New Pyrroline Isolated from Antarctic Krill-Derived Actinomycetes <i>Nocardiopsis</i> sp. LX-1 Combining with Molecular Networking
Antarctic krill (<i>Euphausia superba</i>) of the <i>Euphausiidae</i> family comprise one of the largest biomasses in the world and play a key role in the Antarctic marine ecosystem. However, the study of <i>E. superba</i>-derived microbes and their secondary meta...
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MDPI AG
2023-02-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/21/2/127 |
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| author | Ting Shi Yan-Jing Li Ze-Min Wang Yi-Fei Wang Bo Wang Da-Yong Shi |
| author_facet | Ting Shi Yan-Jing Li Ze-Min Wang Yi-Fei Wang Bo Wang Da-Yong Shi |
| author_sort | Ting Shi |
| collection | DOAJ |
| description | Antarctic krill (<i>Euphausia superba</i>) of the <i>Euphausiidae</i> family comprise one of the largest biomasses in the world and play a key role in the Antarctic marine ecosystem. However, the study of <i>E. superba</i>-derived microbes and their secondary metabolites has been limited. Chemical investigation of the secondary metabolites of the actinomycetes <i>Nocardiopsis</i> sp. LX-1 (in the family of <i>Nocardiopsaceae</i>), isolated from <i>E. superba</i>, combined with molecular networking, led to the identification of 16 compounds <b>a</b>–<b>p</b> (purple nodes in the molecular network) and the isolation of one new pyrroline, nocarpyrroline A (<b>1</b>), along with 11 known compounds <b>2</b>–<b>12</b>. The structure of the new compound <b>1</b> was elucidated by extensive spectroscopic investigation. Compound <b>2</b> exhibited broad-spectrum antibacterial activities against <i>A. hydrophila</i>, <i>D. chrysanthemi</i>, <i>C. terrigena</i>, <i>X. citri pv. malvacearum</i> and antifungal activity against <i>C. albicans</i> in a conventional broth dilution assay. The positive control was ciprofloxacin with the MIC values of <0.024 µM, 0.39 µM, 0.39 µM, 0.39 µM, and 0.20 µM, respectively. Compound <b>1</b> and compounds <b>7</b>, <b>10</b>, and <b>11</b> displayed antifungal activities against <i>F. fujikuroi</i> and <i>D. citri</i>, respectively, in modified agar diffusion test. Prochloraz was used as positive control and showed the inhibition zone radius of 17 mm and 15 mm against <i>F. fujikuroi</i> and <i>D. citri</i>, respectively. All the annotated compounds <b>a</b>–<b>p</b> by molecular networking were first discovered from the genus <i>Nocardiopsis</i>. Nocarpyrroline A (<b>1</b>) features an unprecedented 4,5-dihydro-pyrrole-2-carbonitrile substructure, and it is the first pyrroline isolated from the genus <i>Nocardiopsis</i>. This study further demonstrated the guiding significance of molecular networking in the research of microbial secondary metabolites. |
| first_indexed | 2024-03-11T08:30:13Z |
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| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-11T08:30:13Z |
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| spelling | doaj.art-3e6b9328d611433ab82447f17c834ab32023-11-16T21:48:10ZengMDPI AGMarine Drugs1660-33972023-02-0121212710.3390/md21020127New Pyrroline Isolated from Antarctic Krill-Derived Actinomycetes <i>Nocardiopsis</i> sp. LX-1 Combining with Molecular NetworkingTing Shi0Yan-Jing Li1Ze-Min Wang2Yi-Fei Wang3Bo Wang4Da-Yong Shi5College of Chemical and Biological Engineering, Shandong University of Science and Technology, Qingdao 266590, ChinaCollege of Chemical and Biological Engineering, Shandong University of Science and Technology, Qingdao 266590, ChinaState Key Laboratory of Microbial Technology, Institute of Microbial Technology, Shandong University, Qingdao 266237, ChinaCollege of Chemical and Biological Engineering, Shandong University of Science and Technology, Qingdao 266590, ChinaCollege of Chemical and Biological Engineering, Shandong University of Science and Technology, Qingdao 266590, ChinaState Key Laboratory of Microbial Technology, Institute of Microbial Technology, Shandong University, Qingdao 266237, ChinaAntarctic krill (<i>Euphausia superba</i>) of the <i>Euphausiidae</i> family comprise one of the largest biomasses in the world and play a key role in the Antarctic marine ecosystem. However, the study of <i>E. superba</i>-derived microbes and their secondary metabolites has been limited. Chemical investigation of the secondary metabolites of the actinomycetes <i>Nocardiopsis</i> sp. LX-1 (in the family of <i>Nocardiopsaceae</i>), isolated from <i>E. superba</i>, combined with molecular networking, led to the identification of 16 compounds <b>a</b>–<b>p</b> (purple nodes in the molecular network) and the isolation of one new pyrroline, nocarpyrroline A (<b>1</b>), along with 11 known compounds <b>2</b>–<b>12</b>. The structure of the new compound <b>1</b> was elucidated by extensive spectroscopic investigation. Compound <b>2</b> exhibited broad-spectrum antibacterial activities against <i>A. hydrophila</i>, <i>D. chrysanthemi</i>, <i>C. terrigena</i>, <i>X. citri pv. malvacearum</i> and antifungal activity against <i>C. albicans</i> in a conventional broth dilution assay. The positive control was ciprofloxacin with the MIC values of <0.024 µM, 0.39 µM, 0.39 µM, 0.39 µM, and 0.20 µM, respectively. Compound <b>1</b> and compounds <b>7</b>, <b>10</b>, and <b>11</b> displayed antifungal activities against <i>F. fujikuroi</i> and <i>D. citri</i>, respectively, in modified agar diffusion test. Prochloraz was used as positive control and showed the inhibition zone radius of 17 mm and 15 mm against <i>F. fujikuroi</i> and <i>D. citri</i>, respectively. All the annotated compounds <b>a</b>–<b>p</b> by molecular networking were first discovered from the genus <i>Nocardiopsis</i>. Nocarpyrroline A (<b>1</b>) features an unprecedented 4,5-dihydro-pyrrole-2-carbonitrile substructure, and it is the first pyrroline isolated from the genus <i>Nocardiopsis</i>. This study further demonstrated the guiding significance of molecular networking in the research of microbial secondary metabolites.https://www.mdpi.com/1660-3397/21/2/127molecular networkingAntarctic krill<i>Nocardiopsis</i> sp. LX-1pyrrolinenocarpyrroline Aantimicrobial activity |
| spellingShingle | Ting Shi Yan-Jing Li Ze-Min Wang Yi-Fei Wang Bo Wang Da-Yong Shi New Pyrroline Isolated from Antarctic Krill-Derived Actinomycetes <i>Nocardiopsis</i> sp. LX-1 Combining with Molecular Networking Marine Drugs molecular networking Antarctic krill <i>Nocardiopsis</i> sp. LX-1 pyrroline nocarpyrroline A antimicrobial activity |
| title | New Pyrroline Isolated from Antarctic Krill-Derived Actinomycetes <i>Nocardiopsis</i> sp. LX-1 Combining with Molecular Networking |
| title_full | New Pyrroline Isolated from Antarctic Krill-Derived Actinomycetes <i>Nocardiopsis</i> sp. LX-1 Combining with Molecular Networking |
| title_fullStr | New Pyrroline Isolated from Antarctic Krill-Derived Actinomycetes <i>Nocardiopsis</i> sp. LX-1 Combining with Molecular Networking |
| title_full_unstemmed | New Pyrroline Isolated from Antarctic Krill-Derived Actinomycetes <i>Nocardiopsis</i> sp. LX-1 Combining with Molecular Networking |
| title_short | New Pyrroline Isolated from Antarctic Krill-Derived Actinomycetes <i>Nocardiopsis</i> sp. LX-1 Combining with Molecular Networking |
| title_sort | new pyrroline isolated from antarctic krill derived actinomycetes i nocardiopsis i sp lx 1 combining with molecular networking |
| topic | molecular networking Antarctic krill <i>Nocardiopsis</i> sp. LX-1 pyrroline nocarpyrroline A antimicrobial activity |
| url | https://www.mdpi.com/1660-3397/21/2/127 |
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