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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Related Research Articles

<i>Pseudowintera</i> Genus of trees

Pseudowintera is a genus of woody evergreen flowering trees and shrubs, part of family Winteraceae. The species of Pseudowintera are native to New Zealand. Winteraceae are magnoliids, associated with the humid Antarctic flora of the southern hemisphere. Horopito can be chewed for a hot, peppery taste.

<span class="mw-page-title-main">Linalool</span> Chemical compound with a floral aroma

Linalool refers to two enantiomers of a naturally occurring terpene alcohol found in many flowers and spice plants. Linalool has multiple commercial applications, the majority of which are based on its pleasant scent. A colorless oil, linalool is classified as an acyclic monoterpenoid. In plants, it is a metabolite, a volatile oil component, an antimicrobial agent, and an aroma compound. Linalool has uses in manufacturing of soaps, fragrances, food additives as flavors, household products, and insecticides. Esters of linalool are referred to as linalyl, e.g. linalyl pyrophosphate, an isomer of geranyl pyrophosphate.

<span class="mw-page-title-main">Caryophyllene</span> Chemical compound

Caryophyllene, more formally (−)-β-caryophyllene,(BCP), is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of Cannabis sativa, rosemary, and hops. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature.

The name Catuaba is used for the infusions of the bark of a number of trees native to Brazil. The most widely used barks are derived from the trees Trichilia catigua and Erythroxylum vaccinifolium. Other catuaba preparations use the bark of trees from the following genera or families: Anemopaegma, Ilex, Micropholis, Phyllanthus, Secondatia, Tetragastris and species from the Myrtaceae.

<span class="mw-page-title-main">Voacangine</span> Chemical compound

Voacangine is an alkaloid found predominantly in the root bark of the Voacanga africana tree, as well as in other plants such as Tabernanthe iboga, Tabernaemontana africana, Trachelospermum jasminoides, Tabernaemontana divaricata and Ervatamia yunnanensis. It is an iboga alkaloid which commonly serves as a precursor for the semi-synthesis of ibogaine. It has been demonstrated in animals to have similar anti-addictive properties to ibogaine itself. It also potentiates the effects of barbiturates. Under UV-A and UV-B light its crystals fluoresce blue-green, and it is soluble in ethanol.

<span class="mw-page-title-main">Triterpene</span> Class of chemical compounds

Triterpenes are a class of terpenes composed of six isoprene units with the molecular formula C30H48; they may also be thought of as consisting of three terpene units. Animals, plants and fungi all produce triterpenes, including squalene, the precursor to all steroids.

<span class="mw-page-title-main">Helenalin</span> Chemical compound

Helenalin, or (-)-4-Hydroxy-4a,8-dimethyl-3,3a,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione, is a toxic sesquiterpene lactone which can be found in several plants such as Arnica montana and Arnica chamissonis Helenalin is responsible for the toxicity of the Arnica spp. Although toxic, helenalin possesses some in vitro anti-inflammatory and anti-neoplastic effects. Helenalin can inhibit certain enzymes, such as 5-lipoxygenase and leukotriene C4 synthase. For this reason the compound or its derivatives may have potential medical applications.

<i>Drimys winteri</i> Species of tree from South America

Drimys winteri, the winter's bark or canelo, is a slender tree in the family Winteraceae, growing up to 20 m (66 ft) tall. It is native to the Magellanic and Valdivian temperate forests of Chile and Argentina, where it is a dominant tree in the coastal evergreen forests. It is found below 1,200 m (3,900 ft) between latitude 32° south and Cape Horn at latitude 56°. In its southernmost natural range it can tolerate temperatures down to −20 °C (−4 °F). The plant is renowned for its phenotypic plasticity being able to grow in different sites from "extreme arid zones to wetlands along Chile". The tree does also grow in places with various types and degrees of competition from other plants.

<span class="mw-page-title-main">Hodgkinsine</span> Chemical compound

Hodgkinsine is an alkaloid found in plants of the genus Psychotria, particularly Psychotria colorata, although it is also found in Psychotria lyciiflora and probably other species in this family,

<span class="mw-page-title-main">Astilbin</span> Chemical compound

Astilbin is a flavanonol, a type of flavonoid. Astilbin is the (2R-trans)-isomer; neoisoastilbin is the (2S-cis)-isomer and isoastilbin is the (2R-cis)-isomer.

<span class="mw-page-title-main">Jatrorrhizine</span> Chemical compound

Jatrorrhizine is a protoberberine alkaloid found in some plant species, such as Enantia chlorantha (Annonaceae). Synonyms that may be encountered include jateorrhizine, neprotin, jatrochizine, jatrorhizine, and yatrorizine.

<span class="mw-page-title-main">Matrine</span> Chemical compound

Matrine is an alkaloid found in plants from the genus Sophora. It has a variety of pharmacological effects, including anti-cancer effects, as well as κ-opioid and μ-opioid receptor agonism.

<i>Quercus infectoria</i> Species of oak tree

Quercus infectoria or the Aleppo oak is a species of oak well known for producing galls that have been traditionally used for centuries in Asia medicinally while also used in softening leather and in making black dye and ink.

<i>Croton lechleri</i> Species of plant

Croton lechleri is a species of flowering plant in the spurge family, Euphorbiaceae, that is native to northwestern South America. It is commonly known as sangre de grado, sangre de drago or sangre de grada. They refer to this tree's thick red latex.

<span class="mw-page-title-main">Velleral</span> Chemical compound

Velleral (2,2,8-trimethyl-3,3a,8,8a-tetrahydro-1H-azulene-5,6-dicarbaldehyde) is a sesquiterpene dialdehyde found in certain mushrooms, like Lactarius torminosus and Lactarius vellereus, after which it was named. The compound is thought to be part of a chemical defense system that protects the mushrooms against predation. First isolated in 1969, and characterized structurally in 1973, velleral has antimicrobial activity. Several syntheses have been devised.

<i>Piper marginatum</i> Species of flowering plant

Piper marginatum, the cake bush, Anesi wiwiri, marigold pepper, Ti Bombé in Creole or Hinojo, is a plant species in the genus Piper found in moist, shady spots in the Amazon rainforest in Surinam, French Guiana and Brazil.

Psilostachyins are group of chemical compounds isolated from Ambrosia psilostachya.

<i>Sarcococca saligna</i> Species of flowering plant

Sarcococca saligna, the sweet box or Christmas box, is a species of flowering plant in the family Buxaceae. This shrub is native to northern Pakistan. Its common name in Pakistan is sheha.

<span class="mw-page-title-main">Drimane</span> Chemical compound

Drimane is a bicyclic sesquiterpene. It is the parent structure of many natural products with various biological activity.

<span class="mw-page-title-main">Filicin</span> Chemical compound

Filicin is a chemical compound that has been isolated from ferns of the genus Dryopteris. It has been isolated from the male fern. Filicin has been studied for its anthelmintic activity.

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. 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. 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.
  7. 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.
  8. 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.
  9. 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.
  10. 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.
  11. 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.
  12. 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.
  13. 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. doi:10.1016/s0031-9422(00)00515-x. PMID   11336250.
  14. 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.
  15. 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.
  16. 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.
  17. 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.
  18. 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.