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References

  1. 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
  2. Jonsson IM, Mazmanian SK, Schneewind O, Bremell T, Tarkowski A. 2003. The role of Staphylococcus aureus sortase A and sortase B in murine arthritis. Microbes Infect. 5: 775-780.
    CrossRef
  3. Clancy KW, Melvin JA, McCafferty DG. 2010. Sortase transpeptidases: insights into mechanism, substrate specificity, and inhibition. Biopolymers 94: 385-396.
    Pubmed PMC CrossRef
  4. Selwitz RH, Ismail AI, Pitts NB. 2007. Dental caries. Lancet 369: 51-59.
    CrossRef
  5. Lee SF, Boran TL. 2003. Roles of sortase in surface expression of the major protein adhesion P1, saliva-induced aggregation and adherence, and cariogenicity of Streptococcus mutans. Infect. Immun. 71: 676-681.
    Pubmed PMC CrossRef
  6. 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
  7. Cho H, Chung B, Kim CK, Oh DC, Oh KB, Shin J. 2017. Spatholobus suberectus Dunn. constituents inhibit sortase A and Staphylococcus aureus cell clumping to fibrinogen. Arch. Pharm. Res. DOI: 10.1007/s12272-016-0884-8.
    Pubmed CrossRef
  8. Yoon JS, Sung SH, Park JH. 2004. Flavonoids from Spatholobus suberectus. Arch. Pharm. Res. 27: 589-592.
    Pubmed CrossRef
  9. Abreu Matos FJ, Gottlieb OR, Souza Andrade CH. 1975. Flavonoids from Dalbergia ecastophyllum. Phytochemistry 14:825-826.
    CrossRef
  10. Braga de Oliveira A, Fonseca e S ilva LG, Gottlieb OR. 1972. Flavonoids and coumarins from Platymiscium praecox. Phytochemistry 11: 3515-3519.
    CrossRef
  11. Bradbury RB, White DE. 1951. The chemistry of subterranean clover. Part I. Isolation of formononetin and genistein. J. Chem. Soc. 1951: 3447-3449.
    CrossRef
  12. Bevan CWL, Ekong DEU, Obasi ME, Powell JW. 1966. West African timbers. Part XIII. Extracts from the heartwood of Amphimas pterocarpoides and Pterocarpus erinacesus. J. Chem. Soc. C 1966: 509-510.
    CrossRef
  13. King FE, Grundon MF, Neill KG. 1952. The chemistry of extractives from hardwoods. Part IX. Constituents of the heartwood of Ferreirea spectabilis. J. Chem. Soc. 1952: 4580-4584.
    CrossRef
  14. Keen NT, Zaki AI, Sims JJ. 1972. Biosynthesis of hydroxyphaseollin and related isoflavanoids in diseaseresistant soybean hypocotyls. Phytochemistry 11: 1031-1039.
    CrossRef
  15. Lee KY, Shin DS, Yoon JM, Kang H, Oh KB. 2002. Expression of a transpeptidase for cell wall sorting reaction, from sortase, Staphylococcus aureus ATCC 6538p in Escherichia coli. J. Microbiol. Biotechnol. 12: 530-533.
  16. 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
  17. 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
  18. Kim SH, Shin DS, Oh MN, Chung SC, Lee JS, Oh KB. 2004. Inhibition of the bacterial surface protein anchoring transpeptidase sortase by isoquinoline alkaloids. Biosci. Biotechnol. Biochem. 68: 421-424.
    Pubmed CrossRef
  19. 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
  20. Frankel BA, Bentley M, Kruger RG, McCafferty DG. 2004. Vinyl sulfones: inhibitors of SrtA, a transpeptidase required for cell wall protein anchoring and virulence in Staphylococcus aureus. J. Am. Chem. Soc. 126: 3404–3405.
    Pubmed CrossRef

Article

Note

J. Microbiol. Biotechnol. 2017; 27(8): 1457-1460

Published online August 28, 2017 https://doi.org/10.4014/jmb.1704.04001

Copyright © The Korean Society for Microbiology and Biotechnology.

Inhibitory Effects of Flavonoids from Spatholobus suberectus on Sortase A and Sortase A-Mediated Aggregation of Streptococcus mutans

Wanki Park 1, Chan-Hong Ahn 1, Hyunjoo Cho 2, Chang-Kwon Kim 2, Jongheon Shin 2 and Ki-Bong Oh 1*

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

Received: April 3, 2017; Accepted: June 13, 2017

Abstract

Seven flavonoids were isolated from Spatholobus suberectus via repetitive column
chromatography and high-performance liquid chromatography. The chemical structures of
these compounds were identified by spectroscopic analysis and comparison with values
reported in the literature. Among the flavonoids tested, 7-hydroxy-6-methoxyflavanone (1)
and formononetin (4) exhibited strong inhibitory activity against Streptococcus mutans SrtA,
with IC50 values of 46.1 and 41.8 μM, respectively, but did not affect cell viability. The onset
and magnitude of inhibition of saliva-induced aggregation in S. mutans treated with
compounds 1 and 4 were comparable to the behavior of a srtA-deletion mutant without
treatment.

Keywords: Spatholobus suberectus, flavonoids, Streptococcus mutans, sortase A, cell aggregation

References

  1. 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
  2. Jonsson IM, Mazmanian SK, Schneewind O, Bremell T, Tarkowski A. 2003. The role of Staphylococcus aureus sortase A and sortase B in murine arthritis. Microbes Infect. 5: 775-780.
    CrossRef
  3. Clancy KW, Melvin JA, McCafferty DG. 2010. Sortase transpeptidases: insights into mechanism, substrate specificity, and inhibition. Biopolymers 94: 385-396.
    Pubmed KoreaMed CrossRef
  4. Selwitz RH, Ismail AI, Pitts NB. 2007. Dental caries. Lancet 369: 51-59.
    CrossRef
  5. Lee SF, Boran TL. 2003. Roles of sortase in surface expression of the major protein adhesion P1, saliva-induced aggregation and adherence, and cariogenicity of Streptococcus mutans. Infect. Immun. 71: 676-681.
    Pubmed KoreaMed CrossRef
  6. 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
  7. Cho H, Chung B, Kim CK, Oh DC, Oh KB, Shin J. 2017. Spatholobus suberectus Dunn. constituents inhibit sortase A and Staphylococcus aureus cell clumping to fibrinogen. Arch. Pharm. Res. DOI: 10.1007/s12272-016-0884-8.
    Pubmed CrossRef
  8. Yoon JS, Sung SH, Park JH. 2004. Flavonoids from Spatholobus suberectus. Arch. Pharm. Res. 27: 589-592.
    Pubmed CrossRef
  9. Abreu Matos FJ, Gottlieb OR, Souza Andrade CH. 1975. Flavonoids from Dalbergia ecastophyllum. Phytochemistry 14:825-826.
    CrossRef
  10. Braga de Oliveira A, Fonseca e S ilva LG, Gottlieb OR. 1972. Flavonoids and coumarins from Platymiscium praecox. Phytochemistry 11: 3515-3519.
    CrossRef
  11. Bradbury RB, White DE. 1951. The chemistry of subterranean clover. Part I. Isolation of formononetin and genistein. J. Chem. Soc. 1951: 3447-3449.
    CrossRef
  12. Bevan CWL, Ekong DEU, Obasi ME, Powell JW. 1966. West African timbers. Part XIII. Extracts from the heartwood of Amphimas pterocarpoides and Pterocarpus erinacesus. J. Chem. Soc. C 1966: 509-510.
    CrossRef
  13. King FE, Grundon MF, Neill KG. 1952. The chemistry of extractives from hardwoods. Part IX. Constituents of the heartwood of Ferreirea spectabilis. J. Chem. Soc. 1952: 4580-4584.
    CrossRef
  14. Keen NT, Zaki AI, Sims JJ. 1972. Biosynthesis of hydroxyphaseollin and related isoflavanoids in diseaseresistant soybean hypocotyls. Phytochemistry 11: 1031-1039.
    CrossRef
  15. Lee KY, Shin DS, Yoon JM, Kang H, Oh KB. 2002. Expression of a transpeptidase for cell wall sorting reaction, from sortase, Staphylococcus aureus ATCC 6538p in Escherichia coli. J. Microbiol. Biotechnol. 12: 530-533.
  16. 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
  17. 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
  18. Kim SH, Shin DS, Oh MN, Chung SC, Lee JS, Oh KB. 2004. Inhibition of the bacterial surface protein anchoring transpeptidase sortase by isoquinoline alkaloids. Biosci. Biotechnol. Biochem. 68: 421-424.
    Pubmed CrossRef
  19. 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
  20. Frankel BA, Bentley M, Kruger RG, McCafferty DG. 2004. Vinyl sulfones: inhibitors of SrtA, a transpeptidase required for cell wall protein anchoring and virulence in Staphylococcus aureus. J. Am. Chem. Soc. 126: 3404–3405.
    Pubmed CrossRef