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Stability of Anthocyanins and Their Degradation Products from Cabernet Sauvignon Red Wine Under Gastrointestinal Ph and Temperature Conditions

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Stability of Anthocyanins and Their Degradation Products from Cabernet Sauvignon Red Wine Under Gastrointestinal Ph and Temperature Conditions molecules Article Stability of Anthocyanins and Their Degradation Products from Cabernet Sauvignon Red Wine under Gastrointestinal pH and Temperature Conditions Ping Yang 1,†, Chunlong Yuan 1,2,3,†, Hua Wang 1,2,3,*, Fuliang Han 1,2,3,*, Yangjie Liu 1, Lin Wang 1 and Yang Liu 1 1 College of Enology, Northwest A&F University, Yangling 712100, China; [email protected] (P.Y.); [email protected] (C.Y.); [email protected] (Y.L.); [email protected] (L.W.); [email protected] (Y.L.) 2 Shaanxi Engineering Research Center for Viti-Viniculture, Northwest A&F University, Yangling 712100, China 3 Heyang Viticulture Experimental Station, Northwest A&F University, Heyang 715300, China * Correspondence: [email protected] (H.W.); hanfl@nwsuaf.edu.cn (F.H.); Tel.: +86-29-8709-2107 (H.W. & F.H.) † These authors contributed equally to this work. Received: 14 January 2018; Accepted: 5 February 2018; Published: 7 February 2018 Abstract: This study investigated the stability of wine anthocyanins under simulated gastrointestinal pH and temperature conditions, and further studied the evolution of anthocyanin degradation products through simulated digestive conditions. The aim of this study was to investigate the relation between anthocyanins’ structure and their digestive stability. Results showed that a total of 22 anthocyanins were identified in wine and most of these anthocyanins remained stable under simulated gastric digestion process. However, a dramatic concentration decrease happened to these anthocyanins during simulated intestinal digestion. The stability of anthocyanins in digestive process appeared to be related to their structure. The methoxy group in the B-ring enhanced the stability of anthocyanins, whereas hydroxyl group resulted in a reduction of their stability. Acylation decreased the stability of malvidin 3-O-glucoside. Pyruvic acid conjugation enhanced the structural stability of pyranoanthocyanins, whereas acetaldehyde attachment weakened their stability. A commercial malvidin 3-O-glucoside standard was used to investigate anthocyanin degradation products under simulated digestion process, and syringic acid, protocatechuic acid and vanillic acid were confirmed to be the degradation products via anthocyanin chalcone conversion path. Gallic acid, protocatechuic acid, vanillic acid, syringic acid, and p-coumaric acid in wine experienced a significant concentration decrease during digestion process. However, wine model solution revealed that phenolic acids remained stable under gastrointestinal conditions, except gallic acid. Keywords: Cabernet Sauvignon wine; anthocyanins; degradation; stability; gastrointestinal pH and temperature 1. Introduction Anthocyanins are the major colorants in grapes and wine, and they have been confirmed to play important roles in affecting the appearance and sensory attributes of grapes and wine [1–5]. More importantly, anthocyanins can serve as one of the most important antioxidants in grapes and wine to provide multiple health promoting properties [6–8]. For example, it has been reported that anthocyanins possess the anti-cancer, anti-inflammatory, antimicrobial features, and the consumption of these antioxidants can lower the incidence of cardiovascular, diabetic, and obesity diseases [9–15]. Molecules 2018, 23, 354; doi:10.3390/molecules23020354 www.mdpi.com/journal/molecules Molecules 2018, 23, x FOR PEER REVIEW 2 of 19 Molecules 2018, 23, 354 2 of 20 anthocyanins possess the anti-cancer, anti-inflammatory, antimicrobial features, and the consumption of these antioxidants can lower the incidence of cardiovascular, diabetic, and obesity diseases [9–15]. Anthocyanins can can be be synthesized as as secondary metabolites in in grapes during the grape development period period [16,17]. [16,17]. These These colorants colorants can can be be extracted extracted into into red red wine wine during during the wine maceration process and they can further be metabolized during the wine fermentation and aging period [1,18,19]. [1,18,19]. Therefore, Therefore, the composition and co concentrationncentration of anthocyanins mainly determine the appearance of of red red wine. wine. It Ithas has been been reported reported that that the thelevel level of anthocyanins of anthocyanins in red in wine red wineranges ranges from 10from to 102000 to mg/L 2000 [19–21], mg/L [ 19and–21 their], and level their in levelwine inis winemainly is determined mainly determined by grape by variety, grape climate variety, conditions,climate conditions, management management system, and system, fermentation and fermentation technique technique [3,19,22–26]. [3,19 Regarding,22–26]. Regarding their chemical their nature,chemical anthocyanins nature, anthocyanins can be divided can beinto divided monomeri intoc anthocyanins monomeric anthocyanins (Figure 1), acylated (Figure anthocyanins,1), acylated pyranoanthocyanins,anthocyanins, pyranoanthocyanins, and polymeric anthocyanins and polymeric [27–31]. anthocyanins In Vitis vinifera [27–31 grapes]. In Vitisand wine, vinifera thegrapes major monomericand wine, theanthocyanins major monomeric include pelargonidin anthocyanins 3- includeO-glucoside, pelargonidin delphinidin 3-O 3--glucoside,O-glucoside, delphinidin cyanidin 3-O-glucoside, cyanidinpetunidin 3-O -glucoside,3-O-glucoside, petunidin peonidin 3-O-glucoside, 3-O-glucoside, peonidin and 3- Omalvidin-glucoside, 3- andO-glucoside malvidin (Figure3-O-glucoside 1) [2,26,31]. (Figure The1)[ monomeric2,26,31]. The anthocyanins monomeric anthocyaninscan be further can converted be further into converted the acetylated, into the coumaroylated,acetylated, coumaroylated, and caffeoylated and caffeoylatedanthocyanins anthocyanins [2,30,31]. Pyranoanthocyani [2,30,31]. Pyranoanthocyaninsns can be synthesized can be throughsynthesized conjugating through conjugatingmonomeric monomericor acylated oranthoc acylatedyanins anthocyanins with low molecu with lowlar molecular compounds compounds in wine, whereasin wine, whereasthe interaction the interaction among among anthocyanins anthocyanins or between or between anthocyanins anthocyanins and and other other phenolic compounds couldcould resultresult in in the the formation formation of of polymeric polymeric anthocyanins anthocyanins [30 –[30–333]. Pyranoanthocyanins3]. Pyranoanthocyanins and andpolymeric polymeric anthocyanins anthocyanins normally normally are formed are formed during du winering wine aging aging process, process, which which could could shift wineshift wine color colorfrom brightfrom bright red color red tocolor brick to andbrick dark and reddark color red [color34,35 [34,35].]. Anthocyanins R1 R2 DelphinidinAnthocyanins 3-O-glucoside ROH1 ROH2 DelphinidinCyanidin 3- 3-OO-glucoside-glucoside OHOH OHH CyanidinPetunidin 3-3-OO-glucoside-glucoside OHOCH3 HOH PetunidinPeonidin 3-O-glucoside OCHOCH3 3 OHH PeonidinMalvidin 3-3-OO-glucoside-glucoside OCHOCH3 3 OCHH 3 Malvidin 3-O-glucoside OCH3 OCH3 Figure 1. Five monomeric anthocyanins in red wine of Vitis Vinifera L. Figure 1. Five monomeric anthocyanins in red wine of Vitis Vinifera L. It has been reported that anthocyanins, like other phenolic compounds, can be absorbed through the humanIt has beengastrointestinal reported that tract. anthocyanins, The absorption like other rate of phenolic anthocyanins compounds, is repo canrted be to absorbed be around through 0.1% tothe 2%, human and gastrointestinal they could be tract.readily The distributed absorption rateto different of anthocyanins organs, isincluding reported toliver, be aroundlung, kidney, 0.1% to prostate,2%, and theyheart, could and brain be readily [6,36–38]. distributed The major to different digestive organs, segments including in the human liver, lung, gastrointestinal kidney, prostate, tract includeheart, and stomach brain [and6,36 small–38]. Theintestine. major Nutrient digestive digestion segments mainly in the happens human gastrointestinal in the stomach, tractwhereas include the smallstomach intestine and small is the intestine. major place Nutrient where digestion nutrients mainlyare absorbed happens [39,40]. in the It stomach,has been whereasreported thethat small 10% tointestine 25% of isanthocyanins the major place were where degraded nutrients in stomach, are absorbed whereas [39 the,40 small]. It has intestin beene reported was responsible that 10% for to 30% 25% toof anthocyanins50% of the anthocyanins’ were degraded degradation in stomach, [41–45]. whereas Anthocyanin the small intestine degradation was responsible can happen for 30%at their to 50% A- and/orof the anthocyanins’B-ring. The degradationA-ring degradation [41–45]. Anthocyaninhas been reported degradation to canresult happen in the at their formation A- and/or of formylphloroglucinalB-ring. The A-ring degradation or phlorogluc hasinol been carboxylic reported acid, to result whereas in the syri formationngic, vanillic of formylphloroglucinal and protocatechuic acidsor phloroglucinol were the major carboxylic products acid, from whereas the anthocya syringic,nins vanillicdegradation and protocatechuic via B-ring cleavage acids [46–48]. were the major productsIt has from been the anthocyaninsaccepted that degradation the percentage via B-ring of cleavageanthocyanins’ [46–48 degradation]. in the human gastrointestinalIt has been tract accepted is closely that thecorrelated percentage to the of anthocyanins’anthocyanins’ degradationstructure. However, in the human such investigationsgastrointestinal have tract isnot closely been correlatedwell documented to the anthocyanins’
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