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Functions and Applications of Arachidonic Acid

Time:2024-05-13 Hits:68
Arachidonic acid (CAS: 506-32-1), referred to as all-cis-5,8,11,14-eicosatetraenoic acid, stands as a crucial omega-6 polyunsaturated fatty acid. Serving as a pivotal constituent of cell membranes, it is indispensable for membrane fluidity and flexibility, thereby exerting a central influence on various cellular functions. Its significance is particularly pronounced in the nervous system, skeletal muscle, and immune system. Arachidonic acid can be acquired directly from dietary sources like poultry and animal offal or synthesized from linoleic acid, a plant-derived essential fatty acid, undergoing desaturation and chain elongation processes to ultimately yield arachidonic acid.
 
With a broad spectrum of physiological impacts, arachidonic acid regulates ion channels, receptor activities, and enzyme functions. It also confers protective effects on the normal operations of the brain and muscles while demonstrating efficacy against certain parasitic infections and tumor progression. Notably, endocannabinoids, derived from arachidonic acid, play pivotal roles in brain function, mood modulation, pain perception, and energy equilibrium.
 
Arachidonic acid and its metabolites foster type 2 immune responses crucial for safeguarding against parasites and allergens. They accomplish this by influencing immune cells such as eosinophils and mast cells, and engaging with specific receptors on innate lymphoid cells.
 
Product
CAS
Level
Purity
Packaging
Arachidonic acid
506-32-1
Food Grade
98%
1kg 25kg
 
 
Physical and Chemical Characteristics

Chemical formula: C20H32O2
Molecular weight: 304.467
Appearance: white to light yellow
Density: 0.922 g/cm³
Melting point: -49
Boiling point: 407.5
Solubility:  Arachidonic acid dissolves in stuff like ethanol, acetone, and benzene, but not in water.
 
Physiological

Cell Membrane Structure and Function:
The four cis double bonds in ARA contribute to the fluidity and selective permeability of the cell membrane. These properties are essential for various cellular processes including cell signaling, membrane protein function, maintaining organelle integrity, and regulating vascular permeability. ARA also plays a significant role in neuronal function and brain plasticity.
 
Ion Channel Regulation:
ARA directly interacts with voltage-gated ion channels such as sodium (Nav), potassium (Kv), and proton (Hv) channels. This interaction affects neuronal excitability and synaptic transmission, thereby regulating electrical activity in the nervous system. ARA can modulate the activity of different types of potassium channels, influencing nerve impulses, muscle contraction, and hormone secretion.
 
Receptor and Enzyme Activity:
ARA regulates the activity of gamma-aminobutyric acid (GABA) receptors and affects the function of GABA-gated ion channels, impacting neurotransmission. It also inhibits nicotinic acetylcholine receptors, further modulating neuronal signaling. Additionally, ARA activates the NADPH oxidase complex, leading to the generation of reactive oxygen species (ROS) which can influence immune cell function.
 
Inflammation and Immune Regulation:
ARA and its metabolites, such as lipoxin A4, possess anti-inflammatory properties and regulate the expression of immune cytokines. They promote wound healing, combat potential diabetes-related issues, and are involved in type 2 immune responses. ARA also affects the recruitment and activation of immune cells, thereby playing a crucial role in inflammation and immune regulation.
 
Cell Death and Cancer:
ARA demonstrates potential anti-tumor activity by inducing lipid peroxidation in cell membranes and activating specific signaling pathways. It exhibits cytotoxic effects on various cancer cell lines while also participating in the apoptosis of normal cells. Moreover, ARA influences the activity of cancer-related enzymes like neutral sphingomyelinase activator (SMase), thus impeding tumor cell proliferation.
 
Nervous System and Development:
ARA plays a vital role in the development of infant nerves and the retina, impacting cognitive and visual functions. Often included in infant formula as a nutritional supplement, ARA, along with DHA, constitutes 20% of brain weight, influencing muscle growth during and after activities. ARA is associated with motor function, and supplementation proves beneficial for strength training.
 
Metabolism and Exercise:
ARA is present in muscles and affects muscle adaptation and output following exercise, thereby influencing sports performance. Experimental studies on rats have indicated that ARA can enhance muscle function.
 
Parasitic Diseases:
ARA exhibits anti-parasitic properties by activating specific enzymes, disrupting the surface membrane of parasites, and facilitating their demise.
 
 
Functional Food Industry Applications
 
Arachidonic Acid in Infant Formula
Arachidonic acid (ARA) serves as a vital nutritional enhancer in infant formula, widely utilized across regions like the United States, Canada, the European Union, Australia, New Zealand, Japan, and South Korea. Legislation in these areas supports its inclusion in powdered milk, emphasizing its safety and significance. Research underscores ARA's crucial role as a fatty acid essential for organ development, particularly the brain and nervous system. Both the European Union and the US FDA approved its incorporation as a food ingredient as early as 2008.
 
ARA's Role in Breast Milk
Breastfeeding stands as the optimal feeding method for infants due to its unparalleled nutritional composition. Human milk lipids, notably long-chain polyunsaturated fatty acids (LC-PUFAs) like arachidonic acid (ARA) and docosahexaenoic acid (DHA), are paramount. ARA, although relatively low in concentration and mainly present in triglyceride form, is pivotal in human milk. Its levels vary globally and regionally, influenced by maternal diet. ARA is indispensable for early infant development, with genetic variations in fatty acid metabolizing enzymes potentially impacting ARA and other LC-PUFA levels. Well-nourished mothers typically provide sufficient ARA and DHA through breast milk, necessitating appropriate supplementation of ARA and DHA in formula milk.
 
Necessity of Arachidonic Acid and DHA in Infant Formula
The European Academy of Pediatrics and the Child Health Foundation advocate for the inclusion of both DHA and ARA in infant and follow-on formulas. Recommendations suggest DHA content matching or exceeding the global average level in breast milk (0.3% of fatty acids), ideally reaching 0.5% of fatty acids. Although the optimal ARA intake remains undetermined, it should be provided alongside DHA. In formulations with DHA levels up to approximately 0.64%, ARA should be present in at least equivalent amounts. Further research is warranted to ascertain the optimal intake for infants across different developmental stages.
 
 
Toxicological Assessment of Oils High in Arachidonic Acid (ARA) and Docosahexaenoic Acid (DHA)
Looked into the safety of two important oils rich in polyunsaturated fatty acids: DHA-rich Schizochytrium oil and ARA-rich Mortierella alpina oil. These oils are commonly used in products like infant formula. The assessment included tests for genotoxicity and feeding trials with rats. The findings revealed that neither the DHA oil nor the ARA oil showed genotoxicity or adverse effects on animals at doses up to 5000 mg/kg. Any increase in cholesterol and triglycerides was deemed normal physiological responses. The study identified 5000 mg/kg as the dose with no observed adverse effects, indicating that the safety profile of these oils is comparable to other edible oils. This supports their safe use in food and alleviates specific toxicological concerns.
 
 
Applications in the Pharmaceutical Industry
 
Comparing the Anti-Cancer Effects of Arachidonic Acid (ARA) and Docosahexaenoic Acid (DHA) in Colorectal Cancer Cells
 
In vitro experiments were conducted to compare how arachidonic acid (ARA) and docosahexaenoic acid (DHA) affect the growth of colorectal cancer cells. The results demonstrated that DHA outperformed ARA in inhibiting the proliferation of HT-29 colorectal cancer cells. This effect was primarily achieved by downregulating proteasome particles. Conversely, ARA impacted all six DNA replication helicase particles. These findings imply that both DHA and ARA hold promise as potential candidates for chemopreventive agents.
 
Arachidonic Acid Improves Lipopolysaccharide-Induced Lung Injury in Mice
Researchers explored the effects of deuterated arachidonic acid (D-ARA) on lipopolysaccharide (LPS)-induced lung injury in mice. The results indicated that oral administration of D-ARA effectively mitigated the adverse effects of LPS on alveolar septal thickness and bronchoalveolar area, thereby preventing LPS-induced pathologies. This discovery opens up new therapeutic possibilities for reducing lung damage associated with severe infections and other pathological conditions.
 
Arachidonic Acid's Link to Heart Failure
Arachidonic acid and its metabolites are pivotal in predicting outcomes for heart failure patients. An AA score has been devised, accurately forecasting the risk of death within a year. A heightened ratio of the arachidonic acid metabolite 14,15-DHET/14,15-EET is strongly correlated with one-year mortality. This AA score outperforms existing biomarkers and clinical assessments. Studies suggest that targeting soluble epoxide hydrolase (sEH) inhibition may offer a novel avenue for heart failure treatment.
 
The Role of Arachidonic Acid in Intestinal Immunity
Arachidonic acid, released by phospholipase A2 and transformed into eicosanoic acid, influences intestinal innate immunity. It regulates immune cell development, differentiation, and the integrity of the intestinal epithelial barrier. These findings indicate that ARA and its derivatives not only participate in inflammation but also maintain intestinal immune equilibrium.
 
Arachidonic Acid Remodeling in Mouse Macrophages
During phagocytosis in mouse peritoneal macrophages, arachidonic acid responds to various stimuli by undergoing remodeling through CoA-independent transacylase. This process impacts cellular eicosanoid biosynthesis, demonstrating that the metabolic dynamics of arachidonic acid play a receptor-dependent regulatory role in immune cell function.
 
Long-Term Effects of Arachidonic Acid and DHA as Neuroprotective Nutrients
The critical roles of arachidonic acid and DHA in neurogenesis and brain development are highlighted. These long-chain polyunsaturated fatty acids are indispensable for signaling pathways, gene expression, and cell membrane function. In neurodegenerative conditions like Alzheimer's disease, arachidonic acid and DHA exhibit neuroprotective potential.
 
Oxidative Degradation of Arachidonic Acid in the Brains of Alzheimer's Disease Mice
Using radiolabeled arachidonic acid to study its fate in the brains of Alzheimer's transgenic mice revealed heightened degradation in amyloid plaque-rich regions, suggesting oxidative stress's involvement in disease progression mechanisms.
 
Effects of ARA Supplementation on Adipocyte Inflammation in Obese Mice
While ARA supplementation didn't alter the body weight or fat deposition in obese mice, it notably reduced the expression of inflammatory markers and the COX pathway in adipocytes. This suggests that metabolizing ARA through the LOX pathway may be beneficial for regulating inflammation.
 
Arachidonic Acid's Role in Depression
The potential role of arachidonic acid in depression is explored, including its function as an endogenous antiviral compound and its connection to depression treatment medications. It's hypothesized that arachidonic acid released by astrocytes and mast cells might be linked to depressive states.
 
 
Feed Industry Application
 
Arachidonic acid is a crucial nutrient for maintaining the normal physiological functions of fish. Research indicates that an adequate amount of arachidonic acid not only fosters fish growth and development but also enhances their survival rate and the quality of species. It's particularly vital to supplement juvenile fish with arachidonic acid during early stages. Some studies suggest that feed concentrations of 0.5% to 1% arachidonic acid yield the most significant growth and survival rate improvements in fish. Arachidonic acid deficiency may result in issues like slow growth, low body weight, and diminished fish yield.
 
Study on the Sensitivity of Fish Intestine to Arachidonic Acid
Through feeding trials with redfin pufferfish, the impacts of varying levels of arachidonic acid (ARA) on intestinal mucosal barriers and bacterial flora were investigated. Findings revealed that elevated ARA levels in feed compromised intestinal epithelial cell integrity and increased leukocyte infiltration in the lamina propria. Moreover, ARA influenced the gene expression of intestinal tight junction proteins and inflammatory factors, altering the intestinal flora structure.
 
Effects of Arachidonic Acid on Chinese Mitten Crab
Research delved into the impact of dietary arachidonic acid (ARA) on Chinese mitten crab, focusing on its antioxidant capacity, immune response, and intestinal health. Results revealed that appropriate ARA supplementation bolstered the antioxidant enzyme activity in crabs and influenced the expression of antibacterial genes. Moreover, ARA downregulated the expression of inflammatory factors and altered the composition of intestinal microbiota.
 
Improvement of Growth and Immunity of Juvenile Turbot by Arachidonic Acid
Exploration into the effects of adding arachidonic acid (ARA) to the diet of juvenile turbot fish primarily fed plant protein was conducted. ARA supplementation enhanced the growth performance of juvenile fish and mitigated intestinal inflammation induced by a plant protein diet. Additionally, ARA regulated the expression of anti-inflammatory cytokines, indicating its potential in reducing inflammation.
 
Effect of Arachidonic Acid on Reproduction of Black Sea Urchin
This study investigated the influence of varied levels of arachidonic acid (ARA) on the final maturation, spawning performance, and gonadal composition of black sea urchins. Adequate ARA supplementation supported the final maturation and reproductive capacity of black sea urchins, though excessive ARA levels might adversely affect their growth and reproduction.
 
 
Agricultural Applications
 
Alleviation of Chilling Injury of Cold-Stored Banana Fruits by ARA Treatment
The study examined the efficacy of exogenous ARA treatment combined with temperature regulation in mitigating chilling injury in refrigerated banana fruit. Findings indicated that this treatment reduced chilling injury symptoms, preserved fruit texture and nutrients, and bolstered the antioxidant defense system.
 
 
References
 
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