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Phytoalexin
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<h2 id="function">Function</h2> <p>Phytoalexins are produced in plants to act as toxins to the attacking organism. They may puncture the <a href="/facts/Cell_wall/DYXJVrnw">cell wall</a>, 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.<a class="footnote-ref" id="fnref:1" href="#fn:1"><sup>1</sup></a> </p><p>When a plant cell recognizes particles from damaged <a href="/facts/Cell_(biology)/bLM9UQvy">cells</a> or particles from the pathogen, the plant launches a two-pronged resistance: a general short-term response and a delayed long-term specific response. </p><p>As part of the induced resistance, the short-term response, the plant deploys <a href="/facts/Reactive_oxygen_species/GpwSRugH">reactive oxygen species</a> such as <a href="/facts/Superoxide/2X2sQocn">superoxide</a> and <a href="/facts/Hydrogen_peroxide/vju6HBIc">hydrogen peroxide</a> to kill invading cells. In pathogen interactions, the common short-term response is the <a href="/facts/Hypersensitive_response/q1FDzzeP">hypersensitive response</a>, in which cells surrounding the site of infection are signaled to undergo <a href="/facts/Apoptosis/8dVzSm4y">apoptosis</a>, or programmed cell death, in order to prevent the spread of the pathogen to the rest of the plant. </p><p>Long-term resistance, or <a href="/facts/Systemic_acquired_resistance/DkKx6kLa">systemic acquired resistance</a> (SAR), involves communication of the damaged tissue with the rest of the plant using <a href="/facts/Plant_hormone/h3noouev">plant hormones</a> such as <a href="/facts/Jasmonic_acid/CMJKeo73">jasmonic acid</a>, <a href="/facts/Ethylene/QMNBYLYn">ethylene</a>, <a href="/facts/Abscisic_acid/mlkdBKLD">abscisic acid</a>, or <a href="/facts/Salicylic_acid/qz7RRQCR">salicylic acid</a>. 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, common <a href="/facts/Disease_vector/bepASE2M">vectors</a> for <a href="/facts/Plant_disease/h6DTufWF">plant diseases</a>, these and other wound response aromatics seem to act as a warning that the plant is no longer edible. 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. </p> <h2 id="recent-research">Recent research</h2> <p><a href="/facts/Allixin/jsvj07oL">Allixin</a> (3-hydroxy-5-methoxy-6-methyl-2-pentyl-4<i>H</i>-pyran-4-one), a non-sulfur-containing compound having a <a href="/facts/Pyrone/gp3yTctd">γ-pyrone</a> skeletal structure, was the first compound isolated from <a href="/facts/Garlic/NschLR1S">garlic</a> as a phytoalexin, a product induced in plants by continuous <a href="/facts/Stress_(mechanics)/ErAXDbbd">stress</a>.<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a> This compound has been shown to have unique biological properties, such as anti-oxidative effects,<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> anti-microbial effects,<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> anti-tumor promoting effects,<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> inhibition of <a href="/facts/Aflatoxin/EUu21Ywp">aflatoxin</a> B2 <a href="/facts/DNA/nB89Iauz">DNA</a> binding,<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> and neurotrophic effects.<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a> Allixin showed an anti-tumor promoting effect in vivo, inhibiting skin <a href="/facts/Tumor/K0ytzmPz">tumor</a> formation by <a href="/facts/12-O-Tetradecanoylphorbol-13-acetate/nSbzMM6a">TPA</a> in <a href="/facts/7,12-Dimethylbenz(a)anthracene/nPmMJGs3">DMBA</a> initiated mice.<a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</sup></a> Herein, allixin and/or its analogs may be expected to be useful compounds for cancer prevention or chemotherapy agents for other diseases. </p> <h2 id="role-of-natural-phenols-in-the-plant-defense-against-fungal-pathogens">Role of natural phenols in the plant defense against fungal pathogens</h2> <p><a href="/facts/Polyphenol/H6Q7QIQH">Polyphenols</a>, especially <a href="/facts/Isoflavonoid/CVsGmIlc">isoflavonoids</a> and related substances, play a role in the plant defense against fungal and other microbial pathogens. </p><p>In <i><a href="/facts/Vitis_vinifera/n7u6fzeq">Vitis vinifera</a></i> grape, <i>trans</i>-<a href="/facts/Resveratrol/5sF3fvl7">resveratrol</a> is a phytoalexin produced against the growth of fungal pathogens such as <i><a href="/facts/Botrytis_cinerea/m3pJzsdP">Botrytis cinerea</a></i><a class="footnote-ref" id="fnref:9" href="#fn:9"><sup>9</sup></a> and <a href="/facts/Delta-viniferin/SRMGP7e5">delta-viniferin</a> is another grapevine phytoalexin produced following <a href="/facts/Fungal_infection_in_plants/h6DTufWF">fungal infection</a> by <i><a href="/facts/Plasmopara_viticola/xsFWqHrY">Plasmopara viticola</a></i>.<a class="footnote-ref" id="fnref:10" href="#fn:10"><sup>10</sup></a> <a href="/facts/Pinosylvin/BAe7C8k2">Pinosylvin</a> is a pre-infectious <a href="/facts/Stilbenoid/tTqUnyL2">stilbenoid</a> toxin (i.e. synthesized prior to infection), contrary to phytoalexins which are synthesized during infection. It is present in the <a href="/facts/Heartwood/z13NpHPl">heartwood</a> of <i><a href="/facts/Pinaceae/Ry0GUN97">Pinaceae</a></i>.<a class="footnote-ref" id="fnref:11" href="#fn:11"><sup>11</sup></a> It is a fungitoxin protecting the wood from <a href="/facts/Fungal_infection_in_plants/h6DTufWF">fungal infection</a>.<a class="footnote-ref" id="fnref:12" href="#fn:12"><sup>12</sup></a> </p><p><a href="/facts/Sakuranetin/CYMITsqt">Sakuranetin</a> is a <a href="/facts/Flavanone/lMEpwpcx">flavanone</a>, a type of flavonoid. It can be found in <i><a href="/facts/Polymnia_fruticosa/Mc4TIjPB">Polymnia fruticosa</a></i><a class="footnote-ref" id="fnref:13" href="#fn:13"><sup>13</sup></a> and <a href="/facts/Rice/wvL1hBCz">rice</a>, where it acts as a phytoalexin against spore germination of <i><a href="/facts/Magnaporthe_grisea/09z46Dgk">Pyricularia oryzae</a></i>.<a class="footnote-ref" id="fnref:14" href="#fn:14"><sup>14</sup></a> In <i><a href="/facts/Sorghum/D1KNhtdT">Sorghum</a></i>, the <i>SbF3'H2</i> gene, encoding a <a href="/facts/Flavonoid_3%27-hydroxylase/8HpoN4e7">flavonoid 3'-hydroxylase</a>, seems to be expressed in <a href="/facts/Plant_pathology/h6DTufWF">pathogen</a>-specific <a href="/facts/3-deoxyanthocyanidin/YowwKQ8o">3-deoxyanthocyanidin</a> phytoalexin synthesis,<a class="footnote-ref" id="fnref:15" href="#fn:15"><sup>15</sup></a> for example in <i>Sorghum-<a href="/facts/Colletotrichum/jNqp1zhF">Colletotrichum</a></i> interactions.<a class="footnote-ref" id="fnref:16" href="#fn:16"><sup>16</sup></a> </p><p><a href="/facts/6-Methoxymellein/xMX3GJ76">6-Methoxymellein</a> is a <a href="/facts/Dihydroisocoumarin/yfW7b5V4">dihydroisocoumarin</a> and a phytoalexin induced in carrot slices by <a href="/facts/Ultraviolet_C/kncBUqn5">UV-C</a>,<a class="footnote-ref" id="fnref:17" href="#fn:17"><sup>17</sup></a> that allows resistance to <i><a href="/facts/Botrytis_cinerea/m3pJzsdP">Botrytis cinerea</a></i><a class="footnote-ref" id="fnref:18" href="#fn:18"><sup>18</sup></a> and other <a href="/facts/Microorganism/pysJYcE2">microorganisms</a>.<a class="footnote-ref" id="fnref:19" href="#fn:19"><sup>19</sup></a> </p><p><a href="/facts/Danielone/QPJKvkJs">Danielone</a> is a phytoalexin found in the <a href="/facts/Papaya/VKB9mrnk">papaya</a> fruit. This compound showed high antifungal activity against <i><a href="/facts/Colletotrichum_gloesporioides/qohWz3s1">Colletotrichum gloesporioides</a></i>, a pathogenic fungus of papaya.<a class="footnote-ref" id="fnref:20" href="#fn:20"><sup>20</sup></a> </p><p><a href="/facts/Stilbenoid/tTqUnyL2">Stilbenes</a> are produced in <i><a href="/facts/Eucalyptus_sideroxylon/qWathmUD">Eucalyptus sideroxylon</a></i> in case of pathogen attacks. Such compounds can be implied in the <a href="/facts/Hypersensitive_response/q1FDzzeP">hypersensitive response</a> of plants. High levels of <a href="/facts/Polyphenol/H6Q7QIQH">polyphenols</a> in some woods can explain their natural <a href="/facts/Wood_preservation/eLLDnkbE">preservation</a> against rot.<a class="footnote-ref" id="fnref:21" href="#fn:21"><sup>21</sup></a> </p><p><a href="/facts/Avenanthramide/fNJLxP2W">Avenanthramides</a> are phytoalexins produced by <i><a href="/facts/Avena_sativa/wn3vnCnT">Avena sativa</a></i> in its response to <i><a href="/facts/Puccinia_coronata/5r16XS6A">Puccinia coronata</a></i> var. <i>avenae</i> f. sp. <i>avenae</i>, the oat crown <a href="/facts/Rust_(fungus)/NbnnK0ay">rust</a>.<a class="footnote-ref" id="fnref:22" href="#fn:22"><sup>22</sup></a><a class="footnote-ref" id="fnref:23" href="#fn:23"><sup>23</sup></a> (Avenanthramides were formerly called avenalumins.)<a class="footnote-ref" id="fnref:24" href="#fn:24"><sup>24</sup></a> </p> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/Alexin/qG9I4pGf">Alexin</a> (humoral immunity)</li> <li><a href="/facts/Allicin/tPLWtC2a">Allicin</a></li> <li><a href="/facts/Garlic/NschLR1S">Garlic</a></li> <li><a href="/facts/Plant_defense_against_herbivory/2MKbXxUp">Plant defense against herbivory</a></li> <li><a href="/facts/Pterostilbene/7qYJvLQ3">Pterostilbene</a></li> <li><a href="/facts/Salvestrol/HSmrU32C">Salvestrol</a></li></ul> <h2 id="further-reading">Further reading</h2> <ul><li>Moriguchi, Toru; Matsuura, Hiromichi; Itakura, Yoichi; Katsuki, Hiroshi; Saito, Hiroshi; Nishiyama, Nobuyoshi (1997). "Allixin, a phytoalexin produced by garlic, and its analogues as novel exogenous substances with neurotrophic activity". <i>Life Sciences</i>. 61 (14): 1413–1420. <a href="/facts/Doi_(identifier)/muM9Etpq">doi</a>:<a href="https://doi.org/10.1016%2FS0024-3205%2897%2900687-5">10.1016/S0024-3205(97)00687-5</a>. <a href="/facts/PMID_(identifier)/JlHAvMHt">PMID</a> <a href="https://pubmed.ncbi.nlm.nih.gov/9335231">9335231</a>.</li> <li>Kodera, Yukihiro; Ichikawa, Makoto; Yoshida, Jiro; Kashimoto, Naoki; Uda, Naoto; Sumioka, Isao; Ide, Nagatoshi; Ono, Kazuhisa (2002). <a href="https://doi.org/10.1248%2Fcpb.50.354">"Pharmacokinetic Study of Allixin, a Phytoalexin Produced by Garlic"</a>. <i>Chemical and Pharmaceutical Bulletin</i>. 50 (3): 354–363. <a href="/facts/Doi_(identifier)/muM9Etpq">doi</a>:<a href="https://doi.org/10.1248%2Fcpb.50.354">10.1248/cpb.50.354</a>. <a href="/facts/PMID_(identifier)/JlHAvMHt">PMID</a> <a href="https://pubmed.ncbi.nlm.nih.gov/11911198">11911198</a>.</li></ul> <h2 id="external-links">External links</h2> <ul><li><a href="https://web.archive.org/web/20110604234827/http://www.lancs.ac.uk/staff/robertmr/downloads/mrr-crips.pdf">Signals Regulating Multiple Responses to Wounding and Herbivores</a> Guy L. de Bruxelles and Michael R Roberts</li> <li><a href="https://web.archive.org/web/20040609070225/http://www.cepceb.ucr.edu/resources/pdf/walling/Walling-2000-JPGR.pdf">The Myriad Plant Responses to Herbivores</a> Linda L. Walling</li> <li><a href="https://www.uky.edu/~garose/link100.htm">The Chemical Defenses of Higher Plants</a> Gerald A. Rosenthal</li> <li><a href="https://web.archive.org/web/20041012013705/http://aob.oupjournals.org/cgi/content/full/89/5/503">Induced Systemic Resistance (ISR) Against Pathogens in the Context of Induced Plant Defences</a> Martin Heil</li> <li><a href="https://academic.oup.com/plphys/article/127/3/727/6110169?login=false">Notes from the Underground</a> Donald R. Strong and Donald A. Phillips</li> <li><a href="https://web.archive.org/web/20040813200322/http://www.colostate.edu/Depts/Entomology/courses/en570/papers_2000/mannix.html">Relationships Among Plants, Insect Herbivores, Pathogens, and Parasitoids Expressed by Secondary Metabolites</a> Loretta L. Mannix</li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>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. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC44725" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC44725</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Kodera 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. <a href="https://doi.org/10.1248%2Fcpb.37.1656" target="_blank">https://doi.org/10.1248%2Fcpb.37.1656</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Kodera 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. <a href="https://doi.org/10.1248%2Fcpb.37.1656" target="_blank">https://doi.org/10.1248%2Fcpb.37.1656</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Kodera 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. <a href="https://doi.org/10.1248%2Fcpb.37.1656" target="_blank">https://doi.org/10.1248%2Fcpb.37.1656</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Nishino 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. <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Yamasaki 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. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>Yamasaki 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. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><p>Nishino 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. <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> <li id="fn:9"><p>F. Favaron; M. Lucchetta; S. Odorizzi; A.T. Pais da Cunha; L. Sella (2009). "The role of grape polyphenols on trans-resveratrol activity against Botrytis cinerea and of fungal laccase on the solubility of putative grape PR proteins" (PDF). Journal of Plant Pathology. 91 (3): 579–588. Retrieved 2011-01-22. <a href="https://www.sipav.org/main/jpp/volumes/0309/030909.pdf" target="_blank">https://www.sipav.org/main/jpp/volumes/0309/030909.pdf</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></p></li> <li id="fn:10"><p>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 with Botrytis cinerea in field conditions". Plant Physiology and Biochemistry. 50 (1): 65–71. doi:10.1016/j.plaphy.2011.07.008. PMID 21821423. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:10" class="footnote-back-ref">↩</a></p></li> <li id="fn:11"><p>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. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6148674" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6148674</a> <a href="#fnref:11" class="footnote-back-ref">↩</a></p></li> <li id="fn:12"><p>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. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:12" class="footnote-back-ref">↩</a></p></li> <li id="fn:13"><p>"Structure and Data for Sakuranetin (NSC 407228)". home.ncifcrf.gov. Archived from the original on 2018-12-03. Retrieved 2012-04-13. <a href="https://web.archive.org/web/20181203010928/https://home.ncifcrf.gov/mtdp/Catalog/compounds/407228.html" target="_blank">https://web.archive.org/web/20181203010928/https://home.ncifcrf.gov/mtdp/Catalog/compounds/407228.html</a> <a href="#fnref:13" class="footnote-back-ref">↩</a></p></li> <li id="fn:14"><p>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. <a href="/wiki/Bibcode_(identifier)" target="_blank">/wiki/Bibcode_(identifier)</a> <a href="#fnref:14" class="footnote-back-ref">↩</a></p></li> <li id="fn:15"><p>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. <a href="https://academic.oup.com/pcp/article/47/10/1412/2279020" target="_blank">https://academic.oup.com/pcp/article/47/10/1412/2279020</a> <a href="#fnref:15" class="footnote-back-ref">↩</a></p></li> <li id="fn:16"><p>Chopra, Surinder; Gaffoor, Iffa; Ibraheem, Farag. "Biosynthesis and regulation of 3-deoxyanthocyanidin phytoalexins induced during Sorghum-Colletotrichum interaction: Heterologous expression in maize". Archived from the original on 2011-07-25. <a href="https://web.archive.org/web/20110725021532/http://abstracts.aspb.org/pb2009/public/P48/P48067.html" target="_blank">https://web.archive.org/web/20110725021532/http://abstracts.aspb.org/pb2009/public/P48/P48067.html</a> <a href="#fnref:16" class="footnote-back-ref">↩</a></p></li> <li id="fn:17"><p>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. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:17" class="footnote-back-ref">↩</a></p></li> <li id="fn:18"><p>Hoffman, R.; Heale, J.B. (1987). "Cell death, 6-methoxymellein accumulation, and induced resistance to Botrytis cinerea in carrot root slices". 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