Bezerramycins A-C, Antiproliferative Phenoxazinones from Streptomyces griseus Featuring Carboxy, Carboxamide or Nitrile Substituents

作者：Gomes Patricia Bezerra; Nett Markus; Dahse Hans Martin; Sattler Isabel; Martin Karin; Hertweck Christian^*

来源：European Journal of Organic Chemistry, 2010, (2): 231-235.

DOI：10.1002/ejoc.200901206

• Streptomyces griseus
• Antiproliferative activity
• Phenoxazinone
• Natural products
• Biosynthesis

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 ((1)H, (13)C, HSQC, (1)H-(1)H 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) (GI(50) = 14.5-20 mu m). A biosynthetic model for the isolated compounds is discussed.

• 出版日期2010-1