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Serratiomycins D1-D3, Antibacterial Cyclic Peptides from a Serratia sp. and Structure Revision of Serratiomycin
- Title
- Serratiomycins D1-D3, Antibacterial Cyclic Peptides from a Serratia sp. and Structure Revision of Serratiomycin
- Authors
- Du; Young Eun; Cui; Jinsheng; Cho; Eunji; Hwang; Sunghoon; Jang; Yong-Joon; Oh; Ki-Bong; Nam; Sang-Jip; Dong-Chan
- Ewha Authors
- 남상집
- SCOPUS Author ID
- 남상집
- Issue Date
- 2024
- Journal Title
- Journal of Natural Products
- ISSN
- 1633-3864
- Citation
- Journal of Natural Products vol. 87, no. 5, pp. 1330 - 1337
- Indexed
- SCIE; SCOPUS
- Document Type
- Article
- Abstract
- Serratiomycin (1) is an antibacterial cyclic depsipeptide, first discovered from a Eubacterium culture in 1998. This compound was initially reported to contain l-Leu, l-Ser, l-allo-Thr, d-Phe, d-Ile, and hydroxydecanoic acid. In the present study, 1 and three new derivatives, serratiomycin D1-D3 (2-4), were isolated from a Serratia sp. strain isolated from the exoskeleton of a long-horned beetle. The planar structures of 1-4 were elucidated by using mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy. Comparison of the NMR chemical shifts and the physicochemical data of 1 to those of previously reported serratiomycin indeed identified 1 as serratiomycin. The absolute configurations of the amino units in compounds 1-4 were determined by the advanced Marfey’s method, 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate derivatization, and liquid chromatography-mass spectrometric (LC-MS) analysis. Additionally, methanolysis and the modified Mosher’s method were used to determine the absolute configuration of (3R)-hydroxydecanoic acid in 1. Consequently, the revised structure of 1 was found to possess d-Leu, l-Ser, l-Thr, d-Phe, l-allo-Ile, and d-hydroxydecanoic acid. In comparison with the previously published structure of serratiomycin, l-Leu, l-allo-Thr, and d-Ile in serratiomycin were revised to d-Leu, l-Thr, and l-allo-Ile. The new members of the serratiomycin family, compounds 2 and 3, showed considerably higher antibacterial activities against Staphylococcus aureus and Salmonella enterica than compound 1. © 2024 American Chemical Society and American Society of Pharmacognosy.
- DOI
- 10.1021/acs.jnatprod.3c00993
- Appears in Collections:
- 자연과학대학 > 화학·나노과학전공 > Journal papers
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