Skip to main content
Log in

Biomimetic one-pot synthesis of vinblastine: NAD(P)H-mediated vinblastine synthesis from the product of FMN-mediated vindoline–catharanthine coupling under near-ultraviolet light

  • Published:
Biotechnology Letters Aims and scope Submit manuscript

Abstract

Vinblastine (VLB) is an antineoplastic agent contained in leaves of Catharanthus roseus. One-pot synthesis of VLB from vindoline and catharanthine, biosynthetic precursors in the plant, was achieved under biomimetic conditions. FMN-mediated coupling of vindoline and catharanthine under irradiation with near-ultraviolet light was followed by NAD(P)H-mediated direct conversion of the coupling product to VLB in the dark. The yield of VLB was governed by the level of NAD(P)H added, and the highest yield was obtained by incubation with 10 mM NAD(P)H for 5 h. It is postulated, as one concept of VLB biosynthesis, that similar non-enzymic VLB synthesis may occur in the plant leaves.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Endo, T., Goodbody, A., Vukovic, J. and Misawa, M. (1987). Phytochem. 26, 3233–3234.

    Google Scholar 

  • Hirata, K., Horiuchi, M., Ando, T., Asada, M., Miyamoto, K. and Miura, Y. (1991). Planta Med. 57, 499–500.

    Google Scholar 

  • Hirata, K., Horiuchi, M., Asada, M. Ando, T., Miyamoto, K. and Miura, Y. (1992). J Ferment. Bioeng. 74, 222–225.

    Google Scholar 

  • Hirata, K., Asada, M., Yatani E., Miyamoto, K. and Miura, Y. (1993). Planta Med. 59, 46–50.

    Google Scholar 

  • Kutney, J. P., Gregonis, D. E., Imhof, R., Itoh, I. and Jahngen, E. (1975). J. Am. Chem. Soc. 97, 5013–5015.

    Google Scholar 

  • Kutney, J. P., Choi, L. S. L., Honda, T., Lewis, N. G., Sato, T., Stuart, K. L. and Worth, B. R. (1982). Helv. Chim. Acta. 65, 2088–2101.

    Google Scholar 

  • Kutney, J. P. (1990). Natural Product Reports, 85–103.

  • Miura, Y., Hirata, K., Kurano, N., Miyamoto, K. and Uchida, K. (1988). Planta Med. 54, 18–20.

    Google Scholar 

  • Morton, J. F. (1977). Periwinkle. In: Major Medicinal Plants, pp. 237–241, Illinois, Charles C. Thomas.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hirata, K., Duangteraprecha, S., Morihara, E. et al. Biomimetic one-pot synthesis of vinblastine: NAD(P)H-mediated vinblastine synthesis from the product of FMN-mediated vindoline–catharanthine coupling under near-ultraviolet light. Biotechnology Letters 19, 53–57 (1997). https://doi.org/10.1023/A:1018367020754

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1018367020754

Keywords

Navigation