Pinnatoxin F

Progenitors

Name

Vulcanodinium rugosum

Note

Initially isolated from oysters (Magallana gigas, formerly Crassostrea gigas) and razor fish (Pinna bicolor) by Selwood et al., 2010 in New Zealand and Australia, the toxins were also rapidly identified in sediment-derived strains of dinoflagellates (Rhodes et al., 2010), later identified as Vulcanodinium rugosum (Nézan and Chomérat, 2011 & Rhodes et al., 2011)

Vector Species

Name

Magallana gigas

Note

Initially isolated from oysters (Magallana gigas, formerly Crassostrea gigas) and razor fish (Pinna bicolor) by Selwood et al., 2010 in New Zealand and Australia, the toxins were also rapidly identified in sediment-derived strains of dinoflagellates (Rhodes et al., 2010), later identified as Vulcanodinium rugosum (Nézan and Chomérat, 2011 & Rhodes et al., 2011)

Name

Pinna bicolor

Note

Initially isolated from oysters (Magallana gigas, formerly Crassostrea gigas) and razor fish (Pinna bicolor) by Selwood et al., 2010 in New Zealand and Australia, the toxins were also rapidly identified in sediment-derived strains of dinoflagellates (Rhodes et al., 2010), later identified as Vulcanodinium rugosum (Nézan and Chomérat, 2011 & Rhodes et al., 2011)

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.

Rhodes et al., 2010

Rhodes, L., Smith, K., Selwood, A.I., McNabb, P., van Ginkel, R., Holland, P.T., Munday, R., 2010. Production of pinnatoxins by a peridinoid dinoflagellate isolated from Northland, New Zealand. Harmful Algae 9(4), 384-389.

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.

Rhodes et al., 2011

Rhodes, L., Smith, K., Selwood, A., McNabb, P., Munday, R., Suda, S., Molenaar, S., Hallegraeff, G., 2011. Dinoflagellate Vulcanodinium rugosum identified as the causative organism of pinnatoxins in Australia, New Zealand and Japan. Phycologia 50(6), 624-628.

Structure

Formula

C45H67NO9

Exact mono-isotopic mass

765.48158

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@H]9OC(CC9)=O)CC6

Alternative SMILES

n/a

InChi key

KMYKHQRQBUANHP-YUHUXZIXSA-N

Alternative InChi keys

n/a

InChi

InChI=1S/C45H67NO9/c1-26-8-7-9-37-42(22-28(3)30(5)25-46-37)15-12-31(34-10-11-38(47)50-34)20-33(42)40-35-19-27(2)21-44(52-35,54-40)24-36-39(48)29(4)23-43(53-36)16-17-45(55-43)41(6,49)14-13-32(18-26)51-45/h20,27-30,32-36,39-40,48-49H,1,7-19,21-25H2,2-6H3/t27-,28-,29-,30-,32-,33+,34-,35+,36-,39-,40-,41+,42+,43-,44-,45+/m0/s1

Alternative InChis

Spectra available

Unknown

Chem files

chemfiles/PnTX-F.cdxml chemfiles/PnTX-F.mol

Certified

True

Certified links

• Merck
  Trace Cert - certification

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

True

Standardized

Unknown

Validated

Unknown

Official

n/a

Regulatory status

False

Human toxic syndrome(s)

n/a

Organ system toxicity

n/a

Risk assessment

Unknown

Molecular targets known

Unknown

Molecular targets

Nicotinic acetylcholine receptors

Toxic to aquatic animals

Unknown

TEF available

False

Notes

PnTX-F is likely formed from PnTX-E and metabolised in shellfish to PnTX-D. 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

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

Contact