Chemistry:Portimine A
From HandWiki
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| IUPAC name
(3aR,7aS,8S,10R,12S,13S,16R,18S)-10,18-dihydroxy-12-methyl-6-vinyl-2,3,4,5,7a,8,10,11,12,13,14,15,17,18-tetradecahydro-9H-8,16:13,16-diepoxybenzo[2,3]cyclotetradeca[1,2-b]pyrrol-9-one
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3D model (JSmol)
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| Properties | |
| C23H31NO5 | |
| Molar mass | 401.503 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Tracking categories (test):
Portimine A is a cyclic imine natural product produced by the dinoflagellate microalgae Vulcanodinium rugosum. It is a drug lead due to its anti-cancer activity.[1] It seemingly inhibits ribosomal translation activity through an interaction with NMD3,[1] leading to activation of the inflammasome.[2] It is suspected to be causal toxin behind an severe inflammatory skin disease in Senegalese fishermen in 2020 and 2021.[2]
References
- ↑ 1.0 1.1 Tang, Junchen; Li, Weichao; Chiu, Tzu-Yuan; Martínez-Peña, Francisco; Luo, Zengwei; Chong, Christine T.; Wei, Qijia; Gazaniga, Nathalia et al. (2023-10-19). "Synthesis of portimines reveals the basis of their anti-cancer activity". Nature 622 (7983): 507–513. doi:10.1038/s41586-023-06535-1. ISSN 0028-0836. PMID 37730997. Bibcode: 2023Natur.622..507T.
- ↑ 2.0 2.1 Gorse, Léana; Plessis, Loïc; Wearne, Stephen; Paradis, Margaux; Pinilla, Miriam; Chua, Rae; Lim, Seong Soo; Pelluz, Elena et al. (2025-02-13). "Portimine A toxin causes skin inflammation through ZAKα-dependent NLRP1 inflammasome activation". EMBO Molecular Medicine. doi:10.1038/s44321-025-00197-4. ISSN 1757-4684.
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