Tyrosinase Inhibition Activities of Depsides Isolated from Ramalina Species

Pub Date : 2023-05-04 DOI:10.1080/22311866.2023.2236052

B. Marasini, J. Yue, Erendra Manandhar, Rejina Rai, Uddav Khadka, M. Manandhar, S. Shyaula

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Abstract

Abstract Three depsides, namely sekikaic acid (1), homosekikaic acid (2), and 4′-O-demethylsekikaic acid (3) were isolated from acetone fraction of Ramalina spp. The structures were characterized by using spectroscopic techniques like 1H NMR, 13C NMR, ESI MS and IR. The quantitative determinations of these compounds were conducted by reversed phase high performance liquid chromatography with photodiode array detector (LC-PDA). The developed assay method could be considered as a suitable quality control method for Ramalina spp. The content on percentage dry basis of these compounds were 1.39%, 0.98% and 0.58% for compound 1, 2 and 3, respectively. It is the first time report for tyrosinase inhibition activity for depsides. All of these compounds exhibited inhibition for tyrosinase enzyme with the IC50 values 110.3±3.5, 90.1±1.4, and 206.4±5.1 µg/mL by the compounds 1, 2 and 3, respectively. The structure activity relationship of despides showed that the methoxy group at ring A might have enhanced the inhibitory activity. Therefore, these compounds may have their potential use in cosmetics with further studies. GRAPHICAL ABSTRACT

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拉玛林种分离物对酪氨酸酶的抑制作用

摘要从Ramalina spp.丙酮馏分中分离得到三个糖苷，即sekikaic acid（1）、homosekikaic cid（2）和4′-O-去甲基sekikaid acid（3）。利用1H NMR、13C NMR、ESI-MS和IR等光谱技术对其结构进行了表征。采用反相高效液相色谱-光电二极管阵列检测器（LC-PDA）对这些化合物进行定量测定。所开发的测定方法可被认为是一种适合Ramalina spp.的质量控制方法。化合物1、2和3的这些化合物的干基含量分别为1.39%、0.98%和0.58%。这是首次报道对去肽的酪氨酸酶抑制活性。所有这些化合物对酪氨酸酶均表现出抑制作用，化合物1、2和3的IC50值分别为110.3±3.5、90.1±1.4和206.4±5.1µg/mL。二硫化物的结构-活性关系表明，A环上的甲氧基可能增强了其抑制活性。因此，随着研究的深入，这些化合物可能在化妆品中具有潜在的应用前景。图形摘要

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