金柑等柑橘类果实黄酮类化合物提取、纯化及分离鉴定
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摘要
金柑目前主要以果实鲜食为主,而果实加工副产品果皮及栽培管理过程中疏除的落果和裂果,很多地方都作为废弃物丢弃,未能加以充分利用。金柑富含黄酮类化合物、色素、香精油等活性成分。近年研究表明金柑黄酮有恢复免疫力、抗氧化、抗菌、调节血糖含量和改善糖耐量等作用。本文福建尤溪采集金弹(Fortunella crassifolia Swing)鲜果为材料,对金柑不同品种、器官和不同生长发育期金柑果实的黄酮和酚酸含量进行分析和研究的基础上,系统研究其果皮黄酮类化合物提取纯化工艺,利用高速逆流方法分离制备2个黄酮类单体,旨在为金柑资源的综合利用提供技术支持。主要研究结果如下:
1、金柑果实黄酮和酚酸的HPLC检测体系建立
建立了金柑果实中11种黄酮和酚酸的分析测定方法。采用Merck Lichrspher-100RP18e柱(250mm×4.0 mm,5μm)分离样品,以2%乙酸-乙腈为流动相,梯度洗脱,流速为0.8mL/min,检测波长为280nm,柱温30℃,进样量10μL,结果显示金柑中的11种果实黄酮和酚酸达到完全分离,线性范围为1~50μg/mL,平均回收率在90.7%~99.84%。
2、不同柑橘品种黄酮含量研究
选择了27个具有代表型的柑橘品种(包括8种宽皮橘、2个杂交品种、8种柚、6种金柑、2种甜橙、1种枳实)果皮和20个品种的果肉黄酮和酚酸含量进行研究。研究结果表明:红肉蜜柚和文旦柚果皮中柚皮苷含量高;温州蜜柑、南丰蜜桔和芦柑适合果皮中橙皮苷提取,含量达到66mg/g以上;枳实是中国传统的中药其中含有丰富的酚酸和槲皮素,是提取酚酸和槲皮素中药的原料。胡柚果肉中富含咖啡酸、香豆酸、芥子酸和芦丁,温州蜜柑芥子酸和橙皮苷含量高,金柑果肉含有丰富的槲皮素和山奈酚。胡柚和温州蜜柑有很高的营养价值,多食金柑有利于黄酮醇的补充。
27个柑橘品种可依据果皮中的黄酮和酚酸含量为指标,依据欧氏距离,归为分为柚、金柑、宽皮橘三个大组,枳实、强得勒和茂谷桔橙杂交品种遗传背景较为复杂单独为一组。金柑属品种间的相似度高,而与其他的品种黄酮和酚酸的含量差异很大。
3、金柑果实不同生长发育期酚酸和黄酮的研究
运用HPLC方法测定不同生长发育期金柑果实中黄酮和酚酸含量。结果表明:随着成熟度的增加,花后45天~65天金柑果实中黄酮和酚酸含量随着成熟度的增加而急剧减少,花后85天左右变化平缓,到接近成熟的花后125天左右,黄酮和酚酸含量又小幅上升后下降;果皮中黄酮和酚酸的含量大于果肉;金柑幼果适合于提取槲皮素和橙皮苷。
4、金柑果皮总黄酮提取工艺研究
利用酶提取法和超声波辅助提取法对金柑果皮黄酮类物质进行提取分离纯化:酶辅助提取的最佳工艺条件为:70%乙醇,酶用量75 U/mL,料液比1:35,温度50℃,提取时间100 min,提取率达1.39%,平均回收率99.4%。超声波提取的最佳工艺条件为:温度为30℃,乙醇浓度60%,料液比为1:50,超声功率450w,超声时间25 min,取率为1.51%,提取的回收率为98.3%。
5、金柑果皮总黄酮纯化工艺研究
通过对X-5、NKA-9、AB-8、NKA、S-8、HPD-300和HPD-600等7种树脂静态吸附和解析性能的对比,选择吸附和洗脱性能都好AB-8大孔树脂,进行吸附条件的优化。确定金柑果皮总黄酮纯化最佳条件为:吸附时间3h,60%乙醇,解吸液体积与树脂质量比20:1,解吸时间2.5h,回收率为79.1%。对纯化后的金柑皮黄酮进行分析,通过UV光谱定性后,用质谱鉴定出金柑果皮黄酮成分主要为芹菜素-6-C-芸香糖苷、根皮素-3',5'-2-C-β-吡喃葡糖苷、刺槐素-8-C-芸香糖苷和山奈酚-3-O芸香糖苷-7-O葡萄糖,而最主要的成分为根皮素-3',5'-2-C-β-吡喃葡糖苷。
6、金柑果皮正丁醇相提取物分离
首次采用HSCCC技术分离金柑正丁醇相提取物,以石油醚∶正丁醇∶水(1∶2∶3,V/V)为溶剂系统,上相为固定相,下相为流动相,在转速850 rpm/min下,进样量30mg,流速为1 mL/min,从金柑皮中分离得到2个化合物,经过高效液相色谱鉴定其纯度为90.8%和93.2%,运用LC-ESI-MS确定化合物的分子量为598.2和592.3,推测其物质为根皮素-3',5' -2-C -β-吡喃葡糖苷和刺槐素-8-C-芸香糖苷。
Fortunella crassifolia Swing has been used in folk medicine in China and recently more attempts have been made to study the pharmacological activities of some bioactive compounds isolated from kumquat.Recently the flavonoids of Fortunella crassifolia Swing are shown to have antioxidative activity,free radical scavenging capacity, antimicrobial activity and some other activities. In this paper, Fortunella crassifolia Swing fruit was carried out.Flavonoids and phenolic acids in different cultivars' fruits and different developing stage fruits were also analysed. The technological conditions of purification of flavonoids from the peel of Fortunella crassifolia Swing were studied. Then two flavonoids were isolated by HSCCC. The results were summarized as follows:
1 Establish the method of analyse 11 flavonoids and phenolic acids compounds HPLC.
The analysis was performed on Merck Lichrospher-100RP18e(250mm×4.0 mm,5μm)column with mobile phase contained acetic acid (2%) -. acetonitrile.The flow rate was 0.8 mL·min-1 and the detection wavelength was set at 280 nm. The temperature of column was 30℃and the injected volume was 10μL. Under this condition, 11 could be completely separated. The lined range of four flavonoids was 1~50μg, respectively. The average recovery of four flavoniods was 90.70%.~99.84%.The method is fast, simple, accurate and reliable which can be applied to the quality control of kumquat.
2 Composition and Distribution of flavonoids and Phenolic Acids in fruits of different cultivars
27 cultivars of mandarin,common oranges ,kumquats,oranges, Frutus aurantii and Pomelo groups have been analysed for its content in flavonoids and phenolic acids from its fruits.
The results showed that The Red-fleshed Sweet Pomelo and Wendun pummelo has obvious differences in the naringin content.The hesperidin content of Satsume、Nan Feng Mandarin and Ponkan were above 66mg/g. For large content of phenolic acid and quercetin ,Citrus aurantium was suitable for extracting them.The flesh of Huyou had large content of caffeic acid ,coumaric acid,sinapic acid and lutin. The flesh of Satsume also has a large content of sinapc acid and hesperidin.Fortunella crassifolia Swing has a large con tent of quercetin and kaempferol.So Huyou , Fortunella crassifolia Swing ,and Satsume is high in nutritional value.
Based on the contents of 11 compounds,the 27 cultivars were divied to kumquat, Pummelo and mandarin orange .Murcott Chandler Pummelo and Poncirus tuifoliata (L.)Raf. is a group. The classification of Murcott and Chandler Pummelo was inconsistent with the traditional classification. These species which belonged to Fortunella crassifolia Swing was very close with each other and it meaned that it have ordinary backgrand in heredity. The flavonoids and the phenolic acids content of other variety was difference.
3 Composition and Distribution of flavonoids and Phenolic Acids in fruits during growth
The contents of flavonoids and phenolic acids in fiuits of different developing stage were obtained by HPLC.The results showed that of contents of flavonoids and phenolic acids in fruits of 45 to 65 days after anthesis decreased sharply,decreaseed slowly 85 days after anthesis.The contents of 125 days after anthesis is much increasing.While that in peel had the highest content at half ripe stage, and contents of flavonoids and phenolic acids in peel were much higher than that in flesh.Because of high content of hesperidin and quercetin,young fruits of Fortunella crassifolia Swingwas suitable for extracting them.
4 Extraction of total flavonoids from the peel of Fortunella crassifolia Swing
. Under the optimized conditions of Ultrasonic-assisted Extraction as follows:ultrasonic power 500w, tempreture 30℃,60% ethanol as the extraction solvent,material/liquid ratio1:50,and extraction time 25min,a yield of flavonoids of 1.51% was achieved. Optimum conditions of enzyme extract for the optimum temperature is 50℃, 70% ethanol concentration, solid to liquid ratio of 1:35, enzyme concentration 0.5%, extraction time 100min, can achieve the best extraction effect.
5 Purification of total flavonoids from the peel of Fortunella crassifolia Swing
The absorption and desorption properties of seven kinds of macroporous resin (x-5, NKA-9, AB-8,NKA,S-8,HPD-300 and HPD-600). Senven resins screened , AB-8 was the best type to extract flavonoids from the peels of Fortunella crassifolia Swing. On the conditions of crude flavonoids solution adsorption time 3 h, ratio of 60 % ethanol (desorption solution) volume to the resin weight 20:1 and desorption time 2.5 h, the recovery rate of the flavonoids is 79.1 %. The structures of trace amount of unknown flavonoid
s were deduced based on the spectra of known compounds.They were proposed to be .Phloretin 3′,5′-di-C-β-glycopyranoside,Apigenin 6-C-rutinoside,Acacetin 8-C-rutinoside and kaempferol-3,7-O-diglucoside。
6 Isolation and preparation of flavones in butanol extract from the peel of Fortunella crassifolia Swing
High-speed counter-current chromatography(HSCCC) was successfully applied to the preparative separation of pumpkin ethyl acetate extraction using two-phase solvent system composed of petroleum ether-n-butyl alcohol-H2O (1:2:3,w/w) with the flow rate of 1 mL/min and the rotation rate of 850 r/min. Compounds Phloretin 3′,5′-di-C-β-glycopyranoside and Acacetin 8-C-rutinoside were 90.8% , 93.2%determined by HPLC.
1、金柑果实黄酮和酚酸的HPLC检测体系建立
建立了金柑果实中11种黄酮和酚酸的分析测定方法。采用Merck Lichrspher-100RP18e柱(250mm×4.0 mm,5μm)分离样品,以2%乙酸-乙腈为流动相,梯度洗脱,流速为0.8mL/min,检测波长为280nm,柱温30℃,进样量10μL,结果显示金柑中的11种果实黄酮和酚酸达到完全分离,线性范围为1~50μg/mL,平均回收率在90.7%~99.84%。
2、不同柑橘品种黄酮含量研究
选择了27个具有代表型的柑橘品种(包括8种宽皮橘、2个杂交品种、8种柚、6种金柑、2种甜橙、1种枳实)果皮和20个品种的果肉黄酮和酚酸含量进行研究。研究结果表明:红肉蜜柚和文旦柚果皮中柚皮苷含量高;温州蜜柑、南丰蜜桔和芦柑适合果皮中橙皮苷提取,含量达到66mg/g以上;枳实是中国传统的中药其中含有丰富的酚酸和槲皮素,是提取酚酸和槲皮素中药的原料。胡柚果肉中富含咖啡酸、香豆酸、芥子酸和芦丁,温州蜜柑芥子酸和橙皮苷含量高,金柑果肉含有丰富的槲皮素和山奈酚。胡柚和温州蜜柑有很高的营养价值,多食金柑有利于黄酮醇的补充。
27个柑橘品种可依据果皮中的黄酮和酚酸含量为指标,依据欧氏距离,归为分为柚、金柑、宽皮橘三个大组,枳实、强得勒和茂谷桔橙杂交品种遗传背景较为复杂单独为一组。金柑属品种间的相似度高,而与其他的品种黄酮和酚酸的含量差异很大。
3、金柑果实不同生长发育期酚酸和黄酮的研究
运用HPLC方法测定不同生长发育期金柑果实中黄酮和酚酸含量。结果表明:随着成熟度的增加,花后45天~65天金柑果实中黄酮和酚酸含量随着成熟度的增加而急剧减少,花后85天左右变化平缓,到接近成熟的花后125天左右,黄酮和酚酸含量又小幅上升后下降;果皮中黄酮和酚酸的含量大于果肉;金柑幼果适合于提取槲皮素和橙皮苷。
4、金柑果皮总黄酮提取工艺研究
利用酶提取法和超声波辅助提取法对金柑果皮黄酮类物质进行提取分离纯化:酶辅助提取的最佳工艺条件为:70%乙醇,酶用量75 U/mL,料液比1:35,温度50℃,提取时间100 min,提取率达1.39%,平均回收率99.4%。超声波提取的最佳工艺条件为:温度为30℃,乙醇浓度60%,料液比为1:50,超声功率450w,超声时间25 min,取率为1.51%,提取的回收率为98.3%。
5、金柑果皮总黄酮纯化工艺研究
通过对X-5、NKA-9、AB-8、NKA、S-8、HPD-300和HPD-600等7种树脂静态吸附和解析性能的对比,选择吸附和洗脱性能都好AB-8大孔树脂,进行吸附条件的优化。确定金柑果皮总黄酮纯化最佳条件为:吸附时间3h,60%乙醇,解吸液体积与树脂质量比20:1,解吸时间2.5h,回收率为79.1%。对纯化后的金柑皮黄酮进行分析,通过UV光谱定性后,用质谱鉴定出金柑果皮黄酮成分主要为芹菜素-6-C-芸香糖苷、根皮素-3',5'-2-C-β-吡喃葡糖苷、刺槐素-8-C-芸香糖苷和山奈酚-3-O芸香糖苷-7-O葡萄糖,而最主要的成分为根皮素-3',5'-2-C-β-吡喃葡糖苷。
6、金柑果皮正丁醇相提取物分离
首次采用HSCCC技术分离金柑正丁醇相提取物,以石油醚∶正丁醇∶水(1∶2∶3,V/V)为溶剂系统,上相为固定相,下相为流动相,在转速850 rpm/min下,进样量30mg,流速为1 mL/min,从金柑皮中分离得到2个化合物,经过高效液相色谱鉴定其纯度为90.8%和93.2%,运用LC-ESI-MS确定化合物的分子量为598.2和592.3,推测其物质为根皮素-3',5' -2-C -β-吡喃葡糖苷和刺槐素-8-C-芸香糖苷。
Fortunella crassifolia Swing has been used in folk medicine in China and recently more attempts have been made to study the pharmacological activities of some bioactive compounds isolated from kumquat.Recently the flavonoids of Fortunella crassifolia Swing are shown to have antioxidative activity,free radical scavenging capacity, antimicrobial activity and some other activities. In this paper, Fortunella crassifolia Swing fruit was carried out.Flavonoids and phenolic acids in different cultivars' fruits and different developing stage fruits were also analysed. The technological conditions of purification of flavonoids from the peel of Fortunella crassifolia Swing were studied. Then two flavonoids were isolated by HSCCC. The results were summarized as follows:
1 Establish the method of analyse 11 flavonoids and phenolic acids compounds HPLC.
The analysis was performed on Merck Lichrospher-100RP18e(250mm×4.0 mm,5μm)column with mobile phase contained acetic acid (2%) -. acetonitrile.The flow rate was 0.8 mL·min-1 and the detection wavelength was set at 280 nm. The temperature of column was 30℃and the injected volume was 10μL. Under this condition, 11 could be completely separated. The lined range of four flavonoids was 1~50μg, respectively. The average recovery of four flavoniods was 90.70%.~99.84%.The method is fast, simple, accurate and reliable which can be applied to the quality control of kumquat.
2 Composition and Distribution of flavonoids and Phenolic Acids in fruits of different cultivars
27 cultivars of mandarin,common oranges ,kumquats,oranges, Frutus aurantii and Pomelo groups have been analysed for its content in flavonoids and phenolic acids from its fruits.
The results showed that The Red-fleshed Sweet Pomelo and Wendun pummelo has obvious differences in the naringin content.The hesperidin content of Satsume、Nan Feng Mandarin and Ponkan were above 66mg/g. For large content of phenolic acid and quercetin ,Citrus aurantium was suitable for extracting them.The flesh of Huyou had large content of caffeic acid ,coumaric acid,sinapic acid and lutin. The flesh of Satsume also has a large content of sinapc acid and hesperidin.Fortunella crassifolia Swing has a large con tent of quercetin and kaempferol.So Huyou , Fortunella crassifolia Swing ,and Satsume is high in nutritional value.
Based on the contents of 11 compounds,the 27 cultivars were divied to kumquat, Pummelo and mandarin orange .Murcott Chandler Pummelo and Poncirus tuifoliata (L.)Raf. is a group. The classification of Murcott and Chandler Pummelo was inconsistent with the traditional classification. These species which belonged to Fortunella crassifolia Swing was very close with each other and it meaned that it have ordinary backgrand in heredity. The flavonoids and the phenolic acids content of other variety was difference.
3 Composition and Distribution of flavonoids and Phenolic Acids in fruits during growth
The contents of flavonoids and phenolic acids in fiuits of different developing stage were obtained by HPLC.The results showed that of contents of flavonoids and phenolic acids in fruits of 45 to 65 days after anthesis decreased sharply,decreaseed slowly 85 days after anthesis.The contents of 125 days after anthesis is much increasing.While that in peel had the highest content at half ripe stage, and contents of flavonoids and phenolic acids in peel were much higher than that in flesh.Because of high content of hesperidin and quercetin,young fruits of Fortunella crassifolia Swingwas suitable for extracting them.
4 Extraction of total flavonoids from the peel of Fortunella crassifolia Swing
. Under the optimized conditions of Ultrasonic-assisted Extraction as follows:ultrasonic power 500w, tempreture 30℃,60% ethanol as the extraction solvent,material/liquid ratio1:50,and extraction time 25min,a yield of flavonoids of 1.51% was achieved. Optimum conditions of enzyme extract for the optimum temperature is 50℃, 70% ethanol concentration, solid to liquid ratio of 1:35, enzyme concentration 0.5%, extraction time 100min, can achieve the best extraction effect.
5 Purification of total flavonoids from the peel of Fortunella crassifolia Swing
The absorption and desorption properties of seven kinds of macroporous resin (x-5, NKA-9, AB-8,NKA,S-8,HPD-300 and HPD-600). Senven resins screened , AB-8 was the best type to extract flavonoids from the peels of Fortunella crassifolia Swing. On the conditions of crude flavonoids solution adsorption time 3 h, ratio of 60 % ethanol (desorption solution) volume to the resin weight 20:1 and desorption time 2.5 h, the recovery rate of the flavonoids is 79.1 %. The structures of trace amount of unknown flavonoid
s were deduced based on the spectra of known compounds.They were proposed to be .Phloretin 3′,5′-di-C-β-glycopyranoside,Apigenin 6-C-rutinoside,Acacetin 8-C-rutinoside and kaempferol-3,7-O-diglucoside。
6 Isolation and preparation of flavones in butanol extract from the peel of Fortunella crassifolia Swing
High-speed counter-current chromatography(HSCCC) was successfully applied to the preparative separation of pumpkin ethyl acetate extraction using two-phase solvent system composed of petroleum ether-n-butyl alcohol-H2O (1:2:3,w/w) with the flow rate of 1 mL/min and the rotation rate of 850 r/min. Compounds Phloretin 3′,5′-di-C-β-glycopyranoside and Acacetin 8-C-rutinoside were 90.8% , 93.2%determined by HPLC.
引文
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