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Structural analysis of oxidation products of urofuran acid by hypochlorous acid

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Lipids

Abstract

The oxidation of urofuran acid derivatives (1–2) by hypochlorous acid (HOCl) was investigated with the goal to possibly simplify the detection of their metabolites in biological materials. The oxidation products of 3-carboxy-4-methyl-5-propyl-2-furanpropionic acid (1) were obtained as an isomeric mixture and confirmed to exist ascis (3a) andtrans (3b) isomers, based on their13C nuclear magnetic resonance (NMR) spectra. Similarly, the products of 5-H substituted acid 2 obtained by oxidation with HOCl were identified as 4a and 4b by13C and1H NMR which indicated the presence ofcis andtrans hemiacetal hydrogens at C-5 in a ratio of 2.11∶1. The oxidation was found to proceed in a manner different from that of the F-acid, because of the presence of the electron withdrawing COOCH3 group at C-3 which favored the nucleophilic attack on the carbonyl group to affordcis- andtrans-2,5-dihydroxy-2,5-dihydrofurans (3a−b, 4a−b).

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Abbreviations

CI-MS:

chemical ionization mass spectrometry

CMPF:

3-carboxy-4-methyl-5-propyl-2-furanpropionic acid (1)

COSY:

correlation spectroscopy

DEPT:

distortionless enhancement by polarization transfer

EI-MS:

electron impact ionization mass spectrometry

FAB-MS:

fast atom bombardment mass spectrometry

GC/MS:

gas chromatography/mass spectrometry

HPLC:

highnuclear magnetic resonance

TLC:

thin-layer chromatography

TMS:

tetramethylsilane

References

  1. Spiteller, M., and Spiteller, G. (1979)J. Chromatogr. 164, 253–317.

    PubMed  CAS  Google Scholar 

  2. Liebich, H.M., Pickert, A., and Tetschner, B. (1984)J. Chromatogr. 289, 259–266.

    Article  PubMed  CAS  Google Scholar 

  3. Collier, R., Lindup, W.E., Liebich, H.M., and Spiteller, G. (1986)British J. Clin. Pharmacol. 21, 610–611.

    Google Scholar 

  4. Mabuchi, H., and Nakahashi, H. (1986)Nephron, 44, 277–281.

    Article  PubMed  CAS  Google Scholar 

  5. Hannemann, K., Puchta, V., Simon, E., Ziegler, H., Ziegler, G., and Spiteller, G. (1989)Lipids 24, 296–298.

    Article  PubMed  CAS  Google Scholar 

  6. Sand, D.M., Schlenk, H., Thoma, H., and Spiteller, G. (1983)Biochim. Biophys. Acta 751, 455–461.

    PubMed  CAS  Google Scholar 

  7. Ushijima, Y., and Nakano, M. (1980)Biochem. Biophys. Res. Commun. 93, 1232–1237.

    Article  PubMed  CAS  Google Scholar 

  8. Schödel, R., and Spiteller, G. (1985)Helv. Chim. Acta 68, 1624–1634.

    Article  Google Scholar 

  9. Ishii, K., Okajima, H., Koyamatsu, T., Okada, Y., and Watanabe, H. (1988)Lipids 23, 694–700.

    Article  CAS  Google Scholar 

  10. Jandke, J., Schmidt, J., and Spiteller, G. (1988)Liebigs Ann. Chem. 29–34.

  11. Schödel, R., and Spiteller, G. (1987)Liebigs Ann. Chem. 459–462.

  12. Spiteller, M., Spiteller, G., and Hoyer, G.A., (1980)Chem. Ber. 113, 699–709.

    CAS  Google Scholar 

  13. Pfordt, J., Thoma, H., and Spiteller, G. (1981)Liebigs Ann. Chem. 2298–2308.

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Authors and Affiliations

  1. The Bio-Dynamics Research Institute, Nagoya Memorial Hospital, 4-305, Hirabari, Tenpaku-ku, 468, Nagoya

    Toyokazu Ohki & Naoki Yamanaka

  2. Nagoya University Branch Hospital, 1-20, Daiko-minami 1-chome, Higashi-ku, 461, Nagoya

    Kenji Maeda

  3. Faculty of Pharmaceutical Sciences, Nagoya City University, 3-1, Tanabe-dori, Mizuho-ku, 467, Nagoya

    Jinsaku Sakakibara

  4. Faculty of Pharmacy, Meijo University, Yagoto, Tempaku-ku, 468, Nagoya, Japan

    Eiji Suzuki

Authors
  1. Toyokazu Ohki
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  2. Kenji Maeda
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  3. Jinsaku Sakakibara
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  4. Eiji Suzuki
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  5. Naoki Yamanaka
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Ohki, T., Maeda, K., Sakakibara, J. et al. Structural analysis of oxidation products of urofuran acid by hypochlorous acid. Lipids 28, 35–41 (1993). https://doi.org/10.1007/BF02536357

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  • DOI: https://doi.org/10.1007/BF02536357

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