Liu Hong-Bing, Lauro Gianluigi, O'Connor Robert D, Lohith Katheryn, Kelly Michelle, Colin Patrick, Bifulco Giuseppe, Bewley Carole A
Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health , Bethesda, Maryland 20892-0820, United States.
Dipartimento di Farmacia, Università di Salerno , 84084 Fisciano (SA), Italy.
J Nat Prod. 2017 Sep 22;80(9):2556-2560. doi: 10.1021/acs.jnatprod.7b00452. Epub 2017 Aug 24.
Antibacterial-guided fractionation of an extract of a deep-water Topsentia sp. marine sponge led to the isolation of two new indole alkaloids, tulongicin A (1) and dihydrospongotine C (2), along with two known analogues, spongotine C (3) and dibromodeoxytopsentin (4). Their planar structures were determined by NMR spectroscopy. Their absolute configurations were determined through a combination of experimental and computational analyses. Tulongicin (1) is the first natural product to contain a di(6-Br-1H-indol-3-yl)methyl group linked to an imidazole core. The coexistence of tri-indole 1 and bis-indole alcohol 2 suggests a possible route to 1. All of the compounds showed strong antimicrobial activity against Staphylococcus aureus.
对一种深水托普斯海绵属海洋海绵提取物进行抗菌导向分级分离，得到了两种新的吲哚生物碱，土龙菌素A（1）和二氢海绵托品C（2），以及两种已知类似物，海绵托品C（3）和二溴脱氧托普森汀（4）。通过核磁共振光谱确定了它们的平面结构。通过实验和计算分析相结合的方法确定了它们的绝对构型。土龙菌素（1）是第一个含有与咪唑核心相连的二（6-溴-1H-吲哚-3-基）甲基基团的天然产物。三吲哚1和双吲哚醇2的共存提示了一条合成1的可能途径。所有化合物对金黄色葡萄球菌均表现出较强的抗菌活性。
