Arachidonic acid

Manufactured by Nu-Chek Prep

Sourced in United States

Arachidonic acid is a long-chain polyunsaturated fatty acid found in the phospholipids of cell membranes. It is a precursor for the synthesis of eicosanoids, which are important signaling molecules involved in various physiological processes.

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14 protocols using arachidonic acid

Fatty Acid Extraction and Analysis

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Phytomonic acid (C18 CFA), palmitoleic acid (C16∶1), palmitic acid (C16∶0), oleic acid (C18∶1n9), and stearic acid (C18∶0) were obtained from Cayman Chemical (MI). Lauric acid (C12∶0), myristic acid (C14∶0), vaccenic acid (C18∶1n7), elaidic acid (trans-C18∶1n9), linoleic acid (C18∶2n6), arachidonic acid (C20∶4n6), and eicosapentaenoic acid (C20∶5n3) were from Nu-Chek Prep, Inc. (MN). All solvents were of GC-MS grade and all other reagents were of the highest grade available.

Kaul T.K., Reis Rodrigues P., Ogungbe I.V., Kapahi P, & Gill M.S. (2014). Bacterial Fatty Acids Enhance Recovery from the Dauer Larva in Caenorhabditis elegans. PLoS ONE, 9(1), e86979.

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Membrane Fluidity Measurement in Bacterial Mutants

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The WT and ∆fakA mutant strains were grown for 5 and 24 hours in 20 mL of TSB at 37 ℃ with shaking in Falcon tubes. Each strain was grown in the presence and absence of 20% human serum (vol/vol) or the fatty acid mix: oleic acid (18:1), linoleic acid (18:2), and arachidonic acid (20:4) (Nu-Chek Prep), each at a final concentration of 100 µM. Cultures were pelleted by centrifugation, washed, and resuspended in normal saline at a McFarland reading of 0.9. Cell membrane fluidity was measured by polarizing spectrofluorometry using a BioTek Synergy H1 plate reader (BioTek Instruments, Winooski, VT, USA) with the fluorescent probe 1,6-diphenyl-1,3,5-hexatriene.

Pruitt E.L., Zhang R., Ross D.H., Ashford N.K., Chen X., Alonzo F I.I.I., Bush M.F., Werth B.J, & Xu L. (2023). Elucidating the impact of bacterial lipases, human serum albumin, and FASII inhibition on the utilization of exogenous fatty acids by Staphylococcus aureus. mSphere, 8(6), e00368-23.

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Oxidative Stress Response in Bacterial Mutants

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The WT and ΔfakA mutant strain were grown to stationary phase in 7 mL of MHB50 at 37 °C with shaking for 24 hours in Falcon tubes. Both strains were grown in the presence and absence of the fatty acid mix: oleic acid (18:1), linoleic acid (18:2), and arachidonic acid (20:4) (Nu-Chek Prep, Inc., Elysian, MN), each at a final concentration of 100 μM. Cultures were pelleted by centrifugation, resuspended in 7 mL MHB50 containing the fluorogenic dye, 2’,7’-dichlorodihydrofluorescein diacetate (H₂DCFDA) at a concentration of 10 μM, and incubated for 45 minutes at 37°C protected from light. Cultures were pelleted by centrifugation, washed with saline, and resuspended in 7 mL of MHB50. Cells were added in triplicate to a black Nunc 96-well flat-bottom microplate in the presence or absence of the fatty acid mix with a final volume of 200 μL. Reactive oxygen species were measured by fluorescence readings (λ excitation=485 nm, λ emission=535 nm) using a BioTek Synergy H1 plate reader set at 37 °C for 8 hours.

Pruitt E.L., Zhang R., Ross D.H., Ashford N.K., Chen X., Alonzo F I.I.I., Bush M.F., Werth B.J, & Xu L. (2023). Elucidating the Impact of Bacterial Lipases, Human Serum Albumin, and FASII Inhibition on the Utilization of Exogenous Fatty Acids by Staphylococcus aureus. bioRxiv.

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Membrane Fluidity of Bacterial Mutants

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The WT and ΔfakA mutant strains were grown to mid-exponential and stationary phase in 5 mL of TSB at 37 °C with shaking in Falcon tubes. Each strain was grown in the presence and absence of 20% human serum (v/v) or the fatty acid mix: oleic acid (18:1), linoleic acid (18:2), and arachidonic acid (20:4) (Nu-Chek Prep, Inc., Elysian, MN), each at a final concentration of 100 μM. Cultures were pelleted by centrifugation, washed, and resuspended in normal saline at a McFarland reading of 0.9. Cell membrane fluidity was measured by polarizing spectrofluorometry using a BioTek Synergy H1 plate reader (BioTek Instruments, Winooski, VT) with the fluorescent probe, 1,6-diphenyl-1,3,5-hexatriene (DPH).

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COX-2 Enzymatic Activity Assay

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Arachidonic acid (90%+) was obtained from NuChek Prep. (Elysian, MN). Recombinant human COX-2 was expressed and purified as described (9 (link)). THP-1 cells were from ATCC (Manassas, VA).

Giménez-Bastida J.A., Suzuki T., Sprinkel K.C., Boeglin W.E, & Schneider C. (2016). Biomimetic synthesis of hemiketal eicosanoids for biological testing. Prostaglandins & other lipid mediators, 132, 41-46.

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Oxidative Stress Response in Bacteria

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The WT and ∆fakA mutant strains were grown in 7 mL of MHB50 at 37°C with shaking for 24 hours in Falcon tubes. Both strains were grown in the presence and absence of the fatty acid mix: oleic acid (18:1), linoleic acid (18:2), and arachidonic acid (20:4) (Nu-Chek Prep), each at a final concentration of 100 µM. Cultures were pelleted by centrifugation, resuspended in 7 mL of MHB50 containing the fluorogenic dye H₂DCFDA at a concentration of 10 µM, and incubated for 45 minutes at 37°C protected from light. Cultures were pelleted by centrifugation, washed with saline, and resuspended in 7 mL of MHB50. Cells were added in triplicate to a black Nunc 96-well flat-bottom microplate in the presence or absence of the fatty acid mix, with a final volume of 200 µL. Reactive oxygen species were measured by fluorescence readings (λ excitation = 485 nm, λ emission = 535 nm) using a BioTek Synergy H1 plate reader set at 37°C for 8 hours.

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Platelet Aggregation Assay Protocol

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Platelet aggregation was tested in citrated platelet-rich plasma (PRP) using 2.5 μM adenosine diphosphate (ADP; Calbiochem), 1 mM arachidonic acid (Nu Chek Prep), 1 μg/mL Horm equine tendon collagen (Nycomed, Pharma), 10 μM Thrombin Receptor Activating Peptide-14 (TRAP14-mer; Neosystem SA), 4 μM epinephrine (Sigma-Aldrich), and 5 μM ionophore 23187 (Calbiochem) in an APACT-4004 aggregometer (Elitech) according to standard procedures [13 ]. Native PRP concentration was adjusted if the platelet count was higher than 600G/L to reach a platelet count of 500 G/L.

Guy A., Helzy K., Mansier O., Bordet J.C., Rivière E., Fiore M, & James C. (2023). Platelet function studies in myeloproliferative neoplasms patients with Calreticulin or JAK2V617F mutation. Research and Practice in Thrombosis and Haemostasis, 7(2), 100060.

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Fatty Acid Sourcing for Research

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Hemin was purchased from Sigma (St. Louis, MO, USA) or Porphyrin Products (Logan, UT, USA). Tween 20 was from Anatrace (Maumee, OH, USA). Arachidonic acid, 11, 14-eicosadienoic acid, 8, 11, 14-eicosatrienoic acid and 5, 8, 11, 14, 17-eicosapentaenoic acid were purchased from Nu-Chek Prep, Inc. (Elysian, MN, USA). 5, 6, 8, 9, 11, 12, 14, 15-d₈-Arachidonic acid was from Sigma.

Wu G, & Tsai A.L. (2016). Dynamics of Radical Intermediates in Prostaglandin H Synthase-1 Cyclooxygenase Reactions is Modulated by Multiple Factors. Protein and peptide letters, 23(11), 1013-1023.

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Fatty Acid Analysis of Botanical Compounds

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TWM was obtained from Qianjin Xieli Pharmaceutical Co., Ltd (Hunan, China). TP (>98% pure) was provided by Guilin Sanjin Biologics Co., Ltd (Guanxi, China). Docosahexaenoic acid (C22:6n3), docosanoic acid (C22:0), eicosapentaenoic acid (C20:5n3), eicosatrienoic acid (C20:3n6), arachidonic acid (C20:4n6), arachidic acid (C20:0), nonadecadienoic acid (C19:2n6), γ-linolenic acid (C18:3n6), α-linolenic acid (C18:3n3), lin oleic acid (C18:2n6), oleic acid (C18:1n9), cis-vaccenic acid (C18:1n7), stearic acid (C18:0), palmitic acid (C16:0), palmitoleic acid (C16:1n7), myristic acid (C14:0) and lauric acid (C12:0) were purchased from Nu-Chek Prep (Elysian, MN, USA). Their purities were above 98%. Trimethylsilane diazomethane (TMSCHN₂) in n-hexane (2 mol/L) was purchased from Energy Chemical (Shanghai, China). The other chemical reagents were purchased from Xilong Scientific Co., Ltd (Guangdong, China).

Liu X., Hu C., Li H., Wu L., Xiong Y., Tang X, & Deng S. (2021). Metabolic profiling of fatty acids in Tripterygium wilfordii multiglucoside- and triptolide-induced liver-injured rats. Open Life Sciences, 16(1), 184-197.

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Arachidonic Acid Autoxidation Experiments

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The arachidonic acid used in these experiments was purchased from Nuchek Prep (Elysian, MN). Silica Gel 60 G (EM Reagents), listed as containing CaSO4 13%, Cl 0.02%, and Fe 0.02%, was placed in a covered Pyrex cell culture dish and oven dried overnight at 130°C for 24 h before use in the autoxidation experiments. Standards of EETs were prepared by epoxidation of arachidonic acid using an equivalent of meta-chloroperoxybenzoic acid in dichloromethane.

Weiny J.A., Boeglin W.E., Calcutt M.W., Stec D.F, & Brash A.R. (2021). Monolayer autoxidation of arachidonic acid to epoxyeicosatrienoic acids as a model of their potential formation in cell membranes. Journal of Lipid Research, 63(1), 100159.

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