Polygodial Explained

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.

It elicits a warm and pungent flavour.

The in vitro biological activity of polygodial has been reported in the scientific literature to include antifungal and antimicrobial activities,[6] [7] [8] antihyperalgesia,[9] potent attachment-inhibitory activity,[10] insect antifeedant activity,[11] antinociception,[12] [13] vasorelaxing action in vessels of rabbit and guinea pig,[14] anti-inflammatory and antiallergic activities.[15] [16] [17]

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.[18]

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

References

  1. Beattie, G.A.C., Spray Oils Beyond 2000, University of Western Queensland,
  2. 10.1055/s-2007-971422 . 7089094 . Antibiotic Substances from New Zealand Plants . Planta Medica . 44 . 3 . 134–138 . 1982 . McCallion . Rosemary . Cole . A. . Walker . J. . Blunt . J. . Munro . M. .
  3. 10.1016/j.bse.2006.10.019 . Presence of polygodial and drimenol in Drimys populations from Chile . Biochemical Systematics and Ecology . 35 . 7 . 434–438 . 2007 . Muñoz-Concha . Diego . Vogel . Hermine . Yunes . Rosendo . Razmilic . Iván . Bresciani . Louisiane . Malheiros . Angela . 2007BioSE..35..434M .
  4. Jonassohn. Mikael. 1996. Sesquiterpenoid unsaturated dialdehydes: structural properties that affect reactivity and bioactivity. PhD. Lund University. 91-628-2215-2. 2008-01-30 . dead . https://web.archive.org/web/20111003033550/http://www.organic.lu.se/Publications/Ph.%20D.%20theses/Jonassohn.pdf . 2011-10-03 .
  5. 10.1126/science.219.4589.1237 . 17771309 . Dorid Nudibranch Elaborates Its Own Chemical Defense . Science . 219 . 4589 . 1237–1238 . 1983 . Cimino . G. . De Rosa . S. . De Stefano . S. . Sodano . G. . Villani . G. . 1983Sci...219.1237C . 8590649 .
  6. 10.1055/s-2006-960114 . 1775575 . Comparison of the Antimicrobial and Cytotoxic Activities of Twenty Unsaturated Sesquiterpene Dialdehydes from Plants and Mushrooms . Planta Medica . 57 . 4 . 344–346 . 1991 . Anke . Heidrun . Sterner . Olov .
  7. 10.1055/s-1999-13981 . 10232062 . In Vitro Antifungal Susceptibilities of Candida albicans and Other Fungal Pathogens to Polygodial, a Sesquiterpene Dialdehyde . Planta Medica . 65 . 3 . 204–208 . 1999 . Lee . Sang Hwa . Lee . Jae Ran . Lunde . Christopher S. . Kubo . Isao .
  8. 10.1021/jf000136g . 11312903 . Antifungal Mechanism of Polygodial . Journal of Agricultural and Food Chemistry . 49 . 3 . 1607–1611 . 2001 . Kubo . Isao . Fujita . Ken'Ichi . Lee . Sang Hwa .
  9. 10.1016/s0024-3205(98)00285-9 . 9714424 . 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 . 1998 . Mendes . Gilboé L. . Santos . Adair R.S. . Campos . Maria M. . Tratsk . Karla S. . Yunes . Rosendo A. . Filho . Valdir Cechinel . Calixto . Joăo B. .
  10. 10.1271/bbb.64.2699 . 11210140. Polygodial, a Potent Attachment-inhibiting Substance for the Blue Mussel,Mytilus edulis galloprovincialisfrom Tasmannia lanceolata. Bioscience, Biotechnology, and Biochemistry. 64. 12. 2699–2701. 2000. Ban. Takahiro. Singh. Inder Pal. Etoh. Hideo. free.
  11. 10.1021/np50050a002 . 3655790 . Insect Antifeedant Activity and Hot Taste for Humans of Selected Natural and Synthetic 1,4-Dialdehydes . Journal of Natural Products . 50 . 2 . 146–151 . 1987 . Caprioli . Vincenzo . Cimino . Guido . Colle . Roberto . Gavagnin . Margherita . Sodano . Guido . Spinella . Aldo .
  12. 10604944 . 2000 . Mendes . G. L. . Assessment of mechanisms involved in antinociception caused by sesquiterpene polygodial . The Journal of Pharmacology and Experimental Therapeutics . 292 . 1 . 164–72 . Santos . A. R. . Malheiros . A. . Filho . V. C. . Yunes . R. A. . Calixto . J. B. .
  13. 10.1016/s0031-9422(00)00515-x . 11336250 . A sesquiterpene drimane with antinociceptive activity from Drimys winteri bark . Phytochemistry . 57 . 1 . 103–107 . 2001 . Malheiros . Angela . Filho . Valdir Cechinel . Schmitt . Clarisse B. . Santos . Adair R.S . Scheidt . Cristiano . Calixto . João B. . Monache . Franco Delle . Yunes . Rosendo A. . 2001PChem..57..103M .
  14. 10.1016/s0014-2999(99)00719-0 . 10611463. Mechanisms underlying the relaxation caused by the sesquiterpene polygodial in vessels from rabbit and guinea-pig. European Journal of Pharmacology. 386. 47–53. 1999. André. Eunice. Malheiros. Ângela. Cechinel-Filho. Valdir. Yunes. Rosendo A.. Calixto. João B.. 1 .
  15. 10.1007/s000110050234 . 9459082 . Anti-allergic effects and oedema inhibition caused by the extract of Drymis winteri . Inflammation Research . 46 . 12 . 509–514 . 1997 . Tratsk . K. S. . Campos . M. M. . Vaz . Z. R. . Filho . V. C. . Schlemper . V. . Yunes . R. A. . Calixto . J. B. . 206862953 .
  16. 10.1016/s0024-3205(01)01387-x . 11787941 . Additional evidence for the anti-inflammatory and anti-allergic properties of the sesquiterpene polygodial . Life Sciences . 70 . 2 . 159–169 . 2001 . Da Cunha . Fernanda M. . Fröde . Tânia S. . Mendes . Gilboé L. . Malheiros . Angela . Filho . Valdir Cechinel . Yunes . Rosendo A. . Calixto . João B. .
  17. 10.1016/j.freeradbiomed.2009.05.035 . 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 . 2009 . Martin . William John . Herst . Patries M. . Chia . Elizabeth W. . Harper . Jacquie L. . 19500663 .
  18. 10.1002/ptr.1777 . Antibacterial activity of polygodial . Phytotherapy Research . 19 . 12 . 1013–1017 . 2005 . Kubo . Isao . Fujita . Ken-Ichi . Lee . Sang Hwa . Ha . Tae Joung . 16372365 . 30377678 .

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