DOI: 10.1111/j.1432-1033.1994.00959.x. ω‐Oxidation of Lipoxin B<sub>4</sub> by Rat Liver

10.1111/j.1432-1033.1994.00959.x

Crossref journal-article

Wiley

European Journal of Biochemistry (311)

Abstract

Lipoxin B4 (LXB4) is metabolized to 20‐hydroxy‐LXB4 by rat liver microsomes. The ω‐hydroxylation requires both molecular oxygen and NADPH, and is inhibited by carbon monoxide, indicating involvement of a cytochrome P‐450 (P‐450). This is supported by inhibition of the reaction by antibodies raised against NADPH–P‐450 reductase. The P‐450 appears to be the one responsible for leukotriene B4ω‐hydroxylation, because leukotriene B4 inhibits the formation of 20‐hydroxy‐LXB4 and LXB4 blocks the leukotriene B4ω‐hydroxylase activity in microsomes. Incubation of 20‐hydroxy‐LXB4 with both rat liver cytosol and NAD+ leads to formation of a more polar metabolite on high‐performance liquid chromatography. The metabolite is identified as 20‐carboxy‐LXB4, a novel metabolite of LXB4, based on analyses by ultraviolet spectrometry and by gas chromatography/mass spectrometry. The 20‐carboxy‐LXB4‐forming activity is localized in cytosol, with an optimal pH of 8.5. The activity is dependent on NAD+, but NADP+ can not replace NAD+. The reaction is inhibited by pyrazole and 4‐methylpyrazole, inhibitors of alcohol dehydrogenase, and by substrates of the enzyme such as ethanol and 20‐hydroxy‐leukotriene B4. Disulfiram, an inhibitor of aldehyde dehydrogenase, also blocks the 20‐carboxy‐LXB4 formation. These observations suggest that both alcohol dehydrogenase and aldehyde dehydrogenase participate in the oxidation of 20‐hydroxy‐LXB4 to 20‐carboxy‐LXB4.

Bibliography

Mizukami, Y., Sumimoto, H., Isobe, R., Minakami, S., & Takeshige, K. (1994). ÏâOxidation of Lipoxin B4 by Rat Liver. European Journal of Biochemistry, 224(3), 959â965. Portico.

Authors 5

Yoichi Mizukami (first)
Hideki Sumimoto (additional)
Ryuichi Isobe (additional)
Shigeki Minakami (additional)
Koichiro Takeshige (additional)

References 47 Referenced 10

10.1126/science.2820055
10.1016/0020-711X(88)90060-2
10.1002/anie.199111001
10.1016/0005-2760(92)90297-9
10.1111/j.1748-1716.1987.tb08187.x
10.1016/0006-291X(87)91337-4
10.1016/0014-5793(88)80384-3
10.4049/jimmunol.135.5.3434
10.1016/0005-2760(89)90096-9
10.1073/pnas.85.21.8340
{'key': 'e_1_2_3_12_2', 'first-page': '80', 'volume': '107', 'author': 'Popov G. K.', 'year': '1989', 'journal-title': 'Byull. Biol. Med.'} / Byull. Biol. Med. by Popov G. K. (1989)
10.1269/jrr.29.255
10.1016/0014-5793(81)80676-X
10.1016/S0021-9258(17)43263-7
10.1016/0006-291X(84)90583-7
10.1172/JCI112077
10.1016/S0021-9258(18)45220-9
10.1111/j.1432-1033.1988.tb13889.x
{'key': 'e_1_2_3_20_2', 'first-page': '381', 'volume': '20', 'author': 'Sumimoto H.', 'year': '1990', 'journal-title': 'Biochem. Int.'} / Biochem. Int. by Sumimoto H. (1990)
10.1016/S0021-9258(18)98360-2
10.1016/S0021-9258(18)68432-7
10.1016/S0021-9258(19)39570-5
10.1111/j.1432-1033.1989.tb14557.x
10.1016/0005-2760(90)90109-B
10.1016/S0021-9258(19)75676-2
10.1093/oxfordjournals.jbchem.a123183
10.1016/0005-2760(88)90042-2
10.1016/S0021-9258(19)57231-3
10.1016/S0021-9258(18)54295-2
10.1111/j.1432-1033.1987.tb13669.x
10.1016/S0021-9258(18)69136-7
10.1111/j.1432-1033.1992.tb17287.x
10.1016/0090-6980(83)90132-6
10.1016/0014-5793(81)81233-1
{'key': 'e_1_2_3_36_2', 'first-page': '1406', 'volume': '98', 'author': 'Samhoun M. N.', 'year': '1989', 'journal-title': 'Br. J. Pharmacol.'} / Br. J. Pharmacol. by Samhoun M. N. (1989)
10.1016/0014-5793(93)81165-V
10.1016/0005-2760(93)90270-J
10.1021/bi00076a002
10.1016/0006-291X(91)91958-F
10.1016/0076-6879(67)10042-6
10.1016/S0076-6879(78)52009-0
{'key': 'e_1_2_3_43_2', 'first-page': '118', 'volume-title': 'vol. 3', 'author': 'Vassault A.', 'year': '1983'} / vol. 3 by Vassault A. (1983)
10.1073/pnas.83.7.1983
10.1073/pnas.81.17.5335
10.1016/0005-2760(90)90293-7
10.1016/0163-7258(80)90038-8
{'key': 'e_1_2_3_48_2', 'first-page': '127', 'volume-title': 'Cytochrome P‐450', 'author': 'Kusunose M.', 'year': '1993'} / Cytochrome P‐450 by Kusunose M. (1993)

Dates

Type	When
Created	20 years, 5 months ago (March 4, 2005, 2:53 a.m.)
Deposited	1 year, 10 months ago (Oct. 1, 2023, 4:33 p.m.)
Indexed	1 year, 10 months ago (Oct. 2, 2023, 12:29 a.m.)
Issued	30 years, 11 months ago (Sept. 1, 1994)
Published	30 years, 11 months ago (Sept. 1, 1994)
Published Online	20 years, 5 months ago (March 3, 2005)
Published Print	30 years, 11 months ago (Sept. 1, 1994)

Funders 0

None

BibTeX

@article{Mizukami_1994, title={ω‐Oxidation of Lipoxin B4 by Rat Liver: Identification of an ω‐Carboxy Metabolite of Lipoxin B4}, volume={224}, ISSN={1432-1033}, url={http://dx.doi.org/10.1111/j.1432-1033.1994.00959.x}, DOI={10.1111/j.1432-1033.1994.00959.x}, number={3}, journal={European Journal of Biochemistry}, publisher={Wiley}, author={Mizukami, Yoichi and Sumimoto, Hideki and Isobe, Ryuichi and Minakami, Shigeki and Takeshige, Koichiro}, year={1994}, month=sep, pages={959–965} }

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