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绿茶、橘皮、大豆中酚类物质体外消化前后稳定性及抗氧化活性的研究

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2024-12-15 18:10

摘要: 本研究以富含3类代表性酚类化合物（黄烷醇、黄烷酮和异黄酮）的3种食物（绿茶、橘皮、大豆）作为原料，模拟其在人体口胃肠中的体外消化过程。采用高效液相色谱-二极管阵列检测器/电喷雾-四极杆-飞行时间串联质谱检测器（HPLC-DAD/ESI-Q-TOF-MS）检测体外消化前后酚类化合物的种类及含量变化，同时测定不同消化阶段总酚含量（TPC）、总黄酮含量（TFC）以及抗氧化活性（DPPH、ABTS、FRAP、ORAC）的变化。结果表明，绿茶提取物中检测出4种酚类化合物（表没食子儿茶素、(+)-儿茶素、表没食子儿茶素没食子酸酯和表儿茶素没食子酸酯），大豆提取物中检测出4种酚类化合物（大豆苷、染料木苷、大豆苷元和染料木素），橘皮提取物中检测出2种酚类化合物（柚皮苷和橙皮苷）；三种食物提取物中，经过体外消化后，绿茶提取物中的酚类化合物最不稳定，除(+)-儿茶素外，其余3种酚类物质几乎降解完全，损失率均达95%以上。绿茶、橘皮、大豆提取物的TPC在胃消化阶段显著升高（P<0.05），在肠消化阶段显著降低（P<0.05）。绿茶提取物TFC在口腔和胃消化阶段显著升高（P<0.05），在肠消化阶段显著降低（P<0.05）。橘皮、大豆提取物TFC与TPC变化趋势一致。绿茶提取物的四种抗氧化活性经胃肠消化后呈先升高再降低的趋势。大豆提取液体外消化前后ABTS、FRAP抗氧化活性在口腔阶段显著降低（P<0.05），DPPH、ORAC抗氧化活性在口腔、胃消化阶段显著升高（P<0.05），在肠消化阶段显著降低（P<0.05）。橘皮提取液ORAC抗氧化活性在肠消化阶段显著升高（P<0.05），ABTS、FRAP抗氧化活性在体外消化阶段均表现出和总酚含量变化一致的趋势。

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.

图 1 模拟体外消化过程中绿茶提取物中酚类物质的HPLC图谱变化

注：1：表没食子儿茶素；2：（+）-儿茶素；3：表没食子儿茶素没食子酸酯；4：表儿茶素没食子酸酯。

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

图 2 模拟体外消化过程中橘皮提取物中酚类物质的HPLC图谱变化

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

图 3 模拟体外消化过程中大豆提取物中酚类物质的 HPLC 图谱变化

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

图 4 大豆、绿茶、橘皮三种提取物体外消化前后总酚含量变化

注：同一样品不同字母表示差异显著（P<0.05）；图5同。

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

图 5 大豆、绿茶、橘皮三种提取物体外消化前后总黄酮含量变化

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

表 1 模拟消化液储备液的制备

Table 1 Preparation of stock solutions of simulated digestion fluids

主要成分各成分浓度
（mol/L）模拟口腔消化电解质储备液pH7模拟胃液消化电解质储备液pH3模拟肠液消化电解质储备液pH7体积（mL）浓度（mol/L）体积（mL）浓度（mol/L）体积（mL）浓度（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 绿茶、橘皮、大豆高效液相色谱条件

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

物质检测波长（nm）流速（mL/min）柱温（℃）进样量（µL）梯度洗脱条件绿茶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 模拟体外消化过程中绿茶提取物中酚类物质的组分变化

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

编号保留时间（min）分子式[M-H]-m/z主要碎片离子化合物名称口消化损失率（%）胃消化损失率（%）肠消化损失率（%） 117.859C15H14O7305.0670167.0947，125.0246，111.049表没食子儿茶素21.4314.6598.48218.558C15H14O6289.0725245.0815，205.0500，179.0345,
125.0243（+）-儿茶素7.7516.6689.11320.639C22H18O11457.0786306.0201，193.0141，169.0146，
125.0244表没食子儿茶素没食子酸酯52.8734.8899.71423.156C22H18O10441.0837289.0714，271.0605，269.052，
125.0240表儿茶素没食子酸酯52.3337.7199.75

表 4 模拟体外消化过程中橘皮提取物中酚类物质的组分变化

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

编号保留时间（min）分子式[M-H]-m/z主要碎片离子化合物名称口消化损失率（%）胃消化损失率（%）肠消化损失率（%） 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 模拟体外消化过程中大豆提取物中酚类物质的组分变化

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

编号保留时间（min）分子式[M-H]-m/z主要碎片离子化合物名称口消化损失率（%）胃消化损失率（%）肠消化损失率（%） 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 三种提取物体外消化前后的抗氧化活性变化

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

样品消化阶段ABTS（μmol TE/g DW）DPPH（μmol TE/g DW）FRAP（μmol TE/g DW）ORAC（μmol TE/g DW）绿茶未消化986.59±9.86a954.66±18.77b621.25±14.93a2742.45±156.45a口消化707.73±16.84c711.53±18.23c508.13±37.44c1092.35±40.65c胃消化935.33±18.92b1159.89±70.16a572.50±5.00b1290.12±51.47b肠消化420.77±20.84d378.12±8.53d212.50±4.12d997.85±68.89c大豆未消化14.95±0.08b11.62±0.89c6.48±0.29b38.76±0.64c口消化11.95±0.67c13.64±0.85b5.71±0.29c88.67±10.31b胃消化18.23±0.13a17.86±0.72a7.19±0.23a179.28±3.80a肠消化9.11±0.10d4.64±0.08d5.72±0.21c23.26±0.32d橘皮未消化79.91±0.17b37.11±0.24b57.58±1.44a335.50±74.15c口消化72.44±1.85c41.74±1.27a46.17±1.53b319.53±63.11c胃消化86.35±0.88a28.60±1.13c55.83±2.89a501.64±62.77b肠消化39.51±0.99d28.39±1.57c48.23±2.14b649.00±18.05a 注：同一样品同列不同字母表示差异显著（P<0.05）。 [1] 刘昕皓, 魏粉菊, 王学顺, 等. 多酚类化合物的生物活性研究进展[J]. 中国医药工业杂志,2021,52(4):471−483. [LIU Xinhao, WEI Fenju, WANG Xueshun, et al. Progress on biological activities of polyphenols[J]. Chinese Journal of Pharmaceuticals,2021,52(4):471−483.

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