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|ImageFile=Polygodial.svg |
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| verifiedrevid = 417596292 |
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|IUPACName= <small>(1''R'',4a''S'',8a''S'')-5,5,8a-Trimethyl-1,4,4a,6,7,8-<br>hexahydronaphthalene-1,2-dicarboxaldehyde</small> |
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| ImageFile=Polygodial.svg |
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|OtherNames=Poligodial, Tadeodal, Tadeonal, Drim-7-ene-11,12-dial |
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| ImageSize=180px |
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|Section1= {{Chembox Identifiers |
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| IUPACName = Drim-7-ene-11,12-dial |
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| CASNo=6754-20-7 |
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| SystematicName = (1''R'',4a''S'',8a''S'')-5,5,8a-Trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalene-1,2-dicarbaldehyde |
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| PubChem=72503 |
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| OtherNames = Poligodial; Tadeodal; Tadeonal |
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| SMILES=CC1(CCC2(1CC=C(2C=O)C=O)C)C |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=6754-20-7 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 5FAF7T66M7 |
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| PubChem=72503 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 254550 |
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| SMILES=CC1(CCC2(1CC=C(2C=O)C=O)C)C |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 65414 |
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| 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 |
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| InChIKey = AZJUJOFIHHNCSV-KCQAQPDRBV |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 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 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = AZJUJOFIHHNCSV-KCQAQPDRSA-N |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=15 | H=22 | O=2 |
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| Formula=C<sub>15</sub>H<sub>22</sub>O<sub>2</sub> |
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| MolarMass=234.33398 |
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|Section3= {{Chembox Hazards |
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'''Polygodial''' is an active constituent of ], ], ], ], ] and ].<ref>Beattie, G.A.C., ''Spray Oils Beyond 2000'', University of Western Queensland, ISBN 1-86341-902-0</ref><ref>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.</ref><ref>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</ref><ref name=jonasshon-1996>M Jonassohn (1996)Sesquiterpenoid unsaturated dialdehydes - Structural properties that affect reactivity and bioctivity. Doctoral thesis, Lund University, Sweden. ISBN 91-628-2215-2. {{PDF|730 ]<!-- application/pdf, 747998 bytes -->}}</ref> |
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'''Polygodial''' is ] found in ], ], ], ], ], ], and ''] limbata''.<ref>Beattie, G.A.C., ''Spray Oils Beyond 2000'', University of Western Queensland, {{ISBN|1-86341-902-0}}</ref><ref>{{Cite journal | doi = 10.1055/s-2007-971422 | pmid = 7089094 | title = Antibiotic Substances from New Zealand Plants | journal = Planta Medica | volume = 44 | issue = 3 | pages = 134–138 | year = 1982 | last1 = McCallion | first1 = Rosemary | last2 = Cole | first2 = A. | last3 = Walker | first3 = J. | last4 = Blunt | first4 = J. | last5 = Munro | first5 = M. }}</ref><ref>{{Cite journal | doi = 10.1016/j.bse.2006.10.019 | title = Presence of polygodial and drimenol in Drimys populations from Chile | journal = Biochemical Systematics and Ecology | volume = 35 | issue = 7 | pages = 434–438 | year = 2007 | last1 = Muñoz-Concha | first1 = Diego | last2 = Vogel | first2 = Hermine | last3 = Yunes | first3 = Rosendo | last4 = Razmilic | first4 = Iván | last5 = Bresciani | first5 = Louisiane | last6 = Malheiros | first6 = Angela | bibcode = 2007BioSE..35..434M }}</ref><ref name=jonasshon-1996> |
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{{cite thesis |
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|last = Jonassohn |
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|first = Mikael |
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|date = 1996 |
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|title = Sesquiterpenoid unsaturated dialdehydes: structural properties that affect reactivity and bioactivity |
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|type = PhD |
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|publisher = ] |
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|isbn = 91-628-2215-2 |
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|url=http://www.organic.lu.se/Publications/Ph.%20D.%20theses/Jonassohn.pdf |access-date=2008-01-30 |url-status=dead |archive-url=https://web.archive.org/web/20111003033550/http://www.organic.lu.se/Publications/Ph.%20D.%20theses/Jonassohn.pdf |archive-date=2011-10-03 }} |
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</ref><ref>{{Cite journal | doi = 10.1126/science.219.4589.1237 | pmid = 17771309 | title = Dorid Nudibranch Elaborates Its Own Chemical Defense | journal = Science | volume = 219 | issue = 4589 | pages = 1237–1238 | year = 1983 | last1 = Cimino | first1 = G. | last2 = De Rosa | first2 = S. | last3 = De Stefano | first3 = S. | last4 = Sodano | first4 = G. | last5 = Villani | first5 = G. | bibcode = 1983Sci...219.1237C | s2cid = 8590649 }}</ref> |
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Chemically it is a drimane-type sesquiterpene dialdehyde of formula C<sub>15</sub>H<sub>22</sub>O<sub>2</sub>. |
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Chemically it is a ]-type ] ] of formula C<sub>15</sub>H<sub>22</sub>O<sub>2</sub>. |
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It elicits a warm and pungent flavour. |
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Polygodial elicits a warm and pungent flavour. |
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The compound activates the ] pain receptor in nerve endings in the mouth that mediate the sensation of pungency.<ref>{{Cite journal |last=Escalera |first=Jasmine |last2=von Hehn |first2=Christian A. |last3=Bessac |first3=Bret F. |last4=Sivula |first4=Michael |last5=Jordt |first5=Sven-Eric |date=2008-10-29 |title=TRPA1 Mediates the Noxious Effects of Natural Sesquiterpene Deterrents |url=https://linkinghub.elsevier.com/retrieve/pii/S0021925819493253 |journal=Journal of Biological Chemistry |language=en |volume=283 |issue=35 |pages=24136–24144 |doi=10.1074/jbc.M710280200 |pmc=2527119 |pmid=18550530 |doi-access=free}}</ref> |
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The biological activity of polygodial has been reported in the scientific literature to include antifungal and ] activities,<ref> 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.</ref> <ref> 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</ref> <ref> Kubo, I., Fujita, K. & Lee, S.H., (2001). Antifungal Mechanism of Polygodial. Journal of Agricultural and Food Chemistry, 49(3), 1607-1611. </ref> antihyperalgesia <ref>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.</ref> , potent attachment-inhibitory activity <ref>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. </ref>, insect antifeedant activity <ref>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. </ref>, antinociception <ref>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. </ref> <ref>Malheiros, A. et al., (2001). A sesquiterpene drimane with antinociceptive activity from Drimys winteri bark. Phytochemistry, 57(1), 103-107. </ref> vasorelaxation action in vessels of rabbit and guinea pig <ref>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. </ref>, ] and ] activities <ref> 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.</ref> <ref>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. </ref> <ref>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. </ref> |
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The '']'' ] of polygodial has been reported in the scientific literature to include antifungal and ] activities,<ref>{{Cite journal | doi = 10.1055/s-2006-960114 | pmid = 1775575 | title = Comparison of the Antimicrobial and Cytotoxic Activities of Twenty Unsaturated Sesquiterpene Dialdehydes from Plants and Mushrooms | journal = Planta Medica | volume = 57 | issue = 4 | pages = 344–346 | year = 1991 | last1 = Anke | first1 = Heidrun | last2 = Sterner | first2 = Olov }}</ref><ref>{{Cite journal | doi = 10.1055/s-1999-13981 | pmid = 10232062 | title = In Vitro Antifungal Susceptibilities of Candida albicans and Other Fungal Pathogens to Polygodial, a Sesquiterpene Dialdehyde | journal = Planta Medica | volume = 65 | issue = 3 | pages = 204–208 | year = 1999 | last1 = Lee | first1 = Sang Hwa | last2 = Lee | first2 = Jae Ran | last3 = Lunde | first3 = Christopher S. | last4 = Kubo | first4 = Isao }}</ref><ref>{{Cite journal | doi = 10.1021/jf000136g | pmid = 11312903 | title = Antifungal Mechanism of Polygodial | journal = Journal of Agricultural and Food Chemistry | volume = 49 | issue = 3 | pages = 1607–1611 | year = 2001 | last1 = Kubo | first1 = Isao | last2 = Fujita | first2 = Ken'Ichi | last3 = Lee | first3 = Sang Hwa }}</ref> antihyperalgesia,<ref>{{Cite journal | doi = 10.1016/s0024-3205(98)00285-9 | pmid = 9714424 | title = Anti-hyperalgesic properties of the extract and of the main sesquiterpene polygodial isolated from the barks of Drymis winteri (Winteraceae) | journal = Life Sciences | volume = 63 | issue = 5 | pages = 369–381 | year = 1998 | last1 = Mendes | first1 = Gilboé L. | last2 = Santos | first2 = Adair R.S. | last3 = Campos | first3 = Maria M. | last4 = Tratsk | first4 = Karla S. | last5 = Yunes | first5 = Rosendo A. | last6 = Filho | first6 = Valdir Cechinel | last7 = Calixto | first7 = Joăo B. }}</ref> potent attachment-inhibitory activity,<ref>{{Cite journal | doi=10.1271/bbb.64.2699 |pmid = 11210140|title = Polygodial, a Potent Attachment-inhibiting Substance for the Blue Mussel,Mytilus edulis galloprovincialisfrom ''Tasmannia'' lanceolata|journal = Bioscience, Biotechnology, and Biochemistry|volume = 64|issue = 12|pages = 2699–2701|year = 2000|last1 = Ban|first1 = Takahiro|last2 = Singh|first2 = Inder Pal|last3 = Etoh|first3 = Hideo|doi-access = free}}</ref> insect antifeedant activity,<ref>{{Cite journal | doi = 10.1021/np50050a002 | pmid = 3655790 | title = Insect Antifeedant Activity and Hot Taste for Humans of Selected Natural and Synthetic 1,4-Dialdehydes | journal = Journal of Natural Products | volume = 50 | issue = 2 | pages = 146–151 | year = 1987 | last1 = Caprioli | first1 = Vincenzo | last2 = Cimino | first2 = Guido | last3 = Colle | first3 = Roberto | last4 = Gavagnin | first4 = Margherita | last5 = Sodano | first5 = Guido | last6 = Spinella | first6 = Aldo }}</ref> ],<ref>{{cite journal | pmid = 10604944 | year = 2000 | last1 = Mendes | first1 = G. L. | title = Assessment of mechanisms involved in antinociception caused by sesquiterpene polygodial | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 292 | issue = 1 | pages = 164–72 | last2 = Santos | first2 = A. R. | last3 = Malheiros | first3 = A. | last4 = Filho | first4 = V. C. | last5 = Yunes | first5 = R. A. | last6 = Calixto | first6 = J. B. }}</ref><ref>{{Cite journal | doi=10.1016/s0031-9422(00)00515-x | pmid=11336250 | title=A sesquiterpene drimane with antinociceptive activity from Drimys winteri bark | journal=Phytochemistry | volume=57 | issue=1 | pages=103–107 | year=2001 | last1=Malheiros | first1=Angela | last2=Filho | first2=Valdir Cechinel | last3=Schmitt | first3=Clarisse B. | last4=Santos | first4=Adair R.S | last5=Scheidt | first5=Cristiano | last6=Calixto | first6=João B. | last7=Monache | first7=Franco Delle | last8=Yunes | first8=Rosendo A. | bibcode=2001PChem..57..103M }}</ref> vasorelaxing action in vessels of rabbit and guinea pig,<ref>{{Cite journal | doi=10.1016/s0014-2999(99)00719-0 |pmid = 10611463|title = Mechanisms underlying the relaxation caused by the sesquiterpene polygodial in vessels from rabbit and guinea-pig|journal = European Journal of Pharmacology|volume = 386|pages = 47–53|year = 1999|last1 = André|first1 = Eunice|last2 = Malheiros|first2 = Ângela|last3 = Cechinel-Filho|first3 = Valdir|last4 = Yunes|first4 = Rosendo A.|last5 = Calixto|first5 = João B.| issue=1 }}</ref> ] and ] activities.<ref>{{Cite journal | doi=10.1007/s000110050234 | pmid=9459082 | title=Anti-allergic effects and oedema inhibition caused by the extract of Drymis winteri | journal=Inflammation Research | volume=46 | issue=12 | pages=509–514 | year=1997 | last1=Tratsk | first1=K. S. | last2=Campos | first2=M. M. | last3=Vaz | first3=Z. R. | last4=Filho | first4=V. C. | last5=Schlemper | first5=V. | last6=Yunes | first6=R. A. | last7=Calixto | first7=J. B. | s2cid=206862953 }}</ref><ref>{{Cite journal | doi=10.1016/s0024-3205(01)01387-x | pmid=11787941 | title=Additional evidence for the anti-inflammatory and anti-allergic properties of the sesquiterpene polygodial | journal=Life Sciences | volume=70 | issue=2 | pages=159–169 | year=2001 | last1=Da Cunha | first1=Fernanda M. | last2=Fröde | first2=Tânia S. | last3=Mendes | first3=Gilboé L. | last4=Malheiros | first4=Angela | last5=Filho | first5=Valdir Cechinel | last6=Yunes | first6=Rosendo A. | last7=Calixto | first7=João B. }}</ref><ref>{{Cite journal | doi=10.1016/j.freeradbiomed.2009.05.035 | title=Sesquiterpene dialdehydes inhibit MSU crystal-induced superoxide production by infiltrating neutrophils in an in vivo model of gouty inflammation | journal=Free Radical Biology and Medicine | volume=47 | issue=5 | pages=616–621 | year=2009 | last1=Martin | first1=William John | last2=Herst | first2=Patries M. | last3=Chia | first3=Elizabeth W. | last4=Harper | first4=Jacquie L. | pmid=19500663 }}</ref> |
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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<ref>Kubo , Fujita K, Lee S H, Ha T J. Antibacterial Activity of Polygodial, Phytotherapy Research, 2005, 19, pp 1013-1017</ref>. |
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Polygodial’s primary antifungal action is as a nonionic ], 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.<ref>{{Cite journal | doi=10.1002/ptr.1777 | title=Antibacterial activity of polygodial | journal=Phytotherapy Research | volume=19 | issue=12 | pages=1013–1017 | year=2005 | last1=Kubo | first1=Isao | last2=Fujita | first2=Ken-Ichi | last3=Lee | first3=Sang Hwa | last4=Ha | first4=Tae Joung | pmid=16372365 | s2cid=30377678 }}</ref> |
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It is also used as an ] for its antifeedant property, which causes insects to starve. |
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It is also an ] with antifeedant properties, which causes insects to starve. |
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== References == |
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== References == |
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{{Transient receptor potential channel modulators}} |
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{{organic-compound-stub}} |
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