DOI: 10.1073/pnas.83.7.1983. On the stereochemistry and biosynthesis of lipoxin B.

On the stereochemistry and biosynthesis of lipoxin B.

10.1073/pnas.83.7.1983

Crossref journal-article

Proceedings of the National Academy of Sciences

Proceedings of the National Academy of Sciences (341)

Abstract

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.

Bibliography

Serhan, C. N., Hamberg, M., Samuelsson, B., Morris, J., & Wishka, D. G. (1986). On the stereochemistry and biosynthesis of lipoxin B. Proceedings of the National Academy of Sciences, 83(7), 1983â1987.

Authors 5

C N Serhan (first)
M Hamberg (additional)
B Samuelsson (additional)
J Morris (additional)
D G Wishka (additional)

References 0 Referenced 81

None

Dates

Type	When
Created	19 years, 3 months ago (May 31, 2006, 6:16 a.m.)
Deposited	3 years, 4 months ago (April 13, 2022, 12:27 p.m.)
Indexed	1 month ago (Aug. 2, 2025, 12:25 a.m.)
Issued	39 years, 5 months ago (April 1, 1986)
Published	39 years, 5 months ago (April 1, 1986)
Published Online	39 years, 5 months ago (April 1, 1986)
Published Print	39 years, 5 months ago (April 1, 1986)

Funders 0

None

BibTeX

@article{Serhan_1986, title={On the stereochemistry and biosynthesis of lipoxin B.}, volume={83}, ISSN={1091-6490}, url={http://dx.doi.org/10.1073/pnas.83.7.1983}, DOI={10.1073/pnas.83.7.1983}, number={7}, journal={Proceedings of the National Academy of Sciences}, publisher={Proceedings of the National Academy of Sciences}, author={Serhan, C N and Hamberg, M and Samuelsson, B and Morris, J and Wishka, D G}, year={1986}, month=apr, pages={1983–1987} }

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