HOME
The Info List - Polygodial





Polygodial
Polygodial
is an active constituent of Dorrigo Pepper, Mountain Pepper, Horopito, Canelo, Paracress and Water-pepper.[1][2][3][4] Furthermore, Polygodial
Polygodial
is synthetized by Dendrodoris
Dendrodoris
limbata.[5] 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,[6][7][8] antihyperalgesia,[9] potent attachment-inhibitory activity,[10] insect antifeedant activity,[11] antinociception[12][13] vasorelaxation 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 used as an insecticide for its antifeedant property, which causes insects to starve. References[edit]

^ Beattie, G.A.C., Spray Oils Beyond 2000, University of Western Queensland, ISBN 1-86341-902-0 ^ McCallion RF, Cole ALJ, Walker JRL, Blunt JW, Munro MHG. Antibiotics substances from New Zealand plants II. Polygodial, an anti-Candida agent from Pseudowintera
Pseudowintera
colorata. Planta Med 1982; 44: 134-138. ^ 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 ^ M Jonassohn (1996)Sesquiterpenoid unsaturated dialdehydes - Structural properties that affect reactivity and bioctivity. Doctoral thesis, Lund University, Sweden. ISBN 91-628-2215-2. "[1]".  External link in title= (help); Missing or empty url= (help)"Archived copy" (PDF). Archived from the original (PDF) on 2011-10-03. Retrieved 2008-01-30.  (730 KiB) ^ Cimino G, DE Rosa S, DE Stefano S, Sodano G, Villani G. Dorid nudibranch elaborates its own chemical defense. Science. 1983; 19(4589):1237-1238. ^ 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. ^ 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
Sesquiterpene
Dialdehyde, Planta Medica, vol 65, pp205-208 ^ Kubo, I., Fujita, K. & Lee, S.H., (2001). Antifungal Mechanism of Polygodial. Journal of Agricultural and Food Chemistry, 49(3), 1607-1611. ^ 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. ^ 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. ^ 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. ^ 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. ^ Malheiros, A. et al., (2001). A sesquiterpene drimane with antinociceptive activity from Drimys winteri
Drimys winteri
bark. Phytochemistry, 57(1), 103-107. ^ 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. ^ 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. ^ 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. ^ Martin, W.J. et al., (2009). Sesquiterpene
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. ^ Kubo , Fujita K, Lee S H, Ha T J. Antibacterial Activity of Polygodial, Phytotherapy Research, 2005, 19, pp 1013-1017

v t e

TRP channel modulators

TRPA

Activators

4-Hydroxynonenal 4-Oxo-2-nonenal 4,5-EET 12S-HpETE 15-Deoxy-Δ12,14-prostaglandin J2 α- Sanshool
Sanshool
(ginger, Sichuan and melegueta peppers) Acrolein Allicin
Allicin
(garlic) Allyl isothiocyanate
Allyl isothiocyanate
(mustard, radish, horseradish, wasabi) AM404 Bradykinin Cannabichromene
Cannabichromene
(cannabis) Cannabidiol
Cannabidiol
(cannabis) Cannabigerol
Cannabigerol
(cannabis) Cinnamaldehyde
Cinnamaldehyde
(cinnamon) CR gas
CR gas
(dibenzoxazepine; DBO) CS gas
CS gas
(2-chlorobenzal malononitrile) Curcumin
Curcumin
(turmeric) Dehydroligustilide (celery) Diallyl disulfide Dicentrine
Dicentrine
( Lindera
Lindera
spp.) Farnesyl thiosalicylic acid Formalin Gingerols (ginger) Hepoxilin A3 Hepoxilin B3 Hydrogen peroxide Icilin Isothiocyanate Ligustilide (celery, Angelica acutiloba) Linalool
Linalool
(Sichuan pepper, thyme) Methylglyoxal Methyl salicylate
Methyl salicylate
(wintergreen) N-Methylmaleimide Nicotine
Nicotine
(tobacco) Oleocanthal
Oleocanthal
(olive oil) Paclitaxel
Paclitaxel
(Pacific yew) Paracetamol
Paracetamol
(acetaminophen) PF-4840154 Phenacyl chloride Polygodial
Polygodial
(Dorrigo pepper) Shogaols (ginger, Sichuan and melegueta peppers) Tear gases Tetrahydrocannabinol
Tetrahydrocannabinol
(cannabis) Thiopropanal S-oxide
Thiopropanal S-oxide
(onion) Umbellulone
Umbellulone
(Umbellularia californica) WIN 55,212-2

Blockers

Dehydroligustilide (celery) Nicotine
Nicotine
(tobacco) Ruthenium red

TRPC

Activators

Adhyperforin
Adhyperforin
(St John's wort) Diacyl glycerol GSK1702934A Hyperforin
Hyperforin
(St John's wort) Substance P

Blockers

DCDPC DHEA-S Flufenamic acid GSK417651A GSK2293017A Meclofenamic acid N-(p-amylcinnamoyl)anthranilic acid Niflumic acid Pregnenolone sulfate Progesterone Pyr3 Tolfenamic acid

TRPM

Activators

ADP-ribose BCTC Calcium
Calcium
(intracellular) Cold Coolact P Cooling Agent 10 CPS-369 Eucalyptol
Eucalyptol
(eucalyptus) Frescolat MGA Frescolat ML Geraniol Hydroxycitronellal Icilin Linalool Menthol
Menthol
(mint) PMD 38 Pregnenolone sulfate Rutamarin (Ruta graveolens) Steviol glycosides (e.g., stevioside) (Stevia rebaudiana) Sweet tastants (e.g., glucose, fructose, sucrose; indirectly) Thio-BCTC WS-3 WS-12 WS-23

Blockers

Capsazepine Clotrimazole DCDPC Flufenamic acid Meclofenamic acid Mefenamic acid N-(p-amylcinnamoyl)anthranilic acid Nicotine
Nicotine
(tobacco) Niflumic acid Ruthenium red Rutamarin (Ruta graveolens) Tolfenamic acid TPPO

TRPML

Activators

MK6-83 PI(3,5)P2 SF-22

TRPP

Activators

Triptolide
Triptolide
(Tripterygium wilfordii)

Blockers

Ruthenium red

TRPV

Activators

2-APB 5',6'-EET 9-HODE 9-oxoODE 12S-HETE 12S-HpETE 13-HODE 13-oxoODE 20-HETE α- Sanshool
Sanshool
(ginger, Sichuan and melegueta peppers) Allicin
Allicin
(garlic) AM404 Anandamide Bisandrographolide (Andrographis paniculata) Camphor
Camphor
(camphor laurel, rosemary, camphorweed, African blue basil, camphor basil) Cannabidiol
Cannabidiol
(cannabis) Cannabidivarin
Cannabidivarin
(cannabis) Capsaicin
Capsaicin
(chili pepper) Carvacrol
Carvacrol
(oregano, thyme, pepperwort, wild bergamot, others) DHEA Diacyl glycerol Dihydrocapsaicin
Dihydrocapsaicin
(chili pepper) Estradiol Eugenol
Eugenol
(basil, clove) Evodiamine
Evodiamine
(Euodia ruticarpa) Gingerols (ginger) GSK1016790A Heat Hepoxilin A3 Hepoxilin B3 Homocapsaicin
Homocapsaicin
(chili pepper) Homodihydrocapsaicin
Homodihydrocapsaicin
(chili pepper) Incensole
Incensole
(incense) Lysophosphatidic acid Low pH (acidic conditions) Menthol
Menthol
(mint) N-Arachidonoyl dopamine N-Oleoyldopamine N-Oleoylethanolamide Nonivamide
Nonivamide
(PAVA) (PAVA spray) Nordihydrocapsaicin
Nordihydrocapsaicin
(chili pepper) Paclitaxel
Paclitaxel
(Pacific yew) Paracetamol
Paracetamol
(acetaminophen) Phorbol esters
Phorbol esters
(e.g., 4α-PDD) Piperine
Piperine
(black pepper, long pepper) Polygodial
Polygodial
(Dorrigo pepper) Probenecid Protons RhTx Rutamarin (Ruta graveolens) Resiniferatoxin
Resiniferatoxin
(RTX) (Euphorbia resinifera/pooissonii) Shogaols (ginger, Sichuan and melegueta peppers) Tetrahydrocannabivarin
Tetrahydrocannabivarin
(cannabis) Thymol
Thymol
(thyme, oregano) Tinyatoxin
Tinyatoxin
(Euphorbia resinifera/pooissonii) Tramadol Vanillin
Vanillin
(vanilla) Zucapsaicin

Blockers

α- Spinasterol
Spinasterol
( Vernonia
Vernonia
tweediana) AMG-517 Asivatrep BCTC Cannabigerol
Cannabigerol
(cannabis) Cannabigerolic acid (cannabis) Cannabigerovarin (cannabis) Cannabinol
Cannabinol
(cannabis) Capsazepine DCDPC DHEA DHEA-S Flufenamic acid GRC-6211 HC-067047 Lanthanum Meclofenamic acid N-(p-amylcinnamoyl)anthranilic acid NGD-8243 Niflumic acid Pregnenolone sulfate RN-1734 RN-9893 Ruthenium red SB-705498 Tivanisiran Tolfenamic acid

See also: Receptor/signaling modulators • Ion channe

.