Isoquinoline Alkaloids as Protein Tyrosine Phosphatase Inhibitors from a Deep-Sea-Derived Fungus <em>Aspergillus puniceus</em>
Puniceusines A–N (<b>1</b>–<b>14</b>), 14 new isoquinoline alkaloids, were isolated from the extracts of a deep-sea-derived fungus, <i>Aspergillus puniceus</i> SCSIO z021. Their structures were elucidated by spectroscopic analyses. The absolute configuration of &l...
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| Format: | Article |
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MDPI AG
2022-01-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/20/1/78 |
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| author | Cheng-Mei Liu Fei-Hua Yao Xin-Hua Lu Xue-Xia Zhang Lian-Xiang Luo Xiao Liang Shu-Hua Qi |
| author_facet | Cheng-Mei Liu Fei-Hua Yao Xin-Hua Lu Xue-Xia Zhang Lian-Xiang Luo Xiao Liang Shu-Hua Qi |
| author_sort | Cheng-Mei Liu |
| collection | DOAJ |
| description | Puniceusines A–N (<b>1</b>–<b>14</b>), 14 new isoquinoline alkaloids, were isolated from the extracts of a deep-sea-derived fungus, <i>Aspergillus puniceus</i> SCSIO z021. Their structures were elucidated by spectroscopic analyses. The absolute configuration of <b>9</b> was determined by ECD calculations, and the structures of <b>6</b> and <b>12</b> were further confirmed by a single-crystal X-ray diffraction analysis. Compounds <b>3</b>–<b>5</b> and <b>8</b>–<b>13</b> unprecedentedly contained an isoquinolinyl, a polysubstituted benzyl or a pyronyl at position C-7 of isoquinoline nucleus. Compounds <b>3</b> and <b>4</b> showed selective inhibitory activity against protein tyrosine phosphatase CD45 with IC<sub>50</sub> values of 8.4 and 5.6 µM, respectively, <b>4</b> also had a moderate cytotoxicity towards human lung adenocarcinoma cell line H1975 with an IC<sub>50</sub> value of 11.0 µM, and <b>14</b>, which contained an active center, -C=N<sup>+</sup>, exhibited antibacterial activity. An analysis of the relationship between the structures, enzyme inhibitory activity and cytotoxicity of <b>1</b>–<b>14</b> revealed that the substituents at C-7 of the isoquinoline nucleus could greatly affect their bioactivity. |
| first_indexed | 2024-03-10T01:04:10Z |
| format | Article |
| id | doaj.art-11e2d4a877de48888abd5c4f800c6e6e |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T01:04:10Z |
| publishDate | 2022-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-11e2d4a877de48888abd5c4f800c6e6e2023-11-23T14:28:27ZengMDPI AGMarine Drugs1660-33972022-01-012017810.3390/md20010078Isoquinoline Alkaloids as Protein Tyrosine Phosphatase Inhibitors from a Deep-Sea-Derived Fungus <em>Aspergillus puniceus</em>Cheng-Mei Liu0Fei-Hua Yao1Xin-Hua Lu2Xue-Xia Zhang3Lian-Xiang Luo4Xiao Liang5Shu-Hua Qi6CAS Key Laboratory of Tropical Marine Bio-Resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, Innovation Academy of South China Sea Ecology and Environmental Engineering, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, ChinaCAS Key Laboratory of Tropical Marine Bio-Resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, Innovation Academy of South China Sea Ecology and Environmental Engineering, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, ChinaNew Drug Research & Development Co., Ltd., North China Pharmaceutical Group Corporation, Shijiazhuang 050015, ChinaNew Drug Research & Development Co., Ltd., North China Pharmaceutical Group Corporation, Shijiazhuang 050015, ChinaThe Marine Biomedical Research Institute, Guangdong Medical University, Zhanjiang 524023, ChinaCAS Key Laboratory of Tropical Marine Bio-Resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, Innovation Academy of South China Sea Ecology and Environmental Engineering, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, ChinaCAS Key Laboratory of Tropical Marine Bio-Resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, Innovation Academy of South China Sea Ecology and Environmental Engineering, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, ChinaPuniceusines A–N (<b>1</b>–<b>14</b>), 14 new isoquinoline alkaloids, were isolated from the extracts of a deep-sea-derived fungus, <i>Aspergillus puniceus</i> SCSIO z021. Their structures were elucidated by spectroscopic analyses. The absolute configuration of <b>9</b> was determined by ECD calculations, and the structures of <b>6</b> and <b>12</b> were further confirmed by a single-crystal X-ray diffraction analysis. Compounds <b>3</b>–<b>5</b> and <b>8</b>–<b>13</b> unprecedentedly contained an isoquinolinyl, a polysubstituted benzyl or a pyronyl at position C-7 of isoquinoline nucleus. Compounds <b>3</b> and <b>4</b> showed selective inhibitory activity against protein tyrosine phosphatase CD45 with IC<sub>50</sub> values of 8.4 and 5.6 µM, respectively, <b>4</b> also had a moderate cytotoxicity towards human lung adenocarcinoma cell line H1975 with an IC<sub>50</sub> value of 11.0 µM, and <b>14</b>, which contained an active center, -C=N<sup>+</sup>, exhibited antibacterial activity. An analysis of the relationship between the structures, enzyme inhibitory activity and cytotoxicity of <b>1</b>–<b>14</b> revealed that the substituents at C-7 of the isoquinoline nucleus could greatly affect their bioactivity.https://www.mdpi.com/1660-3397/20/1/78deep-sea-derived fungus<i>Aspergillus puniceus</i>isoquinoline alkaloidprotein tyrosine phosphatase inhibitorcytotoxicityantibacterial |
| spellingShingle | Cheng-Mei Liu Fei-Hua Yao Xin-Hua Lu Xue-Xia Zhang Lian-Xiang Luo Xiao Liang Shu-Hua Qi Isoquinoline Alkaloids as Protein Tyrosine Phosphatase Inhibitors from a Deep-Sea-Derived Fungus <em>Aspergillus puniceus</em> Marine Drugs deep-sea-derived fungus <i>Aspergillus puniceus</i> isoquinoline alkaloid protein tyrosine phosphatase inhibitor cytotoxicity antibacterial |
| title | Isoquinoline Alkaloids as Protein Tyrosine Phosphatase Inhibitors from a Deep-Sea-Derived Fungus <em>Aspergillus puniceus</em> |
| title_full | Isoquinoline Alkaloids as Protein Tyrosine Phosphatase Inhibitors from a Deep-Sea-Derived Fungus <em>Aspergillus puniceus</em> |
| title_fullStr | Isoquinoline Alkaloids as Protein Tyrosine Phosphatase Inhibitors from a Deep-Sea-Derived Fungus <em>Aspergillus puniceus</em> |
| title_full_unstemmed | Isoquinoline Alkaloids as Protein Tyrosine Phosphatase Inhibitors from a Deep-Sea-Derived Fungus <em>Aspergillus puniceus</em> |
| title_short | Isoquinoline Alkaloids as Protein Tyrosine Phosphatase Inhibitors from a Deep-Sea-Derived Fungus <em>Aspergillus puniceus</em> |
| title_sort | isoquinoline alkaloids as protein tyrosine phosphatase inhibitors from a deep sea derived fungus em aspergillus puniceus em |
| topic | deep-sea-derived fungus <i>Aspergillus puniceus</i> isoquinoline alkaloid protein tyrosine phosphatase inhibitor cytotoxicity antibacterial |
| url | https://www.mdpi.com/1660-3397/20/1/78 |
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