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- Title
High-yield enzymatic bioconversion of hydroquinone to α-arbutin, a powerful skin lightening agent, by amylosucrase.
- Authors
Seo, Dong-Ho; Jung, Jong-Hyun; Ha, Suk-Jin; Cho, Hyun-Kug; Jung, Dong-Hyun; Kim, Tae-Jip; Baek, Nam-In; Yoo, Sang-Ho; Park, Cheon-Seok
- Abstract
α-Arbutin (α-Ab) is a powerful skin whitening agent that blocks epidermal melanin biosynthesis by inhibiting the enzymatic oxidation of tyrosine and l-3,4-dihydroxyphenylalanine ( l-DOPA). α-Ab was effectively synthesized from hydroquinone (HQ) by enzymatic biotransformation using amylosucrase (ASase). The ASase gene from Deinococcus geothermalis (DGAS) was expressed and efficiently purified from Escherichia coli using a constitutive expression system. The expressed DGAS was functional and performed a glycosyltransferase reaction using sucrose as a donor and HQ as an acceptor. The presence of a single HQ bioconversion product was confirmed by thin-layer chromatography (TLC) and high-performance liquid chromatography (HPLC). The HQ bioconversion product was isolated by silica gel open column chromatography and its chemical structure determined by H and C nuclear magnetic resonance (NMR). The product was determined to be hydroquinone- O-α- d-glucopyranoside with a glucose molecule linked to HQ through an α-glycosidic bond. However, the production yield of the transfer reaction was significantly low (1.3%) due to the instability of HQ in the reaction mixture. The instability of HQ was considerably improved by antioxidant agents, particularly ascorbic acid, implying that HQ is labile to oxidation. A maximum yield of HQ transfer product of 90% was obtained at a 10:1 molar ratio of donor (sucrose) and acceptor (HQ) molecules in the presence of 0.2 mM ascorbic acid.
- Subjects
BIOCONVERSION; ARBUTIN; HYDROQUINONE; FADE creams (Cosmetics); MELANOGENESIS; TYROSINE; LIQUID chromatography
- Publication
Applied Microbiology & Biotechnology, 2012, Vol 94, Issue 5, p1189
- ISSN
0175-7598
- Publication type
Article
- DOI
10.1007/s00253-012-3905-7