The Kavaratamides: Discovery of Linear Lipodepsipeptides from the Marine Cyanobacterium Moorena bouillonii Using a Comparative Chemogeographic Analysis

作者：Byeol Ryu, Evgenia Glukhov, Thaiz R. Teixeira, Conor R. Caffrey, Saranya Madiyan, Valsamma Joseph, Nicole E. Avalon, Christopher A. Leber, C. Benjamin Naman, William H. Gerwick · 发表于：Journal of Natural Products · 年份：2024 · DOI：10.1021/acs.jnatprod.4c00242 · 被引用次数：20 · 研究领域：Microbial Natural Products and Biosynthesis、Plant biochemistry and biosynthesis、Marine Sponges and Natural Products

High Resolution Image Download MS PowerPoint Slide Kavaratamide A ( 1 ), a new linear lipodepsipeptide possessing an unusual isopropyl- O -methylpyrrolinone moiety, was discovered from the tropical marine filamentous cyanobacterium Moorena bouillonii collected from Kavaratti, India. A comparative chemogeographic analysis of M . bouillonii collected from six different geographical regions led to the prioritized isolation of this metabolite from India as distinctive among our data sets. AI-based structure annotation tools, including SMART 2.1 and DeepSAT, accelerated the structure elucidation by providing useful structural clues, and the full planar structure was elucidated based on comprehensive HRMS, MS/MS fragmentation, and NMR data interpretation. Subsequently, the absolute configuration of 1 was determined using advanced Marfey’s analysis, modified Mosher’s ester derivatization, and chiral-phase HPLC. The structures of kavaratamides B ( 2 ) and C ( 3 ) are proposed based on a detailed analysis of their MS/MS fragmentations. The biological activity of kavaratamide A was also investigated and found to show moderate cytotoxicity to the D283-medullablastoma cell line.