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Acyl flavonoids, biflavones, and flavonoids from Cephalotaxus harringtonia var. nana

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Abstract

A methanol extract of the leaves of Cephalotaxus harringtonia var. nana and its ethyl acetate (EtOAc)-soluble fraction demonstrated strong antitumor activity against A549 and HT-29 cell lines. The EtOAc-soluble fraction was purified by column chromatography and high-performance liquid chromatography (HPLC) using a reverse-phase column to yield three novel acyl flavonoids and a biflavonoid, along with 15 other known compounds that included flavonoids, biflavonoids, and other phenolics. The structures of the new compounds were elucidated using spectral data from HR-MS and NMR, including two-dimensional NMR studies, as (2R,3R)-3-O-eicosanoyltaxifolin (1), (2R,3R)-3-O-docosanoyltaxifolin (2), (2R,3R)-3-O-tetracosanoyltaxifolin (3), and 6-methyl-4′,7,7″-tri-O-methylamentoflavone (4). The isolated compounds, including the known compounds, were tested for possible antitumor activity; some of the biflavones were found to be active. The potent antitumor activity of the extract was attributed to Cephalotaxus alkaloids, such as homoharringtonine (20).

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Author notes

  1. Setsuko Sekita

    Present address: Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo, 194-8543, Japan

  2. Masanori Kuroyanagi

    Present address: School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan

Authors and Affiliations

  1. Healthcare Research Institute, Wakunaga Pharmaceutical Co. Ltd., 1624 Shimokotachi, Kodach, Akitakata, Hiroshima, 739-1195, Japan

    Noriko Komoto

  2. Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo, 194-8543, Japan

    Takahisa Nakane

  3. Yakult Central Institute for Microbiological Research, 1976 Yaho, Kunitachi, Tokyo, 186-8650, Japan

    Sachiko Matsumoto & Shusuke Hashimoto

  4. Kagawa School of Pharmaceutical Sciences, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa, 769-2193, Japan

    Osamu Shirota, Setsuko Sekita & Masanori Kuroyanagi

Authors
  1. Noriko Komoto
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  2. Takahisa Nakane
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  3. Sachiko Matsumoto
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  4. Shusuke Hashimoto
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  5. Osamu Shirota
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  7. Masanori Kuroyanagi
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Corresponding authors

Correspondence to Osamu Shirota or Masanori Kuroyanagi.

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Komoto, N., Nakane, T., Matsumoto, S. et al. Acyl flavonoids, biflavones, and flavonoids from Cephalotaxus harringtonia var. nana . J Nat Med 69, 479–486 (2015). https://doi.org/10.1007/s11418-015-0912-x

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  • DOI: https://doi.org/10.1007/s11418-015-0912-x

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