Improvement of an efficient separation method for chemicals in diesel exhaust particles: analysis for nitrophenols

Noya, Yoichi; Mikami, Yusuke; Taneda, Shinji; Mori, Yoki; Suzuki, Akira; Ohkura, Kazuhiro; Yamaki, Kouya; Yoshino, Shigefumi; Seki, Koh‐ichi

doi:10.1007/s11356-008-0006-3

Cited by 32 publications

(16 citation statements)

References 33 publications

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“…They are thus amenable to separation by using a conventional acid-base extraction procedure. Based on this concept, we have developed the new fractionation scheme used for this work (Noya et al 2008). The sodium bicarbonate extract obtained by this procedure has been shown to contain various aromatic carboxylic acids including the new vasodilatory nitro-compounds, 4-hydroxy-3-nitrobenzoic acid (8) and 3-hyroxy-4-nitrobenzoic acid (9).…”

Section: Discussionmentioning

confidence: 99%

“…Therefore, it was crucial to develop a more efficient and reliable method for the isolation of biologically significant components in DEP. Recently we reported an alternative protocol entailing successive extraction with water, sodium bicarbonate, and sodium hydroxide (Noya et al 2008). Analysis of the sodium hydroxide extract revealed that vasodilatory active nitrophenols are present in DEP in significantly higher amounts than estimated by a previous method involving successive solvent polarity-based extractions, followed by repeated column chromatography.…”

Section: Introductionmentioning

confidence: 97%

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Isolation and identification of new vasodilative substances in diesel exhaust particles

Seki

Noya

Mikami

et al. 2009

Environ Sci Pollut Res

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Goal, Scope, and Background We recently developed a new isolation method for diesel exhaust particles (DEP), involving successive extraction with H 2 O, 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 concentration 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 to 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 telephthalic 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. DiscussionThe sodium bicarbonate extract was rich in the acidic 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. Seidel et al. 2006). A number of studies on the adverse effects of diesel exhaust particles (DEP) on human health, including lung cancer (McClellan 1987;Ichinose et al. 1997), allergic rhinitis (Muranaka 1986;Takafuji et al. 1987), bronchial asthma-like disease (Sagai et al. 1996;Miyabara et al. 1998), and disruption of endocrine function, have been reported (Yoshida et al. 1999;Watanabe & Oonuki 1999;Tsukue et al. 2001Tsukue et al. , 2002. While these studies have furnished epidemiologically important results, they have been done without knowledge of the bioactive entities in DEP, making it difficult to estimate the effect of individual components on human health. In our earlier studies on the isolation and identification of bioactive compounds contained in DEP, we have isolated aromatic substances including nitrophenols (Mori et al. 2003a;Taneda et al. 2004a) that showed strong vasodilatory activity by a method involving successive solvent extractions, followed by repeated column chromatography. This multi-step isolation procedure, however, resulted in poor fractionation with impaired accuracy and reproducibility. Therefore, it was crucial to develop a more efficient and ...

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 97%

Isolation and identification of new vasodilative substances in diesel exhaust particles

Seki

Noya

Mikami

et al. 2009

Environ Sci Pollut Res

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“…One kg of diesel exhaust particles contains an average of 52 mg PNMPP. 22) Diesel exhaust particles are stable in the environment and are considered to be one of the main airborne pollutants in urban areas, but the mechanism of PNMPP-induced toxicity is unclear.…”

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confidence: 99%

Quercetin Attenuates Oxidative Damage Induced by Treatment of Embryonic Chicken Spermatogonial Cells with 4-Nitro-3-phenylphenol in Diesel Exhaust Particles

Mi¹,

Zhang²,

Li³

et al. 2010

Bioscience, Biotechnology, and Biochemistry

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“…Nevertheless, it is considered to be hazardous waste and a priority toxic pollutant by the the U.S. Environmental Protection Agency (EPA). Recently, it has been found that 1 kg of DEP contains an average of 169 mg PNP [19]. PNP can damage the central nervous system, liver, kidney and blood of humans and animals [20].…”

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confidence: 99%

Protective Effect of Quercetin on the Reproductive Toxicity of 4-nitrophenol in Diesel Exhaust Particles on Male Embryonic Chickens

Zhang

et al. 2010

J. Reprod. Dev.

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Abstract. The 4-nitrophenol (PNP) in diesel exhaust particles (DEP) has been identified as a vasodilator and is a known degradation product of the insecticide parathion. In this study, the protective effect of quercetin, a potent oxygen free radical scavenger and metal chelator, against the oxidative damage of PNP on cultured testicular cells was studied in male embryonic chickens. Testicular cells from Day 18 embryos were cultured in serum-free McCoy's 5A medium and challenged with quercetin (1.0 μg/ml) alone or in combinations with PNP (10 -7 -10 -5 M) for 48 h. The oxidative damage was estimated by measuring cell viability, content of malondialdehyde (MDA), activity of superoxide dismutase (SOD) and glutathione peroxidation (GSH-Px) activity. The results showed that exposure to PNP (10 -5 M) induced condensed nuclei, vacuolated cytoplasm and a decrease in testicular cell viability and spermatogonial cell number. Exposure to PNP induced lipid peroxidation by elevation of the content of MDA. Exposure to PNP also decreased GSH-Px activity and SOD activity. However, simultaneous supplementation with quercetin restored these parameters to the same levels as the control. Consequently, PNP induced oxidative stress in spermatogonial cells, and dietary quercetin may attenuate the reproductive toxicity of PNP to restore the intracellular antioxidant system in the testicular cells of embryonic chickens. Key words: Chicken, 4-Nitrophenol, Oxidative damage, Quercetin, Spermatogonial cells (J. Reprod. Dev. 56: 195-199, 2010) ir pollution is now one of the serious concerns about the environment and health. Recently, the use of diesel enginepowered cars has been increasing in the world because they offer better fuel efficiency than gasoline engines. However, diesel engines emit more nitrogen oxides and particles than gasoline engines; the latter is considered to be the major source of air pollution [1].Vast amounts of diesel exhaust particles (DEP) pollute the atmosphere as a consequence of the use of diesel engines. For example, Japan, the United States, England and the European Union emit 58902, 111530, 37000 and 240000 tons of DEP into the atmosphere per year, respectively [2][3][4][5][6]. Exposure to DEP has many hazardous effects on human and animal health, e.g., carcinogenic action, such as a lung cancer [7], bronchial asthma [8] and disruption of female and male reproductive functions, such as suppressing spermatogenesis and increasing the abortion rate and uterine weight [9][10][11][12][13][14][15][16]. However, the specific compounds responsible for this toxicity remain still largely unknown.In order to address this problem, four nitrophenol derivatives, 4-nitrophenol (PNP), 2-methyl-4-nitrophenol, 3-methyl-4-nitrophenol and 4-nitro-3-phenylphenol, were isolated from DEP [17]. PNP is not only a type of chemical found in DEP but is also a degradation product of the insecticide parathion, which is used as a drug or xenobiotic, a dye and a fungicide for leather [18]. Nevertheless, it is considered to be hazardous wa...

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Improvement of an efficient separation method for chemicals in diesel exhaust particles: analysis for nitrophenols

Abstract: The present method involving an acid-base extraction, in situ derivatization, and GC-MS analysis has shown to be a simple, efficient, and reliable method for the isolation and identification of the chemical substances in DEP.

Cited by 32 publications

References 33 publications

Isolation and identification of new vasodilative substances in diesel exhaust particles

Isolation and identification of new vasodilative substances in diesel exhaust particles

Quercetin Attenuates Oxidative Damage Induced by Treatment of Embryonic Chicken Spermatogonial Cells with 4-Nitro-3-phenylphenol in Diesel Exhaust Particles

Protective Effect of Quercetin on the Reproductive Toxicity of 4-nitrophenol in Diesel Exhaust Particles on Male Embryonic Chickens

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