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Vincazalidine A, a unique bisindole alkaloid from Catharanthus roseus

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Abstract

A new dimeric indole alkaloid, vincazalidine A consisting of an aspidosperma type and a modified iboga type with 1-azatricyclo ring system consisting of one azepane and two piperidine rings coupled with an oxazolidine ring was isolated from Catharanthus roseus, and the structure including absolute stereochemistry was elucidated on the basis of spectroscopic data as well as DP4 statistical analysis. Vincazalidine A induced G2 arrest and subsequent apoptosis in human lung carcinoma cell line, A549 cells.

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Acknowledgements

This work was partly supported by JSPS KAKENHI (JP 19K07152 and JP22K06671 to MH) and (22K06685 to YH), Japan.

Funding

This work was partly supported by JSPS KAKENHI (JP 19K07152 and JP22K06671 to MH) and (22K06685 to YH), Japan.

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Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41 Shinagawa-Ku, Tokyo, 142-8501, Japan

    Yusuke Hirasawa, Ayaka Kase, Akie Okamoto, Keigo Suzuki, Mizuki Hiroki, Toshio Kaneda & Hiroshi Morita

  2. National Institute of Health Sciences, 3-25-26 Tonomachi, Kawasaki-Ku, Kawasaki, Kanagawa, 210-9501, Japan

    Nahoko Uchiyama

Authors
  1. Yusuke Hirasawa
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  2. Ayaka Kase
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  5. Mizuki Hiroki
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Contributions

YH, AK, AO, KS, MH, TK, NU and HM conceived and designed the experiments; YH, TK, and HM wrote the paper.

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Correspondence to Yusuke Hirasawa or Hiroshi Morita.

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Hirasawa, Y., Kase, A., Okamoto, A. et al. Vincazalidine A, a unique bisindole alkaloid from Catharanthus roseus. J Nat Med 78, 382–392 (2024). https://doi.org/10.1007/s11418-023-01775-x

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  • DOI: https://doi.org/10.1007/s11418-023-01775-x

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