Biosynthesis of 13,14-dehydro-12-oxo-phytodienoic acid and related cyclopentenones via the phytoprostane D1 pathway

Phytochemistry

Volumn 62, Issue 3, 2003, Pages 351-358

  Krischke, Markus ^a   Loeffler, Christiane ^a   Mueller, Martin J ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

12 Oxo phytodienoic acid; 13,14 Dehydro 12 oxo phytodienoic acid; Chromomoric acid; Cross conjugated cyclopentenone; Deoxy phytoprostane J1; Isoprostane; Jasmonate; Prostaglandin

Indexed keywords

12 OXOPHYTODIENOIC ACID; 13,14 DEHYDRO 12 OXOPHYTODIENOIC ACID; ALLENE OXIDE SYNTHASE; CHROMOMORIC ACID; CYCLOPENTENONE DERIVATIVE; DEOXYPHYTOPROSTANE J1; ISOPROSTANE; JASMONIC ACID; KETOL; PHYTOPROSTANE D1; PROSTAGLANDIN; SYNTHETASE; UNCLASSIFIED DRUG; 12-OXOPHYTODIENOIC ACID; CYCLOPENTANE DERIVATIVE; CYCLOPENTENONE; PHYTOHORMONE; PLANT EXTRACT; PROSTANE, HERBAL PREPARATION; UNSATURATED FATTY ACID;

ARABIDOPSIS; ARTICLE; BIOSYNTHESIS; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; NONHUMAN; TOBACCO; TOMATO; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLISM; STEREOISOMERISM;

ARABIDOPSIS; LYCOPERSICON ESCULENTUM; NICOTIANA TABACUM;

ARABIDOPSIS; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLOPENTANES; FATTY ACIDS, UNSATURATED; LYCOPERSICON ESCULENTUM; PLANT EXTRACTS; PLANT GROWTH REGULATORS; STEREOISOMERISM; TOBACCO;

EID: 0037308057     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(02)00566-6     Document Type: Article

References (27)

1. Bohlmann, F., Gupta, R.K., King, R.M., Robinson, H., 1981. Prostaglandin-like fatty acid derivative from Chromolaena morii. Phytochemistry 20, 1417-1418.
2. Bohlmann, F., Borthakur, N., King, R.M., Robinson, H., 1982a. Further prostaglandin-like fatty acids from Chromolaena morii. Phytochemistry 21, 125-127.
3. Bohlmann, F., Singh, P., Jakupovic, J., King, R.M., Robinson, H., 1982b. Three cadeinene derivatives and a prostaglandin-like acid from Chromolaena species. Phytochemistry 21, 371-374.
4. Chen, Y., Morrow, J.D., Roberts II., L.J., 1999. Formation of reactive cyclopentenone compounds in vivo as products of the isoprostane pathway. J. Biol. Chem. 274, 10863-10868.
5. Cracowski, J.L., Devillier, P., Durand, T., Stanke-Labesque, F., Bessard, G., 2001. Vascular biology of the isoprostanes. J. Vasc. Res. 38, 93-103.
6. Grechkin, A., 1998. Recent developments in biochemistry of the plant lipoxygenase pathway. Prog. Lipid Res. 37, 317-352.
7. Grechkin, A.N., 1995. Clavulones and related tert-hydroxycyclopentenone fatty acids: occurence, physiological activity and problem of biogenetic origin. J. Lipid Mediat. Cell Signal 11, 205-218.
8. Haider, G., von Schrader, T., Füßlein, M., Blechert, S., Kutchan, T.M., 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, 741-748.
9. Hamberg, M., Svensson, J., Wakabayashi, T., Samuelsson, B., 1974. Isolation and structure of two prostaglandin endoperoxides that cause platelet aggregation. Proc. Nat. Acad. Sci. USA 71, 345-349.
10. 1) in plants. Plant Physiol. 124, 1293-1303.
11. 1) from α-linolenic acid in plants. Free Rad. Biol. Med. 28, 720-726.
12. Janssen, L.J., 2001. Isoprostanes: an overview and putative roles in pulmonary pathophysiology. Am. J. Physiol. Lung Cell Mol. Physiol. 280, L1067-1082.
13. 2: the endogenous electrophile that induces neuronal apoptosis. Proc. Natl. Acad. Sci. USA 7367-7372.
14. 2. Prostaglandins Other Lipid Mediat 62, 15-21.
15. Morrow, J.D., Minton, T.A., Mukundan, C.R., Campbell, M.D., Zackert, W.E., Daniel, V.C., Badr, K.F., Blair, I.A., Roberts, L.J., 1994. Free radical-induced generation of isoprostanes in vivo. Evidence for the formation of D-ring and E-ring isoprostanes. J. Biol. Chem. 269, 4317-4326.
16. Mueller, M.J., 1997. Enzymes involved in jasmonic acid biosynthesis. Physiol. Plant 100, 653-663.
17. Mueller, M.J., 1998. Radically novel prostaglandins in animals and plants: the isoprostanes. Chem. Biol. 5, 323-333.
18. 2 as potential antithrombotic agent. Prostaglandins 9, 109-121.
19. O'Connor, D.E., Mihelich, E.D., Coleman, M.C., 1981. Isolation and characterization of bicyclo endoperoxides derived from methyl linolenate. J. Am. Chem. Soc. 103, 223-224.
20. O'Connor, D.E., Mihelich, E.D., Coleman, M.C., 1984. Stereochemical course of the autoxidative cyclization of lipid hydroperoxides to prostaglandin-like bicyclo endoperoxides. J. Am. Chem. Soc. 106, 3577-3584.
21. 1 from α-linolenic acid in plants. J. Biol. Chem. 273, 32650-32655.
22. Rokach, J., Khanapure, S.P., Hwang, S.-W., Adiyaman, M., Lawson, J.A., Fitzgerald, G.A., 1997. Nomenclature of isoprostanes: a proposal. Prostaglandins 54, 853-873.
23. Rossi, A., Kapahi, P., Natoli, G., Takahashi, T., Chen, Y., Karin, M., Santoro, M.G., 2000. Anti-inflammatory cyclopentenone prostaglandins are direct inhibitors of IκB kinase. Nature 403, 103-108.
24. Santoro, M.G., 1997. Antiviral activity of cyclopentenone prostanoids. Trends Microbiol. 5, 276-281.
25. 2 metabolite generated during inflammatory processes. J. Biol. Chem. 277, 10459-10466.
26. Stintzi, A., Weber, H., Reymond, P., Browse, J., Farmer, E.E., 2001. Plant defense in the absence of jasmonic acid: the role of cyclopentenones. Proc. Natl. Acad. Sci. USA 98, 12837-12842.
27. Straus, D.S., Glass, C.K., 2001. Cyclopentenone prostaglandins: new insights on biological activities and cellular targets. Med. Res. Rev. 21, 185-210.