The streptazolin- and obscurolide-type metabolites from soil-derived Streptomyces alboniger YIM20533 and the mechanism of influence of γ-butyrolactone on the growth of Streptomyces by their non-enzymatic reaction biosynthesis

Eleven new compounds with streptazolin- and obscurolide-type skeletons were isolated from soil-derived obtained from Tibet, China. Two types of unprecedented skeletons of obscurolide dimer and an obscurolide-type compound with an aromatic polyketide of pentanone substituted at the benzene ring were...

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Bibliographic Details
Published in:RSC advances 2018-10, Vol.8 (61), p.35042-35049
Main Authors: Luo, Na, Yang, Ya-Bin, Yang, Xue-Qiong, Miao, Cui-Ping, Li, Yi-Qing, Xu, Li-Hua, Ding, Zhong-Tao, Zhao, Li-Xing
Format: Article
Language:English
Subjects:
Acylation
Antibiotics
Aromatic compounds
Benzene
Biosynthesis
Butyrolactone
Chemistry
Data analysis
Dimers
Fermentation
Hormones
Macrophages
Metabolites
Nitric oxide
NMR
Nuclear magnetic resonance
Pentanone
Spectra
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Summary:Eleven new compounds with streptazolin- and obscurolide-type skeletons were isolated from soil-derived obtained from Tibet, China. Two types of unprecedented skeletons of obscurolide dimer and an obscurolide-type compound with an aromatic polyketide of pentanone substituted at the benzene ring were determined by spectral data analysis. Compound 11 was the first evidence of two nitrogens in streptazolin-type structures. Compound 1 indicated an inhibitory effect on nitric oxide production in LPS-activated macrophages with an inhibition ratio of 51.7% at 50 μM, and on anticoagulant activity on platelet activating factor (PAF)-induced platelet aggregation with an inhibition ratio of 26.0 ± 9.1% at 200 μg mL . 11 had anti-acetylcholinesterase activity with an inhibition ratio of 27.2% at a concentration of 50 μM. Mechanistic aspects of the non-enzymatic reaction as well as a more detailed picture of the biosynthetic relationships of the streptazolin- and obscurolide-type metabolites are described. Acidic and basic conditions can inhibit the growth of , and γ-butyrolactones were found to be hormones controlling antibiotic production in . In the pH fermentation tests, acylation of γ-butyrolactones was successfully used to explain the mechanism of influence on the growth of .
ISSN:2046-2069
2046-2069
DOI:10.1039/c8ra06690f