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

IF 3.6 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2024-06-04 DOI:10.1021/acs.jnatprod.4c00242

Byeol Ryu, Evgenia Glukhov, Thaiz R. Teixeira, Conor R. Caffrey, Saranya Madiyan, Valsamma Joseph, Nicole E. Avalon, Christopher A. Leber, C. Benjamin Naman and William H. Gerwick*,

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Abstract

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.

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Kavaratamides：利用比较化学地理分析法从海洋蓝藻 Moorena bouillonii 中发现线性脂十二肽。

Kavaratamide A (1)是一种新的线性脂二肽，具有一个不寻常的异丙基-O-甲基吡咯烷酮分子，是从印度卡瓦拉蒂采集的热带海洋丝状蓝藻 Moorena bouillonii 中发现的。通过对从六个不同地理区域收集的 M. bouillonii 进行化学地理学比较分析，在我们的数据集中优先从印度分离出了这种独特的代谢物。基于人工智能的结构注释工具，包括 SMART 2.1 和 DeepSAT，通过提供有用的结构线索加速了结构的阐明，并根据全面的 HRMS、MS/MS 片段和 NMR 数据解释阐明了完整的平面结构。随后，利用先进的马菲分析法、改进的莫舍酯衍生法和手性相高效液相色谱法确定了 1 的绝对构型。根据对其 MS/MS 片段的详细分析，提出了卡伐他胺 B (2) 和 C (3) 的结构。此外，还对卡伐他胺 A 的生物活性进行了研究，发现它对 D283 髓母细胞瘤细胞系具有适度的细胞毒性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.