期刊
CARBOHYDRATE RESEARCH
卷 494, 期 -, 页码 -出版社
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2020.108078
关键词
Arbutin derivatives; Amylomaltase; 4-alpha-glucanotransferase; Transglycosylation; Tyrosinase inhibitor; Skin-whitening agent
资金
- Thammasat University Research Fund [TUGR 2/37/2562]
- Phramongkutklao College of Medicine Research Fund
alpha-Arbutin is widely used as a skin-whitening agent in the pharmaceutical and cosmetic industries because of its inhibitory effect on tyrosinase, an important enzyme for generating melanin pigments. Given the increasing demand for such products, we synthesized alpha-and beta-arbutin-alpha-D-glycosides through transglycosylation reactions catalyzed by a recombinant amylomaltase, using tapioca starch and alpha-and beta-arbutin as donor and acceptor molecules, respectively. The catalytic yield of products by the amylomaltase was greater with alpha-arbutin than with beta-arbutin. The highest glycoside yield (83%) was achieved by adjusting the following six parameters: starch and alpha-arbutin concentration, enzyme concentration, pH, temperature, and incubation time. The glycoside products were isolated and analyzed by HPLC, and two major products were identified by mass spectrometry and nuclear magnetic resonance spectroscopy, namely, alpha-arbutin-alpha-D-glucopyranoside (alpha-Ab-alpha-G(1)) and alpha-arbutin-alpha-D-maltopyranoside (alpha-Ab-alpha-G(2)). Both alpha-Ab-alpha-G(1) and alpha-Ab-alpha-G(2) are more water soluble than alpha-arbutin. Like alpha-arbutin, alpha-Ab-alpha-G(1) and alpha-Ab-alpha-G(2) showed competitive inhibition of human tyrosinase. However, their K-i values were 0.53 and 1.40 mM, respectively, which are slightly higher than that of alpha-arbutin (0.25 mM). The addition of glucosyl residues to alpha-arbutin improved its water solubility. Therefore, alpha-Ab-alpha-G(1) and alpha-Ab-alpha-G(2) could be easily absorbed by the skin and used as skin-whitening agents in pharmaceutical and cosmetic industries.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据