摘要: 本研究以富含3類代表性酚類化合物（黃烷醇、黃烷酮和異黃酮）的3種食物（綠茶、橘皮、大豆）作為原料，模擬其在人體口胃腸中的體外消化過程。采用高效液相色譜-二極管陣列檢測器/電噴霧-四極桿-飛行時(shí)間串聯(lián)質(zhì)譜檢測器（HPLC-DAD/ESI-Q-TOF-MS）檢測體外消化前后酚類化合物的種類及含量變化，同時(shí)測定不同消化階段總酚含量（TPC）、總黃酮含量（TFC）以及抗氧化活性（DPPH、ABTS、FRAP、ORAC）的變化。結(jié)果表明，綠茶提取物中檢測出4種酚類化合物（表沒食子兒茶素、(+)-兒茶素、表沒食子兒茶素沒食子酸酯和表兒茶素沒食子酸酯），大豆提取物中檢測出4種酚類化合物（大豆苷、染料木苷、大豆苷元和染料木素），橘皮提取物中檢測出2種酚類化合物（柚皮苷和橙皮苷）；三種食物提取物中，經(jīng)過體外消化后，綠茶提取物中的酚類化合物最不穩(wěn)定，除(+)-兒茶素外，其余3種酚類物質(zhì)幾乎降解完全，損失率均達(dá)95%以上。綠茶、橘皮、大豆提取物的TPC在胃消化階段顯著升高（P<0.05），在腸消化階段顯著降低（P<0.05）。綠茶提取物TFC在口腔和胃消化階段顯著升高（P<0.05），在腸消化階段顯著降低（P<0.05）。橘皮、大豆提取物TFC與TPC變化趨勢一致。綠茶提取物的四種抗氧化活性經(jīng)胃腸消化后呈先升高再降低的趨勢。大豆提取液體外消化前后ABTS、FRAP抗氧化活性在口腔階段顯著降低（P<0.05），DPPH、ORAC抗氧化活性在口腔、胃消化階段顯著升高（P<0.05），在腸消化階段顯著降低（P<0.05）。橘皮提取液ORAC抗氧化活性在腸消化階段顯著升高（P<0.05），ABTS、FRAP抗氧化活性在體外消化階段均表現(xiàn)出和總酚含量變化一致的趨勢。

Abstract: In this study, three kinds of foods (green tea, citrus peel and soybean) rich in three representative phenolic compounds (flavanols, flavanones and isoflavones) were used as raw materials to simulate the in vitro digestion process in human oral and gastrointestinal tract. High performance liquid chromatography diode array detector/electrospray ionization quadrupole time of flight mass spectrometry detector (HPLC-DAD/ESI-Q-TOF-MS) was used to detect the variety and content of phenolic compounds before and after the in vitro digestion. The total phenol content (TPC), total flavonoids content (TFC) and antioxidant activity (DPPH, ABTS, FRAP, ORAC) in different digestion stages were determined. The results showed that four phenolic compounds (epigallocatechin, (+)-catechin, epigallocatechin gallate, epigallocatechin gallate) were detected in green tea extract, four phenolic compounds (daidzin, genistin, daidzein and genistein) were detected in soybean extract, and two phenolic compounds (naringin, hesperidin) were detected in citrus peel extract. Among the three food extracts, phenolic compounds in the green tea extract were the most unstable after in vitro digestion, except (+) -catechin, the other three phenolic compounds were almost completely degraded, the loss rate was more than 95%. TPC of green tea, citrus peel and soybean extracts was significantly increased in gastric digestion stage (P<0.05), and significantly decreased in intestinal digestion stage (P<0.05). TFC of green tea extract was significantly increased in oral and gastric digestion stage (P<0.05), and significantly decreased in intestinal digestion stage (P<0.05). TFC and TPC of citrus peel and soybean extract had the same change trend. The four antioxidant activities of green tea extract increased first and then decreased after gastrointestinal digestion. Antioxidant activities of ABTS, FRAP of soybean extract were significantly decreased in oral phase (P<0.05), antioxidant activities of DPPH, ORAC were significantly increased in oral and gastric digestion phase (P<0.05), and significantly decreased in intestinal digestion phase (P<0.05). The ORAC antioxidant activity of citrus peel extract was significantly increased in intestinal digestion stage (P<0.05), and the antioxidant activity of ABTS and FRAP showed a trend consistent with the change of total phenol content in in vitro digestion stage.

圖  1   模擬體外消化過程中綠茶提取物中酚類物質(zhì)的HPLC圖譜變化

注：1：表沒食子兒茶素；2：（+）-兒茶素；3：表沒食子兒茶素沒食子酸酯；4：表兒茶素沒食子酸酯。

Figure  1.   HPLC chromatogram changes of polyphenols in green tea extract during simulated in vitro digestion

圖  2   模擬體外消化過程中橘皮提取物中酚類物質(zhì)的HPLC圖譜變化

注：1：柚皮苷；2：橙皮苷。

Figure  2.   HPLC chromatogram changes of polyphenols in citrus peel extract during simulated in vitro digestion

圖  3   模擬體外消化過程中大豆提取物中酚類物質(zhì)的 HPLC 圖譜變化

注：1：大豆苷；2：染料木苷；3：大豆苷元；4：染料木素。

Figure  3.   HPLC chromatogram changes of polyphenols in soybean extract during simulated in vitro digestion

圖  4   大豆、綠茶、橘皮三種提取物體外消化前后總酚含量變化

注：同一樣品不同字母表示差異顯著（P<0.05）；圖5同。

Figure  4.   Changes of total phenolic content of soybean, green tea and citrus peel extracts during simulated in vitro digestion

圖  5   大豆、綠茶、橘皮三種提取物體外消化前后總黃酮含量變化

Figure  5.   Changes of total flavonoids content of soybean, green tea and citrus peel extracts during simulated in vitro digestion

表  1   模擬消化液儲備液的制備

Table  1   Preparation of stock solutions of simulated digestion fluids

主要成分各成分濃度
（mol/L）模擬口腔消化電解質(zhì)儲備液pH7模擬胃液消化電解質(zhì)儲備液pH3模擬腸液消化電解質(zhì)儲備液pH7體積（mL）濃度（mol/L）體積（mL）濃度（mol/L）體積（mL）濃度（mol/L） NaCl2——11.847.29.638.4NaHCO316.813.612.52542.585KCl0.515.115.16.96.96.86.8KH2PO40.53.73.70.90.90.80.8（NH4）2CO30.50.060.060.50.5——MgCl2（H2O）60.150.50.150.40.11.10.33

表  2   綠茶、橘皮、大豆高效液相色譜條件

Table  2   High performance liquid chromatography of green tea, citrus peel and soybean

物質(zhì)檢測波長（nm）流速（mL/min）柱溫（℃）進(jìn)樣量（μL）梯度洗脫條件 綠茶2700.530100~10 min：3%B；10~15 min：3%B~10%B；15~20 min：10%B~20%B；
20~25 min：20%B~25%B；25~30 min：25%B~30%B；
30~35 min：30%B~35%B；35~40 min：35%B~3%B；40~45 min：3%B橘皮2800.530100~5 min：16%B~16%B；5~5.5 min：16%B~22%B；
5.5~16.5 min：22%B~22%B；16.5~18.5 min：22%B~50%B；
18.5~20.5 min：50%B~39%B；20.5~30 min：39%B~39%B大豆2600.530100~10 min：12%B~18%B；10~23 min：18%B~24%B；
23~30 min：24%B~30%B；30~50 min：30%B；50~55 min：
30%B~80%B；55~56 min：80%B~12%B；56~60 min：12%B~12%B

表  3   模擬體外消化過程中綠茶提取物中酚類物質(zhì)的組分變化

Table  3   Component changes of polyphenols in green tea extract during simulated in vitro digestion

編號保留時(shí)間（min）分子式[M-H]-m/z主要碎片離子化合物名稱口消化損失率（%）胃消化損失率（%）腸消化損失率（%） 117.859C15H14O7305.0670167.0947，125.0246，111.049表沒食子兒茶素21.4314.6598.48218.558C15H14O6289.0725245.0815，205.0500，179.0345,
125.0243（+）-兒茶素7.7516.6689.11320.639C22H18O11457.0786306.0201，193.0141，169.0146，
125.0244表沒食子兒茶素沒食子酸酯52.8734.8899.71423.156C22H18O10441.0837289.0714，271.0605，269.052，
125.0240表兒茶素沒食子酸酯52.3337.7199.75

表  4   模擬體外消化過程中橘皮提取物中酚類物質(zhì)的組分變化

Table  4   Component changes of polyphenols in citrus peel extract during simulated in vitro digestion

編號保留時(shí)間（min）分子式[M-H]-m/z主要碎片離子化合物名稱口消化損失率（%）胃消化損失率（%）腸消化損失率（%） 18.926C27H32O14579.1753272.0654，151.0039，119.0504柚皮苷5.393.511.64210.106C28H34O15609.1863302.0760，286.0486，242.0584，
164.0114，125.0246橙皮苷15.0513.6516.19

表  5   模擬體外消化過程中大豆提取物中酚類物質(zhì)的組分變化

Table  5   Component changes of polyphenols in soybean extract during simulated in vitro digestion

編號保留時(shí)間（min）分子式[M-H]-m/z主要碎片離子化合物名稱口消化損失率（%）胃消化損失率（%）腸消化損失率（%） 17.137C21H20O9461.1116253.0503大豆苷21.3626.8431.22211.863C21H20O10431.0997269.0463染料木苷29.7932.9949.13313.368C15H10O4253.0518180.0585，133.0296大豆苷元5.455.0759.74418.940C15H10O5269.0466133.0300，107.0141染料木素24.1522.0144.94

表  6   三種提取物體外消化前后的抗氧化活性變化

Table  6   Changes of antioxidant activities of three extracts during simulated in vitro digestion

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