油用牡丹籽饼粕单萜苷的分离、纯化及结构鉴定
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摘要
油用牡丹榨油后的籽饼粕含有大量具有多种生物活性的单萜苷类化学成分,有重要的研究开发价值。本文采用硅胶、凝胶柱色谱以及半制备高效液相色谱等技术对油用牡丹籽饼粕中的单萜苷类化合物进行分离纯化,得到7个单萜苷类化合物。综合运用多种波谱学方法对分离得到的单萜苷类化合物的结构进行鉴定。分离得到的7个化合物分别鉴定为芍药苷(1)、氧化芍药苷(2)、4-甲氧基芍药苷(3)、4-甲氧基氧化芍药苷(4)、吡啶芍药苷(5)、8-O-去苯甲酰芍药苷(6)、oxypaeonidanin (7)。上述7个化合物均为首次从紫斑牡丹榨油后的牡丹籽饼粕中分离得到。结果表明油用牡丹籽饼粕中含有大量的单萜苷类化合物,具有重要的研究开发价值。
The seed cake of oil peony is rich in monoterpene glucosides with many biologically active, and hashigher utilization value. In this paper, seven monoterpene glucosides were isolated from the seed cake of Paeonia rockii by repeated column chromatography on silica gel, Sephadex LH-20 and semi-preparative-HPLC. The chemical constituents of the isolated compounds were elucidated by spectroscopic methods. The seven compounds were identified as paeoniflorin(1), oxypaeoniflorin(2), 4-O-methyl-paeoniflorin(3), 4-O-methyl-oxypaeoniflorin(4), pyrindylpaeoniflorin(5), 8-O-debenzoylpaeoniflorin(6), oxypaeonidanin(7). All these compounds are isolated from the seed cake of Paeonia rockii. These compounds and their derivatives are of significant interest for drug research and development. The study provides important evidence supporting for the exploitation of the seed cake of Paeonia rockii.
The seed cake of oil peony is rich in monoterpene glucosides with many biologically active, and hashigher utilization value. In this paper, seven monoterpene glucosides were isolated from the seed cake of Paeonia rockii by repeated column chromatography on silica gel, Sephadex LH-20 and semi-preparative-HPLC. The chemical constituents of the isolated compounds were elucidated by spectroscopic methods. The seven compounds were identified as paeoniflorin(1), oxypaeoniflorin(2), 4-O-methyl-paeoniflorin(3), 4-O-methyl-oxypaeoniflorin(4), pyrindylpaeoniflorin(5), 8-O-debenzoylpaeoniflorin(6), oxypaeonidanin(7). All these compounds are isolated from the seed cake of Paeonia rockii. These compounds and their derivatives are of significant interest for drug research and development. The study provides important evidence supporting for the exploitation of the seed cake of Paeonia rockii.
引文
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[16]BRACA A,KIEM P V,YEN P H,et al.New monoterpene glycosides from Paeonia lactiflora[J].Fitoterapia,2008,79(2):117-120.
[17]DING L Q,ZHAO F,CHEN L X,et al.New monoterpene glycosides from Paeonia suffruticosa Andrews and their inhibition on NO production in LPS-induced RAW 264.7 cells[J].Bioorganic&Medicinal Chemistry Letters,2012,22(23):7243-7247.
[18]杨素珍,蒋建勤.新疆芍药的化学成分研究[J].中草药,2014,4(6):760-764.
[2]邓瑞雪,刘振,秦琳琳,等.超临界CO2流体提取洛阳牡丹籽油工艺研究[J].食品科学,2010,31(10):142-145.
[3]史国安,郭香凤,金宝磊,等.牡丹籽油超临界CO2萃取工艺优化及抗氧化活性的研究[J].中国粮油学报,2013,28(4):47-50.
[4]王昌涛,张萍,董银卯.超临界CO2提取牡丹籽油的工艺以及成分分析[J].中国粮油学报,2009,24(8):96-99.
[5]LIU P,ZHANG Y,GAO J Y,et al.HPLC-DAD analysis of 15 monoterpene glycosides in oil peony seed cakes sourced from different cultivation areas in China[J].Industrial Crops and Products,2018,118:259-270.
[6]WU S H,WU D G,CHEN Y W.Chemical constituents and bioactivities of plants from the Genus paeonia[J].Chemistry&Biodiversity,2010,7(7):90-104.
[7]HE C N,PENG Y,ZHANG Y C,et al.Phytochemical and Biological Studies of Paeoniaceae[J].Chemistry&Biodiversity,2010,7(7):805-838.
[8]何春年,肖伟,李敏,等.牡丹种子化学成分研究[J].中国中药杂志,2010,35(11):1428-1431.
[9]HE C N,ZHANG Y C,XIAO P G,et al.Monoterpene glycosides from the seeds of Paeonia suffruticosa protect HEK 293 cells from irradiation-induced DNA damage[J].Phytochemistry Letters,2012,5(1):128-133.
[10]刘普,李小方,张恒,等.RP-HPLC测定油用牡丹籽饼粕和籽壳中单萜苷的含量[J].中国粮油学报,2016,31(10):142-145.
[11]刘普,李亮,邓瑞雪,等.凤丹籽饼粕单萜苷类成分的研究[J].中国药学杂志,2013,48(17):1445-1448.
[12]刘普,卢宗元,邓瑞雪,等.凤丹牡丹籽饼粕中的一个新单萜苷[J].中国药学杂志,2014,49(5):360-362.
[13]吴英华,任凤莲,蔡小华,等.紫外分光光度法测定白芍总苷的含量[J].应用化工,2007,36(8):822-824.
[14]王瑞,侴桂新,朱恩圆,等.川赤芍化学成分研究[J].中国药学杂志,2007,42(9):661-663.
[15]周秋香,李友宾,蒋建勤.白芍的化学成分研究[J].海峡药学,2009,21(6):92-94.
[16]BRACA A,KIEM P V,YEN P H,et al.New monoterpene glycosides from Paeonia lactiflora[J].Fitoterapia,2008,79(2):117-120.
[17]DING L Q,ZHAO F,CHEN L X,et al.New monoterpene glycosides from Paeonia suffruticosa Andrews and their inhibition on NO production in LPS-induced RAW 264.7 cells[J].Bioorganic&Medicinal Chemistry Letters,2012,22(23):7243-7247.
[18]杨素珍,蒋建勤.新疆芍药的化学成分研究[J].中草药,2014,4(6):760-764.