Abstract
The bioassay-oriented fractionation of mistletoe crude extracts (MCEE) using 75% ethanol and culture products of mistletoe transformed by Rhodobacter sphaeroides, a photosynthetic bacterium (PSBT), revealed that the high cytotoxic activities were due to the petroleum ether extracts (PEs) and the acid-precipitated proteins from the aqueous extracts (AQs) of MCEE and PSBT. The isolated triterpenes may account for the activities of the PEs of MCEE and PSBT, respectively. Extraction of MCEE using petroleum ether led to the isolation of 3-epi-betulinic acid (1), betulonic acid (2), oleanolic acid (3), and β-amyrin acetate (4), while petroleum ether extraction of PSBT led to the isolation of 1,3,4,betulinic acid (5), erythrodiol (6), and (3β)-olean-12-ene-3,23-diol (7). The PE of PSBT exerted higher cytotoxicity than the PE of MCEE, which was due to the different triterpene contents of these two extracts. The cytotoxic activities of all compounds were tested, and the results revealed that compounds 1, 2, 3, 5, 6, and 7 contributed significantly to the cytotoxicities of both PEs. The AQ of the PSBT exerted almost the same cytotoxic activity and lower toxicity compared to the AQ of the MCEE. These findings indicate that mistletoe products biotransformed by R. sphaeroides could be used to treat cancers, since they have lower toxicities and higher antitumor activities compared to standard treatments.
Similar content being viewed by others
References
Anderson, L. A., & Phillipson, J. D. (1982). The Pharmaceutical Journal, 229, 427–439.
Park, J. H., Hyun, C. K., & Shin, H. K. (1998). Cancer Letters, 126, 43–48. doi:10.1016/S0304-3835(97)00526-0.
Deeni, Y. Y., & Sadiq, N. M. (2002). Journal of Ethnopharmacology, 83, 235–240. doi:10.1016/S0378-8741(02)00244-1.
Fernández, T., Zolezzi, P. C., Aulicino, P., Caldas Lopes, E., Wagner, M., Ricco, R., et al. (2003). Journal of Ethnopharmacology, 85, 81–92. doi:10.1016/S0378-8741(02)00361-6.
Sun, Y. Q., Liu, K., Wang, S. Y., & Xu, S. Q. (2000). Chinese Traditional and Herbal Drugs, 31, 471–474.
Peng, H. Y., Zhang, Y. H., & Han, Y. (2005). China Journal of Chinese Materia Medica, 30, 381–382.
Khwaja, T. A., Varven, J. C., & Pentecost, S. (1980). Experientia, 36, 599–600. doi:10.1007/BF01965825.
Tanskul, S., Oda, K., Oyama, H., Noparatnaraporn, N., Tsunemi, M., & Takada, K. (2003). Biochemical and Biophysical Research Communications, 309, 547–551. doi:10.1016/j.bbrc.2003.08.035.
Steiger, S., Mazet, A., & Sandmann, G. (2003). Archives of Biochemistry and Biophysics, 414, 51–58. doi:10.1016/S0003-9861(03)00099-7.
Choi, H. P., Hong, J. W., Rhee, K. H., & Sung, H. C. (2004). FEMS Microbiology Letters, 236, 175–181. doi:10.1111/j.1574-6968.2004.tb09644.x.
Rehm, B. H., & Steinbüchel, A. (1999). International Journal of Biological Macromolecules, 25, 3–19. doi:10.1016/S0141-8130(99)00010-0.
Ceng, Y., & Duan, Q. H. (2001). Biotechnology, 11, 44–46.
Aruoma, O. I., Deiana, M., Rosa, A., Casu, V., Piga, R., Peccagnini, S., et al. (2002). Toxicology Letters, 135, 209–217. doi:10.1016/S0378-4274(02)00261-8.
Gao, L., Zhang, Z. M., & Yang, G. E. (2004). Journal of the Shanxi Medical University, 35, 8–9.
Yang, G. E., & Zhang, Z. M. (2006). Microbiology, 33, 40–43.
Yao, Z. Y., & Zhang, Z. M. (1996). Chinese Journal of Applied and Environmental Biology, 2, 84–89.
Tian, Z., Yang, M. S., Huang, F., Li, K. G., Si, J. Y., Shi, L., et al. (2005). Cancer Letters, 226, 65–75. doi:10.1016/j.canlet.2004.11.019.
He, X. G., Wang, X. L., Liu, B., Su, L. N., Wang, G. H., Qu, G. X., et al. (2005). Journal of Molecular Catalysis. B, Enzymatic, 35, 33–40. doi:10.1016/j.molcatb.2005.05.001.
Herz, W., Santhanam, P. S., & Wahlberg, I. (1972). Phytochemistry, 11, 3061–3063. doi:10.1016/0031-9422(72)80106-7.
Sung, T. V., Steglich, W., & Adam, G. (1991). Phytochemistry, 30, 2349–2356. doi:10.1016/0031-9422(91)83647-4.
Ito, J., Chang, F. R., Wang, H. K., Park, Y. K., Ikegaki, M., Kilgore, N., et al. (2001). Journal of Natural Products, 64, 1278–1281. doi:10.1021/np010211x.
Yagi, A., Okamura, N., Haraguchi, Y., Noda, K., & Nishioka, I. (1978). Chemical and Pharmaceutical Bulletin, 26, 3075–3079.
Tori, K., Soe, S., & Shimaoka, A. (1974). Tetrahedron Letters, 48, 4227–4230. doi:10.1016/S0040-4039(01)92128-8.
Maillard, M., Adewunmi, C. O., & Hostettmann, K. (1992). Phytochemistry, 31, 1321–1323. doi:10.1016/0031-9422(92)80500-E.
Yuan, H. Q., & Zuo, C. X. (1992). Acta Pharmacologica Sinica, 27, 589–594.
Bhattacharyya, J., & Barros, C. B. (1986). Phytochemistry, 25, 274–276. doi:10.1016/S0031-9422(00)94550-3.
Yang, Y. J., Chen, H. Y., Lin, J. H., Li, M. Z., Xu, L. H., & Qiu, G. Q. (2007). Journal of Guangzhou University of Traditional Chinese Medicine, 24, 158–161.
Wang, D. Z., Pu, X. Y., Fu, J., & Yang, C. R. (1983). Acta Botanica Yunnica, 5, 437–442.
Ogihara, K., Higa, M., Hokama, K., & Suga, T. (1987). Phytochemistry, 26, 783–785. doi:10.1016/S0031-9422(00)84786-X.
Wang, K. W., Sun, H. X., Wu, B., & Pan, Y. J. (2005). Helvetica Chimica Acta, 88, 990–995. doi:10.1002/hlca.200590094.
Tanaka, R., Tabuse, M., & Matsunaga, S. (1988). Phytochemistry, 27, 3563–3567. doi:10.1016/0031-9422(88)80769-6.
Zong, W., Xia, W. S., & Cui, B. L. (2005). Food Science, 26, 222–225.
Wang, C. Q., Li, Y. L., & Li, D. C. (1994). A course of senior biochemistry experiments (1st ed.). Beijing, China: Beijing University Press.
Nunes, M. J., Reyes, C. P., Jimenez, I. A., Moujir, L., & Bazzocchi, I. L. (2005). Journal of Natural Products, 68, 1018–1021. doi:10.1021/np058016w.
Chiang, L. C., Chiang, W., Chang, M. Y., Ng, L. T., & Lin, C. C. (2003). The American Journal of Chinese Medicine, 31, 37–46. doi:10.1142/S0192415X03000825.
Liu, J. (2005). Journal of Ethnopharmacology, 100, 92–94. doi:10.1016/j.jep.2005.05.024.
Ohsaki, A., Imai, Y., Naruse, M., Ayabe, S., Komiyama, K., & Takashima, J. (2004). Journal of Natural Products, 67, 469–471. doi:10.1021/np030379d.
Chiang, Y. M., Chang, J. Y., Kuo, C. C., Chang, C. Y., & Kuo, Y. H. (2005). Phytochemistry, 66, 495–501. doi:10.1016/j.phytochem.2004.12.026.
Park, J. H., Hyun, C. K., & Shin, H. K. (1998). Cancer Letters, 126, 43–48. doi:10.1016/S0304-3835(97)00526-0.
Silver, S. (2001). The Lancet Oncology, 2, 196. doi:10.1016/S1470-2045(00)00286-2.
Bauer, C., Oppel, T., Ruëff, F., & Przybilla, B. (2005). Annals of Allergy, Asthma & Immunology, 94, 86–89.
Timoshenko, A. V., Lan, Y., Gabius, H. J., & Lala, P. K. (2001). European Journal of Cancer, 37, 1910–1920. doi:10.1016/S0959-8049(01)00156-3.
Shanker, V., Rayabandla, S. M., Kumavath, R. N., Chintalapati, S., & Chintalapati, R. (2006). Current Microbiology, 52, 413–417. doi:10.1007/s00284-005-0057-3.
Acknowledgements
We thank Dr. Qingshan Li (School of Pharmaceutical Sciences, Shanxi Medical University, China) for his kind help. Financial support was provided by the National Natural Science Foundation of China (grant no. 30672621), the Shanxi Provincial Natural Science Foundation (grant no. 2006011099), the Provincial Key Technology R&D Program of Shanxi Province, China (grant no. 051081), and the National Key Technologies Research and Development Program of China (grant no. 2001BA540C). This paper was extensive edited by a native English professional with science background at Elixigen Corporation.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Yang, GE., Chen, B., Zhang, Z. et al. Cytotoxic Activities of Extracts and Compounds from Viscum coloratum and its Transformation Products by Rhodobacter sphaeroides . Appl Biochem Biotechnol 152, 353–365 (2009). https://doi.org/10.1007/s12010-008-8372-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12010-008-8372-3