New cyclopentenone fatty acids formed from linoleic and linolenic acids in potato

Lipids

Volumn 35, Issue 4, 2000, Pages 353-363

  Hamberg, Mats ^a  

^a KAROLINSKA INSTITUTE   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; CYCLOPENTENONE; FATTY ACID; JASMONIC ACID; KETOL; LINOLEIC ACID; LINOLENIC ACID; LIPOXYGENASE; OCTANOIC ACID DERIVATIVE; STEARIC ACID DERIVATIVE; SYNTHETASE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; ENZYME ACTIVITY; FATTY ACID SYNTHESIS; HOMOGENATE; HYDROLYSIS; NONHUMAN; PLANT GROWTH; PLANT ROOT; POTATO; RACEMIC MIXTURE; STEREOSPECIFICITY;

EID: 0034022757     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-000-532-z     Document Type: Article

References (27)

1. Creelman, R.A., and Mullet, J.E. (1997) Biosynthesis and Action of Jasmonates in Plants, Annu. Rev. Plant Physiol. Plant Mol. Biol. 48, 355-381.
2. Vick, B.A., and Zimmerman, D.C. (1983) The Biosynthesis of Jasmonic Acid: A Physiological Role for Plant Lipoxygenase, Biochem. Biophys. Res. Commun. 111, 470-477.
3. Mueller, M.J. (1997) Enzymes Involved in Jasmonic Acid Biosynthesis, Physiol. Plant. 100, 653-663.
4. Grechkin, A. (1998) Recent Developments in Biochemistry of the Plant Lipoxygenase Pathway. Prog. Lipid Res. 37, 317-352.
5. Ziegler, J., Wasternack, C., and Hamberg, M. (1999) On the Specificity of Allene Oxide Cyclase. Lipids 34, 1005-1015.
6. Weber, H., Vick, B.A., and Farmer, E.E. (1997) Dinor-oxo-phytodienoic Acid: A New Hexadecanoid Signal in the Jasmonate Family. Proc. Natl. Acad. Sci. USA 94, 10473-10478.
7. Matthew, J.A., Chan, H.W.-S., and Galliard, T. (1977) A Simple Method for the Preparation of Pure 9-D-Hydroperoxide of Linoleic Acid and Methyl Linoleate Based on the Positional Specificity of Lipoxygenase in Tomato Fruit, Lipids 12, 324-326.
8. Hamberg, M. (1987) Mechanism of Corn Hydroperoxide Isomerase: Detection of 12,13(S)-Oxido-9(Z),11-octadecadienoic Acid. Biochim. Biophys. Acta 920, 76-84.
9. Hamberg, M., and Hughes, M.A. (1988) Biosynthesis and Conversions of Fatty Acid Allene Oxides, in Advances in Prostaglandin, Thromboxane, and Leukotriene Research (Samuelsson, B., Wong, P.Y.-K., and Sun, F.F., eds.), Vol. 19, pp. 64-69, Raven Press, New York.
10. Hamberg, M. (1988) Fatty Acid Allene Oxides II. Formation of Two Macrolactones from 12,13(S)-Epoxy-9(Z),11-octadecadienoic Acid, Chem. Phys. Lipids 46, 235-243.
11. Hamberg, M., Miersch, O., and Sembdner, G. (1988) Absolute Configuration of 12-Oxo-10, 15(Z)-phytodienoic Acid, Lipids 23, 521-524.
12. Hamberg, M., and Hughes, M.A. (1988) Fatty Acid Allene Oxides. III. Albumin-Induced Cyclization of 12, 13(S)-Epoxy-9(Z), 11-octadecadienoic Acid, Lipids 23, 469-475.
13. Hamberg, M. (1999) An Epoxy Alcohol Synthase Pathway in Higher Plants: Biosynthesis of Antifungal Trihydroxy Oxylipins in Leaves of Potato, Lipids 34, 1131-1142.
14. Galliard, T., and Phillips, D.R. (1972) The Enzymic Conversion of Linoleic Acid into 9-(nona-1′,3′-dienoxy)Non-8-enoic Acid, a Novel Unsaturated Ether Derivative Isolated from Homogenates of Solaman tuberosum Tubers. Biochem. J. 129, 743-753.
15. Hamberg, M., and Fahlstadius, P. (1990) Allene Oxide Cyclase: A New Enzyme in Plant Lipid Metabolism. Arch. Biochem. Biophys. 276, 518-526.
16. Hamberg, M. (1998) A Pathway for Biosynthesis of Divinyl Ether Fatty Acids in Green Leaves, Lipids 33, 1061-1071.
17. Baertschi, S.W., Ingram, C.D., Harris, T.M., and Brash, A.R. (1988) Absolute Configuration of cis-12-Oxophytodienoic Acid of Flaxseed: Implications for the Mechanism of Biosynthesis from the 13(S)-Hydroperoxide of Linolenic Acid, Biochemistry 27, 18-24.
18. Zimmerman, D.C., and Feng, P. (1978) Characterization of a Prostaglandin-Like Metabolite of Linolenic Acid Produced by a Flaxseed Extract, Lipids 13, 313-316.
19. Vick, B.A., Zimmerman, D.C., and Weisleder, D. (1979) Thermal Alteration of a Cyclic Fatty Acid Produced by a Flaxseed Extract. Lipids 14, 734-740.
20. Anteunis, M., and Danneels, D. (1975) Stereochemical Aspects of Proton Chemical Shifts III. Configurational Assignments in Pentacyclic Systems Without Recourse to a Karplus Equation, Org. Magn. Reson. 7, 345-348.
21. Abian, J., Gelpi, E., and Pages, M. (1991) Effect of Abscisic Acid on the Linoleic Acid Metabolism in Developing Maize Embryos, Plant Physiol. 95, 1277-1283.
22. Grechkin, A.N., Kurumshin, R.A., Safonova, E.Y., Latypov, S.K., and Ilyasov, A.V. (1991) Formation of Ketols from Linolenic Acid 13-Hydroperoxide via Allene Oxide. Evidence for Two Distinct Mechanisms of Allene Oxide Hydrolysis, Biochim. Biophys. Acta 1086, 317-325.
23. Brash, A.R., Baertschi, S.W., Ingram, C.D., and Harris, T.M. (1988) Isolation and Characterization of Natural Allene Oxides: Unstable Intermediates in the Metabolism of Lipid Hydroperoxides, Proc. Natl. Acad. Sci. USA 85, 3382-3386.
24. Gardner, H.W. (1970) Sequential Enzymes of Linoleic Acid Oxidation in Corn Germ: Lipoxygenase and Linoleate Hydroperoxide Isomerase. J. Lipids Res. 11, 311-321.
25. 18O]-Hydroperoxylinolenic Acid by Hydroperoxide Cyclase. Lipids 15, 468-471.
26. Grechkin, A.N., and Hamberg, M. (1999) Formation of Cyclopentenones from All-(E) Hydroperoxides of Linoleic Acid via Allene Oxides. New Insight into the Mechanism of Cyclization. FEBS Lett. 466, 63-66.
27. Grechkin, A.N. (1994) Cyclization of Natural Allene Oxide Fatty Acids. The Anchimeric Assistance of β,γ-Double Bond Beside the Oxirane and the Reaction Mechanism. Biochim. Biophys. Acta 1213, 199-206.