苍耳子中咖啡酰奎宁酸类化学成分的研究
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摘要
目的研究苍耳子中的化学成分。方法采用硅胶柱色谱、ODS反相柱色谱、Sephadex LH-20、MCI gel CHP 20P和HPLC等色谱方法进行分离纯化,并结合质谱与现代波谱学技术鉴定化合物结构。结果从苍耳子70%乙醇提取物中乙酸乙酯萃取部位分离得到10个化合物,分别鉴定为咖啡酸(1)、咖啡酸甲酯(2)、咖啡酸乙酯(3)、5-O-咖啡酰基奎宁酸(4)、5-O-咖啡酰基奎宁酸甲酯(5)、3-O-咖啡酰基奎宁酸甲酯(6)、1,5-O-二咖啡酰基奎宁酸(7)、3,5-O-二咖啡酰基奎宁酸(8)、3,5-O-二咖啡酰基奎宁酸甲酯(9),3,4-O-二咖啡酰基奎宁酸甲酯(10)。结论本实验所测定数据与文献报道的基本一致。
Objective To study the chemical constituents in Cang'erzi(Xanthii Fructus). Methods The compounds were isolated and purified by silica gel column chromatography, ODS reversed-phase column chromatography, Sephadex LH-20, MCI gel CHP 20 P and HPLC methods. The structures of the compounds were identified by mass spectrometry and spectral analysis methods. Results Ten compounds were isolated from the ethyl acetate extract of 70% ethanol extract of Xanthii Fructus, which were identified as caffeic acid(1), caffeic acid methyl ester(2), caffeic acid ethyl ester(3), 5-O-caffeoylquinic acid(4), 5-O-caffeoylquinic acid methyl ester(5), 3-O-caffeoylquinic acid methyl ester(6), 1,5-di-O-caffeoylquinic acid(7), 3,5-di-O-caffeoylquinic acid(8), 3,5-di-O-caffeoylquinic acid methyl ester(9), 3,4-di-O-caffeoylquinic acid methyl ester(10). Conclusion The chemical constituents measured in this experiment are basically consistent with those reported in the literature.
Objective To study the chemical constituents in Cang'erzi(Xanthii Fructus). Methods The compounds were isolated and purified by silica gel column chromatography, ODS reversed-phase column chromatography, Sephadex LH-20, MCI gel CHP 20 P and HPLC methods. The structures of the compounds were identified by mass spectrometry and spectral analysis methods. Results Ten compounds were isolated from the ethyl acetate extract of 70% ethanol extract of Xanthii Fructus, which were identified as caffeic acid(1), caffeic acid methyl ester(2), caffeic acid ethyl ester(3), 5-O-caffeoylquinic acid(4), 5-O-caffeoylquinic acid methyl ester(5), 3-O-caffeoylquinic acid methyl ester(6), 1,5-di-O-caffeoylquinic acid(7), 3,5-di-O-caffeoylquinic acid(8), 3,5-di-O-caffeoylquinic acid methyl ester(9), 3,4-di-O-caffeoylquinic acid methyl ester(10). Conclusion The chemical constituents measured in this experiment are basically consistent with those reported in the literature.
引文
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[20]赵珊,张宝,熊丹丹,等.苗药黑骨藤的化学成分研究[J].中草药, 2017, 48(8):1513-1518.
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[22]CARNATA,HEITZA,FRAISSED,etal.Major dicaffeoylquinic acids from artemisia vulgaris[J]. Fitoterapia,2000, 71(5):587.
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[2]杨雪,张冰,高建超,等.毒性药材苍耳子的中医药古籍挖掘研究[J].中华中医药杂志, 2017(7):3085-3088.
[3]JIANG H, YANG L, MA G X, et al. New phenylpropanoid derivatives from the fruits of xanthium sibiricum and their anti-inflammatory activity[J]. Fitoterapia, 2017(117):11.
[4]张争名,余海忠,胡元.鄂西北产苍耳子甲醇粗提物抑菌活性及其清除DPPH能力的步评价[J].生物资源, 2011,33(3):43-45.
[5]邵海峰,胡晓梅,柴天川,等.苍耳子抗过敏有效部位的实验研究[J].四川中医, 2006, 24(8):25-26.
[6] JIANG H, MA G X, YANG L, et al. Rearranged ent-kauranoid glycosides from the fruits of xanthium strumarium, and their antiproliferative activity[J]. Phytochemistry Letters, 2016,18:192-196.
[7]苏新国,黄天来,王宁生.苍耳子的抗氧化成分研究[J].中药新药与临床药理, 2007, 18(1):47-49.
[8]胡冬燕,杨顺义,袁呈山,等.苍耳化学成分的分离与鉴定[J].中草药, 2012, 43(4):640-644.
[9]胡迪,王耀登,吴慧,等.苍耳子炒制前后挥发油和脂肪油成分GC-MS分析[J].湖北中医药大学学报, 2012, 14(6):29-31.
[10]黄文华,郭宝林,余竞光,等.中药苍耳子的化学成分研究[C]//全国中药和天然药物学术研讨会, 2003.
[11]杨柳,吴金雄,许舜军,等.苍耳子中酚酸类化合物的鉴别及绿原酸的含量测定[J].中国实验方剂学杂志,2011(19):85-88.
[12] JIANG H, YANG L, XING X, et al. HPLC-PDA combined with chemometrics for quantitation of active components and quality assessment of raw and processed fruits of xanthium strumarium L[J]. Molecules, 2018, 23(2):243.
[13] HAI J, LIU Y, XING X, et al. Development of an analytical method for separation of phenolic acids by ultraperformance convergence chromatography(UPC2)using a column packed with a sub-2-μm particle[J]. Journal of Pharmaceutical&Biomedical Analysis, 2018(153):117.
[14] JIANG H, YANG L, LIU C, et al. Four new glycosides from the fruit of xanthium sibiricum Patr[J]. Molecules, 2013,18(10):12464.
[15]姜海,张妍妍,张颖,等.苍耳子化学成分研究[J].中医药信息, 2016, 33(3):8-10.
[16]姜海,杨柳,邢绪东,等.苍耳子中木脂素类化学成分研究[J].中国中药杂志:1-13.
[17] CHEN Y H, CHANG F R, LIN Y J, et al. Identificatio n of phenolic antioxidants from sword brake fern(Pteris ensiformis Burm.)[J]. Food Chemistry, 2007, 105(1):48-56.
[18]乔灏祎,叶贤胜,赫军,等.山茱萸中一个新的环烯醚萜苷类化合物[J].中国药学杂志, 2017, 52(14):1212-1216.
[19]李阳,张春云,林挺,等.白花地胆草的化学成分研究[J].中国中药杂志, 2013, 38(11):1751-1756.
[20]赵珊,张宝,熊丹丹,等.苗药黑骨藤的化学成分研究[J].中草药, 2017, 48(8):1513-1518.
[21]马俊利,李宁,李铣.忍冬叶中咖啡酰奎宁酸类化学成分[J].中国中药杂志, 2009, 34(18):2346-2348.
[22]CARNATA,HEITZA,FRAISSED,etal.Major dicaffeoylquinic acids from artemisia vulgaris[J]. Fitoterapia,2000, 71(5):587.
[23]陈敏.灰毡毛忍冬化学成分研究[D].国家医药管理局上海医药工业研究院上海医药工业研究院, 1993.