Phallusialides A-E, Pyrrole-Derived Alkaloids Discovered from a Marine-Derived Micromonospora sp. Bacterium Using MS-Based Metabolomics Approaches.,Journal of Natural Products

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Phallusialides A-E, Pyrrole-Derived Alkaloids Discovered from a Marine-Derived Micromonospora sp. Bacterium Using MS-Based Metabolomics Approaches.
Journal of Natural Products ( IF 3.3 ) Pub Date : 2019-12-03 , DOI: 10.1021/acs.jnatprod.9b00808
Fan Zhang ₁ , Doug R Braun ₁ , Shaurya Chanana ₁ , Scott R Rajski ₁ , Tim S Bugni ₁

Affiliation

Integrating MS-based metabolomics approaches, LC-MS-PCA and molecular networking enabled the targeted isolation of five new pyrrole-derived alkaloids, phallusialides A-E (1-5), from a marine-derived Micromonospora sp. bacterium. The structures of 1-5 were elucidated by analysis of their HRMS, MS/MS, and NMR spectroscopic data. The absolute configuration of phallusialide A (1) was determined on the basis of comparisons of experimental and theoretically calculated ECD spectra. Compounds 1 and 2 exhibited antibacterial activity against methicillin resistant S. aureus (MRSA) and E. coli, with MIC values of 32 and 64 μg/mL, respectively, whereas 3-5 showed no antibacterial activity even at 256 μg/mL, yielding important SAR insights for this class of compounds.

中文翻译：

Phallusialides AE，从海洋来源的小单孢菌中发现的吡咯衍生生物碱。使用基于 MS 的代谢组学方法研究细菌。

整合基于 MS 的代谢组学方法、LC-MS-PCA 和分子网络，能够从海洋来源的小单孢菌中定向分离五种新的吡咯衍生生物碱，即鬼笔内酯 AE (1-5)。细菌。通过分析 HRMS、MS/MS 和 NMR 光谱数据，阐明了 1-5 的结构。根据实验和理论计算的 ECD 光谱的比较，确定了 Phallusialide A (1) 的绝对构型。化合物 1 和 2 对耐甲氧西林金黄色葡萄球菌 (MRSA) 和大肠杆菌表现出抗菌活性，MIC 值分别为 32 和 64 μg/mL，而 3-5 即使在 256 μg/mL 下也没有表现出抗菌活性，产生对此类化合物的重要 SAR 见解。

更新日期：2019-12-04

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