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Journal of Natural Medicines

, Volume 72, Issue 1, pp 230–237 | Cite as

Four new diterpenoid alkaloids from Aconitum japonicum subsp. subcuneatum

  • Hiroshi Yamashita
  • Keiko Takeda
  • Machiko Haraguchi
  • Yuki Abe
  • Natsumi Kuwahara
  • Shota Suzuki
  • Ayaka Terui
  • Takumi Masaka
  • Naoko Munakata
  • Mariko Uchida
  • Masashi Nunokawa
  • Kyousuke Kaneda
  • Masuo Goto
  • Kuo-Hsiung Lee
  • Koji WadaEmail author
Original Paper

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.

Keywords

Aconitum japonicum subsp. subcuneatum 14-Anisoyllasianine 14-Anisoyl-N-deethylaconine N-deethylaljesaconitine A N-deethylnevadensine Cytotoxicity 

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Copyright information

© The Japanese Society of Pharmacognosy and Springer Japan KK 2017

Authors and Affiliations

  • Hiroshi Yamashita
    • 1
  • Keiko Takeda
    • 1
  • Machiko Haraguchi
    • 1
  • Yuki Abe
    • 1
  • Natsumi Kuwahara
    • 1
  • Shota Suzuki
    • 1
  • Ayaka Terui
    • 1
  • Takumi Masaka
    • 1
  • Naoko Munakata
    • 1
  • Mariko Uchida
    • 1
  • Masashi Nunokawa
    • 1
  • Kyousuke Kaneda
    • 1
  • Masuo Goto
    • 2
  • Kuo-Hsiung Lee
    • 2
    • 3
  • Koji Wada
    • 1
    Email author
  1. 1.School of PharmacyHokkaido Pharmaceutical UniversitySapporoJapan
  2. 2.Natural Products Research Laboratories, UNC Eshelman School of PharmacyUniversity of North CarolinaChapel HillUSA
  3. 3.Chinese Medicine Research and Development CenterChina Medical University and HospitalTaichungTaiwan

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