Leibniz Institute for Natural Product Research and Infection Biology, Jena, Germany.
1] Leibniz Institute for Natural Product Research and Infection Biology, Jena, Germany [2] Chair for Natural Product Chemistry, Friedrich Schiller University, Jena, Germany.
J Antibiot (Tokyo). 2015 Jul;68(7):463-8. doi: 10.1038/ja.2015.10. Epub 2015 Feb 18.
Two new benzoxazines were isolated from Streptomyces griseus (HKI 0545) and assigned as chandrananimycin E (1) and dandamycin (2). Although a number of phenoxazinone-type compounds have been reported from nature, phenoxazines are rarer, and carbon substitution at N-10 such as in 1 is unprecedented. The cyclopentene-containing ring structure of dandamycin (2) is also unique. Chandrananimycin E (1) was found to possess moderate antiproliferative activity against HUVEC cells (GI50 35.3 μM) and weak cytotoxic activity towards HeLa cells (CC50 56.9 μM). Dandamycin showed neither antiproliferative activity nor cytotoxicity towards these cell lines. Structure activity comparisons with phenoxazinones isolated from S. griseus HKI 0545 suggested that the alteration of the core ring systems in 1 and 2 diminishes their activity. Natural products 1 and 2 are interesting additions to the rich secondary metabolome of S. griseus and constitute an important addition to the body of knowledge on phenoxazinone-derived metabolites.
从灰色链霉菌（HKI 0545）中分离得到两种新的苯并恶嗪，分别命名为 chandrananimycin E（1）和 dandamycin（2）。尽管已经从自然界中报道了许多 phenoxazinone 型化合物，但 phenoxazines 更为罕见，并且在 N-10 处的碳取代，如 1 中的情况，是前所未有的。dandamycin（2）中环戊烯的环结构也是独特的。chandrananimycin E（1）被发现对 HUVEC 细胞具有中等的抗增殖活性（GI50 为 35.3 μM），对 HeLa 细胞具有较弱的细胞毒性（CC50 为 56.9 μM）。dandamycin 对这些细胞系既没有抗增殖活性也没有细胞毒性。与从灰色链霉菌 HKI 0545 中分离出的 phenoxazinones 的结构活性比较表明，1 和 2 中核心环系统的改变降低了它们的活性。天然产物 1 和 2 是灰色链霉菌丰富次生代谢产物的有趣补充，也是 phenoxazinone 衍生代谢产物知识体系的重要补充。
