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Polygodial

Polygodial is chemical compound found in dorrigo pepper, mountain pepper, horopito, canelo, paracress, water-pepper, and Dendrodoris limbata.

Chemically it is a drimane-type sesquiterpene dialdehyde of formula C15H22O2.

Polygodial elicits a warm and pungent flavour.

The compound activates the TRPA1 pain receptor in nerve endings in the mouth that mediate the sensation of pungency.

The in vitro biological activity of polygodial has been reported in the scientific literature to include antifungal and antimicrobial activities, antihyperalgesia, potent attachment-inhibitory activity, insect antifeedant activity, antinociception, vasorelaxing action in vessels of rabbit and guinea pig, anti-inflammatory and antiallergic activities.

Polygodial’s primary antifungal action is as a nonionic surfactant, disrupting the lipid-protein interface of integral proteins nonspecifically, denaturing their functional conformation. It is also likely that polygodial permeates by passive diffusion across the plasma membrane, and once inside the cells may react with a variety of intracellular compounds.

It is also an insecticide with antifeedant properties, which causes insects to starve.

Polygodial is produced for chemical defense by Doridoidea (dorid nudibranchs), a superfamily of shell-less sea slugs. Polygodial was found to activate chemotactile receptors in the tentacles of cephalopods (octopus, squid) that prey on sea slugs, triggering avoidance behavior.

References

References

  1. Beattie, G.A.C., ''Spray Oils Beyond 2000'', University of Western Queensland, {{ISBN. 1-86341-902-0
  2. (1982). "Antibiotic Substances from New Zealand Plants". Planta Medica.
  3. (2007). "Presence of polygodial and drimenol in Drimys populations from Chile". Biochemical Systematics and Ecology.
  4. (1983). "Dorid Nudibranch Elaborates Its Own Chemical Defense". Science.
  5. Escalera, Jasmine. (2008-10-29). "TRPA1 Mediates the Noxious Effects of Natural Sesquiterpene Deterrents". Journal of Biological Chemistry.
  6. (1991). "Comparison of the Antimicrobial and Cytotoxic Activities of Twenty Unsaturated Sesquiterpene Dialdehydes from Plants and Mushrooms". Planta Medica.
  7. (1999). "In Vitro Antifungal Susceptibilities of Candida albicans and Other Fungal Pathogens to Polygodial, a Sesquiterpene Dialdehyde". Planta Medica.
  8. (2001). "Antifungal Mechanism of Polygodial". Journal of Agricultural and Food Chemistry.
  9. (1998). "Anti-hyperalgesic properties of the extract and of the main sesquiterpene polygodial isolated from the barks of Drymis winteri (Winteraceae)". Life Sciences.
  10. (2000). "Polygodial, a Potent Attachment-inhibiting Substance for the Blue Mussel,Mytilus edulis galloprovincialisfrom ''Tasmannia'' lanceolata". Bioscience, Biotechnology, and Biochemistry.
  11. (1987). "Insect Antifeedant Activity and Hot Taste for Humans of Selected Natural and Synthetic 1,4-Dialdehydes". Journal of Natural Products.
  12. (2000). "Assessment of mechanisms involved in antinociception caused by sesquiterpene polygodial". The Journal of Pharmacology and Experimental Therapeutics.
  13. (2001). "A sesquiterpene drimane with antinociceptive activity from Drimys winteri bark". Phytochemistry.
  14. (1999). "Mechanisms underlying the relaxation caused by the sesquiterpene polygodial in vessels from rabbit and guinea-pig". European Journal of Pharmacology.
  15. (1997). "Anti-allergic effects and oedema inhibition caused by the extract of Drymis winteri". Inflammation Research.
  16. (2001). "Additional evidence for the anti-inflammatory and anti-allergic properties of the sesquiterpene polygodial". Life Sciences.
  17. (2009). "Sesquiterpene dialdehydes inhibit MSU crystal-induced superoxide production by infiltrating neutrophils in an in vivo model of gouty inflammation". Free Radical Biology and Medicine.
  18. (2005). "Antibacterial activity of polygodial". Phytotherapy Research.
  19. Cimino, Guido. (1983-03-11). "Dorid Nudibranch Elaborates Its Own Chemical Defense". Science.
  20. Kang, Guipeun. (2023-04-12). "Sensory specializations drive octopus and squid behaviour". Nature.
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aldehydes pungent-flavors sesquiterpenes
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