Stress-induced Generation of N-acylethanolamines in Mouse Epidermal JB6 P+ Cells

Overview

Journal Biochem J

Specialty Biochemistry

Date 2000 Mar 24

PMID 10677355

Citations 24

Authors

E V Berdyshev

P C Schmid

Z Dong

H H SCHMID

Affiliations

Soon will be listed here.

Abstract

It has long been known that N-acylethanolamine phospholipids [N-acylphosphatidylethanolamine (N-acyl PE)] and N-acylethanolamines (NAEs) accumulate in mammalian tissues undergoing degenerative membrane changes associated with necrosis. Here we studied the effects of stress factors (UVB irradiation and serum deprivation) on the endogenous levels of N-acyl PE and NAE in mouse epidermal JB6 P(+) cells. We found that 16:0, 18:0, 18:1,n-9 and 18:1,n-7 are the predominant amide-linked fatty acids in both N-acyl PE and NAE in these cells. UVB irradiation and serum deprivation resulted in significantly increased levels of N-acyl PE and NAE, especially 18:1, n-9 N-acyl PE and NAE. UVB challenge increased the cellular content of anandamide (20:4,n-6 NAE), but this increase was the lowest of all NAEs measured. Serum deprivation resulted in a decreased cellular anandamide level, as well as a decrease in 20:4,n-6 N-acyl PE. Interestingly, the replacement of serum-free medium with medium containing 5% (v/v) fetal calf serum after 36 h of serum deprivation restored N-acyl PE and NAE levels almost completely within 4-8 h. These data suggest the involvement of N-acyl PE and NAE in cellular responses to stress.

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References

Epps D, Natarajan V, Schmid P, Schmid H . Accumulation of N-acylethanolamine glycerophospholipids in infarcted myocardium. Biochim Biophys Acta. 1980; 618(3):420-30. DOI: 10.1016/0005-2760(80)90260-x. View

BLIGH E, Dyer W . A rapid method of total lipid extraction and purification. Can J Biochem Physiol. 1959; 37(8):911-7. DOI: 10.1139/o59-099. View

Natarajan V, Reddy P, Schmid P, SCHMID H . N-Acylation of ethanolamine phospholipids in canine myocardium. Biochim Biophys Acta. 1982; 712(2):342-55. DOI: 10.1016/0005-2760(82)90352-6. View

Schmid P, Reddy P, Natarajan V, SCHMID H . Metabolism of N-acylethanolamine phospholipids by a mammalian phosphodiesterase of the phospholipase D type. J Biol Chem. 1983; 258(15):9302-6. View

Staberg B, Wulf H, Klemp P, Poulsen T, BRODTHAGEN H . The carcinogenic effect of UVA irradiation. J Invest Dermatol. 1983; 81(6):517-9. DOI: 10.1111/1523-1747.ep12522855. View

Sugita M, Willians M, DULANEY J, Moser H . Ceramidase and ceramide synthesis in human kidney and cerebellum. Description of a new alkaline ceramidase. Biochim Biophys Acta. 1975; 398(1):125-31. DOI: 10.1016/0005-2760(75)90176-9. View

Epps D, Schmid P, Natarajan V, SCHMID H . N-Acylethanolamine accumulation in infarcted myocardium. Biochem Biophys Res Commun. 1979; 90(2):628-33. DOI: 10.1016/0006-291x(79)91281-6. View

Reddy P, Schmid P, Natarajan V, Muramatsu T, SCHMID H . Properties of canine myocardial phosphatidylethanolamine N-acyltransferase. Biochim Biophys Acta. 1984; 795(1):130-6. DOI: 10.1016/0005-2760(84)90113-9. View

Natarajan V, Schmid P, SCHMID H . N-acylethanolamine phospholipid metabolism in normal and ischemic rat brain. Biochim Biophys Acta. 1986; 878(1):32-41. DOI: 10.1016/0005-2760(86)90341-3. View

10.

Strickland P . Photocarcinogenesis by near-ultraviolet (UVA) radiation in Sencar mice. J Invest Dermatol. 1986; 87(2):272-5. DOI: 10.1111/1523-1747.ep12696669. View

11.

Schmid P, Natarajan V, Weis B, SCHMID H . Hydrolysis of N-acylated glycerophospholipids by phospholipases A2 and D: a method of identification and analysis. Chem Phys Lipids. 1986; 41(3-4):195-207. DOI: 10.1016/0009-3084(86)90022-8. View

12.

Newman J, Stiers D, Anderson W, SCHMID H . Phase behavior of synthetic N-acylethanolamine phospholipids. Chem Phys Lipids. 1986; 42(4):249-60. DOI: 10.1016/0009-3084(86)90084-8. View

13.

Stein B, Rahmsdorf H, Steffen A, Litfin M, Herrlich P . UV-induced DNA damage is an intermediate step in UV-induced expression of human immunodeficiency virus type 1, collagenase, c-fos, and metallothionein. Mol Cell Biol. 1989; 9(11):5169-81. PMC: 363669. DOI: 10.1128/mcb.9.11.5169-5181.1989. View

14.

Devary Y, Gottlieb R, Lau L, Karin M . Rapid and preferential activation of the c-jun gene during the mammalian UV response. Mol Cell Biol. 1991; 11(5):2804-11. PMC: 360059. DOI: 10.1128/mcb.11.5.2804-2811.1991. View

15.

SCHMID H, Schmid P, Natarajan V . N-acylated glycerophospholipids and their derivatives. Prog Lipid Res. 1990; 29(1):1-43. DOI: 10.1016/0163-7827(90)90004-5. View

16.

Devane W, Hanus L, Breuer A, Pertwee R, Stevenson L, Griffin G . Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science. 1992; 258(5090):1946-9. DOI: 10.1126/science.1470919. View

17.

Domingo J, Mora M, De Madariaga M . Incorporation of N-acylethanolamine phospholipids into egg phosphatidylcholine vesicles: characterization and permeability properties of the binary systems. Biochim Biophys Acta. 1993; 1148(2):308-16. DOI: 10.1016/0005-2736(93)90144-o. View

18.

Ambrosini A, Bertoli E, Mariani P, Tanfani F, Wozniak M, Zolese G . N-acylethanolamines as membrane topological stress compromising agents. Biochim Biophys Acta. 1993; 1148(2):351-5. DOI: 10.1016/0005-2736(93)90149-t. View

19.

Felder C, Briley E, Axelrod J, Simpson J, Mackie K, Devane W . Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc Natl Acad Sci U S A. 1993; 90(16):7656-60. PMC: 47201. DOI: 10.1073/pnas.90.16.7656. View

20.

Hanus L, Gopher A, Almog S, Mechoulam R . Two new unsaturated fatty acid ethanolamides in brain that bind to the cannabinoid receptor. J Med Chem. 1993; 36(20):3032-4. DOI: 10.1021/jm00072a026. View