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Effect of Thermal Heating on Some Lignans in Flax Seeds, Sesame

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Effect of Thermal Heating on Some Lignans in Flax Seeds, Sesame Food Chemistry 138 (2013) 1847–1855 Contents lists available at SciVerse ScienceDirect Food Chemistry journal homepage: www.elsevier.com/locate/foodchem Analytical Methods Effect of thermal heating on some lignans in flax seeds, sesame seeds and rye ⇑ Eva Gerstenmeyer a, Sigrid Reimer a, Emmerich Berghofer b, Heidi Schwartz a,1, Gerhard Sontag a, a Institute for Analytical Chemistry, University of Vienna, Währinger Straße 38, A-1090 Vienna, Austria b Department of Food Science and Technology, University of Natural Resources and Life Sciences, Muthgasse 18, A-1190 Vienna, Austria article info abstract Article history: Consumption of lignan rich food is presumed to have positive effects on human health. As numerous Received 12 April 2012 foods are consumed mainly in processed form it is important to investigate the changes of the lignan con- Received in revised form 4 November 2012 tent during processing. To this end, unheated and heated sesame seeds, sesame products, rye grains, rye Accepted 20 November 2012 flour, rye bread and flax seeds were extracted by sonication with ethanol/water (70:30, v:v) or sodium Available online 5 December 2012 methoxide. The extracts were additionally hydrolysed enzymatically (b-glucuronidase/arylsulphatase, cellulase), the compounds separated on a reversed phase column by gradient elution and detected by Keywords: UV/ESI-MS in the negative ionisation multiple reaction monitoring mode (MRM). Secoisolariciresinol, lar- HPLC/UV–ESI-MS analysis iciresinol, pinoresinol, 7-hydroxymatairesinol, syringaresinol, isolariciresinol, secoisolariciresinol digly- Lignans Heated rye coside, lariciresinol monoglycoside, pinoresinol mono-, di- and triglycoside, sesaminol, sesaminol Sesame seeds triglycoside, sesamolinol and sesamolinol diglycoside were identified. Flax seeds Moderate heating at 100 °C did not degrade the lignan aglycones and glycosides in dry foods. In con- Commercial products trast, heating was responsible for the better extractability of the lignans. If samples with high moisture content were heated, the degradation of the lignans in sesame seeds and rye was observed already at 100 °C. Higher roasting temperatures caused degradation of aglycones and glycosides. Especially at 250 °C, lignans were degraded rapidly in sesame seeds and rye but not in flax seeds. Ó 2012 Elsevier Ltd. All rights reserved. 1. Introduction 2010). Infrared roasting of sesame seeds at 200 °C for 30 min also degraded sesamolin to sesamol (Kumar, Appu Pao, & Singh, 2009). Lignans are phytoestrogens present in seeds, vegetable oils, In sesame oil the content of sesamol increased under heating cereals, legumes, fruits and vegetables as aglycones, glycosides, conditions whilst that of sesamolin decreased slightly and the se- esterified glycosides or as bio-oligomers (Bambagiotti-Alberti, samin content changed only little. Sesamolin also degraded when Coran, Ghiara, Moneti, & Raffaelli, 1994; Coran, Giannellini, & the oil was heated at 200 °C for 20 min (Wu, 2007). For pinoresinol Bambagiotti-Alberti, 1996; Johnsson et al., 2002; Kamal-Eldin a high stability to thermal treatments below 180 °C was observed et al., 2001; Schwartz & Sontag, 2006; Smeds et al., 2007). in olive oil (Brenes, Garcia, Dobarganes, Velasco, & Romero, Frequently occurring lignans are lariciresinol, pinoresinol, secoisol- 2002). However, a short microwave treatment already resulted in ariciresinol, syringaresinol, matairesinol, 7-hydroxymatairesinol, a small decrease (Cerretani, Bendini, Rodriguez-Estrada, Vittadini, sesamin, sesamolin and sesamol. Plant foods or oils are used for & Chiavaro, 2009). Daskalaki, Kefi, Kotsiou, and Tasioula-Margari preparing various foods like bakery products, chips or blanched (2009) reported that lignans like 1-acetoxypinoresinol remained and cooked vegetables. During their production, the raw materials unchanged during boiling or frying in olive oil. Lee et al. (2003) are heated to a lesser or greater extent and the stability of lignans showed that simple heat treatment could not cleave covalently occurring in different conjugation patterns is influenced. bound phenolic compounds from rice hull, while far infrared treat- Roasting of sesame seeds at 200 °C for 60 min cleaved and lib- ment could. In pumpkin seeds, secoisolariciresinol was degraded erated phenolic compounds (Jeong et al., 2004), and sesamolin by thermal heating with increasing roasting time (Murkovic could be degraded into sesamol (Lee, Jeung, Park, Lee, & Lee, et al., 2004). Muir and Westcott (2000) and Hyvarinen et al. (2006) reported that the complex ester of secoisolariciresinol dig- lucoside and secoisolariciresinol diglucoside (SDG) itself are stable ⇑ Corresponding author. Tel.: +43 1 4277552303; fax: +43 1 42779523. in various bakery products. E-mail address: [email protected] (G. Sontag). Lignan consumption is believed to have positive effects on hu- 1 Current address: Christian Doppler Laboratory for Mycotoxin Metabolism and man health. Especially the benefits of secoisolariciresinol digluco- Center for Analytical Chemistry, Department for Agrobiotechnology (IFA-Tulln), side have been revealed recently (Adolphe, Whiting, Juurlink, University of Natural Resources and Life Sciences, Vienna, Konrad Lorenz Str. 20, A-3430 Tulln, Austria. Thorpe, & Alcorn, 2010; Touré & Xueming, 2010). In addition, the 0308-8146/$ - see front matter Ó 2012 Elsevier Ltd. All rights reserved. http://dx.doi.org/10.1016/j.foodchem.2012.11.117 1848 E. Gerstenmeyer et al. / Food Chemistry 138 (2013) 1847–1855 lignan metabolites enterodiol and enterolacton, produced by intes- 2.3. Substances, reagents and solutions tinal bacteria in a network of reactions, are proposed to be even more potent (Clavel, Dore, & Blaut, 2006) than the original plant Isolariciresinol (>95%) was obtained from Oy Separation Re- lignans. Therefore, the thermal stability of lignans during the pro- search (Turku, Finland), 7-hydroxymatairesinol (>95%), secoisola- duction of different foods is of great importance. riciresinol (>95%), lariciresinol (>95%), pinoresinol (>95%) and The variability of the conjugation pattern depending on the raw matairesinol (>95%) were from Arbo Nova (Turku, Finland) and product makes different sample preparation procedures necessary eleutheroside E (syringaresinol diglucoside) RotichromÒ was pur- (Schwartz & Sontag, 2011; Smeds et al., 2007). After extraction, the chased from Roth GmbH (Karlsruhe, Germany). b-Glucuronidase/ compounds are separated by gas chromatography (Liggins, arylsulphatase from Helix pomatia (5.5 U/ml) was delivered from Grimwood, & Bingham, 2000; Mazur et al., 1996; Penalvo, Haajanen, Roche Diagnostics GmbH (Mannheim, Germany). Cellulase Ono- Botting, & Adlercreutz, 2005), capillary zone electrophoresis zuka R-10 (1 U/mg) was obtained from Merck (Darmstadt, (Carrasco-Pancorbo, Neususs, Pelzing, Segura-Carretero, & Fernandez- Germany). Guitierrez, 2007; Carrasco-Pancorbo et al., 2006) and most fre- Acetonitrile and methanol (both HPLC gradient grade) were quently by reversed phase chromatography (Eliasson, Kamal-Eldin, purchased from VWR (Vienna, Austria), ethanol (99%) was from Andersson, & Aman, 2003; Kraushofer & Sontag, 2002a, 2002b; AustrAlco (Spillern Austria), methanol RotidryÒ (P99.9%), n- Kuhnle, Dell aquila, Low, Kussmaul, & Bingham, 2007; Milder hexane RotipuranÒ (P99%) and glacial acetic acid RotipuranÒ were et al., 2004; Moazzami, Anaresson, & Kamal-Eldin, 2006; Muir & from Roth GmbH (Karlsruhe, Germany), sodium hydroxide, p.a., Westcott, 2000; Nurmi et al., 2003; Obermeyer et al., 1995; zinc sulphate heptahydrate, p.a. and sodium acetate trihydrate Popova, Hall, & Kubatova, 2009; Schwartz & Sontag, 2006; Smeds, were purchased from Merck (Darmstadt, Germany). Metallic so- Jauhiainen, Tuomola, & Peltonen-Sainio, 2009; Smeds et al., 2007) dium was provided by the Institute of Organic Chemistry (Univer- coupled with different detection modes. Comprehensive reviews sity of Vienna). on the analysis of lignans have been published recently (Muir, Technical nitrogen and helium UN 1046 were from Airliquide 2006; Slanina & Glatz, 2004; Willfoer, Smeds, & Holmbom, 2006). Austria GmbH, (Schwechat, Austria). Purified water produced by The aim of this study was to investigate the thermal stability of a water purification system of Barnstead (Millipore, Bedford, MA, water soluble lignans in flax seeds, sesame seeds and rye. Due to USA) was used for all experiments and solutions. the lack of appropriate standard compounds for glycosides an analytical method was developed to estimate the SDG content 2.3.1. Stock solutions and to quantify the amount of aglycones. The content of lignans Two milligrams of isolariciresinol, secoisolariciresinol, larici- of some raw, heat treated and commercial products as well as resinol, pinoresinol, matairesinol and 7-hydroxymatairesinol were home baked bread should be determined to obtain information weighed and each of them transferred into a 10 ml flask and dis- on the concentration of the remaining lignans. solved in ethanol (99%). 2. Materials and methods 2.3.2. Syringaresinol stock solution Two milligrams of eleutheroside E (syringaresinol diglucoside) 2.1. Raw materials were transferred in a flask and dissolved in 10 ml methanol/water (50:50, v:v). To 1 ml of this solution, 3.5 ml sodium acetate (0.1 M, Three kg of sesame from Bolivia and hulled sesame premium adapted to pH 5 with glacial acetic acid) and 100 ll b-glucuroni- from India were provided by the Department of Food Science and dase/arylsulphatase were added
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