The streptazolin- and obscurolide-type metabolites from soil-derivedStreptomyces albonigerYIM20533 and the mechanism of influence of γ-butyrolactone on the growth ofStreptomycesby their non-enzymatic reaction biosynthesis
| Autor: | Na Luo, Zhong-Tao Ding, Cui-Ping Miao, Yi-Qing Li, Li-Hua Xu, Ya-Bin Yang, Xue-Qiong Yang, Li-Xing Zhao |
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| Rok vydání: | 2018 |
| Předmět: |
0301 basic medicine
biology 010405 organic chemistry Stereochemistry General Chemical Engineering 030106 microbiology Pentanone General Chemistry biology.organism_classification 01 natural sciences Streptomyces 0104 chemical sciences Acylation 03 medical and health sciences chemistry.chemical_compound Streptomyces alboniger Polyketide Biosynthesis chemistry Fermentation Streptazolin |
| Zdroj: | RSC Advances. 8:35042-35049 |
| ISSN: | 2046-2069 |
| DOI: | 10.1039/c8ra06690f |
| Popis: | Eleven new compounds with streptazolin- and obscurolide-type skeletons were isolated from soil-derived Streptomyces alboniger 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−1. 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 Streptomyces, and γ-butyrolactones were found to be hormones controlling antibiotic production in Streptomyces. In the pH fermentation tests, acylation of γ-butyrolactones was successfully used to explain the mechanism of influence on the growth of Streptomyces. |
| Databáze: | OpenAIRE |
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