糙叶五加茎化学成分研究
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摘要
目的基于脂多糖(LPS)诱导的巨噬细胞RAW264.7和小胶质细胞BV2为生物活性导向模型研究糙叶五加Acanthopanax henryi茎的化学成分。方法采用硅胶柱色谱、凝胶柱色谱、制备薄层及重结晶等方法进行分离纯化,利用波谱分析结合理化性质鉴定化合物的结构。结果从糙叶五加茎甲醇提取物的醋酸乙酯萃取部位中分离得到18个化合物,分别鉴定为对羟基苯甲酸(1)、反式对羟基肉桂酸(2)、反式咖啡酸甲酯(3)、咖啡酸(4)、反式松柏醛(5)、丁香醛(6)、香草醛(7)、6-甲氧基-7-羟基香豆素(8)、反式芥子醛(9)、十一烷二酸单甲酯(10)、(-)-芝麻素(11)、3-O-咖啡酰奎宁酸(12)、5-O-咖啡酰奎宁酸(13)、1,3-双咖啡酰奎宁酸(14)、1,4-双咖啡酰奎宁酸(15)、1,5-双咖啡酰奎宁酸(16)、豆甾醇(17)、β-谷甾醇(18)。结论化合物10为首次从五加科植物中分离得到;除化合物12、14、17、18外,其他化合物均为首次从该植物中分离得到。
Objective To study the chemical constituents from stems of Acanthopanax henryi based on LPS-induced macrophages RAW264.7 and microglia BV2 as the bioactivity guided model. Methods The compounds were isolated and purified by silica gel and Sephadex LH-20 column chromatography, as well as Prep-TLC and recrystallization methods. Their structures were identified on the basis of their physicochemical properties and spectroscopic data. Results Eighteen compounds were obtained from A. henryi and their chemical structures were identified as p-hydroxybenzoic acid(1), trans-p-hydroxycinnamic acid(2),(E)-caffeic acid methyl ester(3),caffeic acid(4), trans-coniferyl aldehyde(5), syringaldehyde(6), vanillin(7), 6-methoxy-7-hydroxycoumarin(8), trans-sinapaldehyde(9), undecane-1,11-dioic acid monomethyl ester(10),(-)-sesamin(11), 3-O-caffeoyl-quinic acid(12), 5-O-caffeoyl-quinic acid(13),1,3-di-O-caffeoyl-quinic acid(14), 1,4-di-O-caffeoyl-quinic acid(15), 1,5-di-O-caffeoyl-quinic acid(16), stigmasterol(17), andβ-sitosterol(18), respectively. Conclusion To the best of our knowledge, compound 10 was isolated from Araliaceae for the first time.Except compounds 12, 14, 17, and 18, all of other compounds were obtained from this species for the first time.
Objective To study the chemical constituents from stems of Acanthopanax henryi based on LPS-induced macrophages RAW264.7 and microglia BV2 as the bioactivity guided model. Methods The compounds were isolated and purified by silica gel and Sephadex LH-20 column chromatography, as well as Prep-TLC and recrystallization methods. Their structures were identified on the basis of their physicochemical properties and spectroscopic data. Results Eighteen compounds were obtained from A. henryi and their chemical structures were identified as p-hydroxybenzoic acid(1), trans-p-hydroxycinnamic acid(2),(E)-caffeic acid methyl ester(3),caffeic acid(4), trans-coniferyl aldehyde(5), syringaldehyde(6), vanillin(7), 6-methoxy-7-hydroxycoumarin(8), trans-sinapaldehyde(9), undecane-1,11-dioic acid monomethyl ester(10),(-)-sesamin(11), 3-O-caffeoyl-quinic acid(12), 5-O-caffeoyl-quinic acid(13),1,3-di-O-caffeoyl-quinic acid(14), 1,4-di-O-caffeoyl-quinic acid(15), 1,5-di-O-caffeoyl-quinic acid(16), stigmasterol(17), andβ-sitosterol(18), respectively. Conclusion To the best of our knowledge, compound 10 was isolated from Araliaceae for the first time.Except compounds 12, 14, 17, and 18, all of other compounds were obtained from this species for the first time.
引文
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[2]Zhang X D,Liu X Q,Kim Y H,et al.Chemical constituents and their acetyl cholinesterase inhibitory and antioxidant activities from leaves of Acanthopanax henryi:Potential complementary source against Alzheimer’s disease[J].Arch Pharm Res,2014,37(5):606-616.
[3]Li Z,Li X J,Kwon O K,et al.Chemical constituents from leaves of Acanthopanax henryi(II)[J].Nat Prod Sci,2015,21(3):196-204.
[4]Han Y H,Li Z,Um J Y,et al.Anti-adipogenic effect of glycoside St-E2 and glycoside St-C1 isolated from the leaves of Acanthopanax henryi(Oliv.)Harms in 3T3-L1cells[J].Biosc Biotechnol Biochem,2016,80(12):2391-2400.
[5]Kang D H,Kang O H,Li Z,et al.Anti-inflammatory effects of Ciwujianoside C3,extracted from the leaves of Acanthopanax henryi(Oliv.)Harms,on LPS-stimulated RAW 264.7 cells[J].Mol Med Rep,2016,14(4):3749-3758.
[6]张艳军,聂辉,周德雄,等.桂野桐化学成分的研究[J].中草药,2017,48(11):2172-2176.
[7]李汝鑫,程锦堂,焦梦娇,等.钩藤叶化学成分研究[J].中草药,2017,48(8):1499-1505.
[8]霍立娜,王威,刘洋,等.紫苏叶化学成分研究[J].中草药,2016,47(1):26-31.
[9]丁林芬,王海垠,王扣,等.福建柏化学成分研究[J].中草药,2017,48(4):639-643.
[10]余小红,李盼盼,耿圆圆,等.小远志化学成分研究[J].林产化学与工业,2017,37(1):149-154.
[11]李干鹏,罗阳,李尚秀,等.小叶杜鹃花的化学成分研究[J].中草药,2014,45(12):1668-1672.
[12]袁谱龙,王雪萍,陈凯先,等.水茄茎化学成分的研究[J].中成药,2016,38(1):104-107.
[13]Ravi S,Padmanabhan D,Mamdapur V R.Macrocyclic musk compounds:Synthetic approaches to key intermediates for exaltolide,exaltone and dilactones[J].JIndian Institute Sci,2013,81(3):299-312.
[14]于凯,宋洋,路阳,等.无梗五加根中苯丙素类化合物的研究[J].天然产物研究与开发,2012,24(4):469-472.
[15]Ma Y C,Wang X Q,Hou F F,et al.Rapid resolution liquid chromatography(RRLC)analysis and studies on the stability of Shuang-Huang-Lian preparations[J].JPharm Biomed Anal,2011,54(2):265-272.
[16]李菁,于德泉.灯盏花化学成分研究[J].中国中药杂志,2011,36(11):1458-1462.
[17]Kwon H C,Jung C M,Shin C G,et al.A new caffeoyl quinic acid from Aster scaber and its inhibitory activity against human immunodeficiency virus-1(HIV-1)integrase[J].Chem Pharm Bull,2000,48(11):1796-1798.
[18]Lin L C,Yang L L,Chou C J.Constituents from the stems of Ecdysanthera rosea[J].J Chin Med,2002,13(4):191-195.
[19]Kim W K,Bach D H,Ryu H W,et al.Cytotoxic activities of Telectadium dongnaiense and its constituents by inhibition of the Wnt/β-catenin signaling pathway[J].Phytomedicine,2017,34:136-142.
[20]刘恒言,金钟焕,刘向前,等.糙叶五加根皮化学成分研究[J].湖南中医药大学学报,2012,32(11):34-37.