Nitrogen-Containing Secondary Metabolites from a Deep-Sea Fungus <i>Aspergillus unguis</i> and Their Anti-Inflammatory Activity
<i>Aspergillus</i> is well-known as the second-largest contributor of fungal natural products. Based on NMR guided isolation, three nitrogen-containing secondary metabolites, including two new compounds, variotin B (<b>1</b>) and coniosulfide E (<b>2</b>), togethe...
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MDPI AG
2022-03-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/20/3/217 |
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| author | Cao Van Anh Yeo Dae Yoon Jong Soon Kang Hwa-Sun Lee Chang-Su Heo Hee Jae Shin |
| author_facet | Cao Van Anh Yeo Dae Yoon Jong Soon Kang Hwa-Sun Lee Chang-Su Heo Hee Jae Shin |
| author_sort | Cao Van Anh |
| collection | DOAJ |
| description | <i>Aspergillus</i> is well-known as the second-largest contributor of fungal natural products. Based on NMR guided isolation, three nitrogen-containing secondary metabolites, including two new compounds, variotin B (<b>1</b>) and coniosulfide E (<b>2</b>), together with a known compound, unguisin A (<b>3</b>), were isolated from the ethyl acetate (EtOAc) extract of the deep-sea fungus <i>Aspergillus unguis</i> IV17-109. The planar structures of <b>1</b> and <b>2</b> were elucidated by an extensive analysis of their spectroscopic data (HRESIMS, 1D and 2D NMR). The absolute configuration of <b>2</b> was determined by comparison of its optical rotation value with those of the synthesized analogs. Compound <b>2</b> is a rare, naturally occurring substance with an unusual cysteinol moiety. Furthermore, <b>1</b> showed moderate anti-inflammatory activity with an IC<sub>50</sub> value of 20.0 µM. These results revealed that <i>Aspergillus unguis</i> could produce structurally diverse nitrogenous secondary metabolites, which can be used for further studies to find anti-inflammatory leads. |
| first_indexed | 2024-03-09T13:30:06Z |
| format | Article |
| id | doaj.art-55364eea9e174624be16296a89b9ef26 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-09T13:30:06Z |
| publishDate | 2022-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-55364eea9e174624be16296a89b9ef262023-11-30T21:18:27ZengMDPI AGMarine Drugs1660-33972022-03-0120321710.3390/md20030217Nitrogen-Containing Secondary Metabolites from a Deep-Sea Fungus <i>Aspergillus unguis</i> and Their Anti-Inflammatory ActivityCao Van Anh0Yeo Dae Yoon1Jong Soon Kang2Hwa-Sun Lee3Chang-Su Heo4Hee Jae Shin5Marine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, 385 Haeyang-ro, Yeongdo-gu, Busan 49111, KoreaLaboratory Animal Resource Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanjiro, Cheongju 28116, KoreaLaboratory Animal Resource Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanjiro, Cheongju 28116, KoreaMarine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, 385 Haeyang-ro, Yeongdo-gu, Busan 49111, KoreaMarine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, 385 Haeyang-ro, Yeongdo-gu, Busan 49111, KoreaMarine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, 385 Haeyang-ro, Yeongdo-gu, Busan 49111, Korea<i>Aspergillus</i> is well-known as the second-largest contributor of fungal natural products. Based on NMR guided isolation, three nitrogen-containing secondary metabolites, including two new compounds, variotin B (<b>1</b>) and coniosulfide E (<b>2</b>), together with a known compound, unguisin A (<b>3</b>), were isolated from the ethyl acetate (EtOAc) extract of the deep-sea fungus <i>Aspergillus unguis</i> IV17-109. The planar structures of <b>1</b> and <b>2</b> were elucidated by an extensive analysis of their spectroscopic data (HRESIMS, 1D and 2D NMR). The absolute configuration of <b>2</b> was determined by comparison of its optical rotation value with those of the synthesized analogs. Compound <b>2</b> is a rare, naturally occurring substance with an unusual cysteinol moiety. Furthermore, <b>1</b> showed moderate anti-inflammatory activity with an IC<sub>50</sub> value of 20.0 µM. These results revealed that <i>Aspergillus unguis</i> could produce structurally diverse nitrogenous secondary metabolites, which can be used for further studies to find anti-inflammatory leads.https://www.mdpi.com/1660-3397/20/3/217deep-sea fungus<i>A. unguis</i>variotinconiosulfideanti-inflammatory |
| spellingShingle | Cao Van Anh Yeo Dae Yoon Jong Soon Kang Hwa-Sun Lee Chang-Su Heo Hee Jae Shin Nitrogen-Containing Secondary Metabolites from a Deep-Sea Fungus <i>Aspergillus unguis</i> and Their Anti-Inflammatory Activity Marine Drugs deep-sea fungus <i>A. unguis</i> variotin coniosulfide anti-inflammatory |
| title | Nitrogen-Containing Secondary Metabolites from a Deep-Sea Fungus <i>Aspergillus unguis</i> and Their Anti-Inflammatory Activity |
| title_full | Nitrogen-Containing Secondary Metabolites from a Deep-Sea Fungus <i>Aspergillus unguis</i> and Their Anti-Inflammatory Activity |
| title_fullStr | Nitrogen-Containing Secondary Metabolites from a Deep-Sea Fungus <i>Aspergillus unguis</i> and Their Anti-Inflammatory Activity |
| title_full_unstemmed | Nitrogen-Containing Secondary Metabolites from a Deep-Sea Fungus <i>Aspergillus unguis</i> and Their Anti-Inflammatory Activity |
| title_short | Nitrogen-Containing Secondary Metabolites from a Deep-Sea Fungus <i>Aspergillus unguis</i> and Their Anti-Inflammatory Activity |
| title_sort | nitrogen containing secondary metabolites from a deep sea fungus i aspergillus unguis i and their anti inflammatory activity |
| topic | deep-sea fungus <i>A. unguis</i> variotin coniosulfide anti-inflammatory |
| url | https://www.mdpi.com/1660-3397/20/3/217 |
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