Enantioselective formation pathway of a trihydroxy fatty acid during mashing

Journal of the American Society of Brewing Chemists

Volumn 63, Issue 4, 2005, Pages 157-162

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

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

2E nonenal; Analysis; Enantiomer; Lipoxygenase; Wort

Indexed keywords

HORDEUM VULGARE SUBSP. VULGARE;

EID: 28144463064     PISSN: 03610470     EISSN: None     Source Type: Journal    
DOI: 10.1094/ASBCJ-63-0157     Document Type: Article

References (22)

1. Brash, A. R., Baertschi, S. W., Ingram, C. D., and Harris, T. M. Isolation and characterization of natural allene oxides - unstable intermediates in the metabolism of lipid hydroperoxides. Proc. Natl. Acad. Sci. USA 85:3382-3386, 1988.
2. Dix, T. A., and Marnett, L. J. Conversion of linoleic acid hydroperoxide to hydroxy, keto, epoxyhydroxy, and trihydroxy fatty acids by hematin. J. Biol. Chem. 260:5351-5357, 1985.
3. Funk, M. O., Isaac, R., and Porter, N. A. Preparation and purification of lipid hydroperoxides from arachidonic and γ-linolenic acids. Lipids 11:113-117, 1976.
4. Garbe, L.-A., Hübke, H., and Tressl, R. Oxygenated fatty acids and flavour stability. (CD-Rom) Proc. Congr. Eur. Brew. Conv. 29:69, 2003.
5. Garbe, L.-A., Lange, H., and Tressl, R. Biosynthesis of γ-nonalactone in yeast In: Aroma Active Compounds in Foods. Chemistry and Sensory Properties. G. R. Takeoka, M. Güntert, and K.-H. Engel, Eds. American Chemical Society Series No. 794. Pp. 176-182, 2001.
6. Garbe, L.-A., and Tressl, R. Metabolism of deuterated isomeric 6,7-dihydroxydodecanoic acids in Saccharomyces cerevisiae - diastereo-and enantioselective formation and characterization of 5-hydroxydecano-4-lactone (=4,5-dihydro-5(1-hydroxyhexyl)furan-2(3H)-one) isomers. Helv. Chim. Acta 86:2349-2363, 2003.
7. Gardner, H. W. Isolation of pure isomer of linoleic acid hydroperoxide. Lipids 10:248-252, 1975.
8. Hamberg, M. Trihydroxyoctadecenoic acids in beer - qualitative and quantitative analysis. J. Agric. Food Chem. 39:1568-1572, 1991.
9. Hamberg, M. A pathway for biosynthesis of divinyl ether fatty acids in green leaves. Lipids 33:1061-1071, 1998.
10. Hamberg, M., and Hamberg, G. Peroxygenase-catalyzed fatty acid epoxidation in cereal seeds - sequential oxidation of linoleic acid into 9(S),12(S),13(S)-trihydroxy-10(E)-octadecenoic acid. Plant Physiol. 110:807-815, 1996.
11. Holtman, W. L., Vredenbregt-Heistek, J. C., Schmitt, N. F., and Feussner, I. Lipoxygenase-2 oxygenates storage lipids in embryos of germinating barley. Eur. J. Biochem. 248:452-458, 1997.
12. Hübke, H., Untersuchung von glycerid-und phosphoglycerid-gebundenen oxygenierten fettsäuren in malz und bier. Ph.D. thesis, Technische Universität. Berlin, Germany, 2003.
13. Hübke, H., Garbe, L.-A., and Tressl, R. Characterization and quantification of free- and esterified 9- and 13-hydroxyoctadecadienoic acids (HODE) in barley, germinating barley and in finished malt. J. Agric. Food Chem. 53:1556-1562, 2005.
14. Hugues, M., Boivin, P., Gauillard, F., Nicolas, J., Thiry, J. M., and Richard-Forget, F. Two lipoxygenases from germinated barley - heat and kilning stability. J. Food Sci. 59:885-889, 1994.
15. Masui, H., Kondo, T., and Kojima, M. An antifungal compound, 9,12,13-trihydroxy-(E)-10-octadecenoic acid, from Colocasia antiquorum inoculated with Ceratocystis fimbriata. Phytochemistry 28:2613, 1989.
16. Matthew, J. A., Chan, H. W.-S., and Gaillard, 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 12:324-326, 1977.
17. Möller-Hergt, G., Wackerbauer, K., Tressl, R., Garbe, L.-A., and Zufall, C. Die Hydroxyfettsäuren in Würze und Bier. Proc. Congr. Eur. Brew. Conv. 27:123-132, 1999.
18. Nagai, T., Kiyohara, H., Munakata, K., Shirahata, T., Sunazuka, T., Harigaya, Y., and Yamada, H. Pinellic acid from the tuber of Pinellia ternate Breitenbach as an effective oral adjuvant for nasal influenza vaccine. Int. Immunopharmacol. 2:1183-1193, 2002.
19. Noordermeer, M. A., Veldink, G. A., and Vliegenthart, F. G. Fatty acid hydroperoxide lyase: A plant cytochrome P450 enzyme involved in wound healing and pest resistance. Chem. Biochem 2:494-504, 2001.
20. Schulz, H. Untersuchungen zum enzymatischen abbau von hydroperoxydierten fettsäuren. Ph. D. thesis, Technische Universität Berlin, Germany, 2002.
21. Wackerbauer, K., and Meyna, S. Free and triglyceride-bonded hydroxy fatty acids in barley and malt. I. Influence of variety, provenience and harvest year. Monatsschr. Brauwiss. 55:52-57, 2002.
22. Yang, G., Schwarz, P. B., and Vick, B. A. Purification and characterization of lipoxygenase isoenzymes in germinating barley. Cereal Chem. 70:589-595, 1993.