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Isolation and identification of new vasodilative substances in diesel exhaust particles

  • AREA 6.3 • METHODS, MODELING, MONITORING OF CHEMICALS • RESEARCH ARTICLE
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Abstract

Background, aim, and scope

We recently developed a new isolation method for diesel exhaust particles (DEP), involving successive extraction with H2O, sodium bicarbonate, and sodium hydroxide, in which the sodium hydroxide extract was found to consist of phenolic components. Analysis of the extract revealed that vasodilative-active nitrophenols are in DEP in significantly higher concentrations than those estimated by an earlier method involving a combination of solvent extraction and repeated chromatography. These findings indicated that our new procedure offers a simple, efficient, and reliable method for the isolation and identification of bioactive substances in DEP. This encouraged us to extend our work toward investigating new vasodilatory substances in the sodium bicarbonate extract.

Materials and methods

DEP were collected from the exhaust of a 4JB1-type engine (ISUZU Automobile Co., Tokyo, Japan). GC-MS analysis was performed with a GCMS-QP2010 instrument (Shimadzu, Kyoto, Japan).

Results

DEP dissolved in 1-butanol was successively extracted with water, sodium bicarbonate, and then aqueous sodium hydroxide. The sodium bicarbonate extract was neutralized and the resulting mixture of acidic components was subjected to reverse-phase (RP) column chromatography followed by RP-HPLC with fractions assayed for vasodilative activity. This led to the identification of terephthalic acid, p-hydroxybenzoic acid, isophthalic acid, phthalic acid, 3-hydroxy-4-nitrobenzoic acid, 4-hydroxy-3-nitrophenol, and 1,4,5-naphthalene tricarboxylic acid as components of DEP.

Discussion

The sodium bicarbonate extract was rich in aromatic carboxylic acid components. Repeated reverse-phase chromatography resulted in the successful isolation of several acidic substances including the new vasodilative materials, 4-hydroxy-3-nitrobenzoic acid, and 3-hydroxy-4-nitrobenzoic acid.

Conclusions

Our new fractionation method for DEP has made possible the isolation of new vasodilative compounds from the sodium bicarbonate extract.

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Acknowledgments

This study was supported in part by a grant from the Japan Society for the Promotion of Science (Basic Research C-17510052). KS gratefully acknowledges Dr. Nagara Tamaki (Hokkaido University) and Dr. Raymond Jeremy Hugh Davies (Emeritus professor, Queens University Belfast) for their constructive comments and suggestions.

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Authors and Affiliations

  1. Central Institute of Isotope Science, Graduate School of Medicine, Hokkaido University, Sapporo, 060-0815, Japan

    Koh-ichi Seki, Yoichi Noya & Yuji Kuge

  2. Department of Radiopharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, 061-0293, Japan

    Yusuke Mikami & Kazue Ohkura

  3. Environmental Nanotoxicology Section, Research Center for Environmental Risk, National Institute for Environmental Studies, Tsukuba, 305-8506, Japan

    Shinji Taneda & Akira K. Suzuki

Authors
  1. Koh-ichi Seki
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  2. Yoichi Noya
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  3. Yusuke Mikami
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  4. Shinji Taneda
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  5. Akira K. Suzuki
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  6. Yuji Kuge
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  7. Kazue Ohkura
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Correspondence to Koh-ichi Seki.

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Seki, Ki., Noya, Y., Mikami, Y. et al. Isolation and identification of new vasodilative substances in diesel exhaust particles. Environ Sci Pollut Res 17, 717–723 (2010). https://doi.org/10.1007/s11356-009-0207-4

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  • DOI: https://doi.org/10.1007/s11356-009-0207-4

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