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Cornus Sanguinea L.) Cornus Sanguinea L Turk J Biochem 2017; 42(4): 513–518 Short Communication Zorica Popović*, Jasna Bajić-Ljubičić, Rada Matić and Srdjan Bojović First evidence and quantification of quercetin derivatives in dogberries (Cornus sanguinea L.) Cornus sanguinea L. bir tür kızılcık kuersetin türevlerinin ilk bulgusu ve miktarının DOI 10.1515/tjb-2016-0175 Conclusions: These results indicate that dogberries Received September 30, 2016; accepted April 25, 2017; previously could be a potential source of natural antioxidants, published online June 30, 2017 and encourage further investigation of this species considering that it has not yet been exploited in either Abstract nutrition or as a source of important pharmacological Aim: C. sanguinea L. is a widespread European shrubby compounds. species. It is a potential source of biologically active com- Keywords: Common dogwood; Berry extract; Flavonols; pounds, especially antioxidants, as indicated by the dog- Chemical variability. berries’ black color. The aim of the present study was to determine the content of several quercetin derivatives in the dogberries and to evaluate phytogeographical vari- Özet ability of these compounds. Materials and methods: The dogberries were collected in Amaç: C. sanguinea L, yaygın bir avrupa ağaçsı türüdür. the middle of September at two natural habitats of this Dogberries’in siyah rengiyle belirtilen biyolojik olarak species: Mt. Avala and Lake Zlatar, Serbia. The extract aktif bileşiklerin, özellikle de antioksidanların potan- obtained from fresh fruits was subjected to LC-MS/MS siyel bir kaynağıdır. Bu çalışmanın amacı, dogber- analysis to identify and quantify the content of five querce- ries çeşitli quercetin türevlerinin içeriğini belirle- tin derivatives: quercetin-3-O-glucuronide (Q-3-O-GlcA), mek ve bu bileşiklerin fitocoğrafik değişkenliklerini quercetin-3-O-galactoside (Q-3-O-Gal), quercetin-3-O-ruti- değerlendirmektir. noside (Q-3-O-Rut), quercetin-3-O-glucoside (Q-3-O-Glc) Gereç ve yöntemler: Köpek yavruları, Eylül ortasında bu and quercetin-3-O-rhamnoside (Q-3-O-Rha). türün iki doğal yaşam alanlarında toplandı: Mt. Avala Results: All of examined quercetin derivatives were ve Lake Zlatar, Sırbistan. Yeni meyvelerden elde edilen detected in extract of fresh dogberries and their contents ekstre beş quercetin türevinin içeriğini belirlemek ve were in the following order: Q-3-O-GlcA > Q-3-O-Gal > Q-3- nicelleştirmek için LC-MS/MS analizine tabi tutuldu: O-Rut > Q-3-O-Glc > Q-3-O-Rha. The average amount of quercetin-3-0-glukuronid (Q-3-0-GlcA), quercetin-3-0-ga- Q-3-O- Rut varied significantly and depended on the geo- laktosid (Q-3-O-Gal), kuersetin-3-0-rutinosid (Q-3-0-Rut), graphic origin of the fruit sample. kersetin-3-0-glukozid (Q-3-0-Glc) ve kersetin-3-0- Ramno- sid (Q-3-0-Rha). *Corresponding author: Dr Zorica Popović, Institute for Biological Tartışma: Kontrol edilen tüm quercetin türevleri taze Research, University of Belgrade, Bulevar despota Stefana 142, dogberries ekstraktında tespit edildi ve içerikleri aşağı- 11000 Belgrade, Republic of Serbia, Tel.: +381112078360, daki sırada oldu: Q-3-0-GlcA > Q-3-O-Gal > Q-3-O-Rut > Q-3 Fax: +381112761433, e-mail: [email protected] -O-Glc > Q-3-0-Rha’dır. Ortalama Q-3-O-Rut miktarı, Jasna Bajić-Ljubičić: Faculty of Biology, University of Belgrade, önemli ölçüde değişir ve meyve örneğinin coğrafik köke- Studentski trg 16, 11000 Belgrade, Republic of Serbia Rada Matić and Srdjan Bojović: Institute for Biological Research, nine bağlıdır. University of Belgrade, Bulevar despota Stefana 142, 11000 Sonuç: Bu sonuçlar dogberries’in doğal antioksidanların Belgrade, Republic of Serbia potansiyel bir kaynağı olabileceğini ve beslenmede veya 514 Zorica Popović et al.: First evidence and quantification of quercetin derivatives in dogberries önemli farmakolojik bileşiklerin kaynağı olarak henüz in human health [10]. Quercetin is one of the most kullanılmadığını göz önüne alarak bu türün daha fazla abundant flavonoids present in many fruits and vegeta- araştırılmasını teşvik ettiğini göstermektedir. bles, mainly in the leaves and external tissues of fleshy fruits (epicarp), as aglycones and glycosides. Quercetin Anahtar Kelimeler: Ortak köpek ağacı; çilek özütü; flavo- glycosides contain a sugar group at the 3-position; the noller; kimyasal değişkenlik. most frequently found sugar is glucose, followed by galactose and rhamnose [11]. Phytochemical characterization of the members of Introduction the genus Cornus has been mainly based on the relative distribution of total polyphenols [12], anthocyanins [13], Cornus sanguinea L. (Cornaceae) is a fleshy-fruited shrub, flavonoids [14], iridoids [15] and carboxylic acids [16]. In 1–5 m in height, with a growth form similar to a small tree. addition to the phytochemical studies of certain species of It is widely distributed in the temperate regions of Europe, the genus Cornus, data on the biological activities of fruit from the Mediterranean basin to England; it occurs on and leaf extracts, their antioxidant and cytotoxic proper- base-rich soils, in plentiful light conditions and prefers ties have been reported [17]. the temperature regime and soil moisture of a continen- Since the focus of phytochemical and pharmaco- tal climate [1]. The blooming period is from May to June; logical research has been directed toward species with the plant is insect-pollinated. Immature fruits are red, and edible fruits, data about the biologically active com- when fully ripened, black; fruit ripening usually occurs in pounds in C. sanguinea are scarce. In several previous September. Leaves are rich in total phenolics and tannins studies, an antioxidative activity of the leaves’ and [2] and the fruit pulp is rich in lipids (24.9%); it has rela- fruits’ extracts has been reported [18, 19]. This study tively high protein content (6.4%), and the fiber fraction aimed to determine and quantify certain natural anti- and soluble carbohydrates account for 10.3% and 53.8%, oxidants in dogberries. respectively [3]. Cornus sanguinea berries are not toxic, but their tart flavor makes them unpalatable in the raw form. This flavor can be improved by cooking, and so the Materials and methods plant could be potentially palatable, especially con- sidering its seeds are rich in proteins and oils. Cooking Chemicals and reagents decreases tannin content; if the sugar added, the sugar/ acid radio increases, which both contribute to better All chemicals, including standards of phenolic com- taste of tart berries [4]. Dogwood is used in the treat- pounds, were purchased from Sigma-Aldrich Chem ment of malaria, as it is rich in bitter alkaloids [5]. It is (Steinheim, Germany), Fluka Chemie GmbH (Buchs, Swit- also part of homeopathic and naturopathic medicines, zerland) or from ChromaDex (Santa Ana, USA), and were indicated for mainly transitory syndromes of numerous of analytical grade. subacute inflammatory and necrotic ailments. Ethnop- harmacological importance of C. sanguinea berries is documented by several studies, i.e. for their nutraceuti- Plant material cal properties [6], as a remedy for diarrhea and stom- achaches [7] and for treatment of sore eyes, throat and Plant material was collected in September 2015, at two gastrointestinal disorders [8]. localities: Mt. Avala (44°41′25″ N, 20° 30ʹ 51″ E; 440 m Fleshy-fruited plants, namely berries, are rich in a.s.l.) and Lake Zlatar (43° 30′ 31″ N, 19° 50′ 19″ E; 900 m phytochemicals with antioxidant properties, and many a.s.l.). Each population was represented with 10 plants of their health-beneficial effects are attributed to their (Mt. Avala, n = 10 and Lake Zlatar, n = 10). Fully mature high content of polyphenolic compounds, especially fruits were dark-purple, almost black and easily detach- flavonoids [9]. Flavonols, a class of flavonoids, and able from the stem. From each tree, five berries were col- especially glycosides of quercetin and kaempferol, lected (pooled sample). Fresh berries were refrigerated exhibit strong free-radical scavenging activity and immediately after harvesting and over the night until protect plant cell metabolism from oxidative damage; further use. Samples of branches, leaves and fruits have they protect animal cell metabolism from oxidative been deposited in the Institute for Biological Research, damage and consequently may have an important role Belgrade. Zorica Popović et al.: First evidence and quantification of quercetin derivatives in dogberries 515 Extract preparations were extracted with 5 mL of methanol 70% (20 h of shaking at 150 rpm/min, at 20°C). Then the extracts were filtered For the determination of five quercetin derivatives: querce- through membrane filter (0.45 μm) and used for analysis. tin-3-O-glucuronide (Q-3-O-GlcA), quercetin-3-O-galac- toside (Q-3-O-Gal), quercetin-3-O-rutinoside (Q-3-O-Rut), quercetin-3-O-glucoside (Q-3-O-Glc) and quercetin-3-O- LC-MS/MS analysis of selected flavonols rhamnoside (Q-3-O-Rha), a methanol extract prepared from the crushed fruits of C. sanguinea was used. Extract was Determination of the selected compounds in the extracts obtained by diluting the plant material in methanol 70% of dogberries was conducted according to the Orčić (v/v) at a ratio 1:10; 0.5 g of fresh berries (without seeds) et al. [20], using Agilent Technologies 1200 Series HPLC Table 1: Optimized dynamic MRM parameters. Compound Precursor m/z Product m/z Vfragmentor (Vf) Vcollision (Vc) tR Quercetin-3-O-glucuronide 477 300 145 20 1.97 Quercetin-3-O-galactoside 463 300 200 30 2.03 Quercetin-3-O-rutinoside 609 300 135 42 2.06 Quercetin-3-O-glucoside 463 300 210 30 2.11 Quercetin-3-O-rhamnoside 447 300 190 27 2.61 Precursor ion; Product ion; Vfragmentor, fragmentor voltage (cone voltage); Vcollision, collision voltage; tR, retention time. 4 x104 –ESI MRM frag=145.0V [email protected] (477.0000 -> 300.0000) kal_02500_l.d x10 –ESI MRM frag=145.0V [email protected] (477.0000 -> 300.0000) 048_20x_l.d 2.4 AB2.4 2.2 2.2 2 2 1.8 1.8 4 5 1.6 4 1.6 2 1.4 1.4 2 1.2 1.2 1 1 3 0.8 0.8 0.6 0.6 1 1 0.4 0.4 3 0.2 0.2 5 3.01 3.01 0 0 2.4 2.5 2.6 2.7 2.8 2.933.1 3.2 3.3 3.4 3.5 3.6 3.7 3.8 3.9 4 4.1 2.42.5 2.62.7 2.82.9 33.1 3.233.3 .4 3.53.6 3.73.8 3.944.1 Counts vs.
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