Isolation, Structure Elucidation, and First Total Synthesis of Quinomycins K and L, Two New Octadepsipeptides from the Maowei Sea Mangrove-Derived <i>Streptomyces</i> sp. B475
Mangrove actinomycetia have been proven to be one of the promising sources for discovering novel bioactive natural products. Quinomycins K (<b>1</b>) and L (<b>2</b>), two rare quinomycin-type octadepsipeptides without intra-peptide disulfide or thioacetal bridges, were inves...
| Main Authors: | , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-02-01
|
| Series: | Marine Drugs |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1660-3397/21/3/143 |
| _version_ | 1797610527946440704 |
|---|---|
| author | Qinpei Lu Gang Wu Xiaomeng Hao Xinxin Hu Hao Cai Xiujun Liu Xuefu You Hongwei Guo Chenghang Sun |
| author_facet | Qinpei Lu Gang Wu Xiaomeng Hao Xinxin Hu Hao Cai Xiujun Liu Xuefu You Hongwei Guo Chenghang Sun |
| author_sort | Qinpei Lu |
| collection | DOAJ |
| description | Mangrove actinomycetia have been proven to be one of the promising sources for discovering novel bioactive natural products. Quinomycins K (<b>1</b>) and L (<b>2</b>), two rare quinomycin-type octadepsipeptides without intra-peptide disulfide or thioacetal bridges, were investigated from the Maowei Sea mangrove-derived <i>Streptomyces</i> 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. |
| first_indexed | 2024-03-11T06:16:30Z |
| format | Article |
| id | doaj.art-9eee7f428bbd44bd96dc171b583da317 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-11T06:16:30Z |
| publishDate | 2023-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-9eee7f428bbd44bd96dc171b583da3172023-11-17T12:17:08ZengMDPI AGMarine Drugs1660-33972023-02-0121314310.3390/md21030143Isolation, Structure Elucidation, and First Total Synthesis of Quinomycins K and L, Two New Octadepsipeptides from the Maowei Sea Mangrove-Derived <i>Streptomyces</i> sp. B475Qinpei Lu0Gang Wu1Xiaomeng Hao2Xinxin Hu3Hao Cai4Xiujun Liu5Xuefu You6Hongwei Guo7Chenghang Sun8Guangxi Key Laboratory of Bioactive Molecules Research and Evaluation, Pharmaceutical College, Guangxi Medical University, Nanning 530021, ChinaDepartment of Microbial Chemistry, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, ChinaDepartment of Microbial Chemistry, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, ChinaBeijing Key Laboratory of Antimicrobial Agents, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, ChinaDepartment of Oncology, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, ChinaDepartment of Oncology, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, ChinaBeijing Key Laboratory of Antimicrobial Agents, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, ChinaGuangxi Key Laboratory of Bioactive Molecules Research and Evaluation, Pharmaceutical College, Guangxi Medical University, Nanning 530021, ChinaDepartment of Microbial Chemistry, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, ChinaMangrove actinomycetia have been proven to be one of the promising sources for discovering novel bioactive natural products. Quinomycins K (<b>1</b>) and L (<b>2</b>), two rare quinomycin-type octadepsipeptides without intra-peptide disulfide or thioacetal bridges, were investigated from the Maowei Sea mangrove-derived <i>Streptomyces</i> 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.https://www.mdpi.com/1660-3397/21/3/143Maowei Sea<i>Streptomyces</i> sp.quinomycinoctadepsipeptidetotal synthesis |
| spellingShingle | Qinpei Lu Gang Wu Xiaomeng Hao Xinxin Hu Hao Cai Xiujun Liu Xuefu You Hongwei Guo Chenghang Sun Isolation, Structure Elucidation, and First Total Synthesis of Quinomycins K and L, Two New Octadepsipeptides from the Maowei Sea Mangrove-Derived <i>Streptomyces</i> sp. B475 Marine Drugs Maowei Sea <i>Streptomyces</i> sp. quinomycin octadepsipeptide total synthesis |
| title | Isolation, Structure Elucidation, and First Total Synthesis of Quinomycins K and L, Two New Octadepsipeptides from the Maowei Sea Mangrove-Derived <i>Streptomyces</i> 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 <i>Streptomyces</i> 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 <i>Streptomyces</i> 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 <i>Streptomyces</i> 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 <i>Streptomyces</i> 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 i streptomyces i sp b475 |
| topic | Maowei Sea <i>Streptomyces</i> sp. quinomycin octadepsipeptide total synthesis |
| url | https://www.mdpi.com/1660-3397/21/3/143 |
| work_keys_str_mv | AT qinpeilu isolationstructureelucidationandfirsttotalsynthesisofquinomycinskandltwonewoctadepsipeptidesfromthemaoweiseamangrovederivedistreptomycesispb475 AT gangwu isolationstructureelucidationandfirsttotalsynthesisofquinomycinskandltwonewoctadepsipeptidesfromthemaoweiseamangrovederivedistreptomycesispb475 AT xiaomenghao isolationstructureelucidationandfirsttotalsynthesisofquinomycinskandltwonewoctadepsipeptidesfromthemaoweiseamangrovederivedistreptomycesispb475 AT xinxinhu isolationstructureelucidationandfirsttotalsynthesisofquinomycinskandltwonewoctadepsipeptidesfromthemaoweiseamangrovederivedistreptomycesispb475 AT haocai isolationstructureelucidationandfirsttotalsynthesisofquinomycinskandltwonewoctadepsipeptidesfromthemaoweiseamangrovederivedistreptomycesispb475 AT xiujunliu isolationstructureelucidationandfirsttotalsynthesisofquinomycinskandltwonewoctadepsipeptidesfromthemaoweiseamangrovederivedistreptomycesispb475 AT xuefuyou isolationstructureelucidationandfirsttotalsynthesisofquinomycinskandltwonewoctadepsipeptidesfromthemaoweiseamangrovederivedistreptomycesispb475 AT hongweiguo isolationstructureelucidationandfirsttotalsynthesisofquinomycinskandltwonewoctadepsipeptidesfromthemaoweiseamangrovederivedistreptomycesispb475 AT chenghangsun isolationstructureelucidationandfirsttotalsynthesisofquinomycinskandltwonewoctadepsipeptidesfromthemaoweiseamangrovederivedistreptomycesispb475 |