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

• Published in: Journal of natural products (Washington, D.C.) Vol. 84; no. 2; pp. 239 - 246
• Main Authors: Shin, Yern-Hyerk, Ban, Yeon Hee, Kim, Tae Ho, Bae, Eun Seo, Shin, Jongheon, Lee, Sang Kook, Jang, Jichan, Yoon, Yeo Joon, Oh, Dong-Chan
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 26.02.2021; Amer Chemical Soc
• Subjects: Chemistry, Medicinal; Life Sciences & Biomedicine; Pharmacology & Pharmacy; Plant Sciences; Science & Technology
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/acs.jnatprod.0c00864

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.