Polygodial
Chemical compound
From Wikipedia, the free encyclopedia
Polygodial a is chemical compound found in dorrigo pepper, mountain pepper, horopito, canelo, paracress, water-pepper, and Dendrodoris limbata.[1][2][3][4][5] It is a drimane-type sesquiterpene dialdehyde with the chemical formula C15H22O2.
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| Names | |
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| IUPAC name
Drim-7-ene-11,12-dial | |
| Systematic IUPAC name
(1R,4aS,8aS)-5,5,8a-Trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalene-1,2-dicarbaldehyde | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C15H22O2 | |
| Molar mass | 234.339 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[6]
Biological activity
The in vitro biological activity of polygodial has been reported in the scientific literature to include antifungal and antimicrobial activities,[7][8][9] antihyperalgesia,[10] potent attachment-inhibitory activity,[11] insect antifeedant activity,[12] antinociception,[13][14] vasorelaxing action in vessels of rabbit and guinea pig,[15] anti-inflammatory and antiallergic activities.[16][17][18]
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.[19]
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.[20] Polygodial was found to activate chemotactile receptors in the tentacles of cephalopods (octopus, squid) that prey on sea slugs, triggering avoidance behavior.[21]