New aminophenoxazinones from a marine Halomonas sp.: fermentation, structure elucidation, and biological activity

Jens Bitzer; Thomas Grosse; Linzhu Wang; Siegmund Lang; Winfried Beil; Axel Zeeck

doi:10.1038/ja.2006.12

New aminophenoxazinones from a marine Halomonas sp.: fermentation, structure elucidation, and biological activity

J Antibiot (Tokyo). 2006 Feb;59(2):86-92. doi: 10.1038/ja.2006.12.

Authors

Jens Bitzer¹, Thomas Grosse, Linzhu Wang, Siegmund Lang, Winfried Beil, Axel Zeeck

Affiliation

¹ Institute of Organic and Biomolecular Chemistry, University of Göttingen, Tammannstr. 2, D-37077 Göttingen, Germany.

PMID: 16629408
DOI: 10.1038/ja.2006.12

Abstract

The addition of anthranilic acid to the culture medium of the marine derived Halomonas sp. strain GWS-BW-H8hM completely altered the secondary metabolite pattern relative to the standard conditions. The red-orange color of the culture filtrate extract was the result of the production of 2-aminophenoxazin-3-one (1), chandrananimycin C (5) and three new derivatives of 1 with a previously unknown substitution pattern: 2-amino-, 2-amino-8-benzoyl-, and 2-amino-8-(4-hydroxybenzoyl)-6-hydroxyphenoxazin-3-one (2-4). The compounds were determined to have antibacterial and cytotoxic activities; a mode of action other than DNA intercalation is discussed.

Publication types

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

MeSH terms

Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / isolation & purification
Anti-Bacterial Agents / metabolism
Anti-Bacterial Agents / pharmacology*
Bacterial Toxins / metabolism
Bacterial Toxins / pharmacology
Candida albicans / drug effects*
Cell Cycle / drug effects
Cell Line, Tumor
Gammaproteobacteria / growth & development
Gammaproteobacteria / metabolism*
Gram-Positive Bacteria / drug effects*
Humans
Microbial Sensitivity Tests
Oxazines / chemistry
Oxazines / isolation & purification
Oxazines / metabolism
Oxazines / pharmacology*

Substances

Anti-Bacterial Agents
Bacterial Toxins
Oxazines
3-aminophenoxazone