Portimine A

Progenitors

Name

Vulcanodinium rugosum

Note

Portimine A production was initially reported in V. rugosum strains from New Zealand and France but later all strains were shown to produce portimine A, irrespective of their origin or pinnatoxin profile. Selwood, A.I., Wilkins, A.L., Munday, R., Shi, F., Rhodes, L.L., Holland, P.T., 2013. Portimine: a bioactive metabolite from the benthic dinoflagellate Vulcanodinium rugosum. Tetrahedron Lett. 54(35), 4705-4707. Geiger, M., Desanglois, G., Hogeveen, K., Fessard, V., Leprêtre, T., Mondeguer, F., Guitton, Y., Hervé, F., Séchet, V., Grovel, O., Pouchus, Y.F., Hess, P., 2013. Cytotoxicity, fractionation and dereplication of extracts of the dinoflagellate Vulcanodinium rugosum, a producer of Pinnatoxin G. Mar. Drugs 11(9), 3350-3371.

Vector Species

Name

Mytilus galloprovincialis

Note

Hort, V., Bastardo-Fernandez, I., Nicolas, M., 2023. Exploration of Vulcanodinium rugosum Toxins and their Metabolism Products in Mussels from the Ingril Lagoon Hotspot in France. Mar. Drugs 21(8), 20. Hort, V., Bourcier, S., 2024. Discovery of a series of portimine-A fatty acid esters in mussels. Harmful Algae 134, 102621.

References

Selwood et al., 2013

Selwood, A.I., Wilkins, A.L., Munday, R., Shi, F., Rhodes, L.L., Holland, P.T., 2013. Portimine: a bioactive metabolite from the benthic dinoflagellate Vulcanodinium rugosum. Tetrahedron Lett. 54(35), 4705-4707.

Hort et al., 2023

Hort, V., Bastardo-Fernandez, I., Nicolas, M., 2023. Exploration of Vulcanodinium rugosum Toxins and their Metabolism Products in Mussels from the Ingril Lagoon Hotspot in France. Mar. Drugs 21(8), 20.

Hort et al., 2024

Hort, V., Bourcier, S., 2024. Discovery of a series of portimine-A fatty acid esters in mussels. Harmful Algae 134, 102621.

Geiger et al., 2013

Geiger, M., Desanglois, G., Hogeveen, K., Fessard, V., Leprêtre, T., Mondeguer, F., Guitton, Y., Hervé, F., Séchet, V., Grovel, O., Pouchus, Y.F., Hess, P., 2013. Cytotoxicity, fractionation and dereplication of extracts of the dinoflagellate Vulcanodinium rugosum, a producer of Pinnatoxin G. Mar. Drugs 11(9), 3350-3371.

Structure

Formula

C23H31NO5

Exact mono-isotopic mass

401.22022

Molfile

see chemfiles

Alternative molfiles

n/a

SMILES

C=CC1=C[C@@]([C@]2([H])O3)([H])[C@]4(CCN=C4[C@@H](O)C[C@@]3(CC5)O[C@]5([H])[C@@H](C)C[C@@H](O)C2=O)CC1

Alternative SMILES

n/a

InChi key

JYQBXOZZPLFICX-DSUQWPNCSA-N

Alternative InChi keys

n/a

InChi

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

Alternative InChis

Spectra available

Unknown

Chem files

chemfiles/Port-A.cdxml chemfiles/Port-A.mol

References

Selwood et al., 2013

Selwood, A.I., Wilkins, A.L., Munday, R., Shi, F., Rhodes, L.L., Holland, P.T., 2013. Portimine: a bioactive metabolite from the benthic dinoflagellate Vulcanodinium rugosum. Tetrahedron Lett. 54(35), 4705-4707.

Tang et al., 2023

Tang, J., Li, W., Chiu, T.Y., Martínez-Peña, F., Luo, Z., Chong, C.T., Wei, Q., Gazaniga, N., West, T.J., See, Y.Y., Lairson, L.L., Parker, C.G., Baran, P.S., 2023. Synthesis of portimines reveals the basis of their anti-cancer activity. Nature 622(7983), 507-513.

Certified

False

Certified links

n/a

Non certified reference material

True

Chemical analysis

Research

True

Standardized

Unknown

Validated

Unknown

Official

n/a

Structure recognition assays

Research

Unknown

Standardized

Unknown

Validated

Unknown

Official

n/a

Functional assays

Research

True

Standardized

Unknown

Validated

Unknown

Official

n/a

Animal assays

Research

True

Standardized

Unknown

Validated

Unknown

Official

n/a

Regulatory status

False

Human toxic syndrome(s)

n/a

Organ system toxicity

Dermatotoxicity

Risk assessment

Unknown

Molecular targets known

True

Molecular targets

Inflammation (NLRP1)

Toxic to aquatic animals

Unknown

TEF available

False

Notes

Portimine A was initially described by Selwood et al., 2013, who also showed that it is not very toxic to mice via intraperitoneal injection but highly cytotoxic. A parallel publication (Geiger et al., 2013) also confirmed its highly cytotoxic character and found it isobaric with three other natural products (nakijiquinone A, stachybotrin A and N-carboxy-methyl-smenospongine). Its structure was later confirmed through chemical synthesis by Tang et al., 2023, who also proposed its use as anticancer drug due to the apoptotic character in several cell lines. The inflammatory character was demonstrated by Gorse et al., 2025, explaining the skin damage observed in bathing people in Cuba in 2015 (Moreira-Gonzalez et al., 2021) and in artisanal drift-net fishermen in Senegal in 2020 and 2021. Until 2025, all strains of Vulcanodinium rugosum have been shown to produce portimine A, irrespective of their profile of pinnatoxins (or the absence of pinnatoxins).

References

Selwood et al., 2013

Selwood, A.I., Wilkins, A.L., Munday, R., Shi, F., Rhodes, L.L., Holland, P.T., 2013. Portimine: a bioactive metabolite from the benthic dinoflagellate Vulcanodinium rugosum. Tetrahedron Lett. 54(35), 4705-4707.

Geiger et al., 2013

Geiger, M., Desanglois, G., Hogeveen, K., Fessard, V., Leprêtre, T., Mondeguer, F., Guitton, Y., Hervé, F., Séchet, V., Grovel, O., Pouchus, Y.F., Hess, P., 2013. Cytotoxicity, fractionation and dereplication of extracts of the dinoflagellate Vulcanodinium rugosum, a producer of Pinnatoxin G. Mar. Drugs 11(9), 3350-3371.

Moreira-Gonzales et al, 2021

Moreira-Gonzalez, A.R., Comas-Gonzalez, A., Valle-Pombrol, A., Seisdedo-Losa, M., Hernandez-Leyva, O., Fernandes, L.F., Chomerat, N., Bilien, G., Herve, F., Rovillon, G.A., Hess, P., Alonso-Hernandez, C.M., Mafra, L.L., 2021. Summer bloom of Vulcanodinium rugosum in Cienfuegos Bay (Cuba) associated to dermatitis in swimmers. Sci. Total Environ. 757, 12.

Tang et al., 2023

Tang, J., Li, W., Chiu, T.Y., Martínez-Peña, F., Luo, Z., Chong, C.T., Wei, Q., Gazaniga, N., West, T.J., See, Y.Y., Lairson, L.L., Parker, C.G., Baran, P.S., 2023. Synthesis of portimines reveals the basis of their anti-cancer activity. Nature 622(7983), 507-513.

Gorse et al., 2025

Gorse, L., Plessis, L., Wearne, S., Paradis, M., Pinilla, M., Chua, R., Lim, S.S., Pelluz, E., TOH, G.-A., Mazars, R., Bomfim, C., Hervé, F., Lhaute, K., Réveillon, D., Suire, B., Ravon-Katossky, L., Benoist, T., Fromont, L., Péricat, D., Neil Mertens, K., Derrien, A., Terre-Terrillon, A., Chomérat, N., Bilien, G., Séchet, V., Carpentier, L., Fall, M., Sonko, A., Hakim, H., Sadio, N., Bourdeaux, J., Cougoule, C., Henras, A.K., Perez-Oliva, A.B., Brehmer, P., Roca, F.J., Zhong, F.L., Common, J., Meunier, E., Hess, P., 2025. Portimine A toxin causes skin inflammation through ZAKα-dependent NLRP1 inflammasome activation. EMBO Molecular Medicine 17(3), 535-562.

Philipp Hess

Contact