The structure of a new cardenolide diglycoside and the biological activities of eleven cardenolide diglycosides from Nerium oleander

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  • Zhao Ming
    College of Chemistry and Chemical Engineering, Qiqihar University
  • Bai Liming
    College of Chemistry and Chemical Engineering, Qiqihar University
  • Toki Asami
    Graduate School of Science and Technology, Niigata University
  • Hasegawa Ryo
    Graduate School of Science and Technology, Niigata University
  • Sakai Jun-ichi
    Department of Chemistry and Chemical Engineering, Faculty of Engineering, Niigata University
  • Hasegawa Toshiaki
    Mitsubishi Gas Chemical Company, Inc., Niigata Research Laboratory
  • Ogura Hirotsugu
    Center for Biological Resources and Informatics, Tokyo Institute of Technology
  • Kataoka Takao
    Center for Biological Resources and Informatics, Tokyo Institute of Technology
  • Bai Yuhua
    Department of Medicinal Chemistry, Pharmaceutical Department, Daqing Campus of Harbin Medical University
  • Ando Mariko
    Technical Division, School of Engineering, Tohoku University
  • Hirose Katsutoshi
    KNC Laboratories Co., Ltd.
  • Ando Masayoshi
    Department of Chemistry and Chemical Engineering, Faculty of Engineering, Niigata University

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  • The Structure of a New Cardenolide Diglycoside and the Biological Activities of Eleven Cardenolide Diglycosides from <i>Nerium oleander</i>

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A new cardenolide diglycoside (1) was isolated from Nerium oleander together with ten known cardenolide diglycosides 2—11. The structure of compound 1 was established on the basis of their spectroscopic data. The in vitro anti-inflammatory activity of compounds 1—11 was examined on the basis of inhibitory activity against the induction of the intercellular adhesion molecule-1 (ICAM-1). Compounds 2—5 were active at an IC50 value of less than 0.8 μM. The cytotoxicity of compounds 1—11 was evaluated against three human cell lines normal human fibroblast cells (WI-38), malignant tumor cells induced from WI-38 (VA-13), and human liver tumor cells (HepG2). Compound 3 was active toward VA-13 cells, and compounds 2—5 were active toward HepG2 cells at IC50 values of less than 1.3 μM. The multidrug resistance (MDR)-reversal activity of compounds 1—11 was evaluated on the basis of the amount of calcein in MDR human ovarian cancer 2780AD cells in the presence of each compound. Compounds 1 and 8 showed moderate effects on calcein accumulation.

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