Portimine A

Last updated
Portimine A
Portimine-A-Structure.svg
Names
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
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C23H31NO5/c1-3-14-4-6-22-8-9-24-21(22)17(26)12-23-7-5-18(28-23)13(2)10-16(25)19(27)20(29-23)15(22)11-14/h3,11,13,15-18,20,25-26H,1,4-10,12H2,2H3/t13-,15+,16+,17-,18-,20-,22+,23+/m0/s1
    Key: JYQBXOZZPLFICX-CPWUQFAPSA-N
  • C[C@H]1C[C@H](C(=O)[C@@H]2[C@H]3C=C(CC[C@@]34CCN=C4[C@H](C[C@]5(O2)CC[C@@H]1O5)O)C=C)O
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).

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 was the causal toxin behind an severe inflammatory skin disease in Senegalese fishermen in 2020 and 2021. [2]

References

  1. 1 2 Tang, Junchen; Li, Weichao; Chiu, Tzu-Yuan; Martínez-Peña, Francisco; Luo, Zengwei; Chong, Christine T.; Wei, Qijia; Gazaniga, Nathalia; West, Thomas J.; See, Yi Yang; Lairson, Luke L.; Parker, Christopher G.; Baran, Phil S. (2023-10-19). "Synthesis of portimines reveals the basis of their anti-cancer activity". Nature. 622 (7983): 507–513. Bibcode:2023Natur.622..507T. doi:10.1038/s41586-023-06535-1. ISSN   0028-0836. PMC   10699793 . PMID   37730997.
  2. 1 2 Gorse, Léana; Plessis, Loïc; Wearne, Stephen; Paradis, Margaux; Pinilla, Miriam; Chua, Rae; Lim, Seong Soo; Pelluz, Elena; Toh, Gee-Ann; Mazars, Raoul; Bomfim, Caio; Hervé, Fabienne; Lhaute, Korian; Réveillon, Damien; Suire, Bastien; Ravon-Katossky, Léa; Benoist, Thomas; Fromont, Léa; Péricat, David; Neil Mertens, Kenneth; Derrien, Amélie; Terre-Terrillon, Aouregan; Chomérat, Nicolas; Bilien, Gwenaël; Séchet, Véronique; Carpentier, Liliane; Fall, Mamadou; Sonko, Amidou; Hakim, Hadi; Sadio, Nfally; Bourdeaux, Jessie; Cougoule, Céline; Henras, Anthony K; Perez-Oliva, Ana Belen; Brehmer, Patrice; Roca, Francisco J; Zhong, Franklin L; Common, John; Meunier, Etienne; Hess, Philipp (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. PMC   11903881 .
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