12-Hydroxy-5,8,10,14-eicosatetraenoic

WooUard, P.M. (1986). Stereochemical differences between 12-hydroxy-5,8,10,14-eicosatetraenoic acid in platelets and psoriatic lesions. Biochem. Biophys. Res. Commun. 136, 169-176. 

Previously, we reported the effects of Morus flavonoids on arachidonate metabolism in rat platelet homogenates, such as inhibition of 12-hydroxy-5,8,10-heptadecatrienoic acid (HHT), thromboxane B2, and 12-hydroxy -5,8,10,14-eicosatetraenoic acid (12-HETE) [79,80]. As described in the... 

The other metabolic pathway derived from arachidonic acid is through the activity of the lypoxygenase-12 (2-LOX) (Fig. 5). 2-LOX converts arachidonic acid (AA) to 12-hydroperoxy-5,8,10,14-eicosatetraenoic acid (12-HPETE) that is rapidly reduced by peroxidases to the stable 12-hydroxy-5,8,10,14-eicosatetraenoic acid (12-HETE). In... 

Dehydroabietyl isocyanate, [39], was used by Falck et al. to determine the absolute configuration of hydroxyeicosatetraenoic acid methyl esters in a study of the enzymatic epoxidahon of arachidonic acid (175). In another study of similar metabolites, the stereochemical identity of 12-hydroxy-5,8,10,14-eicosatetraenoic acid derived from the lesional scale of patients with psoriasis was studied via separation of the enantiomers after derivatization with [39] (176). In these studies (175,176), LC separation of the derivatives was used. CDA [39] can be prepared from commercially available resolved dehydroabietylamine. It would be worthwhile to examine the applicability of this CDA to the resolution of other compounds. 

Siegel MI, McConnel RT, Cuatrecasas P (1979) Aspirin-like drugs interfere with arachidon-ate metabolism by inhibition of the 12-hydroxy-5,8,10,14-eicosatetraenoic acid peroxidase activity of the lipoxygenase pathway. Proc Natl Acad Sci USA 76 3774-3778 Slapke J, lager L (1979) Untersuchungen zum Analgetika-Asthma. Gesellschaft Inn Med DDR 34 78-80... 

ROBERTS LJ 11, LEWIS RA, OATES JO, AUSTEN KF Prostaglandin, tromboxane, and 12-hydroxy-5,8,10,14-eicosatetraenoic acid production by ionophore - stimulated rat serosal mast cells. Biochim. Biophys. Acta 575 185 - 192, 1979,... 

Powell, WS, Hashefi, M, Falck, JR, Chauhan, K, Rokach, J, Wang, SS, Mills, E and MacLeod, RJ (1995) Effects of oxo and dihydro metabolites of 12-hydroxy-5,8,10,14-eicosatetraenoic acid on chemotaxis and cytosolic calcium levels in human nentrophUs. J Leukoc Biol, 57, 257—263. 

The fragmentation pattern of deprotonated 12-HETE (12-hydroxy-5,8,10,14-eicosatetraenoic acid) contains six abundant product ions at m/z 301, 257, 207, 179, 163, and 135 (Figure 10.4e). The first two ions correspond to the loss of water and water plus carbon dioxide. The m/z 207 ion yields from the cleavage of the C12-C13 bond through formation of aldehyde at the end (Cl2 site). This ion further loses a... 

We have already stressed the potential importance of lipid-rich membranes in the skin as potential targets for ROS-induced damage and ageing of human skin is morphologically identical to changes found by peroxidative processes (Serri et al., 1977). The involvement of AA metabolites in skin disease, and in particular psoriasis, has been the subject of much recent interest. Studies have included topical and intradermal administrations of AA metabolites, and assay of such products in clinical specimens. Results show that concentration of AA, 12-hydroxy-eicosatetraenoic acid (12-HETE), PG and leu-kotrienes are increased in psoriatic lesions (Hammarstrom etal., 1975 Camp etal., 1983 Brain etal., 1984 Duell et al., 1988) and also that full-thickness epidermis from normal and diseased skin has the enzymatic capacity to convert AA to some of the same metabolites (Hammarstrom etal., 1975, 1979 Camp etal., 1983 Brain etal., 1984 Ziboh et al., 1984 DueU et al., 1988). The biological effect of both 12-HETE and leukotrienes was confirmed by both topical application and intradermal injection, which caused epidermal inflammation and... 

Chan, C.C., Duhamel, L. and Ford-Hutchison, A. (1985). Leukotriene B4 and 12-hydroxy eicosatetraenoic acid stimulate epidermal proliferation in vivo in the guinea pig. J. Invest. Dermatol. 85, 333-334. 

Guido DM, McKenna R, Mathews WR. 1993. Quantitation of hydroperoxy- eicosatetraenoic acids and hydroxy-eicosatetraenoic acids as indicators of lipid peroxidation using gas chromatography-mass spectrometry. Anal Biochem 209 123-129. 

Eicosonoids (prostaglandins, thromboxanes, leukotrienes) hydroxyperoxy-eicosatetraenoic acid hydroxy-eicosatetraenoic acid Omega-3 acids... 

A,, 8-hydroxyeicosatetraenoic acid, 12-hydroxy-eicosatetraenoic acid, and 12-hydroxystearic acid . The physiological relevance of some of these reactions is of interest but the effects of variability of P450 4F2 have not been demonstrated. Part of the interest lies in the fact that leukotriene... 

McGiff, J.C. and J. Quilley (2001). 20-Hydroxy-eicosatetraenoic acid and epoxyeicosatrienoic acids and blood pressure. Curr. Opin. Nephrol. Hypertens. 10, 31-237, and cited references. 

Temowitz, T., Fogh, K., and Kragballe, K. (1988) Specific Inhibition of Leukotriene B -Induced Neutrophil Chemotaxis by 15-Hydroxy-eicosatetraenoic Acid (15-HETE), Skin Pharmacol. 1, 93-99. 

For example, isomers of the hydroxy-eicosatetraenoic acid are difficult to separate chromatographically (Figure 1.12b), and a simple mass analysis shows overlapping peaks for the parent ions (Figure 1.12c). However, a triple quadrupole instrument enables to measure specific daughter ions of the two isomers and the daughter ion traces show no interferences between the two isomers [94]. 

Lagarde M, Gharib A and Dechavanne M, A simple radiochemical assay of thromboxane B2, 12-hydroxy-eicosatetraenoic acid (HETE) and 12-hydroxy-heptadecatrienoic acid (HHT) synthetized by human platelets. Clin. Chim. Acta 79, 255-259, 1977. 

Starfish oocytes rapidly converted radiolabelled AA into lipoxygenase products, specifically 8-hydroxyeicosatetraenoic acid [70]. Subsequent work showed that oocyte maturation is induced in a stereospecific way by (8/ )-hydroxy-eicosatetraenoic acid [71]. Again, the authors concluded that this compound is involved in transducing the oocyte maturation hormone signal at the plasma membrane level. 

Rabbit alveolar macrophages exhibited an apparent discrepancy between the abundance of immu-nospecific cP450 4A protein and no 20-hydroxy-eicosatetraenoic acid production (Zhu et al. 1998). NO generated by alveolar macrophages may auto-inhibit the P450 4A enzymes and production of 20-HETE in these cells. 

Di Marzo, V., Ventriglia, M., MoHo, E., Mosca, M and Cimino, G. (1996) Occurrence and biosynthesis of ll(R)-hydroxy-eicosatetraenoic acid (11-R-HETE) in the Caribbean soft coral Plexaurella dichotoma. Experientia, 52,834-838. 

LT leukotriene, TX thromboxane, HPETE hydroperoxy eicosatetraenoic acid, hydroxy eicosatetraenoic acid, HHT12 hydroxyheptadecatrienoic acid (17 carbon), MDA malondialdehyde (3 carbon)... 

Hammarstrom, S., Hamberg, M., Samuelsson, B., Duell, E.A., Stawiski, M. and Voorhees, J.J. (1975). Increased concentrations of non-esterified arachidonic acid, 12L-hydroxy-5,8,10,14-eicosatetraenoic acid, prostaglandin E2 and prostaglandin F2 in epidermis of psoriasis. Proc. Natl Acad. Sci. USA 72, 5130-5134. 

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