Isolation and characterization of a lipoxygenase from Pseudomonas 42A2 responsible for the biotransformation of oleic acid into (S)-(E)-10-hydroxy-8-octadecenoic acid

Antonie van Leeuwenhoek, International Journal of General and Molecular Microbiology

Volumn 85, Issue 2, 2004, Pages 129-139

  Busquets, M ^a   Deroncele V ^a   Vidal Mas, J ^a   Rodriguez E ^a   Guerrero, A ^b   Manresa, A ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

Author keywords

Absolute configuration; Biotransformation; Hydroxy fatty acids; Lipoxygenase like; Oleic acid; Pseudomonas

Indexed keywords

BROMOBENZOIC ACID DERIVATIVE; HYDROXY FATTY ACID; IRON; LACTATE DEHYDROGENASE; LINOLEIC ACID; LINOLENIC ACID; LIPOXYGENASE; MAGNESIUM ION; OLEIC ACID; OXYGEN; UNSATURATED FATTY ACID;

BIOTRANSFORMATION;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; BIOTRANSFORMATION; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; CONTROLLED STUDY; CULTURE MEDIUM; CYTOPLASM; DECOMPOSITION; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME ISOLATION; ENZYME KINETICS; ENZYME LOCALIZATION; ENZYME SUBSTRATE; IN VIVO STUDY; MOLECULAR WEIGHT; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; POLYACRYLAMIDE GEL ELECTROPHORESIS; PRIORITY JOURNAL; PSEUDOMONAS; TEMPERATURE;

BIOTRANSFORMATION; CELL FRACTIONATION; ELECTROPHORESIS, POLYACRYLAMIDE GEL; ENZYME STABILITY; HYDROGEN-ION CONCENTRATION; KINETICS; LIPOXYGENASE; OLEIC ACID; OLEIC ACIDS; PSEUDOMONAS; THERMODYNAMICS;

PSEUDOMONAS;

EID: 1842789763     PISSN: 00036072     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:ANTO.0000020152.15440.65     Document Type: Article

References (47)

1. Adam W., Lukacs Z., Viebach K., Humpf H.U., Saha-Möller C.R. and Schreier P. 2000. Microscale determination of the absolute configuration of Aryl-substituted alcohols by the CD exciton chirality method. J. Org. Chem. 65: 186-190.
2. Bastida J., de Andrés C., Culleré J., Busquets M. and Manresa A. 1999. Biotransformation of oleic acid into 10-hydroxy-8E-octadecenoic acid by Pseudomonas sp. 42A2. Biotechnol. Lett. 21: 1031-1035.
3. Bergmeyer H.H., Gawehn K. and Grassl M. 1974. In: Bergmeyer H.H. (ed), Methods of Enzymatic Analysis. Vol. I.: Academic Press, New York, pp. 496-497.
4. Bisakowski B., Kermasha S. and Klopfenstein M.L. 1995. Partial purified lipoxygenase from Fusarium oxysporum: Characterization and kinetic studies. Process Biochem. 30: 261-268.
5. Bisakowski B., Atwal A.S. and Kermasha S. 2000. Characterization of lipoxygenase activity from a partially purified enzymic extract from Morchella esculenta. Process Biochem. 36: 1-7.
6. Brash A.R. 1999. Lipoxygenases. Occurence, functions, catalysis, and acquisition of substrate. J. Biol. Chem. 274: 23679-23682.
7. Brodowsky I.D. and Oliw E.H. 1993. Biosynthesis of 8R-hydroperoxylinoleic acid by fungus Laetisaria arvalis. Biochim. Biophys. Acta 1168: 68-72.
8. Canela E.I. 1984. A free derivative program for non-linear regression analysis of enzyme kinetics to be used on small computers. Int. J. Biomed. Comp. 15: 121-130.
9. De Andrés C., Mercadé E., Guinea J. and Manresa A. 1994. 7,10-Dihydroxy-8(E)-octadecenoic acid produced by Pseudomonas 42A2: evaluation of different cultural parameters of fermentation. World J. Microbiol. Biotechnol. 10: 106-108.
10. Feussner I. and Wasternack C. 1998. Lipoxygenase catalyzed oxygenation of lipids. Fett (Lipid) 100: 146-152.
11. Gardner H.W. and Hou C.T. 1999. All (S) stereoconfiguration of 7,10-dihydroxy-8(E)-octadecenoic acid from bioconversion of oleic acid by Pseudomonas aeruginosa. J. Am. Oil Chem. Soc. 76: 1151-1156.
12. Gonnella N.C., Nakanishi K., Martin V.S. and Sharpless K.B. 1982. General method for determining absolute configurations of acyclic allylic alcohols. J. Am. Chem. Soc. 104: 3775-3776.
13. Guerrero A., Casals I., Busquets M., Leon Y. and Manresa A. 1997. Oxidation of oleic acid to (E)-10-hydroperoxy-8-octadecenoic and (E)-10-hydroxy-8-octadecenoic acids by Pseudomonas sp 42A2. Biochim. Biophys, Acta 1347: 75-81.
14. Harada N. and Nakanishi K. 1972. The exciton chirality method and its application to configurational and conformational studies of natural products. Acc. Chem. Res. 5: 257-263.
15. Hartree E.P. 1972. Determination of protein: A modification of Lowry method that gives a linear photometric response. Anal. Biochem. 48: 422-427.
16. Herman R.P. and Hamberg M. 1987. Properties of the soluble arachidonic acid 15-LOX and 15-hydroperoxide isomerase from oomycete Saprolegnia parasitica. Prostaglandins 34: 129-139.
17. Hou C.T., Bagby M.O., Plattner R.D. and Koritala S. 1991. A novel compound, 7,10-dihydroxy-8(E)-octadecenoic acid from oleic acid by bioconversion. J. Am. Oil Chem. Soc. 68: 99-101.
18. Humpf H.U., Berova N. and Nakanishi K. 1995. Allylic and homoallylic exciton coupled CD: A sensitive method for determining the absolute stereochemistry of natural products. J. Org. Chem. 60: 3539-3542.
19. Husson F., Couturier A., Kermasha S. and Belin J. 1998. Induction and localization of a lipoxygenase from Fusarium proliferatum. J. Mol. Catal. B 5: 159-163.
20. Iny D., Pinsky A., Cojocoru M. and Grossman S. 1993a. Lipoxygenase of Thermoactinomyces vulgaris, purification and characterization of reaction products. J. Biochem. 25: 1313-1323.
21. Iny D., Grossman S. and Pinsky A. 1993b. Lipoxygenase of thermophilic bacteria Thermoactinomyces vulgaris - properties and study on the active site. Int. J. Biochem. 9: 1325-1330.
22. Knothe G., Bagby M.O., Weisleder D. and Peterson R.E. 1994. Allylic mono- and di-hydroxylation of isolated double bonds with selenium dioxide-tert-butylhydroperoxide. NMR characterization of long chain enols, allylic and saturated 1,4 diols and enones. J. Chem. Soc. Perkin Trans. 2: 1661-1669.
23. Koshino H., Togiya S., Yoshihara T., Sakamura S., Shimanuki T., Sato T. and Tajimi A. 1987. Four fungitoxic C-18 hydroxy unsaturated fatty acids from stromata of Epichloe typhina. Tetrahedron Lett. 28: 73-76.
24. Kuhn H. 2000. Structural basis for the positional specificity of lipoxygenases. Prostaglandins Other Lipid Mediators 62: 255-270.
25. Laemmli U.K. 1970. Cleavage of structural proteins during the assembly of head of bacteriophage T4. Nature 277: 680-685.
26. Matsuda Y., Beppu T. and Arima K. 1978. Crystallization and positional specificity of hydroperoxidation of Fusarium lipoxygenase. Biochim. Biophys. Acta 530: 39-540.
27. Mazur P., Meyers H.V., Nakamishi K., El-Zayat A.A.E. and Champe S.P. 1990. Structural elucidation of sporogenic fatty acid metabolites from Aspergillus nidulans. Tetrahedron Lett. 31: 3837-3840.
28. Medina I., Saeed S. and Howell N. 1999. Enzymatic oxidative activity in Sardine (Sardina pichardus) and herring (Cuplea harengus) during chilling and correlation with quality. Eur. Food Res. Technol. 210: 34-38.
29. Neu H.C. and Heppel L.A. 1964. On the surface localization of enzymes in Escherichia coli. Biochem. Biophys. Res. Commun. 17: 215-219.
30. Nuñez A., Savary B.J., Foglia A. and Piazza G. 2002. Purification of lipoxygenase from Chlorella: Production of 9- and 13-hydroperoxide derivatives of linoleic acid. Lipids 37: 1027-1032.
31. Oguri H., Hishiyama S., Sato O., Oishi T. and Hirama M. 1997. Synthetic study of ciguatoxin. Absolute configuration of the C2 hydroxy group. Tetrahedron 53: 3057-3072.
32. Okuyama H., Ueno A., Enari D., Morita N. and Kusano T. 1998. Purification and characterization of 9-hexadecenoic acid cis-trans isomerase from Pseudomonas Sp. strain E-3. Arch. Microbiol. 169: 29-35.
33. Pérez-Gilabert M., Veldink G. and Vliegenthart J.F.G. 1998. Oxidation of dilinoleoyl phosphatidylcholine by lipoxygenases from soybean. Arch. Biochem. Biophys. 354: 18-23.
34. Pérez-Gilabert M., Lopez-Nicolas J.M. and Carmona F.G. 2001. Purification of a novel lipoxygenase fron eggplant (Solanum melongena) fruit chloroplasts. Physiol. Plant. 111: 276-282.
35. Salas J., Williams M., Harwood J. and Sanchez J. 1999. Lipoxygenase activity in olive (Olea europea) fruit. J. Am. Oil Chem. Soc. 76: 1163-1168.
36. Satoh T., Matsuda Y., Takashio M., Satoh K., Beppu T. and Arima K. 1976. Isolation of lipoxygenase-like enzyme from Fusarium oxysporum. Appl. Biol. Chem. 40: 953-961.
37. Shechter G. and Grossman S. 1983. Lipoxygenase from baker's yeast: Purification and properties. Int. J. Biochem 15: 1295-1304.
38. Shimahara K. and Hashizume Y. 1973. Properties of lipoxygenase-like enzyme produced by Pseudomonas strain A4. J. Ferment. Technol. 51: 183-189.
39. Shimahara K. and Kajakozasshi K. 1964. Peroxidation of soy oil with lipoxygenase-like bacterium (gram-negative Bacillus) separated from garbage. Kogyo Kajakozasshi 67: 1164-1168.
40. Silverstein E. and Byer P.D. 1964. Equilibrium reaction rates and mechanisms of bovine heart and rabbit muscle lactate dehydrogenases. J. Biol. Chem. 239: 3901-3907.
41. Singer P., Ostreicher G. and Hogue P. 1973. Regulation of succinate dehydrogenase in higher plants. Plant Physiol. 52: 616-621.
42. Su C. and Oliw H. 1998. Manganese lipoxygenase. Purification and characterization. J. Biol. Chem. 273: 13072-13079. Lipoxygenase with a catalytic mononuclear redox center. J. Biol. Chem. 275, 18830-18835.
43. Sudharshan E., Srivasulu S. and Appu Rao A. 2000. pH-Induced domain interaction and conformational transition of lipoxygenase-1. Biochim. Biophys. Acta 1480: 13-22.
44. Surrey P.K. 1964. Spectrophotometric method for determination of lipoxidase activity. Plant Physiol. 39: 65-70.
45. Viegenthart J.F.G. and Veldink G.A. 1982. Lipoxygenases. In: Pryer W.A. (ed.), Free Radicals in Biology. Vol. 5. Academic Press, New York, pp. 29-64.
46. Yamamoto S. 1992. Mammalian lipoxygenase: Molecular structures and functions. Biochim. Biophys. Acta 1128: 117-131.
47. Zimmerman D.C. and Vick B.A. 1974. Lipoxygenase in Chlorella pyrenoidosa. Lipids 8: 264-266.