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3 protocols using silica gel 60

1

Ligand Synthesis and Characterization

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The overall ligand synthesis scheme is shown in Supplementary Fig. 1 and described in Supplementary Methods. Analytical samples were homogeneous as confirmed by TLC, and afforded spectroscopic results consistent with the assigned structures. Proton and carbon nuclear magnetic resonance spectra (1H and 13C NMR) were taken on a Varian Mercury 300 spectrometer using deuterated chloroform (CDCl3) and deuterated dimethylsulfoxide (DMSO-d6) as the solvent. Fast atom bombardment mass spectra were obtained on a JEOL JMS-DX303HF spectrometer. Electrospray ionization (HRMS) mass spectra was obtained on a Thermo Fisher Scientific LTQ Orbitrap XL system. Column chromatography was carried out on silica gel (Merck Silica Gel 60, Wako gel C-200, or Fuji Silysia FL60D). Thin layer chromatography was performed on silica gel (Merck TLC or HPTLC plates, Silica Gel 60 F254).
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2

Anti-Inflammatory Effects of Garlic Compounds

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Garlic was purchased from Shinko Company (Kumamoto, Japan). DSS was purchased from MP Biomedicals, LLC (Irvine, CA, USA). AOM, cell culture media (RPMI-1640, DMEM), mouse monocyte chemotactic protein 1 (MCP-1) Quantikine ELISA kit, and mouse tumor necrosis factor-α (TNF-α) Quantikine ELISA kit were purchased from Fujifilm Wako Pure Chemical Corporation (Osaka, Japan). Methyl cellulose, thiazolyl blue tetrazolium bromide (MTT), and 7′-dichlorodihydrofluorescein diacetate (DCDFH-DA) were purchased from Sigma-Aldrich Chemical (St. Louis, MO, USA). Solvents including dimethyl sulfoxide (DMSO), acetone, ethyl acetate (AcOEt), hexane, chloroform, and silica gel 60 were from Fujifilm Wako Pure Chemical Corporation.
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3

DSPE Synthesis and Characterization

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1,2-Di-O-stearoyl-sn-glycero-3-phosphatidylethanolamine (DSPE) was manufactured by Nippon Fine Chemical Co., Ltd. (Osaka, Japan) . Calcium decanoate was purchased from Mitsuwa Chemicals Co., Ltd. (Osaka, Japan) . Calcium stearate, D-glucose, octane, Silica Gel 60, sodium hydroxide, methanol, boron trifluoride methanol complex methanol solution, and n-hexane were purchased from Fujifilm Wako Pure Chemical Corporation (Osaka, Japan) .
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