Pentaenoic acid

Shimizu S, S Jareonkitmongol, H Kawashima, K Akimoto, H Yamada (1991) Production of a novel wl-eicosa-pentaenoic acid by Mortierella alpina lS-4 grown on 1-hexadecene. Arch Microbiol 156 163-166. 

Finally, an intriguing possible future therapy arises from a radical idea of Horrobin (2001) that schizophrenia is a nutritional disorder linked to a decreased intake of essential polyunsaturated fatty acids. Recent 31P-MRS studies have shown changes in plasma membrane phospholipids in the neocortex of unmedicated schizophrenics, which would have deleterious consequences on synaptic neurotransmission (Fukuzako, 2001). A clinical trial with the co6 fatty acid derivative ethyleicosa-pentaenoic acid (LAX-101) in patients who had been unresponsive to clozapine, reported that a daily dose of 2g LAX-101 gave a 26% improvement in symptoms over 12 weeks compared with 6% with placebo (Peet and Horrobin, 2001). Maybe in... 

Studies of the natural products of the antipatharian (Hexacorallia), Leiopathes sp., obtained during an expedition to the South Indian Ocean, led to the isolation of one novel oxylipin, (+)- 10P-hydroxydocosa-7Z, 11E, 13Z, 16Z, 19Z-pentaenoic acid (= leiopathic acid, 31), as well as two known compounds,... 

Quil-A saponin toxicity. Mice fed Quil-A-supplemented diet (a saponin that emulsifies fats and potentiates the immune responses) showed higher level of docosa-pentaenoic acid in the liver. These changes were associated with a significant reduction in the plasma PGEl and PGE2 and thrombohane-B2 levels in response to an intraperitoneal injection of a lethal dose of lipopolysaccharide endotoxin, LDjf, 20 mg/ kg. The data suggest that sesame seed oil and Quil A, when present in the diet, exerted cumulative effects that resulted in a decrease in the levels of dienoic eicosanoids with a reduction in lL-1 P and a con-commitant elevation in the levels of lL-10 that were associated with a marked increase survival in mice . ... 

Recent interest has focused on the C20 5 eicosa-pentaenoic acid (EPA) and the C22 6 docosa-hexaenoic acids (DHA). These 3 (or n-3) polyunsaturated acids are formed from linolenic acid by marine algae and are found in fish oils.h The C22 5 and C22 6 acids can be converted to prostaglandins of the PG4 and PG5 series. DHA together with the 0)6 C22 4 acid constitutes over 30% of the fatty acids in brain phospholipids. In the... 

Fish oil supplements (SEDA-13, 460) (SEDA-18, 3), rich in long-chain polyunsaturated ( -3 fatty acids (eicosa-pentaenoic acid, docosahexaenoic acid), can reduce plasma concentrations of triglycerides and VLDL cholesterol, reduce platelet aggregation, prolong bleeding time, reduce blood pressure, increase the fluidity of the blood, and affect leukotriene production. Reported adverse effects include fullness and epigastric discomfort, diarrhea, and a fishy taste after belching. In addition to these mild symptoms, certain areas have been identified in which problems of a more serious nature could arise ... 

Eicosanoids are a class of lipids that include the prostaglandins, thromboxanes, and leukotrienes. Eicosanoids derive their name from their common origin, that is, from C20 polyunsaturated fatty acids, the eicosaenoic acids, particularly arachidonic acid (all-cw-5,8,ll,14-eicosatetraenoic acid). Related trienoic and pentaenoic acids are minor precursors to some of these compounds. 

Fig.l. Effects of various fatty acids on lipopolysaccharide (LPS)-induced tumor necrosis-factor (TNF)-a production. THP-1 cells preincubated with 60 iM of docosahexaenoic acid (DL), eicosa-pentaenoic acid (EL), arachidonic acid (AL), oleic acid (OL) or stearic acid (SL) for 24 h were stimulated with LPS for 6 h. The amount of TNF-a produced in the control LPS-stimulated cells (L) is set as 100%. TNF-a levels in cell culture supernatant were determined by enzyme-linked immunosorbent assay. Values are means SEM, n = 3. Significantly different from control group (P< 0.05). 

Arita, M., Yoshida, M., Hong, S., Tjonahen, R., Glickman, J.N., Petasis, N.A., Blumberg, R.S., and Serhan, C.N. (2005) Resolvin R1, an endogenous lipid mediator derived from omega-3 eicosa-pentaenoic acid, protects against 2,4,6-trinitrobenzene sulfonic... 

In many instances, oxidized products are considerably more stable when formed in complex lipids, like phospholipids or cholesteryl esters, and alkaline hydrolysis is required to release the oxidized lipid for analysis. Separation and quantitation of mono-hydroxyicosanoids by HPLC has been regularly used for the last 30 years. The procedures have become routine and there are now published procedures for automating the analysis [60]. A recent review by Yin et al. [36] describes in detail how to quantify both mono-hydroxyeicosatetraenoates and F2-isoprostanes. Similar procedures can be used to separate and identify products derived from (5Z,8Z,llZ,14Z,17Z)-eicosa-5,8,11,14,17-pentenoic acid, (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoic acid, and (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid. 

Sprecher et al., 1965). The decatrienoic acids isolated from the latex of Euphorbia pulcherrima include the 2M 6c, 2c4 6, 3t5tle and 3c5t7t isomers (Warnaar, 1977), Two unusual pentaenoic acids (12 5 3,5,7,9,11 and 14 5 3,5,7,9,11) have been identified in the body fat of the coccid Llaveia axin at around the 10% level (Cason etal., 1971). 

Pentaenoic acids (conjugated), 11 Pentaerythritol, 245 Pentahydroxystearic acid, 21 Pentane, 457... 

The name leukotriene was introduced for two reasons (i) they were discovered in leucocytes [23] and (ii) they contain a conjugated triene chromophore. Leukotrienes are abbreviated to LT followed by a capital letter (A, B, C, D or E) and a subscript. The capital letter indicates the chemical structure of the substituents and the subscript the number of double bonds which is the same as in the fatty acid substrate used for leukotriene synthesis. AA, which contains four double bonds, is converted into leukotrienes of the 4-series. In contrast, PGs of the 2-series are formed from this substrate. The reasons for the different degree of unsaturation of PGs and leukotrienes is the fact that during PG formation two double bonds are lost whereas all double bonds are retained during leukotriene synthesis. When (5Z,82,112,142,17Z)-eicosa-5,8,ll,14,17-pentaenoic acid is used as substrate,... 

Oleic, linoleic and a-linolenic acids are desaturated by the same microsomal enzyme called A6 desaturase since it introduces the double bond between carbons 6-7 (Brenner and Peluffo, 1966 Brenner, 1971 Inkpen et al, 1969 Brenner, 1974). This enzyme is different from the A5 desaturase that converts eicosa-8, 11-dienoic, eicosa-9, 11, 14-trienoic and eicosa-8, 11, 14, 17-tetraenoic acids to eicosa-5, 8, 11-trienoic, eicosa-5, 8, 11, 14-tetraenoic and eicosa-5, 8, 11, 14, 17-pentaenoic acids respectively. (Ninno et al, 1974 Alaniz et al, 1975 Caspar et al, 1975). It is also different from the A9 desaturase (Brenner, 1971). The A6 desaturase recognizes the number of double bonds of the substrate since a-linolenate is desaturated faster than linoleate and this one faster than oleate (Brenner and Peluffo, 1966). However, it is not known yet the effect of the chain length of the acid on the activity of the enzyme. 

In the rat the 22-carbon pentaenoic acid, derived from linoleic via arachidonic acid and 22 4, triples in concentration during sexual maturation and appears to be associated with the appearance and development of spermatids. Further testicular metabolism of the 22 5 include its oxidation to CO2, its conversion to 24-carbon polyenes and its retroconversion to arachidonic acid. 

Hammerstrom, S. (1980) Leukotriene C5 a slow reacting substance derived from eicosa-pentaenoic acid. J. Biol. Chem. 255, 7093-7094. 

Driss, F., Vericel, E., Lagarde, M., Dechavanne, M. and Darcet, Ph. (1984) Inhibition of platelet aggregation and thromboxane synthesis after intake of small amounts of icosa-pentaenoic acid. Thromb. Res. 36, 389-396. 

---