论文部分内容阅读
目的:研究茜草科水团花属植物大叶水团花茎枝的化学成分并对其在多种体外药理模型上进行随机活性筛选。方法:运用硅胶、Sephadex LH-20柱色谱和制备型高效液相色谱等技术进行成分分离,通过NMR,MS等波谱数据和理化性质分析鉴定化合物的结构;在细胞水平的多种药理模型上,筛选化合物的体外肿瘤细胞毒、抗炎、抗氧化、抗HIV和神经细胞保护等活性。结果:从95%乙醇提取物中,分离并鉴定28个化合物,分别为5个芳香苷类化合物,clemochinenoside B(1),3,4,5-三甲氧基苯酚-β-D-呋喃芹糖氧基-(1→6)-β-D-吡喃葡萄糖苷(2),2-(4-羟基苯)乙基-β-D-呋喃芹糖氧基-(1→6)-β-D-葡萄糖苷(3),4-羟基-3-甲氧基苯酚1-O-β-D-[6-O-(4-羟基-3,5-二甲氧基苯甲酰基)]-吡喃葡萄糖苷(4)和β-D-吡喃葡萄糖氧基丁香酸酯(5);10个环烯醚萜苷,京尼平苷酸(6),京尼平苷(7),6β-羟基京尼平苷(8),6α-羟基京尼平苷(9),ixoside(10),ixoside 11-methyl ester(11),11-methyl forsythide(12),7β-hydroxysplendoside(13),栀子苷(14)和玉叶金花苷酸(15);5个木脂素,(+)-松脂醇(16),(+)-5′-甲氧基-松脂素(17),(+)-丁香树脂酚(18),(-)-落叶脂素(19)和evofolin-B(20);5个简单芳香类化合物,α-羟基乙酰香草酮(21),丁香酸(22),香草醛(23),3,4,5-三甲氧基苯酚(24)和2,6-二甲氧基对苯醌(25),以及3个常见的植物代谢产物β-谷甾醇(26)、甘露醇(27)和胡萝卜苷(28)。在1.0×10-5mol.L-1浓度下,它们在肿瘤细胞毒(MTT法,HCT-8,Bel-7402,BGC-823,A549和A2780细胞株)、抗炎(PAF,TNF-α和PGE2模型)、抗氧化(Fe2+-Cys诱导大鼠肝微粒体脂质过氧化模型)、抗HIV(VSVG/HIV模型)、神经保护(去血清和谷氨酸损伤模型)和抗糖尿病(PTPIB酶抑制模型)体外模型上均未显示出显著药理活性。结论:化合物1～20均为首次从水团花属植物中分得,它们的药理活性尚待在其他模型上进一步筛选评价。此外,通过2D NMR数据分析,对文献中报道的化合物10和11碳谱数据的错误归属进行了修正。
OBJECTIVE: To study the chemical constituents of stems and leaves of Phalaenopsis grandiflorum in Rubiaceae and to conduct random activity screening of the stems in a variety of in vitro pharmacological models. Methods: Silica gel, Sephadex LH-20 column and preparative HPLC were used to separate the constituents. The structures of the compounds were identified by NMR, MS and other physico-chemical properties. At various cell-level pharmacological models, The compounds were screened for in vitro cytotoxic, anti-inflammatory, anti-oxidant, anti-HIV and neuronal cell protection activities. Results: From the 95% ethanol extract, 28 compounds were isolated and identified, including 5 aromatosides, clemochinenoside B (1), 3,4,5-trimethoxyphenol-β-D- (1 → 6) -β-D-glucopyranoside (2), 2- (4-hydroxybenzene) ethyl- Glucopyranoside (3), 4-hydroxy-3-methoxyphenol 1-O- β -D- [6-0- (4-hydroxy-3,5-dimethoxybenzoyl)] - (4) and β-D-glucopyranosyloxy syringate (5); 10 iridoid glycosides, geniposidic acid (6), geniposide (7), 6β Hydroxy geniposide (8), 6α-hydroxy geniposide (9), ixoside (10), ixoside 11- methyl ester (11), 11- methyl forsythide (12), 7β-hydroxysplendoside (+) - pinoresinol (17), (+) - 5’-methoxy-psoralen (17) ) - clove phenolics (18), (-) - decalin (19) and evofolin-B (20); 5 simple aromatics, α-hydroxyacetyl vanillone (21) Vanillin (23), 3,4,5-trimethoxyphenol (24) and 2,6-dimethoxybenzoquinone (25) as well as 3 common plant metabolites, β-sitosterol ,honeydew Alcohol (27) and daucosterol (28). They showed significant inhibitory effects on tumor cytotoxicity (MTT assay, HCT-8, Bel 7402, BGC-823, A549 and A2780 cell lines), anti-inflammatory PGE2 model), anti-oxidant (Fe2 + -Cys induced rat liver microsomal lipid peroxidation model), anti-HIV (VSVG / HIV model), neuroprotection (demyelinating and glutamate damage model) and anti-diabetic Inhibition model) showed no significant pharmacological activity in vitro models. CONCLUSION: Compounds 1 ~ 20 were obtained for the first time from the genus Hydrangea, and their pharmacological activities have yet to be further screened and evaluated in other models. In addition, by the 2D NMR data analysis, the incorrect assignments of the 10 and 11 carbon spectral data reported in the literature were corrected.