Structures and Biosynthetic Pathway of Coprisamides C and D, 2-Alkenylcinnamic Acid-Containing Peptides from the Gut Bacterium of the Carrion Beetle Silpha perforata.
J Nat Prod
; 84(2): 239-246, 2021 02 26.
Article
en En
| MEDLINE
| ID: mdl-33497210
ABSTRACT
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 ß-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.
Texto completo:
1
Bases de datos:
MEDLINE
Asunto principal:
Péptidos Cíclicos
/
Escarabajos
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Depsipéptidos
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Microbioma Gastrointestinal
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Micromonospora
Límite:
Animals
País/Región como asunto:
Asia
Idioma:
En
Revista:
J Nat Prod
Año:
2021
Tipo del documento:
Article