Functional characterization of two 13-lipoxygenase genes from olive fruit in relation to the biosynthesis of volatile compounds of virgin olive oil

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 19, 2009, Pages 9097-9107

  Padilla, María N ^a   Hernández, M Luisa ^a   Sanz, Carlos ^a   Martínez Rivas, José M ^a  

^a INSTITUTO DE LA GRASA   (Spain)

Author keywords

Gene expression; Lipoxygenase; Olea europaea; Olive oil; Volatiles

Indexed keywords

13 LIPOXYGENASE; 13-LIPOXYGENASE; LINOLENIC ACID; LIPOXYGENASE; OLIVE OIL; PLANT DNA; RECOMBINANT PROTEIN; VEGETABLE OIL;

AMINO ACID SEQUENCE; ARTICLE; CHEMISTRY; COMPARATIVE STUDY; DNA SEQUENCE; ENZYME SPECIFICITY; ENZYMOLOGY; ESCHERICHIA COLI; FRUIT; GENE EXPRESSION; GENETICS; ISOLATION AND PURIFICATION; METABOLISM; MOLECULAR GENETICS; ODOR; OLIVE TREE; POTATO; SEQUENCE ALIGNMENT; TOMATO; VOLATILIZATION;

ALPHA-LINOLENIC ACID; AMINO ACID SEQUENCE; DNA, PLANT; ESCHERICHIA COLI; FRUIT; GENE EXPRESSION; LIPOXYGENASE; LYCOPERSICON ESCULENTUM; MOLECULAR SEQUENCE DATA; ODORS; OLEA; PLANT OILS; RECOMBINANT PROTEINS; SEQUENCE ALIGNMENT; SEQUENCE ANALYSIS, DNA; SOLANUM TUBEROSUM; SUBSTRATE SPECIFICITY; VOLATILIZATION;

OLEA EUROPAEA;

EID: 70349906721     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf901777j     Document Type: Article

References (47)

1. (1) Visioli, F.; Galli, C. Olive oil phenols and their potential effects on human health. J. Agric. Food Chem. 1998, 46, 4292-4296. (Pubitemid 128488531)
2. Morales, M. T.; Aparicio, R; Ríos, J. J. Dynamic headspace gas chromatographic method for determining volatiles in virgin olive oil. J. Chromatogr., A 1994, 668, 455-462.
3. Angerosa, F.; Mostallino, R.; Basti, C.; Vito, R. Virgin olive oil odour notes: their relationships with the volatile compound from the lipoxygenase pathway and secoiridoid compounds. Food Chem. 2000, 68, 283-287.
4. Olías, J. M.; Pérez, A. G.; Rios, J. J.; Sanz, C. Aroma of virgin olive oil: biogenesis of the green odor notes. J. Agric. Food Chem. 1993, 41, 2368-2373.
5. (5) Salas, J. J.; Williams, M.; Harwood, J. L.; Sánchez, J. Lipoxygenase activity in olive (Olea europaea) fruit. J. Am. Oil Chem. Soc. 1999, 76, 1163-1169. (Pubitemid 30528822)
6. (6) Salas, J. J.; Sánchez, J. Hydroperoxide lyase from olive (Olea europaea) fruits. Plant Sci. 1999, 143, 19-26. (Pubitemid 29275285)
7. (7) Salas, J. J.; Sánchez, J. Alcohol dehydrogenases from olive (Olea europaea) fruit. Phytochemistry 1998, 48, 35-40. (Pubitemid 28242376)
8. Salas, J. J. Characterization of alcohol acyltransferase from olive fruit. J. Agric. Food Chem. 2004, 52, 3155-3158.
9. Gardner, H. W.; Grove, M. J.; Salch, Y. P. Enzymic pathway to ethyl vinyl ketone and 2-pentenal in soybean preparations. J. Agric. Food Chem. 1996, 44, 882-886.
10. (10) Fisher, A. J.; Grimes, H. D.; Fall, R. The biochemical origin of pentenol emissions from wounded leaves. Phytochemistry 2003, 62, 159-163. (Pubitemid 36857583)
11. Feussner, I.; Wasternack, C. Lipoxygenase pathway. Annu. Rev. Plant Biol. 2002, 53, 275-297.
12. León, J.; Royo, J.; Vancanneyt, G.; Sanz, C.; Silkowski, H.; Griffiths, G.; Sánchez-Serrano, J. J. Lipoxygenase H1 gene silencing reveals a specific role in supplying fatty acid hydroperoxides for aliphatic aldehyde production. J. Biol. Chem. 2002, 277, 416-423.
13. (13) Chen, G. P.; Hackett, R.; Walker, D.; Taylor, A.; Lin, Z. F.; Grierson, D. Identification of a specific isofonn of tomato lipoxygenase (TomloxC) involved in the generation of fatty acid-derived flavour compounds. Plant Physiol. 2004, 136, 2641-2651. (Pubitemid 41071304)
14. Zhang, B.; Yin, X. R.; Li, X.; Yang, S. L.; Ferguson, I. B.; Chen, K. S. Lipoxygenase gene expression in ripening kiwifruit in relation to ethylene and aroma production. J. Agric. Food Chem. 2009, 57, 2875-2881.
15. (15) Sánchez-Ortiz, A.; Pérez, A. G.; Sanz, C. Cultivar differences on nonesterified polyunsaturated fatty acid as a limiting factor for biogenesis of virgin olive oil aroma. J. Agric. Food Chem, 2007, 55, 7869-7873. (Pubitemid 47522200)
16. Luaces, P.; Sanz, C.; Pérez, A. G. Thermal stability of lipoxygenase and hydroperoxide lyase from olive fruit and repercussion on olive oil aroma biosynthesis. J. Agric. Food Chem. 2007, 55, 6309-6313.
17. Williams, M.; Salas, J. J.; Sanchez, J.; Harwood, J. L. Lipoxygenase pathway in olive callus cultures (Olea europaea). Phytochemistry 2000, 53, 13-19.
18. (18) Ridolfi, M.; Terenziani, S.; Patumi, M.; Fontanazza, G. Characterization of the lipoxygenases in some olive cultivars and determination of their role in volatile compounds formation. J. Agric. Food Chem. 2002, 50, 835-839. (Pubitemid 34163631)
19. Williams, M.; Harwood, J. L. Characterisation of lipoxygenase isofonns from olive callus cultures. Phytochemistry 2008, 69, 25322538.
20. Lorenzi, V.; Maury, J.; Casanova, J.; Berti, L. Purification, product characterization and kinetic properties of lipoxygenase from olive fruit (Olea europaea L.). Plant Physiol. Biochem. 2006, 44, 450-454.
21. (21) Haralampidis, K.; Milioni, D.; Sánchez, J.; Baltrusch, M.; Heinz, E.; Hatzopoulos, P. Temporal and transient expression of stearoyl-ACP carrier protein desaturase gene during olive fruit development. J. Exp. Bot. 1998, 49, 1661-1669. (Pubitemid 28465989)
22. Murray, M. G.; Thomson, W. F. Rapid isolation of high weight plant DNA. Nucleic Acids Res. 1980, 8, 4321-11325
23. Hernández, M. L.; Mancha, M.; Martínez-Rivas, J. M. Molecular cloning and characterization of genes encoding two microsomal oleate desaturases (FAD2) from olive. Phytochemistry 2005, 66, 1417-1426.
24. -ΔΔC method. Methods 2001, 25, 402-408.
25. Sanz, L. C.; Perez, A. G.; Rios, J. J.; Olias, J. M. Positional specificity of ketodienes from linoleic acid aerobically formed by lipoxygenase isozymes from kidney bean and pea. J. Agric, Food Chem. 1993, 41, 696-699.
26. Hamberg, M.; Samuelsson, B. On the specificity of the oxygenation of unsaturated fatty acids catalyzed by soybean lipoxygenase. J. Biol. Chem. 1967, 242, 5329-5335.
27. Galliard, T.; Phillips, D. R. Lipoxygenase from potato tubers. Biochem. J. 1971, 124, 431-438.
28. Sanz, L. C.; Pérez, A. G.; Ríos, J. J.; Olías, J. M. Physico-chemical properties of chickpea lipoxygenases. Phytochemistry 1992, 31, 3381-3384.
29. Sánchez, J. Lipid photosynthesis in olive fruit. Prog. Lipid Res. 1994, 33, 97-104.
30. Gavel, Y.; von Heijne, G. A conserved cleavage-site motif in chloroplast transit peptides. FEBS Lett. 1990, 261, 455-458.
31. (31) Fuks, B.; Schnell, D. J. Mechanism of protein transport across the chloroplast envelope. Plant Physiol. 1997, 114 (2), 405-410. (Pubitemid 28378529)
32. Siedow, J. N. Plant lipoxygenase: structure and function. Annu. Rev. Plant Physiol. Plant Mol. Biol. 1991, 42, 145-188.
33. (33) Boyington, J. C.; Gaffney, B. J.; Amzel, L. M. The three-dimensional structure of an arachidonic acid 15-lipoxygenase. Science 1993, 260, 1482-1486. (Pubitemid 23273261)
34. (34) Minor, W.; Steczko, J.; Bolin, J. T.; Otwinowski, Z.; Axelrod, B. Crystallographic determination of the active site iron and its ligands in soybean lipoxygenase L-1. Biochemistry 1993, 32, 6320-6323. (Pubitemid 23208813)
35. (35) Minor, W.; Steczko, J.; Stec, B.; Otwinowski, Z.; Bolin, J. T.; Walter, R.; Axelrod, B. Crystal structure of soybean lipoxygenase L-1 at 1.4 A resolution. Biochemistry 1996, 35, 10687-10701. (Pubitemid 26279648)
36. (36) Sloane, D. L.; Leung, R.; Craik, C. S.; Sigal, E. A primary determinant for lipoxygenase positional specificity. Nature 1991, 354, 149-152. (Pubitemid 21896799)
37. (37) Hornung, E.; Walther, M.; Kühn, H.; Feussner, I. Conversion of cucumber linoleate 13-lipoxygenase to a 9-lipoxygenating species by site-directed mutagenesis. Proc. Natl. Acad. Sci, U.S.A. 1999, 96, 4192-11197 (Pubitemid 29169059)
38. Coffa, G.; Brash, A. R. A single active site residue directs oxygenation stereospecificity in lipoxygenases: stereocontrol is linked to the position of oxygenation. Proc. Natl, Acad. Sci, U.S.A. 2004, 101, 15579-15584.
39. Palmieri-Thiers, C.; Canaan, S.; Brunini, V.; Lorenzi, V.; Tomi, F.; Desseyn, J. L.; Garscha, U.; Oliw, E. H.; Berti, L.; Maury, J. A lipoxygenase with dual positional specificity is expressed in olives (Olea europaea L.) during ripening. Biochim. Biophys. Acta 2009, 1791, 339-346.
40. (40) Chen, X.; Reddanna, P.; Reddy, G. R.; Kidd, R. Expression, purification and characterization of a recombinant 5-lipoxygenase from potato tuber. Biochem, Biophys. Res. Commun. 1998, 243, 438-443. (Pubitemid 28414043)
41. (41) Hughes, R. K.; West, S. I.; Hornostaj, A. R.; Lawson, D. M.; Fairhurst, S. A.; Sanchez, R. O.; Hough, P.; Robinson, B. H.; Casey, R. Probing a novel potato lipoxygenase with dual positional specificity reveals primary determinants of substrate binding and requirements for a surface hydrophobic loop and has implications for the role of lipoxygenases in tubers. Biochem. J. 2001, 353, 345-355. (Pubitemid 32096945)
42. (42) Hughes, R. K.; Wu, Z. C.; Robinson, D. S.; Hardy, D.; West, S. I.; Fairhurst, S. A.; Casey, R. Characterization of authentic recombinant pea-seed lipoxygenases with distinct properties and reaction mechanisms. Biochem. J. 1998, 333, 33-43. (Pubitemid 28342489)
43. Royo, J.; Vancanneyt, G.; Pérez, A. G.; Sanz, C.; Stömiann, K.; Rosahl, S.; Sánchez-Serrano, J. J. Characterization of three potato lipoxygenases with distinct enzymatic activities and different organspecific and wound-regulated expression patterns. J. Biol. Chem. 1996, 271, 21012-21019.
44. Heitz, T.; Bergey, D. R.; Ryan, C. A. A gene encoding a chloroplasttargeted lipoxygenase in tomato leaves is transiently induced by wounding, systemin, and methyl jasmonate. Plant Physiol. 1997, 114, 1085-1093.
45. Loomis, W. D.; Battaille, J. Plant phenolic compounds and the isolation of plant enzymes. Phytochemistry 1966, 5, 423-438.
46. Luaces, P.; Romero, C.; Gutiérrez, F.; Sanz, C.; Pérez, A. G. Contribution of olive seed to the phenolic profile and related quality parameters of virgin olive oil. J. Sci, Food Agric. 2001, 87, 2721-2727.
47. Luaces, P.; Pérez, A. G.; Sanz, C. Role of olive seed in the biogenesis of virgin olive oil aroma. J. Agric. Food Chem. 2003, 51, 4741-4745.