Abstract
In an ongoing project directed toward the discovery of novel treatments for diabetic complications from traditional herbal medicines, fifteen compounds, apigenin (1), apigenin-7-O-β-d-glucopyranoside (2), apigenin-7-O-(6″-O-acetyl)-β-d-glucopyranoside (3), luteolin (4), luteolin-7-O-β-d-glucopyranoside (5), luteolin-7-O-(6″-O-acetyl)-β-d-glucopyranoside (6), isorhamnetin-3-Oneohesperidoside (7), 4-O-caffeoylquinic acid (8), chlorogenic acid methyl ester (9), 4-O-β-d-glucopyranosylcaffeic acid (10), lobetyolin (11), cordifolioidyne C (12), isomultiflorenyl acetate (13), β-sitosterol glucoside (14), and α-spinosterol (15), were isolated from an EtOAc-soluble fraction of the flowers of Platycodon grandiflorum (balloonflower; Campanulaceae). The structures of the compounds were identified by physical and spectroscopic methods, as well as by comparison of their data with literature values. All the isolates were evaluated in vitro for inhibitory activity on the formation of advanced glycation end products and rat lens aldose reductase.
Similar content being viewed by others
References
Ahmed, N., Advanced glycation endproducts-role in pathology of diabetic complications. Diabetes Res. Clin. Pract., 67, 3–21 (2005).
Bae, K., The Medicinal Plants of Korea. Kyo-Hak Publishing Co., Seoul, pp. 485, (2002).
Beyer-Mears, A. and Cruz, E., Reversal of diabetic cataract by sorbinil, an aldose reductase inhibitor. Diabetes, 34, 15–21 (1985).
Brownlee M., The pathobiology of diabetic complications: a unifying mechanism. Diabetes, 54, 1615–1625 (2005).
Chaurasia, N. and Wichtl, M., Flavonol glycosides from Urtica dioica. Planta Med., 53, 432–434 (1987).
Choi, S. Z., Lee, S. O., Choi, S. U., and Lee, K. R., A new sesquiterpene hydroperoxide from the aerial parts of Aster oharai. Arch. Pharm. Res., 26, 521–525 (2003).
Cui, C. -B., Tezuka, Y., Kikuchi, T., Nakano, H., Tamaoki, T., and Park, J. -H., Constituent of a fern, Davallia mariesii Moore. I. Isolation and structures of davallialactone and a new glucuronide. Chem. Pharm. Bull., 38, 3218–3225 (1990).
Cui, C. -B., Jeong, S. K., Lee, Y. S., Lee, S. O., Kang, I. -J., and Lim, S. S., Inhibitory activity of caffeoylquinic acids from the aerial parts of Artemisia princeps on rat lens aldose reductas and on the formation of advanced glycation end products. J. Korean Soc. Appl. Biol. Chem., 52, 655–662 (2009).
Dufrane, S. P., Malaisse, W. J., and Sener, A., A micromethod for the assay of aldose reductase, its application to pancreatic islets. Biochem. Med., 32, 99–105 (1984).
Engerman, R. L. and Kern, T. S., Experimental galactosemia produces diabetes-like retinopathy. Diabetes, 33, 97–100 (1984).
Faure, R. and Gaydou, E. M., Application of inverse-detected two-dimensional heteronuclear-correlated NMR spectroscopy to the complete carbon-13 assignment of isomultiflorenyl acetate. J. Nat. Prod., 54, 1564–1569 (1991).
Han, X. H., Hong, S. S., Hwang, J. S., Lee, M. K., Hwang, B. Y., and Ro, J. S., Monoamine oxidase inhibitory components from Cayratia japonica. Arch. Pharm. Res., 30, 13–17 (2007).
Ishimaru, K., Yonemitsu, H., and Shimomura, K., Lobetyolin and lobetyol from hairy root culture of Lobelia inflata. Phytochemistry, 30, 2255–2257 (1991).
Jang, D. S., Lee, G. Y., Kim, Y. S., Lee, Y. M., Kim, C. S., Yoo, J. L., and Kim, J. S., Anthraquinones from the seeds of Cassia tora with inhibitory activity on protein glycation and aldose reductase. Biol. Pharm. Bull., 30, 2207–2210 (2007).
Jang, D. S., Yoo, N. H., Lee, Y. M., Yoo, J. L., Kim, Y. S., and Kim, J. S., Constituents of the flowers of Erigeron annuus with inhibitory activity on the formation of advanced glycation end products (AGEs) and aldose reductase. Arch. Pharm. Res., 31, 900–904 (2008).
Jung, H. A., Park, J. C., Chung, H. Y., Kim, J., and Choi, J. S., Antioxidant flavonoids and chlorogenic acid from the leaves of Eriobotrya japonica. Arch. Pharm. Res., 22, 213–218 (1999).
Kim, Y. S., Kim, N. H., Lee, S. W., Lee, Y. M., Jang, D. S., and Kim, J. S., Effect of protocatechualdehyde on receptor for advanced glycation end products and TGF-β1 expression in human lens epithelial cells cultured under diabetic conditions and on lens opacity in streptozotocindiabetic rats. Eur. J. Pharmacol., 569, 171–179 (2007).
Lee, J. Y., Chang, E. J., Kim, H. J., Park, J. H., and Choi, S. W., Antioxidant flavonoids from leaves of Carthamus tinctorius. Arch. Pharm. Res., 25, 313–319 (2002).
Lee, S., Kim, K. S., Jang, J. M., Park, Y., Kim, Y. B., and Kim, B. -K., Phytochemical constituents from the herba of Artemisia apiacea. Arch. Pharm. Res., 25, 285–288 (2002).
Lee, Y. H., Lee, I. R., Won, W. S., and Park, C. H., Flavonoids of Elscholtzia cristata. Arch. Pharm. Res., 11, 247–249 (1988).
Logendra, S., Ribnicky, D. M., Yang, H., Poulev, A., Ma, J., Kennelly, E. J., and Raskin, I., Bioassay-guided isolation of aldose reductase inhibitors from Artemisia dracunculus. Phytochemistry, 67, 1539–1546 (2006).
Matsuda, H., Morikawa, T., Toguchida, I., and Yoshikawa, M., Structural requirements of flavonoids and related compounds for aldos reductase inhibitory activity. Chem. Pharm. Bull., 50, 788–795 (2002).
Matsuda, H., Wang, T., Managi, H., and Yoshikawa, M., Structural requirements of flavonoids for inhibition of protein glycation and radical scavenging activities. Bioorg. Med. Chem., 11, 5317–5323 (2003).
Mei, R. -Q., Lu, Q., Hu, Y. -F., Liu, H. -Y., Bao, F. -K., Zhang, Y., and Cheng, Y. -X., Three new polyyne (= polyacetylene) glucosides from the edible roots of Codonopsis cordifolioidea. Helv. Chim. Acta, 91, 90–96 (2008).
Peyroux, J. and Sternberg, M., Advanced glycation endproducts (AGEs): pharmacological inhibition in diabetes, Pathol. Biol., 54, 405–419 (2006).
Reddy, V. P. and Beyaz, A., Inhibitors of the Maillard reaction and AGE breakers as therapeutic s for multiple diseases. Drug Discov. Today, 11, 646–654 (2006).
Švehlíková, V., Bennet, R. N., Mellon, F. A., Needs, P. W., Piacente, S., Kroon, P. A., Bao, Y., Isolation, identification and stability of acylated derivatives of apigenin 7-O-glucoside from chamomile (Chamomilla recutita [L.] Rauschert). Phytochemistry, 65, 2323–2332 (2004).
Takeuchi, M. and Yamagishi, S., Possible involvement of advanced glycation end-products (AGEs) in the pathogenesis of Alzheimer’s disease. Curr. Pharm. Des., 14, 973–978 (2008).
Tatefuji, T., Izumi, N., Ohta, T., Arai, S., Ikeda, M., and Kurimoto, M., Isolation and identification of compounds from Brazilian propolis which enhance macrophage spreading and mobility. Biol. Pharm. Bull., 19, 966–970 (1996).
Tomlinson, D. R., Stevens, E. J., and Diemel, L. T., Aldose reductase inhibitors and their potential for the treatment of diabetes complications. Trends Pharmacol. Sci., 15, 292–298 (1994).
Yabe-Nishimura, C., Aldose reductase in glucose toxicity: a potential target for the prevention of diabetic complications. Pharmacol. Rev., 50, 21–33 (1998).
Yoo, N. H., Jang, D. S., Yoo, J. L., Lee, Y. M., Kim, Y. S., Cho, J. H., and Kim, J. S., Erigeroflavanone, a flavanone derivative from the flowers of Erigeron annuus with protein glycation and aldose reductase inhibitory activity. J. Nat. Prod., 71, 713–715 (2008).
Yoshikawa, M., Morikawa, T., Murakami, T., Toguchida, I., Harima, S., and Matsuda, H., Medicinal flowers. I. Aldose reductase inhibitors and three new eudesmane-type sesquiterpenes, kikkanols A, B, and C, from the flowers of Chrysanthemum indicum L. Chem. Pharm. Bull., 47, 340–345 (1999).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Jang, D.S., Lee, Y.M., Jeong, I.H. et al. Constituents of the flowers of Platycodon grandiflorum with inhibitory activity on advanced glycation end products and rat lens aldose reductase in vitro . Arch. Pharm. Res. 33, 875–880 (2010). https://doi.org/10.1007/s12272-010-0610-x
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-010-0610-x