Polygodial

Polygodial
IUPAC name (1R,4aS,8aS)-5,5,8a-Trimethyl-1,4,4a,6,7,8-hexahydronaphthalene-1,2-dicarboxaldehyde
Other names Poligodial; Tadeodal; Tadeonal; Drim-7-ene-11,12-dial
Identifiers
CAS number	6754-20-7 Y
PubChem	72503
ChEMBL	CHEMBL254550 N
Jmol-3D images	Image 1
SMILES CC1(CCC[C@]2([C@H]1CC=C([C@@H]2C=O)C=O)C)C
Properties
Molecular formula	C15H22O2
Molar mass	234.33398
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Polygodial is an active constituent of Dorrigo Pepper, Mountain Pepper, Horopito, Canelo, Paracress and Water-pepper.^[1][2][3][4]

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

It elicits a warm and pungent flavour.

The biological activity of polygodial has been reported in the scientific literature to include antifungal and antimicrobial activities,^[5][6][7] antihyperalgesia,^[8] potent attachment-inhibitory activity,^[9] insect antifeedant activity,^[10] antinociception ^[11][12] vasorelaxation action in vessels of rabbit and guinea pig,^[13] anti-inflammatory and antiallergic activities ^[14][15][16]

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.^[17]

It is also used as an insecticide for its antifeedant property, which causes insects to starve.

References

1. ^ Beattie, G.A.C., Spray Oils Beyond 2000, University of Western Queensland, ISBN 1-86341-902-0
2. ^ McCallion RF, Cole ALJ, Walker JRL, Blunt JW, Munro MHG. Antibiotics substances from New Zealand plants II. Polygodial, an anti-Candida agent from Pseudowintera colorata. Planta Med 1982; 44: 134-138.
3. ^ Muñoz-Conchaa, D., Vogelb, H., Yunesc, R., Razmilicd, I., Brescianic, L., and Malheirosc, A., Presence of polygodial and drimenol in Drimys populations from Chile, Biochemical Systematics and Ecology, Volume 35, Issue 7, July 2007, Pages 434-438
4. ^ M Jonassohn (1996)Sesquiterpenoid unsaturated dialdehydes - Structural properties that affect reactivity and bioctivity. Doctoral thesis, Lund University, Sweden. ISBN 91-628-2215-2. [1]PDF (730 KiB)
5. ^ Anke, H. & Sterner, O. (1991). Comparison of the antimicrobial and cytotoxic activities of twenty unsaturated sesquiterpene dialdehydes from plants and mushrooms. Planta Medica, 57(4), 344-346.
6. ^ Lee S H, Lee J R, Lunde C S, Kubo I. (1999). In Vitro Antifungal Susceptibilities of Candida albicans and other Fungal Pathogens to Polygodial, a Sesquiterpene Dialdehyde, Planta Medica, vol 65, pp205-208
7. ^ Kubo, I., Fujita, K. & Lee, S.H., (2001). Antifungal Mechanism of Polygodial. Journal of Agricultural and Food Chemistry, 49(3), 1607-1611.
8. ^ Mendes, G.L. et al., (1998). Anti-hyperalgesic properties of the extract and of the main sesquiterpene polygodial isolated from the barks of Drymis winteri (Winteraceae). Life Sciences, 63(5), 369-381.
9. ^ Ban, T., Singh, I.P. & Etoh, H., (2000). Polygodial, a potent attachment-inhibiting substance for the blue mussel, Mytilus edulis galloprovincialis from Tasmannia lanceolata. Bioscience, Biotechnology, and Biochemistry, 64(12), 2699-2701.
10. ^ Caprioli, V. et al., (1987). Insect antifeedant activity and hot taste for humans of selected natural and synthetic 1,4-dialdehydes. Journal of Natural Products, 50(2), 146-151.
11. ^ Mendes, G.L. et al., 2000. Assessment of mechanisms involved in antinociception caused by sesquiterpene polygodial. The Journal of Pharmacology and Experimental Therapeutics, 292(1), 164-172.
12. ^ Malheiros, A. et al., (2001). A sesquiterpene drimane with antinociceptive activity from Drimys winteri bark. Phytochemistry, 57(1), 103-107.
13. ^ Andre, E. et al., (1999). Mechanisms underlying the relaxation caused by the sesquiterpene polygodial in vessels from rabbit and guinea-pig. European Journal of Pharmacology, 386(1), 47-53.
14. ^ Tratsk, K.S. et al., (1997). Anti-allergic effects and oedema inhibition caused by the extract of Drymis winteri. Inflammation Research: Official Journal of the European Histamine Research Society ... [et Al, 46(12), 509-514.
15. ^ da Cunha, F.M. et al., (2001). Additional evidence for the anti-inflammatory and anti-allergic properties of the sesquiterpene polygodial. Life Sciences, 70(2), 159-169.
16. ^ Martin, W.J. et al., (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, 47(5), 616-621.
17. ^ Kubo , Fujita K, Lee S H, Ha T J. Antibacterial Activity of Polygodial, Phytotherapy Research, 2005, 19, pp 1013-1017