The isoprostanoid pathway in plants

Blechert, 1995, The octadecanoic pathway: signal molecules for the regulation of secondary pathways, Proc. Natl. Acad. Sci. U.S.A., 92, 4099, 10.1073/pnas.92.10.4099 Bolwell, 1999, Role of oxygen species and NO in plant responses, Curr. Opin. Plant Biol., 2, 287, 10.1016/S1369-5266(99)80051-X Burke, 2000, Specific analysis in plasma and urine of 2,3-dinor-5,6-dihydro-isoprostane F2α-III, a metabolite of isoprostane F2α-III and an oxidation product of γ-linolenic acid, J. Biol. Chem., 275, 2499, 10.1074/jbc.275.4.2499 Chen, 1999, Formation of reactive cyclopentenone compounds in vivo as products of the isoprostane pathway, J. Biol. Chem., 274, 10863, 10.1074/jbc.274.16.10863 Chiabrando, 1999, Identification and measurement of endogenous β-oxidation metabolites of 8-epi-prostaglandin F2α, J. Biol. Chem., 274, 1313, 10.1074/jbc.274.3.1313 Conconi, 1996, Intracellular levels of free linolenic and linoleic acid increase in tomato leaves in response to wounding, Plant Physiol., 111, 797, 10.1104/pp.111.3.797 Gundlach, 1998, Biological activity and biosynthesis of pentacyclic oxylipins: the linoleic acid pathway, Phytochemistry, 47, 527, 10.1016/S0031-9422(97)00572-4 Gundlach, 1992, Jasmonic acid is a signal transducer in elicitor-induced plant cell cultures, Proc. Natl. Acad. Sci. U.S.A., 89, 2389, 10.1073/pnas.89.6.2389 Haider, 2000, Structure–activity relationships of synthetic analogs of jasmonic acid and coronatine on induction of benzo[c]phenanthridine alkaloid accumulation in Eschscholzia californica cell cultures, Biol. Chem., 381, 741, 10.1515/BC.2000.094 Hou, 2001, 2,3-Dinor-5,6-dihydro-15-F2t-isoprostane: a bioactive prostanoid metabolite, Am. J. Physiol. Regul. Integr. Comp. Physiol., 281, R391, 10.1152/ajpregu.2001.281.2.R391 Howe, 1996, An octadecanoid pathway mutant (JL5) of tomato is comprised in signalling for defense against insect attack, Plant Cell, 8, 2067, 10.1105/tpc.8.11.2067 Imbusch, 2000, Formation of isoprostane F2-like compounds (phytoprostanes F1) from α-linolenic acid in plants, Free Radic. Biol. Med., 28, 720, 10.1016/S0891-5849(00)00154-4 Imbusch, 2000, Analysis of oxidative stress and wound-inducible dinor isoprostanes F1 (phytoprostanes F1) in plants, Plant Physiol., 124, 1293, 10.1104/pp.124.3.1293 Kayganich-Harrison, 1993, Collision-induced dissociation of F2-isoprostane-containing phospholipids, J. Lipid Res., 34, 1229, 10.1016/S0022-2275(20)37710-5 Kondo, 2002, 15-Deoxy-Δ12,14-prostaglandin J2: the endogenous electrophile that induces neuronal apoptosis, Proc. Natl. Acad. Sci. U.S.A., 99, 7367, 10.1073/pnas.112212599 Krischke, 2003, Biosynthesis of 13,14-dehydro-12-oxo-phytodienoic acid and related cyclopentenones via the phytoprostane D1 pathway, Phytochemistry, 62, 351, 10.1016/S0031-9422(02)00566-6 McConn, 1996, The critical requirement for linolenic acid in pollen development, not photosynthesis, in an Arabidopsis mutant, Plant Cell, 8, 403, 10.1105/tpc.8.3.403 McConn, 1997, Jasmonate is essential for insect defense in Arabidopsis, Proc. Natl. Acad. Sci. U.S.A., 94, 5473, 10.1073/pnas.94.10.5473 Morrow, 1990, Noncyclooxygenase oxidative formation of a series of novel prostaglandins: analytical ramifications for measurement of eicosanoids, Anal. Biochem., 184, 1, 10.1016/0003-2697(90)90002-Q Morrow, 1992, Non-cyclooxygenase-derived prostanoids (F2-isoprostanes) are formed in situ in phospholipids, Proc. Natl. Acad. Sci. U.S.A., 89, 10721, 10.1073/pnas.89.22.10721 Morrow, 1994, Free radical-induced generation of isoprostanes in vivo. Evidence for the formation of D-ring and E-ring isoprostanes, J. Biol. Chem., 269, 4317, 10.1016/S0021-9258(17)41781-9 Morrow, 1999, Quantification of the major urinary metabolite of 15-F2t-isoprostane (8-iso-PGF2α) by a stable isotope dilution mass spectrometric assay, Anal. Biochem., 269, 326, 10.1006/abio.1999.4008 Mueller, 1997, Enzymes involved in jasmonic acid biosynthesis, Physiol. Plant, 100, 653, 10.1111/j.1399-3054.1997.tb03072.x Mueller, 1998, Radically novel prostaglandins in animals and plants: the isoprostanes, Chem. Biol., 5, 323, 10.1016/S1074-5521(98)90660-3 Mueller, 1993, Signaling in the elicitation process is mediated through the octadecanoid pathway leading to jasmonic acid, Proc. Natl. Acad. Sci. U.S.A., 90, 7490, 10.1073/pnas.90.16.7490 Nugteren, 1967, Non-enzymatic conversion of all-cis 8,11,14-eicosatrienoic acid into prostaglandin E1, Recl. Trav. Chim. Pays-Bas., 86, 1237, 10.1002/recl.19670861109 O’Connor, 1981, Isolation and characterisation of bicyclo endoperoxides derived from methyl linolenate, J. Am. Chem. Soc., 103, 223, 10.1021/ja00391a056 O’Connor, 1984, Stereochemical course of the autoxidative cyclization of lipid hydroperoxides to prostaglandin-like bicyclo endoperoxides, J. Am. Chem. Soc., 106, 3577, 10.1021/ja00324a028 Parchmann, 1998, Evidence for the formation of dinor isoprostanes E1 from α-linolenic acid in plants, J. Biol. Chem., 273, 32650, 10.1074/jbc.273.49.32650 Parchmann, 1997, Induction of 12-oxo-phytodienoic acid in wounded plants and elicited plant cell cultures, Plant Physiol., 115, 1057, 10.1104/pp.115.3.1057 Pryor, 1976, Autoxidation of polyunsaturated fatty acids: II. A suggested mechanism for the formation of TBA-reactive materials from prostaglandin-like endoperoxides, Lipids, 11, 370, 10.1007/BF02532843 Reymond, 2000, Differential gene expression in response to mechanical wounding and insect feeding in Arabisopsis, Plant Cell, 12, 707, 10.1105/tpc.12.5.707 Roberts, 2002, Products of the isoprostane pathway: unique bioactive compounds and markers of lipid peroxidation, Cell. Mol. Life Sci., 59, 808, 10.1007/s00018-002-8469-8 Roberts, 1998, Formation of isoprostane-like compounds (neuroprostanes) in vivo from docosahexaenoic acid, J. Biol. Chem., 273, 13605, 10.1074/jbc.273.22.13605 Rokach, 1997, Nomenclature of isoprostanes: a proposal, Prostaglandins, 54, 853, 10.1016/S0090-6980(97)00184-6 Rossi, 2000, Anti-inflammatory cyclopentenone prostaglandins are direct inhibitors of IκB kinase, Nature, 403, 103, 10.1038/47520 Ryan, 2000, The systemin signaling pathway: differential activation of plant defensive genes, Biochim. Biophys. Acta, 1477, 112, 10.1016/S0167-4838(99)00269-1 Santoro, 1997, Antiviral activity of cyclopentenone prostanoids, Trends Microbiol., 5, 276, 10.1016/S0966-842X(97)01066-4 Stelmach, 2001, A novel class of oxylipins, sn1-O-(12-oxophytodienoyl)-sn2-O-(hexadecatrienoyl)-monogalactosyl diglyceride, from Arabidopsis thaliana, J. Biol. Chem., 276, 12832, 10.1074/jbc.M010743200 Stintzi, 2000, The Arabidopsis male-sterile mutant, opr3, lacks the 12-oxophytodienoic acid reductase required for jasmonate synthesis, Proc. Natl. Acad. Sci. U.S.A., 97, 10625, 10.1073/pnas.190264497 Stintzi, 2001, Plant defense in the absence of jasmonic acid: the role of cyclopentenones, Proc. Natl. Acad. Sci. U.S.A., 98, 12837, 10.1073/pnas.211311098 Taber, 1997, A nomenclature system for isoprostanes, Prostaglandins, 53, 63, 10.1016/S0090-6980(97)00005-1 Thoma, 2003, Cyclopentenone isoprostanes induced by reactive oxygen species trigger defense gene activation and phytoalexin accumulation in plants, Plant J., 34, 363, 10.1046/j.1365-313X.2003.01730.x Weber, 2002, Fatty acid-derived signals in plants, Trends Plant Sci., 7, 217, 10.1016/S1360-1385(02)02250-1