A maize death acid, 10-oxo-11-phytoenoic acid, is the predominant cyclopentenone signal present during multiple stress and developmental conditions

References

• Ricciotti E, FitzGerald GA. Prostaglandins and inflammation. Arterioscler Thromb Vasc Biol 2011; 31:986-1000; PMID:21508345; http://dx.doi.org/10.1161/ATVBAHA.110.207449.
   PubMed Web of Science ®Google Scholar
• Farmer EE, Almeras E, Krishnamurthy V. Jasmonates and related oxylipins in plant responses to pathogenesis and herbivory. Curr Opin Plant Biol 2003; 6:372-8; PMID:12873533; http://dx.doi.org/10.1016/S1369-5266(03)00045-1.
   PubMed Web of Science ®Google Scholar
• Wasternack C, Hause B. Jasmonates: biosynthesis, perception, signal transduction and action in plant stress response, growth and development. An update to the 2007 review in Annals of Botany. Ann Bot 2013; 111:1021-58; PMID:23558912; http://dx.doi.org/10.1093/aob/mct067.
   PubMed Web of Science ®Google Scholar
• Acosta IF, Laparra H, Romero SP, Schmelz E, Hamberg M, Mottinger JP, Moreno MA, Dellaporta SL. tasselseed1 Is a Lipoxygenase Affecting Jasmonic Acid Signaling in Sex Determination of Maize. Science 2009; 323:262-5; PMID:19131630; http://dx.doi.org/10.1126/science.1164645.
   PubMed Web of Science ®Google Scholar
• Yan Y, Christensen S, Isakeit T, Engelberth J, Meeley R, Hayward A, Emery RJN, Kolomiets MV. Disruption of OPR7 and OPR8 Reveals the Versatile Functions of Jasmonic Acid in Maize Development and Defense. Plant Cell 2012; 24:1420-36; PMID:22523204; http://dx.doi.org/10.1105/tpc.111.094151.
   PubMed Web of Science ®Google Scholar
• Stintzi A, Weber H, Reymond P, Browse J, Farmer EE. Plant defense in the absence of jasmonic acid: The role of cyclopentenones. Proc Natl Acad Sci U S A 2001; 98:12837-42; PMID:11592974; http://dx.doi.org/10.1073/pnas.211311098.
   PubMed Web of Science ®Google Scholar
• Mueller S, Hilbert B, Dueckershoff K, Roitsch T, Krischke M, Mueller MJ, Berger S. General detoxification and stress responses are mediated by oxidized lipids through TGA transcription factors in Arabidopsis. Plant Cell 2008; 20:768-85; PMID:18334669; http://dx.doi.org/10.1105/tpc.107.054809.
   PubMed Web of Science ®Google Scholar
• Fonseca S, Chini A, Hamberg M, Adie B, Porzel A, Kramell R, Miersch O, Wasternack C, Solano R. (+)-7-iso-Jasmonoyl-L-isoleucine is the endogenous bioactive jasmonate. Nat Chem Biol 2009; 5:344-50; PMID:19349968; http://dx.doi.org/10.1038/nchembio.161.
   PubMed Web of Science ®Google Scholar
• Park S-W, Li W, Viehhauser A, He B, Kim S, Nilsson AK, Andersson MX, Kittle JD, Ambavaram MMR, Luan S, et al. Cyclophilin 20-3 relays a 12-oxo-phytodienoic acid signal during stress responsive regulation of cellular redox homeostasis. Proc Natl Acad Sci U S A 2013; 110:9559-64; PMID:23671085; http://dx.doi.org/10.1073/pnas.1218872110.
   PubMed Web of Science ®Google Scholar
• Thoma I, Loeffler C, Sinha AK, Gupta M, Krischke M, Steffan B, Roitsch T, Mueller MJ. Cyclopentenone isoprostanes induced by reactive oxygen species trigger defense gene activation and phytoalexin accumulation in plants. Plant J 2003; 34:363-75; PMID:12713542; http://dx.doi.org/10.1046/j.1365-313X.2003.01730.x.
   PubMed Web of Science ®Google Scholar
• Montillet JL, Chamnongpol S, Rusterucci C, Dat J, van de Cotte B, Agnel JP, Battesti C, Inze D, Van Breusegem F, Triantaphylides C. Fatty acid hydroperoxides and H2O2 in the execution of hypersensitive cell death in tobacco leaves. Plant Physiol 2005; 138:1516-26; PMID:15980200; http://dx.doi.org/10.1104/pp.105.059907.
   PubMed Web of Science ®Google Scholar
• van der Linde K, Hemetsberger C, Kastner C, Kaschani F, van der Hoorn RA, Kumlehn J, Doehlemann G. A maize cystatin suppresses host immunity by inhibiting apoplastic cysteine proteases. Plant Cell 2012; 24:1285-300; PMID:22454455; http://dx.doi.org/10.1105/tpc.111.093732.
   PubMed Web of Science ®Google Scholar
• Christensen SA, Huffaker A, Kaplan F, Sims J, Ziemann S, Doehlemann G, Ji L, Schmitz RJ, Kolomiets MV, Alborn HT, et al. Maize death acids, 9-lipoxygenase-derived cyclopente(a)nones, display activity as cytotoxic phytoalexins and transcriptional mediators. Proc Natl Acad Sci U S A 2015; 112:11407-12; PMID:26305953; http://dx.doi.org/10.1073/pnas.1511131112.
   PubMed Web of Science ®Google Scholar
• Vellosillo T, Martinez M, Lopez MA, Vicente J, Cascon T, Dolan L, Hamberg M, Castresana C. Oxylipins produced by the 9-lipoxygenase pathway in Arabidopsis regulate lateral root development and defense responses through a specific signaling cascade. Plant Cell 2007; 19:831-46; PMID:17369372; http://dx.doi.org/10.1105/tpc.106.046052.
   PubMed Web of Science ®Google Scholar
• Gao X, Starr J, Goebel C, Engelberth J, Feussner I, Tumlinson J, Kolomiets M. Maize 9-lipoxygenase ZmLOX3 controls development, root-specific expression of defense genes, and resistance to root-knot nematodes. Mol Plant-Microbe Interact 2008; 21:98-109; PMID:18052887; http://dx.doi.org/10.1094/MPMI-21-1-0098.
   PubMed Web of Science ®Google Scholar
• Gao X, Shim WB, Gobel C, Kunze S, Feussner I, Meeley R, Balint-Kurti P, Kolomiets M. Disruption of a maize 9-lipoxygenase results in increased resistance to fungal pathogens and reduced levels of contamination with mycotoxin fumonisin. Mol Plant Microbe Interact 2007; 20:922-33; PMID:17722696; http://dx.doi.org/10.1094/MPMI-20-8-0922.
   PubMed Web of Science ®Google Scholar
• Weber H, Chetelat A, Caldelari D, Farmer EE. Divinyl ether fatty acid synthesis in late blight-diseased potato leaves. Plant Cell 1999; 11:485-94; PMID:10072406.
   PubMed Web of Science ®Google Scholar
• Hwang IS, Hwang BK. The Pepper 9-Lipoxygenase Gene CaLOX1 Functions in Defense and Cell Death Responses to Microbial Pathogens. Plant Physiol 2010; 152:948-67; PMID:19939946; http://dx.doi.org/10.1104/pp.109.147827.
   PubMed Web of Science ®Google Scholar
• Hamberg M. New cyclopentenone fatty acids formed from linoleic and linolenic acids in potato. Lipids 2000; 35:353-63; PMID:10858019; http://dx.doi.org/10.1007/s11745-000-532-z.
   PubMed Web of Science ®Google Scholar
• Itoh A, Schilmiller AL, McCaig BC, Howe GA. Identification of a jasmonate-regulated allene oxide synthase that metabolizes 9-hydroperoxides of linoleic and linolenic acids. J Biol Chem 2002; 277:46051-8; PMID:12351632; http://dx.doi.org/10.1074/jbc.M207234200.
   PubMed Web of Science ®Google Scholar
• Ogorodnikova AV, Gorina SS, Mukhtarova LS, Mukhitova FK, Toporkova YY, Hamberg M, Grechkin AN. Stereospecific biosynthesis of (9S,13S)-10-oxo-phytoenoic acid in young maize roots. Biochim Biophys Acta 2015; 1851:1262-70; PMID:26008579; http://dx.doi.org/10.1016/j.bbalip.2015.05.004.
   PubMed Web of Science ®Google Scholar
• Kiesselbach TA. The structure and reproduction of corn. Cold Spring Harbor laboratory press: Cold Spring Harbor, 1949.
   Google Scholar
• Christensen SA, Nemchenko A, Borrego E, Murray I, Sobhy IS, Bosak L, DeBlasio S, Erb M, Robert CA, Vaughn KA, et al. The maize lipoxygenase, ZmLOX10, mediates green leaf volatile, jasmonate and herbivore-induced plant volatile production for defense against insect attack. Plant J 2013; 74:59-73; PMID:23279660; http://dx.doi.org/10.1111/tpj.12101.
   PubMed Web of Science ®Google Scholar
• Marsh S, Payne, G. Preharvest infection of corn silks and kernels by Aspergillus flavus. Phytopathology 1984; 74:1284-9; http://dx.doi.org/10.1094/Phyto-74-1284.
   Web of Science ®Google Scholar
• Campos-Bermudez VA, Fauguel CM, Tronconi MA, Casati P, Presello DA, Andreo CS. Transcriptional and metabolic changes associated to the infection by Fusarium verticillioides in maize inbreds with contrasting ear rot resistance. PloS One 2013; 8:e61580; PMID:23637860; http://dx.doi.org/10.1371/journal.pone.0061580.
   PubMed Web of Science ®Google Scholar
• Schmelz EA, Engelberth J, Alborn HT, Tumlinson JH, 3rd, Teal PE. Phytohormone-based activity mapping of insect herbivore-produced elicitors. Proc Natl Acad Sci U S A 2009; 106:653-7; PMID:19124770; http://dx.doi.org/10.1073/pnas.0811861106.
   PubMed Web of Science ®Google Scholar
• Schmelz EA, Kaplan F, Huffaker A, Dafoe NJ, Vaughan MM, Ni X, Rocca JR, Alborn HT, Teal PE. Identity, regulation, and activity of inducible diterpenoid phytoalexins in maize. Proc Natl Acad Sci U S A 2011; 108:5455-60; PMID:21402917; http://dx.doi.org/10.1073/pnas.1014714108.
   PubMed Web of Science ®Google Scholar