ω-3 Arachidonic acid

ω-3 Arachidonic acid是一种婴儿生长发育所必需的多聚脂肪酸。ω-3 Arachidonic acid 抑制花生四烯醇辅酶 A 合成酶，Ki 值为 14 µM。对小牛脑提取物的花生四烯醇辅酶 A 合成酶也有抑制作用，IC50 值约为 5 µM。

omega-3 Arachidonic Acid methyl ester 主要包括二十二碳六烯酸、二十碳五烯酸和 α-亚油酸，是正常生长发育所需的必需膳食营养素。omega-3 Arachidonic Acid methyl ester 是一种中性脂溶性的稀有脂肪酸，属于ω-3花生四烯酸。作为一个组，ω-3脂肪酸与炎症及自身免疫活动的降低有关，同时也减少血栓形成和血小板活化。

omega-3 Arachidonic acid ethyl ester是一种多不饱和脂肪酸，可用于生物化学实验和药物合成研究。

4-hydroxy Nonenal is a lipid peroxidation product derived from oxidized ω-6 polyunsaturated fatty acids such as arachidonic acid and linoleic acid. [1] [2] It exhibits various biological activities such as cytotoxicity, growth inhibiting activity, genotoxicity, and chemotactic activity and has been widely used as a marker of lipid peroxidation.[1][2][3] 4-oxo-2-Nonenal is a more recently identified product of lipid peroxidation.[4][5][6] It actively modifies histidine and lysine residues on proteins and causes protein cross-linking. [7][8] 4-oxo-2-Nonenal also modifies 2’-deoxyguanosine, further implicating lipid peroxidation in mutagenesis and carcinogenesis.[4]

12(S)-HEPE is a monohydroxy fatty acid synthesized from EPA by the action of 12-LO. Unstimulated neutrophils metabolize 12(S)-HEPE to 12(S),20-diHEPE, whereas stimulated neutrophils produce 5(S),12(S)-HEPE via the 5-lipoxygenase pathway. The competitive action of 12(S)-HEPE with arachidonic acid as a substrate for 5-LO in the formation of leukotrienes may provide a basis for the anti-inflammatory potential of ω-3 fatty acids.

Heneicosapentaenoic Acid (HPA) is a 21:5 ω-3 fatty acid present in trace amounts in the green alga B. pennata and in fish oils. Its chemical composition is similar to eicosapentaenoic acid (EPA) except elongated with one carbon on the carboxyl end, placing the first double bond in the δ6 position. HPA can be used to study the significance of the position of the double bonds in ω-3 fatty acids. It incorporates into phospholipids and into triacylglycerol in vivo with the same efficiency as EPA and docosahexaenoic acid and exhibits strong inhibition of arachidonic acid synthesis from linoleic acid. HPA is a poor substrate for prostaglandin H synthase (PGHS) (cyclooxygenase) and for 5-lipoxygenase but retains the ability to rapidly inactivate PGHS.

All-cis-4,7,10,13,16-Docosapentaenoic acid (all-cis-4,7,10,13,16-DPA) methyl ester, also known as Osbond acid, is an isomer of DPA and a more lipid-soluble variant of the free acid, primarily found in fish oils as an ω-3, 22-carbon fatty acid. Despite being an ω-6 fatty acid synthesized through the elongation and desaturation of arachidonic acid, its levels can decrease due to fatty acid desaturase syndrome, potentially impacting development. Additionally, increased expression of hepatic elongation of very long fatty acids protein 6 and elevated levels of very long-chain fatty acids, including all-cis-4,7,10,13,16-DPA, are indicative of nonalcoholic steatohepatitis, a condition that precedes hepatocellular carcinoma.

Heneicosapentaenoic Acid (HPA), a 21:5 ω-3 fatty acid, is found in minute quantities in green algae and fish oils, resembling eicosapentaenoic acid (EPA) but with an added carbon on the carboxyl end, positioning the initial double bond at the Δ6 location. HPA serves as a tool for examining the impact of double bond positions within n-3 fatty acids, as it is incorporated into phospholipids and triacylglycerol in vivo as efficiently as EPA and docosahexaenoic acid (DHA), while significantly inhibiting the synthesis of arachidonic acid from linoleic acid. Moreover, the ethyl ester variant of heneicosapentaenoic acid offers a more lipophilic and stable alternative to the free acid form.

(±)17(18)-EpETE-Ethanolamide, an ω-3 endocannabinoid epoxide, originates from eicosapentaenoic ethanolamide (EPEA) through cytochrome P450 (CYP) epoxygenases action and is decomposed by soluble epoxide hydrolase (sEH) and fatty acid amide hydrolase (FA, AH). Its endogenous synthesis occurs in LPS-stimulated and EPEA-supplemented BV-2 microglia cells, a process inhibited by the CYP inhibitor ketoconazole. This compound mitigates IL-6 and nitrite levels while enhancing IL-10 production following LPS exposure in BV-2 microglia. At a dose of 50 µM, it prevents platelet aggregation caused by arachidonic acid but not that triggered by ADP, collagen, or ristocetin. Additionally, it facilitates the dilation of constricted bovine coronary arteries (ED50= 1.1 µM) and blocks VEGF-driven tubulogenesis in human microvascular endothelial cells (HMVECs).