Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Luo, Na, Yang, Ya-Bin, Yang, Xue-Qiong, Miao, Cui-Ping, Li, Yi-Qing, Xu, Li-Hua, Ding, Zhong-Tao, Zhao, Li-Xing
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
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
_version_ 1784704153590693888
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
work_keys_str_mv AT luona thestreptazolinandobscurolidetypemetabolitesfromsoilderivedstreptomycesalbonigeryim20533andthemechanismofinfluenceofgbutyrolactoneonthegrowthofstreptomycesbytheirnonenzymaticreactionbiosynthesis
AT yangyabin thestreptazolinandobscurolidetypemetabolitesfromsoilderivedstreptomycesalbonigeryim20533andthemechanismofinfluenceofgbutyrolactoneonthegrowthofstreptomycesbytheirnonenzymaticreactionbiosynthesis
AT yangxueqiong thestreptazolinandobscurolidetypemetabolitesfromsoilderivedstreptomycesalbonigeryim20533andthemechanismofinfluenceofgbutyrolactoneonthegrowthofstreptomycesbytheirnonenzymaticreactionbiosynthesis
AT miaocuiping thestreptazolinandobscurolidetypemetabolitesfromsoilderivedstreptomycesalbonigeryim20533andthemechanismofinfluenceofgbutyrolactoneonthegrowthofstreptomycesbytheirnonenzymaticreactionbiosynthesis
AT liyiqing thestreptazolinandobscurolidetypemetabolitesfromsoilderivedstreptomycesalbonigeryim20533andthemechanismofinfluenceofgbutyrolactoneonthegrowthofstreptomycesbytheirnonenzymaticreactionbiosynthesis
AT xulihua thestreptazolinandobscurolidetypemetabolitesfromsoilderivedstreptomycesalbonigeryim20533andthemechanismofinfluenceofgbutyrolactoneonthegrowthofstreptomycesbytheirnonenzymaticreactionbiosynthesis
AT dingzhongtao thestreptazolinandobscurolidetypemetabolitesfromsoilderivedstreptomycesalbonigeryim20533andthemechanismofinfluenceofgbutyrolactoneonthegrowthofstreptomycesbytheirnonenzymaticreactionbiosynthesis
AT zhaolixing thestreptazolinandobscurolidetypemetabolitesfromsoilderivedstreptomycesalbonigeryim20533andthemechanismofinfluenceofgbutyrolactoneonthegrowthofstreptomycesbytheirnonenzymaticreactionbiosynthesis
AT luona streptazolinandobscurolidetypemetabolitesfromsoilderivedstreptomycesalbonigeryim20533andthemechanismofinfluenceofgbutyrolactoneonthegrowthofstreptomycesbytheirnonenzymaticreactionbiosynthesis
AT yangyabin streptazolinandobscurolidetypemetabolitesfromsoilderivedstreptomycesalbonigeryim20533andthemechanismofinfluenceofgbutyrolactoneonthegrowthofstreptomycesbytheirnonenzymaticreactionbiosynthesis
AT yangxueqiong streptazolinandobscurolidetypemetabolitesfromsoilderivedstreptomycesalbonigeryim20533andthemechanismofinfluenceofgbutyrolactoneonthegrowthofstreptomycesbytheirnonenzymaticreactionbiosynthesis
AT miaocuiping streptazolinandobscurolidetypemetabolitesfromsoilderivedstreptomycesalbonigeryim20533andthemechanismofinfluenceofgbutyrolactoneonthegrowthofstreptomycesbytheirnonenzymaticreactionbiosynthesis
AT liyiqing streptazolinandobscurolidetypemetabolitesfromsoilderivedstreptomycesalbonigeryim20533andthemechanismofinfluenceofgbutyrolactoneonthegrowthofstreptomycesbytheirnonenzymaticreactionbiosynthesis
AT xulihua streptazolinandobscurolidetypemetabolitesfromsoilderivedstreptomycesalbonigeryim20533andthemechanismofinfluenceofgbutyrolactoneonthegrowthofstreptomycesbytheirnonenzymaticreactionbiosynthesis
AT dingzhongtao streptazolinandobscurolidetypemetabolitesfromsoilderivedstreptomycesalbonigeryim20533andthemechanismofinfluenceofgbutyrolactoneonthegrowthofstreptomycesbytheirnonenzymaticreactionbiosynthesis
AT zhaolixing streptazolinandobscurolidetypemetabolitesfromsoilderivedstreptomycesalbonigeryim20533andthemechanismofinfluenceofgbutyrolactoneonthegrowthofstreptomycesbytheirnonenzymaticreactionbiosynthesis