Docosahexaenoic Acid (DHA)
(Synonyms: 二十二碳六烯酸; DHA; Cervonic acid) 目录号 : GC30765
二十二碳六烯酸 (DHA) 是一种长链多不饱和脂肪酸，对婴儿和成人均有活性。
Cas No.:6217-54-5
Sample solution is provided at 25 µL, 10mM.
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- Purity: >98.00%
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| Cell experiment [1]: | |
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Cell lines |
HT-29, HCT116 and SW480 colon cancer cells |
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Preparation Method |
HT-29, HCT116 and SW480 colon cancer cells were exposed to Docosahexaenoic acid (DHA) (10-30 µM) for 48 h, and apoptosis was morphologically evaluated after acridine-orange staining. |
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Reaction Conditions |
10-30 µM for 48 hours |
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Applications |
A much larger fraction of SW480 cells (about 60% with 30 µM DHA) underwent DHA-induced apoptosis than the HCT116 or HT-29 cells (about 15-18% with 30 µM DHA), and that was related to the greater basal propensity for apoptosis of the SW480 cells. |
| Animal experiment [2]: | |
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Animal models |
Adult CD1 mice (male, 25-35 g) |
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Preparation Method |
Muscles were disassociated following an incision on the left hind paw. A 0.38-mm stainless steel pin was inserted into the tibia intramedullary canal, followed by the osteotomy. The incision was sutured with 6-0 Prolene. For perioperative treatment, Docosahexaenoic acid (500 µg, 100 µl) or SPMs (500 ng, 100 µl) were dissolved in 2% ethanol as vehicle and administered intravenously through tail vein injection at 10 min and 24 h after surgery. |
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Dosage form |
500 µg, 100 µl, iv. |
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Applications |
Intravenous injections of DHA (500 µg, 100 µl) significantly attenuated mechanical allodynia by decreasing paw withdrawal frequency. Compared to vehicle control, cold allodynia was not significantly reduced by DHA. Cold allodynia in the treatment group was also not significantly different from sham surgery, suggesting a possible inhibition of cold allodynia by the DHA pre-treatment. |
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References: [1] : Fasano E, Serini S, Piccioni E, et al. DHA induces apoptosis by altering the expression and cellular location of GRP78 in colon cancer cell lines[J]. Biochimica et Biophysica Acta (BBA)-Molecular Basis of Disease, 2012, 1822(11): 1762-1772. [2] : Zhang L, Terrando N, Xu Z Z, et al. Distinct analgesic actions of DHA and DHA-derived specialized pro-resolving mediators on post-operative pain after bone fracture in mice[J]. Frontiers in pharmacology, 2018, 9: 412. |
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Docosahexaenoic acid (DHA) is a long-chain polyunsaturated fatty acid with activities in both infants and adults [1]. Docosahexaenoic acid (DHA) is a structural constituent of membranes specifically in the central nervous system. Data from cell and animal studies justify the indication of DHA in relation to brain function for neuronal cell growth and differentiation as well as in relation to neuronal signaling [2].
Docosahexaenoic acid (10-30 μM 48 h) treatment induced apoptosis in three colon cancer cell lines (HT-29, HCT116 and SW480), and inhibited their total and surface GRP78 expression. The cell ability to undergo DHA-induced apoptosis was inversely related to their level of GRP78 expression [3]. Doxorubicin chemosensitization of breast cancer cell lines by docosahexaenoic acid was cell-line selective, affecting MDA-MB-231 and MCF-7dox (a doxorubicin-resistant cell line) but not the parental MCF-7 cell line [4].
Intravenous perioperative treatment with DHA (500 μg), resolvin D1 (RvD1, 500 ng) and maresin 1 (MaR1, 500 ng), 10 min and 24 h after the surgery, delayed the development of fPOP (mechanical allodynia and cold allodynia) in a mouse model of post-operative pain induced by tibial bone fracture [5]. Oral administration of DHA to normal adult mice as lysophosphatidylcholine (LPC) (40 mg DHA/kg) for 30 days increased DHA content of the brain by >2-fold. In contrast, the same amount of free DHA did not increase brain DHA, but increased the DHA in adipose tissue and heart [6]. Supplementation of the high-fat diet with either EPA, DPA or DHA prevented the fatty liver, prevented high serum cholesterol and serum glucose and prevented high liver cholesterol levels [7].
References:
[1]. Lien E L. Toxicology and safety of DHA[J]. Prostaglandins, leukotrienes and essential fatty acids, 2009, 81(2-3): 125-132.
[2]. Lauritzen L, Brambilla P, Mazzocchi A, et al. DHA effects in brain development and function[J]. Nutrients, 2016, 8(1): 6.
[3]. Fasano E, Serini S, Piccioni E, et al. DHA induces apoptosis by altering the expression and cellular location of GRP78 in colon cancer cell lines[J]. Biochimica et Biophysica Acta (BBA)-Molecular Basis of Disease, 2012, 1822(11): 1762-1772.
[4]. Maheo K, Vibet S, Steghens J P, et al. Differential sensitization of cancer cells to doxorubicin by DHA: a role for lipoperoxidation[J]. Free Radical Biology and Medicine, 2005, 39(6): 742-751.
[5]. Zhang L, Terrando N, Xu Z Z, et al. Distinct analgesic actions of DHA and DHA-derived specialized pro-resolving mediators on post-operative pain after bone fracture in mice[J]. Frontiers in pharmacology, 2018, 9: 412.
[6]. Sugasini D, Thomas R, Yalagala P C R, et al. Dietary docosahexaenoic acid (DHA) as lysophosphatidylcholine, but not as free acid, enriches brain DHA and improves memory in adult mice[J]. Scientific Reports, 2017, 7(1): 1-11.
[7]. Guo X, Sinclair A J, Kaur G, et al. Differential effects of EPA, DPA and DHA on cardio-metabolic risk factors in high-fat diet fed mice[J]. Prostaglandins, Leukotrienes and Essential Fatty Acids, 2018, 136: 47-55.
二十二碳六烯酸 (DHA) 是一种长链多不饱和脂肪酸,对婴儿和成人均有活性[1]。二十二碳六烯酸 (DHA) 是膜的结构成分,特别是在中枢神经系统中。来自细胞和动物研究的数据证明,DHA 与神经元细胞生长和分化的大脑功能以及神经元信号转导有关 [2]。
二十二碳六烯酸（10-30 μM,48 小时）处理可诱导三种结肠癌细胞系（HT-29、HCT116 和 SW480）发生细胞凋亡,并抑制它们的总 GRP78 表达和表面 GRP78 表达。细胞经历 DHA 诱导的细胞凋亡的能力与其 GRP78 表达水平呈负相关[3]。二十二碳六烯酸对乳腺癌细胞系的多柔比星化学增敏具有细胞系选择性,影响 MDA-MB-231 和 MCF-7dox（多柔比星耐药细胞系）,但不影响亲代 MCF-7 细胞系 [4].
在手术后 10 分钟和 24 小时使用 DHA（500 μg）、resolvin D1（RvD1,500 ng）和 maresin 1（MaR1,500 ng）进行围手术期静脉内治疗,延缓了 fPOP（机械异常性疼痛和寒冷）的发展异常性疼痛）在胫骨骨折术后疼痛小鼠模型中的作用[5]。给正常成年小鼠口服 DHA 作为溶血磷脂酰胆碱 (LPC) (40 mg DHA/kg) 30 天后,大脑中的 DHA 含量增加了 >2 倍。相比之下,等量的游离 DHA 并没有增加大脑中的 DHA,而是增加了脂肪组织和心脏中的 DHA [6]。在高脂肪饮食中补充 EPA、DPA 或 DHA 可预防脂肪肝,预防高血清胆固醇和高血糖,并预防高肝胆固醇水平[7]。
| Cas No. | 6217-54-5 | SDF | |
| 别名 | 二十二碳六烯酸; DHA; Cervonic acid | ||
| Canonical SMILES | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(O)=O | ||
| 分子式 | C22H32O2 | 分子量 | 328.49 |
| 溶解度 | Ethanol : 50 mg/mL (152.21 mM);DMSO : 5.2 mg/mL (15.83 mM);Water : < 0.1 mg/mL (insoluble) | 储存条件 | Store at -20°C, protect from light, stored under nitrogen |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 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℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.0442 mL | 15.2212 mL | 30.4423 mL |
| 5 mM | 0.6088 mL | 3.0442 mL | 6.0885 mL |
| 10 mM | 0.3044 mL | 1.5221 mL | 3.0442 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Health benefits of docosahexaenoic acid (DHA)
Docosahexaenoic acid (DHA) is essential for the growth and functional development of the brain in infants. DHA is also required for maintenance of normal brain function in adults. The inclusion of plentiful DHA in the diet improves learning ability, whereas deficiencies of DHA are associated with deficits in learning. DHA is taken up by the brain in preference to other fatty acids. The turnover of DHA in the brain is very fast, more so than is generally realized. The visual acuity of healthy, full-term, formula-fed infants is increased when their formula includes DHA. During the last 50 years, many infants have been fed formula diets lacking DHA and other omega-3 fatty acids. DHA deficiencies are associated with foetal alcohol syndrome, attention deficit hyperactivity disorder, cystic fibrosis, phenylketonuria, unipolar depression, aggressive hostility, and adrenoleukodystrophy. Decreases in DHA in the brain are associated with cognitive decline during aging and with onset of sporadic Alzheimer disease. The leading cause of death in western nations is cardiovascular disease. Epidemiological studies have shown a strong correlation between fish consumption and reduction in sudden death from myocardial infarction. The reduction is approximately 50% with 200 mg day(-1)of DHA from fish. DHA is the active component in fish. Not only does fish oil reduce triglycerides in the blood and decrease thrombosis, but it also prevents cardiac arrhythmias. The association of DHA deficiency with depression is the reason for the robust positive correlation between depression and myocardial infarction. Patients with cardiovascular disease or Type II diabetes are often advised to adopt a low-fat diet with a high proportion of carbohydrate. A study with women shows that this type of diet increases plasma triglycerides and the severity of Type II diabetes and coronary heart disease. DHA is present in fatty fish (salmon, tuna, mackerel) and mother's milk. DHA is present at low levels in meat and eggs, but is not usually present in infant formulas. EPA, another long-chain n-3 fatty acid, is also present in fatty fish. The shorter chain n-3 fatty acid, alpha-linolenic acid, is not converted very well to DHA in man. These longchain n-3 fatty acids (also known as omega-3 fatty acids) are now becoming available in some foods, especially infant formula and eggs in Europe and Japan. Fish oil decreases the proliferation of tumour cells, whereas arachidonic acid, a longchain n-6 fatty acid, increases their proliferation. These opposite effects are also seen with inflammation, particularly with rheumatoid arthritis, and with asthma. DHA has a positive effect on diseases such as hypertension, arthritis, atherosclerosis, depression, adult-onset diabetes mellitus, myocardial infarction, thrombosis, and some cancers.
Docosahexaenoic acid (DHA): An essential nutrient and a nutraceutical for brain health and diseases
Docosahexaenoic acid (DHA), a polyunsaturated fatty acid (PUFA) enriched in phospholipids in the brain and retina, is known to play multi-functional roles in brain health and diseases. While arachidonic acid (AA) is released from membrane phospholipids by cytosolic phospholipase A2 (cPLA2), DHA is linked to action of the Ca2+-independent iPLA2. DHA undergoes enzymatic conversion by 15-lipoxygenase (Alox 15) to form oxylipins including resolvins and neuroprotectins, which are powerful lipid mediators. DHA can also undergo non-enzymatic conversion by reacting with oxygen free radicals (ROS), which cause the production of 4-hydoxyhexenal (4-HHE), an aldehyde derivative which can form adducts with DNA, proteins and lipids. In studies with both animal models and humans, there is evidence that inadequate intake of maternal n-3 PUFA may lead to aberrant development and function of the central nervous system (CNS). What is less certain is whether consumption of n-3 PUFA is important in maintaining brain health throughout one's life span. Evidence mostly from non-human studies suggests that DHA intake above normal nutritional requirements might modify the risk/course of a number of diseases of the brain. This concept has fueled much of the present interest in DHA research, in particular, in attempts to delineate mechanisms whereby DHA may serve as a nutraceutical and confer neuroprotective effects. Current studies have revealed ability for the oxylipins to regulation of cell redox homeostasis through the Nuclear factor (erythroid-derived 2)-like 2/Antioxidant response element (Nrf2/ARE) anti-oxidant pathway, and impact signaling pathways associated with neurotransmitters, and modulation of neuronal functions involving brain-derived neurotropic factor (BDNF). This review is aimed at describing recent studies elaborating these mechanisms with special regard to aging and Alzheimer's disease, autism spectrum disorder, schizophrenia, traumatic brain injury, and stroke.
Docosahexaenoic acid (DHA). Monograph
Docosahexaenoic acid (DHA): an ancient nutrient for the modern human brain
Modern humans have evolved with a staple source of preformed docosahexaenoic acid (DHA) in the diet. An important turning point in human evolution was the discovery of high-quality, easily digested nutrients from coastal seafood and inland freshwater sources. Multi-generational exploitation of seafood by shore-based dwellers coincided with the rapid expansion of grey matter in the cerebral cortex, which characterizes the modern human brain. The DHA molecule has unique structural properties that appear to provide optimal conditions for a wide range of cell membrane functions. This has particular implications for grey matter, which is membrane-rich tissue. An important metabolic role for DHA has recently been identified as the precursor for resolvins and protectins. The rudimentary source of DHA is marine algae; therefore it is found concentrated in fish and marine oils. Unlike the photosynthetic cells in algae and higher plants, mammalian cells lack the specific enzymes required for the de novo synthesis of alpha-linolenic acid (ALA), the precursor for all omega-3 fatty acid syntheses. Endogenous synthesis of DHA from ALA in humans is much lower and more limited than previously assumed. The excessive consumption of omega-6 fatty acids in the modern Western diet further displaces DHA from membrane phospholipids. An emerging body of research is exploring a unique role for DHA in neurodevelopment and the prevention of neuropsychiatric and neurodegenerative disorders. DHA is increasingly being added back into the food supply as fish oil or algal oil supplementation.
Docosahexaenoic acid (DHA), a fundamental fatty acid for the brain: New dietary sources
Docosahexaenoic acid (C22: 6n-3, DHA) is a long-chain polyunsaturated fatty acid of marine origin fundamental for the formation and function of the nervous system, particularly the brain and the retina of humans. It has been proposed a remarkable role of DHA during human evolution, mainly on the growth and development of the brain. Currently, DHA is considered a critical nutrient during pregnancy and breastfeeding due their active participation in the development of the nervous system in early life. DHA and specifically one of its derivatives known as neuroprotectin D-1 (NPD-1), has neuroprotective properties against brain aging, neurodegenerative diseases and injury caused after brain ischemia-reperfusion episodes. This paper discusses the importance of DHA in the human brain given its relevance in the development of the tissue and as neuroprotective agent. It is also included a critical view about the ways to supply this noble fatty acid to the population.