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Phytoalexin

From Wikipedia, the free encyclopedia
Class of chemical compounds
Capsidiol is a phytoalexin produced by certain plants in response to pathogenic attack.

Phytoalexins areantimicrobial substances, some of which areantioxidative as well. They are defined not by their having any particular chemical structure or character, but by the fact that they are defensively synthesizedde novo byplants that produce the compounds rapidly at sites of pathogen infection. In general phytoalexins are broad spectrum inhibitors; they are chemically diverse, and different chemical classes of compounds are characteristic of particular planttaxa. Phytoalexins tend to fall into several chemical classes, includingterpenoids,glycosteroids, andalkaloids; however, the term applies to anyphytochemicals that are induced by microbial infection.

Function

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Phytoalexins are produced in plants to act as toxins to the attacking organism. They may puncture thecell wall, delay maturation, disrupt metabolism or prevent reproduction of the pathogen in question. Their importance in plant defense is indicated by an increase in susceptibility of plant tissue to infection when phytoalexin biosynthesis is inhibited. Mutants incapable of phytoalexin production exhibit more extensive pathogen colonization as compared to wild types. As such, host-specific pathogens capable of degrading phytoalexins are more virulent than those unable to do so.[1]

When a plant cell recognizes particles from damagedcells or particles from the pathogen, the plant launches a two-pronged resistance: a general short-term response and a delayed long-term specific response.[citation needed]

As part of the induced resistance, the short-term response, the plant deploysreactive oxygen species such assuperoxide andhydrogen peroxide to kill invading cells. In pathogen interactions, the common short-term response is thehypersensitive response, in which cells surrounding the site of infection are signaled to undergoapoptosis, or programmed cell death, in order to prevent the spread of the pathogen to the rest of the plant.[citation needed]

Long-term resistance, orsystemic acquired resistance (SAR), involves communication of the damaged tissue with the rest of the plant usingplant hormones such asjasmonic acid,ethylene,abscisic acid, orsalicylic acid. The reception of the signal leads to global changes within the plant, which induce expression of genes that protect from further pathogen intrusion, including enzymes involved in the production of phytoalexins. Often, if jasmonates or ethylene (both gaseous hormones) are released from the wounded tissue, neighboring plants also manufacture phytoalexins in response. For herbivores, commonvectors forplant diseases, these and other wound response aromatics seem to act as a warning that the plant is no longer edible.[citation needed] Also, in accordance with the old adage, "an enemy of my enemy is my friend", the aromatics may alert natural enemies of the plant invaders to the presence thereof.

Recent research

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Allixin (3-hydroxy-5-methoxy-6-methyl-2-pentyl-4H-pyran-4-one), a non-sulfur-containing compound having aγ-pyrone skeletal structure, was the first compound isolated fromgarlic as a phytoalexin, a product induced in plants by continuousstress.[2] This compound has been shown to have unique biological properties, such as anti-oxidative effects,[2] anti-microbial effects,[2] anti-tumor promoting effects,[3] inhibition ofaflatoxin B2DNA binding,[4] and neurotrophic effects.[4] Allixin showed an anti-tumor promoting effect in vivo, inhibiting skintumor formation byTPA inDMBA initiated mice.[3] Herein, allixin and/or its analogs may be expected to be useful compounds for cancer prevention or chemotherapy agents for other diseases.[citation needed]

Role of natural phenols in the plant defense against fungal pathogens

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Polyphenols, especiallyisoflavonoids and related substances, play a role in the plant defense against fungal and other microbial pathogens.

InVitis vinifera grape,trans-resveratrol is a phytoalexin produced against the growth of fungal pathogens such asBotrytis cinerea[5] anddelta-viniferin is another grapevine phytoalexin produced followingfungal infection byPlasmopara viticola.[6]Pinosylvin is a pre-infectiousstilbenoid toxin (i.e. synthesized prior to infection), contrary to phytoalexins which are synthesized during infection. It is present in theheartwood ofPinaceae.[7] It is a fungitoxin protecting the wood fromfungal infection.[8]

Sakuranetin is aflavanone, a type of flavonoid. It can be found inPolymnia fruticosa[9] andrice, where it acts as a phytoalexin against spore germination ofPyricularia oryzae.[10] InSorghum, theSbF3'H2 gene, encoding aflavonoid 3'-hydroxylase, seems to be expressed inpathogen-specific3-deoxyanthocyanidin phytoalexin synthesis,[11] for example inSorghum-Colletotrichum interactions.[12]

6-Methoxymellein is adihydroisocoumarin and a phytoalexin induced in carrot slices byUV-C,[13] that allows resistance toBotrytis cinerea[14] and othermicroorganisms.[15]

Danielone is a phytoalexin found in thepapaya fruit. This compound showed high antifungal activity againstColletotrichum gloesporioides, a pathogenic fungus of papaya.[16]

Stilbenes are produced inEucalyptus sideroxylon in case of pathogen attacks. Such compounds can be implied in thehypersensitive response of plants. High levels ofpolyphenols in some woods can explain their naturalpreservation against rot.[17]

Avenanthramides are phytoalexins produced byAvena sativa in its response toPuccinia coronata var.avenae f. sp.avenae, the oat crownrust.[18][19] (Avenanthramides were formerly called avenalumins.)[20]

See also

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References

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  1. ^Glazebrook, J; Ausubel, F M (1994)."Isolation of phytoalexin-deficient mutants of Arabidopsis thaliana and characterization of their interactions with bacterial pathogens".PNAS.91 (19):8955–8959.Bibcode:1994PNAS...91.8955G.doi:10.1073/pnas.91.19.8955.PMC 44725.PMID 8090752.
  2. ^abcKodera Y, Matuura H, Yoshida S, Sumida T, Itakura Y, Fuwa T, Nishino H (1989)."Allixin, a stress compound from garlic".Chem. Pharm. Bull.37 (6):1656–1658.doi:10.1248/cpb.37.1656.
  3. ^abNishino H, Nishino A, Takayama J, Iwashima A, Itakura Y, Kodera Y, Matsuura H, Fuwa T (1990). "Antitumor promoting activity of allixin, a stress compound produced by garlic".Cancer J.3:20–21.
  4. ^abYamasaki T.; Teel R. W.; Lau B. H. S. (1991). "Effect of allixin, a phytoalexin produced by garlic, on mutagenesis, DNA-binding and metabolism of aflatoxin B1".Cancer Lett.59 (2):89–94.doi:10.1016/0304-3835(91)90171-D.PMID 1909211.
  5. ^F. Favaron; M. Lucchetta; S. Odorizzi; A.T. Pais da Cunha; L. Sella (2009)."The role of grape polyphenols on trans-resveratrol activity againstBotrytis cinerea and of fungal laccase on the solubility of putative grape PR proteins"(PDF).Journal of Plant Pathology.91 (3):579–588. Retrieved2011-01-22.
  6. ^Timperio, Anna Maria; d’Alessandro, Angelo; Fagioni, Marco; Magro, Paolo; Zolla, Lello (2012). "Production of the phytoalexins trans-resveratrol and delta-viniferin in two economy-relevant grape cultivars upon infection withBotrytis cinerea in field conditions".Plant Physiology and Biochemistry.50 (1):65–71.doi:10.1016/j.plaphy.2011.07.008.PMID 21821423.
  7. ^Hovelstad, Hanne; Leirset, Ingebjorg; Oyaas, Karin; Fiksdahl, Anne (2006)."Screening Analyses of Pinosylvin Stilbenes, Resin Acids and Lignans in Norwegian Conifers".Molecules.11 (1):103–14.doi:10.3390/11010103.PMC 6148674.PMID 17962750.
  8. ^Lee, S.K.; Lee, H.J.; Min, H.Y.; Park, E.J.; Lee, K.M.; Ahn, Y.H.; Cho, Y.J.; Pyee, J.H. (2005). "Antibacterial and antifungal activity of pinosylvin, a constituent of pine".Fitoterapia.76 (2):258–60.doi:10.1016/j.fitote.2004.12.004.PMID 15752644.
  9. ^"Structure and Data for Sakuranetin (NSC 407228)".home.ncifcrf.gov. Archived fromthe original on 2018-12-03. Retrieved2012-04-13.
  10. ^Kodama, Osamu; Miyakawa, Junichi; Akatsuka, Tadami; Kiyosawa, Shigehisa (1992). "Sakuranetin, a flavanone phytoalexin from ultraviolet-irradiated rice leaves".Phytochemistry.31 (11):3807–3809.Bibcode:1992PChem..31.3807K.doi:10.1016/S0031-9422(00)97532-0.
  11. ^Chun-Hat Shih; Ivan K. Chu; Wing Kin Yip; Clive Lo (2006)."Differential Expression of Two Flavonoid 3'-Hydroxylase cDNAs Involved in Biosynthesis of Anthocyanin Pigments and 3-Deoxyanthocyanidin Phytoalexins in Sorghum".Plant and Cell Physiology.47 (10):1412–1419.doi:10.1093/pcp/pcl003.PMID 16943219.
  12. ^Chopra, Surinder; Gaffoor, Iffa; Ibraheem, Farag."Biosynthesis and regulation of 3-deoxyanthocyanidin phytoalexins induced during Sorghum-Colletotrichum interaction: Heterologous expression in maize". Archived fromthe original on 2011-07-25.
  13. ^Mercier, J.; Arul, J.; Ponnampalam, R.; Boulet, M. (1993). "Induction of 6-Methoxymellein and Resistance to Storage Pathogens in Carrot Slices by UV-C".Journal of Phytopathology.137:44–54.doi:10.1111/j.1439-0434.1993.tb01324.x.
  14. ^Hoffman, R.; Heale, J.B. (1987). "Cell death, 6-methoxymellein accumulation, and induced resistance toBotrytis cinerea in carrot root slices".Physiological and Molecular Plant Pathology.30:67–75.doi:10.1016/0885-5765(87)90083-X.
  15. ^Kurosaki, Fumiya; Nishi, Arasuke (1983). "Isolation and antimicrobial activity of the phytoalexin 6-methoxymellein from cultured carrot cells".Phytochemistry.22 (3): 669.Bibcode:1983PChem..22..669K.doi:10.1016/S0031-9422(00)86959-9.
  16. ^Echeverri, Fernando; Torres, Fernando; Quiñones, Winston; Cardona, Gloria; Archbold, Rosendo; Roldan, Javier; Brito, Ivan; Luis, Javier G.; Lahlou, El-Hassane (1997). "Danielone, a phytoalexin from papaya fruit".Phytochemistry.44 (2):255–256.Bibcode:1997PChem..44..255E.doi:10.1016/S0031-9422(96)00418-9.PMID 9004541.
  17. ^Hart, John H.; Hillis, W. E. (1974). "Inhibition of wood-rotting fungi by stilbenes and other polyphenols inEucalyptus sideroxylon".Phytopathology.64 (7):939–48.doi:10.1094/Phyto-64-939.
  18. ^Mayama, S.; Bordin, A.P.A.; Morikawa, T.; Tanpo, H.; Kato, H. (1995). "Association of avenalumin accumulation with co-segregation of victorin sensitivity and crown rust resistance in oat lines carrying thePc-2 gene".Physiological and Molecular Plant Pathology.46 (4):263–274.doi:10.1006/pmpp.1995.1021.S2CID 82948086.
  19. ^Mayama, S.; Matsuura, Y.; Iida, H.; Tani, T. (1982). "The role of avenalumin in the resistance of oat to crown rust,Puccinia coronata f. sp.avenae".Physiological Plant Pathology.20 (2):189–199.doi:10.1016/0048-4059(82)90084-4.
  20. ^Hammerschmidt, Ray (1999). "Phytoalexins: What Have We Learned After 60 Years?".Annual Review of Phytopathology.37 (1):285–306.doi:10.1146/annurev.phyto.37.1.285.PMID 11701825.

Further reading

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External links

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