Advertisement

Environmental Science and Pollution Research

, Volume 17, Issue 3, pp 717–723 | Cite as

Isolation and identification of new vasodilative substances in diesel exhaust particles

  • Koh-ichi SekiEmail author
  • Yoichi Noya
  • Yusuke Mikami
  • Shinji Taneda
  • Akira K. Suzuki
  • Yuji Kuge
  • Kazue Ohkura
AREA 6.3 • METHODS, MODELING, MONITORING OF CHEMICALS • RESEARCH ARTICLE

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.

Keywords

Acidic components Diesel exhaust particles Fractionation 3-Hydroxy-4-nitrobenzoic acid 4-Hydroxy-3-nitrobenzoic acid Separation method Vasodilatory compounds 

Notes

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.

References

  1. Airborne Particles Expert Group (1999) Source apportionment of airborne particulate matter in the United Kingdom. United Kingdom Department of Environment, Transport and Regions, The Welsh Office, the Scottish Office and the Department of Environment (Northern Ireland) 9–37Google Scholar
  2. Bayona JM, Markides KE, Lee M (1988) Characterization of polar polycyclic aromatic compounds in a heavy-duty diesel exhaust particulate by capillary column gas chromatography and high-resolution mass spectrometry. Environ Sci Technol 22:1440–1447CrossRefGoogle Scholar
  3. Draper WM (1986) Quantitation of nitro- and dinitropolycyclic aromatic hydrocarbons in diesel exhaust particulate matter. Chemosphere 15:437–447CrossRefGoogle Scholar
  4. Erdinger L, Durr M, Hopker KA (2005) Correlations between mutagenic activity of organic extracts of airborne particulate matter, NOx, and sulphur dioxide in southern Germany—results of a two-year study. Environ Sci Pollut Res 12:10–20CrossRefGoogle Scholar
  5. Heeb NV, Schmid P, Kohler M, Gujer E, Zennegg M, Wenger D, Wichser A, Ulrich A, Gfeller U, Honegger P, Zeyer K, Emmenegger L, Petermann J-L, Czerwinski J, Mosimann T, Kasper M, Mayer A (2008) Secondary effects of catalytic diesel particulate filters: conversion of PAHs versus formation of nitro-PAHs. Environ Sci Technol 42:3773–3779CrossRefGoogle Scholar
  6. Ichinose T, Yajima Y, Nagashima M, Takenoshita S, Nagamachi Y, Sagai M (1997) Lung carcinogenesis and formation of 8-hydroxy-deoxyguanosine in mice by diesel exhaust particles. Carcinogenesis 18:185–192CrossRefGoogle Scholar
  7. Japan Environmental Agency (1998) The research on the total amount of emission and automobile exhaust source unit-the NOX according to object automobile in the usual transit. pp 200–203Google Scholar
  8. McClellan RO (1987) Health effects of exposure to diesel exhaust particles. Annu Rev Pharmacol Toxicol 27:279–300CrossRefGoogle Scholar
  9. Mestres R (2005) Green chemistry—views and strategies. Environ Sci Pollut Res 12:128–132CrossRefGoogle Scholar
  10. Miyabara Y, Ichinose T, Takano H, Lim HB, Sagai M (1998) Effects of diesel exhaust on allergic airway inflammation in mice. J Allergy Clin Immunol 102:805–812CrossRefGoogle Scholar
  11. Mori Y, Kamata K, Toda N, Hayashi H, Seki K, Taneda S, Yoshino S, Sakushima A, Sakata M, Suzuki AK (2003a) Isolation of nitrophenols from diesel exhaust particles (DEP) as vasodilatation compounds. Biol Pharm Bull 26:394–395CrossRefGoogle Scholar
  12. Mori Y, Taneda S, Kamata K, Sakushima A, Hayashi H, Suzuki AK, Sakata M, Yoshino S, Sagai M, Seki K (2003c) Identification of phenanthrene and related compounds in diesel exhaust particles by gas chromatography-mass spectrometry. Environ Sci 10:187–192Google Scholar
  13. Mori Y, Taneda S, Kamata K, Sakushima A, Hayashi H, Suzuki AK, Sakata M, Yoshino S, Sagai M, Seki K (2003d) Identification of alkyldibenzothiophenes in diesel exhaust particles by gas chromatography-mass spectrometry. Environ Sci 10:157–164Google Scholar
  14. Mori Y, Taneda S, Sakushima A, Hayashi H, Kamata K, Suzuki AK, Sakata M, Yoshino S, Sagai M, Seki K (2003b) Isolation and characterization of hydroxyphthalate derivatives in diesel exhaust particles. Environ Sci 10:51–54Google Scholar
  15. Morville S, Scheyer A, Mirabel P, Millet M (2006) Spatial and geographical variations of urban, suburban and rural atmospheric concentrations of phenols and nitrophenols. Environ Sci Pollut Res 13:83–89CrossRefGoogle Scholar
  16. Muranaka M, Suzuki S, Koizumi K, Takafuji S, Miyamoto T, Ikemori R, Tokiwa H (1986) Adjuvant activity of diesel-exhaust particulates for the production of IgE antibody in mice. J Allergy Clin Immunol 77:616–623CrossRefGoogle Scholar
  17. Noya Y, Mikami Y, Taneda S, Mori Y, Suzuki A, Ohkura K, Yamaki K, Yoshino S, Seki K-I (2008) Improvement of a facile and efficient separation method for chemicals in diesel exhaust particles: analysis of the contents of nitrophenols. Environ Sci Pollut Res 15:318–321CrossRefGoogle Scholar
  18. Ona LF, Melinda A, Alberto P, Prudente JA, Sigua GC (2006) Levels of lead in urban soils from selected cities in a central region of the Philippines. Environ Sci Pollut Res 13:177–183CrossRefGoogle Scholar
  19. Petroleum Energy Center Japan (1999) Workshop report with the European experts. PEC-1998TA37:112–115Google Scholar
  20. Sagai M, Furuyama A, Ichinose T (1996) Biological effects of diesel exhaust particles (DEP). III. Pathogenesis of asthma like symptoms in mice. Free Radical Biol Med 21:199–209CrossRefGoogle Scholar
  21. Schuetzle D (1983) Sampling of vehicle emissions for chemical analysis and biological testing. Environ Health Persp 47:65–80CrossRefGoogle Scholar
  22. Schuetzle D, Lewtas J (1986) Bioassay-directed chemical analysis in environmental research. Anal Chem 58:1060A–1075ACrossRefGoogle Scholar
  23. Seidel B, Alm M, Peters R, Kordell W, Schaffer A (2006) Safety evaluation for a biodiesel process using prion-contaminated animal fat as a source. Environ Sci Pollut Res 13:125–130CrossRefGoogle Scholar
  24. Takafuji S, Suzuki S, Koizumi K, Tadokoro K, Miyamoto T, Ikemori R, Muranaka M (1987) Diesel-exhaust particulates inoculated by the intranasal route have an adjuvant activity for IgE production in mice. J Allergy Clin Immunol 79:639–645CrossRefGoogle Scholar
  25. Taneda S, Kamata K, Hayashi H, Toda N, Seki K, Sakushima A, Yoshino S, Yamaki K, Sakata M, Mori Y, Suzuki AK (2004a) Investigation of vasodilatory substances in diesel exhaust particles (DEP) Isolation and identification of nitrophenol derivatives. J Health Sci 50:133–141CrossRefGoogle Scholar
  26. Taneda S, Mori Y, Akiy S, Kamata K, Hayashi H, Seki K, Sakata M, Yoshino S, Yamaki K, Sagai M, Suzuki AK (2004b) Separation and characterization of alkyltrimethylbenzene derivatives in diesel exhaust particles (DEP). Environ Sci 11:171–178Google Scholar
  27. Tsukue N, Toda N, Sagai M, Watanabe G, Taya K, Tsubone H, Suzuki AK (2002) Diesel exhaust particulate extract (DEPE)-induced abnormal parturition associated with increased myometrial contractility in C57BL mice. Environ Sci 9:355–367Google Scholar
  28. Tsukue N, Toda N, Tsubone H, Sagai M, Jin WZ, Watanabe G, Taya K, Birumachi J, Suzuki AK (2001) Diesel exhaust (DE) affects the regulation of testicular function in male Fischer 344 rats. J Toxicol Environ Health A 63:115–126CrossRefGoogle Scholar
  29. United States Environmental Protection Agency (1999) Analysis of the impacts of control program on motor vehicle toxics emissions and exposure in urban areas and nationwide EPA420-R-99-029:120Google Scholar
  30. Watanabe N, Oonuki Y (1999) Inhalation of diesel engine exhaust affects spermatogenesis in growing male rats. Environ Health Persp 107:539–544CrossRefGoogle Scholar
  31. Yoshida S, Sagai M, Oshio S, Umeda T, Ihara T, Sugamata M, Sugawara I, Takeda K (1999) Exposure to diesel exhaust affects the male reproductive system of mice. Int J Androl 22:307–315CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2009

Authors and Affiliations

  • Koh-ichi Seki
    • 1
    Email author
  • Yoichi Noya
    • 1
  • Yusuke Mikami
    • 2
  • Shinji Taneda
    • 3
  • Akira K. Suzuki
    • 3
  • Yuji Kuge
    • 1
  • Kazue Ohkura
    • 2
  1. 1.Central Institute of Isotope ScienceGraduate School of Medicine, Hokkaido UniversitySapporoJapan
  2. 2.Department of Radiopharmaceutical Chemistry, Faculty of Pharmaceutical SciencesHealth Sciences University of HokkaidoIshikari-TobetsuJapan
  3. 3.Environmental Nanotoxicology Section, Research Center for Environmental RiskNational Institute for Environmental StudiesTsukubaJapan

Personalised recommendations