蒺藜果实的化学成分研究
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摘要
目的研究蒺藜科植物蒺藜Tribulus terrester的干燥成熟果实的化学成分。方法利用硅胶柱色谱、Sephadex LH-20凝胶柱色谱、制备HPLC和薄层色谱等方法进行分离、纯化,并结合HR-ESI-MS与现代波谱学技术鉴定化合物结构。结果从蒺藜果实中分离得到14个化合物,分别鉴定为N-p-阿魏酰酪胺(1)、N-trans-p-coumaroyl-3-O-methyldopamine(2)、甲基阿魏酸(3)、咖啡酸甲酯(4)、原儿茶酸甲酯(5)、trifilines A(6)、5β-spirost-25(27)-en-3β-ol-12-one 3-O-{β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranoside}(7)、tribulosaponin B(8)、isoterrestrosin B(9)、25(R)-螺甾烷-3,5-二烯-12-酮(10)、25(R)-螺甾烷-24β-羟基-4-烯-3,12-酮(11)、26-O-β-D-glucopyranosyl-(25S)-5α-furostane-20(22)-en-12-one-3β,26-diol-3-O-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside(12)、terrestrinone A1(13)和terrestrinone A2(14)。结论化合物1～7为首次从蒺藜科植物中分离得到。
Objective To study the chemical constituents from the fruits of Tribulus terrester. Methods The constituents were isolated and purified by silica gel column chromatography, Sephadex LH-20 column chromatography, preparative HPLC and TLC methods. The structures were identified by HR-ESI-MS and spectral analysis methods. Results Fourteen compounds were isolated from the fruits of Tribulus terrester and the structures were identified as N-p-feruloyltyramine(1), N-trans-p-coumaroyl-3-Omethyldopamine(2), methyl ferulic acid(3), caffeic acid methyl ester(4), protocatechuic acid methyl ester(5), trifilines A(6),5β-spirost-25(27)-en-3β-ol-12-one 3-O-{β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranoside}(7),tribulosaponin B(8), isoterrestrosin B(9), 25(R)-spirostane-3,5-diene-12-one(10), 25(R)-spirostane-24β-ol-4-ene-3,12-dione(11),26-O-β-D-glucopyranosyl-(25 S)-5α-furostane-20(22)-en-12-one-3β,26-diol-3-O-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside(12), terrestrinone A1(13), and terrestrinone A2(14). Conclusion Compounds 1—7 are obtained from the Zygophllyaceae for the first time.
Objective To study the chemical constituents from the fruits of Tribulus terrester. Methods The constituents were isolated and purified by silica gel column chromatography, Sephadex LH-20 column chromatography, preparative HPLC and TLC methods. The structures were identified by HR-ESI-MS and spectral analysis methods. Results Fourteen compounds were isolated from the fruits of Tribulus terrester and the structures were identified as N-p-feruloyltyramine(1), N-trans-p-coumaroyl-3-Omethyldopamine(2), methyl ferulic acid(3), caffeic acid methyl ester(4), protocatechuic acid methyl ester(5), trifilines A(6),5β-spirost-25(27)-en-3β-ol-12-one 3-O-{β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranoside}(7),tribulosaponin B(8), isoterrestrosin B(9), 25(R)-spirostane-3,5-diene-12-one(10), 25(R)-spirostane-24β-ol-4-ene-3,12-dione(11),26-O-β-D-glucopyranosyl-(25 S)-5α-furostane-20(22)-en-12-one-3β,26-diol-3-O-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside(12), terrestrinone A1(13), and terrestrinone A2(14). Conclusion Compounds 1—7 are obtained from the Zygophllyaceae for the first time.
引文
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[2]戴莹.蒺藜愈伤组织培养体系的建立及其总黄酮醇苷含量的测定[D].长春:吉林农业大学,2016.
[3]黄艳,李齐修,刘元,等.簇花清风藤的化学成分研究[J].中草药,2014,45(6):765-769.
[4]Juliana C,Lucia M.Aristolactams and alkamides of Aristolochia gigantea[J].Molecules,2010,15(12):9462-9472.
[5]尹伟,宋祖荣,刘金旗,等.香橼化学成分研究[J].中药材,2015,38(10):2091-2094.
[6]朱仝飞,陈日荣,孙庆文,等.西藏胡黄连化学成分研究[J].中草药,2017,48(2):263-265.
[7]Li S F,Cheng Y Y,Zhang Y,et al.β-Carboline alkaloids from Trigonostemon filipes and Trigonostemon lii[J].Nat Prod Bioprospect,2012,2(3):126-129.
[8]Skhirtladze A,Perrone A,Montoro P,et al.Steroidal saponins from Yucca gloriosa L.rhizomes:LC-MSprofiling,isolation and quantitative determination[J].Phytochemistry,2011,72(1):126-135.
[9]Erdal B,Ikhlas A K.New steroidal glycosides from the fruits of Tribulus terrestris[J].J Nat Prod,2000,63(12):1699-1701.
[10]黄金文,蒋山好,谭昌恒,等.三个新甾体皂甙元的结构鉴定[J].有机化学,2002,22(11):917-921.
[11]Xu Y J,Liu Y H,Xu T H,et al.A new furostanol glycoside from Tribulus terrestris[J].Molecules,2010,15(2):613-618.
[12]Hong S S,Choi Y H,Jeong W,et al.Two new furostanol glycosides from the fruits of Tribulus terrestris[J].Tetrahedron Lett,2013,54(30):3967-3970.