Characterization and quantification of free and esterified 9- and 13-hydroxyoctadecadienoic acids (HODE) in barley, germinating barley, and finished malt

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 5, 2005, Pages 1556-1562

  Hobke, Holger ^a   Garbe, Leif Alexander ^a   Tressl, Roland ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Analysis; Barley; Enantiomers; Green malt; HODE; Lipoxygenase; Malt; Polar lipids

Indexed keywords

13 HYDROXYOCTADECADIENOIC ACID; 9 HYDROXYOCTADECADIENOIC ACID; LIPID; LIPOXYGENASE; TRIACYLGLYCEROL; UNCLASSIFIED DRUG;

ARTICLE; AUTOOXIDATION; BARLEY; CATALYSIS; ENANTIOMER; ENZYME ACTIVITY; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MALT; MASS SPECTROMETRY; NONHUMAN;

CEREALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ESTERIFICATION; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GERMINATION; HORDEUM; LINOLEIC ACIDS; LINOLEIC ACIDS, CONJUGATED; SEEDS; STEREOISOMERISM;

HORDEUM VULGARE SUBSP. VULGARE;

EID: 14644396523     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf048490s     Document Type: Article

References (41)

1. Feussner, I.; Kindl, H. A lipoxygenase is the main lipid body protein in cucumber and soybean cotyledons during the stage of triglyceride mobilization. FEBS Lett. 1992, 298, 223-225.
2. Matthew, J. A.; Chan, H. W.-S.; Galliard, T. A simple method for the preparation of pure 9-D-hydroperoxide of linoleic acid and methyl linoleate based on the positional specifity of lipoxygenase in tomato fruit. Lipids 1977, 12, 324-326.
3. Göbel, C.; Feussner, I.; Schmidt, A.; Scheel, D.; Sanchez-Serrano, J.; Hamberg, M.; Rosahl, S. Oxylipin profiling reveals the preferential stimulation of the 9-lipoxygenase pathway in elicitor-treated potato cells. J. Biol. Chem. 2001, 276, 6267-6273.
4. Zhang, L.-Y.; Hamberg, M. Specificity of two lipoxygenases from rice: Unusual regiospecificity of a lipoxygenase isoenzyme. Lipids 1996, 31, 803-809.
5. Blee, E. Phytooxylipins and plant defense reactions. Prog. Lipid Res. 1998, 37, 33-72.
6. Galliard, T.; Phillips, D. R. The enzymatic conversion of linoleic acid into 9-(nona-1′,3′-dienoxy)non-8-enoic acid, a novel unsaturated ether derivate isolated from homogenates of Solanum tuberosum tubers. Biochem. J. 1972, 129, 743-753.
7. Galliard, T.; Phillips, D. R. Novel divinyl ether fatty acids in extracts of Solanum tuberosum. Chem. Phys. Lipids 1973, 11, 173-180.
8. Grechkin, A. N.; Ilyasov, A. V., Hamberg, M. On the mechanism of biosynthesis of divinyl ether oxylipins by enzyme from garlic bulbs. Eur. J. Biochem. 1997, 245, 137-142.
9. Hamberg, M.; Gardner, H. W. Oxylipin pathway to jasmonates: biochemistry and biological significance. Biochim. Biophys. Acta 1992, 1165, 1-18.
10. Noordermeer, M. A.; Veldink, G. A.; Vliegenthart, J. F. G. Fatty acid hydroperoxide lyase: A plant cytochrome P450 enzyme involved in wound healing and pest resistance. ChemBioChem 2001, 2, 494-504.
11. Hamberg, M. An epoxy alcohol synthase in higher plants: Biosynthesis of antifungal trihydroxy oxylipins in leaves of potato. Lipids 1999, 34, 1131-1142.
12. Franke, W.; Freshe, H. Autoxidation of unsaturated fatty acids VI. The lipoxidase of cereals in particular barley. Hoppe Seyler's Z. Physiol. Chem. 1953, 295, 333-349.
13. Graveland, A.; Pesman, L.; Van Eerde, P. Enzymatic oxidation of linoleic acid in barley suspensions. Tech. Q. Master Brew. Assoc. Am. 1972, 9, 98-104.
14. Führling, D. Lipoxygenase und Linolsäurehydroperoxid-Isomerase in Gerste (Hordeum vulgare). Ph.D. Thesis, Technische Universität Berlin, Germany, 1975.
15. Yabuuchi, S.; Amaha, M. Partial purification and characterization of lipoxygenase from grains of Hordeum distichum. Phytochemistry 1975, 14, 2569-2572.
16. Yabuuchi, S. Occurrence of a new lipoxygenase isoenzyme in germinating barley embryos. Agric. Biol. Chem. 1976, 40, 1987-1992.
17. Baxter, E. D. Lipoxidases in malting and mashing. J. Inst. Brew. 1982, 88, 390-396.
18. Doderer, A.; Kokkelink, I.; van der Veen, S.; Valk, B. E.; Schram, A. W.; Douma, A. C. Purification and characterization of two lipoxygenase isoenzymes from germinating barley. Biochim. Biophys. Acta 1992, 1120, 97-104.
19. Yang, G.; Schwarz, P. B.; Vick, B. A. Purification and characterization of lipoxygenase isoenzymes in germinating barley. Cereal Chem. 1993, 70, 589-595.
20. Hugues, M.; Boivin, P.; Gauillard, F.; Nicolas, J.; Thiry, J. M.; Richard-Forget, F. Two lipoxygenases from germinated barley-heat and kilning stability. J. Food Sci. 1994, 59, 885-889.
21. Holtman, W. L.; Vredenbregt-Heistek, J. C.; Schmitt, N. F.; Feussner, I. Lipoxygenase-2 oxygenates storage lipids in embryos of germinating barley. Eur. J. Biochem. 1997, 248, 452-458.
22. van Aarle, P. G. M.; de Barse, M. J.; Veldink, G. A.; Vliegenthart, J. F. G. Purification of a lipoxygenase from ungerminated barley: Characterization and product formation. FEBS Lett. 1991, 280, 159-162.
23. Bundy, G. L.; Nidy, E. G.; Epps, D. E.; Mizsak, S. A.; Wnuk, R. J. Discovery of an arachidonic acid C-8 lipoxygenase in the gorgonian coral Pseudoplexaura porosa. J. Biol. Chem. 1986, 261, 747-751.
24. Meijer, L.; Brash, A. R.; Bryant, R. W.; Ng, K.; Maclouf, J.; Sprecher, H. Stereospecific induction of starfish oocyte maturation by (8R)-hydroxyeicosatetraenoic acid. J. Biol. Chem. 1986, 261, 17040-17047.
25. Brash, A. R.; Boeglin, W. E.; Chang, M. S.; Shieh, B. H. Purification and molecular cloning of an 8R-lipoxygenase from the coral Plexaura homomalla reveal the related primary structures of R- and S-lipoxygenases. J. Biol. Chem. 1996, 271, 20949-20957.
26. Schneider, C.; Brash, A. R. Lipoxygenase-catalyzed formation of R-configuration hydroperoxides. Prostaglandins Other Lipid Mediators 2002, 68-69, 291-301.
27. Funk, M. O.; Andre, J. C.; Otsuki, T. Oxygenation of trans polyunsaturated fatty acids by lipoxygenase reveals steric features of the catalytic mechanismen. Biochemistry 1987, 26, 6880-6884.
28. Holtman, W. L.; Van Duijn, G.; Sedee, N. J. A.; Douma, A. C. Differential expression of lipoxygenase isoenzymes in embryos of germinating barley. Plant Physiol. 1996, 111, 569-576.
29. Farmer, E. E.; Ryan, C. A. Octadecanoid precursors of jasmonic acid activate the synthesis of wound-inducible proteinase inhibitors. Plant Cell 1992, 4, 129-134.
30. Feussner, I.; Wasternack, C.; Kindl, H.; Kühn, H. Lipoxygenase-catalyzed oxygenation of storage lipids is implicated in lipid mobilization during germination. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 11849-11853.
31. Feussner, I.; Kühn, H.; Wasternack, C. Do specific linoleate 13-lipoxygenases initiate b-oxidation? FEBS Lett. 1997, 406, 1-5.
32. Weber, H.; Chételat, A.; Caldelari, D.; Farmer, E. E. Divinyl ether acid synthesis in late blight-diseased potato leaves. Plant Cell 1999, 11, 485-493.
33. Martini, D.; Iacazio, G. Enantiomeric separation of various lipoxygenase derived monohydroxy polyunsaturated fatty acid methyl esters by high-performance liquid chromatography. J. Chromatogr. A 1997, 790, 235-241.
34. Simpson, T. D.; Gardner, H. W. Conversion of 13(S)-hydroperoxy-9(Z), 11(E)-octadecadienoic acid to the corresponding hydroxy fatty acid by KOH-A kinetic study. Lipids 1993, 28, 325-330.
35. Gardner, H. W.; Simpson, T. D.; Hamberg, M. Transformation of fatty acid hydroperoxides by alkali and characterization of products. Lipids 1993, 28, 487-495.
36. Gardner, H. W.; Simpson, T. D.; Hamberg, M. Mechanism of linoleic acid hydroperoxide reaction with alkali. Lipids 1996, 31, 1023-1028.
37. Tolbert, N. E. Metabolic pathway in peroxisomes and glyoxysomes. Annu. Rev. Biochem. 1981, 50, 133-157.
38. Filppula, S. A.; Sormunen, R. T.; Hartig, A.; Kunau, W. H.; Hiltunen, J. K. Changing stereochemistry for a metabolic pathway in vivo. J. Biol. Chem. 1995, 270, 27453-27457.
39. Behrends, W.; Thieringer, R.; Engeland, K.; Kunau, W. H.; Kindl, H. The glyoxysomal β-oxidation system in cucumber seedlings: Identification of enzymes required for the degradation of unsaturated fatty acids. Arch. Biochem. Biophys. 1988, 263, 170-177.
40. Yang, G.; Schwarz, P. B. Activity of lipoxygenase isoenzymes during malting and mashing. J. Am. Soc. Brew. Chem. 1995, 53, 45-49.
41. Hamberg, M. Regio- and stereochemical analysis of trihydroxy-octadecenoic acids derived from linoleic acid 9- and 13-hydroperoxides Lipids 1991, 26, 407-415.