Abstract
As part of our ongoing search for natural sources of therapeutic and preventive agents for diabetic complications, we evaluated the inhibitory effects of components of the fruit of Xanthium strumarium (X. strumarium) on aldose reductase (AR) and galactitol formation in rat lenses with high levels of glucose. To identify the bioactive components of X. strumarium, 7 caffeoylquinic acids and 3 phenolic compounds were isolated and their chemical structures were elucidated on the basis of spectroscopic evidence and comparison with published data. The abilities of 10 X. strumarium-derived components to counteract diabetic complications were investigated by means of inhibitory assays with rat lens AR (rAR) and recombinant human AR (rhAR). From the 10 isolated compounds, methyl-3,5-di-O-caffeoylquinate showed the most potent inhibition, with IC50 values of 0.30 and 0.67 μM for rAR and rhAR, respectively. In the kinetic analyses using Lineweaver–Burk plots of 1/velocity and 1/substrate, methyl-3,5-di-O-caffeoylquinate showed competitive inhibition of rhAR. Furthermore, methyl-3,5-di-O-caffeoylquinate inhibited galactitol formation in the rat lens and in erythrocytes incubated with a high concentration of glucose, indicating that this compound may be effective in preventing diabetic complications.
Similar content being viewed by others
References
Agata, I., S. Goto, T. Hatano, S. Nishibe, and T. Okuda. 1993. 1,3,5-Tri-O-Caffeoylquinic acid from Xanthium Strumarium. Phytochemistry 33: 508–509.
Brownlee, M. 2001. Biochemistry and molecular cell biology of diabetic complications. Nature 414: 813–820.
Brownlee, M. 2005. The pathobiology of diabetic complications: a unifying mechanism. Diabetes 54: 1615–1625.
Carnat, A., A. Heitz, D. Fraisse, A.P. Carnat, and J.L. Lamaison. 2000. Major dicaffeoylquinic acids from Artemisia vulgaris. Fitoterapia 71: 587–589.
Choi, S.Z., S.O. Lee, S.U. Choi, and K.R. Lee. 2003. A new sesquiterpene hydroperoxide from the aerial parts of Aster oharai. Archives of Pharmacal Research 26: 521–525.
Cui, C.B., S.K. Jeong, Y.S. Lee, S.O. Lee, I.J. Kang, and S.S. Lim. 2009. Inhibitory Activity of Caffeoylquinic Acids from the Aerial Parts of Artemisia princeps on Rat Lens Aldose Reductase and on the Formation of Advanced Glycation End Products. Journal of the Korean Society for Applied Biological Chemistry 52: 655–662.
Dai, Y.H., Z. Cui, J.L. Li, and D. Wang. 2008. A new thiaziedione from the fruits of Xanthium sibiricum. Journal of Asian Natural Products Research 10: 343–347.
Danino, O., H.E. Gottlieb, S. Grossman, and M. Bergman. 2009. Antioxidant activity of 1,3-dicaffeoylquinic acid isolated from Inula viscose. Journal of Food Research 42: 1273–1280.
de la Fuente, J.A., and S. Manzanaro. 2003. Aldose reductase inhibitors from natural sources. Natural Products Reports 20: 243–251.
Engerman, R.L., and T.S. Kern. 1984. Experimental galactosemia produces diabetic-like retinopathy. Diabetes 33: 97–100.
Han, T., H.L. Li, Q.Y. Zhang, P. Han, H.C. Zheng, K. Rahman, and L.P. Qin. 2007. Bioactivity-guided fractionation for anti-inflammatory and analgesic properties and constituents of Xanthium strumarium L. Phytomedicine 14: 825–829.
Haraguchi, H., I. Ohmi, A. Fukuda, Y. Tamura, K. Mizutani, O. Tanaka, and W.H. Chou. 1997. Inhibition of aldose reductase and sorbitol accumulation by astilbin and taxifolin dihydroflavonols in Engelhardtia chrysolepis. Bioscience, Biotechnology, and Biochemistry 61: 651–654.
Hayman, S., and J.H. Kinoshita. 1965. Isolation and Properties of Lens Aldose Reductase. Journal of Biological Chemistry 240: 877–882.
Hsu, F.L., Y.C. Chen, and J.T. Cheng. 2000. Caffeic acid as active principle from the fruit of Xanthium strumarium to lower plasma glucose in diabetic rats. Planta Medica 66: 228–230.
Jacubert, M., O. Provot, J.F. Peyrat, A. Hamze, J.D. Brion, and M. Alami. 2010. p-Toluenesulfonic acid-promoted selective functionalization of unsymmetrical arylalkynes: a regioselective access to various arylketones and heterocycles. Tetrahedron 66: 3775–3787.
Jung, H.A., M.D. Islam, Y.S. Kwon, S.E. Jin, Y.K. Son, J.J. Park, H.S. Sohn, and J.S. Choi. 2011. Extraction and identification of three major aldose reductase inhibitors from Artemisia Montana. Food and Chemical Toxicology 49: 376–384.
Kador, P.F., J.H. Kinoshita, W.H. Tung, and L.T. Chylack Jr. 1980. Differences in the susceptibility of various aldose reductases to inhibition. II. Investigative Ophthalmology & Visual Science 19: 980–982.
Kador, P.F. 1988. The role of aldose reductase in the development of diabetic complications. Medicinal Research Reviews 8: 325–352.
Kang, J.H., M.Y. Choi, S.M. Kang, H.N. Kwon, H. Wen, C.H. Lee, M.S. Park, H.J. Wiklund Susanne Kim, S.W. Kwon, and S.H. Park. 2008. Application of a 1H Nuclear Magnetic Resonance (NMR) Metabolomics Approach Combined with Orthogonal Projections to Latent Structure-Discriminant Analysis as an Efficient Tool for Discriminating between Korean and Chinese Herbal Medicines. Journal of Agricultural and Food Chemistry 56: 11589–11595.
Kawanishi, K., H. Ueda, and M. Moriyasu. 2003. Aldose reductase inhibitors from the nature. Current Medicinal Chemistry 10: 1353–1374.
Kwang-Hyok, S., P. Ui-Nam, C. Sarkar, and R. Bhadra. 2005. A sensitive assay of red blood cell sorbitol level by high performance liquid chromatography: potential for diagnostic evaluation of diabetes. Clinica Chimica Acta 354: 41–47.
Lavault, M., A. Landreau, G. Larcher, J.P. Bouchara, F. Pagniez, P. Le Pape, and P. Richomme. 2005. Antileishmanial and antifungal activities of xanthanolides isolated from Xanthium macrocarpum. Fitoterapia 76: 363–366.
Lee, E.H., D.G. Song, J.Y. Lee, C.H. Pan, B.H. Um, and S.H. Jung. 2008a. Inhibitory effect of the compounds isolated from Rhus verniciflua on aldose reductase and advanced glycation endproducts. Biological and Pharmaceutical Bulletin 31: 1626–2630.
Lee, Y.S., Y.H. Kang, J.Y. Jung, I.J. Kang, S.N. Han, J.S. Chung, H.K. Shin, and S.S. Lim. 2008b. Inhibitory constituents of aldose reductase in the fruiting body of Phellinus linteus. Biological and Pharmaceutical Bulletin 31: 765–768.
Lee, Y.S., S.H. Kim, S.H. Jung, J.K. Kim, C.H. Pan, and S.S. Lim. 2010. Aldose reductase inhibitory compounds from Glycyrrhiza uralensis. Biological and Pharmaceutical Bulletin 33: 917–921.
Ma, Y.T., M.C. Huang, F.L. Hsu, and H.F. Chang. 1998. Thiazinedione from Xanthium strumarium. Phytochemistry 48: 1083–1085.
Sang, S., K. Lapsley, R.T. Rosen, and C.T. Ho. 2002. New Prenylated Benzoic Acid and Other Constituents from Almond Hulls (Prunus amygdalus Batsch). Journal of Agricultural and Food Chemistry 50: 607–609.
Yabe-Nishimura, C. 1998. Aldose reductase in glucose toxicity: a potential target for the prevention of diabetic complications. Pharmacological Reviews 50: 21–33.
Zhu, X., X. Dong, Y. Wang, P. Ju, and S. Luo. 2005. Phenolic compounds from Viburnum cylindricum. Helvetica Chimica Acta 88: 339–342.
Acknowledgments
This research was supported by Basic Science Research Program through the National Research Foundation of Korea(NRF) funded by the Ministry of Education, Science and Technology (2012-008842 & 2012RJA6A1048184) and by Business for Cooperative R&D between Industry, Academy, and Research Institute funded Korea Small and Medium Business Administration in 2011 (No. 47385).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Yoon, H.N., Lee, M.Y., Kim, JK. et al. Aldose Reductase Inhibitory Compounds from Xanthium strumarium . Arch. Pharm. Res. 36, 1090–1095 (2013). https://doi.org/10.1007/s12272-013-0123-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-013-0123-5