Abstract
Phytochemical investigation of the stem barks of Canarium bengalense (Burseraceace) resulted in the isolation of a new flavone glycoside (5) together with six known compounds (1–4, 6, and 7). The chemical structure of the new compound was elucidated as 3′-hydroxy-7,4′-dimethoxyflavone-5-O-α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside by means of 1D and 2D NMR (1H-1H COSY, HMQC, and HMBC) and MS analyses. To evaluate the in vitro cytoprotective effect, the isolates (1-7) were tested against hydrogen peroxide (H2O2)-induced damage in primary cultured hepatocytes. The viability of hepatocytes was increased by treatment with each compound, except compound 1. Compounds 3, 4, and 7 exerted cytoprotective effects comparable to curcumin, the positive control. Our results suggest that the cytoprotective constituents of C. bengalense may contribute to its traditional use in the treatment of tumor and liver damage.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Encyclopedia of Chinese Material Medica (Zhong Yao Da Zi Dian), Jiang Su New Medical College (Ed.). Shanghai Science and Technology, p. 2598 (1977).
Fernandez-Checa, J. C. and Kaplowitz, N., Hepatic mitochondrial glutathione: transport and role in disease and toxicity. Toxicol. Appl. Pharm., 204, 263–273 (2005).
Fuchino, H., Satoh, T., and Tanaka, N., Evaluation of Betula Species in Japan. I. Constituents of Betula ermanii. Chem. Pharm. Bull. (Tokyo), 43, 1937–1942 (1995).
Holownia, A. and Braszko, J. J., Tamoxifen cytotoxicity in hepatoblastoma cells stably transfected with human CYP3A4. Biochem. Pharmacol., 67, 1057–1064 (2004).
Latza, S., Ganber, D., and Berger, R. G., Carbohydrate esters of cinnamic acid from fruits of Physalis Peruviana, Psidium Guajava and Vaccinium Vitis-Idaea. Phytochemistry, 43, 481–485 (1996).
Lee, M. K., Sung, S. H., Lee, H. S., Cho, J. H., and Kim, Y. C., Lignan and neolignan glycosides from Ulmus davidiana var. japonica. Arch. Pharm. Res., 24, 198–201 (2001).
Lee, M.-W., Tanaka, T., Nonaka, G.-I., and Hahn, D.-R., Phenolic compounds on the leaves of Betula platyphylla var. latifolia. Arch. Pharm. Res., 15, 211–214 (1992).
Li, H., Zhou, C., Pan, Y., Gao, X., Wu, X., Bai, H., Zhou, L., Chen, Z., Zhang, S., Shi, S., Luo, J., Xu, J., Chen, L., Zheng, X., and Zhao, Y., Evaluation of antiviral activity of compounds isolated from Ranunculus sieboldii and Ranunculus sceleratus. Planta Med., 71, 1128–1133 (2005).
Sinha, A., Taylor, W. H., Khan, H., McDaniel, S. T., and Esko, J. D., Glycoside Primers of Psittacanthus cucullaris. J. Nat. Prod., 62, 1036–1038 (1999).
Urones, J. G., Teresa, J. P., Marcos, I. S., and Martin, D. D., Ent-isolariciresinol in Reseda suffruticosa. Phytochemistry, 26, 1540–1541 (1987).
Vrba, J. and Modrianský, M., Oxidative burst of kupffer cells: Target for liver injury treatment. Biomed. Pap., 146, 15–20 (2002).
Wu, Z. Y., Raven, P. H., and Hong, D. Y., In Flore of China. Science Press, Beijing, and Missouri Botanical Garden Press, St. Louis, pp. 108–110 (2008).
Zahir, A., Jossang, A., Bodo, B., Provost, J., Cosson, J.-P., and Sevenet, T., Five New Flavone 5-O-Glycosides from Lethedon tannaensis: Lethedosides and Lethediosides. J. Nat. Prod., 62, 241–243 (1999).
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Le, H.T., Ha, D.T., Minh, C.T.A. et al. Constituents from the stem barks of Canarium bengalense with cytoprotective activity against hydrogen peroxide-induced hepatotoxicity. Arch. Pharm. Res. 35, 87–92 (2012). https://doi.org/10.1007/s12272-012-0110-2
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-012-0110-2