剑叶耳草中的1个新咖啡酸苷化学成分及其抗肿瘤活性
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摘要
目的研究剑叶耳草Hedyotiscaudatifolia的化学成分。方法采用硅胶、聚酰胺、SephadexLH-20凝胶等柱色谱技术进行分离纯化,通过化合物的核磁共振、质谱等光谱数据和理化性质鉴定其结构。结果从剑叶耳草的甲醇提取物中分离得到10个化合物,其结构分别鉴定为剑叶耳草苷A(1)、β-谷甾醇(2)、5α-豆甾烷-3,6-二酮(3)、7-羟基-6-甲氧基香豆素(4)、齐墩果酸(5)、乌苏酸(6)、坡模酸(7)、3α,19α-二羟基-12-烯-24, 28-乌苏酸(8)、2α,3β,24-三羟基-12-烯-28-齐墩果酸(9)、2α,3α-二羟基-12-烯-28-齐墩果酸(10)。结论化合物1为新的咖啡酸葡萄糖苷,化合物7～10均为首次从该植物中分离得到。化合物1具有一定的抑制肿瘤细胞生长活性。
Objective To study the chemical constituents of Hedyotis caudatifolia. Methods These compounds were isolated from H. caudatifolia and purified by repeated silica gel, polyamine, Sephadex LH-20 column chromatography and other methods. Their structures were identified by NMR, MS, and physico-chemical properties. Results Ten compounds were isolated and elucidated as hedycaffeoylglucoside A(1), β-sitosterol(2), 5α-stigmastane-3,6-dione(3), 7-hydroxy-6-methoxycoumarin(4), oleanolic acid(5), ursolic acid(6), pomolic acid(7), 3α,19α-dihydroxyurs-12-en-24,28-dioic acid(8), 2α,3β,24-trihydroxyolean-12-en-28-oic acid(9), and 2α,3α-dihydroxyolean-12-en-28-oic acid(10), respectively. Conclusion Compound 1 is a new caffeoyl glucoside and compounds 7—10 are isolated from this plant for the first time. Compound 1 exhibits cytotoxicity against four tumor cells.
Objective To study the chemical constituents of Hedyotis caudatifolia. Methods These compounds were isolated from H. caudatifolia and purified by repeated silica gel, polyamine, Sephadex LH-20 column chromatography and other methods. Their structures were identified by NMR, MS, and physico-chemical properties. Results Ten compounds were isolated and elucidated as hedycaffeoylglucoside A(1), β-sitosterol(2), 5α-stigmastane-3,6-dione(3), 7-hydroxy-6-methoxycoumarin(4), oleanolic acid(5), ursolic acid(6), pomolic acid(7), 3α,19α-dihydroxyurs-12-en-24,28-dioic acid(8), 2α,3β,24-trihydroxyolean-12-en-28-oic acid(9), and 2α,3α-dihydroxyolean-12-en-28-oic acid(10), respectively. Conclusion Compound 1 is a new caffeoyl glucoside and compounds 7—10 are isolated from this plant for the first time. Compound 1 exhibits cytotoxicity against four tumor cells.
引文
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[2]江苏省植物研究所.新华本草纲要(第1册)[M].上海:上海科学技术出版社,1988.
[3]Permana D,Lajis N H,Othman,A G,et al.Anthraquinones from Hedyotis herbacea[J].J Nat Prods,1999,62(10):1430-1431.
[4]Le H D,Phung N K P.Anthraquinones from Hedyotis pinifolia[J].J Chem,2009,47(5):581-585.
[5]Ahmad R,Shaari K,Lajis N H,et al.Anthraquinones from Hedyotis capitellata[J].Phytochemistry,2005,66(10):1141-1147.
[6]Phuong N M,Van Sung T,Schmidt J,et al.Capitelline-Anew indole alkaloid from Hedyotis capitellata[J].Nat Prod Lett,1998,11(2):93-100.
[7]Phuong N M,Van Sung T,Porzel A,et al.Two newβ-carboline alkaloids from Hedyotis capitellata var.mollis[J].Planta Med,1999,65(8):761-762.
[8]Peng J N,Feng X Z,Liang X T.Two new iridoids from Hedyotis chrysotricha[J].J Nat Prods,1999,62(4):611-612.
[9]Ye M,Su J J,Liu S T,et al.(24S)-Ergostane-3β,5α,6β-triol from Hedyotis chrysotricha with inhibitory activity on migration of SK-HEP-1 human hepatocarcinoma cells[J].Nat Prod Res,2013,27(12):1136-1140.
[10]袁青梅,杨红卫,赵静峰,等.纤花耳草化学成分的分离与鉴定[J].中草药,2004,35(9):981-982.
[11]Luo P,Su J,Zhu Y,et al.A new anthraquinone and eight constituents from Hedyotis caudatifolia Merr.et Metcalf:Isolation,purification and structural identification[J].Nat Prod Res,2016,30(19):2190-2196.
[12]Ge Y C,Zhang H J,Wang K W,et al.Aporphine alkaloids from Illigera aromatica from Guangxi province,China[J].Phytochemistry,2018,154:73-76.
[13]Wang K W,Li D,Wu B,et al.New cytotoxic dimeric and trimeric coumarins from Chimonanthus salicifolius[J].Phytochem Lett,2016,16:115-120.
[14]李曼娜.紫苏粕中咖啡酸-3-O-葡萄糖苷的提取与富集工艺优化[D].北京:北京林业大学,2016.
[15]韵小娟,舒火明,纪明慧,等.厚皮树树皮的化学成分研究[J].化学研究与应用,2012,24(4):610-613.
[16]沈玉萍,钟雄雄,余筱洁,等.中药香椿叶的化学成分研究[J].中国药学杂志,2013,48(1):22-24.
[17]林朝展,祝晨蔯,邓贵华,等.枇杷叶紫珠化学成分研究[J].中药材,2010,33(6):897-900.
[18]潘萍,孙启时.大叶紫珠的化学成分[J].沈阳药科大学学报,2006,23(9):565-567.
[19]代华年,马国需,邹节明,等.金樱子根三萜类的化学成分研究[J].中草药,2016,47(3):374-378.
[20]Thuong P T,Lee C H,Dao T T,et al.Triterpenoids from the leaves of Diospyros kaki(Persimmon)and their inhibitory effects on protein tyrosine phosphatase 1B[J].J Nat Prods,2008,71(10):1775-1778.
[21]卢汝梅,杨长水,韦建华.荔枝草化学成分的研究[J].中草药,2011,42(5):859-862.
[22]刘普,段宏泉,潘勤,等.委陵菜三萜成分研究[J].中国中药杂志,2006,31(22):1875-1879.