Polygodial

Last updated
Polygodial
Polygodial.svg
Names
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
Poligodial; Tadeodal; Tadeonal
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C15H22O2/c1-14(2)7-4-8-15(3)12(10-17)11(9-16)5-6-13(14)15/h5,9-10,12-13H,4,6-8H2,1-3H3/t12-,13-,15+/m0/s1 X mark.svgN
    Key: AZJUJOFIHHNCSV-KCQAQPDRSA-N X mark.svgN
  • InChI=1/C15H22O2/c1-14(2)7-4-8-15(3)12(10-17)11(9-16)5-6-13(14)15/h5,9-10,12-13H,4,6-8H2,1-3H3/t12-,13-,15+/m0/s1
    Key: AZJUJOFIHHNCSV-KCQAQPDRBV
  • CC1(CCC[C@]2([C@H]1CC=C([C@@H]2C=O)C=O)C)C
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Polygodial is chemical compound found in dorrigo pepper, mountain pepper, horopito, canelo, paracress, water-pepper, and Dendrodoris limbata. [1] [2] [3] [4] [5]

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. [6]

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.

Related Research Articles

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References

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