Chemical Constituents and Anti-Angiogenic Principles from a Marine Algicolous <i>Penicillium sumatraense</i> SC29
In this study, a marine brown alga <i>Sargassum cristaefolium</i>-derived fungal strain, <i>Penicillium sumatraense</i> SC29, was isolated and identified. Column chromatography of the extracts from liquid fermented products of the fungal strain was carried out and led to the...
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MDPI AG
2022-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/24/8940 |
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| author | Hsiao-Yang Hsi Shih-Wei Wang Chia-Hsiung Cheng Ka-Lai Pang Jyh-Yih Leu Szu-Hsing Chang Yen-Tung Lee Yueh-Hsiung Kuo Chia-Ying Huang Tzong-Huei Lee |
| author_facet | Hsiao-Yang Hsi Shih-Wei Wang Chia-Hsiung Cheng Ka-Lai Pang Jyh-Yih Leu Szu-Hsing Chang Yen-Tung Lee Yueh-Hsiung Kuo Chia-Ying Huang Tzong-Huei Lee |
| author_sort | Hsiao-Yang Hsi |
| collection | DOAJ |
| description | In this study, a marine brown alga <i>Sargassum cristaefolium</i>-derived fungal strain, <i>Penicillium sumatraense</i> SC29, was isolated and identified. Column chromatography of the extracts from liquid fermented products of the fungal strain was carried out and led to the isolation of six compounds. Their structures were elucidated by spectroscopic analysis and supported by single-crystal X-ray diffraction as four previously undescribed (<i>R</i>)-3-hydroxybutyric acid and glycolic acid derivatives, namely penisterines A (<b>1</b>) and C–E (<b>3</b>–<b>5</b>) and penisterine A methyl ether (<b>2</b>), isolated for the first time from natural resources, along with (<i>R</i>)-3-hydroxybutyric acid (<b>6</b>). Of these compounds identified, penisterine E (<b>5</b>) was a unique 6/6/6-tricyclic ether with an acetal and two hemiketal functionalities. All the isolates were subjected to in vitro anti-angiogenic assays using a human endothelial progenitor cell (EPCs) platform. Among these, penisterine D (<b>4</b>) inhibited EPC growth, migration, and tube formation without any cytotoxic effect. Further, in in vivo bioassays, the percentages of angiogenesis of compound <b>3</b> on <i>Tg</i> (<i>fli1</i>:EGFP) transgenic zebrafish were 54% and 37% as the treated concentration increased from 10.2 to 20.4 µg/mL, respectively, and the percentages of angiogenesis of compound <b>4</b> were 52% and 41% as the treated concentration increased from 8.6 to 17.2 µg/mL, respectively. The anti-angiogenic activity of penisterine D (<b>4</b>) makes it an attractive candidate for further preclinical investigation. |
| first_indexed | 2024-03-09T16:02:34Z |
| format | Article |
| id | doaj.art-bb15253e43f345fda57f35527fe274c5 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T16:02:34Z |
| publishDate | 2022-12-01 |
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| spelling | doaj.art-bb15253e43f345fda57f35527fe274c52023-11-24T17:00:00ZengMDPI AGMolecules1420-30492022-12-012724894010.3390/molecules27248940Chemical Constituents and Anti-Angiogenic Principles from a Marine Algicolous <i>Penicillium sumatraense</i> SC29Hsiao-Yang Hsi0Shih-Wei Wang1Chia-Hsiung Cheng2Ka-Lai Pang3Jyh-Yih Leu4Szu-Hsing Chang5Yen-Tung Lee6Yueh-Hsiung Kuo7Chia-Ying Huang8Tzong-Huei Lee9Institute of Fisheries Science, National Taiwan University, Taipei 10617, TaiwanInstitute of Biomedical Sciences, MacKay Medical College, New Taipei City 252, TaiwanDepartment of Biochemistry and Molecular Cell Biology, School of Medicine, College of Medicine, Taipei Medical University, Taipei 11031, TaiwanInstitute of Marine Biology and Centre of Excellence for the Oceans, National Taiwan Ocean University, Keelung 202301, TaiwanThe Department of Life Science, Fu Jen Catholic University, New Taipei City 242304, TaiwanGraduate institute of Applied Science and Engineering, College of Science and Engineering, Fu Jen Catholic University, New Taipei City 242304, TaiwanDepartment of Chinese Medicine, MacKay Memorial Hospital, Taipei 10449, TaiwanDepartment of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 40447, TaiwanInstitute of Biomedical Sciences, MacKay Medical College, New Taipei City 252, TaiwanInstitute of Fisheries Science, National Taiwan University, Taipei 10617, TaiwanIn this study, a marine brown alga <i>Sargassum cristaefolium</i>-derived fungal strain, <i>Penicillium sumatraense</i> SC29, was isolated and identified. Column chromatography of the extracts from liquid fermented products of the fungal strain was carried out and led to the isolation of six compounds. Their structures were elucidated by spectroscopic analysis and supported by single-crystal X-ray diffraction as four previously undescribed (<i>R</i>)-3-hydroxybutyric acid and glycolic acid derivatives, namely penisterines A (<b>1</b>) and C–E (<b>3</b>–<b>5</b>) and penisterine A methyl ether (<b>2</b>), isolated for the first time from natural resources, along with (<i>R</i>)-3-hydroxybutyric acid (<b>6</b>). Of these compounds identified, penisterine E (<b>5</b>) was a unique 6/6/6-tricyclic ether with an acetal and two hemiketal functionalities. All the isolates were subjected to in vitro anti-angiogenic assays using a human endothelial progenitor cell (EPCs) platform. Among these, penisterine D (<b>4</b>) inhibited EPC growth, migration, and tube formation without any cytotoxic effect. Further, in in vivo bioassays, the percentages of angiogenesis of compound <b>3</b> on <i>Tg</i> (<i>fli1</i>:EGFP) transgenic zebrafish were 54% and 37% as the treated concentration increased from 10.2 to 20.4 µg/mL, respectively, and the percentages of angiogenesis of compound <b>4</b> were 52% and 41% as the treated concentration increased from 8.6 to 17.2 µg/mL, respectively. The anti-angiogenic activity of penisterine D (<b>4</b>) makes it an attractive candidate for further preclinical investigation.https://www.mdpi.com/1420-3049/27/24/8940<i>Penicillium sumatraense</i>penisterineanti-angiogenesisendothelial progenitor cellszebrafish |
| spellingShingle | Hsiao-Yang Hsi Shih-Wei Wang Chia-Hsiung Cheng Ka-Lai Pang Jyh-Yih Leu Szu-Hsing Chang Yen-Tung Lee Yueh-Hsiung Kuo Chia-Ying Huang Tzong-Huei Lee Chemical Constituents and Anti-Angiogenic Principles from a Marine Algicolous <i>Penicillium sumatraense</i> SC29 Molecules <i>Penicillium sumatraense</i> penisterine anti-angiogenesis endothelial progenitor cells zebrafish |
| title | Chemical Constituents and Anti-Angiogenic Principles from a Marine Algicolous <i>Penicillium sumatraense</i> SC29 |
| title_full | Chemical Constituents and Anti-Angiogenic Principles from a Marine Algicolous <i>Penicillium sumatraense</i> SC29 |
| title_fullStr | Chemical Constituents and Anti-Angiogenic Principles from a Marine Algicolous <i>Penicillium sumatraense</i> SC29 |
| title_full_unstemmed | Chemical Constituents and Anti-Angiogenic Principles from a Marine Algicolous <i>Penicillium sumatraense</i> SC29 |
| title_short | Chemical Constituents and Anti-Angiogenic Principles from a Marine Algicolous <i>Penicillium sumatraense</i> SC29 |
| title_sort | chemical constituents and anti angiogenic principles from a marine algicolous i penicillium sumatraense i sc29 |
| topic | <i>Penicillium sumatraense</i> penisterine anti-angiogenesis endothelial progenitor cells zebrafish |
| url | https://www.mdpi.com/1420-3049/27/24/8940 |
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