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Identification and Quantification of Glucosinolates in Korean Leaf Mustard Germplasm (Brassica Juncea Var

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Identification and Quantification of Glucosinolates in Korean Leaf Mustard Germplasm (Brassica Juncea Var Eur Food Res Technol (2016) 242:1479–1484 DOI 10.1007/s00217-016-2648-6 ORIGINAL PAPER Identification and quantification of glucosinolates in Korean leaf mustard germplasm (Brassica juncea var. integrifolia) by liquid chromatography–electrospray ionization/tandem mass spectrometry Heon Woong Kim1 · Ho Cheol Ko1 · Hyung Jin Baek1 · Soo Muk Cho1 · Hwan Hee Jang1 · Young Min Lee2 · Jung Bong Kim1 Received: 25 July 2015 / Revised: 11 January 2016 / Accepted: 29 January 2016 / Published online: 1 March 2016 © The Author(s) 2016. This article is published with open access at Springerlink.com Abstract In the present investigation, glucosinolate con- Interestingly, sinigrin and gluconasturtiin were present tent was identified and quantified in 210 accessions of in higher content, and progoitrin was not detected signifi- Korean leaf mustard (Brassica juncea var. integrifolia) by cantly in the germplasm of Korean leaf mustard. In particu- a liquid chromatography (LC) with electrospray ioniza- lar, accession K046197 (purple) was found to show highest tion (ESI) coupled with a positive-mode ion trap tandem total DS-GSL content (23.2 mg/g DW). mass spectrometry (LC–ESI–MS/MS). Eleven individual GSLs including two new compounds were identified in Keywords Evaluation · Glucosinolates · Korean leaf the accessions using desulfo-glucosinolates (DS-GSLs) mustard germplasm · Brassica juncea var. integrifolia · LC–MS library, and they were elucidated by interpreting LC–ESI–MS/MS the fragmentation data ([M H-glucose]+) obtained. The + newly identified GSLs contained aliphatic and hydroxyl functional group in their back bone were named as 1-ethyl- Introduction 2-hydroxyethyl DS-GSLs (glucosisautricin) or 2-hydroxy- 2-methylpropyl DS-GSLs (glucoconringiin) and 3,4,5-tri- Generally, plants produce a variety of toxic and repellent methoxybenzyl DS-GSLs, respectively. Among all tested secondary metabolites to protect themselves against path- accessions, the total DS-GSLs content was found to be ogens [1]. Among various substances involved in plant varied between 5.3 and 23.2 mg/g dry weight (DW) with defense, glucosinolates (GSLs), major sulfate-containing an average of 13.0 mg/g DW in the germplasm. Each secondary metabolites, were found in many agricultural individual DS-GSLs component was found in decreasing crops such as cabbage, broccoli, radish, turnip, swede, kale, order of sinigrin (41.7 %) >glucoiberverin (21.7 %) >glu- mustard, cauliflower, watercress, salad rocket, and rapeseed conasturtiin (12.6 %) >glucobarbarin (10.0 %) >glucoi- [27]. GSLs are responsible for diverse physiological effects berin (5.1 %) >glucocheirolin (3.6 %) >glucobrassicanapin such as inhibitors of microbial growth, attractants for par- (2.6 %) >gluconapin (2.1 %), and >glucobrassicin (0.6 %). ticular insects, and as deterrents of different herbivores. Intact GSLs are nontoxic; however, upon tissue damage (e.g., by cutting or chewing), they come into contact with Electronic supplementary material The online version of this myrosinases and are hydrolyzed into unstable aglycones, article (doi:10.1007/s00217-016-2648-6) contains supplementary which rearrange into a range of bioactive products and material, which is available to authorized users. sometimes toxic compounds including isothiocyanates, thi- * Jung Bong Kim ocyanates, nitriles, oxazolidine-2-thiones, or epithioalkanes [email protected] [2]. Although certain GSLs derivatives have anti-nutritional properties [25], it is now well established that methionine- 1 National Institute of Agricultural Sciences, Rural Development Administration, Wanju, Jeollabuk‑do 54875, derived isothiocyanates can offer substantial protection Republic of Korea against cancer [18]. 2 Department of Food and Nutrition, Seoul Women’s The different biological profiles of GSLs are the reason University, Seoul 01797, Republic of Korea why these plant secondary metabolites attract the attention 1 3 1480 Eur Food Res Technol (2016) 242:1479–1484 of several investigators [5, 15]. To date, more than 200 GSL and 181 purple accessions were compared with major veg- structures have been described, although only some of these etables in the Brassicaceae family, such as B. oleracea var. are commonly found within crop plants. In fact, most plants capitata (cabbage), B. rapa ssp. pekinensis (Chinese cab- contain only a limited number of major GSLs (typically bage), Raphanus sativus L. (radish) and B. oleracea var. six or less) with a few others present in trace amounts [7, italic (broccoli). The samples were grown at the National 12, 14]. All GSLs have a common core structure compris- Agro-biodiversity Center, National Academy of Agricul- ing a β-D-thioglucose group linked to a sulfonatedaldoxime tural Science (NAAS), Rural Development Administra- moiety and a variable side chain derived from amino acids. tion (RDA), Republic of Korea in 2012. After harvesting, Generally, they are grouped into aliphatic, aromatic, and the leaves of each accession were ground finely with liquid indole GSLs depending on whether they are originated from nitrogen for the analyses of GSLs. aliphatic amino acids (methionine, alanine, valine, leucine and isoleucine), aromatic amino acids (tyrosine and pheny- Extraction and desulfation of glucosinolates lalanine), or tryptophan [7, 12]. The structural diversity of GSLs is due to chain elongations of amino acids before the Each powdered sample (0.1 g) was frozen and lyophilized, formation of the glucosinolate core structure and secondary and then they are dissolved by boiling aqueous MeOH modifications of the GSLs side chain (e.g., thiol oxidation, (70 %, 1.5 mL) in a microcentrifuge tube (2.0 mL). This hydroxylation, etc.) and/or the glucose moiety (esterifica- process rendered the hydrolytic enzyme myrosinase which tion) [3]. In this regard, a high-performance liquid chroma- responsible for the hydrolysis of glucosinolates. Then each tography (HPLC) coupled to mass spectrum (MS) has gen- samples was extracted for 5 min in a water bath at 70 °C erally been applied for GSL quantification. and then separated by centrifugation (12,000 rpm, 10 min, Leaf mustard (Brassica juncea var. integrifolia; mustard 4 °C) [7]. This process was repeated for two times to allow green or red giant mustard) is a representative member of the the complete extraction of the residue and the supernatants Cruciferae family and is a major ingredient in Gat-Kimchi obtained from each extraction were combined. The com- (leaf mustard Kimchi), which is known for its unique pun- bined extract was loaded onto a mini-column filled with gent and hot flavor. Kimchi can be classified according to the DEAE-Sephadex A-25, 75 μL of aryl sulfatase was injected raw ingredients and processing methods used and the harvest onto the column, and the GSLs present in the extract were season and location of the raw ingredients. 3-Isothiocyanate- desulfated at room temperature for 16–18 h. Desulfo-glu- 1-propene (allylisothiocyanate; AITC), which is derived cosinolates (DS-GSLs) were then eluted into a microcen- from sinigrin, has been identified as the major volatile com- trifuge tube (2.0 mL) using three aliquots (0.5 mL each) pound contained in this dish. Depending on the processing of distilled water. The eluted extract was concentrated by conditions employed, the AITC content has been shown nitrogen gas and dissolved in distilled water (200 μL) and to decrease during fermentation, while the sinigrin content stored at 20 °C before undergoing HPLC analysis. − increases until the dish has ripened optimally [8, 24]. The antioxidant, cytotoxic, and anti-hypertensive effects of the Identification and quantification of DS‑GSLs by LC– dish were shown to correlate with the GSLs hydrolysis prod- ESI–MS/MS and HPLC uct content in Dolsan leaf mustard juice [33, 34]. Although a number of investigations on GSLs in leaf For the qualitative and quantitative analysis of DS-GSLs, mustard have been reported in recent years, there is an HPLC–MS (Finnigan LCQ Deca XP MAX ion trap mass inadequate qualitative and quantitative analysis of GSLs in spectrometer, Thermo Scientific, USA) with electrospray the germplasms of Korean leaf mustard (Brassica juncea ionization detection was carried out using an Inertsil var. integrifolia). Thus, this study intended to analyze of ODS-3 reversed phase column (2.1 150 mm I.D., 5 μm; × GSLs from the germplasm of Korean leaf mustard using a GL Sciences, Japan), at a flow rate of 0.2 mL/min and a high-performance liquid chromatography with electrospray detection wavelength of 227 nm with a column tempera- ionization coupled with a positive-mode ion trap tandem ture of 35 °C. The mobile phases used were 1 % formic mass spectrometry (LC–ESI–MS/MS). acid in water (phase A) and 0.1 % formic acid in 20 % ace- tonitrile (phase B), and the pretreated sample was analyzed using the following elution conditions: gradient elution Materials and methods from 10 to 90 % phase B over 23 min, isocratic elution at 90 % phase B for 9 min, gradient elution from 90 to 10 % Materials phase B over 3 min, and finally re-equilibration of the col- umn with 10 % phase B for 5 min. MS/MS analysis was A total of 210 accessions of Korean leaf mustard (Bras- conducted in a positive ionization mode using electrospray sica juncea var. integrifolia) included 29 green accessions ionization (ESI) source with the following MS parameters: 1 3 Eur Food Res Technol (2016) 242:1479–1484 1481 Fig. 1 Mass spectra and interpretation of unknown DS-GSLs in or 2-hydroxy-2-methylpropyl DS-GSLs: glucoconringin (assigned Korean leaf mustard by LC–ESI–MS/MS and the DS-GSLs LC– unknown compound) [6]; b hydroxy-3,4,5-trimethoxybenzoyl DS- MS library. a 1-Ethyl-2-hydroxyethyl DS-GSLs: glucosisautricin GSLs (presumed unknown compound) [7] cone voltage of 3.5 kV, capillary temperature of 250 °C, revealed that one of the unknown DS-GSLs was found to and desolvation N gas flow rate of 300 L/h. The molecu- have a molecular weight of 311 (m/z 311.65, [M H]+) 2 + lar weight range observed was 50–800 m/z in a full-scan and was potentially assigned as either 1-ethyl-2-hydroxy- mode.
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