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References

  1. Ajdi D, McShan WM, McLaughlin RE, Savi G, Chang J, Carson MB, et al. 2002. Genome sequence of Streptococcus mutans UA159, a cariogenic dental pathogen. Proc. Natl. Acad. Sci. USA 99: 14434-14439.
    Pubmed PMC CrossRef
  2. Colombo PS, Flamini G, Fico G. 2014. Primula latifolia Lapeyr and Primula vulgaris Hudson flavonoids. Nat. Prod. Res. 28: 1641-1644.
    Pubmed CrossRef
  3. Hendrickx AP, Budzik JM, Oh SY, Schneewind O. 2011. Architects at the bacterial surface - sortases and the assembly of pili with isopeptide bonds. Nat. Rev. Microbiol. 9: 166-176.
    Pubmed CrossRef
  4. Hu P, Huang P, Chen WM. 2013. Curcumin inhibits the sortase A activity of the Streptococcus mutans UA159. Appl. Biochem. Biotechnol. 171: 396-402.
    Pubmed CrossRef
  5. Kim JM, Yun-Choi HS. 2008. Anti-platelet effects of flavonoids and flavonoid-glycosides from Sophora japonica. Arch. Pharm. Res. 31: 886-890.
    Pubmed CrossRef
  6. Kite GC, Veitch NC, Boalch ME, Lewis GP, Leon CJ, Simmonds MS. 2009. Flavonol tetraglycosides from fruits of Styphnolobium japonicum (Leguminosae) and the authentication of Fructus Sophorae and Flos Sophorae. Phytochemistry 70:785-794.
    Pubmed CrossRef
  7. Lee KY, Shin D S, Y oon J M, K ang H, Oh KB. 2 02 . Expression of a transpeptidase for cell wall sorting reaction, from sortase, Staphylococcus aureus ATCC 6538p in Escherichia coli. J. Microbiol. Biotechnol. 12: 530-533.
  8. Lee SF, Boran TL. 2003. Roles of sortase in surface expression of the major protein adhesin P1, saliva-induced aggregation and adherence, and cariogenicity of Streptococcus mutans. Infect. Immun. 71: 676-681.
    Pubmed PMC CrossRef
  9. Lévesque CM, Voronejskaia E, Huang YC, Mair RW, Ellen RP, Cvitkovitch DG. 2005. Involvement of sortase anchoring of cell wall proteins in biofilm formation by Streptococcus mutans. Infect. Immun. 73: 3773-3777.
    Pubmed PMC CrossRef
  10. Mazmanian SK, Liu G, Jensen ER, Lenoy E, Schneewind O. 2000. Staphylococcus aureus sortase mutants defective in the display of surface proteins and in the pathogenesis of animal infections. Proc. Natl. Acad. Sci. USA 97: 5510-5515.
    Pubmed PMC CrossRef
  11. Oh KB, Oh MN, Kim JG, Shin DS, Shin J. 2006. Inhibition of sortase-mediated Staphylococcus aureus adhesion to fibronectin via fibronectin-binding protein by sortase inhibitors. Appl. Microbiol. Biotechnol. 70: 102-106.
    Pubmed CrossRef
  12. Sang S, L apsley K, J eong WS, L achance PA, Ho CT, R osen RT. 2002. Antioxidative phenolic compounds isolated from almond skins (Prunus amygdalus Batsch). J. Agric. Food Chem. 50: 2459-2463.
    Pubmed CrossRef
  13. Selwitz RH, I smail AI, Pitts NB. 2 007. D ental caries. Lancet 369: 51-59.
    CrossRef
  14. Ton-That H, Liu G, Mazmanian SK, Faull KF, Schneewind O. 1999. Purification and characterization of sortase, the transpeptidase that cleaves surface proteins of Staphylococcus aureus at the LPXTG motif. Proc. Natl. Acad. Sci. USA 96:12424-12429.
    Pubmed PMC CrossRef
  15. Xu X, Xie H, Hao J, Jiang Y, Wei X. 2011. Flavonoid glycosides from the seeds of Litchi chinensis. J. Agric. Food Chem. 59: 1205-1209.
    Pubmed CrossRef
  16. Yang WY, Won TH, Ahn CH, Lee SH, Yang HC, Shin J, Oh KB. 2015. Streptococcus mutans sortase A inhibitory metabolites from the flowers of Sophora japonica. Bioorg. Med. Chem. Lett. 25: 1394-1397.
    Pubmed CrossRef

Article

Note

J. Microbiol. Biotechnol. 2016; 26(9): 1566-1569

Published online September 28, 2016 https://doi.org/10.4014/jmb.1605.05005

Copyright © The Korean Society for Microbiology and Biotechnology.

Flavonoid Glycosides Inhibit Sortase A and Sortase A-Mediated Aggregation of Streptococcus mutans, an Oral Bacterium Responsible for Human Dental Caries

Woo-Young Yang 1, Chang-Kwon Kim 2, Chan-Hong Ahn 1, Heegyu Kim 1, Jongheon Shin 2 and Ki-Bong Oh 1*

1Department of Agricultural Biotechnology, College of Agriculture and Life Sciences, Seoul National University, Seoul 08826, Republic of Korea, 2Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea

Received: May 4, 2016; Accepted: June 10, 2016

Abstract

Three flavonoids were isolated from dried flowers of Sophora japonica using repetitive column
chromatography and high-performance liquid chromatography. The flavonoids were identified
as rutin (1), quercetin-3’-O-methyl-3-O-α-L-rhamnopyranosyl(1 → 6)-β-D-glucopyranoside (2),
and quercetin (3) on the basis of spectroscopic analysis and comparison of values reported in
the literature. These compounds inhibited the action of sortase A (SrtA) from Streptococcus
mutans, a primary etiologic agent of human dental caries. The onset and magnitude of
inhibition of saliva-induced aggregation of S. mutans treated with compound 1 was
comparable to that of untreated S. mutans with a deletion of the srtA gene.

Keywords: Sophora japonica, flavonoids, Streptococcus mutans, sortase A, cell aggregation

References

  1. Ajdi D, McShan WM, McLaughlin RE, Savi G, Chang J, Carson MB, et al. 2002. Genome sequence of Streptococcus mutans UA159, a cariogenic dental pathogen. Proc. Natl. Acad. Sci. USA 99: 14434-14439.
    Pubmed KoreaMed CrossRef
  2. Colombo PS, Flamini G, Fico G. 2014. Primula latifolia Lapeyr and Primula vulgaris Hudson flavonoids. Nat. Prod. Res. 28: 1641-1644.
    Pubmed CrossRef
  3. Hendrickx AP, Budzik JM, Oh SY, Schneewind O. 2011. Architects at the bacterial surface - sortases and the assembly of pili with isopeptide bonds. Nat. Rev. Microbiol. 9: 166-176.
    Pubmed CrossRef
  4. Hu P, Huang P, Chen WM. 2013. Curcumin inhibits the sortase A activity of the Streptococcus mutans UA159. Appl. Biochem. Biotechnol. 171: 396-402.
    Pubmed CrossRef
  5. Kim JM, Yun-Choi HS. 2008. Anti-platelet effects of flavonoids and flavonoid-glycosides from Sophora japonica. Arch. Pharm. Res. 31: 886-890.
    Pubmed CrossRef
  6. Kite GC, Veitch NC, Boalch ME, Lewis GP, Leon CJ, Simmonds MS. 2009. Flavonol tetraglycosides from fruits of Styphnolobium japonicum (Leguminosae) and the authentication of Fructus Sophorae and Flos Sophorae. Phytochemistry 70:785-794.
    Pubmed CrossRef
  7. Lee KY, Shin D S, Y oon J M, K ang H, Oh KB. 2 02 . Expression of a transpeptidase for cell wall sorting reaction, from sortase, Staphylococcus aureus ATCC 6538p in Escherichia coli. J. Microbiol. Biotechnol. 12: 530-533.
  8. Lee SF, Boran TL. 2003. Roles of sortase in surface expression of the major protein adhesin P1, saliva-induced aggregation and adherence, and cariogenicity of Streptococcus mutans. Infect. Immun. 71: 676-681.
    Pubmed KoreaMed CrossRef
  9. Lévesque CM, Voronejskaia E, Huang YC, Mair RW, Ellen RP, Cvitkovitch DG. 2005. Involvement of sortase anchoring of cell wall proteins in biofilm formation by Streptococcus mutans. Infect. Immun. 73: 3773-3777.
    Pubmed KoreaMed CrossRef
  10. Mazmanian SK, Liu G, Jensen ER, Lenoy E, Schneewind O. 2000. Staphylococcus aureus sortase mutants defective in the display of surface proteins and in the pathogenesis of animal infections. Proc. Natl. Acad. Sci. USA 97: 5510-5515.
    Pubmed KoreaMed CrossRef
  11. Oh KB, Oh MN, Kim JG, Shin DS, Shin J. 2006. Inhibition of sortase-mediated Staphylococcus aureus adhesion to fibronectin via fibronectin-binding protein by sortase inhibitors. Appl. Microbiol. Biotechnol. 70: 102-106.
    Pubmed CrossRef
  12. Sang S, L apsley K, J eong WS, L achance PA, Ho CT, R osen RT. 2002. Antioxidative phenolic compounds isolated from almond skins (Prunus amygdalus Batsch). J. Agric. Food Chem. 50: 2459-2463.
    Pubmed CrossRef
  13. Selwitz RH, I smail AI, Pitts NB. 2 007. D ental caries. Lancet 369: 51-59.
    CrossRef
  14. Ton-That H, Liu G, Mazmanian SK, Faull KF, Schneewind O. 1999. Purification and characterization of sortase, the transpeptidase that cleaves surface proteins of Staphylococcus aureus at the LPXTG motif. Proc. Natl. Acad. Sci. USA 96:12424-12429.
    Pubmed KoreaMed CrossRef
  15. Xu X, Xie H, Hao J, Jiang Y, Wei X. 2011. Flavonoid glycosides from the seeds of Litchi chinensis. J. Agric. Food Chem. 59: 1205-1209.
    Pubmed CrossRef
  16. Yang WY, Won TH, Ahn CH, Lee SH, Yang HC, Shin J, Oh KB. 2015. Streptococcus mutans sortase A inhibitory metabolites from the flowers of Sophora japonica. Bioorg. Med. Chem. Lett. 25: 1394-1397.
    Pubmed CrossRef