石榴籽原花色素提取纯化及其功能性研究
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摘要
石榴是一种既具有生态效益又具有经济效益的优良树种,近年来我国石榴种植面积和产量呈逐年上升趋势。石榴果实器官包括果皮、籽粒和隔膜三部分,各部分占果实重量的比例大约分别为55%、40%和5%。石榴籽粒包括外种皮即果肉(食用部分)、种壳和种仁三部分,各部分占籽粒重量(鲜重)的比例大约分别为62%、35%和3%。石榴籽中种仁约占石榴籽总重(干重)的25%,目前主要用于提取石榴籽油;榨油后剩余部分中含有的石榴籽原花色素是一种具有抗氧化、抗肿瘤等功能的成分。本文以陕西临潼区的石榴为试材,对石榴籽原花色素的提取、螯合剂的辅助提取、螯合剂等试剂对石榴籽原花色素稳定性的影响、石榴籽原花色素的纯化工艺、石榴籽原花色素的抗氧化性等进行了研究;采用大孔树脂和葡聚糖凝胶LH-20对石榴籽原花色素进行了纯化,同时运用紫外光谱、红外光谱、HPLC、ESI-MS等技术对原花色素的纯度及结构进行了分析鉴定。主要研究结果如下:
(1)采用螯合剂能提高多酚和石榴籽原花色素的提取效果。SH能置换出与金属离子(Fe2+、Sn2+、Pb2+、Mg2+、Cu2+、Zn2+)结合的原花色素;与对照相比石榴籽原花色素含量分别提高8.00%、13.97%、57.37%、25.59%、59.29%、34.50%,其中对Fe2+的作用效果最差,对Cu2+、Pb2+的作用效果最为明显。SH对石榴籽中多酚和原花色素的提取效果有明显的促进作用。
(2)通过比较香草醛—硫酸法和正丁醇—盐酸法,确定香草醛—硫酸法稳定性好、回收率高,可以准确测定石榴籽中原花色素的含量。应用香草醛—硫酸法对存放不同时间的石榴籽原花色素含量进行测定,结果表明石榴籽原花色素含量受存放时间长短影响,原花色素的提取应选择存放时间短的石榴籽作为原料。另外提取次数对原花色素的提取效果有一定影响,前三次提取到原花色素总量的85.4%,前四次得到原花色素总量的97.2%。
(3)在单因素试验的基础上,对影响石榴籽原花色素提取效果的乙醇浓度(X1)、提取时间(X2)和SH添加量(X3)3因素进行二次回归正交旋转组合设计,建立的数学回归模型为:Y=7.496+0.0797X1+0.2203X2+0.2111X3-0.2345X12+0.05722X22-0.00465X32+ 0.2838X1X2+0.0613X1X3-0.3138X2X3;优化出石榴籽原花色素的最佳提取工艺条件为:乙醇浓度60%、提取时间87min、SH添加量0.13%,在此优化条件下石榴籽原花色素得率为8.58%。
(4)采用有机溶剂洗涤、大孔树脂和葡聚糖凝胶LH-20等方法对石榴籽原花色素进行纯化。通过紫外光谱分析、红外光谱分析、磁共振波谱分析、液质联用等方法,研究了石榴籽原花色素的分子组成及其结构单元。结果表明,有机溶剂洗涤可以有效地除去脂肪族化合物,大孔树脂可以有效地除去糖、盐等杂质,葡聚糖凝胶LH-20可以去除其它的酚类物质。石榴籽原花色素主要结构单元是矢车菊素。
(5)在所选几个抗氧化指标中,DPPH?清除率、总还原能力与?OH清除率具有显著相关性,其余各指标之间的相关性都很小。石榴籽原花色素具有良好地抗氧化能力,其总还原力及对?OH、O2-?、DPPH?的清除能力随着浓度增大而增大,具有明显的量效关系,对?OH、O2-?和DPPH?的IC50分别为11.10μg/L、26.78μg/mL和102.32μg/L。不同浓度的石榴籽原花色素均可提高小鼠肝组织GSH-Px的活力,且二者之间存在量效关系。石榴籽原花色素可抑制H2O2诱导的脂质过氧化产物MDA的生成,并且抑制效果随原花色素浓度的增加而增强。
(6)在模拟的食品体系中,研究了各处理参数对石榴籽原花色素稳定性的影响。结果表明,在较低的温度条件下原花色素比较稳定;金属离子中以Sn2+、Fe2+和Cu2+对原花色素稳定性的影响最为显著,加入SH可以提高原花色素的稳定性;光照可使葡萄籽原花色素降解损失;Vc和亚硫酸氢钠可以提高原花色素的稳定性,且提高的效果同其浓度呈正相关;糖和食盐对原花色素均有很好地保护作用,不同浓度的糖和食盐对原花色素的保护作用不同,保护效果次序为:果糖>葡萄糖>食盐>蔗糖。石榴籽原花色素降解符合动力学一级反应,其反应活化能E0为35.29 kJ/mol,反应常数k0为4682.6,建立了石榴籽原花色素热降解的预测模型。经验证,模型与实测值拟合较好,表明该模型是合理的。
Pomegranate has been recognized as a verstaile nurtaceutical species with great economic and environmental potential in China,which is wideiy cultivated with an increasing production in recent ysars. Pomegranate can be divided into three parts, pomegranate peel, seed and septum, each several part are 55%、40%和5% respectively. Pomegranate seed include pulp, seed-case and kernel, pomegranate pulp 62%, pomegranate seed-case 35%, and kernel 3%. The weight of pomegranate kernels is about 25% of pomegranate seed. The main application of pomegranate seed is to extract oil. While the rest be researched lessly, in which has a lot of proanthocyanids. Poranthocyandins displays various types of physiological function including antioxidant activity, anti-tumor activity and anti-hypertensive activity. In this paper pomegranate planted in Lintong of Shanxi province was took as experimental material. This paper studied the technology for extracting proanthocyanids from pomegranate seed, extraction technology from pomegranate seed with chelon and the effect of chelon to proanthocyanids stability, the different technical methods of extraction, separation, purification of proanthocyanids and its antioxidant activity were studied. Proanthocyanids of pomegranate seed were purified by macroporous resin and Sephadex LH-20. Moreover, in the last chapters, the purity and structure of proanthocyanids were analyzed by means of UV spetrum, IR spetrum, high performance liquid chromatography, ESI-MS and other technologies. The main results were as follows:
(1) The yield can be raised with chelon to extract pomegranate phenol and proanthocyanids from pomegranate seed. The effect of SH to proanthocyanids with ions, such as Fe2+, Sn2+, Pb2+, Mg2+, Cu2+, Zn2+, was studied. The results show the contents of proanthocyanids improving 8.00%, 13.97%、57.37%、25.59%、59.29%、34.50%,contrast with control. The effect of SH to Fe2+ is the worst, to Cu2+, Pb2+is obvious. Extracting phenol and proanthocyanids from pomegranate seed can be promoted with SH obviously.
(2) Evaluation of vanillin assay proved that it has good repeatability and high recovery, and is also more sensitive and stable compared with normal butanol method. Proanthocyanids of pomegranate seeds can be quantified and compared by this method. Results showed that the proanthocyanids content of pomegranate seed was affected by storeage time. Proanthocyanids should be extracted from pomegranate seeds in short storage time. And the proanthocyanids content of pomegranate seed was affected by extracting times too, it shows we can obtain 85.4% proanthocyanids from pomegranate seed by extracted three times, obtain 97.2% by extracted four times.
(3) The extraction technology of proanthocyanids in pomegranate seed was optimized by quadric regression orthogonal rotary tests. The mathematics formula was: Y= 7.496+ 0.0797X1+ 0.2203X2+ 0.2111X3- 0.2345X12+ 0.05722X22- 0.00465X32+ 0.2838X1X2+ 0.0613X1X3- 0.3138X2X3, the optimum parameters of extraction were: ethanol concentration 60%, time 87min, SH concentration 0.13%, which content is 8.58%.
(4) Molecular composition and its construction unit of proanthocyanids from pomegranate seed after purification were characterized by UV spetrum, FT-IR spectroscopy, and electron paramagnetic resonance (EPR). The results show that aliphatic admixtures were removed by washing with organic solvents, and the saccharide and solubility saline content was reduced by macroporous resin, other phenolic compound was removed by Sephadex LH-20. HPLC- MS was used to purify and identify the proanthocyanids of pomegranate seed. The primary construction unit of proanthocyanids of pomegranate seed is cyanidin.
(5) Among these antioxidation indices, besides scavenging rate of DPPH? and reducing power and scavenging rate of ?OH show significant correlation both, there is no significant correlation each other. Proanthocyanids of pomegranate seed shows good antioxidant activity. Reducing power and scavenging rate of ?OH, O2-?, DPPH? of PSP increase with the increase of the concentration, and there are significant dose-effect relationship between them. The IC50 of ?OH, O2-?, DPPH? are 11.10μg/L, 26.78μg/mL, 102.32μg/L. PSP could also enhance the activity of GSH-Px, inhibit the production of MAD and hemolytic of red blood cell in mice, and the inhibition increase with the increase of the concentration.
(6) The stability of proanthocyanidins of pomegranate seed was studied in the simulate food systems. The results showed that proanthocyanidins of pomegranate seed were likely stable at low temperature. Among different metallic ions, Sn2+、Fe2+ and Cu2+ have significant influence on the stability of proanthocyanidins,adding SH makes it more stable. The amount would dcrease under the sun light,VC and NaHSO3 could improve the stability of proanthocyanidins, and their effects were related to their concentrations. Furthermoer, proanthocyanidins of pomegranate seed could be protected by sugars and common salt, the order of protect effect was: fructose> glucose > common salt > sucrose. The degradation of proanthocyanids of pomegranate seed is followed first-order reaction kinetics, and the thermal degradation activation energy of proanthocyanids of pomegranate seed is 35.29 kJ/mol, and the rate constant (k0) is 4682.6. The theoretical value and experimental value are propinquity, which indicate that the model is appropriate.
(1)采用螯合剂能提高多酚和石榴籽原花色素的提取效果。SH能置换出与金属离子(Fe2+、Sn2+、Pb2+、Mg2+、Cu2+、Zn2+)结合的原花色素;与对照相比石榴籽原花色素含量分别提高8.00%、13.97%、57.37%、25.59%、59.29%、34.50%,其中对Fe2+的作用效果最差,对Cu2+、Pb2+的作用效果最为明显。SH对石榴籽中多酚和原花色素的提取效果有明显的促进作用。
(2)通过比较香草醛—硫酸法和正丁醇—盐酸法,确定香草醛—硫酸法稳定性好、回收率高,可以准确测定石榴籽中原花色素的含量。应用香草醛—硫酸法对存放不同时间的石榴籽原花色素含量进行测定,结果表明石榴籽原花色素含量受存放时间长短影响,原花色素的提取应选择存放时间短的石榴籽作为原料。另外提取次数对原花色素的提取效果有一定影响,前三次提取到原花色素总量的85.4%,前四次得到原花色素总量的97.2%。
(3)在单因素试验的基础上,对影响石榴籽原花色素提取效果的乙醇浓度(X1)、提取时间(X2)和SH添加量(X3)3因素进行二次回归正交旋转组合设计,建立的数学回归模型为:Y=7.496+0.0797X1+0.2203X2+0.2111X3-0.2345X12+0.05722X22-0.00465X32+ 0.2838X1X2+0.0613X1X3-0.3138X2X3;优化出石榴籽原花色素的最佳提取工艺条件为:乙醇浓度60%、提取时间87min、SH添加量0.13%,在此优化条件下石榴籽原花色素得率为8.58%。
(4)采用有机溶剂洗涤、大孔树脂和葡聚糖凝胶LH-20等方法对石榴籽原花色素进行纯化。通过紫外光谱分析、红外光谱分析、磁共振波谱分析、液质联用等方法,研究了石榴籽原花色素的分子组成及其结构单元。结果表明,有机溶剂洗涤可以有效地除去脂肪族化合物,大孔树脂可以有效地除去糖、盐等杂质,葡聚糖凝胶LH-20可以去除其它的酚类物质。石榴籽原花色素主要结构单元是矢车菊素。
(5)在所选几个抗氧化指标中,DPPH?清除率、总还原能力与?OH清除率具有显著相关性,其余各指标之间的相关性都很小。石榴籽原花色素具有良好地抗氧化能力,其总还原力及对?OH、O2-?、DPPH?的清除能力随着浓度增大而增大,具有明显的量效关系,对?OH、O2-?和DPPH?的IC50分别为11.10μg/L、26.78μg/mL和102.32μg/L。不同浓度的石榴籽原花色素均可提高小鼠肝组织GSH-Px的活力,且二者之间存在量效关系。石榴籽原花色素可抑制H2O2诱导的脂质过氧化产物MDA的生成,并且抑制效果随原花色素浓度的增加而增强。
(6)在模拟的食品体系中,研究了各处理参数对石榴籽原花色素稳定性的影响。结果表明,在较低的温度条件下原花色素比较稳定;金属离子中以Sn2+、Fe2+和Cu2+对原花色素稳定性的影响最为显著,加入SH可以提高原花色素的稳定性;光照可使葡萄籽原花色素降解损失;Vc和亚硫酸氢钠可以提高原花色素的稳定性,且提高的效果同其浓度呈正相关;糖和食盐对原花色素均有很好地保护作用,不同浓度的糖和食盐对原花色素的保护作用不同,保护效果次序为:果糖>葡萄糖>食盐>蔗糖。石榴籽原花色素降解符合动力学一级反应,其反应活化能E0为35.29 kJ/mol,反应常数k0为4682.6,建立了石榴籽原花色素热降解的预测模型。经验证,模型与实测值拟合较好,表明该模型是合理的。
Pomegranate has been recognized as a verstaile nurtaceutical species with great economic and environmental potential in China,which is wideiy cultivated with an increasing production in recent ysars. Pomegranate can be divided into three parts, pomegranate peel, seed and septum, each several part are 55%、40%和5% respectively. Pomegranate seed include pulp, seed-case and kernel, pomegranate pulp 62%, pomegranate seed-case 35%, and kernel 3%. The weight of pomegranate kernels is about 25% of pomegranate seed. The main application of pomegranate seed is to extract oil. While the rest be researched lessly, in which has a lot of proanthocyanids. Poranthocyandins displays various types of physiological function including antioxidant activity, anti-tumor activity and anti-hypertensive activity. In this paper pomegranate planted in Lintong of Shanxi province was took as experimental material. This paper studied the technology for extracting proanthocyanids from pomegranate seed, extraction technology from pomegranate seed with chelon and the effect of chelon to proanthocyanids stability, the different technical methods of extraction, separation, purification of proanthocyanids and its antioxidant activity were studied. Proanthocyanids of pomegranate seed were purified by macroporous resin and Sephadex LH-20. Moreover, in the last chapters, the purity and structure of proanthocyanids were analyzed by means of UV spetrum, IR spetrum, high performance liquid chromatography, ESI-MS and other technologies. The main results were as follows:
(1) The yield can be raised with chelon to extract pomegranate phenol and proanthocyanids from pomegranate seed. The effect of SH to proanthocyanids with ions, such as Fe2+, Sn2+, Pb2+, Mg2+, Cu2+, Zn2+, was studied. The results show the contents of proanthocyanids improving 8.00%, 13.97%、57.37%、25.59%、59.29%、34.50%,contrast with control. The effect of SH to Fe2+ is the worst, to Cu2+, Pb2+is obvious. Extracting phenol and proanthocyanids from pomegranate seed can be promoted with SH obviously.
(2) Evaluation of vanillin assay proved that it has good repeatability and high recovery, and is also more sensitive and stable compared with normal butanol method. Proanthocyanids of pomegranate seeds can be quantified and compared by this method. Results showed that the proanthocyanids content of pomegranate seed was affected by storeage time. Proanthocyanids should be extracted from pomegranate seeds in short storage time. And the proanthocyanids content of pomegranate seed was affected by extracting times too, it shows we can obtain 85.4% proanthocyanids from pomegranate seed by extracted three times, obtain 97.2% by extracted four times.
(3) The extraction technology of proanthocyanids in pomegranate seed was optimized by quadric regression orthogonal rotary tests. The mathematics formula was: Y= 7.496+ 0.0797X1+ 0.2203X2+ 0.2111X3- 0.2345X12+ 0.05722X22- 0.00465X32+ 0.2838X1X2+ 0.0613X1X3- 0.3138X2X3, the optimum parameters of extraction were: ethanol concentration 60%, time 87min, SH concentration 0.13%, which content is 8.58%.
(4) Molecular composition and its construction unit of proanthocyanids from pomegranate seed after purification were characterized by UV spetrum, FT-IR spectroscopy, and electron paramagnetic resonance (EPR). The results show that aliphatic admixtures were removed by washing with organic solvents, and the saccharide and solubility saline content was reduced by macroporous resin, other phenolic compound was removed by Sephadex LH-20. HPLC- MS was used to purify and identify the proanthocyanids of pomegranate seed. The primary construction unit of proanthocyanids of pomegranate seed is cyanidin.
(5) Among these antioxidation indices, besides scavenging rate of DPPH? and reducing power and scavenging rate of ?OH show significant correlation both, there is no significant correlation each other. Proanthocyanids of pomegranate seed shows good antioxidant activity. Reducing power and scavenging rate of ?OH, O2-?, DPPH? of PSP increase with the increase of the concentration, and there are significant dose-effect relationship between them. The IC50 of ?OH, O2-?, DPPH? are 11.10μg/L, 26.78μg/mL, 102.32μg/L. PSP could also enhance the activity of GSH-Px, inhibit the production of MAD and hemolytic of red blood cell in mice, and the inhibition increase with the increase of the concentration.
(6) The stability of proanthocyanidins of pomegranate seed was studied in the simulate food systems. The results showed that proanthocyanidins of pomegranate seed were likely stable at low temperature. Among different metallic ions, Sn2+、Fe2+ and Cu2+ have significant influence on the stability of proanthocyanidins,adding SH makes it more stable. The amount would dcrease under the sun light,VC and NaHSO3 could improve the stability of proanthocyanidins, and their effects were related to their concentrations. Furthermoer, proanthocyanidins of pomegranate seed could be protected by sugars and common salt, the order of protect effect was: fructose> glucose > common salt > sucrose. The degradation of proanthocyanids of pomegranate seed is followed first-order reaction kinetics, and the thermal degradation activation energy of proanthocyanids of pomegranate seed is 35.29 kJ/mol, and the rate constant (k0) is 4682.6. The theoretical value and experimental value are propinquity, which indicate that the model is appropriate.
引文
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