10(S)-hydroxy-8(E)-octadecenoic acid, an intermediate in the conversion of oleic acid to 7,10-dihydroxy-8(E)-octadecenoic acid

JAOCS, Journal of the American Oil Chemists' Society

Volumn 77, Issue 1, 2000, Pages 95-99

  Kim, Hakryul ^a   Gardner, Harold W ^b   Hou, Ching T ^a,b  

^a Oil Chemical Research   (United States)

^b NATIONAL CENTER FOR AGRICULTURAL UTILIZATION RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCONVERSION; CARBON; ESTERIFICATION; GAS CHROMATOGRAPHY; ISOMERS;

DIHYDROXYOCTADECANOIC ACID; HYDROXYOCTADECANOIC ACID;

OLEIC ACID;

PSEUDOMONAS; PSEUDOMONAS AERUGINOSA;

EID: 0033882337     PISSN: 0003021X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11746-000-0015-7     Document Type: Article

References (21)

1. Bagby, M.O., and K.D. Carlson, Chemical and Biological Conversion of Soybean Oil for Induslrial Products, in Fats for the Future, edited by R.C. Cambie, Ellis Horwood Limited Press, Chichester, 1989, pp. 301-317.
2. Wallen, L.L., R.G. Benedict, and R.W. Jackson, The Microbiological Production of 10-Hydroxystearic Acid from Oleic Acid, Arch. Biochem. Biophys. 99:249-253 (1962).
3. Hou, C.T., Microbial Oxidation of Unsaturated Fatty Acids, in Advances in Applied Microbiology, edited by A.I. Laskin, Academic Press, Ortando, 1995, Vol. 41, pp. 1-23.
4. Hou, C.T., M.O. Bagby, R.D. Plattner, and S. Koritala, A Novel Compound, 7,10-Dihydroxy-8(E)-octadecenoic Acid from Oleic Acid by Bioconversion, J. Am. Oil Chem. Soc. 68:99-101 (1991).
5. Hou, C.T., and M.O. Bagby, Production of a New Compound, 7,10-Dihydroxy-8(E)-octadecenoic Acid from Oleic Acid by Pseudomonas sp. PR3, J. Ind. Microbiol. 7:123-130 (1991).
6. Hou, C.T., L.K. Nkamura, D. Weisleder, R.E. Peterson, and M.O. Bagby, Identificalion of NRRL Strain B-18602 (PR3) as Pseudomonas aeruginosa and Effect of Phenazine-1-carboxylic Acid Formation on 7,10 Dihydroxy-8(E)-octadecenoic Acid Accumulation, World J. Microbiol. Biotechnol. 9:570-573 (1993).
7. Kuo, T.M., L.K. Manthey, and C.T. Hou, Fatty Acid Bioconversion by Pseudomonas aeruginosa PR3, J. Am. Oil. Chem. Soc. 75:875-879 (1998).
8. Mercade, E., M. Robert, M.J. Espuny, M.P. Bosch, M.A. Manreesa, J.L. Parra, and J. Guinea, New Surfactant Isolated from Pseudomonas sp. 42A2, Ibid. 65:1915-1916 (1988).
9. De Andres, C., E. Mercade, J. Guinea, and A. Manresa, 7, 10-Dihydroxy-8E-octadecenoic Acid Produced by Pseudomonas sp. 42A2: Evaluation of Different Cultural Parameters of the Fermentation, World J. Microbiol. Biotechnol. 10: 106-109 (1994).
10. Hou, C.T., and M.O. Bagby, 10-Hydroxy-8(Z)-octadecenoic Acid, an Intermediate in the Bioconversion of Oleic Acid to 7,10-Dihydroxy-8(E)-octadecenoic Acid, J. Ind. Microbiol. 9:103-107 (1992).
11. Guerrero, A., I. Casals, M. Busquets, Y. Leon, and A. Manresa, 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 (1997).
12. Hamberg, M., Steric Analysis of Hydroperoxides Formed by Lipoxygenase Oxygenation of Linoleic Acid, Anal. Biochem. 43:515-526 (1971).
13. Hamberg, M., R.P. Herman, and U. Jacobsson, Stereochemistry of Two Epoxy Alcohols from Saprolegnia parasitica, Biochim. Biophys. Acta 879:410-418 (1986).
14. Kleiman, R., and G.F. Spencer, Gas Chromatography-Mass Spectrometry of Methyl Esters of Unsaturated Oxygenated Fatty Acids, J. Am. Oil. Chem. Soc. 50:31-38 (1973).
15. Official and Tentative Methods of the AOCS, 3rd edn., edited by R.O. Walker, American Oil Chemists' Society, Champaign, 1981, Method Cd 14-61.
16. 13C Nuclear Magnetic Resonance Spectroscopy of Saturated, Unsaturated, and Oxygenated Fatty Acid Methyl Esters, Lipids 11:228-234 (1976).
17. Fahlstadius, P., and M. Hamberg, A Gas-Liquid Chromatographic Method for Steric Analysis of Epoxy Acids, Chem. Phys. Lipids 51:15-22 (1989).
18. Gardner, H.W., and C.T. Hou, 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 (1999).
19. Hou, C.T., Is Strain DS5 Hydratase a C-10 Positional Specific Enzyme? Identification of Bioconversion Products from α-and γ-Linolenic Acids by Flavobacterium sp. DS5, J. Ind. Microbiol 14:31-34 (1995).
20. Hou, C.T., Production of Hydroxy Fatty Acids from Unsaturated Fatty Acids by Flavobacterium sp. DS5 Hydratase, a C-10 Positional-and cis Unsaturation-Specific Enzyme, J. Am. Oil Chem. Soc. 72:1265-1270 (1995).
21. Oliw, E.H., I.D. Brodowsky, L. Hornstein, and M. Hamberg, Bis-allylic Hydroxylation of Polyunsaturated Fatty Acid by Hepatic Monoxygenases and Its Relation to the Enzymatic and Nonenzymatic Formation of Conjugated Hydroxy Fatty Acids, Arch. Biochem. Biophys. 300:434-439 (1993).