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海洋三吲哚生物碱土龙霉素A的全合成及抗菌活性

Total Synthesis and Antibacterial Activity of Marine Tris-indole Alkaloid Tulongicin A.

作者信息

Tsuruda Shuji, Sato Takumi, Aoyama Hiroshi, Sirimangkalakitti Natchanun, Fujimura Shigeru, Arisawa Mitsuhiro, Murai Kenichi

机构信息

Graduate School of Pharmaceutical Sciences, Osaka University, Suita, Osaka 565-0871, Japan.

Division of Clinical Infectious Diseases & Chemotherapy, Tohoku Medical and Pharmaceutical University, Sendai 981-8558, Japan.

出版信息

J Nat Prod. 2024 Jun 28;87(6):1556-1562. doi: 10.1021/acs.jnatprod.4c00129. Epub 2024 May 17.

Abstract

Bis-indole alkaloids from marine sponges are an intriguing class of natural products with a variety of activities. However, only a preliminary biological study of tulongicin A (), a related previously isolated marine tris-indole alkaloid, has been conducted. In this study, we accomplished the first asymmetric total synthesis of via the construction of an imidazoline-linked bis-indolylmethane skeleton using a Friedel-Crafts-type reaction. Our synthesis enabled a detailed study of the antibacterial profile of . Compound displayed bactericidal activity against , including methicillin-resistant (MRSA) strains.

摘要

来自海洋海绵的双吲哚生物碱是一类具有多种活性的有趣天然产物。然而,对于之前分离得到的相关海洋三吲哚生物碱土龙菌素A()仅进行了初步的生物学研究。在本研究中,我们通过使用傅克型反应构建咪唑啉连接的双吲哚甲烷骨架,首次完成了的不对称全合成。我们的合成使得能够对的抗菌谱进行详细研究。化合物对包括耐甲氧西林金黄色葡萄球菌(MRSA)菌株在内的表现出杀菌活性。

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