Steric analysis of 8-hydroxy- and 10-hydroxyoctadecadienoic acids and dihydroxyoctadecadienoic acids formed from 8R-hydroperoxyoctadecadienoic acid by hydroperoxide isomerases

Analytical Biochemistry

Volumn 367, Issue 2, 2007, Pages 238-246

  Garscha, Ulrike ^a   Oliw, Ernst H ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

5,8 DiHODE; 8,11 DiHODE; Aspergillus; Chiralcel OB; Ion trap mass spectrometry; Normal phase HPLC; Reprosil chiral NR

Indexed keywords

ASPERGILLUS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OXIDATION; SILICA;

5,8-DIHODE; 8,11-DIHODE; CHIRALCEL OB; ION-TRAP MASS SPECTROMETRY; NORMAL PHASE HPLC; REPROSIL CHIRAL-NR;

LINOLEIC ACID;

10 HYDROXYOCTADECADIENOIC ACID; 8 HYDROXYOCTADECADIENOIC ACID; BENZOIC ACID DERIVATIVE; CELLULOSE; HYDROPEROXIDE; HYDROPEROXYOCTADECADIENOIC ACID; HYDROXY FATTY ACID; HYDROXYACID; LIPOXYGENASE; SILICON DIOXIDE; SODIUM BOROHYDRIDE; UNCLASSIFIED DRUG;

AGARICUS BISPORUS; ARTICLE; ASPERGILLUS NIDULANS; DESS MARTIN OXIDATION; DIASTEREOISOMER; ELUTION; FATTY ACID ANALYSIS; FATTY ACID OXIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS; TANDEM MASS SPECTROMETRY;

AGARICUS BISPORUS; ASPERGILLUS; EMERICELLA NIDULANS; EPICHLOE TYPHINA; FUNGI; GAEUMANNOMYCES GRAMINIS; LENTINULA EDODES; TRITICUM AESTIVUM;

EID: 34347214029     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2007.04.045     Document Type: Article

References (30)

1. Bowers W.S., Hoch H.C., Evans P.H., and Katayama M. Thallophytic allelopathy: Isolation and identification of laetisaric acid. Science 232 (1986) 105-106
2. Brodowsky I.D., and Oliw E.H. Biosynthesis of 8R-hydroperoxylinoleic acid by the fungus Laetisaria arvalis. Biochim. Biophys. Acta 1168 (1993) 68-72
3. Champe S.P., and el-Zayat A.A. Isolation of a sexual sporulation hormone from Aspergillus nidulans. J. Bacteriol 171 (1989) 3982-3988
4. Mazur P., Meyers H.V., Nakanishi K., El-Zayat A.A.E., and Champe S.P. Structural elucidation of sporogenic fatty acid metabolites from Aspergillus nidulans. Tetrahedron Lett. 31 (1990) 3837-3840
5. Brodowsky I.D., and Oliw E.H. Metabolism of 18:2(n - 6), 18:3(n - 3), 20:4(n - 6) and 20:5(n - 3) by the fungus Gaeumannomyces graminis: identification of metabolites formed by 8-hydroxylation and by w2 and w3 oxygenation. Biochim. Biophys. Acta 1124 (1992) 59-65
6. Fox S.R., Akpinar A., Prabhune A.A., Friend J., and 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 35 (2000) 23-30
7. Brodowsky I.D., Hamberg M., and 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. 267 (1992) 14738-14745
8. Hamberg M., Gerwick W.H., and Åsén P.A. Linoleic acid metabolism in the red alga Lithothamnion corallioides: Biosynthesis of 11(R)-hydroxy-9(Z),12(Z)-octadecadienoic acid. Lipids 27 (1992) 487-493
9. Su C., and Oliw E.H. Purification and characterization of linoleate 8-dioxygenase from the fungus Gaeumannomyces graminis as a novel hemoprotein. J. Biol. Chem. 271 (1996) 14112-14118
10. Cristea M., Osbourn A.E., and Oliw E.H. Linoleate diol synthase of the rice blast fungus Magnaporthe grisea. Lipids 38 (2003) 1275-1280
11. Brash A.R. Lipoxygenases: occurrence, functions, catalysis, and acquisition of substrate. J. Biol. Chem. 274 (1999) 23679-23682
12. Coffa G., and 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. USA 101 (2004) 15579-15584
13. Wurzenberger M., and Grosch W. The formation of 1-octen-3-ol from the 10-hydroperoxide isomer of linoleic acid by a hydroperoxide lyase in mushrooms (Psalliota bispora). Biochim. Biophys. Acta 794 (1984) 25-30
14. Akakabe Y., Matsui K., and Kajiwara T. Stereochemical correlation between 10-hydroperoxyoctadecadienoic acid and 1-octen-3-ol in Lentinula edodes and Tricholoma matsutake mushrooms. Biosci. Biotechnol. Biochem. 69 (2005) 1539-1544
15. Koshino H., Togiya S., Yoshihara T., and Sakamura S. Four fungitoxic C-18 hydroxy unsaturated fatty acids from stromata of Epichloe typhina. Tetrahedron Lett. 28 (1987) 73-76
16. Brodowsky I.D., Zhang L.Y., Oliw E.H., and Hamberg M. Linoleic acid 8R-dioxygenase and hydroperoxide isomerase of the fungus Gaeumannomyces graminis. Mechanism of catalysis and inhibition. Ann. N. Y. Acad. Sci. 744 (1994) 314-316
17. Tsitsigiannis D.I., Kowieski T.M., Zarnowski R., and Keller N.P. Three putative oxylipin biosynthetic genes integrate sexual and asexual development in Aspergillus nidulans. Microbiology 151 (2005) 1809-1821
18. Tsitsigiannis D.I., Zarnowski R., and Keller N.P. The lipid body protein, PpoA, coordinates sexual and asexual sporulation in Aspergillus nidulans. J. Biol. Chem. 279 (2004) 11344-11353
19. Pel H.J., de Winde J.H., Archer D.B., Dyer P.S., Hofmann G., Schaap P.J., Turner G., de Vries R.P., Albang R., Albermann K., Andersen M.R., Bendtsen J.D., Benen J.A., van den Berg M., Breestraat S., Caddick M.X., Contreras R., Cornell M., Coutinho P.M., Danchin E.G., Debets A.J., Dekker P., van Dijck P.W., van Dijk A., Dijkhuizen L., Driessen A.J., d'Enfert C., Geysens S., Goosen C., Groot G.S., de Groot P.W., Guillemette T., Henrissat B., Herweijer M., van den Hombergh J.P., van den Hondel C.A., van der Heijden R.T., van der Kaaij R.M., Klis F.M., Kools H.J., Kubicek C.P., van Kuyk P.A., Lauber J., Lu X., van der Maarel M.J., Meulenberg R., Menke H., Mortimer M.A., Nielsen J., Oliver S.G., Olsthoorn M., Pal K., van Peij N.N., Ram A.F., Rinas U., Roubos J.A., Sagt C.M., Schmoll M., Sun J., Ussery D., Varga J., Vervecken W., van de Vondervoort P.J., Wedler H., Wosten H.A., Zeng A.P., van Ooyen A.J., Visser J., and Stam H. Genome sequencing and analysis of the versatile cell factory Aspergillus niger CBS 513.88. Nat. Biotechnol. 25 (2007) 221-231
20. Galagan J.E., Calvo S.E., Cuomo C., Ma L.J., Wortman J.R., Batzoglou S., Lee S.I., Basturkmen M., Spevak C.C., Clutterbuck J., Kapitonov V., Jurka J., Scazzocchio C., Farman M., Butler J., Purcell S., Harris S., Braus G.H., Draht O., Busch S., D'Enfert C., Bouchier C., Goldman G.H., Bell-Pedersen D., Griffiths-Jones S., Doonan J.H., Yu J., Vienken K., Pain A., Freitag M., Selker E.U., Archer D.B., Penalva M.A., Oakley B.R., Momany M., Tanaka T., Kumagai T., Asai K., Machida M., Nierman W.C., Denning D.W., Caddick M., Hynes M., Paoletti M., Fischer R., Miller B., Dyer P., Sachs M.S., Osmani S.A., and Birren B.W. Sequencing of Aspergillus nidulans and comparative analysis with A. fumigatus and A. oryzae. Nature 438 (2005) 1105-1115
21. U. Garscha, and E.H. Oliw, Expression and site-directed mutagenesis of linoleate 7,8-diol synthase reveals structural and catalytic similarities to cyclooxygenases and 5,8-diol synthases. manuscript, submitted (2007).
22. Wadman M.W., van Zadelhoff G., Hamberg M., Visser T., Veldink G.A., and Vliegenthart J.F. Conversion of linoleic acid into novel oxylipins by the mushroom Agaricus bisporus. Lipids 40 (2005) 1163-1170
23. Dess D.B., and Martin J.C. A Useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 species. J. Am. Chem. Soc. 113 (1991) 7277-7287
24. Cristea M., Engström Å., Su C., Hörnsten L., and Oliw E.H. Expression of manganese lipoxygenase in Pichia pastoris and site-directed mutagenesis of putative metal ligands. Arch. Biochem. Biophys. 434 (2005) 201-211
25. Oliw E.H., Su C., Skogström T., and Benthin G. Analysis of novel hydroperoxides and other metabolites of oleic, linoleic, and linolenic acids by liquid chromatography-mass spectrometry with ion trap MSn. Lipids 33 (1998) 843-852
26. Dess D.B., and Martin J.C. Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldekhydes and ketones. J. Am. Chem. Soc. 48 (1983) 4155-4156
27. Iacazio G. Easy access to various natural keto polyunsaturated fatty acids and their corresponding racemic alcohols. Chem. Phys. Lipids 125 (2003) 115-121
28. Hamberg M., Zhang L.Y., Brodowsky I.D., and Oliw E.H. Sequential oxygenation of linoleic acid in the fungus Gaeumannomyces graminis: stereochemistry of dioxygenase and hydroperoxide isomerase reactions. Arch. Biochem. Biophys. 309 (1994) 77-80
29. Clapp C.H., Strulson M., Rodriguez P.C., Lo R., and Novak M.J. Oxygenation of monounsaturated fatty acids by soybean lipoxygenase-1: Evidence for transient hydroperoxide formation. Biochemistry 45 (2006) 15884-15892
30. Champe S.P., Nagle D.L., and Yager L.N. Sexual sporulation. Prog. Ind. Microbiol. 29 (1994) 429-454