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The conformation and CETP inhibitory activity of [10]-dehydrogingerdione isolated from Zingiber officinale

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Abstract

In the course of searching for cholesteryl ester transfer protein (CETP) inhibitors from natural sources, a new type of CETP inhibitor, [10]-dehydrogingerdione (1), was isolated from the extract of rhizomes of Zingiber officinale Roscoe. By NMR spectroscopic analysis of its 1HNMR, 13C-NMR, and 1H-1H COSY, HMBC, HMQC and NOESY, more precise structure, compared with its originally proposed structures, of [10]-dehydrogingerdione has been elucidated. This active compound inhibited human plasma CETP with IC50 values of 35 μM.

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References

  • Ali, B. H., Blunden, G., Tanira, M. O., and Nemmar, A., Some phytochemical, pharmacological and toxicological properties of ginger (Zingiber officinale Roscoe): a review of recent research. Food Chem. Toxicol., 46, 409–420 (2008).

    Article  PubMed  CAS  Google Scholar 

  • Barter, P. and Rye, K. A., Cholesteryl ester transfer protein: its role in plasma lipid transport. Clin. Exp. Pharmacol. Physiol., 21, 663–672 (1994).

    Article  PubMed  CAS  Google Scholar 

  • Barter, P. J. and Kastelein, J. J. P., Targeting cholesteryl ester transfer protein for the prevention and management of cardiovascular disease. J. Am. Coll. Cardiol., 47, 492–499 (2006).

    Article  PubMed  CAS  Google Scholar 

  • Chen, C. Y., Tai, C. J., Cheng, J. T., Zheng, J. J., Chen, Y. Z., Liu, T. Z., Yiin, S. J., and Chern, C. L., 6-dehydrogingerdione sensitizes human hepatoblastoma Hep G2 cells to TRAIL-induced apoptosis via reactive oxygen speciesmediated increase of DR5. J. Agric. Food Chem., 58, 5604–5611 (2010).

    Article  PubMed  CAS  Google Scholar 

  • Clark, R. W., Ruggeri, R. B., Cunningham, D., and Bamberger, M. J., Description of the torcetrapib series of cholesteryl ester transfer protein inhibitors, including mechanism of action. J. Lipid Res., 47, 537–552 (2006).

    Article  PubMed  CAS  Google Scholar 

  • Coval, S. J., Conover, M. A., Mierzwa, R., King, A., Puar, M. S., Phife, D. W., Pai, J.-K., Burrier, R. E., Ahn, H.-S., Boykow, G. C., Patel, M., and Pomponi, S. A., Wiedendiol-A and -B, cholesteryl ester transfer protein inhibitors from the marine sponge Xestospongia wiedenmayeri. Bioorg. Med. Chem. Lett., 5, 605–610 (1995).

    Article  CAS  Google Scholar 

  • De Grooth, G. J., Kuivenhoven, J. A., Stalenhoef, A. F. H., De Graaf, J., Zwinderman, A. H., Posma, J. L., Van Tol, A., and Kastelein, J. J. P., Efficacy and safety of a novel cholesteryl ester transfer protein inhibitor, JTT-705, in humans: a randomized phase II dose-response study. Circulation, 105, 2159–2165 (2002).

    Article  PubMed  Google Scholar 

  • Grzanna, R., Lindmark, L., and Frondoza, C. G., Ginger—an herbal medicinal product with broad anti-inflammatory actions. J. Med. Food, 8, 125–132 (2005).

    Article  PubMed  CAS  Google Scholar 

  • Jagetia, G., Baliga, M., and Venkatesh, P., Ginger (Zingiber officinale Rosc.), a dietary supplement, protects mice against radiation-induced lethality: mechanism of action. Cancer Biother. Radiopharm., 19, 422–435 (2004).

    PubMed  CAS  Google Scholar 

  • Jeong, T.-S., Ahn, J.-A., Kim, Y.-K., Bok, S.-H., Kwon, B.-M., Shin, J., and Seo, Y., CETP inhibitory activity of ceramides, isolated from the gorgonian Acabaria undulata. Bioorg. Med. Chem. Lett., 7, 1481–1482 (1997).

    Article  CAS  Google Scholar 

  • Jolad, S. D., Lantz, R. C., Chen, G. J., Bates, R. B., and Timmermann, B. N., Commercially processed dry ginger (Zingiber officinale): composition and effects on LPS-stimulated PGE2 production. Phytochemistry, 66, 1614–1635 (2005).

    Article  PubMed  CAS  Google Scholar 

  • Kiuchi, F., Iwakami, S., Shibuya, M., Hanaoka, F., and Sankawa, U., Inhibition of prostaglandin and leukotriene biosynthesis by gingerols and diarylheptanoids. Chem. Pharm. Bull. (Tokyo), 40, 387–391 (1992).

    CAS  Google Scholar 

  • Lagrost, L., Loreau, N., Gambert, P., and Lallemant, C., Immunospecific scintillation proximity assay of cholesteryl ester transfer protein activity. Clin. Chem., 41, 914–919 (1995).

    PubMed  CAS  Google Scholar 

  • McGovern, P. G., Pankow, J. S., Shahar, E., Doliszny, K. M., Folsom, A. R., Blackburn, H., and Luepker, R. V., Recent trends in acute coronary heart disease—mortality, morbidity, medical care, and risk factors. The Minnesota Heart Survey Investigators. N. Engl. J. Med., 334, 884–890 (1996).

    Article  PubMed  CAS  Google Scholar 

  • Parini, P. and Rudel, L. L., Is there a need for cholesteryl ester transfer protein inhibition? Arterioscler. Thromb. Vasc. Biol., 23, 374–375 (2003).

    Article  PubMed  CAS  Google Scholar 

  • Rehberg, E. F., Greenlee, K. A., Melchior, G. W., and Marotti, K. R., Purification of human cholesteryl ester transfer protein by affinity chromatography on immobilized triazine dyes. Protein Expr. Purif., 5, 285–290 (1994).

    Article  PubMed  CAS  Google Scholar 

  • Sang, S., Hong, J., Wu, H., Liu, J., Yang, C. S., Pan, M. H., Badmaev, V., and Ho, C. T., Increased growth inhibitory effects on human cancer cells and anti-inflammatory potency of shogaols from Zingiber officinale relative to gingerols. J. Agric. Food Chem., 57, 10645–10650 (2009).

    Article  PubMed  CAS  Google Scholar 

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Correspondence to Young Kook Kim.

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Choi, SY., Park, GS., Lee, S.Y. et al. The conformation and CETP inhibitory activity of [10]-dehydrogingerdione isolated from Zingiber officinale . Arch. Pharm. Res. 34, 727–731 (2011). https://doi.org/10.1007/s12272-011-0505-5

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  • DOI: https://doi.org/10.1007/s12272-011-0505-5

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