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Prenylated Acylphloroglucinol Derivatives: Isoprenomics-Based Design, Syntheses and Antioxidative Activities

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Oxygen Transport to Tissue XXXIII

Part of the book series: Advances in Experimental Medicine and Biology ((AEMB,volume 737))

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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Authors and Affiliations

  1. Department of Life System, Institute of Technology and Science, Graduate School, The University of Tokushima, Minamijosanjimacho-2, Tokushima, 770-8506, Japan

    Ryo Tanaka, Yoshihiro Uto, Kenta Ohnaka, Yuki Ohta, Eiji Nakata & Hitoshi Hori

  2. Laboratory of Plant Gene Expression, Research Institute for Sustainable Humanosphere, Kyoto University, Uji, 611-0011, Japan

    Kazufumi Yazaki

  3. Central Laboratories for Frontier Technology, Kirin Holdings Co., Ltd., Tochigi, 329-1414, Japan

    Naoyuki Umemoto

Authors
  1. Ryo Tanaka
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  2. Yoshihiro Uto
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  3. Kenta Ohnaka
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  4. Yuki Ohta
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  5. Kazufumi Yazaki
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  6. Naoyuki Umemoto
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  7. Eiji Nakata
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  8. Hitoshi Hori
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Corresponding author

Correspondence to Ryo Tanaka .

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Editors and Affiliations

  1. , Division of Neonatology, University Hospital Zurich, Frauenklinikstr. 10, Zurich, 8091, Switzerland

    Martin Wolf

  2. , Division of Neonatology, University Hospital Zurich, Frauenklinikstr. 10, Zurich, 8091, Switzerland

    Hans Ulrich Bucher

  3. Institute for Biomedical Engineering, University of Zurich/ETHZ, Wolfgang-Pauli-Strasse 27, Zurich, 8093, Switzerland

    Markus Rudin

  4. ESAT-SCD(SISTA), Dept. Elektrotechniek, Katholieke Universiteit Leuven, Kasteelpark Arenberg 10, Leuven-Heverlee, 3001, Belgium

    Sabine Van Huffel

  5. , Institute of Complementary Medicine KIKO, University of Bern, Imhoof-Pavillon, Inselspital, Bern, 3010, Switzerland

    Ursula Wolf

  6. Synthesizer Inc., Synthesizer Inc. 2773, Ellicott City, 21043, Maryland, USA

    Duane F. Bruley

  7. , Institute of Cellular Medicine, Newcastle University, Newcastle upon Tyne, NE1 7RU, United Kingdom

    David K Harrison

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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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