Docosapentaenoic acid 22n-3

目录号: GC31637纯度: >98.00%同义词: 二十二碳五烯酸
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。

Docosapentaenoic acid 22n-3
Cas No.: 24880-45-3
规格价格库存数量操作
1mg¥758.00现货
1
5mg¥1,651.00现货
1

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产品描述 Description

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]

实验参考方法 Experimental Reference Method

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:
[1]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
[2]. 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

产品文档 Product Documents

Purity:>98.00%

化学性质Chemical Properties

CAS 号
24880-45-3
同义词
二十二碳五烯酸
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 g/mol
溶解性
0.1 M Na2CO3: 1.7 mg/ml,DMF: >100 mg/ml,DMSO: >100 mg/ml,Ethanol: Miscible
保存条件
Store at -20°C
General tips
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储备液的保存方式和期限:-80°C 储存时,请在 6 个月内使用,-20°C 储存时,请在 1 个月内使用。
为了提高溶解度,请将管子加热至 37°C,然后在超声波浴中震荡一段时间。
Shipping Condition
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