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Sucutinirane-diterpene derivatives induce apoptosis via oxidative stress in HL-60 cells

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Abstract

Previously, we reported the isolation of cassane-type diterpenes, sucutiniranes A–F, from the seeds of Bowdichia nitida. In this study, a series of sucutinirane derivatives was prepared, and their in vitro toxicity in the HL-60 cell line was evaluated. Then the action mechanism of a representative compound that induces cell death was investigated. Whereas C-6 or C-7 diol esters and ether decreased the activity against the HL-60 cell line, furan-oxidized derivatives 12 and 13 showed improvement or retention of the activity compared with those of the natural products sucutinirane A (11), E (1), and F (2). Treatment with sucutinirane derivative 13 elevated caspase 3/7 activity and also decreased expression of Bcl-2 family proteins, Mcl-1, and Bid. Derivative 13 generated reactive oxygen species in HL-60 cells, whose apoptotic effects were attenuated by the addition of an antioxidant, N-acetyl-l-cysteine. These results suggest that cassane butenolide 13 induces apoptosis in HL-60 via its oxidative effects.

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Acknowledgments

This work was supported by Grants in-Aid for Scientific Research from JSPS.

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Authors and Affiliations

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

    Jun Deguchi, Kaori Horiguchi, Chin Piow Wong, Takahiro Hosoya, Akane Iihoshi, Toshio Kaneda & Hiroshi Morita

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  1. Jun Deguchi
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  2. Kaori Horiguchi
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  3. Chin Piow Wong
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  4. Takahiro Hosoya
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  5. Akane Iihoshi
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  6. Toshio Kaneda
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  7. Hiroshi Morita
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Correspondence to Hiroshi Morita.

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Deguchi, J., Horiguchi, K., Wong, C.P. et al. Sucutinirane-diterpene derivatives induce apoptosis via oxidative stress in HL-60 cells. J Nat Med 68, 723–729 (2014). https://doi.org/10.1007/s11418-014-0848-6

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  • DOI: https://doi.org/10.1007/s11418-014-0848-6

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