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Anti-tyrosinase properties of different species of turmeric and isolation of active compounds from Curcuma amada
Medicinal Chemistry Research ( IF 2.6 ) Pub Date : 2021-07-17 , DOI: 10.1007/s00044-021-02764-z
Jesmin Akter 1 , Md. Zahorul Islam 1, 2 , Md. Amzad Hossain 1 , Kensaku Takara 1
Affiliation  

Turmeric is traditionally used as a skin cosmetic in some religious and cultural occasions on the Indian subcontinent. In this study, we compared the tyrosinase inhibitory properties of four Curcuma spp., namely, C. xanthorrhiza, C. aromatica, C. amada, and C. zedoaria. Bioassay-guided isolation and purification of tyrosinase inhibitors using silica gel column and high-performance liquid chromatography. Structural identification of the compounds was conducted using 1H NMR, 13C NMR, and liquid chromatography-tandem mass spectrometry. C. amada showed the highest tyrosinase inhibitory activity, with an IC50 of 53.4 μg/mL. Therefore, it was chosen for the isolation and purification of tyrosinase inhibitors. The purified compounds were zederone (1), furanodienone (2), 1,5-epoxy-3-hydroxy-1-(3,4-dihydroxy-5-methoxyphenyl)-7-(4-hydroxyphenyl) heptanes (3), 3,5-dihydroxy-1-(3,4-dihydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl) heptanes (4) and 1,5-epoxy-3-hydroxy-1-(3,4-dihydroxy-5-methoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl) heptanes (5). The IC50 values for the mushroom anti-tyrosinase activity of compounds 1, 2, 3, 4, and 5 were 108.2, 89.2, 92.3, 21.7, and 41.3 µM, respectively. These compounds also inhibited intracellular tyrosinase activity, thus reducing melanin synthesis in B16F10 melanoma cells. Compound 4 showed significantly stronger anti-tyrosinase activity than that of arbutin (a positive control drug). No significant difference was observed in the tyrosinase inhibitory effect between compound 5 and arbutin. Our findings strongly suggest that C. amada is a promising source of natural tyrosinase inhibitors to prevent melanogenesis and could be used as a whitening cosmetic.



中文翻译:

不同种类姜黄的抗酪氨酸酶特性及从姜黄中分离活性化合物

姜黄传统上在印度次大陆的一些宗教和文化场合用作皮肤化妆品。在这项研究中,我们比较了四种酪氨酸酶抑制特性莪术属,即C.黄根C.郁金,C. AMADA,和C. zedoaria。使用硅胶柱和高效液相色谱法对酪氨酸酶抑制剂进行生物测定引导的分离和纯化。使用1 H NMR、13 C NMR和液相色谱-串联质谱法进行化合物的结构鉴定。C. amada显示出最高的酪氨酸酶抑制活性,IC 5053.4 μg/mL。因此,它被选择用于酪氨酸酶抑制剂的分离和纯化。纯化的化合物是泽德酮(1)、呋喃烯酮(2)、1,5-环氧-3-羟基-1-(3,4-二羟基-5-甲氧基苯基)-7-(4-羟基苯基)庚烷(3)、 3,5-二羟基-1-(3,4-二羟基苯基)-7-(4-羟基-3-甲氧基苯基)庚烷(4)和 1,5-环氧-3-羟基-1-(3,4-二羟基-5-甲氧基苯基)-7-(4-羟基-3-甲氧基苯基)庚烷(5)。该IC 50为化合物的蘑菇抗酪氨酸酶活性值1234,和5分别为 108.2、89.2、92.3、21.7 和 41.3 µM。这些化合物还抑制细胞内酪氨酸酶活性,从而减少 B16F10 黑色素瘤细胞中黑色素的合成。与熊果苷(阳性对照药物)相比,化合物4显示出明显更强的抗酪氨酸酶活性。在化合物5和熊果苷之间没有观察到酪氨酸酶抑制作用的显着差异。我们的研究结果强烈表明,C. amada是一种很有前途的天然酪氨酸酶抑制剂来源,可防止黑色素生成,并可用作美白化妆品。

更新日期:2021-07-18
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