Bioactive Pregnanes from <i>Nerium </i><i>oleander</i>

  • Liming Bai
    Graduate School of Science and Technology and Department of Chemistry and Chemical Engineering, Niigata University, Ikarashi, 2-8050, Niigata 950-2181, Japan, Mitsubishi Gas Chemical Company Inc., Niigata Research Laboratory, 182, Shinwari, Tayuhama, Niigata 950-3112, Japan, Center for Biological Resources and Informatics, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan, KNC Laboratories Co., Ltd., 3-2-34 Takatsukadai, Nishi-ku, Kobe Hyogo 651-2271, Japan
  • Liyan Wang
    Graduate School of Science and Technology and Department of Chemistry and Chemical Engineering, Niigata University, Ikarashi, 2-8050, Niigata 950-2181, Japan, Mitsubishi Gas Chemical Company Inc., Niigata Research Laboratory, 182, Shinwari, Tayuhama, Niigata 950-3112, Japan, Center for Biological Resources and Informatics, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan, KNC Laboratories Co., Ltd., 3-2-34 Takatsukadai, Nishi-ku, Kobe Hyogo 651-2271, Japan
  • Ming Zhao
    Graduate School of Science and Technology and Department of Chemistry and Chemical Engineering, Niigata University, Ikarashi, 2-8050, Niigata 950-2181, Japan, Mitsubishi Gas Chemical Company Inc., Niigata Research Laboratory, 182, Shinwari, Tayuhama, Niigata 950-3112, Japan, Center for Biological Resources and Informatics, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan, KNC Laboratories Co., Ltd., 3-2-34 Takatsukadai, Nishi-ku, Kobe Hyogo 651-2271, Japan
  • Asami Toki
    Graduate School of Science and Technology and Department of Chemistry and Chemical Engineering, Niigata University, Ikarashi, 2-8050, Niigata 950-2181, Japan, Mitsubishi Gas Chemical Company Inc., Niigata Research Laboratory, 182, Shinwari, Tayuhama, Niigata 950-3112, Japan, Center for Biological Resources and Informatics, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan, KNC Laboratories Co., Ltd., 3-2-34 Takatsukadai, Nishi-ku, Kobe Hyogo 651-2271, Japan
  • Toshiaki Hasegawa
    Graduate School of Science and Technology and Department of Chemistry and Chemical Engineering, Niigata University, Ikarashi, 2-8050, Niigata 950-2181, Japan, Mitsubishi Gas Chemical Company Inc., Niigata Research Laboratory, 182, Shinwari, Tayuhama, Niigata 950-3112, Japan, Center for Biological Resources and Informatics, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan, KNC Laboratories Co., Ltd., 3-2-34 Takatsukadai, Nishi-ku, Kobe Hyogo 651-2271, Japan
  • Hirotsugu Ogura
    Graduate School of Science and Technology and Department of Chemistry and Chemical Engineering, Niigata University, Ikarashi, 2-8050, Niigata 950-2181, Japan, Mitsubishi Gas Chemical Company Inc., Niigata Research Laboratory, 182, Shinwari, Tayuhama, Niigata 950-3112, Japan, Center for Biological Resources and Informatics, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan, KNC Laboratories Co., Ltd., 3-2-34 Takatsukadai, Nishi-ku, Kobe Hyogo 651-2271, Japan
  • Takao Kataoka
    Graduate School of Science and Technology and Department of Chemistry and Chemical Engineering, Niigata University, Ikarashi, 2-8050, Niigata 950-2181, Japan, Mitsubishi Gas Chemical Company Inc., Niigata Research Laboratory, 182, Shinwari, Tayuhama, Niigata 950-3112, Japan, Center for Biological Resources and Informatics, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan, KNC Laboratories Co., Ltd., 3-2-34 Takatsukadai, Nishi-ku, Kobe Hyogo 651-2271, Japan
  • Katutoshi Hirose
    Graduate School of Science and Technology and Department of Chemistry and Chemical Engineering, Niigata University, Ikarashi, 2-8050, Niigata 950-2181, Japan, Mitsubishi Gas Chemical Company Inc., Niigata Research Laboratory, 182, Shinwari, Tayuhama, Niigata 950-3112, Japan, Center for Biological Resources and Informatics, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan, KNC Laboratories Co., Ltd., 3-2-34 Takatsukadai, Nishi-ku, Kobe Hyogo 651-2271, Japan
  • Junichi Sakai
    Graduate School of Science and Technology and Department of Chemistry and Chemical Engineering, Niigata University, Ikarashi, 2-8050, Niigata 950-2181, Japan, Mitsubishi Gas Chemical Company Inc., Niigata Research Laboratory, 182, Shinwari, Tayuhama, Niigata 950-3112, Japan, Center for Biological Resources and Informatics, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan, KNC Laboratories Co., Ltd., 3-2-34 Takatsukadai, Nishi-ku, Kobe Hyogo 651-2271, Japan
  • Jiao Bai
    Graduate School of Science and Technology and Department of Chemistry and Chemical Engineering, Niigata University, Ikarashi, 2-8050, Niigata 950-2181, Japan, Mitsubishi Gas Chemical Company Inc., Niigata Research Laboratory, 182, Shinwari, Tayuhama, Niigata 950-3112, Japan, Center for Biological Resources and Informatics, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan, KNC Laboratories Co., Ltd., 3-2-34 Takatsukadai, Nishi-ku, Kobe Hyogo 651-2271, Japan
  • Masayoshi Ando
    Graduate School of Science and Technology and Department of Chemistry and Chemical Engineering, Niigata University, Ikarashi, 2-8050, Niigata 950-2181, Japan, Mitsubishi Gas Chemical Company Inc., Niigata Research Laboratory, 182, Shinwari, Tayuhama, Niigata 950-3112, Japan, Center for Biological Resources and Informatics, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan, KNC Laboratories Co., Ltd., 3-2-34 Takatsukadai, Nishi-ku, Kobe Hyogo 651-2271, Japan

説明

Three new pregnanes, 21-hydroxypregna-4,6-diene-3,12,20-trione (1), 20R-hydroxypregna-4,6-diene-3,12-dione (2), and 16beta,17beta-epoxy-12beta-hydroxypregna-4,6-diene-3,20-dione (3), were isolated from Nerium oleander, together with two known compounds, 12beta-hydroxypregna-4,6,16-triene-3,20-dione (neridienone A, 4) and 20S,21-dihydroxypregna-4,6-diene-3,12-dione (neridienone B, 5). The structures of compounds 1-3 were established on the basis of their spectroscopic data. The anti-inflammatory activity in vitro of compounds 2-4 was examined on the basis of inhibitory activity against the induction of intercellular adhesion molecule-1 (ICAM-1), and compound 4 was active. The cytotoxic activity of compounds 1-5 was evaluated against four human cell lines, normal human fibroblast cells (WI-38), malignant tumor cells induced from WI-38 (VA-13), human liver tumor cells (HepG2), and human lung carcinoma cells (A-549). Compound 4 showed significant cell growth inhibition of VA-13 and HepG2 cells. The MDR-reversal activity of compounds 1-5 was evaluated on the basis of the amount of calcein accumulated in MDR human ovarian cancer 2780AD cells in the presence of each compound. Compounds 1, 2, and 5 showed significant effects on calcein accumulation.

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