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).
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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.

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]

References

  1. ↑ Beattie, G.A.C., Spray Oils Beyond 2000, University of Western Queensland, ISBN   1-86341-902-0
  2. ↑ McCallion, Rosemary; Cole, A.; Walker, J.; Blunt, J.; Munro, M. (1982). "Antibiotic Substances from New Zealand Plants". Planta Medica. 44 (3): 134–138. doi:10.1055/s-2007-971422. PMID   7089094.
  3. ↑ Muñoz-Concha, Diego; Vogel, Hermine; Yunes, Rosendo; Razmilic, Iván; Bresciani, Louisiane; Malheiros, Angela (2007). "Presence of polygodial and drimenol in Drimys populations from Chile". Biochemical Systematics and Ecology. 35 (7): 434–438. Bibcode:2007BioSE..35..434M. doi:10.1016/j.bse.2006.10.019.
  4. ↑ Jonassohn, Mikael (1996). Sesquiterpenoid unsaturated dialdehydes: structural properties that affect reactivity and bioactivity (PDF) (PhD). Lund University. ISBN   91-628-2215-2. Archived from the original (PDF) on 2011-10-03. Retrieved 2008-01-30.
  5. ↑ Cimino, G.; De Rosa, S.; De Stefano, S.; Sodano, G.; Villani, G. (1983). "Dorid Nudibranch Elaborates Its Own Chemical Defense". Science. 219 (4589): 1237–1238. Bibcode:1983Sci...219.1237C. doi:10.1126/science.219.4589.1237. PMID   17771309. S2CID   8590649.
  6. ↑ Escalera, Jasmine; von Hehn, Christian A.; Bessac, Bret F.; Sivula, Michael; Jordt, Sven-Eric (2008-10-29). "TRPA1 Mediates the Noxious Effects of Natural Sesquiterpene Deterrents". Journal of Biological Chemistry. 283 (35): 24136–24144. doi: 10.1074/jbc.M710280200 . PMC   2527119 . PMID   18550530.
  7. ↑ Anke, Heidrun; Sterner, Olov (1991). "Comparison of the Antimicrobial and Cytotoxic Activities of Twenty Unsaturated Sesquiterpene Dialdehydes from Plants and Mushrooms". Planta Medica. 57 (4): 344–346. doi:10.1055/s-2006-960114. PMID   1775575.
  8. ↑ Lee, Sang Hwa; Lee, Jae Ran; Lunde, Christopher S.; Kubo, Isao (1999). "In Vitro Antifungal Susceptibilities of Candida albicans and Other Fungal Pathogens to Polygodial, a Sesquiterpene Dialdehyde". Planta Medica. 65 (3): 204–208. doi:10.1055/s-1999-13981. PMID   10232062.
  9. ↑ Kubo, Isao; Fujita, Ken'Ichi; Lee, Sang Hwa (2001). "Antifungal Mechanism of Polygodial". Journal of Agricultural and Food Chemistry. 49 (3): 1607–1611. doi:10.1021/jf000136g. PMID   11312903.
  10. ↑ Mendes, Gilboé L.; Santos, Adair R.S.; Campos, Maria M.; Tratsk, Karla S.; Yunes, Rosendo A.; Filho, Valdir Cechinel; Calixto, Joăo B. (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. doi:10.1016/s0024-3205(98)00285-9. PMID   9714424.
  11. ↑ Ban, Takahiro; Singh, Inder Pal; Etoh, Hideo (2000). "Polygodial, a Potent Attachment-inhibiting Substance for the Blue Mussel,Mytilus edulis galloprovincialisfrom Tasmannia lanceolata". Bioscience, Biotechnology, and Biochemistry. 64 (12): 2699–2701. doi: 10.1271/bbb.64.2699 . PMID   11210140.
  12. ↑ Caprioli, Vincenzo; Cimino, Guido; Colle, Roberto; Gavagnin, Margherita; Sodano, Guido; Spinella, Aldo (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. doi:10.1021/np50050a002. PMID   3655790.
  13. ↑ Mendes, G. L.; Santos, A. R.; Malheiros, A.; Filho, V. C.; Yunes, R. A.; Calixto, J. B. (2000). "Assessment of mechanisms involved in antinociception caused by sesquiterpene polygodial". The Journal of Pharmacology and Experimental Therapeutics. 292 (1): 164–72. PMID   10604944.
  14. ↑ Malheiros, Angela; Filho, Valdir Cechinel; Schmitt, Clarisse B.; Santos, Adair R.S; Scheidt, Cristiano; Calixto, João B.; Monache, Franco Delle; Yunes, Rosendo A. (2001). "A sesquiterpene drimane with antinociceptive activity from Drimys winteri bark". Phytochemistry. 57 (1): 103–107. Bibcode:2001PChem..57..103M. doi:10.1016/s0031-9422(00)00515-x. PMID   11336250.
  15. ↑ André, Eunice; Malheiros, Ângela; Cechinel-Filho, Valdir; Yunes, Rosendo A.; Calixto, João B. (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. doi:10.1016/s0014-2999(99)00719-0. PMID   10611463.
  16. ↑ Tratsk, K. S.; Campos, M. M.; Vaz, Z. R.; Filho, V. C.; Schlemper, V.; Yunes, R. A.; Calixto, J. B. (1997). "Anti-allergic effects and oedema inhibition caused by the extract of Drymis winteri". Inflammation Research. 46 (12): 509–514. doi:10.1007/s000110050234. PMID   9459082. S2CID   206862953.
  17. ↑ Da Cunha, Fernanda M.; Fröde, Tânia S.; Mendes, Gilboé L.; Malheiros, Angela; Filho, Valdir Cechinel; Yunes, Rosendo A.; Calixto, João B. (2001). "Additional evidence for the anti-inflammatory and anti-allergic properties of the sesquiterpene polygodial". Life Sciences. 70 (2): 159–169. doi:10.1016/s0024-3205(01)01387-x. PMID   11787941.
  18. ↑ Martin, William John; Herst, Patries M.; Chia, Elizabeth W.; Harper, Jacquie L. (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. doi:10.1016/j.freeradbiomed.2009.05.035. PMID   19500663.
  19. ↑ Kubo, Isao; Fujita, Ken-Ichi; Lee, Sang Hwa; Ha, Tae Joung (2005). "Antibacterial activity of polygodial". Phytotherapy Research. 19 (12): 1013–1017. doi:10.1002/ptr.1777. PMID   16372365. S2CID   30377678.
  20. ↑ Cimino, Guido; De Rosa, Salvatore; De Stefano, Salvatore; Sodano, Guido; Villani, Guido (1983-03-11). "Dorid Nudibranch Elaborates Its Own Chemical Defense". Science. 219 (4589): 1237–1238. doi:10.1126/science.219.4589.1237.
  21. ↑ Kang, Guipeun; Allard, Corey A. H.; Valencia-Montoya, Wendy A.; van Giesen, Lena; Kim, Jeong Joo; Kilian, Peter B.; Bai, Xiaochen; Bellono, Nicholas W.; Hibbs, Ryan E. (2023-04-12). "Sensory specializations drive octopus and squid behaviour". Nature. 616 (7956): 378–383. doi:10.1038/s41586-023-05808-z. ISSN   1476-4687.
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