[关键词]
[摘要]
目的 对扁刺峨眉蔷薇Rosa omeiensis f. pteracantha全株的化学成分和酪氨酸酶抑制活性进行研究。方法 将扁刺峨眉蔷薇样品进行干燥、粉碎,采用溶剂提取法、MCI HP20柱色谱、硅胶柱色谱、Sephadex LH-20凝胶柱色谱、半制备RP-HPLC等方法进行分离纯化,利用1D-NMR、MS等多种现代波谱技术对化合物进行结构鉴定。并采用B16F10细胞建立酪氨酸酶抑制活性评价模型,利用多巴氧化法评价化合物对B16F10细胞中的酪氨酸酶抑制活性。结果 从扁刺峨眉蔷薇75%甲醇提取物的醋酸乙酯萃取部位中共分离得到21个化合物,分别鉴定为野鸦椿酸(1)、negundonorin A(2)、覆盆子酸(3)、刺梨苷(4)、野蔷薇苷(5)、2α,3α-dihydroxy-19-oxo-18,19-seco-urs-11,13(18)-dien-28-oic acid(6)、胡萝卜苷(7)、小麦黄素(8)、8-甲氧羰基儿茶素(9)、柚皮素(10)、槲皮素(11)、3,3′-O-二甲基鞣花酸(12)、1-hydroxy-2,6-bis-epi-pinoresinol(13)、东莨菪素(14)、3-吲哚甲醛(15)、短叶苏木酚酸甲酯(16)、3,4,5-trimethoxyphenyl-(6′-O-galloyl)-O-β-D-glucopyranoside(17)、没食子酸甲酯(18)、原儿茶酸(19)、β-羟基-3-甲氧基-4-羟基苯乙酮(20)、异香草酸(21)。酪氨酸酶抑制活性筛选结果表明,在浓度40 μmol/L时,化合物1~3、5、13、14、16、21有显著酪氨酸酶抑制活性(P<0.05、0.01),且抑制作用高于阳性药曲酸。在浓度20 μmol/L时,化合物1、3、5、14、21具有显著的酪氨酸酶抑制活性(P<0.05、0.001)。结论 21个化合物均为首次从扁刺峨眉蔷薇中分离得到,其中化合物2、6、12、15、17、20为首次从蔷薇属中分离得到;多数化合物都具有显著的酪氨酸酶抑制活性,且活性高于阳性药曲酸。扁刺峨眉蔷薇资源在用于美白功效日用品的开发方面具有较高的潜力。
[Key word]
[Abstract]
Objective To study the chemical constituents and their inhibitory activities against tyrosinase from the whole plants of Rosa omeiensis f. pteracantha. Methods The samples from R. omeiensis f. pteracantha were dried and crushed, and were isolated and purified by solvent extraction, MCI HP20, silica gel, Sephadex LH-20 column chromatography, semi-preparative RP-HPLC and other methods. The structures of compounds were elucidated by 1D-NMR, MS and other modern spectral techniques. The tyrosinase inhibitory activity evaluation model was established in B16F10 cells, and the inhibitory activity of the compound was evaluated by dopa oxidation method. Results A total of 21 compounds were isolated from the ethyl acetate extract of 75% methanol extract of R. omeiensis f. pteracantha and identified as euscaphic (1), negundonorin A (2), raspberry acid (3), kajiichigoside F1(4), rosamultin (5), 2α,3α-dihydroxy-19-oxo-18,19-seco-urs-11,13(18)-dien-28-oic acid (6),β-sitosterol-β-D-glucopyranoside (7), tricin (8), 8-methoxycarbonylcatechin (9), naringenin (10), quercetin (11), 3,3′-di-O-methylellagic acid (12), 1-hydroxy-2,6-bis-epi-pinoresinol (13), scopoletin (14), indole-3-carboxaldehyde (15), methyl brevifolin-carboxylate (16), 3,4,5-trimethoxyphenyl-(6′-O-galloyl)-O-β-D-glucopyranoside (17), methyl gallate (18), protocatechuic acid (19), β-hydroxypropiovanillone (20), isovanillic acid (21). The results of tyrosinase inhibitory activities screening showed that compounds 1—3, 5, 13, 14, 16 and 21 exhibited significant tyrosinase inhibitory activities at 40 μmol/L (P < 0.05, 0.01), and the their activities were higher than that of positive drug kojic acid. At 20 μmol/L, compounds 1, 3, 5, 14 and 21 still showed significant tyrosinase inhibitory activities (P < 0.05, 0.01).Conclusion All the compounds were isolated from R. omeiensis f. pteracantha for the first time, six compounds including 2, 6,12, 15, 17, 20 were isolated firstly from Rosa genus. Most compounds exhibited significant tyrosinase inhibitory activities, and their activities were higher than that of positive drug. Therefore, it can be inferred that the resource of the R. omeiensis f. pteracantha has high potential in the development of whitening daily necessities.
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[基金项目]
国家自然科学基金资助项目(32060081);国家自然科学基金资助项目(U1812403);贵州医科大学学术新苗项目(19NSP004);贵州省科技计划项目(黔科中引地[2022]4015)