Isolation and Computer-Based Structural Determination of Madangolide B

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-17 DOI:10.1021/acs.orglett.5c01955

Masahiro Hagihara, Jakia Jerin Mehjabin, Charles S. Vairappan, Tatsufumi Okino, Kiyotake Suenaga* and Arihiro Iwasaki*,

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Abstract

Madangolide (1) is a 17-membered cyclic enamide isolated from the marine cyanobacterium Lyngbya bouillonii. Since its discovery in 1999, the relative and absolute configurations of 1 have remained unknown. Here, we report the isolation, structural determination, and biological activity of a new analog of madangolide (1), madangolide B (2), from a marine Moorena sp. cyanobacterium. The planar structure of 2 was established using conventional two-dimensional NMR spectroscopy. The absolute configuration was clarified by comparing the experimental and theoretical data, including the chemical shifts, homonuclear and heteronuclear coupling constants, and ECD spectra. Based on the similarity of the NMR data, we proposed an absolute configuration of madangolide (1) and verified it through degradation and derivatization reactions. This study demonstrates the effectiveness of modern computational chemistry in revealing the stereochemistry of complex natural products with conformational flexibility.

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madmadolide B的分离与计算机结构测定。

Madangolide(1)是从海洋蓝细菌Lyngbya bouillonii中分离出来的17个成员的环酰胺。自1999年发现以来，1的相对构型和绝对构型一直是未知的。在这里，我们报道了从海洋Moorena sp.蓝藻中分离出一种新的madangolide类似物(1),madangolide B(2)的结构测定和生物活性。利用常规二维核磁共振波谱法确定了2的平面结构。通过比较实验数据和理论数据，包括化学位移、同核和异核耦合常数、ECD谱，明确了绝对构型。基于核磁共振数据的相似性，我们提出了madangolide(1)的绝对构型，并通过降解和衍生反应对其进行了验证。这项研究证明了现代计算化学在揭示具有构象灵活性的复杂天然产物的立体化学方面的有效性。

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

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.