腐肉甲虫肠道细菌来源的含 2-烯丙基肉桂酸的肽类化合物 Coprisamides C 和 D 的结构和生物合成途径
Structures and Biosynthetic Pathway of Coprisamides C and D, 2-Alkenylcinnamic Acid-Containing Peptides from the Gut Bacterium of the Carrion Beetle .
机构信息
Natural Products Research Institute, College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Republic of Korea.
Molecular Mechanism of Antibiotics, Division of Life Science, Research Institute of Life Science, Gyeongsang National University, Jinju 52828, Republic of Korea.
出版信息
J Nat Prod. 2021 Feb 26;84(2):239-246. doi: 10.1021/acs.jnatprod.0c00864. Epub 2021 Jan 26.
Coprisamides C and D ( and ) were isolated from a gut bacterium, sp. UTJ3, of the carrion beetle . Based on the combined analysis of UV, MS, and NMR spectral data, the planar structures of and 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 was determined using the advanced Marfey's method, phenylglycine methyl ester derivatization, and -based configuration analysis. The biosynthetic gene clusters for the coprisamides were investigated based on genomic data from coprisamide-producing strains sp. UTJ3 and sp. SNU533. Coprisamide C () was active against the mc 6230 strain.
Coprisamides C 和 D (and) 从 carrion beetle 的肠道细菌 sp. UTJ3 中分离得到。基于 UV、MS 和 NMR 光谱数据的综合分析，确定了 和 的平面结构为未报道的 coprisamides A 和 B 的衍生物，它们是具有 2-烯基肉桂酸单元和不常见氨基酸 β-甲基天冬氨酸和 2,3-二氨基丙酸的环状 depsipeptides。通过先进的 Marfey 方法、苯甘氨酸甲酯衍生化和基于 -的构型分析，确定了 的绝对构型。根据 coprisamide 产生菌株 sp. UTJ3 和 sp. SNU533 的基因组数据，研究了 coprisamides 的生物合成基因簇。Coprisamide C () 对 mc 6230 菌株具有活性。
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