Production of hydroxy fatty acids by microbial fatty acid-hydroxylation enzymes

Biotechnology Advances

Volumn 31, Issue 8, 2013, Pages 1473-1485

  Kim, Kyoung Rok ^a   Oh, Deok Kun ^a  

^a Konkuk University   (South Korea)

Author keywords

12 Hydroxylase; Biotransformation; Diol synthase; Hydratase; Hydroxy fatty acid; Lipoxygenase; P450

Indexed keywords

12-HYDROXYLASE; BIOTRANSFORMATION; HYDRATASE; HYDROXY FATTY ACIDS; LIPOXYGENASES; P450; SYNTHASES;

BIOCHEMISTRY; ENZYMES; HYDROXYLATION; LUBRICANTS;

FATTY ACIDS;

BIOTRANSFORMATION; ENZYME; FATTY ACID; FOOD; GENETIC ENGINEERING; MICROBIAL ACTIVITY; PROTEIN;

CYTOCHROME P450; FATTY ACID; HYDROLYASE; HYDROXY FATTY ACID; LIPOXYGENASE; MIXED FUNCTION OXIDASE;

12-HYDROXYLASE; BIOTECHNOLOGY; BIOTRANSFORMATION; DIOL SYNTHASE; METABOLIC ENGINEERING; REVIEW;

12-HYDROXYLASE; BIOTRANSFORMATION; DIOL SYNTHASE; HYDRATASE; HYDROXY FATTY ACID; LIPOXYGENASE; P450;

BIOTECHNOLOGY; FATTY ACIDS; LIPOXYGENASES; METABOLIC ENGINEERING; MIXED FUNCTION OXYGENASES;

EID: 84888012588     PISSN: 07349750     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biotechadv.2013.07.004     Document Type: Review

References (183)

1. Akakabe Y., Matsui K., Kajiwara T. Enantioselective formation of (R)-9-HPODE and (R)-9-HPOTrE in marine green alga Ulva conglobata. Bioorg Med Chem 2002, 10:3171-3173.
2. Andreou A., Brodhun F., Feussner I. Biosynthesis of oxylipins in non-mammals. Prog Lipid Res 2009, 48:148-170.
3. Axarli I., Prigipaki A., Labrou N.E. Engineering the substrate specificity of cytochrome P450 CYP102A2 by directed evolution: production of an efficient enzyme for bioconversion of fine chemicals. Biomol Eng 2005, 22:81-88.
4. Back K.-Y., Sohn H.-R., Hou C.T., Kim H.-R. Production of a novel 9,12-dihydroxy-10(E)-eicosenoic acid from eicosenoic acid by Pseudomonas aeruginosa PR3. J Agric Food Chem 2011, 59:9652-9657.
5. Bae J.H., Suh M.J., Kim B.S., Hou C.T., Lee I.J., Kim I.H., et al. Optimal production of 7,10-dihydroxy-8(E)-hexadecenoic acid from palmitoleic acid by Pseudomonas aeruginosa PR3. N Biotechnol 2010, 27:352-357.
6. Bafor M., Smith M.A., Jonsson L., Stobart K., Stymne S. Ricinoleic acid biosynthesis and triacylglycerol assembly in microsomal preparations from developing castor-bean (Ricinus communis) endosperm. Biochem J 1991, 280:507-514.
7. Bagby M.O., Carlson K.D. Chemical and biological conversion of soybean oil for industrial products. Fats for the future 1989, 301-317. Ellis Horwood Limited Press, Chichester. R.C. Cambie (Ed.).
8. Bajpai V.K., Kim H.R., Hou C.T., Kang S.C. Bioconverted products of essential fatty acids as potential antimicrobial agents. N Biotechnol 2009, 26:122-130.
9. Bevers L., Pinkse M., Verhaert P., Hagen W. Oleate hydratase catalyzes the hydration of a nonactivated carbon-carbon bond. J Bacteriol 2009, 191:5010-5012.
10. Biermann U., Bornscheuer U., Meier M.A.R., Metzger J.O., Schäfer H.J. Oils and fats as renewable raw materials in chemistry. Angew Chem Int Ed Engl 2011, 50:3854-3871.
11. Billault I., Mantle P.G., Robins R.J. Deuterium NMR used to indicate a common mechanism for the biosynthesis of ricinoleic acid by Ricinus communis and Claviceps purpurea. J Am Chem Soc 2004, 126:3250-3256.
12. Boddupalli S.S., Pramanik B.C., Slaughter C.A., Estabrook R.W., Peterson J.A. Fatty acid monooxygenation by P450BM-3: product identification and proposed mechanisms for the sequential hydroxylation reactions. Arch Biochem Biophys 1992, 292:20-28.
13. Bowers W.S., Hoch H.C., Evans P.H., Katayama M. Thallphytic alleopathy: isolation and identification of laetisaric acid. Science 1986, 232:105-106.
14. Brash A.R. Lipoxygenases: occurrence, functions, catalysis, and acquisition of substrate. J Biol Chem 1999, 274:23679-23682.
15. Broadwater J.A., Whittle E., Shanklin J. Desaturation and hydroxylation: residues 148 and 324 of Arabidopsis FAD2, in addition to substrate chain length, exert a major influence in partitioning of catalytic specificity. J Biol Chem 2002, 277:15613-15620.
16. Brodhun F., Göbel C., Hornung E., Feussner I. Identification of PpoA from Aspergillus nidulans as a fusion protein of a fatty acid heme dioxygenase/peroxidase and a cytochrome P450. J Biol Chem 2009, 284:11792-11805.
17. Brodhun F., Schneider S., Göbel C., Hornung E., Feussner I. PpoC from Aspergillus nidulans is a fusion protein with only one active haem. Biochem J 2010, 425:553-565.
18. Brodowsky I.D., Hamberg M., Oliw E.H. A linoleic acid (8R)-dioxygenase and hydroperoxide isomerase of the fungus Gaeumannomyces graminis. Biosynthesis of (8R)-hydroxylinoleic acid and (7S,8S)-dihydroxylinoleic acid from (8R)-hydroperoxylinoleic acid. J Biol Chem 1992, 267:14738-14745.
19. Broun P., Somerville C. Accumulation of ricinoleic, lesquerolic, and densipolic acids in seeds of transgenic Arabidopsis plants that express a fatty acyl hydroxylase cdna from castor bean. Plant Physiol 1997, 113:933-942.
20. Broun P., Boddupalli S., Somerville C. A bifunctional oleate 12-hydroxylase: desaturase from Lesquerella fendleri. Plant J 1998, 13:201-210.
21. Broun P., Shanklin J., Whittle E., Somerville C. Catalytic plasticity of fatty acid modification enzymes underlying chemical diversity of plant lipids. Science 1998, 282:1315-1317.
22. Buczynski M.W., Dumlao D.S., Dennis E.A. Thematic review series: proteomics. an integrated omics analysis of eicosanoid biology. J Lipid Res 2009, 50:1015-1038.
23. Budde M., Maurer S.C., Schmid R.D., Urlacher V.B. Cloning, expression and characterisation of CYP102A2, a self-sufficient P450 monooxygenase from Bacillus subtilis. Appl Microbiol Biotechnol 2004, 66:180-186.
24. Burdock G.A., Carabin I.G., Griffiths J.C. Toxicology and pharmacology of sodium ricinoleate. Food Chem Toxicol 2006, 44:1689-1698.
25. Capdevila J.H., Wei S., Helvig C., Falck J.R., Belosludtsev Y., Truan G., et al. The highly stereoselective oxidation of polyunsaturated fatty acids by cytochrome 450BM-3. J Biol Chem 1996, 271:22663-22671.
26. Chang I.A., Bae J.H., Suh M.J., Kim I.H., Hou C.T., Kim H.R. Environmental optimization for bioconversion of triolein into 7,10-dihydroxy-8(E)-octadecenoic acid by Pseudomonas aeruginosa PR3. Appl Microbiol Biotechnol 2008, 78:581-586.
27. Chen C.K.J., Shokhireva T.K., Berry R.E., Zhang H., Walker F.A. The effect of mutation of F87 on the properties of CYP102A1-CYP4C7 chimeras: altered regiospecificity and substrate selectivity. J Biol Inorg Chem 2008, 13:813-824.
28. Chiang N., Serhan C.N., Dahlén S.-E., Drazen J.M., Hay D.W.P., Rovati G.E., et al. The lipoxin receptor ALX: potent ligand-specific and stereoselective actions in vivo. Pharmacol Rev 2006, 58:463-487.
29. Chiang N., Fredman G., Backhed F., Oh S.F., Vickery T., Schmidt B.A., et al. Infection regulates pro-resolving mediators that lower antibiotic requirements. Nature 2012, 484:524-528.
30. 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.
31. Cristea M., Osbourn A., Oliw E. Linoleate diol synthase of the rice blast fungus Magnaporthe grisea. Lipids 2003, 38:1275-1280.
32. Culleré J., Durany O., Busquets M., Manresa A. Biotransformation of oleic acid into (E)-10-hydroxy-8-octadecenoic acid and (E)-7,10-dihydroxy-8-octadecenoic acid by Pseudomonas sp. 42A2 in an immobilized system. Biotechnol Lett 2001, 23:215-219.
33. Dauk M., Lam P., Kunst L., Smith M.A. A FAD2 homologue from Lesquerella lindheimeri has predominantly fatty acid hydroxylase activity. Plant Sci 2007, 173:43-49.
34. Dietrich M., Do T.A., Schmid R.D., Pleiss J., Urlacher V.B. Altering the regioselectivity of the subterminal fatty acid hydroxylase P450 BM-3 towards γ- and δ-positions. J Biotechnol 2009, 139:115-117.
35. Drouet P., Thomas D., Legoy M.D. Production of 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid using soybean lipoxygenase 1 in a biphasic octane-water system. Tetrahedron Lett 1994, 35:3923-3926.
36. El Kebir D., Gjorstrup P., Filep J.G. Resolvin E1 promotes phagocytosis-induced neutrophil apoptosis and accelerates resolution of pulmonary inflammation. Proc Natl Acad Sci U S A 2012, 109:14983-14988.
37. Endrizzi A., Pagot Y., Clainche A.L., Nicaud J.-M., Belin J.-M. Production of lactones and peroxisomal beta-oxidation in yeasts. Crit Rev Biotechnol 1996, 16:301-329.
38. Eschenfeldt W.H., Zhang Y., Samaha H., Stols L., Eirich L.D., Wilson C.R., et al. Transformation of fatty acids catalyzed by cytochrome P450 monooxygenase enzymes of Candida tropicalis. Appl Environ Microbiol 2003, 69:5992-5999.
39. 9-cis-1,18-octadecenedioic acid by mutants of Candida tropicalis. Appl Microbiol Biotechnol 1996, 45:342-348.
40. Fer M., Corcos L., Dréano Y., Plée-Gautier E., Salaün J.P., Berthou F., et al. Cytochromes P450 from family 4 are the main ω-hydroxylating enzymes in humans: CYP4F3B is the prominent player in PUFA metabolism. J Lipid Res 2008, 49:2379-2389.
41. Fox S., Akpinar A., Prabhune A., Friend J., Ratledge C. The biosynthesis of oxylipins of linoleic and arachidonic acids by the sewage fungus Leptomitus lacteus, including the identification of 8R-hydroxy-9Z,12Z-octadecadienoic acid. Lipids 2000, 35:23-30.
42. Funk C.D. Prostaglandins and leukotrienes: advances in eicosanoid biology. Science 2001, 294:1871-1875.
43. Gao J.M., Wang C.Y., Zhang A.L., Liu J.K. A new trihydroxy fatty acid from the ascomycete, Chinese truffle Tuber indicum. Lipids 2001, 36:1365-1370.
44. Gardner H., Hou C. All (S) stereoconfiguration of 7,10-dihydroxy-8(E)-octadecenoic acid from bioconversion of oleic acid by Pseudomonas aeruginosa. J Am Oil Chem Soc 1999, 76:1151-1156.
45. Gardner H.W., Hou C.T., Weisleder D., Brown W. Biotransformation of linoleic acid by Clavibacter sp. ALA2: heterocyclic and heterobicyclic fatty acids. Lipids 2000, 35:1055-1060.
46. Garscha U., Oliw E.H. Steric analysis of 8-hydroxy- and 10-hydroxyoctadecadienoic acids and dihydroxyoctadecadienoic acids formed from 8R-hydroperoxyoctadecadienoic acid by hydroperoxide isomerases. Anal Biochem 2007, 367:238-246.
47. Garscha U., Oliw E.H. Leucine/valine residues direct oxygenation of linoleic acid by (10R)- and (8R)-dioxygenases: expression and site-directed mutagenesis of (10R)-dioxygenase with epoxyalcohol synthase activity. J Biol Chem 2009, 284:13755-13765.
48. Gerwick W.H., Moghaddam M., Hamberg M. Oxylipin metabolism in the red alga Gracilariopsis lemaneiformis: mechanism of formation of vicinal dihydroxy fatty acids. Arch Biochem Biophys 1991, 290:436-444.
49. Gow G. Lubricating grease. Chemistry and technology of lubricants 2010, 411-432. Springer, Netherlands. R.M. Mortier, M.F. Fox, S.T. Orszulik (Eds.).
50. Gustafsson M.C.U., Roitel O., Marshall K.R., Noble M.A., Chapman S.K., Pessegueiro A., et al. Expression, purification, and characterization of Bacillus subtilis cytochromes P450 CYP102A2 and CYP102A3: flavocytochrome homologues of P450 BM3 from Bacillus megaterium. Biochemistry 2004, 43:5474-5487.
51. Hamberg M. Isolation and structures of lipoxygenase products from Saprolegnia parasitica. Biochim Biophys Acta 1986, 876:688-692.
52. Hamberg M. An epoxy alcohol synthase pathway in higher plants: biosynthesis of antifungal trihydroxy oxylipins in leaves of potato. Lipids 1999, 34:1131-1142.
53. Hamberg M., Gerwick W.H. Biosynthesis of vicinal dihydroxy fatty acids in the red alga Gracilariopsis lemaneiformis: identification of a sodium-dependent 12-lipoxygenase and a hydroperoxide isomerase. Arch Biochem Biophys 1993, 305:115-122.
54. Hamberg M., 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 1996, 110:807-815.
55. Hamberg M., Olsson U. Efficient and specific conversion of 9-lipoxygenase hydroperoxides in the Beetroot. Formation of pinellic acid. Lipids 2011, 46:873-878.
56. Hamberg M., Sanz A., Castresana C. α-Oxidation of fatty acids in higher plants. Identification of a pathogen-inducible oxygenase (piox) as an α-dioxygenase and biosynthesis of 2-hydroperoxylinolenic acid. J Biol Chem 1999, 274:24503-24513.
57. Hamberg M., Su C., Oliw E. Manganese lipoxygenase: discovery of a bis-allylic hydroperoxide as product and intermediate in a lipoxygenase. J Biol Chem 1998, 273:13080-13088.
58. Hamberg M., Sanz A., Rodriguez M.J., Calvo A.P., Castresana C. Activation of the fatty acid α-dioxygenase pathway during bacterial infection of tobacco leaves: formation of oxylipinds protecting against cell death. J Biol Chem 2003, 278:51796-51805.
59. Heo S.H., Hou C.T., Kim B.S. Production of oxygenated fatty acids from vegetable oils by Flavobacterium sp. strain DS5. N Biotechnol 2009, 26:105-108.
60. Hoffmann I., Jernerén F., Garscha U., Oliw E.H. Expression of 5,8-LDS of Aspergillus fumigatus and its dioxygenase domain. A comparison with 7,8-LDS, 10-dioxygenase, and cyclooxygenase. Arch Biochem Biophys 2011, 506:216-222.
61. Holic R., Yazawa H., Kumagai H., Uemura H. Engineered high content of ricinoleic acid in fission yeast Schizosaccharomyces pombe. Appl Microbiol Biotechnol 2012, 95:179-187.
62. 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, 96:4192-4197.
63. Hosokawa M., Hou C.T., Weisleder D. Production of novel tetrahydroxyfuranyl fatty acids from a-linolenic acid by Clavibacter sp. strain ALA2. Appl Environ Microbiol 2003, 69:3868-3873.
64. Hou C.T. Conversion of linoleic acid to 10-hydroxy-12(Z)-octadecenoic acid by Flavobacterium sp. (NRRL B-14859). J Am Oil Chem Soc 1994, 71:975-978.
65. Hou C.T. Production of hydroxy fatty acids from unsaturated fatty acids by Flavobacterium sp. DS5 hydratase, a C-10 positional specific and cis-unsaturation specific enzyme. J Am Oil Chem Soc 1995, 72:1265-1270.
66. Hou C.T. A novel compound, 12,13,17-trihydroxy-9(Z)-octadecenoic acid, from linoleic acid by a new microbial isolate, Clavibacter sp. ALA2. J Am Oil Chem Soc 1996, 73:1359-1362.
67. Hou CT. 12,13,17-Trihydroxy-9(Z)-octadecenoic acid and derivatives and microbial isolate for production of the acid. U.S. Patent 5,852,196, 1998.
68. Hou C.T. Biotransformation of unsaturated fatty acids to industrial products. Adv Appl Microbiol 2000, 47:201-220.
69. Hou C.T. 12,13,16-Trihydroxy-9(Z)-octadecenoic acid, a possible intermediate in the biosynthesis of linoleic acid to tetrahydrofuranyl fatty acids by Clavibacter sp. ALA2. J Am Oil Chem Soc 2001, 78:1167-1169.
70. Hou C.T. Monooxygenase system of Bacillus megaterium ALA2: studies on linoleic acid epoxidation products. J Am Oil Chem Soc 2006, 83:677-681.
71. Hou C.T. Biotechnology for fats and oils: new oxygenated fatty acids. N Biotechnol 2009, 26:2-10.
72. Hou C.T., Bagby M.O. Production of a new compound, 7,10-dihydroxy-8(E)-octadecenoic acid from oleic acid by Pseudomonas sp. PR3. J Ind Microbiol 1991, 7:123-130.
73. Hou C.T., Hosokawa M. Production of value-added industrial products from vegetable oils: oxygenated fatty acids. Handbook of industrial biocatalysis 2005, 1-25. CRC Press. C.T. Hou (Ed.).
74. Hou C.T., Bagby M.O., Plattner R.D., Koritala S. A novel compound, 7,10-dihydroxy-8(E)-octadecenoic acid from oleic acid by bioconversion. J Am Oil Chem Soc 1991, 68:99-101.
75. Hou C.T., Gardner H., Brown W. Production of polyhydroxy fatty acids from linoleic acid by Clavibacter sp. ALA2. J Am Oil Chem Soc 1998, 75:1483-1487.
76. Huang C., Chen X.F., Xiong L., Chen X.D., Ma L.L., Chen Y. Single cell oil production from low-cost substrates: the possibility and potential of its industrialization. Biotechnol Adv 2013, 31:129-139.
77. Hudson J.A., MacKenzie C.A.M., Joblin K.N. Conversion of oleic acid to 10-hydroxystearic acid by two species of ruminal bacteria. Appl Microbiol Biotechnol 1995, 44:1-6.
78. Hudson J.A., MacKenzie C.A.M., Joblin K.N. Hydration of oleic acid by a Selenomonas strain from the ovine rumen. Lett Appl Microbiol 1996, 23:133-135.
79. Hudson J.A., Morvan B., Joblin K.N. Hydration of linoleic acid by bacteria isolated from ruminants. FEMS Microbiol Lett 1998, 169:277-282.
80. Iacazio G., Langrand G., Baratti J., Buono G., Triantaphylides C. Preparative, enzymic synthesis of linoleic acid (13S)-hydroperoxide using soybean lipoxygenase-1. J Org Chem 1990, 55:1690-1691.
81. Itoh T., Fairall L., Amin K., Inaba Y., Szanto A., Balint B.L., et al. Structural basis for the activation of PPARγ by oxidized fatty acids. Nat Struct Mol Biol 2008, 15:924-931.
82. Ivanov I., Heydeck D., Hofheinz K., Roffeis J., Oonnell V.B., Kuhn H., et al. Molecular enzymology of lipoxygenases. Arch Biochem Biophys 2010, 503:161-174.
83. James A.T., Hadaway H.C., Webb J.P. The biosynthesis of ricinoleic acid. Biochem J 1965, 95:448-452.
84. Jeon E.-Y., Lee J.-H., Yang K.-M., Joo Y.-C., Oh D.-K., Park J.-B. Bioprocess engineering to produce 10-hydroxystearic acid from oleic acid by recombinant Escherichia coli expressing the oleate hydratase gene of Stenotrophomonas maltophilia. Process Biochem 2012, 47:941-947.
85. Jernerén F., Oliw E. The fatty acid 8,11-diol synthase of Aspergillus fumigatus is inhibited by imidazole derivatives and unrelated to PpoB. Lipids 2012, 47:707-717.
86. Jernerén F., Garscha U., Hoffmann I., Hamberg M., Oliw E.H. Reaction mechanism of 5,8-linoleate diol synthase, 10R-dioxygenase, and 8,11-hydroperoxide isomerase of Aspergillus clavatus. Biochim Biophys Acta 2010, 1801:503-507.
87. Jernerén F., Sesma A., Francheschetti M., Hamberg M., Oliw E.H. Gene deletion of 7,8-linoleate diol synthase of the rice blast fungus: studies on pathogenicity, stereochemistry, and oxygenation mechanisms. J Biol Chem 2010, 285:5308-5316.
88. Jernerén F., Eng F., Hamberg M., Oliw E. Linolenate 9R-dioxygenase and allene oxide synthase activities of Lasiodiplodia theobromae. Lipids 2012, 47:65-73.
89. Jetter R., Kunst L. Plant surface lipid biosynthetic pathways and their utility for metabolic engineering of waxes and hydrocarbon biofuels. Plant J 2008, 54:670-683.
90. Jira W., Spiteller G., Richter A. Increased levels of lipid oxidation products in low density lipoproteins of patients suffering from rheumatoid arthritis. Chem Phys Lipids 1997, 87:81-89.
91. Jisaka M., Kim R.B., Boeglin W.E., Brash A.R. Identification of amino acid determinants of the positional specificity of mouse 8S-lipoxygenase and human 15S-lipoxygenase-2. J Biol Chem 2000, 275:1287-1293.
92. Joo Y.C., Oh D.K. Lipoxygenases: potential starting biocatalysts for the synthesis of signaling compounds. Biotechnol Adv 2012, 30:1524-1532.
93. Joo Y.C., Jeong K.W., Yeom S.J., Kim Y.S., Kim Y., Oh D.K. Biochemical characterization and FAD-binding analysis of oleate hydratase from Macrococcus caseolyticus. Biochimie 2012, 94:907-915.
94. Joo Y.C., Seo E.S., Kim Y.S., Kim K.R., Park J.B., Oh D.K. Production of 10-hydroxystearic acid from oleic acid by whole cells of recombinant Escherichia coli containing oleate hydratase from Stenotrophomonas maltophilia. J Biotechnol 2012, 158:17-23.
95. Jung S.T., Lauchli R., Arnold F.H. Cytochrome P450: taming a wild type enzyme. Curr Opin Biotechnol 2011, 22:809-817.
96. Kandel S., Sauveplane V., Olry A., Diss L., Benveniste I., Pinot F. Cytochrome P450-dependent fatty acid hydroxylases in plants. Phytochem Rev 2006, 5:359-372.
97. Kim H., Gardner H.W., Hou C.T. 10(S)-Hydroxy-8(E)-octadecenoic acid, an intermediate in the conversion of oleic acid to 7,10-dihydroxy-8(E)-octadecenoic acid. J Am Oil Chem Soc 2000, 77:95-99.
98. Kim H., Gardner H.W., Hou C.T. Production of isomeric 9,10,13 (9,12,13)-trihydroxy-11E (10E)-octadecenoic acid from linoleic acid by Pseudomonas aeruginosa PR3. J Ind Microbiol Biotechnol 2000, 25:109-115.
99. Kim B.S., Kim S.Y., Park J., Park W., Hwang K.Y., Yoon Y.J., et al. Sequence-based screening for self-sufficient P450 monooxygenase from a metagenome library. J Appl Microbiol 2007, 102:1392-1400.
100. Kim B.S., Kim H.R., Hou C.T. Effect of surfactant on the production of oxygenated unsaturated fatty acids by Bacillus megaterium ALA2. N Biotechnol 2010, 27:33-37.
101. Kim B.-N., Yeom S.-J., Oh D.-K. Conversion of oleic acid to 10-hydroxystearic acid by whole cells of Stenotrophomonas nitritireducens. Biotechnol Lett 2011, 33:993-997.
102. Kim B.N., Joo Y.C., Kim Y.S., Kim K.R., Oh D.K. Production of 10-hydroxystearic acid from oleic acid and olive oil hydrolyzate by an oleate hydratase from Lysinibacillus fusiformis. Appl Microbiol Biotechnol 2012, 95:929-937.
103. Kishimoto Y., Radin N.S. Occurrence of 2-hydroxy fatty acids in animal tissues. J Lipid Res 1963, 4:139-143.
104. Kishimoto N., Yamamoto I., Toraishi K., Yoshioka S., Saito K., Masuda H., et al. Two distinct pathways for the formation of hydroxy FA from linoleic acid by lactic acid bacteria. Lipids 2003, 38:1269-1274.
105. Kitazume T., Yamazaki Y., Matsuyama S., Shoun H., Takaya N. Production of hydroxy-fatty acid derivatives from waste oil by Escherichia coli cells producing fungal cytochrome P450foxy. Appl Microbiol Biotechnol 2008, 79:981-988.
106. Knight B. Ricin: a potent homicidal poison. Br Med J 1979, 1:350-351.
107. Kock J.L.F., Strauss C.J., Pohl C.H., Nigam S. The distribution of 3-hydroxy oxylipins in fungi. Prostaglandins Other Lipid Mediat 2003, 71:85-96.
108. Koritala S., Bagby M.O. Microbial conversion of linoleic and linolenic acids to unsaturated hydroxy fatty acids. J Am Oil Chem Soc 1992, 69:575-578.
109. Koritala S., Hou C.T., Hesseltine C.W., Bagby M.O. Microbial conversion of oleic acid to 10-hydroxystearic acid. Appl Microbiol Biotechnol 1989, 32:299-304.
110. Kuo T.M., Lanser A.C. Factors influencing the production of a novel compound, 7,10-dihydroxy-8(E)-octadecenoic acid, by Pseudomonas aeruginosa PR3 (NRRL B-18602) in batch cultures. Curr Microbiol 2003, 47:186-191.
111. Kuo T.M., Levinson W.E. Biocatalytic production of 10-hydroxystearic acid, 10-ketostearic acid, and their primary fatty amides. J Am Oil Chem Soc 2006, 83:671-675.
112. Kuo T.M., Nakamura L.K. Diversity of oleic acid, ricinoleic acid and linoleic acid conversions among Peudomonas aeruginosa strains. Curr Microbiol 2004, 49:261-266.
113. Kuo T.M., Lanser A.C., Nakamura L.K., Hou C.T. Production of 10-ketostearic Acid and 10-hydroxystearic acid by strains of Sphingobacterium thalpophilum isolated from composted manure. Curr Microbiol 2000, 40:105-109.
114. Kuo T.M., Kim H., Hou C.T. Production of a novel compound, 7,10,12-trihydroxy-8(E)-octadecenoic acid from ricinoleic acid by Pseudomonas aeruginosa PR3. Curr Microbiol 2001, 43:198-203.
115. Lang I., Feussner I. Oxylipin formation in Nostoc punctiforme (PCC73102). Phytochem 2007, 68:1120-1127.
116. Lang I., Göbel C., Porzel A., Heilmann I., Feussner I. A lipoxygenase with linoleate diol synthase activity from Nostoc sp. PCC 7120. Biochem J 2008, 410:347-357.
117. Latrasse A., Paitier S., Lachot B., Bonnarme P., Féron G., Durand A., et al. Conversion of oleic acid to 10-hydroxystearic acid by Nocardia paraffinae. Biotechnol Lett 1997, 19:715-718.
118. Lee D.-S., Yamada A., Sugimoto H., Matsunaga I., Ogura H., Ichihara K., et al. Substrate recognition and molecular mechanism of fatty acid hydroxylation by cytochrome P450 from Bacillus subtilis. J Biol Chem 2003, 278:9761-9767.
119. Lequeu J., Fauconnier M.L., Chammaï A., Bronner R., Blée E. Formation of plant cuticle: evidence for the occurrence of the peroxygenase pathway. Plant J 2003, 36:155-164.
120. Lima Da Silva N., Maciel M.R.W., Batistella C.B., Filho R. Optimization of biodiesel production from castor oil. Appl Biochem Biotechnol 2006, 130:405-414.
121. Mandai T., Fujiwara S., Imaoka S. Construction and engineering of a thermostable self-sufficient cytochrome P450. Biochem Biophys Res Commun 2009, 384:61-65.
122. Mantle P.G., Nisbet L.J. Differentiation of Claviceps purpurea in axenic culture. J Gen Microbiol 1976, 93:321-334.
123. Matsunaga I., Yamada M., Kusunose E., Nishiuchi Y., Yano I., Ichihara K. Direct involvement of hydrogen peroxide in bacterial α-hydroxylation of fatty acid. FEBS Lett 1996, 386:252-254.
124. Matsunaga I., Yamada M., Kusunose E., Miki T., Ichihara K. Further characterization of hydrogen peroxide-dependent fatty acid α-hydroxylase from Sphingomonas paucimobilis. J Biochem 1998, 124:105-110.
125. Matsunaga I., Ueda A., Fujiwara N., Sumimoto T., Ichihara K. Characterization of the ybdT gene product of Bacillus subtilis: novel fatty acid β-hydroxylating cytochrome P450. Lipids 1999, 34:841-846.
126. Matsunaga I., Sumimoto T., Ueda A., Kusunose E., Ichihara K. Fatty acid-specific, regiospecific, and stereospecific hydroxylation by cytochrome P450 (CYP152B1) from Sphingomonas paucimobilis: substrate structure required for α-hydroxylation. Lipids 2000, 35:365-371.
127. Meesapyodsuk D., Qiu X. An oleate hydroxylase from the fungus Claviceps purpurea: cloning, functional analysis, and expression in Arabidopsis. Plant Physiol 2008, 147:1325-1333.
128. Meruvu S., Walther M., Ivanov I., Hammarström S., Fürstenberger G., Krieg P., et al. Sequence determinants for the reaction specificity of murine (12R)-lipoxygenase: targeted substrate modification and site-directed mutagenesis. J Biol Chem 2005, 280:36633-36641.
129. Metzger J.O., Bornscheuer U. Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification. Appl Microbiol Biotechnol 2006, 71:13-22.
130. Moreno J.J. New aspects of the role of hydroxyeicosatetraenoic acids in cell growth and cancer development. Biochem Pharmacol 2009, 77:1-10.
131. Morris L., Hall S., James A. The biosynthesis of ricinoleic acid by Claviceps purpurea. Biochem J 1966, 100:29C-30C.
132. Mortimer M., Jarving R., Brash A.R., Samel N., Jarving I. Identification and characterization of an arachidonate 11R-lipoxygenase. Arch Biochem Biophys 2006, 445:147-155.
133. Morvan B., Joblin K.N. Hydration of oleic acid by Enterococcus gallinarum, Pediococcus acidilactici and Lactobacillus sp. isolated from the rumen. Anaerobe 1999, 5:605-611.
134. Mosblech A., Feussner I., Heilmann I. Oxylipins: structurally diverse metabolites from fatty acid oxidation. Plant Physiol Biochem 2009, 47:511-517.
135. Mutlu H., Meier M.A.R. Castor oil as a renewable resource for the chemical industry. Eur J Lipid Sci Technol 2010, 112:10-30.
136. Nagai T., Shimizu Y., Shirahata T., Sunazuka T., Kiyohara H., Ōmura S., et al. Oral adjuvant activity for nasal influenza vaccines caused by combination of two trihydroxy fatty acid stereoisomers from the tuber of Pinellia ternata. Int Immunopharmacol 2010, 10:655-661.
137. Nakayama N., Takemae A., Shoun H. Cytochrome P450foxy, a catalytically self-sufficient fatty acid hydroxylase of the fungus Fusarium oxysporum. J Biochem 1996, 119:435-440.
138. Niehaus W.G., Kisic A., Torkelson A., Bednarczyk D.J., Schroepfer G.J. Stereospecific hydration of cis- and trans-9,10-epoxyoctadecanoic acids. J Biol Chem 1970, 245:3802-3809.
139. Ogawa J., Matsumura K., Kishino S., Omura Y., Shimizu S. Conjugated linoleic acid accumulation via 10-hydroxy-12-octadecaenoic acid during microaerobic transformation of linoleic acid by Lactobacillus acidophilus. Appl Environ Microbiol 2001, 67:1246-1252.
140. Ogunniyi D.S. Castor oil: a vital industrial raw material. Bioresour Technol 2006, 97:1086-1091.
141. Oliw E.H. Plant and fungal lipoxygenases. Prostaglandins Other Lipid Mediat 2002, 68-69:313-323.
142. Parolin C., Calonghi N., Presta E., Boga C., Caruana P., Naldi M., et al. Mechanism and stereoselectivity of HDAC I inhibition by (R)-9-hydroxystearic acid in colon cancer. Biochim Biophys Acta 2012, 1821:1334-1340.
143. Paul S., Hou C.T., Kang S.C. α-Glucosidase inhibitory activities of 10-hydroxy-8(E)-octadecenoic acid: an intermediate of bioconversion of oleic acid to 7,10-dihydroxy-8(E)-octadecenoic acid. N Biotechnol 2010, 27:419-423.
144. Pinot F., Beisson F. Cytochrome P450 metabolizing fatty acids in plants: characterization and physiological roles. FEBS J 2011, 278:195-205.
145. Renfrey S., Downton C., Featherstone J. The painful reality. Nat Rev Drug Discov 2003, 2:175-176.
146. Rosberg-Cody E., Liavonchanka A., Gobel C., Ross R., O'Sullivan O., Fitzgerald G., et al. Myosin-cross-reactive antigen (MCRA) protein from Bifidobacterium breve is a FAD-dependent fatty acid hydratase which has a function in stress protection. BMC Biochem 2011, 12:9.
147. Ruettinger R.T., Fulco A.J. Epoxidation of unsaturated fatty acids by a soluble cytochrome P-450-dependent system from Bacillus megaterium. J Biol Chem 1981, 256:5728-5734.
148. Schneider C., Pozzi A. Cyclooxygenases and lipoxygenases in cancer. Cancer Metastasis Rev 2011, 30:277-294.
149. Schwab J.M., Serhan C.N. Lipoxins and new lipid mediators in the resolution of inflammation. Curr Opin Pharmacol 2006, 6:414-420.
150. Schwaneberg U., Otey C., Cirino P.C., Farinas E., Arnold F.H. Cost-effective whole-cell assay for laboratory evolution of hydroxylases in Escherichia coli. J Biomol Screen 2001, 6:111-117.
151. Schwarz K., Walther M., Anton M., Gerth C., Feussner I., Kuhn H. Structural basis for lipoxygenase specificity: conversion of the human leukocyte 5-lipoxygenase to a 15-lipoxygenating enzyme species by site-directed mutagenesis. J Biol Chem 2001, 276:773-779.
152. Senger T., Wichard T., Kunze S., Göbel C., Lerchl J., Pohnert G., et al. A multifunctional lipoxygenase with fatty acid hydroperoxide cleaving activity from the moss Physcomitrella patens. J Biol Chem 2005, 280:7588-7596.
153. Seo M.H., Kim K.R., Oh D.K. Production of a novel compound, 10,12-dihydroxystearic acid from ricinoleic acid by an oleate hydratase from Lysinibacillus fusiformis. Appl Microbiol Biotechnol 2013, 1-9.
154. Serhan C.N. Lipoxins and aspirin-triggered 15-epi-lipoxin biosynthesis: an update and role in anti-inflammation and pro-resolution. Prostaglandins Other Lipid Mediat 2002, 68-69:433-455.
155. Serhan C.N., Chiang N., Van Dyke T.E. Resolving inflammation: dual anti-inflammatory and pro-resolution lipid mediators. Nat Rev Immunol 2008, 8:349-361.
156. Shimizu T., Rådmark O., Samuelsson B. Enzyme with dual lipoxygenase activities catalyzes leukotriene A4 synthesis from arachidonic acid. Proc Natl Acad Sci U S A 1984, 81:689-693.
157. Shureiqi I., Jiang W., Zuo X., Wu Y., Stimmel J.B., Leesnitzer L.M., et al. The 15-lipoxygenase-1 product 13-S-hydroxyoctadecadienoic acid down-regulates PPAR-δ to induce apoptosis in colorectal cancer cells. Proc Natl Acad Sci U S A 2003, 100:9968-9973.
158. Sloane D.L., Leung R., Barnett J., Craik C.S., Sigal E. Conversion of human 15-lipoxygenase to an efficient 12-lipoxygenase: the side-chain geometry of amino acids 417 and 418 determine positional specificity. Protein Eng 1995, 8:275-282.
159. Song J.W., Jeon E.Y., Song D.H., Jang H.Y., Bornscheuer U.T., Oh D.K., et al. Multistep enzymatic synthesis of long-chain α, ω-dicarboxylic and ω-hydroxycarboxylic acids from renewable fatty acids and plant oils. Angew Chem Int Ed 2013, 52:2534-2537.
160. Stables M.J., Gilroy D.W. Old and new generation lipid mediators in acute inflammation and resolution. Prog Lipid Res 2011, 50:35-51.
161. Su C., Sahlin M., Oliw E.H. A protein radical and ferryl intermediates are generated by linoleate diol synthase, a ferric hemeprotein with dioxygenase and hydroperoxide isomerase activities. J Biol Chem 1998, 273:20744-20751.
162. Suh M.J., Baek K.Y., Kim B.S., Hou C.T., Kim H.R. Production of 7,10-dihydroxy-8(E)-octadecenoic acid from olive oil by Pseudomonas aeruginosa PR3. Appl Microbiol Biotechnol 2011, 89:1721-1727.
163. Tian H., Lu Y., Shah S.P., Hong S. 14S,21R-dihydroxydocosahexaenoic acid remedies impaired healing and mesenchymal stem cell functions in diabetic wounds. J Biol Chem 2011, 286:4443-4453.
164. Torrego-Solana N., Martin-Arjol I., Bassas-Galia M., Diaz P., Manresa A. Hydroxy-fatty acid production in a Pseudomonas aeruginosa 42A2 PHA synthase mutant generated by directed mutagenesis. Appl Microbiol Biotechnol 2012, 93:2551-2561.
165. Tsitsigiannis D.I., Keller N.P. Oxylipins as developmental and host-fungal communication signals. Trends Microbiol 2007, 15:109-118.
166. Tsitsigiannis D.I., Kowieski T.M., Zarnowski R., Keller N.P. Three putative oxylipin biosynthetic genes integrate sexual and asexual development in Aspergillus nidulans. Microbiology 2005, 151:1809-1821.
167. Tunaru S., Althoff T.F., Nüsing R.M., Diener M., Offermanns S. Castor oil induces laxation and uterus contraction via ricinoleic acid activating prostaglandin EP3 receptors. Proc Natl Acad Sci U S A 2012, 109:9179-9184.
168. Van Bogaert I.N.A., Groeneboer S., Saerens K., Soetaert W. The role of cytochrome P450 monooxygenases in microbial fatty acid metabolism. FEBS J 2011, 278:206-221.
169. van de Loo F.J., Broun P., Turner S., Somerville C. An oleate 12-hydroxylase from Ricinus communis L. is a fatty acyl desaturase homolog. Proc Natl Acad Sci U S A 1995, 92:6743-6747.
170. Vance R.E., Hong S., Gronert K., Serhan C.N., Mekalanos J.J. The opportunistic pathogen Pseudomonas aeruginosa carries a secretable arachidonate 15-lipoxygenase. Proc Natl Acad Sci U S A 2004, 101:2135-2139.
171. Vidal-Mas J., Busquets M., Manresa A. Cloning and expression of a lipoxygenase from Pseudomonas aeruginosa 42A2. Antonie Van Leeuwenhoek 2005, 87:245-251.
172. Villaverde J.J., van der Vlist V., Santos S.A.O., Haarmann T., Langfelder K., Pirttimaa M., et al. Hydroperoxide production from linoleic acid by heterologous Gaeumannomyces graministritici lipoxygenase: optimization and scale-up. Chem Eng J 2013, 217:82-90.
173. Volkov A., Liavonchanka A., Kamneva O., Fiedler T., Goebel C., Kreikemeyer B., et al. Myosin cross-reactive antigen of Streptococcus pyogenes M49 encodes a fatty acid double bond hydratase that plays a role in oleic acid detoxification and bacterial virulence. J Biol Chem 2010, 285:10353-10361.
174. Waché Y., Aguedo M., Nicaud J.M., Belin J.M. Catabolism of hydroxyacids and biotechnological production of lactones by Yarrowia lipolytica. Appl Microbiol Biotechnol 2003, 61:393-404.
175. Waché Y., Husson F., Feron G., Belin J.M. Yeast as an efficient biocatalyst for the production of lipid-derived flavours and fragrances. Antonie Van Leeuwenhoek 2006, 89:405-416.
176. Wadman M., Zadelhoff G., Hamberg M., Visser T., Veldink G., Vliegenthart J.G. Conversion of linoleic acid into novel oxylipins by the mushroom Agaricus bisporus. Lipids 2005, 40:1163-1170.
177. Wadman M., de Vries R., Kalkhove S., Veldink G., Vliegenthart J. Characterization of oxylipins and dioxygenase genes in the asexual fungus Aspergillus niger. BMC Microbiol 2009, 9:59.
178. Wang X., Li L., Zheng Y., Zou H., Cao Y., Liu H., et al. Biosynthesis of long chain hydroxyfatty acids from glucose by engineered Escherichia coli. Bioresour Technol 2012, 114:561-566.
179. Wennman A., Jernerén F., Hamberg M., Oliw E.H. Catalytic convergence of manganese and iron lipoxygenases by replacement of a single amino acid. J Biol Chem 2012, 287:31757-31765.
180. Whent M., Ping T., Kenworthy W., Yu L. High-throughput assay for detection of soybean lipoxygenase-1. J Agric Food Chem 2010, 58:12602-12607.
181. Yu I.-S., Kim H.-J., Oh D.-K. Conversion of linoleic acid into 10-hydroxy-12(Z)-octadecenoic acid by whole cells of Stenotrophomonas nitritireducens. Biotechnol Prog 2008, 24:182-186.
182. Yu I.S., Yeom S.J., Kim H.J., Lee J.K., Kim Y.H., Oh D.K. Substrate specificity of Stenotrophomonas nitritireducens in the hydroxylation of unsaturated fatty acid. Appl Microbiol Biotechnol 2008, 78:157-163.
183. Zheng Y., Brash A.R. Dioxygenase activity of epidermal lipoxygenase-3 unveiled: typical and atypical features of its catalytic activity with natural and synthetic polyunsaturated fatty acids. J Biol Chem 2010, 285:39866-39875.