Biomedicinal Information Research Center (BIRC), Japan Biological Informatics Consortium (JBIC), 2-4-7 Aomi, Koto-ku, Tokyo 135-0064, Japan.
J Nat Prod. 2011 Jul 22;74(7):1630-5. doi: 10.1021/np200386c. Epub 2011 Jul 5.
Strain SpD081030SC-03, representing a novel species of Streptomyces, was isolated from a marine sponge. Two 3,5,6-trisubstituted 2(1H)-pyrazinones, JBIR-56 (1) and JBIR-57 (2), were isolated from a culture of SpD081030SC-03. The planar structures of 1 and 2 were assigned on the basis of extensive NMR and MS analyses. In addition, analyses of the methylated derivative of 1 confirmed a 3,5,6-trisubstituted 2(1H)-pyrazinone moiety. The absolute configurations of the amino acid residues were determined by application of Marfey's method. Because 1 did not appear to comprise the normal connection of amino acid units, we confirmed its structure by the total synthesis of 1. Biosynthetically, 1 consists of a unique skeleton connected to the peptide chain at C-5 of the pyrazinone ring.
菌株 SpD081030SC-03 代表一种新型链霉菌，从海洋海绵中分离得到。从 SpD081030SC-03 的培养物中分离出两种 3,5,6-三取代的 2(1H)-吡嗪酮，JBIR-56（1）和 JBIR-57（2）。根据广泛的 NMR 和 MS 分析，确定了 1 和 2 的平面结构。此外，对 1 的甲基化衍生物的分析证实了 3,5,6-三取代的 2(1H)-吡嗪酮部分。通过应用 Marfey 法确定了氨基酸残基的绝对构型。由于 1 似乎不包含氨基酸单元的正常连接，我们通过 1 的全合成来证实其结构。生物合成上，1 由独特的骨架与吡嗪酮环 C-5 上的肽链相连。
