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Short Communication
Bezerramycins A–C, Antiproliferative Phenoxazinones from Streptomyces griseus Featuring Carboxy, Carboxamide or Nitrile Substituents
Article first published online: 3 DEC 2009
DOI: 10.1002/ejoc.200901206
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Gomes, P. B., Nett, M., Dahse, H.-M., Sattler, I., Martin, K. and Hertweck, C. (2010), Bezerramycins A–C, Antiproliferative Phenoxazinones from Streptomyces griseus Featuring Carboxy, Carboxamide or Nitrile Substituents. Eur. J. Org. Chem., 2010: 231–235. doi: 10.1002/ejoc.200901206
Publication History
- Issue published online: 22 DEC 2009
- Article first published online: 3 DEC 2009
- Manuscript Received: 22 OCT 2009
Funded by
- DBU (Deutsche Bundesstiftung Umwelt)
Keywords:
- Streptomyces griseus;
- Antiproliferative activity;
- Phenoxazinone;
- Natural products;
- Biosynthesis
Abstract
Three new phenoxazinone antibiotics, named bezerramycins A–C (1–3), were isolated from a Streptomyces griseus strain (HKI 0545, DSM 41823) together with the known metabolite elloxazinone B (4). Their structures were elucidated by one- and two-dimensional NMR techniques (1H, 13C, HSQC, 1H-1H COSY and HMBC) as well as mass spectrometry. One of the isolated phenoxazinones (bezerramycin C) features a nitrile moiety, which is scarce in natural products. All compounds were evaluated for their antiproliferative and cytotoxic activities. Those featuring a hydroxymethyl substituent at C-8 were found to exhibit moderate antiproliferative properties against vascular endothelium cells (HUVEC) (GI50 = 14.5–20 μM). A biosynthetic model for the isolated compounds is discussed.