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Comparison of the Antioxidant Effects of Quercitrin and Isoquercitrin: Understanding the Role of the 600-OH Group

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Comparison of the Antioxidant Effects of Quercitrin and Isoquercitrin: Understanding the Role of the 600-OH Group molecules Article Comparison of the Antioxidant Effects of Quercitrin and Isoquercitrin: Understanding the Role of the 600-OH Group Xican Li 1,*, Qian Jiang 1, Tingting Wang 1, Jingjing Liu 1 and Dongfeng Chen 2,* 1 School of Chinese Herbal Medicine, Guangzhou University of Chinese Medicine, Waihuan East Road No. 232, Guangzhou Higher Education Mega Center, Guangzhou 510006, China; [email protected] (Q.J.); [email protected] (T.W.); [email protected] (J.L.) 2 School of Basic Medical Science, Guangzhou University of Chinese Medicine, Waihuan East Road No. 232, Guangzhou Higher Education Mega Center, Guangzhou 510006, China * Correspondence: [email protected] or [email protected] (X.L.); [email protected] (D.C.); Tel.: +86-203-935-8076 (X.L.) Academic Editor: Maurizio Battino Received: 6 July 2016; Accepted: 6 September 2016; Published: 19 September 2016 Abstract: The role of the 600-OH (!-OH) group in the antioxidant activity of flavonoid glycosides has been largely overlooked. Herein, we selected quercitrin (quercetin-3-O-rhamnoside) and isoquercitrin (quercetin-3-O-glucoside) as model compounds to investigate the role of the 600-OH group in several antioxidant pathways, including Fe2+-binding, hydrogen-donating (H-donating), and electron-transfer (ET). The results revealed that quercitrin and isoquercitrin both exhibited dose-dependent antioxidant activities. However, isoquercitrin showed higher levels of activity than quercitrin in the Fe2+-binding, ET-based ferric ion reducing antioxidant power, and multi-pathways-based superoxide anion-scavenging assays. In contrast, quercitrin exhibited greater activity than isoquercitrin in an H-donating-based 1,1-diphenyl-2-picrylhydrazyl radical-scavenging assay. Finally, in a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl assay based on an oxidatively damaged mesenchymal stem cell (MSC) model, isoquercitrin performed more effectively as a cytoprotector than quercitrin. Based on these results, we concluded that (1) quercitrin and isoquercitrin can both indirectly (i.e., Fe2+-chelating or Fe2+-binding) and directly participate in the scavenging of reactive oxygen species (ROS) to protect MSCs against ROS-induced oxidative damage; (2) the 600-OH group in isoquercitrin enhanced its ET and Fe2+-chelating abilities and lowered its H-donating abilities via steric hindrance or H-bonding compared with quercitrin; and (3) isoquercitrin exhibited higher ROS scavenging activity than quercitrin, allowing it to improve protect MSCs against ROS-induced oxidative damage. Keywords: quercitrin; isoquercitrin; Q3G; 600-OH; !-OH; flavonoid glycoside; antioxidant mechanisms; mesenchymal stem cells 1. Introduction Flavonoid glycosides can be found in a wide range of plants, especially those used in Chinese herbal medicines, and have been reported to exhibit remarkable antioxidant effects [1]. The glycosyl groups found in flavonoid glycosides are usually hexanoses, which are preferentially condensed in their six-membered (pyranosyl) ring forms. Among these pyranosyl rings, the glucopyranosyl and rhamnopyranosyl systems are regarded as two typical rings [2,3], because of their chemical stability. Flavonoid glucosides and flavonoid rhamnosides are therefore two of the most common members of the flavonoid glycoside family and can be found in a wide range of plants. For example, quercitrin (quercetin-3-O-rhamnoside, Figure1A and Video S1) has been isolated from Molecules 2016, 21, 1246; doi:10.3390/molecules21091246 www.mdpi.com/journal/molecules Molecules 2016, 21, 1246 2 of 11 Molecules 2016, 21, 1246 2 of 11 seven Loranthaceae plants [4], whereas isoquercitrin (quercetin-3-O-glucoside, Q3G, Figure1B and VideobeMolecules widely S2) 2016 has distributed, 21 been, 1246reported in several to Moraceae be widely plants distributed [5]. Furthermore, in several quercitrinMoraceae andplants isoquercitrin [5]. Furthermore, have2 been of 11 quercitrinreported andto co-exist isoquercitrin in several have medicinal been reportedplants, including to co-exist Hypericum in several japonicum medicinal [6], Amomum plants, includingvillosum be widely distributed in several Moraceae plants [5]. Furthermore, quercitrin and isoquercitrin have been Hypericum[7], and Polygonum japonicum [hydropiper6], Amomum [8]. villosum [7], and Polygonum hydropiper [8]. reported to co-exist in several medicinal plants, including Hypericum japonicum [6], Amomum villosum [7], and Polygonum hydropiper [8]. FigureFigure 1. 1.Structures Structures of of quercitrin quercitrin (quercetin-3-(quercetin-3-O-rhamnoside, AA) )and and isoquercitrin isoquercitrin (quercetin-3- (quercetin-3- O-O- glucoside,glucoside, Q3G, Q3G,B ).B). Figure 1. Structures of quercitrin (quercetin-3-O-rhamnoside, A) and isoquercitrin (quercetin-3-O- glucoside,Since stereo Q3G, configurations B). of chiral carbons in the sugar chain do not actually influence the Since stereo configurations of chiral carbons in the sugar chain do not actually influence the antioxidant effects [9], the difference between glucose and rhamnose can be reduced to the ω-OH antioxidantSince effectsstereo configurations [9], the difference of chiral between carbons glucose in the and sugar rhamnose chain do can not be actually reduced influence to the ! the-OH group (more precisely, the ω-O atom) in rhamnopyranosyl. However, when a rhamnopyranosyl or groupantioxidant (more precisely,effects [9], the the! difference-O atom) inbetween rhamnopyranosyl. glucose and rhamnose However, can when be reduced a rhamnopyranosyl to the ω-OH or glucopyranosyl unit is linked to a flavonoid moiety, the ω-position is numbered as C6″. For this reason, glucopyranosylgroup (more precisely, unit is linked the ω-O to atom) a flavonoid in rhamnopyranosyl. moiety, the ! Howe-positionver, iswhen numbered a rhamnopyranosyl as C 00 . For or this the ω-OH group in the rhamnopyranosyl compounds described in this study will be referred6 to as the glucopyranosyl! unit is linked to a flavonoid moiety, the ω-position is numbered as C6″. For this reason, reason,6″-OH the group.-OH As group a ω-functional in the rhamnopyranosyl group in flavonoid compounds glycosides, described the 6″-OH in has this been study largely will neglected be referred the ω-OH00 group in the rhamnopyranosyl! compounds described in this study will00 be referred to as the to asby theresearchers 6 -OH group.with an As interest a -functional in the antioxidant group in activities flavonoid of glycosides,these compounds. the 6 -OHIn fact, has most been of largely the 6″-OH group. As a ω-functional group in flavonoid glycosides, the 6″-OH has been largely neglected neglectedstructure by activity researchers relationship with an studies interest pertaining in the antioxidant to the antioxidant activities effects of these of compounds.these compounds In fact, have most by researchers with an interest in the antioxidant activities of these compounds. In fact, most of the of thefocused structure on the activity A, B, or relationship C rings, with studies very pertaining few reports to on the the antioxidant effects of effectsthe glycosyl of these moiety compounds [10]. structure activity relationship studies pertaining to the antioxidant effects of these compounds have haveFurthermore, focused on there the Ahave, B, been or C norings, reports with concerning very few the reports 6″-OH on group the effects of glycosyl of the units glycosyl until moietynow. [10]. focused on the A, B, or C rings, with very few reports on00 the effects of the glycosyl moiety [10]. Furthermore,Interestingly, there havethe ball-and-stick been no reports models concerning suggested the of 6 quercitrin-OH group and of isoquercitrin glycosyl units that until the 6 now.″-OH Furthermore, there have been no reports concerning the 6″-OH group of glycosyl units until now. groupInterestingly, may be a thechemically ball-and-stick active functional models suggested group. For of example, quercitrin the and O atom isoquercitrin of the 6″-OH that thegroup 600 -OHis Interestingly, the ball-and-stick models suggested of quercitrin and isoquercitrin that the 6″-OH grouphighly may electronegative be a chemically (3.44) active withfunctional two lone pairs group. of electrons. For example, Furthermore, the O atom the of6″ the-OH 6 00group-OH groupat the is group may be a chemically active functional group. For example, the O atom of the 6″-OH group is highlyω-position electronegative of the glycosyl (3.44) ring with appa tworently lone emerges pairs ofout electrons. of the pyranosyl Furthermore, ring (Figure the 2B), 600-OH making group it very at the highly electronegative (3.44) with two lone pairs of electrons. Furthermore, the 6″-OH group at the !-positiondifferent offrom the the glycosyl other three ring apparently-OH groups emerges (at the 2 out″-, 3 of″-, the and pyranosyl 4″-positions) ring attached (Figure2 toB), the making pyranosyl it very ω-position of the glycosyl ring apparently emerges out of the pyranosyl ring (Figure 2B), making it very ring. Lastly, given that the σ bond between C5″ and00 C6″ 00can freely00 rotate (Figure 2B), the 6″-OH group differentdifferent from from the the other other three three -OH -OH groups groups (at (at the the 22″-,-, 33″-, and 4 4″-positions)-positions) attached attached to to the the pyranosyl pyranosyl 00 ring.could Lastly, readily given turn that to theits targetσ bond site between for reaction. C 00 and With C all00 canof this freely in mind, rotate we (Figure imagined2B), the that 6 the-OH 6″-OH group ring. Lastly, given that the σ bond between C5 5″ and C6″ can freely rotate (Figure 2B), the 6″-OH group group could play a number of versatile roles in the antioxidant activity of flavonoid glycosides. 00 couldcould readily readily turn turn to to its its target target site site for for reaction. reaction. With all of this in in mind, mind, we we imagined imagined that that the the 6″ 6-OH-OH groupgroup could could play play a a number number of of versatileversatile roles in in the the antioxidant antioxidant activity activity of offlavonoid flavonoid glycosides. glycosides. Figure 2. Ball-and-stick models of quercitrin (A) and isoquercitrin (B). Figure 2. Ball-and-stick models of quercitrin (A) and isoquercitrin (B).
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