Serhan C N, Hamberg M, Samuelsson B, Morris J, Wishka D G
Proc Natl Acad Sci U S A. 1986 Apr;83(7):1983-7. doi: 10.1073/pnas.83.7.1983.
Lipoxin B (LXB) was prepared by incubation of (15S)-15-hydroperoxy-5,8,11-cis-13-trans-icosatetraenoic acid (15-HPETE) with human leukocytes. Comparison with a number of trihydroxyicosatetraenes prepared by total synthesis showed that biologically derived LXB is (5S,14R,15S)-5,14,15-trihydroxy-6,10,12-trans-8-cis-icosatetraenoi c acid. Two isomers of LXB were identified by using an improved isolation procedure. These compounds were shown to be (5S,14R,15S)-5,14,15-trihydroxy-6,8,10,12-trans-icosatetraenoic acid (8-trans-LXB) and (5S,14S,15S)-5,14,15-trihydroxy-6,8,10,12-trans-icosatetraenoic acid [(14S)-8-trans-LXB]. Experiments with 18O2 showed that formation of LXB and its two isomers occurred with incorporation of molecular oxygen at C-5 but not at C-14. These results together with the finding that (15S)-hydroxy-5,8,11-cis-13-trans-icosatetraenoic acid (15-HETE) is a precursor of LXB compounds in activated leukocytes suggest that 15-hydroxy-5,6-epoxy-7,9,13-trans-11-cis-icosatetraenoic acid or its equivalent is a common intermediate in the biosynthesis of LXB and its two isomers.
脂氧素B（LXB）是通过将（15S）-15-氢过氧-5,8,11-顺式-13-反式-二十碳四烯酸（15-HPETE）与人白细胞孵育制备而成。与通过全合成制备的多种三羟基二十碳四烯酸进行比较表明，生物来源的LXB是（5S,14R,15S）-5,14,15-三羟基-6,10,12-反式-8-顺式-二十碳四烯酸。通过使用改进的分离程序鉴定出了LXB的两种异构体。这些化合物被证明是（5S,14R,15S）-5,14,15-三羟基-6,8,10,12-反式-二十碳四烯酸（8-反式-LXB）和（5S,14S,15S）-5,14,15-三羟基-6,8,10,12-反式-二十碳四烯酸[（14S）-8-反式-LXB]。用18O2进行的实验表明，LXB及其两种异构体的形成伴随着分子氧在C-5位而非C-14位的掺入。这些结果以及（15S）-羟基-5,8,11-顺式-13-反式-二十碳四烯酸（15-HETE）是活化白细胞中LXB化合物前体的发现表明，15-羟基-5,6-环氧-7,9,13-反式-11-顺式-二十碳四烯酸或其等同物是LXB及其两种异构体生物合成中的常见中间体。
