Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, Rhode Island 02881, United States.
Dipartimento di Farmacia, Università di Napoli Federico II, Via D. Montesano 49, 80131 Napoli, Italy.
J Nat Prod. 2020 Sep 25;83(9):2664-2671. doi: 10.1021/acs.jnatprod.0c00550. Epub 2020 Aug 20.
The trichophycin family of compounds are chlorinated polyketides first discovered from environmental collections of a bloom-forming sp. cyanobacterium. In an effort to fully capture the chemical space of this group of metabolites, the utilization of MS/MS-based molecular networking of a extract revealed a metabolome replete with halogenated compounds. Subsequent MS-guided isolation resulted in the characterization of isotrichophycin C and trichophycins G-I (-). These new metabolites had intriguing structural variations from those trichophycins previously characterized, which allowed for a comparative study to examine structural features that are associated with toxicity to murine neuroblastoma cells. Additionally, we propose the absolute configuration of the previously characterized trichophycin A (). Overall, the metabolome of the bloom is hallmarked by an unprecedented amount of chlorinated molecules, many of which remain to be structurally characterized.
三曲菌素类化合物是首次从形成水华的蓝藻属的环境分离物中发现的氯化聚酮。为了充分捕获该组代谢物的化学空间,对 提取物进行基于 MS/MS 的分子网络分析,揭示了富含卤化化合物的代谢组。随后的 MS 引导分离导致了等三曲菌素 C 和三曲菌素 G-I(-)的特征化。这些新的代谢物与以前表征的三曲菌素具有有趣的结构变化,这使得可以进行比较研究以检查与对鼠神经母细胞瘤细胞的毒性相关的结构特征。此外,我们提出了先前表征的三曲菌素 A()的绝对构型。总体而言,该水华的代谢组以空前数量的氯化分子为特征,其中许多分子仍有待结构表征。