Identification of estrogenic/anti-estrogenic compounds in diesel exhaust particulate extract.
Diesel exhaust particulate extract (DEPE) was obtained from diesel exhaust particulates with Soxhlet extraction using dichloromethane. After separating DEPE into 11 fractions by liquid-liquid extraction, the neutral fraction (N) showed anti-estrogenic activity and the weak acid (phenol) fraction (WA(P)) showed estrogenic and anti-estrogenic activities by a yeast two-hybrid assay system expressing human estrogen receptor alpha. Both fractions were thoroughly fractionated by silica gel column chromatography and reversed-phase HPLC. In the WA(P) fraction, 3-methyl-4-nitrophenol and 2,6-dimethyl-4-nitrophenol were identified by LC-MS/MS as estrogenic compounds. This is the first study to identify 2,6-dimethyl-4-nitrophenol in DEPE and the first study to show that it is an estrogenic compound. In the N fraction, 1-hydroxypyrene was also identified by LC-MS/MS as an anti-estrogenic compound.
Noguchi
Keiko
K
Graduate School of Natural Science and Technology/Faculty of Pharmaceutical Sciences, Kanazawa University, Kakuma-machi, Kanazawa, Japan.
Toriba
Akira
A
Chung
Sang Woon
SW
Kizu
Ryoichi
R
Hayakawa
Kazuichi
K
D000393:Air Pollutants / Q000032:analysis* / Q000737:chemistry; D005591:Chemical Fractionation / Q000379:methods; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D003408:Cresols / Q000378:metabolism* / Q000506:poisoning; D052244:Endocrine Disruptors / Q000737:chemistry / Q000378:metabolism; D004784:Environmental Monitoring / Q000379:methods; D004965:Estrogen Antagonists / Q000032:analysis* / Q000737:chemistry; D004967:Estrogens / Q000032:analysis* / Q000737:chemistry; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D009596:Nitrophenols / Q000378:metabolism* / Q000506:poisoning; D012822:Silicon Dioxide / Q000737:chemistry; D013048:Specimen Handling; D021241:Spectrometry, Mass, Electrospray Ionization; D053719:Tandem Mass Spectrometry; D020798:Two-Hybrid System Techniques; D001335:Vehicle Emissions / Q000032:analysis*
D000393:Air Pollutants; D003408:Cresols; D052244:Endocrine Disruptors; D004965:Estrogen Antagonists; D004967:Estrogens; D009596:Nitrophenols; D001335:Vehicle Emissions; C008636:4-nitro-3-cresol; D012822:Silicon Dioxide