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Simultaneous Determination of Daidzein, Genistein and Formononetin in Coffee by Capillary Zone Electrophoresis

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Simultaneous Determination of Daidzein, Genistein and Formononetin in Coffee by Capillary Zone Electrophoresis separations Article Simultaneous Determination of Daidzein, Genistein and Formononetin in Coffee by Capillary Zone Electrophoresis Feng Luan *, Li Li Tang, Xuan Xuan Chen and Hui Tao Liu College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China; [email protected] (L.L.T.); [email protected] (X.X.C.); [email protected] (H.T.L.) * Correspondence: fl[email protected]; Tel.: +86-535-6902063 Academic Editor: Doo Soo Chung Received: 29 October 2016; Accepted: 20 December 2016; Published: 1 January 2017 Abstract: Coffee is a favorite and beverage in Western countries that is consumed daily. In the present study, capillary zone electrophoresis (CE) was applied for the separation and quantification of three isoflavones including daidzein, genistein and formononetin in coffee. Extraction of isoflavones from the coffee sample was carried out by extraction and purification process using ether after the acid hydrolysis with the antioxidant butylated hydroxy-toluene (BHT). The experimental conditions of the CE separation method were: 20 mmol/L Na2HPO4 buffer solution, 25 kV applied voltage, 3 s hydrodynamic injection at 30 mbar, and UV detection at 254 nm. The results show that the three compounds can be tested within 10 min with a linearity of 0.5–50 µg/mL for all three compounds. The limits of detection were 0.0642, 0.134, and 0.0825 µg/mL for daidzein, formononetin and genistein, respectively. The corresponding average recovery was 99.39% (Relative Standard Detection (RSD) = 1.76%), 98.71% (RSD = 2.11%) and 97.37% (RSD = 3.74%). Keywords: capillary zone electrophoresis (CE); daidzein; genistein; formononetin; acid hydrolysis 1. Introduction Phytoestrogens (PEs), also called “dietary estrogens”, are a group of natural, non-steroidal, estrogen-like compounds found in a wide variety of plants consumed by humans [1]. Currently, four different groups of plant phenolics are considered PEs, including isoflavones and lignans, coumestanes, flavonoids and stilbenes. Other less-investigated compounds include prenylflavonoids, flavones, flavans and phytosterol esters [2]. These compounds are similar to 17β-estradiol in structure and function [3]. They have a dual-directional regulation function in the human body, meaning both anti-estrogen activity and estrogenic activity [4]. Such compounds have good curative effects for the treatment of cardiovascular disease, breast cancer, Alzheimer’s disease, neurodegenerative disorders, and osteoporosis, etc. [5–8]. They can also be used for the treatment of the symptoms of menopause [9]. PEs are common in nature and have many pharmacological activities [9,10]. It has been reported that the daily take of PEs for menopausal women in the Caucasus region of the United States is no more than one milligram [11]. There are some foods that contain PEs including: soybeans and soy products, tempeh, linseeds, sesame seeds, wheat berries, fenugreek, oats, barley, beans, lentils, yams, rice, alfalfa, mung beans, apples, carrots, pomegranates [12], wheat germ, rice bran, lupin, kudzu, coffee, licorice root, mint, ginseng, hops [13], bourbon, beer [14], fennel and anise [15]. As we know, the content of PEs is different between various foods. In addition, it may also occur in the same kinds of foods, such as soy beverages and tofu, since they are made of different kinds of raw materials or using different processing methods [16]. It has been proved that phytoestrogen-rich diets include soybeans and soybean products, followed by legumes, nuts, oilseeds, fruits and vegetables [17]. As is well known, there is a phenomenon Separations 2017, 4, 1; doi:10.3390/separations4010001 www.mdpi.com/journal/separations Separations 2017, 4, 1 2 of 8 It has been proved that phytoestrogen-rich diets include soybeans and soybean products, followedSeparations 2017by , 4legumes,, 1 nuts, oilseeds, fruits and vegetables [17]. As is well known, there 2is of a 8 phenomenon where people consume less soy and its derivatives in Western countries than in whereEastern people ones [ consume18]. However, less soy coffee and is its a derivativesfavorite beverage in Western in Western countries countries than in that Eastern is consumed ones [18]. daily;However, for example, coffee is a in favorite the United beverage States, in Western29 September countries is celebrated that is consumed as “Nat daily;ional forCoffee example, Day” in [19 the]. Thus,United it States,is necessary 29 September to study is the celebrated content of as isoflavones “National Coffee in coffee. Day” [19]. Thus, it is necessary to study the contentSome researchers of isoflavones have in coffee.been studied the phytoestrogens in plants [20]. The methods used for the determinationSome researchers of phytoestrogens have been studied in theplants phytoestrogens are GC-MS in[21,22 plants], HPLC [20]. The [17,23 methods–31], and used LC for-MS the [32,33determination]. It should of be phytoestrogens noted that HPLC in plants separation are GC-MS is generally [21,22 carried], HPLC out [17 on,23 reversed–31], and-phaseLC-MS columns [32,33]. usingIt should the bemethanol noted that of acetonitrile HPLC separation and water is generally containing carried small out amounts on reversed-phase of acid as a columns modifier using [29]. theAs farmethanol as we ofknow, acetonitrile few studies and water have containing been reported small amounts using capillary of acid as zone a modifier electrophoresis [29]. As far (CE) as we in know, the analysisfew studies of haveisoflavones. been reported Aramendia using et capillary al. [34] zone separated electrophoresis and identified (CE) in several the analysis isoflavones of isoflavones. using AramendiaCE-ESI/MS etin al. negative [34] separated ion mode and identifiedfrom standard several samples. isoflavones García using-Villalba CE-ESI/MS et al. in [35 negative] used ioncapillary mode electrophoresisfrom standard samples.–time-of-flight García-Villalba-mass spectrometry et al. [35] used to compare capillary the electrophoresis–time-of-flight-mass metabolic profiles of conventional andspectrometry genetically to comparemodified the soybeans, metabolic including profiles of isoflavones, conventional amino and genetically acids, carboxylic modified acids soybeans, and peptides.including isoflavones,In the above amino references, acids, carboxylicseparation acids was andcarried peptides. out in In positive the above mode references, at pH separation9–9.5 and wasdetection carried was out achieved in positive in modenegative at pHionization 9–9.5 and mode, detection but quantification was achieved inwas negative not reported. ionization Also, mode, the processbut quantification is somewhat was time not- reported.consuming Also,, though the process it is useful is somewhat and effective. time-consuming, though it is useful and effective.From the works reported so far, one can see that the quantitative determination of isoflavones in plantFroms is themostly works done reported by HPLC so far, combined one can with see thatacid the hydrolysis quantitative or alcohol determination extraction. of In isoflavones addition, thein plants separation is mostly system done is acid by HPLCic. The combined HPLC method with aciduses hydrolysis a large amount or alcohol of organic extraction. solvent In in addition, mobile phasethe separation and requires system a long is acidic. separation The HPLC time. method The acid uses hydrolysis a large amount and ethanol of organic extraction solvent are in simple mobile; however,phase and the requires process a longcannot separation transform time. glycosides The acid into hydrolysis aglycone. and Also, ethanol the acid extraction hydrolysis are process simple; mayhowever, lead theto processthe samples cannot contain transforming glycosidesa large number into aglycone. of complex Also,es theand acid it is hydrolysis difficult processto separate may substanceslead to the samplesafter they containing are treated a by large acid number hydrolysis. of complexes and it is difficult to separate substances afterThe they aim are treatedof this bywork acid was hydrolysis. to develop a simple, efficient and sensitive CE method, as an alternativeThe aim to ofother this workmethods was, tofor develop the quantitative a simple, efficientanalysis andof three sensitive isoflavones, CE method, including as an alternative daidzein, genisteinto other methods, and formononetin for the quantitative (their chemical analysis structures of three isoflavones,are shown in including Figure 1 daidzein,) in coffee. genistein For this, andwe improvedformononetin the (theirextraction chemical method structures of isoflavones are shown from in Figure the coffee1) in coffee. sample For with this, an we extracti improvedon and the purifextractionication method process of using isoflavones ether frominstead the of coffee ethanol sample after with the anprocess extraction of acid and hydrolysis purification with process the antioxidantusing ether butylated instead of hydroxy ethanol- aftertoluene the (BHT). process The of acidproposed hydrolysis method with was the successfully antioxidant applied butylated to thehydroxy-toluene determination (BHT).of three The isoflavones proposed in methodcommercially was successfully available coffee applied samples. to the To determination our knowledge, of therethree isoflavonesare no methods in commercially that describe available the quantification coffee samples. of isoflavones To our knowledge, in coffee there samples are no using methods the singlethat describe CE. Also, the the quantification sample preparation
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