Polygodial

Polygodial
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
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 ☒N
    Key: AZJUJOFIHHNCSV-KCQAQPDRSA-N ☒N
  • 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).
☒N verify (what is checkY☒N ?)

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.

References

[edit]
  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.
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