Pentacyclic Antibiotics from a Tidal Mud Flat-Derived Actinomycete
- Authors
- Moon, Kyuho; Chung, Beomkoo; Shin, Yoonho; Rheingold, Arnold L.; Moore, Curtis E.; Park, Sung Jean; Park, Sunghyouk; Lee, Sang Kook; Oh, Ki-Bong; Shin, Jongheon; Oh, Dong-Chan
- Issue Date
- Mar-2015
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF NATURAL PRODUCTS, v.78, no.3, pp.524 - 529
- Journal Title
- JOURNAL OF NATURAL PRODUCTS
- Volume
- 78
- Number
- 3
- Start Page
- 524
- End Page
- 529
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/10721
- DOI
- 10.1021/np500736b
- ISSN
- 0163-3864
- Abstract
- The combination of investigating a unique source of chemically prolific bacterium with an LC/MS-based bacterial strain selection approach resulted in the discovery of two new secondary metabolites, buanmycin (1) and buanquinone (2), from the culture of a marine Streptomyces strain, which was isolated from a tidal mudflat in Buan, Republic of Korea. The carbon backbone of buanmycin (1), comprising 20 quaternary carbons out of 30 total carbons, was determined via C-13-C-13 COSY NMR analysis after labeling 1 with C-13 by culturing the bacterium with C-13-glucose. The complete structure of 1 was confidently elucidated, primarily based on 1D and 2D NMR spectroscopic and X-ray crystallographic analysis, as that of a new pentacyclic xanthone. The absolute configuration of the a-methyl serine unit in 1 was established by applying the advanced Marfey's method. The structure of buanquinone (2) was determined to be a new pentacyclic quinone based on NMR and MS spectroscopic data. Buanmycin exhibited potent cytotoxicity against colorectal carcinoma cells (HCT-116) and gastric carcinoma cells (SNU-638) with submicromolar IC50 values and strongly inhibited the pathogenic Gram-negative bacterium Salmonella enterica (MIC = 0.7 mu M). In particular, buanmycin demonstrated inhibition of sortase A, which is a promising target for antibiotic discovery.
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