杨梅渣中抗氧化活性成分的分离纯化及其结构鉴定研究
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摘要
杨梅,为杨梅科杨梅属植物,是我国的特产水果之一,栽培面积占全世界的99%以上,其中浙江省的栽培面积、产量、品种与品质均居全国之首。目前以杨梅为资源的食品工业已初具规模,然而在杨梅深加工过程中,杨梅渣都作为废物进行处理,对其开发利用仍然一片空白。基于此,本文以杨梅渣为研究对象,主要针对其化学成分进行研究,从中共分离得到了7个化合物,并通过紫外、质谱、核磁共振谱鉴定了它们的结构,其中2个(化合物1和化合物6)为首次从杨梅属植物中分离得到,并对部分单体物质进行了抗氧化活性研究。
1、杨梅属植物研究概况。通过文献综述,概括了杨梅属植物的化学成分和药理方面的研究进展,为杨梅属植物进一步研究提供根据。
2、对杨梅渣中化合物进行提取、浓缩、萃取,分成四个级分(石油醚相、乙酸乙酯相、正丁醇相和水相)；用DPPH法、Fenton反应法和还原能力评价了四相的体外抗氧化能力。结果表明,乙酸乙酯相和正丁醇相具有较强的清除DPPH自由基能力,其半抑制浓度(IC50)分别为53μg/mL、75μg/mL,分别是VC(IC50=110μg/mL的1.83倍、1.30倍。
3、杨梅渣的乙酸乙酯相采用正相硅胶柱色谱、Sephadex LH-20和制备型HPLC等方法分离,从中分离得到五个化合物,分别鉴定为：cabraleone(化合物1)、槲皮素(化合物2)、柠檬酸(化合物3)、杨梅素3-O-α-L-鼠李吡喃糖苷(化合物4)、槲皮素-3-0-β-L-鼠李吡喃糖苷(化合物5)。
4、杨梅渣的正丁醇相采用HSCCC进行初步分离,溶剂系统为：乙酸乙酯-正丁醇-水=4：1：5,得到B1和B2组分。B1组分通过Sephadex LH-20分离得到新橙皮苷(化合物6)；B2组分通过Sephadex LH-20分离得到正丁基-p-D-吡喃果糖苷(化合物7)。
5、杨梅渣中单体物质的体外抗氧化活性研究：采用DPPH-法对分离得到的部分单体物质进行了体外抗氧化活性试验。结果表明,化合物4和化合物5清除能力(IC50=0.38μg/mL、0.58μg/mL),分别是VE(IC50=2.32μg/mL)的6.11倍和4.00倍；化合物2在浓度为25.0μg/mL时,已经超过了94%,均远大于VE、化合物4和化合物5,均表现出很好的抗氧化作用。
本研究的结果为进一步阐明杨梅中的化学成分及其生物活性奠定了一定的基础。
Myrica rubra Sieb.et Zucc., belonging to Myricaceae family, is a specific fruit species in China. The cultivated area of Myrica rubra in China is more than 99% in the world, including Zhejiang Province, where the cultivated area, yield, variety and quality rank first in China. At present, the food industry based on Myrica rubra resources has a certain scale, while the utilization of Myrica rubra marc is still blank. Therefore, Myrica rubra marc were chemically studied in our research project for serching for bioactivities compounds.7 compounds were isolated and purified from Myrica rubra marc. Their structures were determined by UV, MS and NMR analysis, respectively. Two (compound 1 and compound 6) of them are isolated from this family for the first time. In addition, anti-oxidation activities of some of the compounds had completed.
1. The chemical composition and the pharmacological actions of components from Myricaceae were reviewed, which can provide the guideline for the research of Myricaceae.
2. Four fractions were acquired from Myrica rubra marc by a series of steps including extraction and concentration, followed by extraction with petroleum ether, ethyl acetate and n-butanol. The anti-oxidative activities of the extracts were evaluated in vitro, including DPPH radical scavenging activity, Fenton action and reducing power methods. The results showed that ethyl acetate fraction and n-butanol fraction of Myrica rubra marc crude extracts exhibited strong scavenging abilities for DPPH free radical, and their half-inhibitory concentration (IC50) were 53μg/mL and 75μg/mL, respectively, which were approximately 1.83 times and 1.30 times as much as that of Vitamin C (97μg/mL).
3. The chemical constituents in the ethyl acetate extract of Myrica rubra marc were separated by chromatography on silica gel, Sephadex LH-20 and Pre-HPLC to yield five compounds:cabraleone(compound 1), quercetin(compound 2), citric acid(compound 3), myricetin 3-O-α-L-rhamnopyranoside(compound 4) and quercetin 3-O-β-L-rhamnopyranoside(compound 5).
4. The chemical constituent in the n-butanol extract of Myrica rubra marc was isolated by HSCCC, with the solvent system of ethyl acetate-n-butanol-water=4:1:5. And then, B1 and B2 were acquired. The fraction B1 was isolated by Sephadex LH-20 to obtain neohesperidin (compound 6). The fraction B2 was isolated by Sephadex LH-20 to obtain n-butyl-β-D-fructopyranoside(compound 7).
5. Reserch on anti-oxidation of some of compouds from Myrica rubra marc:
DPPH radical scavenging activity had been done to ecaluate anti-oxidation of some of the compouds isolated from Myrica rubra marc. The results showed that the scavenging capacity of compound 4 (IC50=0.38μg/mL) and compound 5 (IC50=0.58μg/mL) are 6.11 times and 4.00 times as that of VE respectively, and compoud 2 is already more than 94% when the concentration is 25.0μg/mL, which is much stronger than Vitamin E, compoud 4 and compoud 5. It is concluded that they showed good antioxidant activities.
The results of present study will be useful to further phytochemical investigation on Myrica rubra.
1、杨梅属植物研究概况。通过文献综述,概括了杨梅属植物的化学成分和药理方面的研究进展,为杨梅属植物进一步研究提供根据。
2、对杨梅渣中化合物进行提取、浓缩、萃取,分成四个级分(石油醚相、乙酸乙酯相、正丁醇相和水相)；用DPPH法、Fenton反应法和还原能力评价了四相的体外抗氧化能力。结果表明,乙酸乙酯相和正丁醇相具有较强的清除DPPH自由基能力,其半抑制浓度(IC50)分别为53μg/mL、75μg/mL,分别是VC(IC50=110μg/mL的1.83倍、1.30倍。
3、杨梅渣的乙酸乙酯相采用正相硅胶柱色谱、Sephadex LH-20和制备型HPLC等方法分离,从中分离得到五个化合物,分别鉴定为：cabraleone(化合物1)、槲皮素(化合物2)、柠檬酸(化合物3)、杨梅素3-O-α-L-鼠李吡喃糖苷(化合物4)、槲皮素-3-0-β-L-鼠李吡喃糖苷(化合物5)。
4、杨梅渣的正丁醇相采用HSCCC进行初步分离,溶剂系统为：乙酸乙酯-正丁醇-水=4：1：5,得到B1和B2组分。B1组分通过Sephadex LH-20分离得到新橙皮苷(化合物6)；B2组分通过Sephadex LH-20分离得到正丁基-p-D-吡喃果糖苷(化合物7)。
5、杨梅渣中单体物质的体外抗氧化活性研究：采用DPPH-法对分离得到的部分单体物质进行了体外抗氧化活性试验。结果表明,化合物4和化合物5清除能力(IC50=0.38μg/mL、0.58μg/mL),分别是VE(IC50=2.32μg/mL)的6.11倍和4.00倍；化合物2在浓度为25.0μg/mL时,已经超过了94%,均远大于VE、化合物4和化合物5,均表现出很好的抗氧化作用。
本研究的结果为进一步阐明杨梅中的化学成分及其生物活性奠定了一定的基础。
Myrica rubra Sieb.et Zucc., belonging to Myricaceae family, is a specific fruit species in China. The cultivated area of Myrica rubra in China is more than 99% in the world, including Zhejiang Province, where the cultivated area, yield, variety and quality rank first in China. At present, the food industry based on Myrica rubra resources has a certain scale, while the utilization of Myrica rubra marc is still blank. Therefore, Myrica rubra marc were chemically studied in our research project for serching for bioactivities compounds.7 compounds were isolated and purified from Myrica rubra marc. Their structures were determined by UV, MS and NMR analysis, respectively. Two (compound 1 and compound 6) of them are isolated from this family for the first time. In addition, anti-oxidation activities of some of the compounds had completed.
1. The chemical composition and the pharmacological actions of components from Myricaceae were reviewed, which can provide the guideline for the research of Myricaceae.
2. Four fractions were acquired from Myrica rubra marc by a series of steps including extraction and concentration, followed by extraction with petroleum ether, ethyl acetate and n-butanol. The anti-oxidative activities of the extracts were evaluated in vitro, including DPPH radical scavenging activity, Fenton action and reducing power methods. The results showed that ethyl acetate fraction and n-butanol fraction of Myrica rubra marc crude extracts exhibited strong scavenging abilities for DPPH free radical, and their half-inhibitory concentration (IC50) were 53μg/mL and 75μg/mL, respectively, which were approximately 1.83 times and 1.30 times as much as that of Vitamin C (97μg/mL).
3. The chemical constituents in the ethyl acetate extract of Myrica rubra marc were separated by chromatography on silica gel, Sephadex LH-20 and Pre-HPLC to yield five compounds:cabraleone(compound 1), quercetin(compound 2), citric acid(compound 3), myricetin 3-O-α-L-rhamnopyranoside(compound 4) and quercetin 3-O-β-L-rhamnopyranoside(compound 5).
4. The chemical constituent in the n-butanol extract of Myrica rubra marc was isolated by HSCCC, with the solvent system of ethyl acetate-n-butanol-water=4:1:5. And then, B1 and B2 were acquired. The fraction B1 was isolated by Sephadex LH-20 to obtain neohesperidin (compound 6). The fraction B2 was isolated by Sephadex LH-20 to obtain n-butyl-β-D-fructopyranoside(compound 7).
5. Reserch on anti-oxidation of some of compouds from Myrica rubra marc:
DPPH radical scavenging activity had been done to ecaluate anti-oxidation of some of the compouds isolated from Myrica rubra marc. The results showed that the scavenging capacity of compound 4 (IC50=0.38μg/mL) and compound 5 (IC50=0.58μg/mL) are 6.11 times and 4.00 times as that of VE respectively, and compoud 2 is already more than 94% when the concentration is 25.0μg/mL, which is much stronger than Vitamin E, compoud 4 and compoud 5. It is concluded that they showed good antioxidant activities.
The results of present study will be useful to further phytochemical investigation on Myrica rubra.
引文
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