On the stereochemistry and biosynthesis of lipoxin B.

Serhan, Charles N.; Hámberg, Mats; Samuelsson, Bengt; Morris, Joel; Wishka, Donn G.

doi:10.1073/pnas.83.7.1983

Cited by 104 publications

(77 citation statements)

References 18 publications

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“…The biosynthesis of lipoxin A and lipoxin B in other systems has been shown to involve the formation of an unstable allylic epoxide which rapidly undergoes hydrolysis to the trihydroxy-tetraene products [3,4]. This mechanism can be distinguished from direct oxygenation by experiments with heavy oxygen isotopes.…”

Section: Mechanism Of Biosynthesismentioning

confidence: 99%

Formation of lipoxin B by the pure reticulocyte lipoxygenase via sequential oxygenation of the substrate

Kühn

Wiesner

Alder

et al. 1987

European Journal of Biochemistry

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The pure reticulocyte lipoxygenase converts 1 5LS-hydroxy-5,8,1 1,13(2,Z,Z,E)-icosatetraenoic acid (1 5~~-HETE) methyl ester to a complex mixture of products containing 5~, , 1 4~~, 1 5~~-trihydro(pero)xy-6E,8Z,lOE,12E-icosatetraenoate methyl ester (lipoxin B methyl ester), 5~, , l SL,-D~H(P)ETE methyl ester and four 8 , 1 5~~-DiH(P)ETE methyl ester isomers [DiH(P)ETE = dihydro(pero)xy-icosatetraenoic acid].After a short incubation period (15 min) 5os,15~,-DiH(P)ETE methyl ester was found to be the main product, whereas after a 3-h incubation lipoxin B methyl ester was the predominant product. The reaction shows a remarkable stereoselectivity since only small amounts of other trihydroxy tetraenes are formed. Anaerobiosis, heat inactivation of the enzyme, or incubation in the presence of lipoxygenase inhibitors (icosatetraynoic acid, nordihydroguaiaretic acid) completely abolished the reaction. The complete steric structure of the major tetraene product (lipoxin B methyl ester) was established by ultraviolet spectroscopy, HPLC on four different types of columns, gas chromatography/mass spectrometry, gas/liquid chromatography of the ozonolysis fragments of the menthoxycarbonyl derivatives, and by 400-MHz 'H-NMR.Atmospheric oxygen was incorporated at carbon-5 and carbon-14 into the major product. 5~~, 1 5~~-DiH(P)ETE methyl ester was shown to be an intermediate in the synthesis. Lipoxin B was also formed during the oxygenation of arachidonic acid, 1 SL,-HETE and 5~~, l SL,-D~HETE. The results presented here indicate that lipoxin B can be formed by pure lipoxygenases via a sequential oxygenation of arachidonic acid or its hydro(pero)xy derivatives.

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Section: Mechanism Of Biosynthesismentioning

confidence: 99%

Formation of lipoxin B by the pure reticulocyte lipoxygenase via sequential oxygenation of the substrate

Kühn

Wiesner

Alder

et al. 1987

European Journal of Biochemistry

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“…The available data indicate that LxA4, but not LxB4 contracts guinea-pig lung parenchymal strips (Serhan et al, 1986a), is chemokinetic for human neutrophils (Spur et al, 1988) and induces superoxide anion generation and elastase release from human neutrophils . Human natural killer cells exposed to either LxA4 or LxB4 are unable to provoke target cell lysis (Ramstedt et al, 1985).…”

Section: Introductionmentioning

confidence: 99%

“…Two biologically active lipoxins have been identified, lipoxin A4 (LxA4) and lipoxin B4 (LxB4). LxA4 is 5,6,15-trihydroxy-7,9,11,13-eicosatetraenoic acid (Serhan et al, 1986a) and LxB4 is 5,14,15-trihydroxy-6,8,10,12-eicosatetraenoic acid (Serhan et al, 1986b).…”

Section: Introductionmentioning

confidence: 99%

The contractile activities of lipoxin A₄ and lipoxin B₄ for guinea‐pig airway tissues

Jacques

Spur

Crea

et al. 1988

British J Pharmacology

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The isometric contractile activities of lipoxin A4 (LxA4) and lipoxin B4 (LxB4) were evaluated on guinea‐pig lung tissue over the concentration range, 10−8 to 10−5 m. LxA4 contracted guinea‐pig lung parenchymal strips; the concentration eliciting 50% maximum histamine response was 3 × 10−6 m. LxA4 did not contract tracheal spirals. The LxA4 dose‐response curve was parallel to that of leukotriene D4 (LTD4) with LxA4 being approximately 10,000 fold less potent than LTD4. The time course of the contraction elicited by LxA4 was similar to that of LTD4 and it was slow in onset and did not plateau for 20 min. Pre‐incubation of parenchymal strips with leukotriene receptor antagonists at a concentration of 1 × 10−6 m to 3 × 10−5 m FPL 55712 or 3 × 10−5 m L 649923 inhibited LxA4 activity. Pre‐incubation of tissues with 1 × 10−5 m L 651392, a 5‐lipoxygenase inhibitor, or 1 × 10−5 m indomethacin, a cyclo‐oxygenase inhibitor, did not affect the contractile activity of LxA4. LxB4 did not constrict parenchymal strips or tracheal spirals.

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“…Incubation of human PMNs with 15HPETE leads to the formation of six LXA and at least two LXB isomers [3,4,7]. Very recently, porcine PMNs were found to produce LXB isomers after treatment with phospholipase AZ 181.…”

Section: Introductionmentioning

confidence: 99%

Evidence for lipoxin formation by bovine polymorphonuclear leukocytes via triple dioxygenation of arachidonic acid

et al. 1988

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Incubation of bovine polymorphonuclear leukocytes (PMNs) with arachidonic acid leads to the formation of four lipoxins. The same lipoxins are also formed upon incubation of bovine PMNs with S(S)-hydroperoxy-6truns-8,1 l,ICciseicosatetraenoic acid, S-hydroxy-6-rrans-8,11,14-cis-eicosatetraenoic acid, S(S)-hydroperoxy, 15(S)-hydroxy-6,13-rrans-8,ll -cis-eicosatetraenoic acid or S(s), 1 S(S)-dihydroxy-6,13-fruns-8,11 -cis-eicosatetraenoic acid. A 5,6-epoxide as intermediate in lipoxin formation in the bovine PMN is highly improbable because the 5-hydroxy compounds are as good substrates as the 5-hydroperoxy compounds. Moreover, the two main lipoxins were found to coelute with the two lipoxins produced via a triple dioxygenation of arachidonic acid by soybean lipoxygenase-I . Hence the bovine PMN is the first cell for which evidence is presented that the formation of lipoxins proceeds mainly via triple dioxygenation and not via 15-hydroxy-leukotriene A., as is proposed for human and porcine PMNs.

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On the stereochemistry and biosynthesis of lipoxin B.

Cited by 104 publications

References 18 publications

Formation of lipoxin B by the pure reticulocyte lipoxygenase via sequential oxygenation of the substrate

Formation of lipoxin B by the pure reticulocyte lipoxygenase via sequential oxygenation of the substrate

The contractile activities of lipoxin A₄ and lipoxin B₄ for guinea‐pig airway tissues

Evidence for lipoxin formation by bovine polymorphonuclear leukocytes via triple dioxygenation of arachidonic acid

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On the stereochemistry and biosynthesis of lipoxin B.

Cited by 104 publications

References 18 publications

Formation of lipoxin B by the pure reticulocyte lipoxygenase via sequential oxygenation of the substrate

Formation of lipoxin B by the pure reticulocyte lipoxygenase via sequential oxygenation of the substrate

The contractile activities of lipoxin A4 and lipoxin B4 for guinea‐pig airway tissues

Evidence for lipoxin formation by bovine polymorphonuclear leukocytes via triple dioxygenation of arachidonic acid

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The contractile activities of lipoxin A₄ and lipoxin B₄ for guinea‐pig airway tissues