Docosapentaenoic acid 22n-3
(Synonyms: 二十二碳五烯酸) 目录号 : GC31637
Docosapentaenoic acid 22n-3 (n-3 DPA)是EPA的延长代谢产物，是二十碳五烯酸（EPA）和二十二碳六烯酸（DHA）之间的中间产物。
Cas No.:24880-45-3
Sample solution is provided at 25 µL, 10mM.
Docosapentaenoic acid 22n-3 (n-3 DPA) is an elongated metabolite of EPA and is an intermediary product between eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA)[1]. Docosapentaenoic acid 22n-3 is effective in the inhibition of aggregation in platelets and possesses greater endothelial cell migration ability than EPA. Docosapentaenoic acid 22n-3 also reduces the fatty acid synthase and malic enzyme activity levels, meanwhile having a role in attenuating age-related decrease in spatial learning and long-term potentiation[2].
In vitro experiments show Docosapentaenoic acid 22n-3 down-regulates the expression of genes involved in fat synthesis in liver cells (FAO cells; 50μM; 48h)[3]. Docosapentaenoic acid 22n-3 also acts as a potent stimulator of primary human endothelial cell migration (5mg/ml; 2 days)[4]. Moreover, docosapentaenoic acid 22n-3 decrease adrenal microsomal CYP21 activity and inhibit CYP17 activity (100μM; 10min)[5].
In vivo study shows that short-term Docosapentaenoic acid 22n-3 supplementation increases tissue docosapentaenoic acid, DHA, and EPA concentrations in male weanling Sprague–Dawley rats (50mg with food; 7d)[6]. Docosapentaenoic acid 22n-3 also decreased the hepatic TG levels compared to the control while EPA was most effective in reducing serum Triglycerides (TG) levels in C57BL/KsJ-db/db mice and C57BL/6J mice (1% [w/w] of trilinoleate in the control diet was replaced with n-3 DPA; 4 weeks)[7]. Docosapentaenoic acid 22n-3 exerts a protective effect in the hippocampus of the aged rat (200 mg/kg/day in laboratory chow; 56 days)[8].
References:
[1] Drouin, Gaetan et al. “The n-3 docosapentaenoic acid (DPA): A new player in the n-3 long chain polyunsaturated fatty acid family.” *Biochimie* vol. 159 (2019): 36-48. doi:10.1016/j.biochi.2019.01.022
[2] Kaur, Gunveen et al. “Docosapentaenoic acid (22:5n-3): a review of its biological effects.” *Progress in lipid research* vol. 50,1 (2011): 28-34. doi:10.1016/j.plipres.2010.07.004
[3] Kaur, Gunveen et al. “Docosapentaenoic acid (22:5n-3) down-regulates the expression of genes involved in fat synthesis in liver cells.” *Prostaglandins, leukotrienes, and essential fatty acids* vol. 85,3-4 (2011): 155-61. doi:10.1016/j.plefa.2011.06.002
[4] Kanayasu-Toyoda, T et al. “Docosapentaenoic acid (22:5, n-3), an elongation metabolite of eicosapentaenoic acid (20:5, n-3), is a potent stimulator of endothelial cell migration on pretreatment in vitro.” *Prostaglandins, leukotrienes, and essential fatty acids* vol. 54,5 (1996): 319-25. doi:10.1016/s0952-3278(96)90045-9
[5] Xie, Xuemei et al. “Effect of n-3 and n-6 Polyunsaturated Fatty Acids on Microsomal P450 Steroidogenic Enzyme Activities and In Vitro Cortisol Production in Adrenal Tissue From Yorkshire Boars.” *Endocrinology* vol. 157,4 (2016): 1512-21. doi:10.1210/en.2015-1831
[6] Kaur, Gunveen et al. “Short-term docosapentaenoic acid (22:5 n-3) supplementation increases tissue docosapentaenoic acid, DHA and EPA concentrations in rats.” *The British journal of nutrition* vol. 103,1 (2010): 32-7. doi:10.1017/S0007114509991334
[7] Gotoh, Naohiro et al. “Effects of three different highly purified n-3 series highly unsaturated fatty acids on lipid metabolism in C57BL/KsJ-db/db mice.” *Journal of agricultural and food chemistry* vol. 57,22 (2009): 11047-54. doi:10.1021/jf9026553
Kelly, Laura et al. “The polyunsaturated fatty acids, EPA and DPA exert a protective effect in the hippocampus of the aged rat.” *Neurobiology of aging*vol. 32,12 (2011): 2318.e1-15. doi:10.1016/j.neurobiolaging.2010.04.001
Docosapentaenoic acid 22n-3 (n-3 DPA)是EPA的延长代谢产物，是二十碳五烯酸（EPA）和二十二碳六烯酸（DHA）之间的中间产物[1]。n- 3dpa能有效抑制血小板聚集，具有比EPA更强的内皮细胞迁移能力。Docosapentaenoic acid 22n-3还能降低脂肪酸合成酶和苹果酸酶的活性水平，同时对空间学习和长时程增强bb0的年龄相关性下降有一定的缓解作用[2]。
体外实验显示，Docosapentaenoic acid 22n-3可下调肝细胞（FAO细胞; 50μM; 48h）脂肪合成相关基因的表达[3]。Docosapentaenoic acid 22n-3还可以作为原代人内皮细胞迁移的有效刺激物（5mg/ml; 2天）[4]。此外，docosapentaenoic acid 22n-3降低肾上腺微粒体CYP21活性，抑制CYP17活性（100μM; 10min）[5]。
体内研究表明，短期补充Docosapentaenoic acid 22n-3可提高雄性断奶大鼠 (50mg; 随食; 7d) 组织中二十二碳五烯酸、DHA和EPA的浓度[6]。与对照组相比，Docosapentaenoic acid 22n-3也降低了C57BL/KsJ-db/db小鼠和C57BL/6J小鼠中肝脏甘油三酯（TG）水平，而EPA在降低血清TG水平方面最为有效（; n- 3dpa替代对照组饲粮中1% [w/w]的三叶油酸; 4周）[7]。Docosapentaenoic acid 22n-3对老龄大鼠海马具有保护作用（200mg/kg/d; 56d）[8]。
| Cell experiment [1]: | |
Cell lines | FAO cells |
Preparation Method | FAO cells were treated with 50μM of EPA, DPA or DHA for 48h. 50μM OA was used as an unsaturated fatty acid control while ethanol (EC) (0.5%) was used as a vehicle control. Treatments were replenished after 24h. |
Reaction Conditions | 50μM, 48h |
Applications | Docosapentaenoic acid 22n-3 (50μM) incubation for 48h (like EPA and DHA) caused a significant decrease in the mRNA expression levels of SREBP-1c, 3-Hydroxy-3-Methyl-Glutaryl-Coenzyme A reductase (HMG-CoA reductase), Acetyl Coenzyme A Carboxylase (ACC-1) and Fatty Acid Synthase (FASn) compared with Oleic Acid (OA) and also a decrease in the protein levels of SREBP-1 and ACC-1. A time-course fatty acid analysis showed that Docosapentaenoic acid 22n-3 and EPA are interconvertable in the cells; however, after 8h of incubation with Docosapentaenoic acid 22n-3, the cell phospholipids contained mainly Docosapentaenoic acid 22n-3. |
| Animal experiment [2]: | |
Animal models | young (3–4 months) and aged (20–22 months) rats |
Preparation Method | rats treated with fatty acids received laboratory chow supplemented with either EPA or Docosapentaenoic acid 22n-3 (200mg/kg/day) and control rats received laboratory chow to which monounsaturated fatty acid was added to ensure isocaloric intake. The EPA preparation was 20:5n-3 ethyl-eicosapentaenoic acid (95% pure) to which 0.2% dl-tocopherol was added and the DPA preparation was Docosapentaenoic acid 22n-3. Food intake was measured for 1 week before the beginning of the experimental treatment to determine daily food intake and rats received their full daily allowance of freshly prepared chow each day. |
Dosage form | 200mg/kg/day in laboratory chow; 56 days |
Applications | Docosapentaenoic acid possesses neurorestorative effects and is capable of downregulating microglial activation. It also decreases the coupled activation of sphingomyelinase and caspase-3. |
References: | |
| Cas No. | 24880-45-3 | SDF | |
| 别名 | 二十二碳五烯酸 | ||
| Canonical SMILES | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(O)=O | ||
| 分子式 | C22H34O2 | 分子量 | 330.5 |
| 溶解度 | 0.1 M Na2CO3: 1.7 mg/ml,DMF: >100 mg/ml,DMSO: >100 mg/ml,Ethanol: Miscible | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.0257 mL | 15.1286 mL | 30.2572 mL |
| 5 mM | 0.6051 mL | 3.0257 mL | 6.0514 mL |
| 10 mM | 0.3026 mL | 1.5129 mL | 3.0257 mL |
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动物平均体重 | g | |
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动物数量 | 只 |
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