Dde-lysine was selectively deprotected by incubating the resin three times with 2% hydrazine hydrate in DMF for 3 min (400 r.p.m.), which also cleaved the Fmoc groups. Therefore, the N-terminus was protected by Boc in peptides not modified with fluorescein. Peptides were acylated at the lysine side chain by the addition of free fatty acid (2 equiv.), DCC (2 equiv.) and HOBt (4 equiv.) in 3 ml DMF and shaking at 400 r.p.m. for 1 h. Myristic acid, palmitic acid and stearic acid were purchased from Tokyo Chemical Industry (TCI).
Palmitic acid
Manufactured by Tokyo Chemical Industry
Sourced in Japan
Palmitic acid is a saturated fatty acid with the chemical formula CH3(CH2)14COOH. It is a white, waxy solid at room temperature and is commonly used as a precursor in the production of various chemical compounds.
Automatically generated - may contain errors
Lab products found in correlation
Myristic acid, by Tokyo Chemical Industry (6 mentions)
Stearic acid, by Tokyo Chemical Industry (6 mentions)
Lauric acid, by Tokyo Chemical Industry (4 mentions)
Oleic acid, by Merck Group (4 mentions)
Arachidic acid, by Tokyo Chemical Industry (2 mentions)
Capric acid, by Fujifilm (2 mentions)
Forskolin, by Bio-Techne (1 mentions)
Recombinant murine leptin, by Thermo Fisher Scientific (1 mentions)
Docosanoic acid, by Merck Group (1 mentions)
Decanoic acid, by Merck Group (1 mentions)
Tetracosanoic acid, by Merck Group (1 mentions)
Docosapentaenoic acid, by Merck Group (1 mentions)
Arachidic acid, by Merck Group (1 mentions)
9 decenoic acid, by Merck Group (1 mentions)
Perfluorooctanoic acid pfoa, by Merck Group (1 mentions)
Lc ms ms grade acetonitrile, by Merck Group (1 mentions)
Hplc grade hexane, by Merck Group (1 mentions)
Anti syntaxin, by Merck Group (1 mentions)
Anti akt, by Cell Signaling Technology (1 mentions)
Anti erk, by Cell Signaling Technology (1 mentions)
12 protocols using palmitic acid
1
Site-Specific Peptide Acylation
2
Rubber Compound Preparation with Fatty Acids
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Isoprene rubber (IR2200) was supplied from JSR Co, Japan. Natural rubber (NR, RSS no. 1) was used. Elemental sulfur (S8, purity: 99.9%, powder: 150 mesh), ZnO (average diameter: 0.29 μm), N-cyclohexyl-2-benzothiazole sulfenamide (CBS, Sanceler CM-G), and zinc stearate (ZnSt2) were rubber-processing commercial grade and used as received. They were purchased from Hosoi Chemical Industry Co., Ltd., Tokyo, Japan, Sakai Chemical Industry Co., Ltd., Osaka, Japan, Sanshin Chemical Industry Co., Ltd., Yamaguchi, Japan, and FUJIFILM Wako Pure Chemical Corporation., Osaka, Japan, respectively. Different kinds of saturated fatty acid, i.e., lauric acid (LaH, C12, purity: >98.0%), myristic acid (MyH, C14, purity: >99.0%), palmitic acid (PaH, C16, purity: >99.5%), and arachidic acid (ArH, C20, purity: >98.0%) were purchased from Tokyo Chemical Industry Co., Tokyo, Japan. Stearic acid (StH, C18, LUNAC S-25) was supplied from Kao Co., Tokyo, Japan. All fatty acids were used as received.
3
Peptide Synthesis and Compound Sourcing
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YHIEPV was synthesized by the F-moc strategy and purified by reversed-phase high-performance liquid chromatography (HPLC). Forskolin was obtained from Tocris Bioscience. Recombinant murine leptin was obtained from PEPROTECH. Palmitic acid was obtained from Tokyo Chemical Industry.
4
Fatty Acid Quantification by LC-MS/MS
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The following chemicals were purchased from Tokyo Chemical Industry (Tokyo, Japan): n-octanoic acid (C8:0), lauric acid (C12:0), myristic acid (C14:0), palmitic acid (C16:0), cis-9-hexadecenoic acid (C16:1), stearic acid (C18:0), γ-linolenic acid (C18:3), cis-5,8,11,14,17-eicosapentaenoic acid (EPA; C20:5) and arachidonic acid (C20:4). Decanoic acid (C10:0), 9-decenoic acid (C10:1), oleic acid (C18:1), arachidic acid (C20:0), all-cis-7,10,13,16,19-docosapentaenoic acid (DPA, C22:5), docosanoic acid (C22:0), tetracosanoic acid (C24:0), hexacosanoic acid (C26:0), DAABD-AE, N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC), 4-(dimethylamino) pyridine (DMAP) and perfluorooctanoic acid (PFOA) were purchased from Sigma-Aldrich (Taufkirchen, Germany). The following deuterium or 13C labeled analogs used as IS were purchased from Cambridge Isotopes Laboratories (Tewksbury, MA, USA): 13C4-C8:0, d3-C10:0, d3-C12:0, d3-C14:0, d4-C16:0 and d3-C18:0. PRA, PHA, d3-PRA, d3-PHA, d4-C22:0, d4-C24:0, and d4-C26:0 were obtained from Dr. H. J. Ten Brink (Vrije Universiteit Medical Center, Amsterdam, The Netherlands). LC-MS/MS grade acetonitrile and water were purchased from Merck (Darmstadt, Germany). Merck also supplied us with HPLC grade hexane, toluene, and heptane.
5
Lipid Signaling Modulators in Neuroinflammation
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BHB and sodium salts of capric acid, caprylic acid, LA, myristic acid, palmitic acid, and stearic acid were purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). Anti-ERK, anti-phosphorylated ERK (pERK), anti-Akt, anti-pAkt, anti-NFκB, anti-pNFκB, and U0126 were purchased from Cell Signaling Technology Inc. (Danvers, MA, USA). Anti- N-methyl-D-aspartate receptor type 2B (NR2B), anti-syntaxin, anti-β-actin, LPS (from Escherichia coli O111:B4), and poly-ethylenimine (PEI) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Cytarabine (AraC) was purchased from FUJIFILM-Wako Pure Chemical Corp. (Osaka, Japan). Anti-synaptophysin (Boehringer Mannheim GmbH, Mannheim, Germany) and anti-synaptosomal nerve-associated protein 25 (SNAP25) (Synaptic Systems, Germany) were also used in the study.
6
Preparation and Characterization of Soybean and Tempe Ethanol Fractions
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The spore suspension of R. oligosporus (a starter of ragi tempe, Raprima, Bandung, Indonesia) and tempe were prepared as described previously [11] . S. aureus NCTC50581 (National Collection of Type Cultures, London, UK) was cultured in Bacto tryptic soy broth (Becton, Dickinson and Company, Sparks, MD). B. subtilis ATCC6633 (American Type Culture Collection, Manassas, VA, USA) was cultured at 37ºC in Luria-Bertani medium (10 g/L tryptone, 5 g/L yeast extract, 10 g/L NaCl, pH 7.2). Oleic acid, linOleic acid, and α-linolenic acid were purchased from Sigma-Aldrich (Tokyo, Japan). Palmitic acid, stearic acid, and 1-monoolein were purchased from Tokyo Chemical Industry (Tokyo, Japan). 1-Monolinolein was purchased from AccuStandard (New Haven, CT, USA).
Preparation of the ethanol fractions from heat-processed soybean and tempe Soybean grains treated with steam pressure before or after fermentation were lyophilized and finely ground by a pestle and mortar. The ground powder was suspended in 2.5 mL ethanol/g dry wt. The suspension was vigorously agitated at 4°C for 8 h and centrifuged at 13,000 × g for 10 min. The supernatant was used as the ethanol fraction from soybean or tempe and stored at -20°C.
Preparation of the ethanol fractions from heat-processed soybean and tempe Soybean grains treated with steam pressure before or after fermentation were lyophilized and finely ground by a pestle and mortar. The ground powder was suspended in 2.5 mL ethanol/g dry wt. The suspension was vigorously agitated at 4°C for 8 h and centrifuged at 13,000 × g for 10 min. The supernatant was used as the ethanol fraction from soybean or tempe and stored at -20°C.
7
Bacterial Growth Inhibition Assay
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Lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, and glutaraldehyde were purchased from Tokyo Chemical Industry Co. Ltd. (Tokyo, Japan). Caprylic acid, capric acid, linoleic acid, SLS, sodium chloride (NaCl), disodium hydrogen phosphate 12-water (Na2HPO4•12H2O), potassium dihydrogen phosphate (KH2PO4), sodium chloride (KCl), potassium hydroxide (KOH), hydrochloric acid (HCl), manganese (II) chloride tetrahydrate (MnCl2•4H2O), magnesium sulfate heptahydrate (MgSO4•7H2O), iron (II) sulfate heptahydrate (FeSO4•7H2O), calcium chloride dihydrate (CaCl2•2H2O), agar, crystal violet, Hank’s balanced salt solution (HBSS)(+) and 99.5% ethanol (EtOH) were purchased from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan). SLES was purchased from the NOF Corporation (Tokyo, Japan). The Dulbecco’s phosphate-buffered saline (d -PBS)(+) preparation reagent (with Ca and Mg) (100×) and fetal bovine serum (FBS) were purchased from Nacalai Tesque (Kyoto, Japan) and Thermo Fisher Scientific K.K. (Tokyo, Japan), respectively. WELPAS® antiseptic solution for hands (0.2%), an alcohol-based disinfectant, was purchased from Maruishi Pharmaceutical Co. Ltd. (Osaka, Japan).
8
Lipid Extraction and Derivatization Protocol
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Ricinoleic acid and palmitic acid were purchased from Tokyo Chemical Industry Co (Tokyo, Japan). Oleic acid, linoleic acid, and ethyl acetate were purchased from Duksan Pure Chemical Co. (Ansan, Republic of Korea). Glucose was purchased from Junsei Chemical Co (Tokyo, Japan). Antibiotics, trace elements for culture medium, and Tween80 were purchased from Sigma (St. Louis, MO, USA). N-Methyl-N-(trimethylsilyl)trifluoroacetamide (TMS) was obtained from Tokyo Chemical Industry Co. (Tokyo, Japan).
9
Isoquercitrin Attenuates Fatty Acid-Induced Hepatocyte Damage
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Human HepG2 cells were purchased from American Type Culture Collection (Manassas, VA, USA). Cells were grown in Dulbecco’s modified Eagle’s medium (Gibco, Invitrogen, Carlsbad, CA, USA) containing 10% heat-inactivated fetal bovine serum (Hyclone, Logan, UT, USA) and 1% penicillin/streptomycin solution (Hyclone) at 37 °C in a humidified atmosphere of 5% CO2. The medium was replaced every 2–3 days for all cell culture assays. Isoquercitrin (quercetin-3-O-β-d-glucopyranoside, ≥98% purity, #17793, Sigma-Aldrich, Inc., St. Louis, MO, USA) was treated to HepG2 cells for 6 h prior to FFA exposure, at the concentrations ranging from 1 to 50 μM which previously showed its lipid-lowering effect in rat primary hepatocytes by 24 h incubation without negative effects [16 (link)]. Cells were incubated with 0.5 mM FFA composed of oleic acid (#O7501, Sigma-Aldrich, Inc.) and palmitic acid (#P0007, Tokyo Chemical Industry Co. Ltd., Tokyo, Japan; 2:1) with or without Isoquercitrin (1–50 μM) co-treatment for 24 h, and samples were harvested for analysis.
10
Fatty Acid Profiling Protocol
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2-Nitrophenylhydrazine hydrochloride (2-NPH•HCl), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1-EDC•HCl), butyric acid (FA4:0), hexanoic acid (FA6:0), heptanoic acid (FA7:0), octanoic acid (FA8:0), undecanoic acid (FA11:0), lauric acid (FA12:0), myristic acid (FA14:0), palmitic acid (FA16:0), heptadecanoic acid (margaric acid, FA17:0), stearic acid (FA18:0), nonadecanoic acid (FA19:0), arachidic acid (FA20:0), tricosanoic acid (FA23:0), linOleic acid (FA18:2), and linolenic acid (FA18:3) were purchased from Tokyo Chemical Industry Co., Ltd (Tokyo, Japan). Oleic acid (FA18:1), arachidonic acid (FA20:4), eicosapentaenoic acid (EPA, FA20:5) and docosahexaenoic acid (DHA, FA22:6) were obtained from Sigma-Aldrich Japan (Tokyo, Japan). Capric acid (FA10:0), and HPLC grade methanol and water were from Wako Pure Chemical Industry (Osaka, Japan). FA labeling reagents were obtained from YMC CO (Kyoto, Japan).
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