岗梅茎的化学成分研究
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摘要
综合运用多种色谱技术从我国岭南特色药材岗梅茎的水提物中分离得到了13个化学成分,通过波谱技术将它们分别鉴定为柳叶绣线菊新木脂醇(1),rel-(7R,8S)-3,3',5-trimethoxy-4',7-epoxy-8,5'-neolignan-4,9,9'-triol 9-β-D-glucopyranoside(2),(+)-cycloolivil(3),(+)-syringaresinol-4'-O-β-D-monoglucoside(4),鹅掌楸苦素(5),咖啡酸(6),3,4-二羟基-5-甲氧基苯甲醛(7),1,2,4-苯三酚(8),3,4,5-trimethoxyphenyl-1-O-β-D-apiofuranosyl-(1″→6')-glucopyranoside(9),秦皮乙素(10),隐绿原酸乙酯(11),绿原酸乙酯(12),和rel-5-(3S,8S-dihydroxy-1R,5S-dimethyl-7-oxa-6-oxobicyclo[3,2,1]oct-8-yl)-3-methyl-2Z,4Epentadienoic acid(13)。化合物1~5为木脂素类化合物、6~12为其他酚酸类化合物、13为倍半萜内酯类化合物,其中7,8,11,13为首次从冬青属植物中分离得到,1~3,9,10,12为首次从岗梅中分离得到。抗炎活性筛选结果显示,化合物1和9对RAW264.7细胞中NO的生成显示中等抑制作用,化合物10具有微弱的抑制效果,其IC50分别为35.7,50.6,98.7μmol·L-1。
Phytochemical investigation on the stems of Ilex asprella by using various chromatographic techniques led to the isolation of 13 compounds. By spectroscopic analyses and comparisons the spectral data with those in literatures,these compounds were identified as salicifoneoliganol( 1),rel-( 7 R,8 S)-3,3',5-trimethoxy-4',7-epoxy-8,5'-neolignan-4,9,9'-triol 9-β-D-glucopyranoside( 2),( +)-cycloolivil(3),( +)-syringaresinol-4'-O-β-D-monoglucoside(4),liriodendrin(5),caffeic acid(6),3,4-dihydroxy-5-methoxybenzaldehyde(7),benzene-1,2,4-triol(8),3,4,5-trimethoxyphenyl-1-O-β-D-apiofuranosyl(1″→6')-glucopyranoside( 9),aeculetin(10),cryptochlorogenic acid ethyl ester(11),chlorogenic acid ethyl ester(12),and rel-5-(3 S,8 S-dihydroxy-1 R,5 S-dimethyl-7-oxa-6-oxobicyclo [3,2,1]oct-8-yl)-3-methyl-2 Z,4 E-pentadienoic acid( 13). Among them,compounds 7,8,11,and 13 were isolated from genus Ilex for the first time,and 1-3,9,10,and 12 were isolated from this speciesfor the first time. The anti-inflammatory assay results of these compounds showed that compounds 1 and 9 showed moderate inhibitory effect against NO production in RAW 267. 4 cells with IC50 values of 35. 7 and 50. 6 μmol·L-1,in vitro respectively,whereas compound 10 showed weak inhibition(IC50 value98. 7 μmol·L-1).
Phytochemical investigation on the stems of Ilex asprella by using various chromatographic techniques led to the isolation of 13 compounds. By spectroscopic analyses and comparisons the spectral data with those in literatures,these compounds were identified as salicifoneoliganol( 1),rel-( 7 R,8 S)-3,3',5-trimethoxy-4',7-epoxy-8,5'-neolignan-4,9,9'-triol 9-β-D-glucopyranoside( 2),( +)-cycloolivil(3),( +)-syringaresinol-4'-O-β-D-monoglucoside(4),liriodendrin(5),caffeic acid(6),3,4-dihydroxy-5-methoxybenzaldehyde(7),benzene-1,2,4-triol(8),3,4,5-trimethoxyphenyl-1-O-β-D-apiofuranosyl(1″→6')-glucopyranoside( 9),aeculetin(10),cryptochlorogenic acid ethyl ester(11),chlorogenic acid ethyl ester(12),and rel-5-(3 S,8 S-dihydroxy-1 R,5 S-dimethyl-7-oxa-6-oxobicyclo [3,2,1]oct-8-yl)-3-methyl-2 Z,4 E-pentadienoic acid( 13). Among them,compounds 7,8,11,and 13 were isolated from genus Ilex for the first time,and 1-3,9,10,and 12 were isolated from this speciesfor the first time. The anti-inflammatory assay results of these compounds showed that compounds 1 and 9 showed moderate inhibitory effect against NO production in RAW 267. 4 cells with IC50 values of 35. 7 and 50. 6 μmol·L-1,in vitro respectively,whereas compound 10 showed weak inhibition(IC50 value98. 7 μmol·L-1).
引文
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[2]杜冰曌,杨鑫瑶,冯晓,等.岗梅的化学成分和药理作用研究进展[J].中国中药杂志,2017,42(1):20.
[3]颜世达,姚慧丽,张英华,等.柳叶绣线菊化学成分研究[J].中草药,2016,47(16):2806.
[4]Wang Y H,Sun Q Y,Yang F M,et al.Neolignans and caffeoyl derivatives from Selaginella moellendorffii[J].Helv Chim Acta,2010,93(12):2467.
[5]Ghogomu-Tih R,Bodo B,Nyasse B,et al.Isolation and identification of(-)-olivil and(+)-cycloolivil from Stereospermum kunthianum[J].Planta Med,1985,51(5):464.
[6]郭红丽,周金云.青蛇藤正丁醇部分苷类成分的分离与鉴定[J].中国中药杂志,2005,30(1):44.
[7]宁颖,孙建,吕海宁,等.赤小豆的化学成分研究[J].中国中药杂志,2013,38(12):1938.
[8]Cui C B,Tezuka Y,Kikuchi T,et al.Constituents of a fern,davallia mariesii Moore.Ⅰ.isolation and structures of davallialactone and a new flavanone glucuronide[J].Chem Pharm Bull,1990,38(12):3218.
[9]邱蕴绮,漆淑华,张偲,等.阔苞菊的化学成分研究[J].中草药,2009,40(5):701.
[10]冯卫生,张艳丽,郑晓珂,等.绣球花的化学成分研究[J].中国药学杂志,2011,46(8):576.
[11]聂春晓,宋月林,陈东,等.白木香叶化学成分的研究[J].中国中药杂志,2009,34(7):858.
[12]钱正明,李会军,齐芳芳,等.红花忍冬的化学成分研究[J].中国药学杂志,2007,42(15):1132.
[13]Zhu X,Dong X,Wang Y,et al.Phenolic compounds from viburnum cylindricum[J].Helv Chim Acta,2010,88(2):339.
[14]Kikuzaki H,Kayano S,Fukutsuka N,et al.Abscisic acid related compounds and lignans in prunes(Prunus domestica L.)and their oxygen radical absorbance capacity(ORAC)[J].J Agric Food Chem,2004,52(2):344.
[15]Guo Q,Zeng K,Gao X,et al.Chemical constituents with NO production inhibitory and cytotoxic activities from Litsea cubeba[J].J Nat Med,2015,69(1):94.
[16]Peng W,Hui G,Liu J X,et al.Triterpenoid saponins with antiinflammatory activities from Ilex pubescens,roots[J].Phytochemistry,2017,134:122.
[17]Tan Q,Qiu M,Cao D,et al.Triterpenoids with antiplatelet aggregation activity from the roots of Ilex pubescens[J].Planta Med,2016,83(9):797.