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Four new diterpenoid alkaloids from Aconitum japonicum subsp. subcuneatum

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Abstract

Diterpenoid alkaloids with remarkable chemical properties and biological activities are frequently found in plants of the genera Aconitum, Delphinium, and Garrya. Accordingly, several diterpenoid alkaloid constituents of Aconitum and Delphinium plants as well as their derivatives exhibited cytotoxic activity against lung, prostate, nasopharyngeal, and vincristine-resistant nasopharyngeal cancer cell lines. Four new C19-diterpenoid alkaloids, 14-anisoyllasianine (1), 14-anisoyl-N-deethylaconine (2), N-deethylaljesaconitine A (3), and N-deethylnevadensine (4), together with 17 known C19- and C20-diterpenoid alkaloids, were isolated in a phytochemical investigation of rhizoma of Aconitum japonicum Thunb. subsp. subcuneatum (Nakai) Kadota. Their structures were elucidated by extensive spectroscopic methods including NMR (1D and 2D), IR, and MS (HRMS). Eight known diterpenoid alkaloids, lipoaconitine, lipomesaconitine, aconine, nevadenine, talatisamine, nevadensine, ryosenamine, and dehydrolucidusculine, were isolated the first time from A. japonicum subsp. subcuneatum. Three of the new C19-diterpenoid alkaloids (1, 3, 4) and six of the known diterpenoid alkaloids were evaluated for cytotoxic activity against five human tumor cell lines.

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Authors and Affiliations

  1. School of Pharmacy, Hokkaido Pharmaceutical University, 4-1 Maeda 7-jo 15-choume, Teine-ku, Sapporo, 006-8590, Japan

    Hiroshi Yamashita, Keiko Takeda, Machiko Haraguchi, Yuki Abe, Natsumi Kuwahara, Shota Suzuki, Ayaka Terui, Takumi Masaka, Naoko Munakata, Mariko Uchida, Masashi Nunokawa, Kyousuke Kaneda & Koji Wada

  2. Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC, 27599 7568, USA

    Masuo Goto & Kuo-Hsiung Lee

  3. Chinese Medicine Research and Development Center, China Medical University and Hospital, Taichung, Taiwan

    Kuo-Hsiung Lee

Authors
  1. Hiroshi Yamashita
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  2. Keiko Takeda
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  3. Machiko Haraguchi
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  4. Yuki Abe
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  5. Natsumi Kuwahara
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  6. Shota Suzuki
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  7. Ayaka Terui
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  8. Takumi Masaka
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  9. Naoko Munakata
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  10. Mariko Uchida
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  11. Masashi Nunokawa
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  12. Kyousuke Kaneda
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  13. Masuo Goto
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  14. Kuo-Hsiung Lee
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  15. Koji Wada
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Corresponding author

Correspondence to Koji Wada.

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Yamashita, H., Takeda, K., Haraguchi, M. et al. Four new diterpenoid alkaloids from Aconitum japonicum subsp. subcuneatum . J Nat Med 72, 230–237 (2018). https://doi.org/10.1007/s11418-017-1139-9

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  • DOI: https://doi.org/10.1007/s11418-017-1139-9

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