Photoreduction fluorescence detection of quinones in high-performance liquid chromatography

Poulsen, James R.; Birks, John W.

doi:10.1021/ac00195a012

Cited by 61 publications

(23 citation statements)

References 53 publications

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“…Quantitative analytical methods for quinones have been developed using several techniques including high-performance liquid chromatographic (HPLC) with ultraviolet (UV) [11], fluorescence [12,13], electrochemical [14], chemiluminescence (CL) [15,16], and mass spectrometry (MS) detection [17,18]. Gas chromatography with MS detection was also reported for the determination of quinones [19][20][21][22][23][24][25].…”

Section: Introductionmentioning

confidence: 99%

An ultrasensitive and highly selective determination method for quinones by high-performance liquid chromatography with photochemically initiated luminol chemiluminescence

Ahmed

Kishikawa

Ohyama

et al. 2009

Journal of Chromatography A

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Quinones are a class of compounds of substantial toxicological and pharmacological interest. An ultrasensitive and highly selective chemiluminescence (CL) method was newly developed for the determination of quinones based on the utility of photochemically initiated luminol CL. The method involves ultraviolet (UV) irradiation of quinones to generate reactive oxygen species (ROS) through the unique photosensitization reaction accompanied with the photolytical generation of 3,6-dihydroxyphthalic acid (DHPA) from quinones. The photoproducts were detected by luminol CL reaction. Interestingly, it was noticed that DHPA had enhancement effect for the luminol CL. The generation of the enhancer (DHPA) in association with the oxidant (ROS) in the photochemical reaction greatly increases the sensitivity and selectivity of the proposed luminol CL method. In order to elucidate the type of ROS produced by the photosensitizaion reaction in relation to the proposed CL reaction, we investigated the quenching effect of selective ROS scavengers in the luminol CL. Although several ROS were generated, superoxide anion was the most effective ROS for the generated CL. Moreover, the enhancement mechanism of DHPA for luminol CL was confirmed. The enhancement was found to be through the formation of stabilized semiquinone anion radical that provided long-lived CL. The generation of the semiquinone radical was confirmed by electron spin resonance technique. Furthermore, we developed an HPLC method with on-line photochemical reaction followed by the proposed CL detection for the determination of four quinones. A luminol analogue, L-012, was used for its high sensitivity. The detection limits for quinones obtained with the proposed method (S/N=3) were in the range 1.5-24 fmol that were 10-1000 times more sensitive compared with the previous methods. Finally, the developed HPLC-CL system was successfully applied for the determination of quinones in airborne particulate samples collected at Nagasaki city.

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Section: Introductionmentioning

confidence: 99%

An ultrasensitive and highly selective determination method for quinones by high-performance liquid chromatography with photochemically initiated luminol chemiluminescence

Ahmed

Kishikawa

Ohyama

et al. 2009

Journal of Chromatography A

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“…1,2) Some naturally-occurring anthraquinones have already been examined by thin layer chromatography, 3) HPLC methods, [4][5][6][7][8] and capillary electrophoresis (CE), [9][10][11][12][13][14] however, only a single component or limited components have been determined in the majority of them. A few simultaneous analyses of different types of components have been conducted.…”

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confidence: 99%

Simultaneous Determination of Anthraquinones, Their 8-.BETA.-D-Glucosides, and Sennosides of Rhei Rhizoma by Capillary Electrophoresis

Koyama

Morita

Fujiyoshi

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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In a continuation of our work on quinones that occur widely in the plant kingdom and that may have biological activities, we have developed a simple cyclodextrin modified capillary zone electrophoresis (CD-CZE) to separate and determine emodin, chrysophanol, aloe-emodin, rhein, emodin-8-b-D-glucoside, chrysophanol-8-b-D-glucoside, rhein-8-b-Dglucoside, sennoside A, and sennoside B of Rhei Rhizoma. Rhei Rhizoma is an old-and well-known herbal medicine known for its purgative effect due to anthracene derivatives, especially their glycosides. The analysis of these compounds and anthraquinones in pharmaceutical preparations or in complex matrices such as crude plant extracts is, therefore, of special interest.1,2) Some naturally-occurring anthraquinones have already been examined by thin layer chromatography, 3) HPLC methods, [4][5][6][7][8] and capillary electrophoresis (CE), [9][10][11][12][13][14] however, only a single component or limited components have been determined in the majority of them. A few simultaneous analyses of different types of components have been conducted. 6,8,14) Studies related to simultaneous determination by CE are especially rare. Rhei Rhizoma contains a wide variety of components, including monomeric anthraquinones, their glycosides, and dimeric anthrone glycosides, and thus simultaneous determination of these different groups of components showing large differences in polarity is desirable for the quality control of the herb. For this purpose, we have developed a simple and rapid CD-CZE method (except for rhein) using 0.005 M a-CD in 0.03 M borate buffer (pH 10.0) containing 20% acetonitrile. ExperimentalReagents and Materials Sodium tetraborate, sodium dodecyl sulphate (SDS), sodium hydroxide, hydroxypropyl-b-CD (HP-b-CD), g-CD, and HPg-CD were purchased from Wako Pure Chemicals (Osaka, Japan), a-CD, b-CD, and sennoside A (8) from Nacalai Tesque (Kyoto, Japan), sennoside B (9) from Funakoshi (Tokyo, Japan), and boric acid from Fluka (Buchs, Switzerland). Acetonitrile, methanol, and water were of HPLC grade. Emodin (1) and chrysophanol (2) were isolated from the root bark of Cassia siamea.15) Emodin-8-b-D-glucoside (5) was isolated from the root of Polygonum cuspidatum SIEB. et ZUCC. 16,17) and chrysophanol-8-b-D-glucoside (6) from Cascara Sagrada (the root of Rhamnus purshiana DC.).18,19) Aloeemodin (3), rhein (4), and rhein-8-b-D-glucoside (7) were isolated from Rhei Rhizoma 20) (Fig. 1). Rhei Rhizoma (Rheum palmatum L., Rheum tanguticum MAXIM.) was purchased from The Iguchi Pharmacy (Kobe, Japan).Procedure for CE The CE analyses were carried out using a Beckman MDQ and P/ACE System 5000 apparatus (Fullerton, CA, U.S.A.) equipped with a UV detector set at 254 nm, a diode array detector, and a Beckman untreated fused-silica capillary (570 mmϫ75 mm i.d.; 500 mm effective length). The analytical conditions were as follows: sampling time, 5 s (hydrodynamic mode; 0.5 p.s.i.); applied constant voltage, 20 kV; column temperature, 20°C. The CD-CZE electrolyte was a buffer solution prepared b...

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“…Although the high sensitivity achieved by the fluorescence detection, quinones lack native fluorescence and have to be reduced to their hydroquinone form prior to fluorescence detection. Different procedures are used for quinone reduction, either chemically, [13][14][15] electrochemically 16 or photochemically 17,18 . Although the fluorescence detection may accomplish the required sensitivity, the methods lacked simplicity and rapidity because the reduction processes required many additional systems component such as reducing column, electric reactor or photoreactor.…”

Section: Introductionmentioning

confidence: 99%

Microplate analytical method for quinones by pulse photo-irradiation and chemiluminescence detection

Elgawish

Shimomai

Kishikawa

et al. 2012

Analyst

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Quinones are widely distributed in the nature and have various bioactivities. Besides, quinones also considered as toxicological intermediates which cause a severe dangerous effects. Hereby, sensitive, simple, and rapid method is reported for quinones determination.The proposed method employed time resolved fluorescence (TRF) microplate reader based chemiluminescent (CL) detection for the first time as a novel approach for measurement.Under pulse photo-irradiation, the unique photochemical characteristic of quinones is exploited to liberate reactive oxygen species (ROS) which reacted with photosensitized CL reagent. L-012, luminol analogue, was selected for its high sensitivity. Under our investigation, para-quinones showed high CL response when compared to ortho-quinones. A linear response was obtained for studied quinone concentrations in the range of 0.05-50 µM for 1,4-naphthquinone and of 0.05-150 µM for 2-methyl-1,4-naphthoquinone and 9,10-anthraquinone with detection limit (balnk + 3SD) of 0.01 µM. The proposed method allowed the rapid determination of large number of samples in very short time (96 sample/ 125 sec).The proposed method was successfully applied for determination of menadione in spiked human serum.

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Photoreduction fluorescence detection of quinones in high-performance liquid chromatography

Cited by 61 publications

References 53 publications

An ultrasensitive and highly selective determination method for quinones by high-performance liquid chromatography with photochemically initiated luminol chemiluminescence

An ultrasensitive and highly selective determination method for quinones by high-performance liquid chromatography with photochemically initiated luminol chemiluminescence

Simultaneous Determination of Anthraquinones, Their 8-.BETA.-D-Glucosides, and Sennosides of Rhei Rhizoma by Capillary Electrophoresis

Microplate analytical method for quinones by pulse photo-irradiation and chemiluminescence detection

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