DHA Metabolism: Targeting the Brain and Lipoxygenation

Abstract

Docosahexaenoic acid (DHA), the end-product of the metabolism of omega-3 family fatty acids, is the main polyunsaturated fatty acid of the brain, but its accumulation is incompletely understood. This paper reviews how it could accumulate through specific uptake of DHA-containing lysophosphatidylcholine (LysoPC-DHA). DHA migrates very easily from the sn-2 position of LysoPC, which could be considered as the physiological form of polyunsaturated LysoPC, to the sn-1 position, which is much more stable. An approach preventing migration by acetylating the sn-1 position, while retaining the main physico-chemical properties of the carrier, is described. Also, the double lipoxygenation and bond-isomerization of DHA into 10(S),17(S)-docosahexa-4Z,7Z,11E,13Z,15E,19Z-enoic acid, named PDX, by soybean lipoxygenase is described. As in other E,Z,E conjugated trienes, PDX is shown to inhibit human blood platelet aggregation at submicromolar concentrations.

Docosahexaenoic acid–mediated, targeted and sustained brain delivery of curcumin microemulsion

“…The oil in the MEs influenced the in vivo behavior with CUR DHA ME exhibiting significantly higher C max (maximum concentration), higher area under the curve (AUC) and longer half-life (t 1/2 ) compared to CUR Capmul ME (Table 1). This is attributed to DHA being a long-chain triglyceride, hence exhibiting slow metabolism (Tamilvanan, 2009;Picq et al, 2010;Siddiqui et al, 2013b). The enhancement in plasma AUC compared to CUR solution was 3.79-fold for CUR Capmul ME and a striking 5.74-fold for CUR DHA ME (Figure 2A (a)).…”

Metabolismo, oxidação e implicações biológicas do ácido docosahexaenoico em doenças neurodegenerativas

“…50,54 O tecido nervoso apresenta 3 isoformas de LOX (5-LOX, 12-LOX e 15-LOX) capazes de oxidar DHA gerando hidroperóxidos específicos. 55 A nomenclatura das diferentes isoformas da LOX é baseada na posição que a mesma oxida o ácido araquidônico. O DHA pode ser convertido pela 5-LOX (enzima responsável pela produção de leucotrienos a partir do ácido araquidônico) em 7-hidroperoxi-DHA e sua forma reduzida 7-hidroxi-DHA.…”

Evaluation of the Effect of Feeding on Portulaca Oleracea Seed Oil on Biosynthesis of Long Chain Polyunsaturated Fatty Acids in Rats.

“…Common vegetable oils (corn, sunflower and soybean) contain two essential fatty acids, but the presence of LA is much higher than that of ALA (Kamal-Eldin and Andersson, 1997). Many researches points to the important physiological roles played by EPA and DHA for the human body, whether in the stages of childhood through different stages of growth and also for the elderly (Harris, 2009;Kanai et al, 2011;Li and Hu, 2009;Picq et al, 2010) In general, humans can obtain the long chain polyunsaturated fatty acids (LCPUFA) from the family of omega 3 (EPA and DHA) and omega 6 (Arachidonic acid [C20:4 n-6 or AA]) in one of two ways: either directly ingested through different foods or bio-converted from two essential fatty acids (ALA for omega 3 and LA for omega 6) (Brenner, 2003). The dependence on consumption of EPA and DHA directly is usually low for different reasons; first is the high price of cold water fish (rich source for EPA and DHA); second is theses fishes polluted with Since the same group of enzymes (desaturases, chain-elongases and eicosanoid synthesis) which works to synthesis eicosanoid in three fatty acids families (omega 3, omega 6 and omega 9) so ALA (18:3n-3) competes with LA (18:2n-6) and oleic acid (18:1n-9) (Dinh et al, 1993;Lands et al, 1992), for this reason the balance between LA and ALA is one of the most important factors in bio-synthesis and accumulation of EPA and DHA (Araya et al, 2010).…”