{"title":"利用基于 LC-MS/MS 的分子网络,有针对性地分离抗结核环肽和一种不寻常的含吡咯吲哚啉的新类似物 Asperpyrroindotide A。","authors":"Yi-Qian Han, Qun Zhang, Wei-Feng Xu, Yang Hai, Rong Chao, Cui-Fang Wang, Xue-Mei Hou, Mei-Yan Wei, Yu-Cheng Gu, Chang-Yun Wang, Chang-Lun Shao","doi":"10.1007/s42995-022-00157-8","DOIUrl":null,"url":null,"abstract":"<p><p>Further insights on the secondary metabolites of a soft coral-derived fungus <i>Aspergillus versicolor</i> under the guidance of MS/MS-based molecular networking led to the isolation of seven known cycloheptapeptides, namely, asperversiamides A-C (<b>1</b>-<b>3</b>) and asperheptatides A-D (<b>4</b>-<b>7</b>) and an unusual pyrroloindoline-containing new cycloheptapeptide, asperpyrroindotide A (<b>8</b>). The structure of <b>8</b> was elucidated by comprehensive spectroscopic data analysis, and its absolute configuration was determined by advanced Marfey's method. The semisynthetic transformation of <b>1</b> into <b>8</b> was successfully achieved and the reaction conditions were optimized. Additionally, a series of new derivatives (<b>10</b>-<b>19</b>) of asperversiamide A (<b>1</b>) was semi-synthesized and their anti-tubercular activities were evaluated against <i>Mycobacterium tuberculosis</i> H37Ra. The preliminary structure-activity relationships revealed that the serine hydroxy groups and the tryptophan residue are important to the activity.</p><p><strong>Supplementary information: </strong>The online version contains supplementary material available at 10.1007/s42995-022-00157-8.</p>","PeriodicalId":53218,"journal":{"name":"Marine Life Science & Technology","volume":"5 1","pages":"85-93"},"PeriodicalIF":5.8000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9854410/pdf/","citationCount":"0","resultStr":"{\"title\":\"Targeted isolation of antitubercular cycloheptapeptides and an unusual pyrroloindoline-containing new analog, asperpyrroindotide A, using LC-MS/MS-based molecular networking.\",\"authors\":\"Yi-Qian Han, Qun Zhang, Wei-Feng Xu, Yang Hai, Rong Chao, Cui-Fang Wang, Xue-Mei Hou, Mei-Yan Wei, Yu-Cheng Gu, Chang-Yun Wang, Chang-Lun Shao\",\"doi\":\"10.1007/s42995-022-00157-8\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Further insights on the secondary metabolites of a soft coral-derived fungus <i>Aspergillus versicolor</i> under the guidance of MS/MS-based molecular networking led to the isolation of seven known cycloheptapeptides, namely, asperversiamides A-C (<b>1</b>-<b>3</b>) and asperheptatides A-D (<b>4</b>-<b>7</b>) and an unusual pyrroloindoline-containing new cycloheptapeptide, asperpyrroindotide A (<b>8</b>). The structure of <b>8</b> was elucidated by comprehensive spectroscopic data analysis, and its absolute configuration was determined by advanced Marfey's method. The semisynthetic transformation of <b>1</b> into <b>8</b> was successfully achieved and the reaction conditions were optimized. Additionally, a series of new derivatives (<b>10</b>-<b>19</b>) of asperversiamide A (<b>1</b>) was semi-synthesized and their anti-tubercular activities were evaluated against <i>Mycobacterium tuberculosis</i> H37Ra. The preliminary structure-activity relationships revealed that the serine hydroxy groups and the tryptophan residue are important to the activity.</p><p><strong>Supplementary information: </strong>The online version contains supplementary material available at 10.1007/s42995-022-00157-8.</p>\",\"PeriodicalId\":53218,\"journal\":{\"name\":\"Marine Life Science & Technology\",\"volume\":\"5 1\",\"pages\":\"85-93\"},\"PeriodicalIF\":5.8000,\"publicationDate\":\"2023-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9854410/pdf/\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Marine Life Science & Technology\",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://doi.org/10.1007/s42995-022-00157-8\",\"RegionNum\":2,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2023/1/20 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q1\",\"JCRName\":\"MARINE & FRESHWATER BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Marine Life Science & Technology","FirstCategoryId":"99","ListUrlMain":"https://doi.org/10.1007/s42995-022-00157-8","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2023/1/20 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"MARINE & FRESHWATER BIOLOGY","Score":null,"Total":0}
Targeted isolation of antitubercular cycloheptapeptides and an unusual pyrroloindoline-containing new analog, asperpyrroindotide A, using LC-MS/MS-based molecular networking.
Further insights on the secondary metabolites of a soft coral-derived fungus Aspergillus versicolor under the guidance of MS/MS-based molecular networking led to the isolation of seven known cycloheptapeptides, namely, asperversiamides A-C (1-3) and asperheptatides A-D (4-7) and an unusual pyrroloindoline-containing new cycloheptapeptide, asperpyrroindotide A (8). The structure of 8 was elucidated by comprehensive spectroscopic data analysis, and its absolute configuration was determined by advanced Marfey's method. The semisynthetic transformation of 1 into 8 was successfully achieved and the reaction conditions were optimized. Additionally, a series of new derivatives (10-19) of asperversiamide A (1) was semi-synthesized and their anti-tubercular activities were evaluated against Mycobacterium tuberculosis H37Ra. The preliminary structure-activity relationships revealed that the serine hydroxy groups and the tryptophan residue are important to the activity.
Supplementary information: The online version contains supplementary material available at 10.1007/s42995-022-00157-8.
期刊介绍:
Marine Life Science & Technology (MLST), established in 2019, is dedicated to publishing original research papers that unveil new discoveries and theories spanning a wide spectrum of life sciences and technologies. This includes fundamental biology, fisheries science and technology, medicinal bioresources, food science, biotechnology, ecology, and environmental biology, with a particular focus on marine habitats.
The journal is committed to nurturing synergistic interactions among these diverse disciplines, striving to advance multidisciplinary approaches within the scientific field. It caters to a readership comprising biological scientists, aquaculture researchers, marine technologists, biological oceanographers, and ecologists.