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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 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...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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The Royal Society of Chemistry
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9087211/ https://www.ncbi.nlm.nih.gov/pubmed/35547034 http://dx.doi.org/10.1039/c8ra06690f |
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author | Luo, Na Yang, Ya-Bin Yang, Xue-Qiong Miao, Cui-Ping Li, Yi-Qing Xu, Li-Hua Ding, Zhong-Tao Zhao, Li-Xing |
author_facet | Luo, Na Yang, Ya-Bin Yang, Xue-Qiong Miao, Cui-Ping Li, Yi-Qing Xu, Li-Hua Ding, Zhong-Tao Zhao, Li-Xing |
author_sort | Luo, Na |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-9087211 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-90872112022-05-10 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 Luo, Na Yang, Ya-Bin Yang, Xue-Qiong Miao, Cui-Ping Li, Yi-Qing Xu, Li-Hua Ding, Zhong-Tao Zhao, Li-Xing RSC Adv Chemistry 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. The Royal Society of Chemistry 2018-10-12 /pmc/articles/PMC9087211/ /pubmed/35547034 http://dx.doi.org/10.1039/c8ra06690f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Luo, Na Yang, Ya-Bin Yang, Xue-Qiong Miao, Cui-Ping Li, Yi-Qing Xu, Li-Hua Ding, Zhong-Tao Zhao, Li-Xing 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 |
title | 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 |
title_full | 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 |
title_fullStr | 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 |
title_full_unstemmed | 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 |
title_short | 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 |
title_sort | 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 |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9087211/ https://www.ncbi.nlm.nih.gov/pubmed/35547034 http://dx.doi.org/10.1039/c8ra06690f |
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