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Research Article Identification of Six Flavonoids As Novel Cellular Antioxidants and Their Structure-Activity Relationship

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Research Article Identification of Six Flavonoids As Novel Cellular Antioxidants and Their Structure-Activity Relationship Hindawi Oxidative Medicine and Cellular Longevity Volume 2020, Article ID 4150897, 12 pages https://doi.org/10.1155/2020/4150897 Research Article Identification of Six Flavonoids as Novel Cellular Antioxidants and Their Structure-Activity Relationship Qiang Zhang , Wenbo Yang, Jiechao Liu, Hui Liu, Zhenzhen Lv, Chunling Zhang, Dalei Chen, and Zhonggao Jiao Zhengzhou Fruit Research Institute, Chinese Academy of Agricultural Sciences, Zhengzhou, 450009 Henan, China Correspondence should be addressed to Zhonggao Jiao; [email protected] Received 27 May 2020; Revised 5 August 2020; Accepted 7 September 2020; Published 21 September 2020 Academic Editor: Lillian Barros Copyright © 2020 Qiang Zhang et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. This study is aimed at determining the relationship of flavonoid structures to their chemical and intracellular antioxidant activities. The antioxidant activities of 60 flavonoids were investigated by three different antioxidant assays, including 2,2-diphenyl-1- picrylhydrazyl (DPPH) radical scavenging activity, oxygen radical absorption capacity (ORAC), and cellular antioxidant activity (CAA) assays. The result showed 6 flavonoids as good cellular antioxidants evaluated for the first time. The cellular antioxidant activities of compounds 7-methoxy-quercetin, 3-O-methylquercetin, 8-hydroxy-kaempferol, quercetin-3-O-α-arabinofuranose, kaempferol-7-O-glucopyranoside, and luteolin6-C-glucoside were linked with the upregulation of antioxidant enzyme activities (superoxide dismutase, catalase, and glutathione peroxidase). A structure-activity relationship suggested that 2,3-double bond, 4-keto groups, 3′,4′-catechol structure, and 3-hydroxyl in the flavonoid skeleton played important roles in the antioxidant behavior. Furthermore, the cell proliferative assay revealed a low cytotoxicity for 3-O-methylquercetin. The present results provide valuable information for the dietary application of flavonoids with different structures for high antioxidant. 1. Introduction flavonoids in prevention and relieve various diseases such as obesity, diabetes, cancer, angiocardiopathy, and heart The reactive oxygen species (ROS) are known to damage the diseases [5–7]. Therefore, the flavonoids were considered to tissues of the body, which leads to disturb the established be candidates for these disease management due to the ROS order on the body system. The ROS attacked biomolecules and iNOS caused [8]. The capacity of flavonoids depends like DNA, lipids, and proteins to free radical damage, which on their substituent groups, the number of hydroxyl groups, stimulated the development of many diseases, such senility, other substitutions, and conjugations. In addition, quercetin, angiocardiopathy, and cancer [1]. At present, researchers kaempferol, rutin, hesperidin, naringin, genistein, phloretin, have found that flavonoid consumption can improve cancer isoquercitrin, taxifolin, epicatechin, cyanidin chloride, and and cardiovascular diseases [2]. There are inverse relation- their derivatives were widely distributed in apples, blue- ship between dietary flavonoids and chronic diseases, which berries, cherries, grapes, tea, citrus, peppers, red wine, choco- displayed the importance of studying flavonoids [3]. late, etc., which has extensive biological activity [9–11]. Flavonoids is one of the most abundant phenolic com- However, to our knowledge, systematic studies on differences pounds in various fruits, vegetables, grains, spices, beverages, in the antioxidant ability of various flavonoids and the and medicinal plants, which are structured by a C6-C3-C6 structure-activity relationships are still scarce. In particular, skeleton labeled with the rings A, B, and C (Table 1). The the influence between different structural flavonoids and subclasses included flavones, flavonols, flavanones, flavanols, the antioxidant enzyme activities (superoxide dismutase anthocyanidins, and isoflavonoids [4]. Many researchers (SOD), catalase (CAT), and glutathione peroxidase (GSH- have discovered a wide range of biological activities of the Px)) has rarely been studied. 2 Oxidative Medicine and Cellular Longevity Table 1: The chemical structures of 60 flavonoids. No Flavonoids Core structure Substructure Flavone R=H ′ ′ 1 Isorhamnetin R3,R5,R7,R4 =OH, R5 =OCH3 ′ ′ 2 Rhamnetin R3,R5,R4 ,R5 =OH, R7=OCH3 ′ 3 Kaempferide R3,R5,R7=OH, R4 =OCH3 ′ ′ 4 Morin R3,R5,R7,R4 ,R6 =OH ′ ′ 53-O-methylquercetin R3= OCH3, R5,R7,R4 ,R6 =OH ′ 6 Kaempferol R3,R5,R7,R4 =OH ′ ′ 7 Quercetin R3,R5,R7,R4 ,R5 =OH ′ 8 Herbacetin R3,R5,R7,R8,R4 =OH ′ ′ ′ 9 Myricitrin R3=Orha, R5,R7,R3 ,R4 ,R5 =OH ′ ′ 10 Avicularin R3=Oara, R5,R7,R3 , R4 =OH ′ 11 Trifolin R3=Oglc, R5,R7,R3 =OH ′ ′ 12 Kaempferol-4 -O-glucopyranoside R3,R5,R7=OH, R4 =Oglc ′ 13 Kaempferol-7-O-glucopyranoside R3,R5=OH, R7=Oglc, R4 =OH ′ 14 Kaempferol-3-O-arabinoside R3=Oara, R5,R7,R3 =OH ′ ′ 15 Isorhamnetin-3-O-glucopyranoside R3=Oglc, R5,R7,R3 =OH, R4 =OCH3 ′ ′ 16 Rutin R3=Orha, R5,R7,R4 ,R5 =OH ′ 17 Spiraeoside 3 R ,R,R,R ′=OH, R =Oglc 2′ 4′ 3 5 7 5 4 18 Myricetin 8 B R ,R,R,R ′,R ′,R ′=OH O 2 5′ 3 5 7 3 4 5 7 1′ 6′ ′ 19 Tangeretin A C R5,R6,R7,R8,R4 =OCH3 6 3 20 Chrysin 5 4 R5,R7=OH O 21 Baicalein R5,R6,R7=OH ′ 22 Apigenin R5,R7,R4 =OH ′ ′ 23 Luteolin R5,R7,R3 ,R4 =OH ′ ′ 24 Cynaroside R7=Oglc, R3 ,R4 =OH ′ ′ ′ 25 Myricetin-3-O-galactoside R3=Ogal, R5,R7,R3 ,R4 ,R5 =OH ′ ′′ 26 Quercetin-3-O-galactoside R3=Ogal, R5,R7,R3 ,R4 =OH ′ ′ 27 Quercetin-3-O-rhamnoside R3,R5=OH, R7=Orha, R3 ,R4 =OH ′ ′ 28 Quercitrin R3=Orha, R5,R7,R3 ,R4 =OH ′ ′ 29 Isoquercitrin R3=Oglc, R5,R7,R3 ,R4 =OH ′ 30 Vitexin R5=Cglc, R6,R8,R4 =OH ′ ′ 31 Orientin R8=Cglc, R5,R7,R3 ,R4 =OH ′ ′ 32 Isoorientin R4=Cglc, R5,R7,R3 ,R4 =OH ′ 33 Isovitexin R5,R7,R4 =OH, R6=Cglc 34 Galangin R3,R5,R7=OH ′ ′ 35 Fisetin R3,R7,R3 ,R4 =OH ′ ′ 36 Diosmetin R5,R7,R3 =OH, R4 =OCH3 Genkwanin R ,R ′=OH, R =OCH 37 5 4 7 3 flavanones R=H 3′ ′ ′ ′ 38 Dihydromyricetin R3,R5,R7,R3 ,R4 ,R5 =OH 2′ ′ 4 ′ ′ 39 Taxifolin 8 B R3,R5,R7,R4 ,R5 =OH O 2 5′ 7 40 Dihydromorin 1′ ′ ′ A C 6 R3,R5,R7,R4 =OH 41 Neohesperidin 6 3 R ,R ′=OH, R =Oglcgla, R ′=OCH 5 4 5 3 7 5 3 O ′ 42 Narirutin R7=Oglcgla, R4 =OH Oxidative Medicine and Cellular Longevity 3 Table 1: Continued. No Flavonoids Core structure Substructure ′ ′ 43 Hesperetin R5,R7,R4 =OH, R5 =OCH3 ′ ′ 44 Hesperidin R5,R5 =OH, R7=Oglcgla, R4 =OCH3 ′ 45 Naringenin R5,R7,R4 =OH ′ 46 Liquiritigenin R7,R4 =OH Chalcone 3′ R=H 2′ 4′ 47 Neohesperidin dihydrochalcone ′ ′ ′ 4 B R3,R3 ,R6 =OH, R4 =Oglcgla 5′ 315 ′ ′ 48 Phloretin 6′ R1, R3,R5,R4 =OH A 6 2 ′ 49 Phlorizin R1,R3,R4 =OH, R5=Oglc 1 O ′ 50 Isoliquiritigenin R1,R3,R4 =OH Anthocyanidin R=H R 51 Cyanidin chloride 1 R1=OH 52 Delphinidin chloride2′ OH R2,R3=OH 8 B 53 Cyanin chloride HO O+ R1=OH, R2=H, R3,R4=Oglc R 54 Cyanidin-3-O-glucoside chloride A C 2 R1=OH, R2=H, R3=Oglc 6 55 Pelargonin chlorideR3 R1,R2=H, R3,R4=Oglc R 56 Oenin chloride 4 R1,R2=OCH3,R3=Oglc 57 Malvin R1,R2=OCH3,R3,R4=Oglc Flavans 3′ R=H 2′ 4′ 58 Epicatechin ′ ′ 8 B R3,R5,R7,R4 ,R5 =OH O 2 5′ 7 59 Catechin 1′ ′ R ,R,R,R ′,R ′=OH A C 6 3 5 7 4 5 6 3 4 ′ ′ ′ 60 Epigallocatechin gallate 5 R3=gallic acid, R5,R7,R3 ,R4 ,R5 =OH Orha: -O-α-L-rhamnopyranoside; Oara: -O-α-L-arabinofuranoside; Oglc: -O-glucopyranoside; Ogal: -O-β-L-galactopyranoside; Cglc: -C-glucopyranoside; Oglcgla: -O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside. The values having no letters in common are significantly different (P <0:05). R is the number in core structure. Therefore, we have chosen 60 flavonoids, which have the sodium salt, 2′,7′-dichlorfluorescin diacetate (DCFH–DA), diversity of their core structures and substitution patterns, and 2,2-azobis (2-amidinopropane) dihydrochloride solu- which contribute to systematic studies on the differences in tion (ABAP) were purchased from Sigma Chemical Co. chemical and cell-based antioxidant assays in this work. (Sigma-Aldrich, St. Louis, MO, USA). Flavonoid standards The antioxidant activities of a series of flavonoids (Table 1) were purchased from Solarbio Science & Technology Co., which are commonly found in diet, including flavones, flavo- Ltd. (Beijing, China). Phosphate buffer (PBS), MEM/EBSS, nols, flavanones, flavanols, flavanes, chalcones, and antho- foetal bovine serum (FBS), penicillin, and streptomycin were cyanidins, were examined by 2,2-diphenyl-1-picrylhydrazyl purchased from HyClone (Logan, UT, USA). Cell Counting radical scavenging activity, oxygen radical absorption capac- Kit-8 was obtained from Dojindo China Co., Ltd. (Shanghai, ity, and cellular antioxidant activity assays. The structure- China). Kits for the determination of superoxide dismutase activity relationship of different structures of dietary flavo- (SOD), glutathione peroxidase (GSH-Px), and catalase noids was analyzed for obtaining the substructures with high (CAT) were purchased from Beyotime Biotechnology antioxidant activity. The cellular antioxidant activity assay (Shanghai, China). was closer to physiological conditions for giving an extensive evaluation of the antioxidant. Moreover, the cytotoxicity and 2.2. Oxygen Radical Antioxidant Capacity (ORAC) Assay. antiproliferative activity assays were also measured. This The ORAC assay was evaluated as previously described by study has provided the theoretical foundation for the struc- Cao et al. with some modifications [12, 13]. 50 μL of samples tural modification of flavonoids as effective antioxidant. or Trolox with different concentrations and the fluorescein solution was added to a 96-well microplate, which was incu- bated at 37°C for 10 min.
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