Isolation of Nitrophenols from Diesel Exhaust Particles (DEP) as Vasodilatation Compounds

Mori, Yoki; Kamata, Kazuyuki; Toda, Nobushige; Hayashi, Hideyuki; Seki, Koh‐ichi; Taneda, Shinji; Yoshino, Shigefumi; Sakushima, Akiyo; Sakata, Masakatsu; Suzuki, Akira

doi:10.1248/bpb.26.394

Cited by 62 publications

(35 citation statements)

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“…In spite of poor fractionation and a significant lack of accuracy and reproducibility associated with this method, such isolated compounds as phenanthlenes (Mori et al 2003b), dibenzothyophenes (Mori et al 2003c), alkylphenols (Taneda et al 2004c), hydroxyphthalic acids (Mori et al 2003d), and vasodilative active nitrophenols (Mori et al 2003a) suggest that the constituents of DEP can be broadly classified into the following groups: (i) aromatic carboxylic acids, (ii) phenol derivatives, (iii) non-combustible neutral compounds. They are thus amenable to separation by using a conventional acid-base extraction procedure.…”

Section: Discussionmentioning

confidence: 99%

“…The changes in tension were amplified (FD pickup TB-612T transducer and Multichannel amplifier MEG-6108, Nihon Kohden, Tokyo, Japan) and recorded (Phoenix, DKK-TOA Co., Tokyo, Japan) (cf. Mori et al 2003a). …”

Section: Measurement Of Vascularmentioning

confidence: 99%

“…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.…”

Section: Introductionmentioning

confidence: 99%

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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: Measurement Of Vascularmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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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“…4-nitrophenol, 2-methyl-4-nitrophenol, 4-nitro-3-phenylphenol and 3-methyl-4-nitrophenol (PMNC) have been detected in DEP (Mori et al 2003). PNMC has been shown to have estrogenic activity in vitro and in vivo (Furuta et al 2004(Furuta et al , 2005, induce reproductive toxicity in male rats (Li et al 2006(Li et al , 2007Yue et al 2011) and cause immunotoxicity.…”

Section: Introductionmentioning

confidence: 99%

In vitroeffect of 4-pentylphenol and 3-methyl-4-nitrophenol on murine splenic lymphocyte populations and cytokine/granzyme production

Yang

Wan

et al. 2016

Journal of Immunotoxicology

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View Crossmark data Citing articles: 3 View citing articles JOURNAL OF IMMUNOTOXICOLOGY, 2016 VOL. 13, NO. 4, 548-556 http://dx.doi.org/10.3109/1547691X.2016 RESEARCH ARTICLEIn vitro effect of 4-pentylphenol and 3-methyl-4-nitrophenol on murine splenic lymphocyte populations and cytokine/granzyme production Gasoline exhaust particles (GEP) and diesel exhaust particles (DEP) are considered to be some of the most important air pollutants. Among the many constituents in these pollutant particles, 4-pentylphenol (PP) and 3-methyl-4-nitrophenol (PNMC) are considered important phenolics in GEP and DEP, respectively. The aim of this study was to investigate the effect of in vitro exposure to commercially-supplied PP and PNMC on populations of, and production of interleukin (IL)-2, IL-4 and granzyme-B by, mouse splenic lymphocytes. After in vitro exposure to PP or PNMC for 48 h, splenocyte viability was measured, cell phenotypes, e.g. B-cell (CD19), T-cells (CD3), T-cell subsets (CD4 and CD8), were quantified by flow cytometry and production of IL-2, IL-4 and granzyme-B was assessed via ELISA. The oxidative toxicity of PP and PNMC toward the splenocytes was also evaluated using measures of hydroxyl radical and malondiadehyde production and changes in glutathione peroxidase and superoxide dismutase activities. Results showed that in vitro exposure to PP and PNMC inhibited splenic cell parameters in a dose-related manner. Exposure to PP and PNMC decreased splenic T-lymphocyte populations and splenocyte production of cytokines and granzyme B, as well as induced oxidative stress in the splenocytes. The results also showed that the percentages of CD3 + T-cells overall and of CD4 + and CD8 + T-cells therein, among exposed splenocytes, were reduced; neither compound appeared to affect levels of CD19 + B-cells. Overall, the suppressive effects of PP were stronger than PNMC. The data here provide support for the proposal that PP-/PNMC-induced toxicity in splenocytes may be due at least in part to oxidative damage and that PP and PNMC -as components of GEP and DEP -might significantly impact on splenic T-cell formation/release of cytokines/granzymes in situ.ARTICLE HISTORY

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“…In spite of these studies, the main compounds associated with these conditions have yet to be elucidated with respect to their specific affects. In this study, four nitrophenol derivatives including 4-nitropheol (PNP) were isolated from DEP to solve this problem (Mori et al, 2003).…”

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Supplementation With Quercetin Attenuates 4‐Nitrophenol‐Induced Testicular Toxicity in Adult Male Mice

Wang

et al. 2013

The Anatomical Record

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The beneficial effects of quercetin on reproductive damage elicited by 4-nitrophenol (PNP) were studied in adult male mice. A six-week treatment of weekly intraperitoneal injections of PNP (50 mg/kg) resulted in severe damage to the seminiferous tubules, a remarkable increase in both hydroxyl radical and malondiadehyde production, and notably decreased glutathione peroxidase and superoxide dismutase activities. Moreover, PNP treatment induced germ cell apoptosis, inhibited Bcl-xl expression, and then activated Bax expression and the caspase-3 enzyme. Exposure to PNP also increased XBP-1 and HO-1 mRNAs levels. However, simultaneous supplementation with quercetin (75 mg/kg) attenuated the toxicity induced by PNP through renewal of the antioxidant enzyme's status, alleviating apoptosis by regulating the expressions of Bax and Bcl-xl, XBP-1 and HO-1mRNAs, and the regulation of caspase-3 activity. Taken together, these findings indicated that the antioxidant quercetin displays a potential preventive effect on PNP-induced oxidative damage in mouse testes and may represent an efficient supplement to attenuate reproductive toxicity from environmental toxicants in order to ensure reproductive health and sperm production.

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Isolation of Nitrophenols from Diesel Exhaust Particles (DEP) as Vasodilatation Compounds

Cited by 62 publications

References 20 publications

Isolation and identification of new vasodilative substances in diesel exhaust particles

Isolation and identification of new vasodilative substances in diesel exhaust particles

In vitroeffect of 4-pentylphenol and 3-methyl-4-nitrophenol on murine splenic lymphocyte populations and cytokine/granzyme production

Supplementation With Quercetin Attenuates 4‐Nitrophenol‐Induced Testicular Toxicity in Adult Male Mice

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