枸杞根化学成分研究
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摘要
目的研究枸杞Lycium chinense根的化学成分。方法采用硅胶柱色谱、ODS开放柱色谱、Sephadex LH-20葡聚糖凝胶柱色谱及制备高效液相色谱等方法对化合物进行分离纯化,根据其理化性质及波谱数据鉴定化合物结构。结果从枸杞根部乙醇提取物的醋酸乙酯部位分离得到12个化合物,分别鉴定为大海米菊酰胺K(1)、grossamide(2)、dihydrogrossamide(3)、大麻酰胺H(4)、1,2-dihydro-6,8-dimethoxy-7-hydroxy-1-(3,4-dihydroxyphenyl)-N1,N2-bis[2-(4-hydroxyphenyl)ethyl]-2,3-naphthalene dicarboxamide(5)、大麻酰胺D(6)、(1,2-trans)-N3-(4-acetamidobutyl)-1-(3,4-dihydroxyphenyl)-7-hydroxy-N2-(4-hydroxyphenethyl)-6,8-dimethoxy-1,2-dihydronaphthalene-2,3-dicarboxamide(7)、大麻酰胺F(8)、(E)-2-(4,5-dihydroxy-2-{3-[(4-hydroxyphenethyl)amino]-3-oxopropyl}phenyl)-3-(4-hydroxy-3-methoxyphenyl)-N-(4-acetamidobutyl)acrylamide(9)、(E)-2-(4,5-dihydroxy-2-{3-[(4-hydroxyphenethyl)amino]-3-oxopropyl}phenyl)-3-(4-hydroxy-3,5-dimethoxyphenyl)-N-(4-hydroxyphenethyl)acrylamide(10)、(+)-南烛木树脂酚-3α-O-β-D-葡萄糖(11)、(-)-南烛木树脂酚-3α-O-β-D-葡萄糖(12)。结论化合物3为新天然产物,1、2、4~8为首次从该植物中分离得到。
Objective To study the chemical constituents from the roots of Lycium chinense. Methods The compounds were isolated and purified by silica gel, ODS and Sephadex LH-20 chromatography in addition to preparative-HPLC. Their structures were elucidated on the basis of physicochemical properties and spectral analysis. Results Twelve compounds were isolated from the Et OAc fraction of the root of Lycium chinense and identified as grossamide K(1), grossamide(2), dihydrogrossamide(3), cannabisin H(4), 1,2-dihydro-6,8-dimethoxy-7-hydroxy-1-(3,4-dihydroxyphenyl)-N1,N2-bis [2-(4-hydroxyphenyl)ethyl]-2,3-naphthalene dicarboxamide(5), cannabisin D(6),(1,2-trans)-N3-(4-acetamidobutyl)-1-(3,4-dihydroxyphenyl)-7-hydroxy-N2-(4-hydroxyphenethyl)-6,8-dimethoxy-1,2-dihydronaphthalene-2,3-dicarboxamide(7), cannabisin F(8),(E)-2-(4,5-dihydroxy-2-{3-[(4-hydroxyphenethyl)amino]-3-oxopropyl} phenyl)-3-(4-hydroxy-3-methoxyphenyl)-N-(4-acetamidobutyl)acrylamide(9),(E)-2-(4,5-dihydroxy-2-{3-[(4-hydroxylphenethyl) amino]-3-oxopropyl}phenyl)-3-(4-hydroxy-3,5-dimethoxyphenyl)-N-(4-hydroxyphenethyl)acrylamide(10),(+)-lyoniresinol-3α-O-β-Dglucopyranoside(11), and(-)-lyoniresinol-3α-O-β-D-glucopyranoside(12). Conclusion Compound 3 is a new natural product. Compounds 1, 2, and 4—8 are isolated from this plant for the first time.
Objective To study the chemical constituents from the roots of Lycium chinense. Methods The compounds were isolated and purified by silica gel, ODS and Sephadex LH-20 chromatography in addition to preparative-HPLC. Their structures were elucidated on the basis of physicochemical properties and spectral analysis. Results Twelve compounds were isolated from the Et OAc fraction of the root of Lycium chinense and identified as grossamide K(1), grossamide(2), dihydrogrossamide(3), cannabisin H(4), 1,2-dihydro-6,8-dimethoxy-7-hydroxy-1-(3,4-dihydroxyphenyl)-N1,N2-bis [2-(4-hydroxyphenyl)ethyl]-2,3-naphthalene dicarboxamide(5), cannabisin D(6),(1,2-trans)-N3-(4-acetamidobutyl)-1-(3,4-dihydroxyphenyl)-7-hydroxy-N2-(4-hydroxyphenethyl)-6,8-dimethoxy-1,2-dihydronaphthalene-2,3-dicarboxamide(7), cannabisin F(8),(E)-2-(4,5-dihydroxy-2-{3-[(4-hydroxyphenethyl)amino]-3-oxopropyl} phenyl)-3-(4-hydroxy-3-methoxyphenyl)-N-(4-acetamidobutyl)acrylamide(9),(E)-2-(4,5-dihydroxy-2-{3-[(4-hydroxylphenethyl) amino]-3-oxopropyl}phenyl)-3-(4-hydroxy-3,5-dimethoxyphenyl)-N-(4-hydroxyphenethyl)acrylamide(10),(+)-lyoniresinol-3α-O-β-Dglucopyranoside(11), and(-)-lyoniresinol-3α-O-β-D-glucopyranoside(12). Conclusion Compound 3 is a new natural product. Compounds 1, 2, and 4—8 are isolated from this plant for the first time.
引文
[1]中国科学院中国植物志编辑委员会.中国植物志[M].北京:科学出版社,2004.
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[8]李维波,王玲,邓学端,等.2型糖尿病患者红细胞脆性与异形率的观察及枸杞多糖对二者的影响[J].河北中医,2000,22(8):585-586.
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[13]Sakakibara I,Ikeya Y,Hayashi K,Mrrsuhashi H.Three phenyldihydronaphthalene lignanamides from fruits of Cannabis sativa[J].Phytochemistry,1992,31(9):3219-3223.
[14]Jing X Z,Shu H G,Rui H F,et al.Neolignanamides,lignanamides,and other phenolic compounds from the root bark of Lycium chinense[J].Nat Prod,2013,76(1):51-58.
[15]Sakakibara I,Ikeya Y,Hayashi K,et al.Three acyclic bis-phenylpropane lignanamides from fruits of Cannabissativa[J].Phytochemistry,1995,38(4):1003-1007.
[16]袁惠,付辉政,钟瑞建,等.枫香树叶的化学成分[J].中国实验方剂学杂志,2014,20(13):102-105.
[17]刘锐,庾石山,裴月湖,等.楹树叶的化学成分[J].中国中药杂志,2009,34(16):2063-2065.
[2]中国药典[S].一部.2015.
[3]Yao X,Peng Y,Xu L J,et al.Phytochemical and biological studies of Lycium medicinal plants[J].ChemBiodiver,2011,8(6):976-1010.
[4]侯学谦.枸杞化学成分及药理活性研究进展[J].海峡药学,2016,28(8):1-7.
[5]Miao Y,Xiao B X,Jiang Z,et al.Growth inhibition and cellcycle arrest of human gastric cancer cells by Lyciumbarbarum polysaccharide[J].Med Oncol,2010,27(3):785-790.
[6]Mao F,Xiao B X,Jiang Z,et al.Anticancer effect of Lycium barbarum polysaccharides on colon cancer cells involves G0/G1 phase arrest[J].Med Oncol,2011,28(1):121-126.
[7]吴灿军.天然色素及枸杞色素的提取和抗氧化作用的研究进展[J].陕西农业科学,2010,56(1):103-104.
[8]李维波,王玲,邓学端,等.2型糖尿病患者红细胞脆性与异形率的观察及枸杞多糖对二者的影响[J].河北中医,2000,22(8):585-586.
[9]Seca A M L,Silva A M S,Silvestre A J D.Lignanamides and other phenolic constituents from the bark of kenaf(Hibiscus cannabinus)[J].Phytochemistry,2001,58(8):1219-1223.
[10]Lajidel L,Escoubas P,Mizutani J.Termite antifeedant activity in Xylopia aethiopica[J].Phytochemistry,1995,40(4):1103-1112.
[11]Yoshihara T,Yamaguchi K,Takamatsu S,et al..A new lignanamide,grossamide,from bell pepper(Capsicumannuum var.grossurri)[J].Agric Biol Chem,1981,45(11):2593-2598.
[12]Chaves M H,Roque N F.Amides and lignanamides from Porcelia macrocarpa[J].Phytochemistry,1997,46(5):879-881.
[13]Sakakibara I,Ikeya Y,Hayashi K,Mrrsuhashi H.Three phenyldihydronaphthalene lignanamides from fruits of Cannabis sativa[J].Phytochemistry,1992,31(9):3219-3223.
[14]Jing X Z,Shu H G,Rui H F,et al.Neolignanamides,lignanamides,and other phenolic compounds from the root bark of Lycium chinense[J].Nat Prod,2013,76(1):51-58.
[15]Sakakibara I,Ikeya Y,Hayashi K,et al.Three acyclic bis-phenylpropane lignanamides from fruits of Cannabissativa[J].Phytochemistry,1995,38(4):1003-1007.
[16]袁惠,付辉政,钟瑞建,等.枫香树叶的化学成分[J].中国实验方剂学杂志,2014,20(13):102-105.
[17]刘锐,庾石山,裴月湖,等.楹树叶的化学成分[J].中国中药杂志,2009,34(16):2063-2065.