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LC-MS/MS Screening of Phenolic Compounds in Wild and Cultivated Grapes Vitis Amurensis Rupr

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molecules Article LC-MS/MS Screening of Phenolic Compounds in Wild and Cultivated Grapes Vitis amurensis Rupr. Mayya Razgonova 1,2,* , Alexander Zakharenko 1,3, Konstantin Pikula 1 , Yury Manakov 3, Sezai Ercisli 4 , Irina Derbush 1, Evgeniy Kislin 1, Ivan Seryodkin 5, Andrey Sabitov 1, Tatiana Kalenik 2 and Kirill Golokhvast 1,2,3,5 1 N.I. Vavilov All-Russian Institute of Plant Genetic Resources, B. Morskaya 42-44, 190000 Saint-Petersburg, Russia; [email protected] (A.Z.); [email protected] (K.P.); [email protected] (I.D.); [email protected] (E.K.); [email protected] (A.S.); [email protected] (K.G.) 2 Far Eastern Federal University, 10 Ajax Bay, Russky Island, 690922 Vladivostok, Russia; [email protected] 3 Siberian Federal Scientific Centre of Agrobiotechnology, Centralnaya, Presidium, 633501 Krasnoobsk, Russia; [email protected] 4 Department of Horticulture, Agricultural Faculty, Ataturk University, 25240 Erzurum, Turkey; [email protected] 5 Pacific Geographical Institute, Far Eastern Branch of the Russian Academy of Sciences, Radio 7, 690041 Vladivostok, Russia; [email protected] * Correspondence: [email protected] Abstract: This work represents a comparative metabolomic study of extracts of wild grapes obtained from six different places in the Primorsky and Khabarovsk territories (Far East Russia) and extracts of Citation: Razgonova, M.; grapes obtained from the collection of N.I. Vavilov All-Russian Institute of Plant Genetic Resources Zakharenko, A.; Pikula, K.; Manakov, Y.; Ercisli, S.; Derbush, I.; Kislin, E.; (St. Petersburg). The metabolome analysis was performed by liquid chromatography in combination Seryodkin, I.; Sabitov, A.; Kalenik, T.; with ion trap mass spectrometry. The results showed the presence of 118 compounds in ethanolic et al. LC-MS/MS Screening of extracts of V. amurensis grapes. In addition, several metabolites were newly annotated in V. amurensis. Phenolic Compounds in Wild and The highest diversity of phenolic compounds was identified in the samples of the V. amurensis grape Cultivated Grapes Vitis amurensis collected in the vicinity of Vyazemsky (Khabarovsk Territory) and the floodplain of the Arsenyevka Rupr.. Molecules 2021, 26, 3650. River (Primorsky Territory), compared to the other wild samples and cultural grapes obtained in the https://doi.org/10.3390/ collection of N.I. Vavilov All-Russian Institute of Plant Genetic Resources. molecules26123650 Keywords: Amur grape; identification; mass spectrometry; metabolites; metabolomics Academic Editor: Eulogio J. Llorent-Martínez Received: 17 May 2021 1. Introduction Accepted: 14 June 2021 Published: 15 June 2021 The appearance of the first representatives of the Vitaceae family (genus Vitis) dates from the Upper Cretaceous period [1]. Several types of fossil grapes of genus Vitis have Publisher’s Note: MDPI stays neutral been found in different parts of North America [2]. In the Eocene, representatives of the with regard to jurisdictional claims in genus Vitis were widespread in Eurasia and the Far North [2]. In the Paleogene, one of the published maps and institutional affil- best-preserved species of fossil grapes Vitis sachalinensis Krysht. was found and described iations. in the sediments of the Sakhalin Island, the Russian Far East. These data show that the evolution of the vine in the territory of Russia proceeded from ancient times. Moreover, now wild grapes of the genus Vitis grow in many Russian regions [3,4]. At the same time, there is very little information about the culture of East Asian grapes. Copyright: © 2021 by the authors. Grape berries contain 65–85% water; 10–33% sugar (glucose and fructose); flofaben; Licensee MDPI, Basel, Switzerland. gallic acid; quercetin; oenin; the glycosides monodelphinidin and delphinidin; the acids This article is an open access article malic, hydrosilicic, ortho-hydroxybenzoic, phosphoric, tartaric, citric, succinic, formic, distributed under the terms and pectin, and tannins; salts of potassium; magnesium; calcium; manganese; cobalt; iron conditions of the Creative Commons vitamins B1, B2, B6, B12, A, C, P, and PP; folic acid; and enzymes. The dominant class Attribution (CC BY) license (https:// of biologically active compounds of fruits and especially grape ridges are flavonoids, in creativecommons.org/licenses/by/ particular complexes of oligomeric proanthocyanidins (condensed tannins), which are 4.0/). Molecules 2021, 26, 3650. https://doi.org/10.3390/molecules26123650 https://www.mdpi.com/journal/molecules Molecules 2021, 26, 3650 2 of 17 polymeric forms of flavonoids from the group of catechins, and their monomeric units, namely catechins and leuсoanthocyanidins [5]. Many studies have been devoted to the biological activity of flavonoids and complexes of oligomeric proanthocyanidins [6,7]. Complexes of oligomeric proanthocyanidins act as traps of free radicals and block the process of lipid peroxidation of biological mem- branes [8,9]. Their antioxidant activity is many times higher than that of vitamins E and C. They can inhibit the activity of many enzymes (hydrolase, oxidoreductase, kinase, trans- ferase, among others) [10]. Due to the wide spectrum of action, the active compounds of the grapes V. amurensis have a pronounced positive effect on various organs and systems of the body, such as antihypertensive and vasostrengthening effects, as well as antidiabetic, anti- inflammatory, antiallergy, anticarcinogenic, antistress, radioprotective, and antirheumatic effects. Moreover, flavonoids have an anti-Alzheimer’s activity [11–13]. This work presents a detailed comparative study of the metabolomic composition of wild V. amurensis grape berry extracts taken from six different locations of the Russian Far East and four cultural specimens of V. amurensis obtained from the collection of N.I. Vavilov All-Russian Institute of Plant Genetic Resources (St. Petersburg). High-performance liquid chromatography (HPLC) in combination with tandem mass spectrometry was used to identify target analytes in the extracts. Previously, the authors carried out metabolomic studies of Far Eastern plant species, such as Schizandra chinensis, Rhodiola rosea, Rhododendron adamsii, and Panax ginseng [14,15]. 2. Results The metabolome of ten samples of wild and cultural V. amurensis was analyzed and compared. A combination of both ionization modes (positive and negative) in MS full scan mode was applied for the molecular mass determination of the compounds in ethanolic ex- tracts of V. amurensis. Compound identification was performed by comparing the observed m/z values and the fragmentation patterns with the literature. The list of compounds identified in the ethanolic extract of V. amurensis are represented in Table A1. The 118 com- pounds shown in Table A1 belong to different phenolic families, namely anthocyanidins, flavones, flavonols, flavan-3-ols, flavanones, hydroxycinnamic acids, hydroxybenzoic acids, stilbenes, and tannins. 2.1. Anthocyanidins and Anthocyanins A total of 18 anthocyanin compounds have been identified in the analyzed samples of V. amurensis (Table1). The anthocyanins pelargonidin-3- O-glucoside, cyanidin-3-O- glucoside, and petunidin-3-(6-O-coumaroyl) glucoside have already been characterized as a component of Far East V. amurensis [16]. The anthocyanins malvidin-3-O-acetylhexoside, delphinid-3,5-O-diglucoside, malvidin-3-O-rutinoside, malvidin 3-acetyl-5-glucoside, petu- nidin 3-coumaroylglucoside-5-O-glucoside, and malvidin 3-coumaroylglucoside-5-O- glucoside were only found in the extracts of cultivated V. amurensis (St. Petersburg). Molecules 2021, 26, 3650 3 of 17 Table 1. Anthocyanins identified in the ethanolic extracts of V. amurensis. No. Identified Compound ARS ART KAL PAK RIK VZK SPB-1 SPB-2 SPB-3 SPB-4 Cyanidin 1. + + + + + 3,5-O-diglucoside Cyanidin-3-O-glucoside 2. [Cyanidin + 3-O-beta-D-glucoside] Delphinidin 3. + + 3-O-glucoside Delphinidin-3,5-O- 4. + diglucoside Malvidin 3-(6-O-acetyl) 5. + + + glucoside Malvidin 6. 3-(6-O-coumaroyl) + + glucoside Malvidin 7. + + + + + + 3-(6’-p-caffeoylglucoside) 8. Malvidin 3,5-diglucoside + + + + + + + + Malvidin 9. 3-coumaroylglucoside-5- + O-glucoside Malvidin 3-O-acetyl 10. + hexoside 11. Malvidin 3-O-glucoside + + + + + + + + Pelargonidin-3-O- 12. glucoside + (callistephin) Peonidin-3,5-О- diglucoside [peonin; 13. + + + + + + peonidin 3-glucoside-5-glucoside] 14. Peonidin-3-O-glucoside + + + Petunidin 15. 3-(6-O-coumaroyl) + glucoside Petunidin 16. 3-coumaroylglucoside-5- + O-glucoside Petunidin 3-O-glucoside- 5-O-glucoside [Petunidin 17. + + + + + 3,5-di-O-beta-D- glucoside] 18. Petunidin-3-O-glucoside + Total number 2 10 5 1 3 8 7 8 6 6 ARS, wild V. amurensis sample obtained from floodplain of the Arsenyevka River (Primorsky Territory); ART, wild V. amurensis sample obtained from the vicinity of Artem (Primorsky Territory); KAL, wild V. amurensis sample obtained from the vicinity of Kalinovka (Primorsky Territory); PAK, wild V. amurensis sample obtained from the Pakhtusov Islands (Sea of Japan); RIK, wild V. amurensis sample obtained from Rikord Island (Sea of Japan); VZK, wild V. amurensis sample obtained from the vicinity of Vyazemsky (Khabarovsk Territory); SPB-1, SPB-2, SPB-3, and SPB-4, samples of cultivated V. amurensis provided by N.I. Vavilov All-Russian Institute of Plant Genetic Resources (St. Petersburg). 2.2. Other Flavonoid Compounds A total of 42 flavonoid compounds were identified in analyzed V. amurensis samples (Table2). The flavonols dihydrokaempferol, kaempferide, mearnsetin, kaempferol-3- O-glucoside, dihydrokaempferol
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  • Changes in Phenolic Compounds and Antioxidant Activity of Fruit Musts and Fruit Wines During Simulated Digestion

    Changes in Phenolic Compounds and Antioxidant Activity of Fruit Musts and Fruit Wines During Simulated Digestion

    molecules Article Changes in Phenolic Compounds and Antioxidant Activity of Fruit Musts and Fruit Wines during Simulated Digestion Tomasz Tarko * , Aleksandra Duda-Chodak and Agata Soszka Department of Fermentation Technology and Microbiology, Faculty of Food Technology, University of Agriculture in Krakow, ul. Balicka 122, 30-149 Krakow, Poland; [email protected] (A.D.-C.); [email protected] (A.S.) * Correspondence: [email protected]; Tel.: +48-12-6624792 Academic Editor: Urszula Gawlik-Dziki Received: 5 November 2020; Accepted: 24 November 2020; Published: 27 November 2020 Abstract: The content of polyphenols (total phenolic content (TPC)) and the antioxidant activity (AOX) of food products depend on the raw materials used and the technological processes in operation, but transformations of these compounds in the digestive tract are very important. The aim of this study was to determine the TPC, profile of polyphenols, and AOX of apple and blackcurrant musts and wines in order to evaluate the changes occurring in a simulated human digestive system. The research material consisted of apples and blackcurrant, from which musts and fruit wines were obtained. All samples were subjected to three-stage digestion in a simulated human digestive system and then analyzed for the following: TPC (Folin–Ciocalteu method) and profile (HPLC), AOX (method with 2,20-azino-bis (3-ethylbenzothiazoline-6-sulfonic) acid (ABTS) radical), and for the wines also total extract, volatile acidity (International Organization of Vine and Wine (OIV) method), and sugar profile (HPLC). The antioxidant activity of fruit wines is directly related to the total polyphenol content. Phenolic compounds were transformed during all digestive stages, which led to the formation of compounds with higher antioxidant capacity.
  • Quality Assesment of Urtica Dioica L. Samples Collected from Different Locations of Turkey

    Quality Assesment of Urtica Dioica L. Samples Collected from Different Locations of Turkey

    Turk J Pharm Sci 11(2), 223-230, 2014 Short communication Quality Assesment of Urtica dioica L. Samples Collected from Different Locations of Turkey Sanem HO§BA§, Mustafa ASLAN*, Ekrem SEZİK Gazi University, Faculty of Pharmacy, Department of Pharmacognosy, 06330 Ankara, TURKEY Urtica dioica L. (Urticacea) is widely distributed throughout the temperate regions of the world. Leaves of the plant recommended not only for the complaints associated with rheumatoid arthritis, cardiovascular diseases and diabetes but also have antiviral, antioxidant, anti-inflammatory activities. It is also used as traditional medicine as panacea in Turkey. Despite, U. dioica leaf is monographed in European Pharmacopeia as “Nettle Leaf - Urtica folium” and standardized by liquid chromatography for its chlorogenic acid content; aerial parts of plants are sold instead of leaves at the herbal shops for medical purposes in Turkey. The objective of our study is to determine quality of samples and compare the chlorogenic acid amount in aerial parts and leaves collected from different localities of Anatolia. Extraction procedure was employed according to European Pharmacopeia 6.0. /?-Coumaric acid was used as internal standart. RP-HPLC was performed in order to determine chlorogenic acid amounts. The leaf samples collected from Düzce, Maraş, Isik Mountain and Palandöken Mountain has possesed highest chlorogenic acid amounts 1.91±0.0003%, 1.156±0.0019%, 0.67±0.00068%, 0.63±0.0024% respectively. However amount of chlorogenic acid in aerial parts of same samples has been found 1.047±0.0007%, 0.751±0.0033%, 0.31±0.0085%, 0.488±0.0051% respectively. Results indicate that in all samples, chlorogenic acid content has been found higher in leaves than aerial parts.