Hydroperoxide lyase; lipoxygenase pathway; fatty acid hydroperoxides; linoleic acid; linolenic acid; short chain; aldehydes; 1-octen-3-ol; green note compounds
Abstract :
[en] The hydroperoxide lyase belongs to the lipoxygenase pathway, pathway in which polyunsaturated fatty acids are transformed into a large spectrum of compounds with various chemical and biological functions. The hydroperoxide lyase acts on fatty acids hydroperoxides (mainly linoleic and linolenic). It cleaves the bond between carbon carrying the hydroperoxide function and a vicinal carbon giving an w-oxo-acid and also depending on the species, an aldehyde, a hydrocarbon or an alcohol.
Andrianarison RH., Beneytout JL., Tixier M. (1989). An enzymatic conversion of lipoxygenase products by a hydroperoxide lyase in Blue-Green Algae (Oscillatoria sp.). Plant Physiol. 91, p. 1280–1287.
Angerosa F., Camera L., d’Alessandro N., Mellerio G. (1998). Characterization of seven new hydrocarbon compounds present in the aroma of virgin olive oils. J. Agric. Food Chem. 46, p. 648–653.
Assaf S., Hadar Y., Dosoretz CG. (1997). 1-octen-3-ol and 13-hydroperoxylinoleate are products of distinct pathways in the oxidative breakdown of linoleic acid by Pleurotus pulmonarius. Enzyme Microb. Technol. 21, p. 484–490.
Bate NJ., Sivasankar S., Moxon C., Riley J M C., Thompson JE., Rothstein SJ. (1998). Molecular characterization of an Arabidopsis gene encoding hydroperoxide lyase, a cytochrome P-450 that is wound inducible. Plant Physiol. 117, p. 1393–1400.
Berger RG., Kler A., Drawert F. (1986). The C6-aldehydeforming system in Agropyron repens. Biochim. Biophys. Acta 883, p. 523–530.
Blée E., Joyard J. (1996). Envelope membranes from spinach chloroplasts are a site of metabolism of fatty acid hydroperoxides. Plant Physiol. 110, p. 445–454.
Croft KPC., Jüttner F., Slusarenko AJ. (1993). Volatile products of the lipoxygenase pathway evolved from Phaseolus vulgaris (L.) leaves inoculated with Pseudomonas syringae pv phaseolicola. Plant Physiol. 101, p. 13–24.
Deng W., Hamilton-Kemp TR., Nielsen M T., Andersen R A., Collins GB., Hildebrand DF. (1993). Effects of sixcarbon aldehydes and alcohols on bacterial proliferation. J. Agric. Food Chem. 41, p. 506–510.
Fauconnier ML. (1997). Contribution à l’étude de la p roduction du (E)-hex-2-ènal naturel par synthèse enzymatique. Thèse de doct. sci. agron., Fac. univ. Sci. agron., Gembloux (Belgique) 291 p.
Fauconnier ML., Marlier M. (1997). Revue bibliographique: les lipoxygénases du soja. Biotechnol. A g ron. Soc. Environ. 1 (2), p. 125–141.
Fauconnier ML., Perez AG., Sanz C., Marlier M. (1997). Purification and characterization of tomato leaf (Lycopersicon esculentum Mill.) hydroperoxyde lyase. J. Agric. Food Chem. 45 (11), p. 4232–4236.
Galliard T., Phillips DR. (1976). The enzymatic cleavage of linoleic acid to C9 carbonyl fragments in extracts of cucumber (Cucumis sativus) fruit and the possible role of lipoxygenase. Biochim. Biophys. Acta 431, p. 278–287.
Gamage P T., Matsushita S. (1973). Interactions of autoxidized products of linoleic acid with enzyme proteins. Agric. Biol. Chem. 37 (1), p. 1–8.
Gardner HW. (1979). Lipid hydroperoxide reactivity with proteins and amino acids: a review. J. Agric. Food Chem. 27, p. 220–229.
Gardner H W. (1991). Recent investigations into the lipoxygenase pathway of plants. Biochim. Biophys. Acta 1084, p. 221–239.
Gardner H W., Plattner RD. (1984). Linoleate hydroperoxides are cleaved heterotically into aldehydes by a Lewis acid in aprotic solvent. Lipids 19 (4), p. 294–299.
Gardner H W., Weisleder D., Plattner RD. (1991). Hydroperoxide lyase and other hydroperoxidemetabolizing activity in tissues of soybean, Glycine max. Plant Physiol. 97, p. 1059–1072.
Gargouri M., Legoy MD. (1998). Biosynthesis and analysis of 3Z-nonenal. Biotechnol. Lett. 20 (1), p. 23–26.
Garssen GJ., Vliegenthart JFG., Boldingh J. (1971). A n anaerobic reaction between lipoxygenase, linoleic acid and its hydroperoxides. Biochem. J. 122, p. 327–332.
Grechkin AN., Ilyasov AV., Hamberg M. (1997). On the mechanism of biosynthesis of divinyl ether oxylipins by enzyme from garlic bulbs. Eur. J. Biochem. 245, p. 137–142.
Hatanaka A. (1993). The biogeneration of green odour by green leaves. Phytochemistry 34 (5), p. 1201–1218.
Hatanaka A., Kajiwara T., Harada T. (1975). Biosynthetic pathway of cucumber alcohol: trans-2,cis-6-nonadienol via cis- 3,cis-6-nonadienal. Phytochemistry 14, p. 2589–2592.
Hatanaka A., Sekiya J., Kajiwara T., Munechika K. (1982a). Natural inhibitor for volatile C6- aldehyde formation from C18-unsaturated fatty acids. Agric. Biol. Chem. 43 (11), p. 2705–2710.
Hatanaka A., Kajiwara T., Sekiya J., Inouye S. (1982b). Solubilization and properties of the enzyme-cleaving 13-L-hydroperoxylinolenic acid in tea leaves. Phytochemistry 21 (1), p. 13–17.
Itoh A., Vick BA. (1999). The purification and characterization of fatty acid hydroperoxide lyase in sunflower. Biochim. Biophys. Acta 1436, p. 531–540.
Kim IS., Grosch W. (1981). Partial purification of a hydroperoxide lyase from fruits of pear. J. Agric. Food Chem. 29, p. 1220–1225.
Kondo Y., Hashidoko Y., Mizutani J. (1995). An enzymatic formation of 13-oxo-trideca-9,11-dienoic acid from 13-hydroperoxylinolenic acid by homolytic hydroperoxide lyase in elicitor-treated soybean cotyledons. Biochim. Biophys. Acta 1255, p. 9–15.
Lau SMC., Harder PA., O’Keefe DP. (1993). Low carbon monoxide affinity allene oxide synthase is the predominant cytochrome P450 in many plant tissues. Biochemistry 32, p. 1945–1950.
Matsui K., Shibata Y., Kajiwara T., Hatanaka A. (1989). Separation of 13- and 9-hydroperoxide lyase activities in cotyledons of cucumber seedlings. Z. Naturforsch. 44c, p. 883–885.
Matsui K., Toyota H., Kajiwara T., Kakuno T., Hatanaka A. (1991). Fatty acid hydroperoxide cleaving enzyme, hydroperoxide lyase, from tea leaves. Phytochemistry 30 (7), p. 2109–2113.
Matsui K., Kajiwara T., Hatanaka A. (1992). Inactivation of tea leaf hydroperoxide lyase by fatty acid hydroperoxide. J. Agric. Food Chem. 40, p. 175–178.
Matsui K., Shibutani M., Hase T., Kajiwara T. (1996). Bell pepper fruit fatty acid hydroperoxide lyase is a cytochrome P450 (CYP74B). FEBS Lett. 394, p. 21–24.
Matsui K., Shibata Y., Tateba H., Hatanaka A., Kajiwara T. (1997). Changes of lipoxygenase and fatty acid hydroperoxide lyase activities in bell pepper fruits during maturation. Biosci. Biotech. Biochem. 61 (1), p. 199–201.
Matthew JA., Galliard T. (1978). Enzymatic formation of carbonyls from linoleic acid in leaves of Phaseolus vulgaris. Phytochemistry 17, p. 1043–1044.
Mau JL., Beelman RB., Ziegler G. (1992). 1-octen-3-ol in the cultivated mushroom, Agaricus bisporus. J. Food Sci. 57 (3), p. 704–706.
Noordermeer MA., Veldink GA., Vliegenthart JFG. (1999). Alfalfa contains substantial 9-hydroperoxide lyase activity and a 3Z:2E-enal isomerase. FEBS Lett. 443, p. 201–204.
Nunez A., Foglia TA., Piazza GJ. (1998). Agas chromatographic-mass spectrometric method using poraPLOT column for the detection of hydroperoxide lyase in Chlorella pyrenoidosa. Lipids 33 (5), p. 533–538.
Olias JM., Rios JJ., Valle M., Zamora R., Sanz L C., Axelrod B. (1990). Fatty acid hydroperoxide lyase in germinating soybean seedlings. J. Agric. Food Chem. 38, p. 624–630.
Pan Z., Durst F., Werck-Reichhart D., Gardner H W., Camara B., Cornish K., Backhaus RA. (1995). The major protein of Guayule Rubber Particles is a cytochrome P450. J. Biol. Chem. 270 (15), p. 8487–8494.
Phillips DR., Galliard T. (1978). Flavour biogenesis. Partial purification and properties of a fatty acid hydroperoxide cleaving enzyme from fruits of cucumber. Phytochemistry 17, p. 355–358.
Rota C., Barr DP., Martin MV., Guengerich FP., Tomasi A., Manson RP. (1997). Detection of free radicals produced from the reaction of cytochrome P-450 with linoleic acid hydroperoxide. Biochem. J. 323, p. 565–571.
Salch YP., Grove MJ., Takamura H., Gardner HW. (1995). Characterization of a C-5,13-cleaving enzyme of 13(S)-hydroperoxide of linolenic acid by soybean seed. Plant Physiol. 180, p. 1211–1218.
Sanz C., Olias JM., Perez AG. (1997). Aroma biochemistry of fruits and vegetables. In Tomas-Barberan FA., Robins RJ. (eds). Phytochemistry of fruit and vegetables. Oxford: Clarendon Press, p. 125–155.
Schreier P., Lorenz G. (1982). Separation, partial purification and characterisation of a fatty acid hydroperoxide cleaving enzyme from apple and tomato fruits. Z. Naturforsch. 37c, p. 165–173.
Sekiya J., Kamiuchi H., Hatanaka A. (1982). Lipoxygenase, hydroperoxide lyase and volatile C6-aldehyde formation from C18-fatty acids during development of Phaseolus vulgaris L. Plant. Cell Physiol. 23 (4), p. 631–638.
Sekiya J., Tanigawa S., Kajiwara T., Hatanaka A. (1984). Fatty acid hydroperoxide lyase in tobacco cells cultured in vitro. Phytochemistry 23 (11), p. 2439–2443.
Shibata Y., Matsui K., Kajiwara T., Hatanaka A. (1995a). Fatty acid hydroperoxide lyase is a heme protein. Biochem. Biophys. Res. Commun. 207 (1), p. 438–443.
Shibata Y., Matsui K., Kajiwara T., Hatanaka A. (1995b). Purification and properties of fatty acid hydroperoxide lyase from green bell pepper fruits. Plant Cell Physiol. 36, p. 147–156.
Song WC., Funk CD., Brash AR. (1993). Molecular cloning of an allene oxide synthase: a cytochrome P450 specialized for the metabolism of fatty acid hydroperoxides. P roc. Natl. Acad. Sci. USA. 90, p. 8519–8523.
Strong FE., Kruitwagen E. (1967). Traumatic acid: an accelerator of abscission in cotton explants. Nature 215, p. 1380–1381.
Treshow M. (1955). Physiology and anatomical development of tomato fruit tumor. Am. J. Bot. 42, p. 198–202.
Tressl R., Bahri D., Engel KH. (1982). Formation of eightcarbon and ten-carbon components in mushrooms (Agaricus campestris). J. Agric. Food Chem. 30, p. 89–93.
Vaz ADN., Coon MJ. (1987). Hydrocarbon formation in the reductive cleavage of hydroperoxides by cytochrome P-450. Proc. Natl. Acad. Sci. USA 84, p. 1172–1176.
Vaz ADN., Roberts ES., Coon MJ. (1990). Reductive b-scission of the hydroperoxides of fatty acids and xenobiotics: Role of alcool-inducible cytochrome P-450. Proc. Natl. Acad. Sci. USA 87, p. 5499–5503.
Vick BA., Zimmerman DC. (1976). Lipoxygenase and hydroperoxide lyase in germinating watermelon seedlings. Plant Physiol. 57, p. 780–788.
Vick BA., Zimmerman DC. (1987). Pathways of fatty acid hydroperoxide metabolism in spinach leaf chloroplasts. Plant Physiol. 85, p. 1073–1078.
Vick BA., Zimmerman DC. (1989). Metabolism of fatty acid hydroperoxides by Chlorella pyrenoidosa. Plant Physiol. 90, p. 125–132.
Weber H., Chételat A., Caldelari D., Farmer EE. (1999). Divinyl ether fatty acid synthesis in late blight-diseased potato leaves. Plant Cell 11, p. 485–493.
Wurzenberger M., Grosch W. (1984). The formation of 1-octen-3-ol from the 10-hydroperoxide isomer of linoleic acid by a hydroperoxide lyase in mushroom (Psalliota bispora). Biochim. Biophys. Acta 794, p. 25–30.
Wurzenberger M., Grosch W. (1986). Enzymatic oxidation of linolenic acid to 1, Z-5-octadien-3-ol, Z-2, Z-5-octadien-1-ol and 10-oxo-E-8-decenoic acid by a protein fraction from mushrooms (Psalliota bispora). Lipids 21 (4), p. 261–266.
Zimmerman DC., Coudron CA. (1979). Identification of traumatin, a wound hormone, as 12-oxo-10-dodecenoic acid. Plant Physiol. 63, p. 536–541.