors of sphingosine kinase, we found a series of active compounds in a culture broth of a novel marine bacterium, SANK 71896. The structures of the compounds, named B-5354a, b and c, were elucidated by a combination of spectroscopic analyses to be new esters of 4-amino-3-hydroxybenzoic acid with long-chain unsaturated alcohols. B-5354a, b and c inhibit sphingosine kinase activity with IC50 values of 21, 58 and 38 microm, respectively.

MeSH terms

4-Aminobenzoic Acid / chemistry
4-Aminobenzoic Acid / isolation & purification
4-Aminobenzoic Acid / pharmacology
Animals
Cell-Free System
Enzyme Inhibitors / chemistry*
Enzyme Inhibitors / isolation & purification
Enzyme Inhibitors / pharmacology*
Fermentation
Gram-Negative Bacteria / classification
Gram-Negative Bacteria / metabolism*
Inhibitory Concentration 50
Molecular Structure
Phosphotransferases (Alcohol Group Acceptor) / antagonists & inhibitors*
Rats
Water Microbiology
para-Aminobenzoates*

Substances

B 5354a
B 5354b
B 5354c
Enzyme Inhibitors
para-Aminobenzoates
Phosphotransferases (Alcohol Group Acceptor)
sphingosine kinase
4-Aminobenzoic Acid