橄榄酚类化合物的分离纯化和结构研究
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摘要
橄榄(Canarium album L.)为我国珍贵的药食两用资源,具有解酒护肝、抗菌消炎、抗病毒和解毒等药理功效,橄榄中酚类化合物是其主要的药效成分,但国内外有关橄榄酚类化合物组成的研究报道不多。本论文对我国橄榄果实中的酚类化合物进行提取、分离和纯化,并对酚类化合物单体的化学结构进行鉴定研究,以明确橄榄酚类的具体组成,对于橄榄资源的深加工利用和橄榄中药的药理研究具有重要的指导意义和应用价值。
首先采用化学和仪器分析方法对福建闽侯檀香橄榄果实不同部分的化学组成进行了分析测定,结果表明,橄榄果肉中蛋白质含量为1.7 g/100g,脂肪含量为1.1 g/100g,可溶性糖含量分别为蔗糖635 mg/100g、果糖232 mg/100g、葡萄糖52 mg/100g、棉子糖30 mg/100g和麦芽糖7 mg/100g,有机酸含量分别为苹果酸537 mg/100g、柠檬酸64 mg/100g、酒石酸34 mg/100g、奎宁酸28 mg/100g、草酸24 mg/100g、富马酸14 mg/100g和乙酸11 mg/100g,由改良Folin-Ciocalteus比色法测定的橄榄果肉部分中的酚类成分含量为1.5 g/100g,高于地中海油橄榄和普通水果,而橄榄核中酚类含量较低(0.2 g/100g);橄榄核仁中蛋白质和脂肪含量之和高达82.3%,蛋白中氨基酸种类齐全,橄榄核仁油不饱和脂肪酸相对含量为73.3%,核仁中钙、铁等矿物元素丰富,橄榄核仁资源具有很好的开发利用前景。
采用溶剂浸提法、超声波辅助提取和微波辅助提取方法对橄榄果肉中的酚类化合物进行了提取研究,结果表明,橄榄酚类化合物的最佳提取溶剂为60~70%(V/V)丙酮溶液,但在实际工业应用中以60%(V/V)乙醇溶液为宜,溶剂浸提法的最佳提取时间为1 h,温度为20~30℃,固液比1:20,提取次数2次;超声辅助提取的最适功率为80 w,最佳提取时间25 min;微波辅助提取的最适功率为340 w,提取时间为30 s。三种提取方法的酚类得率差别不显著(P>0.05),提取物酚类组成基本相同,提取率均可达90%以上,提取物中酚类含量约为34%,相比于溶剂浸提法,超声波和微波辅助提取方法可显著缩短橄榄酚类的提取时间,提高提取效率。
采用大孔树脂吸附法对橄榄酚类提取物进行了纯化研究,结果表明,AB-8型大孔吸附树脂对橄榄酚类化合物具有较好的吸附和解吸性能,较适合于橄榄酚类成分的纯化,树脂柱(Φ2.5 cm×30 cm)的纯化工艺条件为:酚液pH值为其自然pH(3.7),酚液浓度10 mg/ml,吸附流速2 ml/min,吸附温度为室温,此时树脂对酚类化合物吸附量最大,当上样体积达2倍柱床体积时酚类开始泄漏,当达到9倍柱床体积时,树脂吸附达到饱和,对吸附饱和的树脂进行洗脱,先用3.5倍柱床体积的去离子水洗去糖、蛋白等杂质,然后采用2.5倍柱床体积的90%(V/V)乙醇溶液以1 ml/min的洗脱流速冲洗树脂,酚类解吸率可达95%以上。纯化后的橄榄酚类产品纯度从原先粗提物的34%提高到86%,纯化倍数达2.5倍,高于专利报道的76%的产品纯度,产品酚类得率为1.4%,回收率为74%。
利用硅胶柱层析、AB-8型大孔吸附树脂柱层析、聚酰胺柱层析、TSKgel Toyopearl HW-40柱层析以及制备硅胶薄层层析等多种方法对橄榄酚类提取物中的酚类组成进行了分离纯化并采用HPLC法对各酚类化合物的相对含量进行测定,结果表明,从橄榄果实中提取分离出了16种酚类化合物单体,并通过UV、IR、HPLC-ESI-MS、1D NMR(1H-NMR、13C-NMR、DEPT-135)和2D NMR(1H-1H COSY、HMQC、HMBC)等波谱检测技术及结合化学方法对酚类化合物单体的结构进行了鉴定,橄榄果实酚类化合物组成分别为:没食子酸28.6%、3, 3′-二甲氧基-2, 2′, 4, 4′-四羟基联苯二甲酸1.5%、六羟基联苯二甲酸(HHDP)的烷基化衍生物Ⅳ1.7%和Ⅴ4.1%、没食子酸甲酯3.8%、金丝桃苷2.3%、山萘酚-3-O-β-D-葡萄糖苷2.9%、穗花衫双黄酮1.1%、六羟基联苯二甲酸(HHDP)的糖酯类化合物Ⅹ14.3%和Ⅻ11.6%、异柯里拉京3.1%、短叶苏木酚酸3.2%、没食子酸乙酯1.3%、3-O-没食子酰基奎宁酸丁酯2.6%、芥子酸0.6%、相对分子质量为348的酚酸类化合物Ⅰ2.1%。其中,3-O-没食子酰基奎宁酸丁酯为一新的酚类化合物,其余化合物除没食子酸和金丝桃苷外均是首次在橄榄植物中分离得到。
Chinese olive (Canarium album L.), a valuable resource for traditional medicine and food use, possesses some pharmacological functions such as anti-bacterium, anti-virus, anti-inflammation and detoxification. Previous study has showed that Chinese olive fruit is rich in phenolic compounds which were closely related to its organoleptic and pharmacological characteristics. However, up to date, reports on separation and identification of phenolic compounds from C. album were terribly scarce, and phenolic profile of C. album was still uncertain. Therefore, the purpose of the present work was to extract, isolate and purify the phenolic compounds from Chinese olive fruit, and elucidate their structures by chromatographic and spectrometric techniques, which will be of great significance for further utilization and pharmacological investigation of Chinese olive.
First, chemical components of Chinese olive fruit cultivated from Fujian Minhou area were analysed. The results indicated that Chinese olive fruit pulp contained protein 1.7 g/100g and fat 1.1 g/100g. The main saccharides of C. album fruit were sucrose (635 mg/100g), fructose (232 mg/100g), glucose (52 mg/100g), raffinose (30 mg/100g) and maltose (7 mg/100g). The organic acids of fruit were malic acid (537 mg/100g), citric acid (64 mg/100g), tartaric acid (34 mg/100g), quinic acid (28 mg/100g), oxalic acid (24 mg/100g), fumaric acid (14 mg/100g) and acetic acid (11 mg/100g). The phenolic content of fruit pulp determined by modified Folin-Ciocalteus method was 1.5 g/100g, obviously higher than Mediterranean olive (Olea europaea L.) and other common fruits, while Chinese olive stone presented low phenolic content (0.2 g/100g). C. album kernels had relatively high fat (52.8%), protein (29.5%), iron and calcium contents. The kernel proteins were rich in essential amino acids. The kernel oils were rich in unsaturation fatty acids (73.3%), which showed that C. album kernels had great potential for use as food resources.
Extraction of phenolic compounds from Chinese olive fruit was investigated by solvent digestion, supersonic-assisted and microwave-assisted methods. The results showed that 60~70% (V/V) acetone was the best solvent for phenolic extraction, but 60% (V/V) ethanol was preferable in industry application. The optimum conditions for solvent digestion were as follows: leaching time 1 h,temperature 20~30℃, material/solvent ratio 1:20. The optimal power and extraction time for supersonic assisted extraction were 80 w and 25 min, while that for microwave assisted extraction were 340 w and 30 s. The phenolic yields of three methods differed insignificantly (P>0.05), and their phenolic compositions were almost same. The extraction rate was up to 90%, and Chinese olive crude extracts containing 34% phenolics was obtained. In comparation with solvent extraction method, supersonic-assisted and microwave-assisted method were more rapid and efficient for extracting phenolics from Chinese olive fruit.
Purification of phenolic crude extract from Chinese olive on macroporous resin was studied. Through static adsorption and desorption tests, AB-8 resin was chosen for the separation of phenolics due to its higher adsorption and desorption capacity. Then, dynamic adsorption and desorption experiment was carried out on an AB-8 resin packed column (Φ2.5 cm×30 cm) to obtain optimal separation parameters. The results revealed that the largest adsorption capacity of AB-8 was achieved when initial phenolic concentration was 10 mg/ml, feed flow rate was 2 ml/min and feed volume was 9 bed volume (BV). The saturated resin was first washed with 3.5 BV of water to remove impurities, then desobed with 2.5 BV of 90% aqueous ethanol at flow rate of 1 ml/min. The desorption ration of phenolics from resin was up to 95%, and the purity of phenolic in crude extracts was increased from 34% to 86%, higher than that patent reported (76%). The recovery of phenolics was about 74%.
The phenolic compounds in crude extract from Chinese olive fruit were separated and purified by silica gel column, AB-8 macroporous resin column, polyamide column, TSKgel Toyopearl HW-40 column and thin layer chromatography, and the relative contents of phenolic compositions in crude extract were determined by HPLC. The results indicated that sixteen phenolic compounds were obtained from Chinese olive fruit, and by UV、IR、HPLC-ESI-MS、1D NMR (1H-NMR、13C-NMR、DEPT-135) and 2D NMR (1H-1H COSY、HMQC、HMBC) spectrometric techniques, phenolic compositions in crude extract were elucidated as followings: gallic acid (28.6%), HHDP hexose ester isomers (Ⅹ14.3%,Ⅻ11.6%), HHDP alkyl derivatives (Ⅴ4.1%,Ⅳ1.7%), methyl gallate (3.8%), brevifolin-carboxylic acid (3.2%), isocorilagin (3.1%), kaempferol-3-O-β-D-glucopyranoside (2.9%), 3-O-galloyl quinic acid butyl ester (2.6%), hyperin (2.3%), phenolic acid with Mw 348 (Ⅰ2.1%), 3,3′-dimethoxy-2,2′,4,4′-tetrahydroxy- diphenylformic acid (1.5%), ethyl gallate (1.3%), amentoflavone (1.1%) and sinapic acid (0.6%). Among them, 3-O-galloyl quinic acid butyl ester was one new phenolic compound, remaining compounds except gallic acid and hyperin were first identified in C. album
首先采用化学和仪器分析方法对福建闽侯檀香橄榄果实不同部分的化学组成进行了分析测定,结果表明,橄榄果肉中蛋白质含量为1.7 g/100g,脂肪含量为1.1 g/100g,可溶性糖含量分别为蔗糖635 mg/100g、果糖232 mg/100g、葡萄糖52 mg/100g、棉子糖30 mg/100g和麦芽糖7 mg/100g,有机酸含量分别为苹果酸537 mg/100g、柠檬酸64 mg/100g、酒石酸34 mg/100g、奎宁酸28 mg/100g、草酸24 mg/100g、富马酸14 mg/100g和乙酸11 mg/100g,由改良Folin-Ciocalteus比色法测定的橄榄果肉部分中的酚类成分含量为1.5 g/100g,高于地中海油橄榄和普通水果,而橄榄核中酚类含量较低(0.2 g/100g);橄榄核仁中蛋白质和脂肪含量之和高达82.3%,蛋白中氨基酸种类齐全,橄榄核仁油不饱和脂肪酸相对含量为73.3%,核仁中钙、铁等矿物元素丰富,橄榄核仁资源具有很好的开发利用前景。
采用溶剂浸提法、超声波辅助提取和微波辅助提取方法对橄榄果肉中的酚类化合物进行了提取研究,结果表明,橄榄酚类化合物的最佳提取溶剂为60~70%(V/V)丙酮溶液,但在实际工业应用中以60%(V/V)乙醇溶液为宜,溶剂浸提法的最佳提取时间为1 h,温度为20~30℃,固液比1:20,提取次数2次;超声辅助提取的最适功率为80 w,最佳提取时间25 min;微波辅助提取的最适功率为340 w,提取时间为30 s。三种提取方法的酚类得率差别不显著(P>0.05),提取物酚类组成基本相同,提取率均可达90%以上,提取物中酚类含量约为34%,相比于溶剂浸提法,超声波和微波辅助提取方法可显著缩短橄榄酚类的提取时间,提高提取效率。
采用大孔树脂吸附法对橄榄酚类提取物进行了纯化研究,结果表明,AB-8型大孔吸附树脂对橄榄酚类化合物具有较好的吸附和解吸性能,较适合于橄榄酚类成分的纯化,树脂柱(Φ2.5 cm×30 cm)的纯化工艺条件为:酚液pH值为其自然pH(3.7),酚液浓度10 mg/ml,吸附流速2 ml/min,吸附温度为室温,此时树脂对酚类化合物吸附量最大,当上样体积达2倍柱床体积时酚类开始泄漏,当达到9倍柱床体积时,树脂吸附达到饱和,对吸附饱和的树脂进行洗脱,先用3.5倍柱床体积的去离子水洗去糖、蛋白等杂质,然后采用2.5倍柱床体积的90%(V/V)乙醇溶液以1 ml/min的洗脱流速冲洗树脂,酚类解吸率可达95%以上。纯化后的橄榄酚类产品纯度从原先粗提物的34%提高到86%,纯化倍数达2.5倍,高于专利报道的76%的产品纯度,产品酚类得率为1.4%,回收率为74%。
利用硅胶柱层析、AB-8型大孔吸附树脂柱层析、聚酰胺柱层析、TSKgel Toyopearl HW-40柱层析以及制备硅胶薄层层析等多种方法对橄榄酚类提取物中的酚类组成进行了分离纯化并采用HPLC法对各酚类化合物的相对含量进行测定,结果表明,从橄榄果实中提取分离出了16种酚类化合物单体,并通过UV、IR、HPLC-ESI-MS、1D NMR(1H-NMR、13C-NMR、DEPT-135)和2D NMR(1H-1H COSY、HMQC、HMBC)等波谱检测技术及结合化学方法对酚类化合物单体的结构进行了鉴定,橄榄果实酚类化合物组成分别为:没食子酸28.6%、3, 3′-二甲氧基-2, 2′, 4, 4′-四羟基联苯二甲酸1.5%、六羟基联苯二甲酸(HHDP)的烷基化衍生物Ⅳ1.7%和Ⅴ4.1%、没食子酸甲酯3.8%、金丝桃苷2.3%、山萘酚-3-O-β-D-葡萄糖苷2.9%、穗花衫双黄酮1.1%、六羟基联苯二甲酸(HHDP)的糖酯类化合物Ⅹ14.3%和Ⅻ11.6%、异柯里拉京3.1%、短叶苏木酚酸3.2%、没食子酸乙酯1.3%、3-O-没食子酰基奎宁酸丁酯2.6%、芥子酸0.6%、相对分子质量为348的酚酸类化合物Ⅰ2.1%。其中,3-O-没食子酰基奎宁酸丁酯为一新的酚类化合物,其余化合物除没食子酸和金丝桃苷外均是首次在橄榄植物中分离得到。
Chinese olive (Canarium album L.), a valuable resource for traditional medicine and food use, possesses some pharmacological functions such as anti-bacterium, anti-virus, anti-inflammation and detoxification. Previous study has showed that Chinese olive fruit is rich in phenolic compounds which were closely related to its organoleptic and pharmacological characteristics. However, up to date, reports on separation and identification of phenolic compounds from C. album were terribly scarce, and phenolic profile of C. album was still uncertain. Therefore, the purpose of the present work was to extract, isolate and purify the phenolic compounds from Chinese olive fruit, and elucidate their structures by chromatographic and spectrometric techniques, which will be of great significance for further utilization and pharmacological investigation of Chinese olive.
First, chemical components of Chinese olive fruit cultivated from Fujian Minhou area were analysed. The results indicated that Chinese olive fruit pulp contained protein 1.7 g/100g and fat 1.1 g/100g. The main saccharides of C. album fruit were sucrose (635 mg/100g), fructose (232 mg/100g), glucose (52 mg/100g), raffinose (30 mg/100g) and maltose (7 mg/100g). The organic acids of fruit were malic acid (537 mg/100g), citric acid (64 mg/100g), tartaric acid (34 mg/100g), quinic acid (28 mg/100g), oxalic acid (24 mg/100g), fumaric acid (14 mg/100g) and acetic acid (11 mg/100g). The phenolic content of fruit pulp determined by modified Folin-Ciocalteus method was 1.5 g/100g, obviously higher than Mediterranean olive (Olea europaea L.) and other common fruits, while Chinese olive stone presented low phenolic content (0.2 g/100g). C. album kernels had relatively high fat (52.8%), protein (29.5%), iron and calcium contents. The kernel proteins were rich in essential amino acids. The kernel oils were rich in unsaturation fatty acids (73.3%), which showed that C. album kernels had great potential for use as food resources.
Extraction of phenolic compounds from Chinese olive fruit was investigated by solvent digestion, supersonic-assisted and microwave-assisted methods. The results showed that 60~70% (V/V) acetone was the best solvent for phenolic extraction, but 60% (V/V) ethanol was preferable in industry application. The optimum conditions for solvent digestion were as follows: leaching time 1 h,temperature 20~30℃, material/solvent ratio 1:20. The optimal power and extraction time for supersonic assisted extraction were 80 w and 25 min, while that for microwave assisted extraction were 340 w and 30 s. The phenolic yields of three methods differed insignificantly (P>0.05), and their phenolic compositions were almost same. The extraction rate was up to 90%, and Chinese olive crude extracts containing 34% phenolics was obtained. In comparation with solvent extraction method, supersonic-assisted and microwave-assisted method were more rapid and efficient for extracting phenolics from Chinese olive fruit.
Purification of phenolic crude extract from Chinese olive on macroporous resin was studied. Through static adsorption and desorption tests, AB-8 resin was chosen for the separation of phenolics due to its higher adsorption and desorption capacity. Then, dynamic adsorption and desorption experiment was carried out on an AB-8 resin packed column (Φ2.5 cm×30 cm) to obtain optimal separation parameters. The results revealed that the largest adsorption capacity of AB-8 was achieved when initial phenolic concentration was 10 mg/ml, feed flow rate was 2 ml/min and feed volume was 9 bed volume (BV). The saturated resin was first washed with 3.5 BV of water to remove impurities, then desobed with 2.5 BV of 90% aqueous ethanol at flow rate of 1 ml/min. The desorption ration of phenolics from resin was up to 95%, and the purity of phenolic in crude extracts was increased from 34% to 86%, higher than that patent reported (76%). The recovery of phenolics was about 74%.
The phenolic compounds in crude extract from Chinese olive fruit were separated and purified by silica gel column, AB-8 macroporous resin column, polyamide column, TSKgel Toyopearl HW-40 column and thin layer chromatography, and the relative contents of phenolic compositions in crude extract were determined by HPLC. The results indicated that sixteen phenolic compounds were obtained from Chinese olive fruit, and by UV、IR、HPLC-ESI-MS、1D NMR (1H-NMR、13C-NMR、DEPT-135) and 2D NMR (1H-1H COSY、HMQC、HMBC) spectrometric techniques, phenolic compositions in crude extract were elucidated as followings: gallic acid (28.6%), HHDP hexose ester isomers (Ⅹ14.3%,Ⅻ11.6%), HHDP alkyl derivatives (Ⅴ4.1%,Ⅳ1.7%), methyl gallate (3.8%), brevifolin-carboxylic acid (3.2%), isocorilagin (3.1%), kaempferol-3-O-β-D-glucopyranoside (2.9%), 3-O-galloyl quinic acid butyl ester (2.6%), hyperin (2.3%), phenolic acid with Mw 348 (Ⅰ2.1%), 3,3′-dimethoxy-2,2′,4,4′-tetrahydroxy- diphenylformic acid (1.5%), ethyl gallate (1.3%), amentoflavone (1.1%) and sinapic acid (0.6%). Among them, 3-O-galloyl quinic acid butyl ester was one new phenolic compound, remaining compounds except gallic acid and hyperin were first identified in C. album
引文
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