Pinnatoxin D

Progenitors

Name

Vulcanodinium rugosum

Vector Species

Name

Pinna muricata

References

Chou et al.,, 1996

Chou, T., Haino, T., Kuramoto, M., Uemura, D., 1996. Isolation and structure of pinnatoxin D, a new shellfish poison from the okinawan bivalve Pinna muricata. Tetrahedron Lett. 37(23), 4027-4030.

Nézan & Chomérat,, 2011

Nézan, E., Chomérat, N., 2011. Vulcanodinium rugosum gen. et sp. nov. (Dinophyceae), un nouveau dinoflagellé marin de la côte méditerraneenne française. Cryptogamie, Algologie 32(1), 3-18.

Structure

Formula

C45H67NO10

Exact mono-isotopic mass

781.4765

Molfile

see chemfiles

Alternative molfiles

n/a

SMILES

C[C@@H](CN=C1CCCC(C[C@@H]2CC[C@](O)(C)[C@](O2)(O3)CC[C@@]3(O4)C[C@H](C)[C@H](O)[C@@H]4C5)=C)[C@@H](C)C[C@@]61[C@]([C@@H]7O[C@]85C[C@@H](C)C[C@H]7O8)([H])C=C(C(CCC(O)=O)=O)CC6

Alternative SMILES

n/a

InChi key

MRPUCWZEBLNKPU-GWTPBJLHSA-N

Alternative InChi keys

n/a

InChi

InChI=1S/C45H67NO10/c1-26-8-7-9-37-42(22-28(3)30(5)25-46-37)15-12-31(34(47)10-11-38(48)49)20-33(42)40-35-19-27(2)21-44(53-35,55-40)24-36-39(50)29(4)23-43(54-36)16-17-45(56-43)41(6,51)14-13-32(18-26)52-45/h20,27-30,32-33,35-36,39-40,50-51H,1,7-19,21-25H2,2-6H3,(H,48,49)/t27-,28-,29-,30-,32-,33+,35+,36-,39-,40-,41+,42+,43-,44-,45+/m0/s1

Alternative InChis

Spectra available

True

Chem files

chemfiles/PnTX-D.cdxml chemfiles/PnTX-D.mol

References

Chou et al.,, 1996

Chou, T., Haino, T., Kuramoto, M., Uemura, D., 1996. Isolation and structure of pinnatoxin D, a new shellfish poison from the okinawan bivalve Pinna muricata. Tetrahedron Lett. 37(23), 4027-4030.

Certified

Unknown

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

Unknown

Standardized

Unknown

Validated

Unknown

Official

n/a

Animal assays

Research

Unknown

Standardized

Unknown

Validated

Unknown

Official

n/a

References

Selwood et al.,, 2010

Selwood, A.I., Miles, C.O., Wilkins, A.L., van Ginkel, R., Munday, R., Rise, F., McNabb, P., 2010. Isolation, Structural Determination and Acute Toxicity of Pinnatoxins E, F and G. J. Agric. Food Chem. 58(10), 6532-6542.

Selwood et al.,, 2025

Selwood, A.I., Miles, C.O., Wilkins, A.L., Rise, F., Finch, S.C., van Ginkel, R., 2025. Structural Characterization of Pinnatoxin Isomers. Mar. Drugs 23(3), 11.

Regulatory status

Unknown

Human toxic syndrome(s)

n/a

Organ system toxicity

n/a

Risk assessment

Unknown

Molecular targets known

True

Molecular targets

Nicotinic acetylcholine receptors

Toxic to aquatic animals

Unknown

TEF available

False

Notes

Pinnatoxin D is not produced by Vulcanodinium rugosum (or other microalgae) but is a shellfish metabolite originally purified by Chou et al., 1996, from Pinna muricata. For metabolism hypotheses see Selwood et al., 2010. PnTX-D likely derives from metabolism of PnTX-E (via -F), which in turn is produced by certain strains of V. rugosum. Isopinnatoxins have been described for PnTX-E, -F, -D and -H. These isoforms are formed through acid-catalyzed ring-opening of the D-ring and transformation of the 6-membered D-ring into a five-membered D-ring thanks to an OH-group at C22. (Selwood et al., 2025)

References

Chou et al.,, 1996

Chou, T., Haino, T., Kuramoto, M., Uemura, D., 1996. Isolation and structure of pinnatoxin D, a new shellfish poison from the okinawan bivalve Pinna muricata. Tetrahedron Lett. 37(23), 4027-4030.

Selwood et al.,, 2010

Selwood, A.I., Miles, C.O., Wilkins, A.L., van Ginkel, R., Munday, R., Rise, F., McNabb, P., 2010. Isolation, Structural Determination and Acute Toxicity of Pinnatoxins E, F and G. J. Agric. Food Chem. 58(10), 6532-6542.

Selwood et al.,, 2025

Selwood, A.I., Miles, C.O., Wilkins, A.L., Rise, F., Finch, S.C., van Ginkel, R., 2025. Structural Characterization of Pinnatoxin Isomers. Mar. Drugs 23(3), 11.

Philipp Hess

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