Abstract
A series of flavonoids (1–14) was isolated from the roots of Sophora flavescens. We evaluated their ability to inhibit both microbial growth and sortase A, an enzyme that plays a key role in cell wall protein anchoring and virulence in Staphylococcus aureus. Most prenylated flavonoids (7–13) displayed potent inhibitory activity against gram-positive and gram-negative bacteria except E. coli, with minimum inhibitory concentrations values ranging from 4.40 to 27.7 μM, and weak or no activity against fungal strains tested. Kurarinol (6) was a potent inhibitor of sortase A, with an IC50 value of 107.7 ± 6.6 μM. A preliminary structure-activity relationship, including essential structural requirements, is described.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Cha, J. D., Moon, S. E., Kim, J. Y., Jung, E. K., and Lee, Y. S., Antibacterial activity of sophoraflavanone G isolated from the roots of Sophora flavescens against methicillinresistant Staphylococcus aureus. Phytother. Res., 23, 1326–1331 (2009).
Chen, L., Cheng, X., Shi, W., Lu, Q., Go, V. L., Heber, D., and Ma, L., Inhibition of Streptococcus mutans, methicillinresistant Staphylococcus aureus, and vancomycin-resistant enterococci by kurarinone, a bioactive flavonoid isolated from Sophora flavescens. J. Clin. Microbiol., 43, 3574–3575 (2005).
Cossart, P. and Jongquires, R., Sortase, a universal target for therapeutic agents against Gram-positive bacteria. Proc. Natl. Acad. Sci. U. S. A., 97, 5013–5015 (2000).
Ingham, J. L. and Markham, K. R., Identification of the Erythrina phytolexin cristacarpin and a note on the chirality of other 6a-hydroxypterocarpans. Phytochemistry, 19, 1203–1207 (1980).
Jung, M. J., Kang, S. S., Jung, H. A., Kim, G. J., and Choi, J. S., Isolation of flavonoids and a cerebroside from the stem bark of Alvizzia julibrissin. Arch. Pharm. Res., 27, 593–599 (2004).
Kang, T. H., Jeong, S. J., Ko, W. G., Kim, N. Y., Lee, B. H., Inagaki, M., Miyamoto, T., Higuchi, R., and Kim, Y. C., Cytotoxic lavandulyl flavonones from Sophora flavescens. J. Nat. Prod., 63, 680–681 (2000).
Kim, D. W., Chi, Y. S., Son, K. H., Chang, H. W., Kim, J. S., Kang, S. S., and Kim, H. P., Effects of sophoraflavanone G, a prenylated flavonoid from Sophora flavescens, on cyclooxygenase-2 and in vivo inflammatory response. Arch. Pharm. Res., 25, 329–335 (2002).
Kim, S. H., Shin, D. S., Oh, M. N., Chung, S. C., Lee, J. S., Chang, I. M., and Oh, K. B., Inhibition of sortase, a bacterial surface protein anchoring transpeptidase, by betasitosterol-3-O-glucopyranoside from Fritillaria verticillata. Biosci. Biotechnol. Biochem., 67, 2477–2479 (2003).
Kim, S. H., Shin, D. S., Oh, M. N., Chung, S. C., Lee, J. S., and Oh, K. B., Inhibition of the bacterial surface protein anchoring transpeptidase sortase by isoquinoline alkaloids. Biosci. Biotechnol. Biochem., 68, 421–424 (2004).
Kinoshita, T., Ichinose, K., Takahashi, C., Ho, F., Wu, J., and Sankawa, U., Chemical studies on Sophora tomentosa. Chem. Pharm. Bull., 38, 2756–2759 (1990).
Kuroyanagi, M., Araka, T., Hirayama, Y., and Hayashi, T., Antibacterial and antiandrogen flavonoids from Sophora flavescens. J. Nat. Prod., 62, 1595–1599 (1999).
Maresso, A. W. and Schneewind, O., Sortase as a target of anti-infective therapy. Pharmacol. Rev., 60, 128–141 (2008).
Mazmanian, S. K., Liu, G., Ton-That, H., and Schneewind, O., Staphylococcus aureus sortase, an enzyme that anchors surface proteins to the cell wall. Science, 285, 760–763 (1999).
Mazmanian, S. K., Liu, G., Lenoy, E. R., and Schneewind, O., Staphylococcus aureus sortase mutants defective in the display of surface proteins and in the pathogenesis of animal infections. Proc. Natl. Acad. Sci. U. S. A., 97, 5510–5515 (2000).
Mazmanian, S. K., Skaar, E. P., Gaspar, A. H., Humayun, M., Gornicki, P., Jelenska, J., Joachmiak, A., Missiakas, D. M., and Schneewind, O., Passage of heme-iron across the envelope of Staphylococcus aureus. Science, 299, 906–909 (2003).
Miller, R. W., Kleiman, R., Powell, R. G., and Putnam, A. R., Germination and growth inhibitors of Alfalfa. J. Nat. Prod., 51, 328–330 (1988).
Mizuno, M., Iinuma, M., Tanaka, T., Sakakibara, N., Fujikawa, T., Hanioka, S., Ishida, Y., Liu, X. S., and Murata, H., Flavonol glycosides in the roots of Epimedium diphyllum. Phytochemistry, 27, 3645–3647 (1988).
Oh, K. B., Kim, S. H., Lee, J., Cho, W. J., Lee, T., and Kim, S., Discovery of diarylacrylonitriles as a novel series of small molecule sortase A inhibitors. J. Med. Chem., 47, 2418–2421 (2004).
Oh, K. B., Lee, J. H., Chung, S. C., Shin, J., Shin, H. J., Kim, H. K., and Lee, H. S., Antimicrobial activities of the bromophenols from the red alga Odonthalia corymbifera and some synthetic derivatives. Bioorg. Med. Chem. Lett., 18, 104–108 (2008).
Oh, K. B., Ahn, H., Koo, J., Lim, S., Kim, S., Shin, J., and Mar, W., Therapeutic effect of (Z)-3-(2,5-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylonitrile (DMMA) against Staphylococcus aureus infection in a murine model. Biochem. Biophys. Res. Commun., 396, 440–444 (2010).
Park, J. A., Kim, H. J., Jin, C., Lee, K. T., and Lee, Y. S., A new pterocarpan, (-)-maackiain sultate from the roots of Sophora subprostrata. Arch. Pharm. Res., 26, 1009–1013 (2003).
Ryu, S. Y., Kim, S. K., No, Z., and Ahn, J. W., A novel flavonoids from Sophora flavescens. Planta Med., 62, 361–363 (1996).
Ryu, S. Y., Lee, H. S., Kim, Y. K., and Kim, S. H., Determination of isoprenyl and lavandulyl positions of flavonoids from Sophora flavescens by NMR experiment. Arch. Pharm. Res., 20, 491–495 (1997).
Zheng, Y., Yao, J., Shao, X., and Muralee, N., Bio-active compounds from Sophora flavescens Ait. Nongyaoxue Xuebao, 1, 91–93 (1999).
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Oh, I., Yang, WY., Chung, SC. et al. In vitro sortase a inhibitory and antimicrobial activity of flavonoids isolated from the roots of Sophora flavescens. Arch. Pharm. Res. 34, 217–222 (2011). https://doi.org/10.1007/s12272-011-0206-0
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-011-0206-0