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Journal of Wood Science

Official Journal of the Japan Wood Research Society

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Polar cardenolide monoglycosides from stems and twigs of Nerium oleander and their biological activities

Journal of Wood Science volume 57, pages 47–55 (2011)Cite this article

Abstract

Twelve polar cardenolide monoglycosides, 1, 2, 4–13, and oleagenin (3) were isolated from the methanol extract of stems and twigs of Nerium oleander. Among these, oleagenin (3) and cardenolide monoglycosides named cardenolide B-1 (1) and cardenolide B-2 (2) were isolated from natural sources for the first time. The in vitro antiinflammatory activity of compounds 1–13 was examined on the basis of inhibitory activity against the induction of the intercellular adhesion molecule-1 (ICAM-1). Compounds 4–7 were active at an IC50 value of less than 0.4 μM. The cytotoxic activity of compounds 1–13 was evaluated against three human cell lines: normal human fibroblast cells (WI-38), malignant tumor cells derived from WI-38 (VA-13), and human liver tumor cells (HepG2). Compounds 4, 6, and 7 were active toward these three cell lines at IC50 values of less than 0.7 μM, and compounds 5 and 8 were active toward the cell lines at IC50 values of less than 1.5 μM. The multidrug resistance (MDR) cancer-reversal activity of compounds 1–13 was evaluated on the basis of the amount of calcein accumulated in MDR human ovarian cancer 2780AD cells in the presence of each compound. Compound 1 and 12 showed significant effects on calcein accumulation.

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Authors and Affiliations

  1. College of Chemistry and Chemistry Engineering, Qiqihar University, 30 Wenhuadajie, Qiqihar, Heilongjian, 161006, China

    Liming Bai & Ming Zhao

  2. Graduate School of Science and Technology, Niigata University, Niigata, 950-2181, Japan

    Asami Toki

  3. Niigata Research Laboratory, T. Hasegawa Mitsubishi Gas Chemical Company, Inc., Niigata, 950-3112, Japan

    Toshiaki Hasegawa

  4. Department of Chemistry and Chemical Engineering, Faculty of Engineering, Niigata University, Niigata, 950-2181, Japan

    Jun-ichi Sakai & Mariko Ando

  5. Atmospheric Chemistry and Aerosol Division, Chinese Research Academy of Environmental Science, Beijing, 100012, China

    Xiao-yang Yang

  6. Department of Medicinal Chemistry, Pharmaceutical Department, Daqing Campus of Harbin Medical University, Daqing, 163319, China

    Yuhua Bai

  7. Center for Biological Resources and Informatics, Tokyo Institute of Technology, Yokohama, 226-8501, Japan

    Hirotsugu Ogura, Tomokazu Mitsui & Takao Kataoka

  8. KNC Laboratories Co., Ltd., Kobe, 651-2271, Japan

    Katsutoshi Hirose

  9. Technical Division, School of Engineering, Tohoku University, Sendai, 980-8579, Japan

    Masayoshi Ando

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  1. Liming Bai
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  2. Ming Zhao
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  3. Asami Toki
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  4. Toshiaki Hasegawa
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  5. Jun-ichi Sakai
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  6. Xiao-yang Yang
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  7. Yuhua Bai
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  8. Hirotsugu Ogura
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  9. Tomokazu Mitsui
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  10. Takao Kataoka
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  11. Mariko Ando
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  12. Katsutoshi Hirose
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  13. Masayoshi Ando
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Corresponding author

Correspondence to Liming Bai.

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Bai, L., Zhao, M., Toki, A. et al. Polar cardenolide monoglycosides from stems and twigs of Nerium oleander and their biological activities. J Wood Sci 57, 47–55 (2011). https://doi.org/10.1007/s10086-010-1138-x

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  • DOI: https://doi.org/10.1007/s10086-010-1138-x

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