Abstract
Valdecoxib is a new anti-inflammatory drug that is highly selective for inhibition of the inducible form of cyclooxygenase (COX-2). In the present study, biotransformation of valdecoxib was investigated in cell cultures of five medicinal plants, viz., Catharanthus roseus, Azadirachta indica, Capsicum annuum, Ervatamia heyneana, and Nicotiana tabacum. Identification of the biotransformed products was carried out by using high-performance liquid chromatography coupled with diode array detection and liquid chromatography–tandem mass spectrometry analysis. All the cultures transformed valdecoxib into more polar compounds, and C. roseus also produced one unknown compound that is less polar than the substrate. The reactions performed by these plant cell cultures include hydroxylation, methylation, and demethylation. Optimization studies were performed to investigate the effect of the day of extraction and substrate concentration on biotransformation.
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Ishihara, K., Hamada, H., Hirata, T., & Nakajima, N. (2003). Journal of Molecular Catalysis. B, Enzymatic, 23, 145–170.
Talley, J. J., Brown, D. L., Carter, J. S., Graneto, M. J., Koboldt, C. M., Masferrer, J. L., et al. (2000). Journal of Medicinal Chemistry, 43, 775–777.
Yuan, J. J., Yang, D., Zhang, J. Y., Bible Jr., R., Karim, A., & Findlay, J. W. A. (2002). Drug Metabolism and Disposition, 30, 1013–1021.
Suga, T., Hirata, T., & Lee, Y. S. (1982). Chemistry Letters, 11, 1595–1597.
Hirata, T., Yoshihiro, I., Izumi, S., Shimoda, K., Hamada, H., & Kawamura, T. (1994). Phytochemistry, 37, 401–403.
Eikert, H., Karasinska, T., & Kohlnunzer, S. (1983). Herba Hungarica, 22, 29–32.
Hao, D. H., & Yeoman, M. M. (1998). Journal of Plant Physiology, 152, 420–426.
Hamada, H., Fuchikami, Y., Jansinj, R. L., & Kaminsky, L. S. (1993). Phytochemistry, 33, 599–600.
Yagen, B., Gallili, G. E., & Matcles, R. I. (1978). Applied and Environmental Microbiology, 36, 213–216.
Dagnino, D., Schripsema, J., & Verpoorte, R. (1994). Phytochemistry, 35, 671–676.
Keshetty, S., Venisetty, R. K., Molmoori, V., & Ciddi, V. (2006). Pharmazie, 61, 245–246.
Zhang, J. Y., Yuan, J. J., Wang, Y., Bible Jr., R. H., & Breau, A. P. (2003). Drug Metabolism and Disposition, 31, 491–501.
Balaji, K., Veeresham, C., Srisilam, K., & Kokate, C. K. (2003). Journal of Plant Biotechnology, 5, 121–129.
Ravi Gopal, N. (1998). M. Pharm Thesis, Kakatiya University, Warangal, India.
Min, Y., Lili, N., Jixun, Z., Hongzhu, G., & Dean, G. (2003). Journal of Molecular Catalysis. B, Enzymatic, 22, 89–95.
Sumalatha, D. V. (2001). M. Pharm Thesis, Kakatiya University, Warangal, India.
Acknowledgements
The authors are thankful to Dr. Ramesh Mullangi and Mr. Raj Kallem, Discovery Research, Dr. Reddy’s Laboratories, Hyderabad, for recording LC-MS-MS spectra. The authors are also thankful to Dr. A.V.S.R. Swamy, Senior Scientist, Central Tobacco Research Institute, Guntur, for providing the seeds of N. tabacum and Mepro Pharmaceuticals, Ahmedabad, for providing the valdecoxib gift sample. One of the authors, Molmoori, is thankful to All India Council for Technical Education, New Delhi, India, for providing fellowship.
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Molmoori, V., Srisailam, K. & Ciddi, V. Biotransformation of Valdecoxib by Plant Cell Cultures. Appl Biochem Biotechnol 144, 201–212 (2008). https://doi.org/10.1007/s12010-007-8102-2
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DOI: https://doi.org/10.1007/s12010-007-8102-2