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Molecules, Volume 19, Issue 1 (January 2014), Pages 1-1377

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Open AccessEditorial Molecules Best Paper Award 2014
Molecules 2014, 19(1), 1375-1377; https://doi.org/10.3390/molecules19011375
Received: 6 December 2013 / Revised: 11 December 2013 / Accepted: 17 December 2013 / Published: 22 January 2014
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Abstract
Molecules instituted some years ago a “Best Paper” award to recognize the most outstanding papers in the area of natural products, medicinal chemistry and molecular diversity published each year in Molecules. We are pleased to announce the third “Molecules Best Paper
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Molecules instituted some years ago a “Best Paper” award to recognize the most outstanding papers in the area of natural products, medicinal chemistry and molecular diversity published each year in Molecules. We are pleased to announce the third “Molecules Best Paper Award” for 2014. The winners were chosen by the Editor-in-Chief and selected editorial board members from among all the papers published in 2010. Reviews and research papers were evaluated separately. [...] Full article
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Open AccessCorrection Correction: Gao, W., et al. Efficient One-Pot Synthesis of 5-Chloromethyl-furfural (CMF) from Carbohydrates in Mild Biphasic Systems. Molecules 2013, 18, 7675-7685
Molecules 2014, 19(1), 1370-1374; https://doi.org/10.3390/molecules19011370
Received: 12 November 2013 / Revised: 13 January 2014 / Accepted: 13 January 2014 / Published: 22 January 2014
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Abstract
We have recently been made aware by Prof. Mark Mascal (University of California Davis) and the Molecules Editorial Offices of some errors and omissions in the Introduction section of our recent paper. [...] Full article
Open AccessLetter Comment on Gao, W., et al. “Efficient One-Pot Synthesis of 5-Chloromethylfurfural (CMF) from Carbohydrates in Mild Biphasic Systems”, Molecules 2013, 18, 7675-7685
Molecules 2014, 19(1), 1367-1369; https://doi.org/10.3390/molecules19011367
Received: 19 August 2013 / Revised: 2 January 2014 / Accepted: 2 January 2014 / Published: 22 January 2014
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Abstract
In a recent paper entitled “Efficient One-Pot Synthesis of 5-Chloromethylfurfural (CMF) from Carbohydrates in Mild Biphasic Systems,” published in Molecules [1], Gao and coworkers describe the use of a biphasic aq. HCl-H3PO4/CHCl3 reagent for the preparation of CMF
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In a recent paper entitled “Efficient One-Pot Synthesis of 5-Chloromethylfurfural (CMF) from Carbohydrates in Mild Biphasic Systems,” published in Molecules [1], Gao and coworkers describe the use of a biphasic aq. HCl-H3PO4/CHCl3 reagent for the preparation of CMF from various feedstocks. The maximum yield (46.8%) was obtained from fructose by reaction at 45 °C for 20 h. While sucrose gave a similar yield, the same reaction with glucose and cellulose gave 7.3% and 7.8% yields, respectively. Remarkably, the same process applied to Kraft pulp and powdered wood samples gave between 16.0% and 31.4% CMF, based on sugar content. Looking to the Experimental section for insight into this unusual outcome, the statement, “the procedure of treating lignocellulose sample (Table 6) was almost the same as the carbohydrate, except adding the selected simple 1.0 mg each trial [sic] appears, which is difficult to interpret. Full article
Open AccessArticle Molecular Dynamics of Neutral Polymer Bonding Agent (NPBA) as Revealed by Solid-State NMR Spectroscopy
Molecules 2014, 19(1), 1353-1366; https://doi.org/10.3390/molecules19011353
Received: 12 October 2013 / Revised: 3 January 2014 / Accepted: 16 January 2014 / Published: 22 January 2014
Cited by 3 | PDF Full-text (441 KB) | HTML Full-text | XML Full-text
Abstract
Neutral polymer bonding agent (NPBA) is one of the most promising polymeric materials, widely used in nitrate ester plasticized polyether (NEPE) propellant as bonding agent. The structure and dynamics of NPBA under different conditions of temperatures and sample processing are comprehensively investigated by
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Neutral polymer bonding agent (NPBA) is one of the most promising polymeric materials, widely used in nitrate ester plasticized polyether (NEPE) propellant as bonding agent. The structure and dynamics of NPBA under different conditions of temperatures and sample processing are comprehensively investigated by solid state NMR (SSNMR). The results indicate that both the main chain and side chain of NPBA are quite rigid below its glass transition temperature (Tg). In contrast, above the Tg, the main chain remains relatively immobilized, while the side chains become highly flexible, which presumably weakens the interaction between bonding agent and the binder or oxidant fillers and in turn destabilizes the high modulus layer formed around the oxidant fillers. In addition, no obvious variation is found for the microstructure of NPBA upon aging treatment or soaking with acetone. These experimental results provide useful insights for understanding the structural properties of NPBA and its interaction with other constituents of solid composite propellants under different processing and working conditions. Full article
(This article belongs to the Special Issue NMR of Proteins and Small Biomolecules)
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Open AccessArticle Synthesis and Characterization of Impurities of Barnidipine Hydrochloride, an Antihypertensive Drug Substance
Molecules 2014, 19(1), 1344-1352; https://doi.org/10.3390/molecules19011344
Received: 11 December 2013 / Revised: 15 January 2014 / Accepted: 15 January 2014 / Published: 21 January 2014
Cited by 3 | PDF Full-text (265 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Barnidipine hydrochloride is a long term dihydropyridine calcium channel blocker used for the treatment of hypertension. During the process development of barnidipine hydrochloride, four barnidipine impurities were detected by high-performance liquid chromatography (HPLC) with an ordinary column (Agilent ZORBAX Eclipse XDB-C18, 150 mm
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Barnidipine hydrochloride is a long term dihydropyridine calcium channel blocker used for the treatment of hypertension. During the process development of barnidipine hydrochloride, four barnidipine impurities were detected by high-performance liquid chromatography (HPLC) with an ordinary column (Agilent ZORBAX Eclipse XDB-C18, 150 mm × 4.6 mm, 5 µm). All these impurities were identified, synthesized, and subsequently characterized by their respective spectral data (MS, 1H-NMR, and 13C-NMR). The identification of these impurities should be useful for quality control in the manufacture of barnidipine. Full article
(This article belongs to the Section Organic Chemistry)
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Open AccessArticle EGF Receptor-Dependent Mechanism May be Involved in the Tamm–Horsfall Glycoprotein-Enhanced PMN Phagocytosis via Activating Rho Family and MAPK Signaling Pathway
Molecules 2014, 19(1), 1328-1343; https://doi.org/10.3390/molecules19011328
Received: 3 December 2013 / Revised: 13 January 2014 / Accepted: 16 January 2014 / Published: 21 January 2014
Cited by 6 | PDF Full-text (2126 KB) | HTML Full-text | XML Full-text
Abstract
Our previous studies showed that urinary Tamm–Horsfall glycoprotein (THP) potently enhanced polymorphonuclear neutrophil (PMN) phagocytosis. However, the domain structure(s), signaling pathway and the intracellular events responsible for THP-enhanced PMN phagocytosis remain to be elucidated. THP was purified from normal human urine. The human
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Our previous studies showed that urinary Tamm–Horsfall glycoprotein (THP) potently enhanced polymorphonuclear neutrophil (PMN) phagocytosis. However, the domain structure(s), signaling pathway and the intracellular events responsible for THP-enhanced PMN phagocytosis remain to be elucidated. THP was purified from normal human urine. The human promyelocytic leukemia cell line HL-60 was induced to differentiate into PMNs by all-trans retinoid acid. Pretreatment with different MAPK and PI3K inhibitors was used to delineate signaling pathways in THP-enhanced PMN phagocytosis. Phosphorylation of molecules responsible for PMN phagocytosis induced by bacterial lipopolysaccharide (LPS), THP, or human recombinant epidermal growth factor (EGF) was evaluated by western blot. A p38 MAPK inhibitor, SB203580, effectively inhibited both spontaneous and LPS- and THP-induced PMN phagocytosis. Both THP and LPS enhanced the expression of the Rho family proteins Cdc42 and Rac that may lead to F-actin re-arrangement. Further studies suggested that THP and EGF enhance PMN and differentiated HL-60 cell phagocytosis in a similar pattern. Furthermore, the EGF receptor inhibitor GW2974 significantly suppressed THP- and EGF-enhanced PMN phagocytosis and p38 and ERK1/2 phosphorylation in differentiated HL-60 cells. We conclude that EGF receptor-dependent signaling may be involved in THP-enhanced PMN phagocytosis by activating Rho family and MAP kinase. Full article
(This article belongs to the Special Issue Oligosaccharides and Glyco-Conjugates)
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Open AccessCommunication Antibacterial and Antioxidant Activities of Ursolic Acid and Derivatives
Molecules 2014, 19(1), 1317-1327; https://doi.org/10.3390/molecules19011317
Received: 7 November 2013 / Revised: 11 December 2013 / Accepted: 20 December 2013 / Published: 21 January 2014
Cited by 47 | PDF Full-text (212 KB) | HTML Full-text | XML Full-text
Abstract
Ursolic acid, an important bioactive compound, was isolated from ethanol extract of aerial parts of Sambucus australis. In order to develop bioactive ursolic acid derivatives, two semi-synthetic compounds were obtained through modification at C-3. The antibacterial activity of the ursolic acid and
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Ursolic acid, an important bioactive compound, was isolated from ethanol extract of aerial parts of Sambucus australis. In order to develop bioactive ursolic acid derivatives, two semi-synthetic compounds were obtained through modification at C-3. The antibacterial activity of the ursolic acid and its derivatives was investigated. The microdilution method was used for determination of the minimal inhibitory concentration (MIC), against twelve bacterial strains. The influence of ursolic acid and its derivatives on the susceptibility of some bacterial pathogens to the aminoglycosides antibiotics neomycin, amikacin, kanamycin and gentamicin was evaluated. The most representative synergistic effect was observed by 3β-formyloxy-urs-12-en-28-oic acid at the concentration of 64 μg/mL in combination with kanamycin against Escherichia coli (27), a multidrug-resistant clinical isolate from sputum, with reduction of MIC value from 128 μg/mL to 8 μg/mL. Ursolic acid and its derivatives were examined for their radical scavenger activity using the DPPH assay, and showed significant activity. Full article
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Open AccessArticle Crystal Structures, Vibrational Spectra, and Fungicidal Activity of 1,5-Diaryl-3-oxypyrazoles
Molecules 2014, 19(1), 1302-1316; https://doi.org/10.3390/molecules19011302
Received: 4 November 2013 / Revised: 9 January 2014 / Accepted: 14 January 2014 / Published: 21 January 2014
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Abstract
The aryloxypyrazole structure is present in a number of bioactive molecules. Four 1,5-diaryl-3-oxypyrazoles containing benzoyl (I), thiazolidinethione (II and III) or per-O-acetylated glucopyranosyl (IV) moieties were characterized by single-crystal X-ray diffraction. Compounds I and
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The aryloxypyrazole structure is present in a number of bioactive molecules. Four 1,5-diaryl-3-oxypyrazoles containing benzoyl (I), thiazolidinethione (II and III) or per-O-acetylated glucopyranosyl (IV) moieties were characterized by single-crystal X-ray diffraction. Compounds I and II crystallize in a triclinic P-1 system, whereas III and IV crystallize in an orthorhombic Pbca and a monoclinic P21 space groups, respectively. The dihedral angles between the two benzene rings of the pyrazole are 61.33° (I), 62.87° (II), 57.09° (III) and 70.25° (IV). The structures were stabilized by classical intra- (C-H···S for II and III, C-H···O for IV) and intermolecular (C-H···O for I and IV) H-bonds, as well as intermolecular C-H···π stacking interactions. The theoretical FTIR results showed good agreement with the experimental data. Compounds IV, II and III showed moderate fungicidal activity against Sclerotinia sclerotiorum and Gibberella zeae. The structure-activity relationships were discussed. Full article
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Open AccessArticle Synthesis of 4-Methoxybenzoylhydrazones and Evaluation of Their Antiglycation Activity
Molecules 2014, 19(1), 1286-1301; https://doi.org/10.3390/molecules19011286
Received: 17 December 2013 / Revised: 31 December 2013 / Accepted: 2 January 2014 / Published: 21 January 2014
Cited by 18 | PDF Full-text (295 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A series of 4-methoxybenzoylhydrazones 130 was synthesized and the structures of the synthetic derivatives elucidated by spectroscopic methods. The compounds showed a varying degree of antiglycation activity, with IC50 values ranging between 216.52 and 748.71 µM, when compared to a
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A series of 4-methoxybenzoylhydrazones 130 was synthesized and the structures of the synthetic derivatives elucidated by spectroscopic methods. The compounds showed a varying degree of antiglycation activity, with IC50 values ranging between 216.52 and 748.71 µM, when compared to a rutin standard (IC50 = 294.46 ± 1.50 µM). Compounds 1 (IC50 = 216.52 ± 4.2 µM), 3 (IC50 = 289.58 ± 2.64 µM), 6 (IC50 = 227.75 ± 0.53 µM), 7 (IC50 = 242.53 ± 6.1) and 11 (IC50 = 287.79 ± 1.59) all showed more activity that the standard, and these compounds have the potential to serve as possible leads for drugs to inhibit protein glycation in diabetic patients. A preliminary SAR study was performed. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessReview Oxidized Fatty Acids as Inter-Kingdom Signaling Molecules
Molecules 2014, 19(1), 1273-1285; https://doi.org/10.3390/molecules19011273
Received: 26 December 2013 / Revised: 16 January 2014 / Accepted: 16 January 2014 / Published: 20 January 2014
Cited by 15 | PDF Full-text (1196 KB) | HTML Full-text | XML Full-text
Abstract
Oxylipins or oxidized fatty acids are a group of molecules found to play a role in signaling in many different cell types. These fatty acid derivatives have ancient evolutionary origins as signaling molecules and are ideal candidates for inter-kingdom communication. This review discusses
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Oxylipins or oxidized fatty acids are a group of molecules found to play a role in signaling in many different cell types. These fatty acid derivatives have ancient evolutionary origins as signaling molecules and are ideal candidates for inter-kingdom communication. This review discusses examples of the ability of organisms from different kingdoms to “listen” and respond to oxylipin signals during interactions. The interactions that will be looked at are signaling between animals and plants; between animals and fungi; between animals and bacteria and between plants and fungi. This will aid in understanding these interactions, which often have implications in ecology, agriculture as well as human and animal health. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Inhibition of Epstein-Barr Virus Lytic Cycle by an Ethyl Acetate Subfraction Separated from Polygonum cuspidatum Root and Its Major Component, Emodin
Molecules 2014, 19(1), 1258-1272; https://doi.org/10.3390/molecules19011258
Received: 11 December 2013 / Revised: 9 January 2014 / Accepted: 14 January 2014 / Published: 20 January 2014
Cited by 9 | PDF Full-text (1623 KB) | HTML Full-text | XML Full-text
Abstract
Polygonum cuspidatum is widely used as a medicinal herb in Asia. In this study, we examined the ethyl acetate subfraction F3 obtained from P. cuspidatum root and its major component, emodin, for their capacity to inhibit the Epstein-Barr virus (EBV) lytic cycle. The
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Polygonum cuspidatum is widely used as a medicinal herb in Asia. In this study, we examined the ethyl acetate subfraction F3 obtained from P. cuspidatum root and its major component, emodin, for their capacity to inhibit the Epstein-Barr virus (EBV) lytic cycle. The cell viability was determined by the MTT [3-(4,5-dimethyldiazol-2-yl)-2,5-diphenyltetrazolium bromide] method. The expression of EBV lytic proteins was analyzed by immunoblot, indirect immunofluorescence and flow cytometric assays. Real-time quantitative PCR was used to assess the EBV DNA replication and the transcription of lytic genes, including BRLF1 and BZLF1. Results showed that the F3 and its major component emodin inhibit the transcription of EBV immediate early genes, the expression of EBV lytic proteins, including Rta, Zta, and EA-D and reduces EBV DNA replication, showing that F3 and emodin are potentially useful as an anti-EBV drug. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Two New Secondary Metabolites from Xylaria sp. cfcc 87468
Molecules 2014, 19(1), 1250-1257; https://doi.org/10.3390/molecules19011250
Received: 5 December 2013 / Revised: 15 January 2014 / Accepted: 15 January 2014 / Published: 20 January 2014
Cited by 3 | PDF Full-text (286 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A new isocoumarin glycoside, 3R-(+)-5-O-[6'-O-acetyl]-α-D-glucopyranosyl-5-hydroxymellein (1), and a new phenylethanol glycoside, (−)-phenylethyl-8-O-α-L-rhamno-pyranoside (2), were isolated from the ethyl acetate extract of the fungus Xylaria sp. cfcc 87468,
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A new isocoumarin glycoside, 3R-(+)-5-O-[6'-O-acetyl]-α-D-glucopyranosyl-5-hydroxymellein (1), and a new phenylethanol glycoside, (−)-phenylethyl-8-O-α-L-rhamno-pyranoside (2), were isolated from the ethyl acetate extract of the fungus Xylaria sp. cfcc 87468, together with five known steroids, β-sitosterol (3), stigmast-4-en-3-one (4), ergosterol (5), (22E)-cholesta-4,6,8(14),22-tetraen-3-one (6), and 4α-methyl- ergosta-8(14),24(28)-dien-3β-ol (7). The structures of compounds 1 and 2 were elucidated by MS, extensive 1D and 2D NMR spectroscopy, and the circular dichroism (CD) spectroscopy. Full article
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Open AccessArticle Construction of the 1,2-Dialkenylcyclohexane Framework via Ireland-Claisen Rearrangement and Intramolecular Barbier Reaction: Application to the Synthesis of (±)-Geijerone and a Diastereoisomeric Mixture with Its 5-Epimer
Molecules 2014, 19(1), 1238-1249; https://doi.org/10.3390/molecules19011238
Received: 17 December 2013 / Revised: 14 January 2014 / Accepted: 15 January 2014 / Published: 20 January 2014
Cited by 2 | PDF Full-text (255 KB) | HTML Full-text | XML Full-text
Abstract
The elemene-type terpenoids, which possess various biological activities, contain a syn- or anti-1,2-dialkenylcyclohexane framework. An efficient synthetic route to the syn- and anti-1,2-dialkenylcyclohexane core and its application in the synthesis of (±)-geijerone and its diastereomer is reported. Construction of
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The elemene-type terpenoids, which possess various biological activities, contain a syn- or anti-1,2-dialkenylcyclohexane framework. An efficient synthetic route to the syn- and anti-1,2-dialkenylcyclohexane core and its application in the synthesis of (±)-geijerone and its diastereomer is reported. Construction of the syn- and anti-1,2-dialkenyl moiety was achieved via Ireland-Claisen rearrangement of the (E)-allylic ester, and the cyclohexanone moiety was derived from the iodoaldehyde via intramolecular Barbier reaction. The synthetic strategy allows rapid access to various epimers and analogues of elemene-type products. Full article
(This article belongs to the Section Organic Chemistry)
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Open AccessArticle Synthesis of Tetrahydrohonokiol Derivates and Their Evaluation for Cytotoxic Activity against CCRF-CEM Leukemia, U251 Glioblastoma and HCT-116 Colon Cancer Cells
Molecules 2014, 19(1), 1223-1237; https://doi.org/10.3390/molecules19011223
Received: 9 December 2013 / Revised: 9 January 2014 / Accepted: 13 January 2014 / Published: 20 January 2014
Cited by 10 | PDF Full-text (280 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Biphenyl neolignans such as honokiol and magnolol, which are the major active constituents of the Asian medicinal plant Magnolia officinalis, are known to exert a multitude of pharmacological and biological activities. Among these, cytotoxic and tumor growth inhibitory activity against various tumour
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Biphenyl neolignans such as honokiol and magnolol, which are the major active constituents of the Asian medicinal plant Magnolia officinalis, are known to exert a multitude of pharmacological and biological activities. Among these, cytotoxic and tumor growth inhibitory activity against various tumour cell lines are well-documented. To further elucidate the cytotoxic effects of honokiol derivatives, derivatizations were performed using tetrahydrohonokiol as a scaffold. The derivatizations comprised the introduction of functional groups, e.g., nitro and amino groups, as well as alkylation. This way, 18 derivatives, of which 13 were previously undescribed compounds, were evaluated against CCRF-CEM leukemia cells, U251 glioblastoma and HCT-116 colon cancer cells. The results revealed no significant cytotoxic effects in any of the three tested cell lines at a test concentration of 10 µM. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Simultaneous Determination of 24 Antidepressant Drugs and Their Metabolites in Wastewater by Ultra-High Performance Liquid Chromatography–Tandem Mass Spectrometry
Molecules 2014, 19(1), 1212-1222; https://doi.org/10.3390/molecules19011212
Received: 7 November 2013 / Revised: 14 January 2014 / Accepted: 15 January 2014 / Published: 20 January 2014
Cited by 11 | PDF Full-text (913 KB) | HTML Full-text | XML Full-text
Abstract
Antidepressants are a new kind of pollutants being increasingly found in wastewater. In this study, a fast and sensitive ultra-high performance liquid chromatography-tandem mass spectrometry method was developed and validated for the analysis of 24 antidepressant drugs and six of their metabolites in
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Antidepressants are a new kind of pollutants being increasingly found in wastewater. In this study, a fast and sensitive ultra-high performance liquid chromatography-tandem mass spectrometry method was developed and validated for the analysis of 24 antidepressant drugs and six of their metabolites in wastewater. This is the first time that the antidepressant residues in wastewater of Beijing (China) were systematically reported. A solid-phase extraction process was performed with 3 M cation disk, followed by ultra-high performance liquid chromatography–tandem mass spectrometry measurements. The chromatographic separation and mass parameters were optimized in order to achieve suitable retention time and good resolution for analytes. All compounds were satisfactorily determined in one single injection within 20 min. The limit of quantification (LOQ), linearity, and extraction recovery were validated. The LOQ for analytes were ranged from 0.02 to 0.51 ng/mL. The determination coefficients were more than 0.99 within the tested concentration range (0.1–25 ng/mL), and the recovery rate for each target compound was ranged from 81.2% to 118% at 1 ng/mL. This new developed method was successfully applied to analysis the samples collected from Beijing municipal wastewater treatment plants. At least ten target antidepressants were found in all samples and the highest mean concentration of desmethylvenlafaxin was up to 415.6 ng/L. Full article
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