“太白七药”竹根七的化学成分研究
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摘要
目的研究竹根七的化学成分。方法经70%乙醇提取,利用正相硅胶柱色谱、反相硅胶柱色谱、Sephadex LH-20凝胶柱色谱、制备高效液相色谱等分离方法,从竹根七70%乙醇提取液的正丁醇萃取物中分离得到6个化合物,根据其理化性质及现代波谱技术鉴定其结构。结果从竹根七中分离得到2个多羟基呋甾皂苷、2个多羟基螺甾烷类化合物和2个烯丙基苯糖苷,分别鉴定为1β,2β,3β,4β,5β,26-hexahydroxyfurost-20(22),25(27)-dien-5,26-O-β-D-glucopyranoside(1)、tupisteroide B(2)、(25S)-5β-spirostan-1β,2β,3β,4β,5,6β-hexol(3)、(25R)-5β-spirostan-1β,2β,3β,4β,5,6β-hexol(4)、chavicolβ-D-glucopyranoside(5)和demethyleugenolβ-D-glucopyranoside(6)。结论化合物3和4为首次从开口箭属植物中分离得到,化合物5和6则是首次在百合科植物中分离得到。
Objective To determine the chemical constituents from the rhizomes of Tupistra chinensis Baker..Methods The rhizomes of Tupistra chinensis Baker. were extracted with 70% ethanol. The crude extraction was suspended in water, and extracted with petroleum ether and n-butanol. The samples were purified by silica gel column chromatography, Sephadex LH-20 gel chromatography, ODS column chromatography and semi preparative HPLC. The structures of the isolated compounds were determined on the basis of chemical quality and spectroscopic methods. Results Six compounds were isolated and identified as 1β, 2β, 3β, 4β, 5β, 26-hexahydroxy furost-20(22), 25(27)-dien-5, 26-O-β-D-glucopyranoside(1), tupisteroide B(2),(25 S)-5β-spirostan-1β, 2β, 3β, 4β,5, 6β-hexol(3),(25 R)-5β-spirostan-1β, 2β, 3β, 4β, 5, 6β-hexol(4), chavicol β-D-glucopyranoside(5), demethyleugenol β-D-glucopyranoside(6). Conclusion Compounds 3 and 4 have been obtained from Tupistra chinensis Baker.Baker. for the first time, and compound 5 and 6 from Liliaceae for the first time.
Objective To determine the chemical constituents from the rhizomes of Tupistra chinensis Baker..Methods The rhizomes of Tupistra chinensis Baker. were extracted with 70% ethanol. The crude extraction was suspended in water, and extracted with petroleum ether and n-butanol. The samples were purified by silica gel column chromatography, Sephadex LH-20 gel chromatography, ODS column chromatography and semi preparative HPLC. The structures of the isolated compounds were determined on the basis of chemical quality and spectroscopic methods. Results Six compounds were isolated and identified as 1β, 2β, 3β, 4β, 5β, 26-hexahydroxy furost-20(22), 25(27)-dien-5, 26-O-β-D-glucopyranoside(1), tupisteroide B(2),(25 S)-5β-spirostan-1β, 2β, 3β, 4β,5, 6β-hexol(3),(25 R)-5β-spirostan-1β, 2β, 3β, 4β, 5, 6β-hexol(4), chavicol β-D-glucopyranoside(5), demethyleugenol β-D-glucopyranoside(6). Conclusion Compounds 3 and 4 have been obtained from Tupistra chinensis Baker.Baker. for the first time, and compound 5 and 6 from Liliaceae for the first time.
引文
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[14]张东东.小竹根七化学成分研究[D].西安:陕西中医药大学,2016.
[15]Kznmoto T,Mimaki Y,Sashida Y,et al. Steroidal constituents from the under-ground parts of Reineckea carnea and their inhibitory activity on cAMP phosphodiesterase[J].Chem Pharm Bull(Tokyo),1994,42(4):926-931.
[16]Coen M,Engel R,Nahrstedt A. Chavicolβ-D-glucoside,a phenylpropanoid heteroside,benzyl-β-D-gluco-side and glycosidically bound volatiles from subspecies of Cedronella canariensis[J]. Phytochemistry,1995,40(1):149-155.
[17]Yoshizawa Y,Kawaii S,Kanauchi M,et al. Chavicol and related compounds as nematocides[J]. Biosci Biotechnol Biochem,2008,57(9):1572-1574.
[18]Ly TN,Yamauchi R,Shimoyamada M,et al. Isolation and structural elucidation of some glycosides from the rhizomes of smaller galanga(Alpinia officinarum Hance)[J].J Agr Food Chem,2002,50(17):4919-4924.
[2]中国科学院《中国植物志》编委会.中国植物志[M].北京:科学出版社,1994:6-7.
[3]朱光正,于传林,蔡晶,等.开口箭提取物抗肿瘤作用研究[J].中药材,2006,29(3):277-279.
[4]晏传奇,黄文峰,邹坤,等.开口箭提取物对小鼠移植性实体瘤H22的抑制作用[J].江苏中医药,2009,41(9):77-78.
[5]邬昊洋,周园,李诺飞,等.开口箭醇提取物抗慢性咽炎活性研究[J].三峡大学学报(自然科学版),2012,34(2):83-85.
[6]徐兰兰,邹坤,汪鋆植,等.开口箭提取物治疗急性咽炎活性研究[J].江苏中医药,2008,40(8):78-79.
[7]杨春燕,杨兴海,刘英,等.开口箭祛痰抗炎及抑菌试验研究[J].中国民族民间医药杂志,2005,(2):103-106,123.
[8]汤子春,邹坤.开口箭与鞘蛇菰提取物醒酒作用的实验研究[J].时珍国医国药,2006,17(1):2163-2165.
[9]解燕,朱光正,于传林,等.开口箭酸性多糖对小鼠免疫功能的调节作用及抗肿瘤作用的初步研究[J].中药材,2010,4(33):596-599.
[10]汤海峰,易杨华,王忠壮,等.太白楤木根皮化学成分的研究[J].中国药学杂志,1996,31(4):204-206.
[11]Li Y,Wang X,He H,et al. Steroidal saponins from the roots and rhizomes of Tupistra chinensis[J]. Molecules,2015,20(8):13659-13669.
[12]Liu CX,Guo ZY,Xue YH,et al. Tupisteroide A–C,three new polyhydroxylated steroidal constituents from the roots of Tupistra chinensis[J]. Magn Reson Chem,2012,50(4):320-324.
[13]Pawan KA. 25R/25S stereochemistry of spirostane-type steroidal sapogenins and steroidal saponins via chemical shift of geminal protons of ring-F[J]. Magn Reson Chem,2003,41(11):965-968.
[14]张东东.小竹根七化学成分研究[D].西安:陕西中医药大学,2016.
[15]Kznmoto T,Mimaki Y,Sashida Y,et al. Steroidal constituents from the under-ground parts of Reineckea carnea and their inhibitory activity on cAMP phosphodiesterase[J].Chem Pharm Bull(Tokyo),1994,42(4):926-931.
[16]Coen M,Engel R,Nahrstedt A. Chavicolβ-D-glucoside,a phenylpropanoid heteroside,benzyl-β-D-gluco-side and glycosidically bound volatiles from subspecies of Cedronella canariensis[J]. Phytochemistry,1995,40(1):149-155.
[17]Yoshizawa Y,Kawaii S,Kanauchi M,et al. Chavicol and related compounds as nematocides[J]. Biosci Biotechnol Biochem,2008,57(9):1572-1574.
[18]Ly TN,Yamauchi R,Shimoyamada M,et al. Isolation and structural elucidation of some glycosides from the rhizomes of smaller galanga(Alpinia officinarum Hance)[J].J Agr Food Chem,2002,50(17):4919-4924.