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Isolation, Structure Elucidation, and First Total Synthesis of Quinomycins K and L, Two New Octadepsipeptides from the Maowei Sea Mangrove-Derived Streptomyces sp. B475

Mangrove actinomycetia have been proven to be one of the promising sources for discovering novel bioactive natural products. Quinomycins K (1) and L (2), two rare quinomycin-type octadepsipeptides without intra-peptide disulfide or thioacetal bridges, were investigated from the Maowei Sea mangrove-d...

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Autores principales: Lu, Qinpei, Wu, Gang, Hao, Xiaomeng, Hu, Xinxin, Cai, Hao, Liu, Xiujun, You, Xuefu, Guo, Hongwei, Sun, Chenghang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10055584/
https://www.ncbi.nlm.nih.gov/pubmed/36976192
http://dx.doi.org/10.3390/md21030143
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author Lu, Qinpei
Wu, Gang
Hao, Xiaomeng
Hu, Xinxin
Cai, Hao
Liu, Xiujun
You, Xuefu
Guo, Hongwei
Sun, Chenghang
author_facet Lu, Qinpei
Wu, Gang
Hao, Xiaomeng
Hu, Xinxin
Cai, Hao
Liu, Xiujun
You, Xuefu
Guo, Hongwei
Sun, Chenghang
author_sort Lu, Qinpei
collection PubMed
description Mangrove actinomycetia have been proven to be one of the promising sources for discovering novel bioactive natural products. Quinomycins K (1) and L (2), two rare quinomycin-type octadepsipeptides without intra-peptide disulfide or thioacetal bridges, were investigated from the Maowei Sea mangrove-derived Streptomyces sp. B475. Their chemical structures, including the absolute configurations of their amino acids, were elucidated by a combination of NMR and tandem MS analysis, electronic circular dichroism (ECD) calculation, advanced Marfey’s method, and further unequivocally confirmed by the first total synthesis. The two compounds displayed no potent antibacterial activity against 37 bacterial pathogens and had no significant cytotoxic activity against H460 lung cancer cells.
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spelling pubmed-100555842023-03-30 Isolation, Structure Elucidation, and First Total Synthesis of Quinomycins K and L, Two New Octadepsipeptides from the Maowei Sea Mangrove-Derived Streptomyces sp. B475 Lu, Qinpei Wu, Gang Hao, Xiaomeng Hu, Xinxin Cai, Hao Liu, Xiujun You, Xuefu Guo, Hongwei Sun, Chenghang Mar Drugs Article Mangrove actinomycetia have been proven to be one of the promising sources for discovering novel bioactive natural products. Quinomycins K (1) and L (2), two rare quinomycin-type octadepsipeptides without intra-peptide disulfide or thioacetal bridges, were investigated from the Maowei Sea mangrove-derived Streptomyces sp. B475. Their chemical structures, including the absolute configurations of their amino acids, were elucidated by a combination of NMR and tandem MS analysis, electronic circular dichroism (ECD) calculation, advanced Marfey’s method, and further unequivocally confirmed by the first total synthesis. The two compounds displayed no potent antibacterial activity against 37 bacterial pathogens and had no significant cytotoxic activity against H460 lung cancer cells. MDPI 2023-02-23 /pmc/articles/PMC10055584/ /pubmed/36976192 http://dx.doi.org/10.3390/md21030143 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Lu, Qinpei
Wu, Gang
Hao, Xiaomeng
Hu, Xinxin
Cai, Hao
Liu, Xiujun
You, Xuefu
Guo, Hongwei
Sun, Chenghang
Isolation, Structure Elucidation, and First Total Synthesis of Quinomycins K and L, Two New Octadepsipeptides from the Maowei Sea Mangrove-Derived Streptomyces sp. B475
title Isolation, Structure Elucidation, and First Total Synthesis of Quinomycins K and L, Two New Octadepsipeptides from the Maowei Sea Mangrove-Derived Streptomyces sp. B475
title_full Isolation, Structure Elucidation, and First Total Synthesis of Quinomycins K and L, Two New Octadepsipeptides from the Maowei Sea Mangrove-Derived Streptomyces sp. B475
title_fullStr Isolation, Structure Elucidation, and First Total Synthesis of Quinomycins K and L, Two New Octadepsipeptides from the Maowei Sea Mangrove-Derived Streptomyces sp. B475
title_full_unstemmed Isolation, Structure Elucidation, and First Total Synthesis of Quinomycins K and L, Two New Octadepsipeptides from the Maowei Sea Mangrove-Derived Streptomyces sp. B475
title_short Isolation, Structure Elucidation, and First Total Synthesis of Quinomycins K and L, Two New Octadepsipeptides from the Maowei Sea Mangrove-Derived Streptomyces sp. B475
title_sort isolation, structure elucidation, and first total synthesis of quinomycins k and l, two new octadepsipeptides from the maowei sea mangrove-derived streptomyces sp. b475
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10055584/
https://www.ncbi.nlm.nih.gov/pubmed/36976192
http://dx.doi.org/10.3390/md21030143
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