Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Shenyang Pharmaceutical University, Shenyang, China.
Engineering Research Center of Natural Medicine Active Molecule Research & Development, Shenyang Pharmaceutical University, Shenyang, China.
J Food Biochem. 2022 Oct;46(10):e14304. doi: 10.1111/jfbc.14304. Epub 2022 Jul 19.
Seven pairs of enantiomeric phenylpropanoids (1a/1b-7a/7b), including eight undescribed phenylpropanoids (1a, 2a/2b, 3a, 5a, 6a/6b, and 7b) were found in the fruits of Crataegus pinnatifida Bge. The enantiomers were separated using chiral column and elucidated through various spectroscopic methods and quantum chemical ECD calculations. The tyrosinase inhibitory activity of enantiomers was tested in vitro. Among them, enantiomers 1a/1b displayed moderate tyrosinase inhibitory activities. The interaction patterns were further studied by molecular docking, and the results indicated compounds 1a/1b may bind in the active site near the copper atom and interacted with the hydrophobic areas in the active pocket. PRACTICAL APPLICATIONS: Melanins exist widely in organisms and will be produced more against environmental stresses. Without th enzymatic action of tyrosinase, melanin biosynthesis would be blocked. Thus, tyrosinase inhibitors have been developed to modulate melanin formation. In this study, the enantiomeric phenylpropanoid isolated from the fruits of C. pinnatifida Bge displayed moderate tyrosinase inhibitory activities. This work may provide foundations for further research on tyrosinase inhibitor from natural sources.
从山楂果实中发现了 7 对对映体苯丙素（1a/1b-7a/7b），包括 8 种未被描述的苯丙素（1a、2a/2b、3a、5a、6a/6b 和 7b）。使用手性柱通过各种光谱方法和量子化学 ECD 计算对非对映异构体进行了分离和阐明。在体外测试了非对映异构体的酪氨酸酶抑制活性。其中，对映异构体 1a/1b 表现出中等的酪氨酸酶抑制活性。通过分子对接进一步研究了相互作用模式，结果表明化合物 1a/1b 可能结合在靠近铜原子的活性部位，并与活性口袋中的疏水区相互作用。实际应用：黑色素广泛存在于生物体内，在环境压力下会产生更多的黑色素。如果没有酪氨酸酶的酶促作用，黑色素的生物合成就会受阻。因此，已经开发出酪氨酸酶抑制剂来调节黑色素的形成。在这项研究中，从山楂果实中分离出的对映体苯丙素表现出中等的酪氨酸酶抑制活性。这项工作可为进一步研究天然来源的酪氨酸酶抑制剂提供基础。
