Portimine B

Progenitors

Name

Vulcanodinium rugosum

Vector Species

No vector species registered

References

Fribley et al., 2019

Fribley, A.M., Xi, Y., Makris, C., Alves-de-Souza, C., York, R., Tomas, C., Wright, J.L.C., Strangman, W.K., 2019. Identification of Portimine B, a New Cell Permeable Spiroimine That Induces Apoptosis in Oral Squamous Cell Carcinoma. Acs Medicinal Chemistry Letters 10(2), 175-179.

Structure

Formula

C23H29NO5

Exact mono-isotopic mass

399.20457

Molfile

see chemfiles

Alternative molfiles

n/a

SMILES

C=CC1=C[C@@]([C@]2([H])O[C@@](CC3)(C4)O[C@]3([H])[C@@H](C)C[C@@H](O)C2=O)([H])[C@]5(CCN=C5C4=O)CC1

Alternative SMILES

n/a

InChi key

PYKGWXPCJKHMSM-JMVHQBGZSA-N

Alternative InChi keys

n/a

InChi

InChI=1S/C23H29NO5/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/h3,11,13,15-16,18,20,25H,1,4-10,12H2,2H3/t13-,15+,16+,18-,20-,22+,23-/m0/s1

Alternative InChis

Spectra available

Unknown

Chem files

chemfiles/Port-B.cdxml chemfiles/Port-B.mol

References

Fribley et al., 2019

Fribley, A.M., Xi, Y., Makris, C., Alves-de-Souza, C., York, R., Tomas, C., Wright, J.L.C., Strangman, W.K., 2019. Identification of Portimine B, a New Cell Permeable Spiroimine That Induces Apoptosis in Oral Squamous Cell Carcinoma. Acs Medicinal Chemistry Letters 10(2), 175-179.

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.

Wood et al., 2024

Wood, J.S., Tang, J., Strangman, W.K., Williamson, R.T., 2024. Advanced Structure Analysis Reveals a Transient Portimine B Hydrate. J Nat Prod 87(8), 2120-2125.

Certified

False

Certified links

n/a

Non certified reference material

Unknown

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

Unknown

Standardized

Unknown

Validated

Unknown

Official

n/a

References

Wood et al., 2024

Wood, J.S., Tang, J., Strangman, W.K., Williamson, R.T., 2024. Advanced Structure Analysis Reveals a Transient Portimine B Hydrate. J Nat Prod 87(8), 2120-2125.

Regulatory status

Unknown

Human toxic syndrome(s)

n/a

Organ system toxicity

Dermatotoxicity

Risk assessment

Unknown

Molecular targets known

Unknown

Molecular targets

Inflammation (NLRP1)

Toxic to aquatic animals

Unknown

TEF available

False

TEF References

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.

Notes

Portimine B was isolated and structurally characterized initially by Fribley et al., 2019. Later on, the structure was corrected through chemical synthesis by Tang et al., 2023. However, incongruence between the newly assigned structure by Tang et al., 2023, and LC-MS/MS analysis of the natural and synthetic product (LC-MS/MS showing an additional water in the molecule) led Wood et al., 2024, to investigate further and propose that in acidic, aqueous solutions a transient hydrate is formed as a gem-diol immediately and the measured mass [M+H+] is always 418.2230 (C23H32NO6), instead of the mass that should be measured for the molecule as characterized by NMR 400.2110 (C23H30NO5). A water loss is a most abundant fragment in LC-MS/MS analysis. Unfortunatly, at this stage is cannot be clarified in which form the toxin occurs in nature. However, Gorse et al., 2025, also were able to show that portimine B is significantly less cytotoxic in cellular models compared to portimine A (by at least a factor of 25-50).

References

Fribley et al., 2019

Fribley, A.M., Xi, Y., Makris, C., Alves-de-Souza, C., York, R., Tomas, C., Wright, J.L.C., Strangman, W.K., 2019. Identification of Portimine B, a New Cell Permeable Spiroimine That Induces Apoptosis in Oral Squamous Cell Carcinoma. Acs Medicinal Chemistry Letters 10(2), 175-179.

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.

Wood et al., 2024

Wood, J.S., Tang, J., Strangman, W.K., Williamson, R.T., 2024. Advanced Structure Analysis Reveals a Transient Portimine B Hydrate. J Nat Prod 87(8), 2120-2125.

Philipp Hess

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