Alan R. Brash, Ph.D.

Professor

alan.brash@vanderbilt.edu

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Faculty Appointments
Professor of Pharmacology
Education
Ph.D., Pharmacology, University of Edinburgh, EdinburghB.A., Medical Sciences, University of Cambridge, Cambridge
Office Address
510A RRB
TN 6602
Research Description
We are interested in the mechanism of biosynthesis of oxygenated metabolites of arachidonic acid, and their role in pathophysiological processes. Dr Brash is also a member of the Chemistry-Biology Interface program. Three areas of current interest are the following:

(i) "R" and "S" Lipoxygenases Lipoxygenases catalyze the reaction of unsaturated fatty acids with molecular oxygen and thus form fatty acid hydroperoxides. The well known lipoxygenases purified, cloned, and sequenced from mammals and plants insert the O2 on a particular position along the fatty acid carbon chain and usually with ?S? stereochemistry. There exist, however, lipoxygenases that form the mirror image ?R? hydroperoxides. We are characterizing these enzymes to provide new perspectives on the enzyme-substrate interactions that are the basis of the specificity of all lipoxygenases.

(ii) Characterization of novel lipoxygenase pathways and the mechanism of biosynthesis of the products - The metabolism of arachidonic acid often leads to the formation of an unstable intermediate that can serve as the precursor of an array of products. One of the more recently discovered intermediates of lipoxygenase pathways is the class of epoxide known as the allene oxide. For the last few years we have been investigating the occurrence of allene oxides in animal systems, the nature of the enzyme that catalyzes the biosynthesis (a catalase-related protein recently cloned as one domain of a fusion protein with an 8R-lipoxygenase), the mechanism of this enzymatic reaction, and the structures of products that can be formed by enzymic or non-enzymic rearrangements of the allene epoxides.

(iii) Role of epithelial lipoxygenases Recently we identified two previously unrecognized human lipoxygenases. One of these enzymes, a second type of 15S lipoxygenase, appears to be expressed in epithelial tissues including skin, prostate, breast, lung, and cornea. The other is a 12R-lipoxygenase. We showed that this type of enzyme accounts for the accumulation of 12R-hydroxy-arachidonic acid (12R-HETE) in psoriasis. We are exploring the role of these enzymes in tissue inflammation, hyperplasia, and cancer.
Research Keywords
Biosynthesis of prostaglandins and lipoxygenase products
Publications
Teder T, Lõhelaid H, Boeglin WE, Calcutt WM, Brash AR, Samel N. A Catalase-related Hemoprotein in Coral Is Specialized for Synthesis of Short-chain Aldehydes: DISCOVERY OF P450-TYPE HYDROPEROXIDE LYASE ACTIVITY IN A CATALASE. J. Biol. Chem [print-electronic]. 2015 Aug 8/7/2015; 290(32): 19823-32. PMID: 26100625, PMCID: PMC4528142, PII: M115.660282, DOI: 10.1074/jbc.M115.660282, ISSN: 1083-351X.

Teder T, Boeglin WE, Brash AR. Lipoxygenase-catalyzed transformation of epoxy fatty acids to hydroxy-endoperoxides: a potential P450 and lipoxygenase interaction. J. Lipid Res [print-electronic]. 2014 Dec; 55(12): 2587-96. PMID: 25293588, PMCID: PMC4242451, PII: jlr.M054072, DOI: 10.1194/jlr.M054072, ISSN: 0022-2275.

Neau DB, Bender G, Boeglin WE, Bartlett SG, Brash AR, Newcomer ME. Crystal structure of a lipoxygenase in complex with substrate: the arachidonic acid-binding site of 8R-lipoxygenase. J. Biol. Chem [print-electronic]. 2014 Nov 11/14/2014; 289(46): 31905-13. PMID: 25231982, PMCID: PMC4231669, PII: M114.599662, DOI: 10.1074/jbc.M114.599662, ISSN: 1083-351X.

Mashhadi Z, Boeglin WE, Brash AR. Inhibitory effects of a novel Val to Thr mutation on the distal heme of human catalase. Biochimie [print-electronic]. 2014 Nov; 106: 180-3. PMID: 25086217, PMCID: PMC4250446, PII: S0300-9084(14)00212-0, DOI: 10.1016/j.biochi.2014.07.021, ISSN: 1638-6183.

Brash AR, Niraula NP, Boeglin WE, Mashhadi Z. An ancient relative of cyclooxygenase in cyanobacteria is a linoleate 10S-dioxygenase that works in tandem with a catalase-related protein with specific 10S-hydroperoxide lyase activity. J. Biol. Chem [print-electronic]. 2014 May 5/9/2014; 289(19): 13101-11. PMID: 24659780, PMCID: PMC4036322, PII: M114.555904, DOI: 10.1074/jbc.M114.555904, ISSN: 1083-351X.

Muñoz-Garcia A, Thomas CP, Keeney DS, Zheng Y, Brash AR. The importance of the lipoxygenase-hepoxilin pathway in the mammalian epidermal barrier. Biochim. Biophys. Acta [print-electronic]. 2014 Mar; 1841(3): 401-8. PMID: 24021977, PMCID: PMC4116325, PII: S1388-1981(13)00191-1, DOI: 10.1016/j.bbalip.2013.08.020, ISSN: 0006-3002.

Brash AR, Boeglin WE, Stec DF, Voehler M, Schneider C, Cha JK. Isolation and characterization of two geometric allene oxide isomers synthesized from 9S-hydroperoxylinoleic acid by cytochrome P450 CYP74C3: stereochemical assignment of natural fatty acid allene oxides. J. Biol. Chem [print-electronic]. 2013 Jul 7/19/2013; 288(29): 20797-806. PMID: 23709224, PMCID: PMC3774351, PII: M113.482521, DOI: 10.1074/jbc.M113.482521, ISSN: 1083-351X.

Jin J, Zheng Y, Brash AR. Demonstration of HNE-related aldehyde formation via lipoxygenase-catalyzed synthesis of a bis-allylic dihydroperoxide intermediate. Chem. Res. Toxicol [print-electronic]. 2013 Jun 6/17/2013; 26(6): 896-903. PMID: 23668325, PMCID: PMC3719183, DOI: 10.1021/tx4000396, ISSN: 1520-5010.

Jin J, Zheng Y, Boeglin WE, Brash AR. Biosynthesis, isolation, and NMR analysis of leukotriene A epoxides: substrate chirality as a determinant of the cis or trans epoxide configuration. J. Lipid Res [print-electronic]. 2013 Mar; 54(3): 754-61. PMID: 23242647, PMCID: PMC3617949, PII: jlr.M033746, DOI: 10.1194/jlr.M033746, ISSN: 0022-2275.

Thomas CP, Boeglin WE, Garcia-Diaz Y, O'Donnell VB, Brash AR. Steric analysis of epoxyalcohol and trihydroxy derivatives of 9-hydroperoxy-linoleic acid from hematin and enzymatic synthesis. Chem. Phys. Lipids [print-electronic]. 2013 Feb; 167-168: 21-32. PMID: 23352713, PMCID: PMC3678760, PII: S0009-3084(13)00003-0, DOI: 10.1016/j.chemphyslip.2013.01.002, ISSN: 1873-2941.

Boeglin WE, Brash AR. Cytochrome P450-type hydroxylation and epoxidation in a tyrosine-liganded hemoprotein, catalase-related allene oxide synthase. J. Biol. Chem [print-electronic]. 2012 Jul 7/13/2012; 287(29): 24139-47. PMID: 22628547, PMCID: PMC3397841, PII: M112.364216, DOI: 10.1074/jbc.M112.364216, ISSN: 1083-351X.

Jin J, Boeglin WE, Cha JK, Brash AR. 8R-Lipoxygenase-catalyzed synthesis of a prominent cis-epoxyalcohol from dihomo-¿-linolenic acid: a distinctive transformation compared with S-lipoxygenases. J. Lipid Res [print-electronic]. 2012 Feb; 53(2): 292-9. PMID: 22158855, PMCID: PMC3269157, PII: jlr.M022863, DOI: 10.1194/jlr.M022863, ISSN: 0022-2275.

Brash AR, Schneider C, Hamberg M. Applications of stereospecifically-labeled Fatty acids in oxygenase and desaturase biochemistry. Lipids [print-electronic]. 2012 Feb; 47(2): 101-16. PMID: 21971646, PMCID: PMC3315059, DOI: 10.1007/s11745-011-3612-7, ISSN: 1558-9307.

Bandara DM, Sono M, Bruce GS, Brash AR, Dawson JH. Coordination modes of tyrosinate-ligated catalase-type heme enzymes: magnetic circular dichroism studies of Plexaura homomalla allene oxide synthase, Mycobacterium avium ssp. paratuberculosis protein-2744c, and bovine liver catalase in their ferric and ferrous states. J. Inorg. Biochem [print-electronic]. 2011 Dec; 105(12): 1786-94. PMID: 22104301, PMCID: PMC3482475, PII: S0162-0134(11)00282-0, DOI: 10.1016/j.jinorgbio.2011.09.026, ISSN: 1873-3344.

Zheng Y, Yin H, Boeglin WE, Elias PM, Crumrine D, Beier DR, Brash AR. Lipoxygenases mediate the effect of essential fatty acid in skin barrier formation: a proposed role in releasing omega-hydroxyceramide for construction of the corneocyte lipid envelope. J. Biol. Chem [print-electronic]. 2011 Jul 7/8/2011; 286(27): 24046-56. PMID: 21558561, PMCID: PMC3129186, PII: M111.251496, DOI: 10.1074/jbc.M111.251496, ISSN: 1083-351X.

Gilbert NC, Bartlett SG, Waight MT, Neau DB, Boeglin WE, Brash AR, Newcomer ME. The structure of human 5-lipoxygenase. Science. 2011 Jan 1/14/2011; 331(6014): 217-9. PMID: 21233389, PMCID: PMC3245680, PII: 331/6014/217, DOI: 10.1126/science.1197203, ISSN: 1095-9203.

Liu W, Porter NA, Schneider C, Brash AR, Yin H. Formation of 4-hydroxynonenal from cardiolipin oxidation: Intramolecular peroxyl radical addition and decomposition. Free Radic. Biol. Med [print-electronic]. 2011 Jan 1/1/2011; 50(1): 166-78. PMID: 21047551, PMCID: PMC3014443, PII: S0891-5849(10)01348-1, DOI: 10.1016/j.freeradbiomed.2010.10.709, ISSN: 1873-4596.

Zheng Y, Brash AR. On the role of molecular oxygen in lipoxygenase activation: comparison and contrast of epidermal lipoxygenase-3 with soybean lipoxygenase-1. J. Biol. Chem [print-electronic]. 2010 Dec 12/17/2010; 285(51): 39876-87. PMID: 20923767, PMCID: PMC3000969, PII: M110.180794, DOI: 10.1074/jbc.M110.180794, ISSN: 1083-351X.

Zheng Y, Brash AR. 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 [print-electronic]. 2010 Dec 12/17/2010; 285(51): 39866-75. PMID: 20921226, PMCID: PMC3000968, PII: M110.155374, DOI: 10.1074/jbc.M110.155374, ISSN: 1083-351X.

Zheng Y, Brash AR. Formation of a cyclopropyl epoxide via a leukotriene A synthase-related pathway in an anaerobic reaction of soybean lipoxygenase-1 with 15S-hydroperoxyeicosatetraenoic acid: evidence that oxygen access is a determinant of secondary reactions with fatty acid hydroperoxides. J. Biol. Chem [print-electronic]. 2010 Apr 4/30/2010; 285(18): 13427-36. PMID: 20194505, PMCID: PMC2859502, PII: M109.084632, DOI: 10.1074/jbc.M109.084632, ISSN: 1083-351X.

Gao B, Boeglin WE, Brash AR. Omega-3 fatty acids are oxygenated at the n-7 carbon by the lipoxygenase domain of a fusion protein in the cyanobacterium Acaryochloris marina. Biochim. Biophys. Acta [print-electronic]. 2010 Jan; 1801(1): 58-63. PMID: 19786119, PMCID: PMC2787963, PII: S1388-1981(09)00208-X, DOI: 10.1016/j.bbalip.2009.09.004, ISSN: 0006-3002.

Pakhomova S, Gao B, Boeglin WE, Brash AR, Newcomer ME. The structure and peroxidase activity of a 33-kDa catalase-related protein from Mycobacterium avium ssp. paratuberculosis. Protein Sci. 2009 Dec; 18(12): 2559-68. PMID: 19827095, PMCID: PMC2821274, DOI: 10.1002/pro.265, ISSN: 1469-896X.

Brash AR. Mechanistic aspects of CYP74 allene oxide synthases and related cytochrome P450 enzymes. Phytochemistry [print-electronic]. 2009 Sep; 70(13-14): 1522-31. PMID: 19747698, PMCID: PMC2783490, PII: S0031-9422(09)00338-0, DOI: 10.1016/j.phytochem.2009.08.005, ISSN: 1873-3700.

Neau DB, Gilbert NC, Bartlett SG, Boeglin W, Brash AR, Newcomer ME. The 1.85 A structure of an 8R-lipoxygenase suggests a general model for lipoxygenase product specificity. Biochemistry. 2009 Aug 8/25/2009; 48(33): 7906-15. PMID: 19594169, DOI: 10.1021/bi900084m, ISSN: 1520-4995.

Gao B, Boeglin WE, Zheng Y, Schneider C, Brash AR. Evidence for an ionic intermediate in the transformation of fatty acid hydroperoxide by a catalase-related allene oxide synthase from the Cyanobacterium Acaryochloris marina. J. Biol. Chem [print-electronic]. 2009 Aug 8/14/2009; 284(33): 22087-98. PMID: 19531485, PMCID: PMC2755933, PII: M109.013151, DOI: 10.1074/jbc.M109.013151, ISSN: 0021-9258.

Niisuke K, Boeglin WE, Murray JJ, Schneider C, Brash AR. Biosynthesis of a linoleic acid allylic epoxide: mechanistic comparison with its chemical synthesis and leukotriene A biosynthesis. J. Lipid Res [print-electronic]. 2009 Jul; 50(7): 1448-55. PMID: 19244216, PMCID: PMC2694342, PII: M900025-JLR200, DOI: 10.1194/jlr.M900025-JLR200, ISSN: 0022-2275.

Boeglin WE, Itoh A, Zheng Y, Coffa G, Howe GA, Brash AR. Investigation of substrate binding and product stereochemistry issues in two linoleate 9-lipoxygenases. Lipids [print-electronic]. 2008 Nov; 43(11): 979-87. PMID: 18795358, DOI: 10.1007/s11745-008-3230-1, ISSN: 0024-4201.

Gilbert NC, Niebuhr M, Tsuruta H, Bordelon T, Ridderbusch O, Dassey A, Brash AR, Bartlett SG, Newcomer ME. A covalent linker allows for membrane targeting of an oxylipin biosynthetic complex. Biochemistry [print-electronic]. 2008 Oct 10/7/2008; 47(40): 10665-76. PMID: 18785758, PMCID: PMC2665874, DOI: 10.1021/bi800751p, ISSN: 1520-4995.

Gao B, Boeglin WE, Brash AR. Role of the conserved distal heme asparagine of coral allene oxide synthase (Asn137) and human catalase (Asn148): mutations affect the rate but not the essential chemistry of the enzymatic transformations. Arch. Biochem. Biophys [print-electronic]. 2008 Sep 9/15/2008; 477(2): 285-90. PMID: 18652800, PMCID: PMC2598388, PII: S0003-9861(08)00349-4, DOI: 10.1016/j.abb.2008.07.011, ISSN: 1096-0384.

Schneider C, Porter NA, Brash AR. Routes to 4-hydroxynonenal: fundamental issues in the mechanisms of lipid peroxidation. J. Biol. Chem [print-electronic]. 2008 Jun 6/6/2008; 283(23): 15539-43. PMID: 18285327, PMCID: PMC2414272, PII: R800001200, DOI: 10.1074/jbc.R800001200, ISSN: 0021-9258.

Schneider C, Boeglin WE, Yin H, Porter NA, Brash AR. Intermolecular peroxyl radical reactions during autoxidation of hydroxy and hydroperoxy arachidonic acids generate a novel series of epoxidized products. Chem. Res. Toxicol [print-electronic]. 2008 Apr; 21(4): 895-903. PMID: 18324788, DOI: 10.1021/tx700357u, ISSN: 0893-228X.

Zheng Y, Boeglin WE, Schneider C, Brash AR. A 49-kDa mini-lipoxygenase from Anabaena sp. PCC 7120 retains catalytically complete functionality. J. Biol. Chem [print-electronic]. 2008 Feb 2/22/2008; 283(8): 5138-47. PMID: 18070874, PII: M705780200, DOI: 10.1074/jbc.M705780200, ISSN: 0021-9258.

Gilbert NC, Niebuhr M, Tsuruta H, Bordelon T, Ridderbusch O, Dassey A, Brash AR, Bartlett SG, Newcomer ME. A covalent linker allows for membrane targeting of an oxylipin biosynthetic complex. Biochemistry. 2008; 47((40)): 10665-76.

Schneider C, Niisuke K, Boeglin WE, Voehler M, Stec DF, Porter NA, Brash AR. Enzymatic synthesis of a bicyclobutane fatty acid by a hemoprotein lipoxygenase fusion protein from the cyanobacterium Anabaena PCC 7120. Proc. Natl. Acad. Sci. U.S.A [print-electronic]. 2007 Nov 11/27/2007; 104(48): 18941-5. PMID: 18025466, PMCID: PMC2141887, PII: 0707148104, DOI: 10.1073/pnas.0707148104, ISSN: 1091-6490.

Rector CL, Stec DF, Brash AR, Porter NA. Identification of the peroxidation products of 13-hydroxy-gamma-linolenate and 15-hydroxyarachidonate: mechanistic studies on the formation of leukotriene-like diols. Chem. Res. Toxicol [print-electronic]. 2007 Nov; 20(11): 1582-93. PMID: 17907784, DOI: 10.1021/tx700120r, ISSN: 0893-228X.

Valmsen K, Boeglin WE, Järving R, Järving I, Varvas K, Brash AR, Samel N. A critical role of non-active site residues on cyclooxygenase helices 5 and 6 in the control of prostaglandin stereochemistry at carbon 15. J. Biol. Chem [print-electronic]. 2007 Sep 9/21/2007; 282(38): 28157-63. PMID: 17652088, PII: M704950200, DOI: 10.1074/jbc.M704950200, ISSN: 0021-9258.

Moran JL, Qiu H, Turbe-Doan A, Yun Y, Boeglin WE, Brash AR, Beier DR. A mouse mutation in the 12R-lipoxygenase, Alox12b, disrupts formation of the epidermal permeability barrier. J. Invest. Dermatol [print-electronic]. 2007 Aug; 127(8): 1893-7. PMID: 17429434, PII: 5700825, DOI: 10.1038/sj.jid.5700825, ISSN: 1523-1747.

Brash AR, Yu Z, Boeglin WE, Schneider C. The hepoxilin connection in the epidermis. FEBS J [print-electronic]. 2007 Jul; 274(14): 3494-502. PMID: 17608720, PII: EJB5909, DOI: 10.1111/j.1742-4658.2007.05909.x, ISSN: 1742-464X.

Yu Z, Schneider C, Boeglin WE, Brash AR. Epidermal lipoxygenase products of the hepoxilin pathway selectively activate the nuclear receptor PPARalpha. Lipids [print-electronic]. 2007 Jun; 42(6): 491-7. PMID: 17436029, DOI: 10.1007/s11745-007-3054-4, ISSN: 0024-4201.

Schneider C, Pratt DA, Porter NA, Brash AR. Control of oxygenation in lipoxygenase and cyclooxygenase catalysis. Chem. Biol. 2007 May; 14(5): 473-88. PMID: 17524979, PMCID: PMC2692746, PII: S1074-5521(07)00145-7, DOI: 10.1016/j.chembiol.2007.04.007, ISSN: 1074-5521.

Schneider C, Yu Z, Boeglin WE, Zheng Y, Brash AR. Enantiomeric separation of hydroxy and hydroperoxy eicosanoids by chiral column chromatography. Meth. Enzymol. 2007; 433: 145-57. PMID: 17954233, PII: S0076-6879(07)33008-5, DOI: 10.1016/S0076-6879(07)33008-5, ISSN: 0076-6879.

Yu Z, Schneider C, Boeglin WE, Brash AR. Human and mouse eLOX3 have distinct substrate specificities: implications for their linkage with lipoxygenases in skin. Arch. Biochem. Biophys [print-electronic]. 2006 Nov 11/15/2006; 455(2): 188-96. PMID: 17045234, PMCID: PMC2636205, PII: S0003-9861(06)00331-6, DOI: 10.1016/j.abb.2006.09.002, ISSN: 0003-9861.

Melner MH, Haas AL, Klein JM, Brash AR, Boeglin WE, Nagdas SK, Winfrey VP, Olson GE. Demonstration of ubiquitin thiolester formation of UBE2Q2 (UBCi), a novel ubiquitin-conjugating enzyme with implantation site-specific expression. Biol. Reprod [print-electronic]. 2006 Sep; 75(3): 395-406. PMID: 16760379, PII: biolreprod.106.051458, DOI: 10.1095/biolreprod.106.051458, ISSN: 0006-3363.

Chen B, Tsui S, Boeglin WE, Douglas RS, Brash AR, Smith TJ. Interleukin-4 induces 15-lipoxygenase-1 expression in human orbital fibroblasts from patients with Graves disease. Evidence for anatomic site-selective actions of Th2 cytokines. J. Biol. Chem [print-electronic]. 2006 Jul 7/7/2006; 281(27): 18296-306. PMID: 16675443, PII: M603484200, DOI: 10.1074/jbc.M603484200, ISSN: 0021-9258.

Tosha T, Uchida T, Brash AR, 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 [print-electronic]. 2006 May 5/5/2006; 281(18): 12610-7. PMID: 16513636, PII: M600061200, DOI: 10.1074/jbc.M600061200, ISSN: 0021-9258.

Furse KE, Pratt DA, Schneider C, Brash AR, Porter NA, Lybrand TP. Molecular dynamics simulations of arachidonic acid-derived pentadienyl radical intermediate complexes with COX-1 and COX-2: insights into oxygenation regio- and stereoselectivity. Biochemistry. 2006 Mar 3/14/2006; 45(10): 3206-18. PMID: 16519515, PMCID: PMC2504531, DOI: 10.1021/bi052338h, ISSN: 0006-2960.

Mortimer M, Järving R, Brash AR, Samel N, Järving I. Identification and characterization of an arachidonate 11R-lipoxygenase. Arch. Biochem. Biophys [print-electronic]. 2006 Jan 1/1/2006; 445(1): 147-55. PMID: 16321357, PII: S0003-9861(05)00445-5, DOI: 10.1016/j.abb.2005.10.023, ISSN: 0003-9861.

Coffa G, Schneider C, Brash AR. A comprehensive model of positional and stereo control in lipoxygenases. Biochem. Biophys. Res. Commun [print-electronic]. 2005 Dec 12/9/2005; 338(1): 87-92. PMID: 16111652, PII: S0006-291X(05)01688-8, DOI: 10.1016/j.bbrc.2005.07.185, ISSN: 0006-291X.

Oldham ML, Brash AR, Newcomer ME. 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 [print-electronic]. 2005 Nov 11/25/2005; 280(47): 39545-52. PMID: 16162493, PII: M506675200, DOI: 10.1074/jbc.M506675200, ISSN: 0021-9258.

Coffa G, Imber AN, Maguire BC, Laxmikanthan G, Schneider C, Gaffney BJ, Brash AR. On the relationships of substrate orientation, hydrogen abstraction, and product stereochemistry in single and double dioxygenations by soybean lipoxygenase-1 and its Ala542Gly mutant. J. Biol. Chem [print-electronic]. 2005 Nov 11/18/2005; 280(46): 38756-66. PMID: 16157595, PMCID: PMC1351262, PII: M504870200, DOI: 10.1074/jbc.M504870200, ISSN: 0021-9258.

Schneider C, Boeglin WE, Yin H, Ste DF, Hachey DL, Porter NA, Brash AR. Synthesis of dihydroperoxides of linoleic and linolenic acids and studies on their transformation to 4-hydroperoxynonenal. Lipids. 2005 Nov; 40(11): 1155-62. PMID: 16459928, ISSN: 0024-4201.

Gutschow CA, Collet P, Prenzel K, Hölscher AH, Schneider PM. Long-term results and gastroesophageal reflux in a series of laparoscopic adjustable gastric banding. J. Gastrointest. Surg. 2005 Sep; 9(7): 941-8. PMID: 16137589, PII: S1091-255X(05)00331-8, DOI: 10.1016/j.gassur.2005.02.001, ISSN: 1091-255X.

Chang MS, Schneider C, Roberts RL, Shappell SB, Haselton FR, Boeglin WE, Brash AR. Detection and subcellular localization of two 15S-lipoxygenases in human cornea. Invest. Ophthalmol. Vis. Sci. 2005 Mar; 46(3): 849-56. PMID: 15728540, PII: 46/3/849, DOI: 10.1167/iovs.04-1166, ISSN: 0146-0404.

Oldham ML, Brash AR, Newcomer ME. 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 [print-electronic]. 2005 Jan 1/11/2005; 102(2): 297-302. PMID: 15625113, PMCID: PMC544295, PII: 0406352102, DOI: 10.1073/pnas.0406352102, ISSN: 0027-8424.

Yu Z, Schneider C, Boeglin WE, Brash AR. Mutations associated with a congenital form of ichthyosis (NCIE) inactivate the epidermal lipoxygenases 12R-LOX and eLOX3. Biochim. Biophys. Acta. 2005 Jan 1/5/2005; 1686(3): 238-47. PMID: 15629692, PII: S1388-1981(04)00184-2, DOI: 10.1016/j.bbalip.2004.10.007, ISSN: 0006-3002.

Schneider C, Boeglin WE, Brash AR. Human cyclo-oxygenase-1 and an alternative splice variant: contrasts in expression of mRNA, protein and catalytic activities. Biochem. J. 2005 Jan 1/1/2005; 385(Pt 1): 57-64. PMID: 15361066, PMCID: PMC1134673, PII: BJ20041115, DOI: 10.1042/BJ20041115, ISSN: 1470-8728.

Coffa G, Brash AR. 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 [print-electronic]. 2004 Nov 11/2/2004; 101(44): 15579-84. PMID: 15496467, PMCID: PMC524819, PII: 0406727101, DOI: 10.1073/pnas.0406727101, ISSN: 0027-8424.

Valmsen K, Boeglin WE, Järving I, Schneider C, Varvas K, Brash AR, Samel N. Structural and functional comparison of 15S- and 15R-specific cyclooxygenases from the coral Plexaura homomalla. Eur. J. Biochem. 2004 Sep; 271(17): 3533-8. PMID: 15317588, PII: EJB4289, DOI: 10.1111/j.0014-2956.2004.04289.x, ISSN: 0014-2956.

Schneider C, Porter NA, Brash AR. Autoxidative transformation of chiral omega6 hydroxy linoleic and arachidonic acids to chiral 4-hydroxy-2E-nonenal. Chem. Res. Toxicol. 2004 Jul; 17(7): 937-41. PMID: 15257619, DOI: 10.1021/tx049913n, ISSN: 0893-228X.

Järving R, Järving I, Kurg R, Brash AR, 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 [print-electronic]. 2004 Apr 4/2/2004; 279(14): 13624-33. PMID: 14732711, PII: M313258200, DOI: 10.1074/jbc.M313258200, ISSN: 0021-9258.

West JD, Ji C, Duncan ST, Amarnath V, Schneider C, Rizzo CJ, Brash AR, Marnett LJ. Induction of apoptosis in colorectal carcinoma cells treated with 4-hydroxy-2-nonenal and structurally related aldehydic products of lipid peroxidation. Chem. Res. Toxicol. 2004 Apr; 17(4): 453-62. PMID: 15089087, DOI: 10.1021/tx034248o, ISSN: 0893-228X.

Schneider C, Strayhorn WD, Brantley DM, Nanney LB, Yull FE, Brash AR. Upregulation of 8-lipoxygenase in the dermatitis of IkappaB-alpha-deficient mice. J. Invest. Dermatol. 2004 Mar; 122(3): 691-8. PMID: 15086555, PII: JID22329, DOI: 10.1111/j.0022-202X.2004.22329.x, ISSN: 0022-202X.

Schneider C, Boeglin WE, Brash AR. Identification of two cyclooxygenase active site residues, Leucine 384 and Glycine 526, that control carbon ring cyclization in prostaglandin biosynthesis. J. Biol. Chem [print-electronic]. 2004 Feb 2/6/2004; 279(6): 4404-14. PMID: 14594816, PII: M307431200, DOI: 10.1074/jbc.M307431200, ISSN: 0021-9258.

Melner MH, Ducharme NA, Brash AR, Winfrey VP, Olson GE. Differential expression of genes in the endometrium at implantation: upregulation of a novel member of the E2 class of ubiquitin-conjugating enzymes. Biol. Reprod [print-electronic]. 2004 Feb; 70(2): 406-14. PMID: 14561654, PII: biolreprod.103.020719, DOI: 10.1095/biolreprod.103.020719, ISSN: 0006-3363.

Yu Z, Schneider C, Boeglin WE, Marnett LJ, Brash AR. The lipoxygenase gene ALOXE3 implicated in skin differentiation encodes a hydroperoxide isomerase. Proc. Natl. Acad. Sci. U.S.A [print-electronic]. 2003 Aug 8/5/2003; 100(16): 9162-7. PMID: 12881489, PMCID: PMC170889, PII: 1633612100, DOI: 10.1073/pnas.1633612100, ISSN: 0027-8424.

Shappell SB, Olson SJ, Hannah SE, Manning S, Roberts RL, Masumori N, Jisaka M, Boeglin WE, Vader V, Dave DS, Shook MF, Thomas TZ, Funk CD, Brash AR, Matusik RJ. Elevated expression of 12/15-lipoxygenase and cyclooxygenase-2 in a transgenic mouse model of prostate carcinoma. Cancer Res. 2003 May 5/1/2003; 63(9): 2256-67. PMID: 12727848, ISSN: 0008-5472.

Thuillier P, Brash AR, Kehrer JP, Stimmel JB, Leesnitzer LM, Yang P, Newman RA, Fischer SM. Inhibition of peroxisome proliferator-activated receptor (PPAR)-mediated keratinocyte differentiation by lipoxygenase inhibitors. Biochem. J. 2002 Sep 9/15/2002; 366(Pt 3): 901-10. PMID: 12069687, PMCID: PMC1222830, PII: BJ20020377, DOI: 10.1042/BJ20020377, ISSN: 0264-6021.

Tijet N, Brash AR. Allene oxide synthases and allene oxides. Prostaglandins Other Lipid Mediat. 2002 Aug; 68-69: 423-31. PMID: 12432934, ISSN: 1098-8823.

Schneider C, Brash AR. Lipoxygenase-catalyzed formation of R-configuration hydroperoxides. Prostaglandins Other Lipid Mediat. 2002 Aug; 68-69: 291-301. PMID: 12432924, ISSN: 1098-8823.

Kozak KR, Gupta RA, Moody JS, Ji C, Boeglin WE, DuBois RN, Brash AR, Marnett LJ. 15-Lipoxygenase metabolism of 2-arachidonylglycerol. Generation of a peroxisome proliferator-activated receptor alpha agonist. J. Biol. Chem [print-electronic]. 2002 Jun 6/28/2002; 277(26): 23278-86. PMID: 11956198, PII: M201084200, DOI: 10.1074/jbc.M201084200, ISSN: 0021-9258.

Schneider C, Manier ML, Hachey DL, Brash AR. Detection of the 15-acetate of prostaglandin E2 methyl ester as a prominent component of the prostaglandins in the gorgonian coral Plexaura homomalla. Lipids. 2002 Feb; 37(2): 217-21. PMID: 11908914, ISSN: 0024-4201.

Schneider C, Boeglin WE, Prusakiewicz JJ, Rowlinson SW, Marnett LJ, Samel N, Brash AR. Control of prostaglandin stereochemistry at the 15-carbon by cyclooxygenases-1 and -2. A critical role for serine 530 and valine 349. J. Biol. Chem [print-electronic]. 2002 Jan 1/4/2002; 277(1): 478-85. PMID: 11677234, PII: M107471200, DOI: 10.1074/jbc.M107471200, ISSN: 0021-9258.

Schneider C, Boeglin WE, Brash AR. Analysis of cyclooxygenase-substrate interactions using stereospecifically-labeled arachidonic acids. Adv. Exp. Med. Biol. 2002; 507: 49-53. PMID: 12664563, ISSN: 0065-2598.

Valmsen K, Järving I, Boeglin WE, Varvas K, Koljak R, Pehk T, Brash AR, Samel N. The origin of 15R-prostaglandins in the Caribbean coral Plexaura homomalla: molecular cloning and expression of a novel cyclooxygenase. Proc. Natl. Acad. Sci. U.S.A [print-electronic]. 2001 Jul 7/3/2001; 98(14): 7700-5. PMID: 11427702, PMCID: PMC35405, PII: 131022398, DOI: 10.1073/pnas.131022398, ISSN: 0027-8424.

Shappell SB, Manning S, Boeglin WE, Guan YF, Roberts RL, Davis L, Olson SJ, Jack GS, Coffey CS, Wheeler TM, Breyer MD, Brash AR. Alterations in lipoxygenase and cyclooxygenase-2 catalytic activity and mRNA expression in prostate carcinoma. Neoplasia. 2001 Jul; 3(4): 287-303. PMID: 11571629, PMCID: PMC1505867, DOI: 10.1038/sj/neo/7900166, ISSN: 1522-8002.

Shappell SB, Keeney DS, Zhang J, Page R, Olson SJ, Brash AR. 15-Lipoxygenase-2 expression in benign and neoplastic sebaceous glands and other cutaneous adnexa. J. Invest. Dermatol. 2001 Jul; 117(1): 36-43. PMID: 11442747, PII: jid1378, DOI: 10.1046/j.1523-1747.2001.01378.x, ISSN: 0022-202X.

Schneider C, Tallman KA, Porter NA, Brash AR. Two distinct pathways of formation of 4-hydroxynonenal. Mechanisms of nonenzymatic transformation of the 9- and 13-hydroperoxides of linoleic acid to 4-hydroxyalkenals. J. Biol. Chem [print-electronic]. 2001 Jun 6/15/2001; 276(24): 20831-8. PMID: 11259420, PII: M101821200, DOI: 10.1074/jbc.M101821200, ISSN: 0021-9258.

Brash AR. Arachidonic acid as a bioactive molecule. J. Clin. Invest. 2001 Jun; 107(11): 1339-45. PMID: 11390413, PMCID: PMC209328, DOI: 10.1172/JCI13210, ISSN: 0021-9738.

Koljak R, Järving I, Kurg R, Boeglin WE, Varvas K, Valmsen K, Ustav M, Brash AR, 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 [print-electronic]. 2001 Mar 3/9/2001; 276(10): 7033-40. PMID: 11085996, PII: M009803200, DOI: 10.1074/jbc.M009803200, ISSN: 0021-9258.

Abraham BD, Sono M, Boutaud O, Shriner A, Dawson JH, Brash AR, Gaffney BJ. Characterization of the coral allene oxide synthase active site with UV-visible absorption, magnetic circular dichroism, and electron paramagnetic resonance spectroscopy: evidence for tyrosinate ligation to the ferric enzyme heme iron. Biochemistry. 2001 Feb 2/20/2001; 40(7): 2251-9. PMID: 11329294, PII: bi002121h, ISSN: 0006-2960.

Tijet N, Schneider C, Muller BL, Brash AR. Biogenesis of volatile aldehydes from fatty acid hydroperoxides: molecular cloning of a hydroperoxide lyase (CYP74C) with specificity for both the 9- and 13-hydroperoxides of linoleic and linolenic acids. Arch. Biochem. Biophys. 2001 Feb 2/15/2001; 386(2): 281-9. PMID: 11368353, PII: S0003-9861(00)92218-5, DOI: 10.1006/abbi.2000.2218, ISSN: 0003-9861.

Schneider C, Keeney DS, Boeglin WE, Brash AR. Detection and cellular localization of 12R-lipoxygenase in human tonsils. Arch. Biochem. Biophys. 2001 Feb 2/15/2001; 386(2): 268-74. PMID: 11368351, PII: S0003-9861(00)92217-3, DOI: 10.1006/abbi.2000.2217, ISSN: 0003-9861.

Jisaka M, Boeglin WE, Kim RB, Brash AR. Site-directed mutagenesis studies on a putative fifth iron ligand of mouse 8S-lipoxygenase: retention of catalytic activity on mutation of serine-558 to asparagine, histidine, or alanine. Arch. Biochem. Biophys. 2001 Feb 2/15/2001; 386(2): 136-42. PMID: 11368335, PII: S0003-9861(00)92175-1, DOI: 10.1006/abbi.2000.2175, ISSN: 0003-9861.

Shappell SB, Gupta RA, Manning S, Whitehead R, Boeglin WE, Schneider C, Case T, Price J, Jack GS, Wheeler TM, Matusik RJ, Brash AR, Dubois RN. 15S-Hydroxyeicosatetraenoic acid activates peroxisome proliferator-activated receptor gamma and inhibits proliferation in PC3 prostate carcinoma cells. Cancer Res. 2001 Jan 1/15/2001; 61(2): 497-503. PMID: 11212240, ISSN: 0008-5472.

Schneider C, Boeglin WE, Brash AR. Enantiomeric separation of hydroxy eicosanoids by chiral column chromatography: effect of the alcohol modifier. Anal. Biochem. 2000 Dec 12/1/2000; 287(1): 186-9. PMID: 11078601, PII: S0003-2697(00)94847-4, DOI: 10.1006/abio.2000.4847, ISSN: 0003-2697.

Brash AR. Autoxidation of methyl linoleate: identification of the bis-allylic 11-hydroperoxide. Lipids. 2000 Sep; 35(9): 947-52. PMID: 11026614, ISSN: 0024-4201.

Jack GS, Brash AR, Olson SJ, Manning S, Coffey CS, Smith JA, Shappell SB. Reduced 15-lipoxygenase-2 immunostaining in prostate adenocarcinoma: correlation with grade and expression in high-grade prostatic intraepithelial neoplasia. Hum. Pathol. 2000 Sep; 31(9): 1146-54. PMID: 11014584, PII: S0046-8177(00)60368-4, DOI: 10.1053/hupa.2000.16670, ISSN: 0046-8177.

Schneider C, Boeglin WE, Lai S, Cha JK, Brash AR. Synthesis and applications of stereospecifically (3)H-labeled arachidonic acids as mechanistic probes for lipoxygenase and cyclooxygenase catalysis. Anal. Biochem. 2000 Aug 8/15/2000; 284(1): 125-35. PMID: 10933865, PII: S0003269700946700, DOI: 10.1006/abio.2000.4670, ISSN: 0003-2697.

Muga SJ, Thuillier P, Pavone A, Rundhaug JE, Boeglin WE, Jisaka M, Brash AR, Fischer SM. 8S-lipoxygenase products activate peroxisome proliferator-activated receptor alpha and induce differentiation in murine keratinocytes. Cell Growth Differ. 2000 Aug; 11(8): 447-54. PMID: 10965849, ISSN: 1044-9523.

Tijet N, Wäspi U, Gaskin DJ, Hunziker P, Muller BL, Vulfson EN, Slusarenko A, Brash AR, Whitehead IM. Purification, molecular cloning, and expression of the gene encoding fatty acid 13-hydroperoxide lyase from guava fruit (Psidium guajava). Lipids. 2000 Jul; 35(7): 709-20. PMID: 10941871, ISSN: 0024-4201.

Schneider C, Brash AR. Stereospecificity of hydrogen abstraction in the conversion of arachidonic acid to 15R-HETE by aspirin-treated cyclooxygenase-2. Implications for the alignment of substrate in the active site. J. Biol. Chem. 2000 Feb 2/18/2000; 275(7): 4743-6. PMID: 10671506, ISSN: 0021-9258.

Jisaka M, Kim RB, Boeglin WE, Brash AR. Identification of amino acid determinants of the positional specificity of mouse 8S-lipoxygenase and human 15S-lipoxygenase-2. J. Biol. Chem. 2000 Jan 1/14/2000; 275(2): 1287-93. PMID: 10625675, ISSN: 0021-9258.

Boutaud O, Brash AR. Purification and catalytic activities of the two domains of the allene oxide synthase-lipoxygenase fusion protein of the coral Plexaura homomalla. J. Biol. Chem. 1999 Nov 11/19/1999; 274(47): 33764-70. PMID: 10559269, ISSN: 0021-9258.

Brash AR. Lipoxygenases: occurrence, functions, catalysis, and acquisition of substrate. J. Biol. Chem. 1999 Aug 8/20/1999; 274(34): 23679-82. PMID: 10446122, ISSN: 0021-9258.

Shappell SB, Boeglin WE, Olson SJ, Kasper S, Brash AR. 15-lipoxygenase-2 (15-LOX-2) is expressed in benign prostatic epithelium and reduced in prostate adenocarcinoma. Am. J. Pathol. 1999 Jul; 155(1): 235-45. PMID: 10393855, PMCID: PMC1866677, PII: S0002-9440(10)65117-6, DOI: 10.1016/S0002-9440(10)65117-6, ISSN: 0002-9440.

Varvas K, Järving I, Koljak R, Valmsen K, Brash AR, Samel N. Evidence of a cyclooxygenase-related prostaglandin synthesis in coral. The allene oxide pathway is not involved in prostaglandin biosynthesis. J. Biol. Chem. 1999 Apr 4/9/1999; 274(15): 9923-9. PMID: 10187766, ISSN: 0021-9258.

Brash AR, Jisaka M, Boeglin WE, Chang MS, Keeney DS, Nanney LB, Kasper S, Matusik RJ, Olson SJ, Shappell SB. Investigation of a second 15S-lipoxygenase in humans and its expression in epithelial tissues. Adv. Exp. Med. Biol. 1999; 469: 83-9. PMID: 10667314, ISSN: 0065-2598.

Brash AR, Jisaka M, Boeglin WE, Chang MS. Molecular cloning of a second human 15S-lipoxygenase and its murine homologue, an 8S-lipoxygenase. Their relationship to other mammalian lipoxygenases. Adv. Exp. Med. Biol. 1999; 447: 29-36. PMID: 10086180, ISSN: 0065-2598.

Boeglin WE, Kim RB, Brash AR. A 12R-lipoxygenase in human skin: mechanistic evidence, molecular cloning, and expression. Proc. Natl. Acad. Sci. U.S.A. 1998 Jun 6/9/1998; 95(12): 6744-9. PMID: 9618483, PMCID: PMC22619, ISSN: 0027-8424.

Jisaka M, Kim RB, Boeglin WE, Nanney LB, Brash AR. Molecular cloning and functional expression of a phorbol ester-inducible 8S-lipoxygenase from mouse skin. J. Biol. Chem. 1997 Sep 9/26/1997; 272(39): 24410-6. PMID: 9305900, ISSN: 0021-9258.

Koljak R, Boutaud O, Shieh BH, Samel N, Brash AR. Identification of a naturally occurring peroxidase-lipoxygenase fusion protein. Science. 1997 Sep 9/26/1997; 277(5334): 1994-6. PMID: 9302294, ISSN: 0036-8075.

Brash AR, Boeglin WE, Chang MS. Discovery of a second 15S-lipoxygenase in humans. Proc. Natl. Acad. Sci. U.S.A. 1997 Jun 6/10/1997; 94(12): 6148-52. PMID: 9177185, PMCID: PMC21017, ISSN: 0027-8424.

Hada T, Swift LL, Brash AR. Discovery of 5R-lipoxygenase activity in oocytes of the surf clam, Spisula solidissima. Biochim. Biophys. Acta. 1997 Jun 6/2/1997; 1346(2): 109-19. PMID: 9219894, PII: S0005-2760(96)00179-8, ISSN: 0006-3002.

Yamamoto S, Takahashi Y, Hada T, Hagiya H, Suzuki H, Reddy GR, Ueda N, Arakawa T, Nakamura M, Matsuda S, Taketani Y, Yoshimoto T, Azekawa T, Morita Y, Ishimura K, Arase S, Glasgow WC, Brash AR, Anton M, Kühn H. Mammalian arachidonate 12-lipoxygenases. Adv. Exp. Med. Biol. 1997; 400A: 127-31. PMID: 9547547, ISSN: 0065-2598.

Funk CD, Keeney DS, Oliw EH, Boeglin WE, Brash AR. Functional expression and cellular localization of a mouse epidermal lipoxygenase. J. Biol. Chem. 1996 Sep 9/20/1996; 271(38): 23338-44. PMID: 8798535, ISSN: 0021-9258.

Brash AR, Boeglin WE, Chang MS, Shieh BH. Purification and molecular cloning of an 8R-lipoxygenase from the coral Plexaura homomalla reveal the related primary structures of R- and S-lipoxygenases. J. Biol. Chem. 1996 Aug 8/23/1996; 271(34): 20949-57. PMID: 8702854, ISSN: 0021-9258.

Legrand AB, Wang J, Sobo G, Blair IA, Brash AR, Oates JA. Incorporation of 12(S)-hydroxyeicosatetraenoic acid into the phosphatidylcholine signaling pathway. Biochim. Biophys. Acta. 1996 May 5/31/1996; 1301(1-2): 150-60. PMID: 8652650, ISSN: 0006-3002.

Chang MS, Boeglin WE, Guengerich FP, Brash AR. Cytochrome P450-dependent transformations of 15R- and 15S-hydroperoxyeicosatetraenoic acids: stereoselective formation of epoxy alcohol products. Biochemistry. 1996 Jan 1/16/1996; 35(2): 464-71. PMID: 8555216, PII: bi952081v, DOI: 10.1021/bi952081v, ISSN: 0006-2960.

Brash AR, Song W. Detection, assay, and isolation of allene oxide synthase. Meth. Enzymol. 1996; 272: 250-9. PMID: 8791784, PII: S0076-6879(96)72030-X, ISSN: 0076-6879.

Brash AR, Song WC. Structure-function features of flaxseed allene oxide synthase. J Lipid Mediat Cell Signal. 1995 Oct; 12(2-3): 275-82. PMID: 8777571, ISSN: 0929-7855.

Brash AR, Boeglin WE, Capdevila JH, Yeola S, Blair IA. 7-HETE, 10-HETE, and 13-HETE are major products of NADPH-dependent arachidonic acid metabolism in rat liver microsomes: analysis of their stereochemistry, and the stereochemistry of their acid-catalyzed rearrangement. Arch. Biochem. Biophys. 1995 Aug 8/20/1995; 321(2): 485-92. PMID: 7646075, PII: S0003-9861(85)71421-X, DOI: 10.1006/abbi.1995.1421, ISSN: 0003-9861.

Brash AR, Chang MS, Funk CD, Song W. Novel transformations of HPETEs by cytochrome P450s. Ann. N. Y. Acad. Sci. 1994 Nov 11/15/1994; 744: 25-30. PMID: 7825847, ISSN: 0077-8923.

Takahashi Y, Glasgow WC, Suzuki H, Taketani Y, Yamamoto S, Anton M, Kühn H, Brash AR. Investigation of the oxygenation of phospholipids by the porcine leukocyte and human platelet arachidonate 12-lipoxygenases. Eur. J. Biochem. 1993 Nov 11/15/1993; 218(1): 165-71. PMID: 8243462, ISSN: 0014-2956.

Song WC, Funk CD, Brash AR. 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. 1993 Sep 9/15/1993; 90(18): 8519-23. PMID: 8378325, PMCID: PMC47388, ISSN: 0027-8424.

Chen XS, Brash AR, Funk CD. Purification and characterization of recombinant histidine-tagged human platelet 12-lipoxygenase expressed in a baculovirus/insect cell system. Eur. J. Biochem. 1993 Jun 6/15/1993; 214(3): 845-52. PMID: 8319693, ISSN: 0014-2956.

Song WC, Baertschi SW, Boeglin WE, Harris TM, Brash AR. Formation of epoxyalcohols by a purified allene oxide synthase. Implications for the mechanism of allene oxide synthesis. J. Biol. Chem. 1993 Mar 3/25/1993; 268(9): 6293-8. PMID: 8454602, ISSN: 0021-9258.

Brash AR, Hughes MA, Hawkins DJ, Boeglin WE, Song WC, Meijer L. Allene oxide and aldehyde biosynthesis in starfish oocytes. J. Biol. Chem. 1991 Dec 12/5/1991; 266(34): 22926-31. PMID: 1744085, ISSN: 0021-9258.

Song WC, Brash AR. Investigation of the allene oxide pathway in the coral Plexaura homomalla: formation of novel ketols and isomers of prostaglandin A2 from 15-hydroxyeicosatetraenoic acid. Arch. Biochem. Biophys. 1991 Nov 11/1/1991; 290(2): 427-35. PMID: 1681785, ISSN: 0003-9861.

Song WC, Brash AR. Purification of an allene oxide synthase and identification of the enzyme as a cytochrome P-450. Science. 1991 Aug 8/16/1991; 253(5021): 781-4. PMID: 1876834, ISSN: 0036-8075.

Hughes MA, Brash AR. Investigation of the mechanism of biosynthesis of 8-hydroxyeicosatetraenoic acid in mouse skin. Biochim. Biophys. Acta. 1991 Feb 2/5/1991; 1081(3): 347-54. PMID: 1900207, PII: 0005-2760(91)90292-P, ISSN: 0006-3002.

Kuhn H, Belkner J, Wiesner R, Brash AR. Oxygenation of biological membranes by the pure reticulocyte lipoxygenase. J. Biol. Chem. 1990 Oct 10/25/1990; 265(30): 18351-61. PMID: 2120232, ISSN: 0021-9258.

Kühn H, Sprecher H, Brash AR. On singular or dual positional specificity of lipoxygenases. The number of chiral products varies with alignment of methylene groups at the active site of the enzyme. J. Biol. Chem. 1990 Sep 9/25/1990; 265(27): 16300-5. PMID: 2118902, ISSN: 0021-9258.

Brash AR, Baertschi SW, Harris TM. Formation of prostaglandin A analogues via an allene oxide. J. Biol. Chem. 1990 Apr 4/25/1990; 265(12): 6705-12. PMID: 2324098, ISSN: 0021-9258.

Kühn H, Brash AR. Occurrence of lipoxygenase products in membranes of rabbit reticulocytes. Evidence for a role of the reticulocyte lipoxygenase in the maturation of red cells. J. Biol. Chem. 1990 Jan 1/25/1990; 265(3): 1454-8. PMID: 2104842, ISSN: 0021-9258.

Brash AR, Hawkins DJ. High-performance liquid chromatography for chiral analysis of eicosanoids. Meth. Enzymol. 1990; 187: 187-95. PMID: 2233345, PII: 0076-6879(90)87024-W, ISSN: 0076-6879.

Brash AR, Yokoyama C, Oates JA, Yamamoto S. Mechanistic studies of the dioxygenase and leukotriene synthase activities of the porcine leukocyte 12S-lipoxygenase. Arch. Biochem. Biophys. 1989 Sep; 273(2): 414-22. PMID: 2774560, ISSN: 0003-9861.

Hawkins DJ, Brash AR. Mechanism of biosynthesis of 11R-and 12R-hydroxyeicosatetraenoic acids by eggs of the sea urchin Strongylocentrotus purpuratus. FEBS Lett. 1989 Apr 4/10/1989; 247(1): 9-12. PMID: 2495992, PII: 0014-5793(89)81228-1, ISSN: 0014-5793.

Hawkins DJ, Brash AR. Lipoxygenase metabolism of polyunsaturated fatty acids in oocytes of the frog Xenopus laevis. Arch. Biochem. Biophys. 1989 Feb 2/1/1989; 268(2): 447-55. PMID: 2492416, ISSN: 0003-9861.

Brash AR, Baertschi SW, Ingram CD, Harris TM. Allene oxides as intermediates in biosynthesis of ketols and cyclopentenones. Adv. Prostaglandin Thromboxane Leukot. Res. 1989; 19: 70-3. PMID: 2526564, ISSN: 0732-8141.

Hawkins DJ, Kühn H, Petty EH, Brash AR. Resolution of enantiomers of hydroxyeicosatetraenoate derivatives by chiral phase high-pressure liquid chromatography. Anal. Biochem. 1988 Sep; 173(2): 456-62. PMID: 3189822, ISSN: 0003-2697.

Murray JJ, Brash AR. Rabbit reticulocyte lipoxygenase catalyzes specific 12(S) and 15(S) oxygenation of arachidonoyl-phosphatidylcholine. Arch. Biochem. Biophys. 1988 Sep; 265(2): 514-23. PMID: 3138949, ISSN: 0003-9861.

Brash AR, Baertschi SW, Ingram CD, Harris TM. Isolation and characterization of natural allene oxides: unstable intermediates in the metabolism of lipid hydroperoxides. Proc. Natl. Acad. Sci. U.S.A. 1988 May; 85(10): 3382-6. PMID: 2835769, PMCID: PMC280213, ISSN: 0027-8424.

Ingram CD, Brash AR. Characterization of HETEs and related conjugated dienes by UV spectroscopy. Lipids. 1988 Apr; 23(4): 340-4. PMID: 3398721, ISSN: 0024-4201.

Baertschi SW, Ingram CD, Harris TM, Brash AR. Absolute configuration of cis-12-oxophytodienoic acid of flaxseed: implications for the mechanism of biosynthesis from the 13(S)-hydroperoxide of linolenic acid. Biochemistry. 1988 Jan 1/12/1988; 27(1): 18-24. PMID: 3349025, ISSN: 0006-2960.

Kühn H, Brash AR, Wiesner R, Alder L. Lipoxygenase catalyzed oxygenation of hydroxy fatty acids to lipoxins. Adv. Exp. Med. Biol. 1988; 229: 39-49. PMID: 3138902, ISSN: 0065-2598.

Yamamoto S, Ueda N, Yokoyama C, Fitzsimmons BJ, Rokach J, Oates JA, Brash AR. Lipoxin syntheses by arachidonate 12- and 5-lipoxygenases purified from porcine leukocytes. Adv. Exp. Med. Biol. 1988; 229: 15-26. PMID: 3421157, ISSN: 0065-2598.

Kühn H, Schewe T, Rapoport SM, Brash AR. Enzymatic lipid peroxidation: a step in the breakdown of mitochondria during the maturation of red blood cells. Basic Life Sci. 1988; 49: 945-9. PMID: 3150671, ISSN: 0090-5542.

Ueda N, Yokoyama C, Yamamoto S, Fitzsimmons BJ, Rokach J, Oates JA, Brash AR. Lipoxin synthesis by arachidonate 12-lipoxygenase purified from porcine leukocytes. Biochem. Biophys. Res. Commun. 1987 Dec 12/31/1987; 149(3): 1063-9. PMID: 3122743, PII: 0006-291X(87)90516-X, ISSN: 0006-291X.

Kühn H, Wiesner R, Alder L, Fitzsimmons BJ, Rokach J, Brash AR. Formation of lipoxin B by the pure reticulocyte lipoxygenase via sequential oxygenation of the substrate. Eur. J. Biochem. 1987 Dec 12/15/1987; 169(3): 593-601. PMID: 3121318, ISSN: 0014-2956.

Brash AR, Baertschi SW, Ingram CD, Harris TM. 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 a Racemic prostanoid. J. Biol. Chem. 1987 Nov 11/25/1987; 262(33): 15829-39. PMID: 2824470, ISSN: 0021-9258.

Brash AR, Ingram CD, Harris TM. Analysis of a specific oxygenation reaction of soybean lipoxygenase-1 with fatty acids esterified in phospholipids. Biochemistry. 1987 Aug 8/25/1987; 26(17): 5465-71. PMID: 3118947, ISSN: 0006-2960.

Hawkins DJ, Brash AR. Eggs of the sea urchin, Strongylocentrotus purpuratus, contain a prominent (11R) and (12R) lipoxygenase activity. J. Biol. Chem. 1987 Jun 6/5/1987; 262(16): 7629-34. PMID: 3108255, ISSN: 0021-9258.

Brash AR, Oates JA, Yokoyama C, Yamamoto S. Mechanism of transformation of 15(S)-hydroperoxyeicosatetraenoic acid to 15-series leukotrienes by purified porcine leukocyte 12-lipoxygenase. Adv. Prostaglandin Thromboxane Leukot. Res. 1987; 17A: 75-7. PMID: 2821770, ISSN: 0732-8141.

Glasgow WC, Brash AR. Specific short-chain aldehydes are cleavage products of the transformation of arachidonic acid to hydroperoxyeicosatetraenoic acids and leukotrienes. Adv. Prostaglandin Thromboxane Leukot. Res. 1987; 17A: 105-8. PMID: 2821748, ISSN: 0732-8141.

Yamamoto S, Ueda N, Yokoyama C, Kaneko S, Shinjo F, Yoshimoto T, Oates JA, Brash AR, Fitzsimmons BJ, Rokach J. Dioxygenase and leukotriene A synthase activities of arachidonate 5- and 12-lipoxygenases purified from porcine leukocytes. Adv. Prostaglandin Thromboxane Leukot. Res. 1987; 17A: 55-9. PMID: 2959113, ISSN: 0732-8141.

Meijer L, Brash AR, Bryant RW, Ng K, Maclouf J, Sprecher H. Stereospecific induction of starfish oocyte maturation by (8R)-hydroxyeicosatetraenoic acid. J. Biol. Chem. 1986 Dec 12/25/1986; 261(36): 17040-7. PMID: 3097019, ISSN: 0021-9258.

Yokoyama C, Shinjo F, Yoshimoto T, Yamamoto S, Oates JA, Brash AR. Arachidonate 12-lipoxygenase purified from porcine leukocytes by immunoaffinity chromatography and its reactivity with hydroperoxyeicosatetraenoic acids. J. Biol. Chem. 1986 Dec 12/15/1986; 261(35): 16714-21. PMID: 3782139, ISSN: 0021-9258.

Murray JJ, Tonnel AB, Brash AR, Roberts LJ, Gosset P, Workman R, Capron A, Oates JA. Release of prostaglandin D2 into human airways during acute antigen challenge. N. Engl. J. Med. 1986 Sep 9/25/1986; 315(13): 800-4. PMID: 3462506, DOI: 10.1056/NEJM198609253151304, ISSN: 0028-4793.

Watson ML, Workman RJ, Herzer W, Branch RA, Oates JA, Brash AR. Systemic synthesis of prostaglandin I2 following sustained infusion of angiotensin II in conscious dogs. Eur. J. Pharmacol. 1986 Aug 8/7/1986; 127(1-2): 9-16. PMID: 3530786, ISSN: 0014-2999.

Brash AR, Ingram CD. Lipoxygenase metabolism of endogenous and exogenous arachidonate in leukocytes: GC-MS analyses of incubations in H2(18)O buffers. Prostaglandins Leukot Med. 1986 Aug; 23(2-3): 149-54. PMID: 3094028, ISSN: 0262-1746.

Ueda N, Yamamoto S, Oates JA, Brash AR. Stereoselective hydrogen abstraction in leukotriene A4 synthesis by purified 5-lipoxygenase of porcine leukocytes. Prostaglandins. 1986 Jul; 32(1): 43-8. PMID: 3020619, ISSN: 0090-6980.

Gerzer R, Brash AR, Hardman JG. Activation of soluble guanylate cyclase by arachidonic acid and 15-lipoxygenase products. Biochim. Biophys. Acta. 1986 May 5/29/1986; 886(3): 383-9. PMID: 2871867, ISSN: 0006-3002.

Brash AR, Ingram CD, Maas RL. A secondary isotope effect in the lipoxygenase reaction. Biochim. Biophys. Acta. 1986 Feb 2/12/1986; 875(2): 256-61. PMID: 3080027, PII: 0005-2760(86)90175-X, ISSN: 0006-3002.

Glasgow WC, Harris TM, Brash AR. A short-chain aldehyde is a major lipoxygenase product in arachidonic acid-stimulated porcine leukocytes. J. Biol. Chem. 1986 Jan 1/5/1986; 261(1): 200-4. PMID: 3079754, ISSN: 0021-9258.

Beckman JK, Gay JC, Brash AR, Lukens JN, Oates JA. Investigations of the biological activity of leukotriene A4 in human polymorphonuclear leukocytes. Biochem. Biophys. Res. Commun. 1985 Nov 11/27/1985; 133(1): 23-9. PMID: 3000375, PII: 0006-291X(85)91836-4, ISSN: 0006-291X.

Lawson JA, Brash AR, Doran J, FitzGerald GA. Measurement of urinary 2,3-dinor-thromboxane B2 and thromboxane B2 using bonded-phase phenylboronic acid columns and capillary gas chromatography--negative-ion chemical ionization mass spectrometry. Anal. Biochem. 1985 Nov 11/1/1985; 150(2): 463-70. PMID: 4091270, ISSN: 0003-2697.

Brash AR. A review of possible roles of the platelet 12-lipoxygenase. Circulation. 1985 Oct; 72(4): 702-7. PMID: 4028374, ISSN: 0009-7322.

Beckman JK, Gay JC, Brash AR, Lukens JN, Oates JA. Differential effects of lipoxygenase products on FMLP and LTB4 evoked neutrophil aggregation. Lipids. 1985 Jun; 20(6): 357-60. PMID: 2991693, ISSN: 0024-4201.

Beckman JK, Gay JC, Brash AR, Lukens JN, Oates JA. Stimulation by lipoxygenase products of superoxide anion production in FMLP-treated neutrophils. Lipids. 1985 May; 20(5): 318-21. PMID: 2989652, ISSN: 0024-4201.

Maas RL, Ingram CD, Porter AT, Oates JA, Taber DF, Brash AR. Investigation of the chemical conversion of hydroperoxyeicosatetraenoate to leukotriene epoxide using stereospecifically labeled arachidonic acid. Comparison with the enzymatic reaction. J. Biol. Chem. 1985 Apr 4/10/1985; 260(7): 4217-28. PMID: 2984197, ISSN: 0021-9258.

Brash AR, Porter AT, Maas RL. Investigation of the selectivity of hydrogen abstraction in the nonenzymatic formation of hydroxyeicosatetraenoic acids and leukotrienes by autoxidation. J. Biol. Chem. 1985 Apr 4/10/1985; 260(7): 4210-6. PMID: 2984196, ISSN: 0021-9258.

Brash AR, Murray JJ, Oates JA. The 5-lipoxygenase and 15-lipoxygenase of neutrophils and eosinophils. Prog. Clin. Biol. Res. 1985; 199: 143-52. PMID: 3934680, ISSN: 0361-7742.

Murray JJ, Tonnel AB, Brash AR, Roberts LJ, Gosset P, Workman R, Capron A, Oates JA. Prostaglandin D2 is released during acute allergic bronchospasm in man. Trans. Assoc. Am. Physicians. 1985; 98: 275-80. PMID: 3870298, ISSN: 0066-9458.

Blair IA, Brash AR, Daugherty J, FitzGerald GA. Quantitative analysis of leukotriene B4 in human serum. Adv. Prostaglandin Thromboxane Leukot. Res. 1985; 15: 61-5. PMID: 3004150, ISSN: 0732-8141.

FitzGerald GA, Lawson J, Blair IA, Brash AR. Analysis of urinary metabolites of thromboxane and prostacyclin by negative-ion chemical-ionization gas chromatography/mass spectrometry. Adv. Prostaglandin Thromboxane Leukot. Res. 1985; 15: 87-90. PMID: 2936207, ISSN: 0732-8141.

Brash AR. Specific lipoxygenase attack on arachidonate and linoleate esterified in phosphatidylcholine: precedent for an alternative mechanism in activation of icosanoid biosynthesis. Adv. Prostaglandin Thromboxane Leukot. Res. 1985; 15: 197-9. PMID: 2936092, ISSN: 0732-8141.

Gay JC, Beckman JK, Brash AR, Oates JA, Lukens JN. Enhancement of chemotactic factor-stimulated neutrophil oxidative metabolism by leukotriene B4. Blood. 1984 Oct; 64(4): 780-5. PMID: 6089934, ISSN: 0006-4971.

Brash AR, Maas RL, Oates JA. On the mechanism of biosynthesis of 5- and 15-series leukotrienes. J. Allergy Clin. Immunol. 1984 Sep; 74(3 Pt 2): 316-23. PMID: 6088609, ISSN: 0091-6749.

Schneider HA, Yonker RA, Longley S, Katz P, Mathias J, Panush RS. Scleroderma esophagus: a nonspecific entity. Ann. Intern. Med. 1984 Jun; 100(6): 848-50. PMID: 6609658, ISSN: 0003-4819.

FitzGerald GA, Smith B, Pedersen AK, Brash AR. Increased prostacyclin biosynthesis in patients with severe atherosclerosis and platelet activation. N. Engl. J. Med. 1984 Apr 4/26/1984; 310(17): 1065-8. PMID: 6231483, DOI: 10.1056/NEJM198404263101701, ISSN: 0028-4793.

Hoffman LH, Davenport GR, Brash AR. Endometrial prostaglandins and phospholipase activity related to implantation in rabbits: effects of dexamethasone. Biol. Reprod. 1984 Apr; 30(3): 544-55. PMID: 6586207, ISSN: 0006-3363.

Watson ML, Goodman RP, Gill JR, Branch RA, Brash AR, Fitzgerald GA. Endogenous prostacyclin synthesis is decreased during activation of the renin-angiotensin system in man. J. Clin. Endocrinol. Metab. 1984 Feb; 58(2): 304-8. PMID: 6363436, DOI: 10.1210/jcem-58-2-304, ISSN: 0021-972X.

FitzGerald GA, Brash AR, Oates JA, Pedersen AK. Endogenous prostacyclin biosynthesis and platelet function during selective inhibition of thromboxane synthase in man. J. Clin. Invest. 1983 Oct; 72(4): 1336-43. PMID: 6355181, PMCID: PMC370417, DOI: 10.1172/JCI111089, ISSN: 0021-9738.

Watson ML, Gill JR, Branch RA, Oates JA, Brash AR. Systemic prostaglandin I2 synthesis is normal in patients with Bartter's syndrome. Lancet. 1983 Aug 8/13/1983; 2(8346): 368-70. PMID: 6135873, PII: S0140-6736(83)90344-6, ISSN: 0140-6736.

Brash AR, Jackson EK, Saggese CA, Lawson JA, Oates JA, FitzGerald GA. Metabolic disposition of prostacyclin in humans. J. Pharmacol. Exp. Ther. 1983 Jul; 226(1): 78-87. PMID: 6345756, ISSN: 0022-3565.

Maas RL, Brash AR. Evidence for a lipoxygenase mechanism in the biosynthesis of epoxide and dihydroxy leukotrienes from 15(S)-hydroperoxyicosatetraenoic acid by human platelets and porcine leukocytes. Proc. Natl. Acad. Sci. U.S.A. 1983 May; 80(10): 2884-8. PMID: 6304687, PMCID: PMC393937, ISSN: 0027-8424.

FitzGerald GA, Oates JA, Hawiger J, Maas RL, Roberts LJ, Lawson JA, Brash AR. Endogenous biosynthesis of prostacyclin and thromboxane and platelet function during chronic administration of aspirin in man. J. Clin. Invest. 1983 Mar; 71(3): 676-88. PMID: 6338043, PMCID: PMC436917, ISSN: 0021-9738.

Turk J, Rand TH, Maas RL, Lawson JA, Brash AR, Roberts LJ, Colley DG, Oates JA. Identification of lipoxygenase products from arachidonic acid metabolism in stimulated murine eosinophils. Biochim. Biophys. Acta. 1983 Jan 1/7/1983; 750(1): 78-90. PMID: 6402030, PII: 0005-2760(83)90206-0, ISSN: 0006-3002.

Maas RL, Lawson JA, Brash AR, Oates JA. Derivatization and analysis of leukotrienes by desorption-chemical ionization mass spectrometry at subnanomole level. Adv. Prostaglandin Thromboxane Leukot. Res. 1983; 11: 229-34. PMID: 6303070, ISSN: 0732-8141.

FitzGerald GA, Maas RL, Lawson JA, Oates JA, Roberts LJ, Brash AR. Aspirin inhibits endogenous prostacyclin and thromboxane biosynthesis in man. Adv. Prostaglandin Thromboxane Leukot. Res. 1983; 11: 265-6. PMID: 6221534, ISSN: 0732-8141.

Turk J, Maas RL, Roberts LJ, Brash AR, Oates JA. Conjugated triene metabolites of arachidonic acid derived from dioxygenation at carbon-15: origin from eosinophil and mechanisms of biosynthesis. Adv. Prostaglandin Thromboxane Leukot. Res. 1983; 11: 123-32. PMID: 6221514, ISSN: 0732-8141.

Brash AR, Jackson EK, Lawson JA, Branch RA, Oates JA, FitzGerald GA. Quantitative aspects of prostacyclin metabolism in humans. Adv. Prostaglandin Thromboxane Leukot. Res. 1983; 11: 119-22. PMID: 6221513, ISSN: 0732-8141.

Maas RL, Ingram CD, Taber DF, Oates JA, Brash AR. Stereospecific removal of the DR hydrogen atom at the 10-carbon of arachidonic acid in the biosynthesis of leukotriene A4 by human leukocytes. J. Biol. Chem. 1982 Nov 11/25/1982; 257(22): 13515-9. PMID: 6292193, ISSN: 0021-9258.

Jackson EK, Gerkens JF, Brash AR, Branch RA. Acute renal artery constriction increases renal prostaglandin I2 biosynthesis and renin release in the conscious dog. J. Pharmacol. Exp. Ther. 1982 Aug; 222(2): 410-3. PMID: 7047717, ISSN: 0022-3565.

Turk J, Maas RL, Brash AR, Roberts LJ, Oates JA. Arachidonic acid 15-lipoxygenase products from human eosinophils. J. Biol. Chem. 1982 Jun 6/25/1982; 257(12): 7068-76. PMID: 6806264, ISSN: 0021-9258.

Maas RL, Turk J, Oates JA, Brash AR. Formation of a novel dihydroxy acid from arachidonic acid by lipoxygenase-catalyzed double oxygenation in rat mononuclear cells and human leukocytes. J. Biol. Chem. 1982 Jun 6/25/1982; 257(12): 7056-67. PMID: 6806263, ISSN: 0021-9258.

Goodman RP, Killam AP, Brash AR, Branch RA. Prostacyclin production during pregnancy: comparison of production during normal pregnancy and pregnancy complicated by hypertension. Am. J. Obstet. Gynecol. 1982 Apr 4/1/1982; 142(7): 817-22. PMID: 7039321, ISSN: 0002-9378.

Brash AR. Quantitation of the major urinary metabolite of PGF2 alpha in the human by GC-MS. Meth. Enzymol. 1982; 86: 579-85. PMID: 6957704, ISSN: 0076-6879.

Falardeau P, Brash AR. Quantitation of two dinor metabolites of prostacyclin by GC-MS. Meth. Enzymol. 1982; 86: 585-92. PMID: 6752645, ISSN: 0076-6879.

Maas RL, Brash AR, Oates JA. Novel leukotrienes and lipoxygenase products from arachidonic acid. Adv. Prostaglandin Thromboxane Leukot. Res. 1982; 9: 29-44. PMID: 6283848, ISSN: 0732-8141.

Roberts LJ, Brash AR, Oates JA. Metabolic fate of thromboxane A2 and prostacyclin. Adv. Prostaglandin Thromboxane Leukot. Res. 1982; 10: 211-25. PMID: 6216783, ISSN: 0732-8141.

FitzGerald GA, Brash AR, Falardeau P, Oates JA. Estimated rate of prostacyclin secretion into the circulation of normal man. J. Clin. Invest. 1981 Nov; 68(5): 1272-6. PMID: 7028786, PMCID: PMC370922, ISSN: 0021-9738.

Oliw EH, Lawson JA, Brash AR, Oates JA. Arachidonic acid metabolism in rabbit renal cortex. Formation of two novel dihydroxyeicosatrienoic acids. J. Biol. Chem. 1981 Oct 10/10/1981; 256(19): 9924-31. PMID: 6792198, ISSN: 0021-9258.

Maas RL, Brash AR, Oates JA. A second pathway of leukotriene biosynthesis in porcine leukocytes. Proc. Natl. Acad. Sci. U.S.A. 1981 Sep; 78(9): 5523-27. PMID: 6272308, PMCID: PMC348778, ISSN: 0027-8424.

Falardeau P, Oates JA, Brash AR. Quantitative analysis of two dinor urinary metabolites of prostaglandin I2. Anal. Biochem. 1981 Aug; 115(2): 359-67. PMID: 7030131, ISSN: 0003-2697.

Brash AR, Hickey DE, Graham TP, Stahlman MT, Oates JA, Cotton RB. Pharmacokinetics of indomethacin in the neonate. Relation of plasma indomethacin levels to response of the ductus arteriosus. N. Engl. J. Med. 1981 Jul 7/9/1981; 305(2): 67-72. PMID: 7242577, DOI: 10.1056/NEJM198107093050203, ISSN: 0028-4793.

Goodman RP, Brash AR. Measurement of 5,8,11, 14-icosatetraynoic acid in plasma by gas-liquid chromatography. J. Lipid Res. 1981 Mar; 22(3): 541-3. PMID: 7240980, ISSN: 0022-2275.

Gould SR, Brash AR, Conolly ME, Lennard-Jones JE. Studies of prostaglandins and sulphasalazine in ulcerative colitis. Prostaglandins Med. 1981 Feb; 6(2): 165-82. PMID: 6113614, ISSN: 0161-4630.

Hubbard WC, Hough AJ, Brash AR, Watson JT, Oates JA. Metabolism of linoleic and arachidonic acids in VX2 carcinoma tissue: identification of monohydroxy octadecadienoic acids and monohydroxy eicosatetraenoic acids. Prostaglandins. 1980 Sep; 20(3): 431-47. PMID: 6775354, ISSN: 0090-6980.

Boeynaems JM, Brash AR, Oates JA, Hubbard WC. Preparation and assay of monohydroxy-eicosatetraenoic acids. Anal. Biochem. 1980 May 5/15/1980; 104(2): 259-67. PMID: 7004263, ISSN: 0003-2697.

Goetzl EJ, Brash AR, Tauber AI, Oates JA, Hubbard WC. Modulation of human neutrophil function by monohydroxy-eicosatetraenoic acids. Immunology. 1980 Apr; 39(4): 491-501. PMID: 6247265, PMCID: PMC1458022, ISSN: 0019-2805.

Hubbard WC, Hough A, Brash AR, Johnson RM, Oates JA. The VX-2 carcinoma: humoral effects and arachidonic acid metabolism. Adv Prostaglandin Thromboxane Res. 1980; 6: 525-7. PMID: 7386286, ISSN: 0361-5952.

Brash AR, Baillie TA. The identification of 5beta,7alpha-dihydroxy-11-oxotetranor-prostane-1,16-dioic acid as a urinary metabolite of prostaglandin F2alpha in the rat. Biochim. Biophys. Acta. 1979 Feb 2/26/1979; 572(2): 371-5. PMID: 427184, ISSN: 0006-3002.

Brash AR, Conolly ME. The effect of indomethacin on the biosynthesis and metabolism of prostaglandin F2alpha in man. Prostaglandins. 1978 Jun; 15(6): 983-91. PMID: 693920, ISSN: 0090-6980.

Brash AR, Baillie TA. A comparison of t-butyldimethylsilyl and trimethylsilyl ether derivatives for the characterization of urinary metabolites of prostaglandin F2alpha by gas chromatography mass spectrometry. Biomed. Mass Spectrom. 1978 May; 5(5): 346-56. PMID: 656559, DOI: 10.1002/bms.1200050506, ISSN: 0306-042X.

Gould SR, Brash AR, Conolly ME. Increased prostaglandin production in ulcerative colitis [letter]. Lancet. 1977 Jul 7/9/1977; 2(8028): 98. PMID: 69189, ISSN: 0140-6736.

Brash AR, Baillie TA, Clare RA, Draffan GH. Quantitative determination of the major metabolite of prostaglandins F1alpha and F2alpha in human urine by stable isotope dilution and combined gas chromatography--mass spectrometry. Biochem Med. 1976 Aug; 16(1): 77-94. PMID: 1008871, ISSN: 0006-2944.

Brash AR, Draffan GH, Clare RA, Baillie TA. A new method for the determination of the major metabolite of prostaglandin F2alpha in human urine based on stable isotope dilution and gas chromatography-mass spectrometry. Biochem. Soc. Trans. 1976; 4(4): 706-8. PMID: 1001746, ISSN: 0300-5127.

Brash AR, Jones RL. Proceedings: Applications of liquid-gel partition chromatography in the prostaglandin field. Br. J. Pharmacol. 1974 Sep; 52(1): 145P. PMID: 4451795, PMCID: PMC1776952, ISSN: 0007-1188.

Brash AR, Jones RL. Straight phase separation of prostaglandin methyl esters on lipophilic gels. Prostaglandins. 1974 Mar 3/10/1974; 5(5): 441-54. PMID: 4822193, ISSN: 0090-6980.

Brash AR, Cuthbert AW. The effects of saponins on the transporting epithelium of isolated frog skin. Br. J. Pharmacol. 1970 Nov; 40(3): 544P. PMID: 5497807, PMCID: PMC1703105, ISSN: 0007-1188.

Available Postdoctoral Position Details
Dr Brash has immediate openings for postdoctoral fellows to study lipoxygenase structure/function and other mechanisms of oxygenation of polyunsaturated lipids. Recent publications exemplify the range of enzymological and mechanistic studies, and also work on the biological role of lipid oxygenases. For further information, applicants should submit electronically a C.V. & names of three references to: Alan R. Brash, PhD <A HREF="mailto:alan.brash@vanderbilt.edu">Email: alan.brash@mcmail.vanderbilt.edu </A HREF> Please include a short description of your own research and the reason for your interest in this opportunity.