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.
Similar content being viewed by others
References
Endo, T., Goodbody, A., Vukovic, J. and Misawa, M. (1987). Phytochem. 26, 3233–3234.
Hirata, K., Horiuchi, M., Ando, T., Asada, M., Miyamoto, K. and Miura, Y. (1991). Planta Med. 57, 499–500.
Hirata, K., Horiuchi, M., Asada, M. Ando, T., Miyamoto, K. and Miura, Y. (1992). J Ferment. Bioeng. 74, 222–225.
Hirata, K., Asada, M., Yatani E., Miyamoto, K. and Miura, Y. (1993). Planta Med. 59, 46–50.
Kutney, J. P., Gregonis, D. E., Imhof, R., Itoh, I. and Jahngen, E. (1975). J. Am. Chem. Soc. 97, 5013–5015.
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.
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.
Morton, J. F. (1977). Periwinkle. In: Major Medicinal Plants, pp. 237–241, Illinois, Charles C. Thomas.
Author information
Authors and Affiliations
Rights 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
Issue Date:
DOI: https://doi.org/10.1023/A:1018367020754