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New Liquid Chromatography: Mass Spectrometry Assay for Natural Phytoestrogens from Vegetable Extracts

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New Liquid Chromatography: Mass Spectrometry Assay for Natural Phytoestrogens from Vegetable Extracts Acta Chromatographica 23(2011)3, 509–520 DOI: 10.1556/AChrom.23.2011.3.11 New Liquid Chromatography: Mass Spectrometry Assay for Natural Phytoestrogens from Vegetable Extracts L. VLASE1, D.-S. POPA2,*, A. TERO-VESCAN3, AND N. OLAH4 1Department of Pharmaceutical Technology and Biopharmacy, Faculty of Pharmacy, “Iuliu Hatieganu” University of Medicine and Pharmacy, Emil Isac 13, RO-400023 Cluj-Napoca, Romania 2Department of Toxicology, Faculty of Pharmacy, “Iuliu Hatieganu” University of Medicine and Pharmacy, Emil Isac 13, RO-400023 Cluj-Napoca, Romania 3Department of Pharmaceutical Biochemistry, University of Medicine and Pharmacy, Gheorghe Marinescu 38, RO-540000 Targu-Mures, Romania 4Department of Drug Industry and Pharmaceutical Biotechnology, Faculty of Pharmacy, Vest University “Vasile Goldis” Arad and SC PlantExtrakt SRL, RO-407059 Radaia, Cluj, Romania E-mail: [email protected] Summary. A new liquid chromatography tandem mass spectrometry (LC-MS/MS) assay for the quantification of seven isoflavones (daidzin, genistin, ononin, daidzein, glycitein, genistein, and formononetin) and coumestrol in vegetable extracts was developed. The separation was performed on a Zorbax SB-C18 column with a mixture of methanol (solvent A) and 0.1% (v/v) acetic acid in water (solvent B) under gradient conditions at 50°C with a flow rate of 1 mL min−1. The detection of analytes was performed by electrospray ionization, negative ionisation, in non-reactive MS2 mode for aglycons or in reactive MS2 mode for glycosides. The method shows a good linearity (r2 > 0.9948) over the concentration range of 40–4000 ng mL−1 for all analytes, a good precision (CV < 11%) and accuracy (<10%). The method was successfully applied to quantify the isoflavones and coumestrol in vegetable extracts obtained from red clover (Trifolium pratense L., Fabaceae) and dyer’s greenweed (Genista tinctoria L., Fabaceae) and can be used in the chemical characterization of vegetables with phytoestrogen content. Key Words: phytoestrogens, isoflavones, LC-MS/MS, Trifolium pratense, Genista tinctoria Introduction In recent years, the knowledge of the positive health effects of vegetables has been increasing. Isoflavones, lignans and coumestans are compounds with polyphenolic structures that exhibit estrogenic and anti-estrogenic ac- tivity, anti-oxidant and anti-carcinogenic properties, and protective effects against a number of complex diseases, such as cardiovascular disease, os- teoporosis and menopausal symptoms [1, 2]. Soybeans are the most impor- tant natural source of genistein (4′,5,7-trihidroxyisoflavone) and daidzein (4′,7-dihidroxyisoflavone), which occur mainly as the glycosides genistin and daidzin. Other sources such as red clover (Trifolium pratense L., Fa- baceae) are rich in other aglycones such as formononetin, biochanin A, or 0231–2522 © 2011 Akadémiai Kiadó, Budapest Unauthenticated | Downloaded 10/02/21 08:52 AM UTC 510 L. Vlase et al. glycitein [1]. Red clover extracts offer the clinical benefits and represent an alternative to conventional hormone replacement therapy in menopausal disorders and hormone-dependent diseases [3]. Genista species (Fabaceae) show interesting biological properties such as hypoglycemic, anti- inflammatory, anti-ulcer, spasmolytic, anti-oxidant and estrogenic effects [4]. Dyer’s greenweed (Genista tinctoria L.) is rich in genistein [5, 6] and showed a protective effect against UV light, anti-oxidant activities and in- hibited the growth of melanoma cells in vitro [4]. There are many studies to quantify the phytoestrogen content in vege- table extracts or dietary supplements by HPLC [5, 7–10], GC-MS [11], and capillary electrophoresis [12, 13]. HPLC with UV detection is often chosen for routine analysis, but a preliminary acid or basic hydrolysis of isoflavone derivatives is required. The liquid chromatography tandem mass spec- trometry (LC-MS/MS) assay offers considerable advantages by its powerful performances: speed, selectivity, sensitivity, and robustness. It is the method preferred to identify isoflavone derivatives based on the fragmenta- tion pattern of the parent ion and in the quantification of isoflavones in complex mixtures [14]. The GC-MS methods required a supplementary step for derivatisation such as trimethylsilyl derivatives [11] that makes the analysis longer and more expensive. The aim of this work is to develop a new, simple, and efficient LC/MS- MS assay for the quantification of seven isoflavones (three glycosides: daidzin, genistin, and ononin, and four aglycones: daidzein, glycitein, gen- istein, and formononetin, respectively) and coumestrol (Fig. 1) from vegeta- ble extracts of red clover (T. pratense L.) and dyer’s greenweed (G. tinctoria L.) from Transylvania area, Romania. R1 R2 R3 R4 R1O O Daidzein H H H H Daidzin O-beta-D-GLU* H H H Genistein H H OH H R Genistin O-beta-D-GLU H OH H 2 Formononetin H H H CH3 Ononin O-beta-D-GLU H H CH3 R3 O Glycitein H OCH3 HH OR4 *GLU=glucosyl HO O O Coumestrol O OH Fig. 1. Chemical structures of analyzed phytoestrogens Unauthenticated | Downloaded 10/02/21 08:52 AM UTC New Liquid Chromatography 511 Experimental Reagents Genistein (4′,5,7-trihydroxyisoflavone), genistin, daidzein, ononin, and coumestrol of HPLC grade were reference standards from Fluka (Steinheim, Germany). Glycitein, daidzin, and formononetin standards of analytical re- agent grade were obtained from ChromaDex (the United States). Methanol of HPLC grade, acetic acid of analytical reagent grade, and 70% v/v ethanol of pharmaceutical grade were purchased from Merck KGaA (Darmstadt, Germany). Bidistilled, deionised water pro injections were purchased from Infusion Solution Laboratory of the University of Medicine and Pharmacy Cluj-Napoca (Romania). Apparatus The following apparatus were used: 204 Sigma Centrifuge (Osterode am Harz, Germany); Analytical Plus and Precision Standard Balance (Mettler- Toledo, Switzerland); Vortex Genie 2 mixer (Scientific Industries, New York); Ultrasonic bath Elma Transsonic 700/H (Singen, Germany). The HPLC system used was an 1100 series Agilent Technologies model (Darm- stadt, Germany) consisting of a G1312A binary pump, an in-line G1379A degasser, a G1329A autosampler, a G1316A column thermostat, and an Agilent Ion Trap Detector 1100 SL. Chromatographic and Mass Spectrometry Conditions Chromatographic separation was performed on a Zorbax SB-C18 (100 mm × 3.0 mm i.d., 5 μm) column (Agilent Technologies) equipped with a Zorbax SB-C18 precolumn with a mixture of methanol (solvent A) and 0.1% (v/v) acetic acid in water (solvent B) under gradient conditions (linear profile): 0 min—20% A, 2 min—20% methanol, 10 min—40% A, 10.5 min— 40% A, 11.5 min—45% A, 14.8 min—45% A, 15.8 min—100% A, at 50°C with a flow rate of 1 mL min−1. The detection of analytes was performed in non-reactive MS2 mode for the quantification of aglycons (only pseudo- molecular ion accumulation into ion trap, and then detection) or in reactive MS2 mode for the quantification of glycosides (accumulation and fragmen- tation of the pseudo-molecular ion, and then detection of fragments), nega- tive ion fragmentation, using an ion trap mass spectrometer equipped with an electrospray ionisation (ESI) ion source: capillary +2500 V, nebulizer Unauthenticated | Downloaded 10/02/21 08:52 AM UTC 512 L. Vlase et al. 65 psi (nitrogen), dry gas nitrogen at 12 L min−1, and dry gas temperature 360°C. Standard Solutions The stock solutions of daidzin, genistin, ononin, daidzein, genistein, for- mononetin, glycitein, and coumestrol (1 mg mL−1) were prepared by dis- solving the appropriate quantities in methanol. Two working solutions (4000 μg mL−1 and 400 ng mL−1) were prepared by appropriate dilution in water. These solutions were used to prepare calibration standards with the concentrations of 40, 80, 160, 320, 480, 960, 1920, and 4000 ng mL−1. To ver- ify the precision and accuracy of the method, five control standards of 40 ng mL−1 (lower limit of quantification [LLOQ]), 320 ng mL−1 (medium level) and 1920 ng mL−1 (higher level) were prepared. The resultant calibra- tion and control standards were preserved into 15 mL polypropylene tubes and stored at −4°C until analysis. Vegetable Samples The elaborated LC/MS-MS method was applied to quantify the eight poly- phenols in a tincture obtained from red clover (T. pratense L.) harvested from Cluj-Napoca area, Romania, and an extract obtained from dyer’s greenweed (G. tinctoria L.) harvested from Targu-Mures area, Romania. The T. pratense tincture was prepared from fresh herba using 14 g of 70% (v/v) ethanol to 10 g of fresh plant material, according to the 6th edition of the European Pharmacopoeia—mother tinctures for homeopathic prepa- rations [15]. The active compounds were extracted by cold extraction (mac- eration). The vegetal product and solvent were let to stand for 10 days in a dark place, with a short gentle stirring once daily. The tincture was ob- tained by pressing the plant–ethanol mixture and then filtering it. The G. tinctoria extract was prepared from dry herba using 100 mL of 75% (v/v) methanol to 5 g of dry plant material. The active compounds were extracted by refluxing for 4 h at 60°C. The extract was obtained by filtration of the plant–methanol mixture and then by completion at 100 mL. Quantification Method The concentrations of the eight analytes were determined automatically by the instrument data system using peak areas and the external standard method. The calibration curve model was determined by the quadratic analysis: y = ax2 + bx + c, where y is the peak area and x is analyte concen- tration. Unauthenticated | Downloaded 10/02/21 08:52 AM UTC New Liquid Chromatography 513 The LLOQ was established as the lowest calibration standard with an accuracy and a precision <20%. The precision (expressed as coefficient of variation, CV, %) and accu- racy (expressed as relative difference between obtained and theoretical con- centration, bias, %) were determined for 40 ng mL−1 (LLOQ), 320 ng mL−1 (medium level) and 1920 ng mL−1 (higher level) by the analysis of five dif- ferent standard solutions (n = 5) of these concentrations.
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