Journal of Microbiology and Biotechnology

The Korean Society for Microbiology and Biotechnology (한국미생물·생명공학회)
권호 표지

N-Acetylglycine Side Chain is Critical for the Antimicrobial Activity of Xanthostatin

  • Kim, Si-Kwan (Department of Life Science, College of Natural Science, Konkuk University) ;
  • Ubukata, Makoto (Division of Biofunctional Chemistry, Biotechnology Research Center, Toyama Prefecture University) ;
  • Isono, Kiyoshi (The Institute of Physics ＆ Chemistry Research (RIKEN))
  • Published : 2003.12.01
Download PDF
⟨ Previous Next ⟩

Abstract

This study was carried out to elucidate the mode of bacteriostatic property of xanthostatin (XS), a novel depsipeptide antibiotic with an N-acetylglycine side chain and selective antimicrobial activity against Xanthomonas spp. Two biotransformed XSs were isolated by the treatment of XS with the cell lysate of Xanthomonas campestris pv. citri, a solvent partition, preparative TLC, and HPLC. Structure determination of those two biotransformed XSs demonstrated deletion of the N-acetylglycine side chain. Noteworthily, they showed no antimicrobial activity against Xanthomonas spp. This result suggests that the N-acetylglycine side chain plays a critical role in the antimicrobial activity of XS, and that the bacteriostatic property of XS is due to susceptibility of the ester bond between the hexadepsipeptide nucleus and the N-acetylglycine side chain to hydrolytic enzyme(s) produced by Xanthomonas spp.

Keywords

References

  1. J. Antibiot. v.19 Xanthocidin, a new antibiotic Ashhi,K.;J.Nagatsu;S.Suzuki
  2. Agric. Biol. Chem. v.51 Xanthostatin, a new antibiotic Cheng,X.C.;T.Kihara;H.Kusakabe;R.P.Fang;Z.F.Ni;Y.C.Shen;K.Ko;I.Yamaguchi;K.Isono https://doi.org/10.1271/bbb1961.51.279
  3. J. Microbiol. Biotechnol. v.12 Identification of Streptomyces sp. producing new polyene antibiotics and in vivo antimicrobial activity of tetrin C against phytopathogenic fungi Choi,W.C.;S.Y.Hwang;T.K.Park;S.K.Kim
  4. Agric. Biol. Chem. v.44 Purification of α-amino acid ester hydrolase from Xanthomonas citri Kato,K.;K.Kawahara;T.Takahashi;A.Kakinuma https://doi.org/10.1271/bbb1961.44.1069
  5. J. Microbiol. Biotechnol. v.11 Strptomyces showing antifungal activities against six plant pathogenic fungi Kim,B.J.;M.J.Cho;J.C.Kim;K.Y.Cho;G.J.Choi;C.H.Lee;Y.H.Lim
  6. Tetrahedron Lett. v.33 The structure of xanthostatin Kim,S.K.;M.Ubukata;K.Kobayashi;K.Isono https://doi.org/10.1016/S0040-4039(00)92242-1
  7. Rev. Plant Prot. Res. v.11 Present epidemic status and control of the citrus canker disease, Xanthomonas citri (Hasse) Dow, in Japan Kuhara,S.
  8. Biochem. J. v.233 Purification and characterization of ascamycin-hydrolysing aminopeptidase from Xanthomonas citri Osada,H.;K.Isono https://doi.org/10.1042/bj2330459
  9. Plant Dis. v.67 Canker, a threat to citrus in the Gulf-coast status Stall,R.E.;C.P.Seymour https://doi.org/10.1094/PD-67-581