Euchrestifolines A–O, fifteen novel carbazole alkaloids with potent anti-ferroptotic activity from Murraya euchrestifolia
Abstract Fifteen novel carbazole alkaloids, euchrestifolines A–O (1–15), were obtained from Murraya euchrestifolia. Their structures were elucidated by spectroscopic analysis, Mosher’s ester, calculated ECD, and transition metal complex ECD methods. Notably, euchrestifolines A–C (1–3) are the first...
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2025-01-01
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| Series: | Natural Products and Bioprospecting |
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| Online Access: | https://doi.org/10.1007/s13659-024-00483-7 |
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| author | Yue-Mei Chen Nan-Kai Cao Si-Si Zhu Meng Ding Hai-Zhen Liang Ming-Bo Zhao Ke-Wu Zeng Peng-Fei Tu Yong Jiang |
| author_facet | Yue-Mei Chen Nan-Kai Cao Si-Si Zhu Meng Ding Hai-Zhen Liang Ming-Bo Zhao Ke-Wu Zeng Peng-Fei Tu Yong Jiang |
| author_sort | Yue-Mei Chen |
| collection | DOAJ |
| description | Abstract Fifteen novel carbazole alkaloids, euchrestifolines A–O (1–15), were obtained from Murraya euchrestifolia. Their structures were elucidated by spectroscopic analysis, Mosher’s ester, calculated ECD, and transition metal complex ECD methods. Notably, euchrestifolines A–C (1–3) are the first naturally occurring pyrrolidone carbazoles to be identified, while euchrestifolines D–F (4–6) represent rare carbazole alkaloids containing a phenylpropanyl moiety; euchrestifoline G (7) features a unique benzopyranocarbazole skeleton. More importantly, these compounds exhibited significant anti-ferroptotic activity, along with inhibitory effects of nitric oxide (NO) production and notable cytotoxicity. This study marks the first disclosure of carbazole's inhibitory effects against ferroptosis, and the EC50 values of some carbazoles ranging from 0.04 to 1 μM, substantially lower than the positive control, ferrostatin-1. In sum, this research not only enhances our understanding of carbazole alkaloids but also opens new avenues for the discovery of ferroptosis-related leading compounds. Graphical abstract |
| format | Article |
| id | doaj-art-2161ef7f4d674e3eac0994e52cc43d40 |
| institution | Kabale University |
| issn | 2192-2195 2192-2209 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | SpringerOpen |
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| series | Natural Products and Bioprospecting |
| spelling | doaj-art-2161ef7f4d674e3eac0994e52cc43d402025-01-05T12:49:59ZengSpringerOpenNatural Products and Bioprospecting2192-21952192-22092025-01-0115111610.1007/s13659-024-00483-7Euchrestifolines A–O, fifteen novel carbazole alkaloids with potent anti-ferroptotic activity from Murraya euchrestifoliaYue-Mei Chen0Nan-Kai Cao1Si-Si Zhu2Meng Ding3Hai-Zhen Liang4Ming-Bo Zhao5Ke-Wu Zeng6Peng-Fei Tu7Yong Jiang8State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking UniversityState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking UniversityState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking UniversityState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking UniversityState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking UniversityState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking UniversityState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking UniversityState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking UniversityState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking UniversityAbstract Fifteen novel carbazole alkaloids, euchrestifolines A–O (1–15), were obtained from Murraya euchrestifolia. Their structures were elucidated by spectroscopic analysis, Mosher’s ester, calculated ECD, and transition metal complex ECD methods. Notably, euchrestifolines A–C (1–3) are the first naturally occurring pyrrolidone carbazoles to be identified, while euchrestifolines D–F (4–6) represent rare carbazole alkaloids containing a phenylpropanyl moiety; euchrestifoline G (7) features a unique benzopyranocarbazole skeleton. More importantly, these compounds exhibited significant anti-ferroptotic activity, along with inhibitory effects of nitric oxide (NO) production and notable cytotoxicity. This study marks the first disclosure of carbazole's inhibitory effects against ferroptosis, and the EC50 values of some carbazoles ranging from 0.04 to 1 μM, substantially lower than the positive control, ferrostatin-1. In sum, this research not only enhances our understanding of carbazole alkaloids but also opens new avenues for the discovery of ferroptosis-related leading compounds. Graphical abstracthttps://doi.org/10.1007/s13659-024-00483-7Murraya euchrestifoliaCarbazoleBenzopyranocarbazoleAnti-ferroptosisNO inhibitionCytotoxicity |
| spellingShingle | Yue-Mei Chen Nan-Kai Cao Si-Si Zhu Meng Ding Hai-Zhen Liang Ming-Bo Zhao Ke-Wu Zeng Peng-Fei Tu Yong Jiang Euchrestifolines A–O, fifteen novel carbazole alkaloids with potent anti-ferroptotic activity from Murraya euchrestifolia Natural Products and Bioprospecting Murraya euchrestifolia Carbazole Benzopyranocarbazole Anti-ferroptosis NO inhibition Cytotoxicity |
| title | Euchrestifolines A–O, fifteen novel carbazole alkaloids with potent anti-ferroptotic activity from Murraya euchrestifolia |
| title_full | Euchrestifolines A–O, fifteen novel carbazole alkaloids with potent anti-ferroptotic activity from Murraya euchrestifolia |
| title_fullStr | Euchrestifolines A–O, fifteen novel carbazole alkaloids with potent anti-ferroptotic activity from Murraya euchrestifolia |
| title_full_unstemmed | Euchrestifolines A–O, fifteen novel carbazole alkaloids with potent anti-ferroptotic activity from Murraya euchrestifolia |
| title_short | Euchrestifolines A–O, fifteen novel carbazole alkaloids with potent anti-ferroptotic activity from Murraya euchrestifolia |
| title_sort | euchrestifolines a o fifteen novel carbazole alkaloids with potent anti ferroptotic activity from murraya euchrestifolia |
| topic | Murraya euchrestifolia Carbazole Benzopyranocarbazole Anti-ferroptosis NO inhibition Cytotoxicity |
| url | https://doi.org/10.1007/s13659-024-00483-7 |
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