Identification of a functional allene oxide synthase-lipoxygenase fusion protein in the soft coral Gersemia fruticosa suggests the generality of this pathway in octocorals

Biochimica et Biophysica Acta - General Subjects

Volumn 1780, Issue 2, 2008, Pages 315-321

  Lõhelaid, Helike ^a   Järving, Reet ^a   Valmsen, Karin ^a   Varvas, Külliki ^a   Kreen, Malle ^a   Järving, Ivar ^a   Samel, Nigulas ^a  

^a TALLINN UNIVERSITY OF TECHNOLOGY   (Estonia)

Author keywords

Allene oxide synthase; AOS LOX; Coral; Gersemia fruticosa; HETE; LC MS; Lipoxygenase; Lipoxygenase peroxidase fusion protein

Indexed keywords

ALLENE DERIVATIVE; ALLENE OXIDE SYNTHASE; HYBRID PROTEIN; LIPOXYGENASE; SYNTHETASE; UNCLASSIFIED DRUG;

ARTICLE; CORAL; GERSEMIA FRUTICOSA; MOLECULAR CLONING; NUCLEOTIDE SEQUENCE; PLEXAURA HOMOMALLA; PRIORITY JOURNAL; PROTEIN EXPRESSION; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION;

AMINO ACID SEQUENCE; ANIMALS; ANTHOZOA; INTRAMOLECULAR OXIDOREDUCTASES; LIPOXYGENASE; MOLECULAR SEQUENCE DATA;

ALCYONACEA; ANTHOZOA; GERSEMIA FRUTICOSA; PLEXAURA HOMOMALLA;

EID: 38549155448     PISSN: 03044165     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbagen.2007.10.010     Document Type: Article

References (21)

1. Hamberg M. Fatty acid allene oxides. J. Am. Oil Chem. Soc. 66 (1989) 1445-1449
2. Hamberg M., and Gardner H.W. Oxylipin pathway to jasmonates: biochemistry and biological significance. Biochim. Biophys. Acta 1165 (1992) 1-18
3. Song W.C., Funk C.D., and Brash A.R. Molecular cloning of an allene oxide synthase: a cytochrome P450 specialized for the metabolism of fatty acid hydroperoxides. Proc. Natl. Acad. Sci. U. S. A. 90 (1993) 8519-8523
4. Brash A.R., Hughes M.A., Hawkins D.J., Boeglin W.E., Song W.-C., and Meijer L. Allene oxide and aldehyde biosynthesis in starfish oocytes. J. Biol. Chem. 266 (1991) 22926-22931
5. Corey E.J., d'Alarcao M., Matsuda S.P.T., and Lansbury P.T. Intermediacy of 8-R-HPETE in the conversion of arachidonic acid to pre-clavulone A by Clavularia viridis. Implication for the biosynthesis of marine prostanoids. J. Am. Chem. Soc. 109 (1987) 289-290
6. Brash A.R., Baertschi S.W., Ingram C.D., and Harris T.M. On non-cyclooxygenase prostaglandin synthesis in the sea whip coral, Plexaura homomalla: an 8(R)-lipoxygenase pathway leads to formation of an alpha-ketol and racemic prostanoid. J. Biol. Chem. 262 (1987) 15829-15839
7. Koljak R., Boutaud O., Shieh B.-H., Samel N., and Brash A.R. Identification of a naturally occurring peroxidase-lipoxygenase fusion protein. Science 277 (1997) 1994-1996
8. Boutaud O., and Brash A.R. Purification and catalytic activities of the two domains of the allene oxide synthase-lipoxygenase fusion protein of the coral Plexaura homomalla. J. Biol. Chem. 274 (1999) 33764-33770
9. Abraham B.D., Sono M., Boutaud O., Shriner A., Dawson J.H., Brash A.R., and Gaffney B.J. Characterization of the coral allene oxide synthase active site with UV- visible absorption, magnetic circular dichroism, and electron paramagneticresonance spectroscopy: evidence for tyrosinate ligation to the ferric enzyme heme iron. Biochemistry 40 7 (2001) 2251-2259
10. Oldham M.L., Brash A.R., and Newcomer M.E. The structure of coral allene oxide synthase reveals a catalase adapted for metabolism of a fatty acid hydroperoxide. Proc. Natl. Acad. Sci. U. S. A. 102 2 (2005) 297-302
11. Oldham M.L., Brash A.R., and Newcomer M.E. Insights from the X-ray crystal structure of coral 8R-lipoxygenase: calcium activation via a C2-like domain and a structural basis of product chirality. J. Biol. Chem. 280 (2005) 39545-39552
12. Varvas K., Järving I., Koljak R., Valmsen K., Brash A.R., and Samel N. Evidence of a cyclooxygenase-related prostaglandin synthesis in coral. The allene oxide pathway is not involved in prostaglandin biosynthesis. J. Biol. Chem. 274 (1999) 9923-9929
13. α from arachidonic acid. Tetrahedron Lett. 34 (1993) 3643-3646
14. Koljak R., Järving I., Kurg R., Boeglin W.E., Varvas K., Valmsen K., Ustav M., Brash A.R., and Samel N. The basis of prostaglandin synthesis in coral: molecular cloning and expression of a cyclooxygenase from the Arctic soft coral Gersemia fruticosa. J. Biol. Chem. 276 (2001) 7033-7040
15. Järving R., Järving I., Kurg R., Brash A.R., and Samel N. On the evolutionary origin of cyclooxygenase (COX) isozymes: characterization of marine invertebrate COX genes points to independent duplication events in vertebrate and invertebrate lineages. J. Biol. Chem. 279 (2004) 13624-13633
16. Mortimer M., Järving R., Brash A.R., Samel N., and Järving I. Identification and characterization of an arachidonate 11R- lipoxygenase. Arch. Biochem. Biophys. 445 (2006) 147-155
17. Tosha T., Uchida T., Brash A.R., and Kitagawa T. On the relationship of coral allene oxide synthase to catalase. A single active site mutation that induces catalase activity in coral allene oxide synthase. J. Biol. Chem. 281 (2006) 12610-12617
18. Hammarberg T., Provost P., Persson B., and Rådmark O. The N-terminal domain of 5-lipoxygenase binds calcium and mediates calcium stimulation of enzyme activity. J. Biol. Chem. 275 (2000) 38787-38793
19. Coffa G., and Brash A.B. 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. 101 (2004) 15579-15584
20. Varvas K., Koljak R., Järving I., Pehk T., and Samel N. Endoperoxide pathway in prostaglandin biosynthesis in the soft coral Gersemia fruticosa. Tetrahedron Lett. 35 (1994) 8267-8270
21. Tijet N., and Brash A.B. Allene oxide synthases and allene oxides. Prostaglandins Other Lipid Mediat. 68-69 (2002) 423-431