Structures of two polyamine-containing catecholate siderophores from vibrio fluvialis

Shigeo Yamamoto, Noriyuki Okujo, Yasuhiro Fujita, Miki Saito, Takashi Yoshida, Sumio Shinoda

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Abstract

From low-iron cultures of Vibrio fluvialis AQ 0012, two new compounds with siderophore activity were purified by XAD-7 adsorption followed by preparative TLC. Norspermidine and 2,3-dihydroxybenzoic acid were identified as constituents common to both compounds by GC-MS analyses of their acid hydrolytic products. In addition, L-threonine was identified in the hydrolysate of one compound, named fluvibactin. Based on high magnetic NMR analyses, the structure of fluvibactin was established as iV4-[2-(2,3-dihydroxyphenyl)- ftra/is-5-methyl-2-oxa2oline-4-yl]carboxy-iV1, iV7-6is-(2,3-dihydroxybenzoyl)- norspermidine, and that of the other compound as iV, iV7-w-(2,3-dihydroxybenzoyl)- norspermidine. The structures were supported by fast atom bombardment mass spectrometry. Both of the purified compounds restored growth inhibition of the producer strain and V. cholerae Non-01 induced by ethylenediamine di-(o-hydroxyphenylacetic acid), a potent synthetic chelating agent of ferric iron. 1993

Original languageEnglish
Pages (from-to)538-544
Number of pages7
JournalJournal of Biochemistry
Volume113
Issue number5
Publication statusPublished - May 1993

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ASJC Scopus subject areas

  • Statistics, Probability and Uncertainty
  • Applied Mathematics
  • Physiology (medical)
  • Radiology Nuclear Medicine and imaging
  • Molecular Biology
  • Biochemistry

Cite this

Yamamoto, S., Okujo, N., Fujita, Y., Saito, M., Yoshida, T., & Shinoda, S. (1993). Structures of two polyamine-containing catecholate siderophores from vibrio fluvialis. Journal of Biochemistry, 113(5), 538-544.