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从东风桔中分离得到的15个具有强抗铁死亡活性的新型咔唑生物碱——东风桔叶碱A - O

Euchrestifolines A-O, fifteen novel carbazole alkaloids with potent anti-ferroptotic activity from Murraya euchrestifolia.

作者信息

Chen Yue-Mei, Cao Nan-Kai, Zhu Si-Si, Ding Meng, Liang Hai-Zhen, Zhao Ming-Bo, Zeng Ke-Wu, Tu Peng-Fei, Jiang Yong

机构信息

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, 100191, People's Republic of China.

出版信息

Nat Prod Bioprospect. 2025 Jan 2;15(1):5. doi: 10.1007/s13659-024-00483-7.

DOI:10.1007/s13659-024-00483-7
PMID:39745519
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11695541/
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 EC 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.

摘要

从宽叶臭黄荆中获得了15种新型咔唑生物碱，即宽叶臭黄荆碱A - O（1 - 15）。通过光谱分析、莫舍尔酯法、计算ECD以及过渡金属配合物ECD方法对其结构进行了阐明。值得注意的是，宽叶臭黄荆碱A - C（1 - 3）是首次被鉴定出的天然存在的吡咯烷酮咔唑，而宽叶臭黄荆碱D - F（4 - 6）代表了含有苯丙烷基部分的稀有咔唑生物碱；宽叶臭黄荆碱G（7）具有独特的苯并吡喃并咔唑骨架。更重要的是，这些化合物表现出显著的抗铁死亡活性，同时对一氧化氮（NO）的产生具有抑制作用，并且具有明显的细胞毒性。本研究首次揭示了咔唑对铁死亡的抑制作用，一些咔唑的EC值在0.04至1 μM之间，大大低于阳性对照铁抑素-1。总之，这项研究不仅增进了我们对咔唑生物碱的理解，还为发现与铁死亡相关的先导化合物开辟了新途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db85/11695541/e258f588307f/13659_2024_483_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db85/11695541/335b2928e4cf/13659_2024_483_Fig1_HTML.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db85/11695541/40cfeaef0cc2/13659_2024_483_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db85/11695541/b4116280593e/13659_2024_483_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db85/11695541/e258f588307f/13659_2024_483_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db85/11695541/335b2928e4cf/13659_2024_483_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db85/11695541/c0174d47a6b5/13659_2024_483_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db85/11695541/8bb14f23698a/13659_2024_483_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db85/11695541/d61a1e681974/13659_2024_483_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db85/11695541/40cfeaef0cc2/13659_2024_483_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db85/11695541/b4116280593e/13659_2024_483_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db85/11695541/e258f588307f/13659_2024_483_Sch1_HTML.jpg

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Natural carbazole alkaloid murrayafoline A displays potent anti-neuroinflammatory effect by directly targeting transcription factor Sp1 in LPS-induced microglial cells.
天然咔唑生物碱 Murrayafoline A 通过直接靶向 LPS 诱导的小胶质细胞中的转录因子 Sp1 发挥强大的抗神经炎症作用。
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