[关键词]
[摘要]
目的 研究兰科石斛属植物霍山石斛Dendrobium huoshanense的化学成分及其酪氨酸酶抑制活性。方法 采用硅胶柱色谱、Sephadex LH-20凝胶柱色谱及半制备高效液相色谱等色谱分离方法分离纯化得到单体化合物,利用MS、1D, 2D NMR等波谱学方法鉴定单体化合物的结构。同时以酪氨酸酶为筛选模型对分离得到的单体化合物进行酪氨酸酶抑制活性测试。结果 从霍山石斛的茎中分离得到了11个化合物,分别鉴定为反式阿魏酸十九烷酯(1)、反式对羟基桂皮酸十九烷酯(2)、2,4,7-三羟基-9,10-二氢菲(3)、柚皮素(4)、5-羟基-3,4'-二甲氧基联苄(5)、5-羟基-3-甲氧基联苄(6)、杯鞘石斛酚A(7)、4-羟基-3,5,4'-三甲氧基联苄(8)、阿魏酸甲酯(9)、原儿茶酸(10)、对羟基苯甲醛(11)。化合物4、7在100μmol/L浓度下对酪氨酸酶的抑制率为39.0%、38.3%。结论 化合物1、2为新化合物,命名为霍山石斛脂素A、霍山石斛脂素B;化合物3、5、7~9为首次从该植物中分离得到。化合物1、2、9为简单苯丙素类成分,3为二氢菲类成分,4为二氢黄酮类成分,5~8为联苄类成分。化合物4、7显示出潜在美白功效。
[Key word]
[Abstract]
Objective To study on the chemical constituents from Dendrobium huoshanense. Methods The chemical constituents were separated and purified by silica gel, Sephadex LH-20, semi-prepared HPLC and other chromatography techniques. Their structures were elucidated by MS, 1D and 2D NMR spectroscopic data. Results Eleven compounds (1—11) were isolated, and were identified as trans-ferulic acid nonadecyl ester (1), trans-p-hydroxycinnamic acid nonadecyl ester (2), 2,4,7-trihydroxy-9,10-dihydrophenanthrene (3), naringenin (4), 5-hydroxy-3,4′-dimethoxybibenzyl (5), 5-hydroxy-3-methoxybibenzyl (6), dendrogratiol A (7), amoenylin (8), methyl ferulate (9), protocatechuic acid (10), p-hydroxybenzaldehyde (11). At a concentration of 100 μmol/L, compounds 4 and 7 exhibited inhibitory rates of 39.0% and 38.3% against tyrosinase, respectively. Conclusion Compounds 1 and 2 are new compounds, named dendrohuoshanin A and dendrohuoshanin B. Compounds 3, 5, 7—9 were isolated for the first time from this plant. Compound 3 was the first to be separated and purified through phytochemical methods from this plant. Compounds 1, 2, and 9 belong to simple phenylpropanoids, compound 3 is a dihydrophenanthrene, compound 4 is a dihydroflavone, and compounds 5—8 are bibenzyls. Compounds 4 and 7 show potential skin-whitening effects.
[中图分类号]
R284.1
[基金项目]
安徽省自然科学基金面上项目(2308085MH301);安徽省中药资源保护与持续利用工程实验室开放课题(TCMRPSU-2022-01);皖西学院高层次人才基金项目(WGKQ2022074)