A New Breviane Spiroditerpenoid from the Marine-Derived Fungus Penicillium sp. TJ403-1
Marine-derived fungi are a promising and untapped reservoir for discovering structurally interesting and pharmacologically active natural products. In our efforts to identify novel bioactive compounds from marine-derived fungi, four breviane spiroditerpenoids, including a new compound, brevione O (1...
| Main Authors: | , , , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2018-03-01
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| Series: | Marine Drugs |
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| Online Access: | http://www.mdpi.com/1660-3397/16/4/110 |
| _version_ | 1811184782503051264 |
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| author | Beiye Yang Weiguang Sun Jianping Wang Shuang Lin Xiao-Nian Li Hucheng Zhu Zengwei Luo Yongbo Xue Zhengxi Hu Yonghui Zhang |
| author_facet | Beiye Yang Weiguang Sun Jianping Wang Shuang Lin Xiao-Nian Li Hucheng Zhu Zengwei Luo Yongbo Xue Zhengxi Hu Yonghui Zhang |
| author_sort | Beiye Yang |
| collection | DOAJ |
| description | Marine-derived fungi are a promising and untapped reservoir for discovering structurally interesting and pharmacologically active natural products. In our efforts to identify novel bioactive compounds from marine-derived fungi, four breviane spiroditerpenoids, including a new compound, brevione O (1), and three known compounds breviones I (2), J (3), and H (4), together with a known diketopiperazine alkaloid brevicompanine G (5), were isolated and identified from an ethyl acetate extract of the fermented rice substrate of the coral-derived fungus Penicillium sp. TJ403-1. The absolute structure of 1 was elucidated by HRESIMS, one- and two-dimensional NMR spectroscopic data, and a comparison of its electronic circular dichroism (ECD) spectrum with the literature. Moreover, we confirmed the absolute configuration of 5 by single-crystal X-ray crystallography. All the isolated compounds were evaluated for isocitrate dehydrogenase 1 (IDH1) inhibitory activity and cytotoxicity, and compound 2 showed significant inhibitory activities against HL-60, A-549, and HEP3B tumor cell lines with IC50 values of 4.92 ± 0.65, 8.60 ± 1.36, and 5.50 ± 0.67 µM, respectively. |
| first_indexed | 2024-04-11T13:18:16Z |
| format | Article |
| id | doaj.art-9808640b3ccb4fc8b5b6978c3c8e38f8 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-11T13:18:16Z |
| publishDate | 2018-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-9808640b3ccb4fc8b5b6978c3c8e38f82022-12-22T04:22:18ZengMDPI AGMarine Drugs1660-33972018-03-0116411010.3390/md16040110md16040110A New Breviane Spiroditerpenoid from the Marine-Derived Fungus Penicillium sp. TJ403-1Beiye Yang0Weiguang Sun1Jianping Wang2Shuang Lin3Xiao-Nian Li4Hucheng Zhu5Zengwei Luo6Yongbo Xue7Zhengxi Hu8Yonghui Zhang9Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaState Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, ChinaHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaMarine-derived fungi are a promising and untapped reservoir for discovering structurally interesting and pharmacologically active natural products. In our efforts to identify novel bioactive compounds from marine-derived fungi, four breviane spiroditerpenoids, including a new compound, brevione O (1), and three known compounds breviones I (2), J (3), and H (4), together with a known diketopiperazine alkaloid brevicompanine G (5), were isolated and identified from an ethyl acetate extract of the fermented rice substrate of the coral-derived fungus Penicillium sp. TJ403-1. The absolute structure of 1 was elucidated by HRESIMS, one- and two-dimensional NMR spectroscopic data, and a comparison of its electronic circular dichroism (ECD) spectrum with the literature. Moreover, we confirmed the absolute configuration of 5 by single-crystal X-ray crystallography. All the isolated compounds were evaluated for isocitrate dehydrogenase 1 (IDH1) inhibitory activity and cytotoxicity, and compound 2 showed significant inhibitory activities against HL-60, A-549, and HEP3B tumor cell lines with IC50 values of 4.92 ± 0.65, 8.60 ± 1.36, and 5.50 ± 0.67 µM, respectively.http://www.mdpi.com/1660-3397/16/4/110marine-derived fungiPenicillium sp. TJ403-1breviane spiroditerpenoidIDH1 inhibitory activitycytotoxicity |
| spellingShingle | Beiye Yang Weiguang Sun Jianping Wang Shuang Lin Xiao-Nian Li Hucheng Zhu Zengwei Luo Yongbo Xue Zhengxi Hu Yonghui Zhang A New Breviane Spiroditerpenoid from the Marine-Derived Fungus Penicillium sp. TJ403-1 Marine Drugs marine-derived fungi Penicillium sp. TJ403-1 breviane spiroditerpenoid IDH1 inhibitory activity cytotoxicity |
| title | A New Breviane Spiroditerpenoid from the Marine-Derived Fungus Penicillium sp. TJ403-1 |
| title_full | A New Breviane Spiroditerpenoid from the Marine-Derived Fungus Penicillium sp. TJ403-1 |
| title_fullStr | A New Breviane Spiroditerpenoid from the Marine-Derived Fungus Penicillium sp. TJ403-1 |
| title_full_unstemmed | A New Breviane Spiroditerpenoid from the Marine-Derived Fungus Penicillium sp. TJ403-1 |
| title_short | A New Breviane Spiroditerpenoid from the Marine-Derived Fungus Penicillium sp. TJ403-1 |
| title_sort | new breviane spiroditerpenoid from the marine derived fungus penicillium sp tj403 1 |
| topic | marine-derived fungi Penicillium sp. TJ403-1 breviane spiroditerpenoid IDH1 inhibitory activity cytotoxicity |
| url | http://www.mdpi.com/1660-3397/16/4/110 |
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