By Patrick Y-K Wong, Charles N Serhan
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Extra resources for Lipoxins: Biosynthesis, Chemistry, and Biological Activities
The biological potency of S-series lipoxins were similar to those of 4-series. INTRODUCTION Lipoxins, the new series of biologically active derivative of arachidonic acid, were first isolated by Serhan and coworker 1 • 2 · 3 after incubating 15-hydroperoxyeicosatetraenoic acid (lS-HPETE) with human leukocytes. Their structures were elucidated as SS,6R,lSS-trihydroxy7,9,13-E,ll-Z-eicosatetraenoic acid or lipoxin A4 (LXA4 ) and SS,l4R,lSS,trihydorxy-6,10,12-E-8-Z-eicosatetraenoic acid or lipoxin B4 (LXB 4 ) as well as their structural isomers 4 • 5 .
Seyama, K. Tadokoro, 0. R~dmark, and B. Samuelsson, Characterization of leukotriene A4 synthase from murine mast cells: Evidence for its identity to arachidonate 5-lipoxygenase, Proc. Natl. Acad. Sci. USA 83:4175 (1986). 15. N. Ueda, S. J. Fitzsimmons, and J. Rokach, Lipoxin synthesis by arachidonate 5-lipoxygenase purified from porcine leukocytes, Biochern. Biophys. Res. Commun. 144:996 (1987). 16. Y-K. Wong, R. Hughes, and B. Lam, Lipoxene: A new group of trihydroxy pentaenes of eicosapentaenoic acid derived from porcine leukocytes, Biochem.
5S,14R,l5S(8Z)-LX B! Cl ~ I ~~------1 ' . I \ '\, time Fig. 2. 6 L 8 10 12 (min) RP-HPLC analysis of trihyaroxy tetraenes formed from various substrates by the reticulocyte lipoxygenase. A) 55,155-DiHETE methyl ester, B) 155-HPETE methyl ester, C) 14R,l5S-DiHETE methyl, D) 145,155-DiHETE methyl ester, E) 55/R-HETE methyl ester. 42 Lipoxin formation by the soybean lipoxygenase This enzyme converts 15S-HPETE methyl ester to trihydroxy tetraenes with a comparable rate (Table 2) and specificity (not shown) as the reticulocyte enzyme.