Diketopiperazine Alkaloids and Bisabolene Sesquiterpenoids from <em>Aspergillus versicolor</em> AS-212, an Endozoic Fungus Associated with Deep-Sea Coral of Magellan Seamounts
Two new quinazolinone diketopiperazine alkaloids, including versicomide E (<b>2</b>) and cottoquinazoline H (<b>4</b>), together with ten known compounds (<b>1</b>, <b>3</b>, and <b>5</b>–<b>12</b>) were isolated and identified...
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MDPI AG
2023-05-01
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| Series: | Marine Drugs |
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| author | Yu-Liang Dong Xiao-Ming Li Xiao-Shan Shi Yi-Ran Wang Bin-Gui Wang Ling-Hong Meng |
| author_facet | Yu-Liang Dong Xiao-Ming Li Xiao-Shan Shi Yi-Ran Wang Bin-Gui Wang Ling-Hong Meng |
| author_sort | Yu-Liang Dong |
| collection | DOAJ |
| description | Two new quinazolinone diketopiperazine alkaloids, including versicomide E (<b>2</b>) and cottoquinazoline H (<b>4</b>), together with ten known compounds (<b>1</b>, <b>3</b>, and <b>5</b>–<b>12</b>) were isolated and identified from <i>Aspergillus versicolor</i> AS-212, an endozoic fungus associated with the deep-sea coral <i>Hemicorallium</i> cf. <i>imperiale</i>, which was collected from the Magellan Seamounts. Their chemical structures were determined by an extensive interpretation of the spectroscopic and X-ray crystallographic data as well as specific rotation calculation, ECD calculation, and comparison of their ECD spectra. The absolute configurations of (−)-isoversicomide A (<b>1</b>) and cottoquinazoline A (<b>3</b>) were not assigned in the literature reports and were solved in the present work by single-crystal X-ray diffraction analysis. In the antibacterial assays, compound <b>3</b> exhibited antibacterial activity against aquatic pathogenic bacteria <i>Aeromonas hydrophilia</i> with an MIC value of 18.6 μM, while compounds <b>4</b> and <b>8</b> exhibited inhibitory effects against <i>Vibrio harveyi</i> and <i>V. parahaemolyticus</i> with MIC values ranging from 9.0 to 18.1 μM. |
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| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-11T03:33:38Z |
| publishDate | 2023-05-01 |
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| series | Marine Drugs |
| spelling | doaj.art-8ccc43f1367d47129648dc94d64074ee2023-11-18T02:13:01ZengMDPI AGMarine Drugs1660-33972023-05-0121529310.3390/md21050293Diketopiperazine Alkaloids and Bisabolene Sesquiterpenoids from <em>Aspergillus versicolor</em> AS-212, an Endozoic Fungus Associated with Deep-Sea Coral of Magellan SeamountsYu-Liang Dong0Xiao-Ming Li1Xiao-Shan Shi2Yi-Ran Wang3Bin-Gui Wang4Ling-Hong Meng5CAS and Shandong Province Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, ChinaCAS and Shandong Province Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, ChinaCAS and Shandong Province Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, ChinaCAS and Shandong Province Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, ChinaCAS and Shandong Province Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, ChinaCAS and Shandong Province Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, ChinaTwo new quinazolinone diketopiperazine alkaloids, including versicomide E (<b>2</b>) and cottoquinazoline H (<b>4</b>), together with ten known compounds (<b>1</b>, <b>3</b>, and <b>5</b>–<b>12</b>) were isolated and identified from <i>Aspergillus versicolor</i> AS-212, an endozoic fungus associated with the deep-sea coral <i>Hemicorallium</i> cf. <i>imperiale</i>, which was collected from the Magellan Seamounts. Their chemical structures were determined by an extensive interpretation of the spectroscopic and X-ray crystallographic data as well as specific rotation calculation, ECD calculation, and comparison of their ECD spectra. The absolute configurations of (−)-isoversicomide A (<b>1</b>) and cottoquinazoline A (<b>3</b>) were not assigned in the literature reports and were solved in the present work by single-crystal X-ray diffraction analysis. In the antibacterial assays, compound <b>3</b> exhibited antibacterial activity against aquatic pathogenic bacteria <i>Aeromonas hydrophilia</i> with an MIC value of 18.6 μM, while compounds <b>4</b> and <b>8</b> exhibited inhibitory effects against <i>Vibrio harveyi</i> and <i>V. parahaemolyticus</i> with MIC values ranging from 9.0 to 18.1 μM.https://www.mdpi.com/1660-3397/21/5/293diketopiperazine<i>Aspergillus versicolor</i>deep-sea coralendophytic fungusantimicrobial activity |
| spellingShingle | Yu-Liang Dong Xiao-Ming Li Xiao-Shan Shi Yi-Ran Wang Bin-Gui Wang Ling-Hong Meng Diketopiperazine Alkaloids and Bisabolene Sesquiterpenoids from <em>Aspergillus versicolor</em> AS-212, an Endozoic Fungus Associated with Deep-Sea Coral of Magellan Seamounts Marine Drugs diketopiperazine <i>Aspergillus versicolor</i> deep-sea coral endophytic fungus antimicrobial activity |
| title | Diketopiperazine Alkaloids and Bisabolene Sesquiterpenoids from <em>Aspergillus versicolor</em> AS-212, an Endozoic Fungus Associated with Deep-Sea Coral of Magellan Seamounts |
| title_full | Diketopiperazine Alkaloids and Bisabolene Sesquiterpenoids from <em>Aspergillus versicolor</em> AS-212, an Endozoic Fungus Associated with Deep-Sea Coral of Magellan Seamounts |
| title_fullStr | Diketopiperazine Alkaloids and Bisabolene Sesquiterpenoids from <em>Aspergillus versicolor</em> AS-212, an Endozoic Fungus Associated with Deep-Sea Coral of Magellan Seamounts |
| title_full_unstemmed | Diketopiperazine Alkaloids and Bisabolene Sesquiterpenoids from <em>Aspergillus versicolor</em> AS-212, an Endozoic Fungus Associated with Deep-Sea Coral of Magellan Seamounts |
| title_short | Diketopiperazine Alkaloids and Bisabolene Sesquiterpenoids from <em>Aspergillus versicolor</em> AS-212, an Endozoic Fungus Associated with Deep-Sea Coral of Magellan Seamounts |
| title_sort | diketopiperazine alkaloids and bisabolene sesquiterpenoids from em aspergillus versicolor em as 212 an endozoic fungus associated with deep sea coral of magellan seamounts |
| topic | diketopiperazine <i>Aspergillus versicolor</i> deep-sea coral endophytic fungus antimicrobial activity |
| url | https://www.mdpi.com/1660-3397/21/5/293 |
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