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A novel terpenoid indole alkaloid derived from catharanthine via biotransformation by suspension-cultured cells of Catharanthus roseus

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Abstract

Objective

Although catharanthine (1) is well known as a biosynthetic precursor of the anticancer alkaloid, vinblastine, its alternative metabolic pathways are unclear.

Results

Biotransformation of 1 by suspension-cultured cells of Catharanthus roseus gave a new oxidative-cleavage product (2). The structure of 2 was determined as 3-hydroxy-4-imino-catharanthine by spectroscopic methods. Maximum conversion (9.75 %) of 2 was observed after 120 h adding 6 mg of 1/100 ml to 12-day-old suspension-cultured cells of C. roseus. Furthermore, qRT-PCR experiment was performed to reveal the effect of 1 on the expression of the genes in the biosynthetic pathway of TIA 1 up-regulated the transcript level of D4H whilst down-regulating the transcript levels of G10H, LAMT, GES, and IRS.

Conclusion

A new metabolite of catharanthine, 3-hydroxy-4-imino-catharanthine, is reported.

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Acknowledgments

This research was financially supported by National Natural Sciences Foundation of China (No. 81073004, 81102771 and 81274045), Pearl River Scientific and Technological New Star Program of Guangzhou (No. 2014J2200004), the Natural Science Foundation of Guangdong Province (No. 2014A030313385) and Science and Technology Specific Project of Guangzhou (No.201300000138).

Supporting information

Supplementary Table 1—Primers used in this paper (see also Zhou et al. 2015).

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    Authors and Affiliations

    1. Biotechnological Institute of Chinese Materia Medica, College of Pharmacy, Jinan University, Guangzhou, 510632, China

      Shuijie He, Pengfei Zhou, Jincai Liang & Rongmin Yu

    2. Department of Natural Products Chemistry, College of Pharmacy, Jinan University, Guangzhou, 510632, China

      Jianhua Zhu, Jiachen Zi & Rongmin Yu

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    1. Shuijie He
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    2. Jianhua Zhu
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    3. Jiachen Zi
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    4. Pengfei Zhou
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    Corresponding authors

    Correspondence to Jiachen Zi or Rongmin Yu.

    Additional information

    Shuijie He and Jianhua Zhu have contributed equally to this work.

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    Supplementary material 1 (DOCX 12 kb)

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    He, S., Zhu, J., Zi, J. et al. A novel terpenoid indole alkaloid derived from catharanthine via biotransformation by suspension-cultured cells of Catharanthus roseus . Biotechnol Lett 37, 2481–2487 (2015). https://doi.org/10.1007/s10529-015-1930-1

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