Abstract
We designed isoprenomics-based prenylated biosynthetic intermediates of cohumulone and colupulone as Low-density lipoprotein (LDL)-targeting antioxidants. Syntheses of acylphloroglucinol (UTX-52), mono-prenylated acylphloroglucinol (UTX-53), and di-prenylated acylphloroglucinol (UTX-54) were performed according to our established aromatic prenylation method. The free radical-scavenging activity of UTX-53 was highest among all the compounds tested and its potency was about twice as International Calibration Extract as a hop extract. The inhibitory activity of UTX-53 on linoleic acid oxidation showed about four times higher than ICE-2. The inhibitory activity of UTX-52, UTX-53, and UTX-54 on human LDL oxidation showed almost the same inhibitory activity, and these compounds were weaker than that of ICE-2. According to these results, we suggest that the antioxidative activity of prenylated acylphloroglucinols strongly depends on the radical scavenging activity rather than the hydrophobicity of, e.g., artepillin C analogues.
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Acknowledgments
We thank Ms. Maki Nakamura, Ms. Emiko Okayama and the staff of our faculty for measurement of NMR and elemental analyses.
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Tanaka, R. et al. (2012). Prenylated Acylphloroglucinol Derivatives: Isoprenomics-Based Design, Syntheses and Antioxidative Activities. In: Wolf, M., et al. Oxygen Transport to Tissue XXXIII. Advances in Experimental Medicine and Biology, vol 737. Springer, New York, NY. https://doi.org/10.1007/978-1-4614-1566-4_37
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DOI: https://doi.org/10.1007/978-1-4614-1566-4_37
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