Structures and Biosynthetic Pathway of Coprisamides C and D, 2-Alkenylcinnamic Acid-Containing Peptides from the Gut Bacterium of the Carrion Beetle Silpha perforata,Journal of Natural Products

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Structures and Biosynthetic Pathway of Coprisamides C and D, 2-Alkenylcinnamic Acid-Containing Peptides from the Gut Bacterium of the Carrion Beetle Silpha perforata
Journal of Natural Products ( IF 3.3 ) Pub Date : 2021-01-26 , DOI: 10.1021/acs.jnatprod.0c00864
Yern-Hyerk Shin ₁ , Yeon Hee Ban ₁ , Tae Ho Kim _{2,

3} , Eun Seo Bae ₁ , Jongheon Shin ₁ , Sang Kook Lee ₁ , Jichan Jang ₂ , Yeo Joon Yoon ₁ , Dong-Chan Oh ₁

Affiliation

Coprisamides C and D (1 and 2) were isolated from a gut bacterium, Micromonospora sp. UTJ3, of the carrion beetle Silpha perforata. Based on the combined analysis of UV, MS, and NMR spectral data, the planar structures of 1 and 2 were elucidated to be unreported derivatives of coprisamides A and B, cyclic depsipeptides bearing a 2-alkenylcinnamic acid unit and the unusual amino acids β-methylaspartic acid and 2,3-diaminopropanoic acid. The absolute configuration of 1 was determined using the advanced Marfey’s method, phenylglycine methyl ester derivatization, and J-based configuration analysis. The biosynthetic gene clusters for the coprisamides were investigated based on genomic data from coprisamide-producing strains Micromonospora sp. UTJ3 and Streptomyces sp. SNU533. Coprisamide C (1) was active against the Mycobacterium tuberculosis mc² 6230 strain.

中文翻译：

来自腐肉甲虫 Silpha perforata 肠道细菌的 Coprisamides C 和 D，含 2-烯基肉桂酸的肽的结构和生物合成途径

Coprisamides C 和 D（1和2）是从肠道细菌Micromonospora sp.中分离出来的。UTJ3，腐肉甲虫Silpha perforata。基于UV、MS和NMR光谱数据的综合分析，1和2的平面结构被阐明为未报道的coprisamides A和B衍生物、带有2-烯基肉桂酸单元的环状缩肽和不常见的氨基酸β-甲基天冬氨酸和 2,3-二氨基丙酸。的绝对构型1使用先进的Marfey法测定，苯基甘氨酸甲酯衍生化，和Ĵ基于配置的分析。基于来自产生coprisamide的菌株Micromonospora sp的基因组数据研究了coprisamides的生物合成基因簇。UTJ3 和链霉菌属。SNU533。Coprisamide C ( 1 ) 对结核分枝杆菌mc ² 6230 菌株具有活性。

更新日期：2021-02-26

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