Transglycosylation of Hydroquinone and Epicatechin by .BETA.-Fructofuranosidase from Arthrobacter sp.

Nakano, Hirofumi; Hamayasu, Kenichi; Nakagawa, Kaname; Tabata, Akinori; Fujita, Katsuhide; Hara, Kozo; Kiso, Taro; Murakami, Hiromi; Kitahata, Sumio

doi:10.5458/jag.49.115

Cited by 11 publications

(6 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thus, the structural modification of EGCG to develop new compounds with increased solubility and stability is highly desirable. As illustrated in the literature [13,22,23,24,25], the glycosylated derivatives of catechins exhibited similar antioxidant properties, increased solubility in water and stronger tyrosinase inhibitory effects. Thus, the transglycosylated derivatives of EGCG are important for their utility as food additives and cosmetics.…”

Section: Introductionmentioning

confidence: 82%

Synthesis and Biological Testing of Novel Glucosylated Epigallocatechin Gallate (EGCG) Derivatives

Zhang

Wang

et al. 2016

Molecules

View full text Add to dashboard Cite

Epigallocatechin gallate (EGCG) is the most abundant component of green tea catechins and has strong physiological activities. In this study, two novel EGCG glycosides (EGCG-G1 and EGCG-G2) were chemoselectively synthesized by a chemical modification strategy. Each of these EGCG glycosides underwent structure identification, and the structures were assigned as follows: epigallocatechin gallate-4 11 -O-β-D-glucopyranoside (EGCG-G1, 2) and epigallocatechin gallate-4 1 ,4 11 -O-β-D-gluco-pyranoside (EGCG-G2, 3). The EGCG glycosides were evaluated for their anticancer activity in vitro against two human breast cell lines (MCF-7 and MDA-MB-231) using MTT assays. The inhibition rate of EGCG glycosides (EGCG-G1 and EGCG-G2) is not obvious. The EGCG glycosides are more stable than EGCG in aqueous solutions, but exhibited decreasing antioxidant activity in the DPPH radical-scavenging assay (EGCG > EGCG-G2 > EGCG-G1). Additionally, the EGCG glycosides exhibited increased water solubility: EGCG-G2 and EGCG-G1 were 15 and 31 times as soluble EGCG, respectively. The EGCG glycosides appear to be useful, and further studies regarding their biological activity are in progress.

show abstract

Section: Introductionmentioning

confidence: 82%

Synthesis and Biological Testing of Novel Glucosylated Epigallocatechin Gallate (EGCG) Derivatives

Zhang

Wang

et al. 2016

Molecules

View full text Add to dashboard Cite

show abstract

“…About 2-3 mg of the purified EGCG glycosides was dissolved in DMSO-d 6 (250 µL) and then placed into 3 mm NMR tubes. The NMR spectra were obtained on a Unity Inova 500 spectrometer (Varian Inc.), operating at 500 MHz for 1 H and at 125 MHz for 13 C, at 25 °C. Linkages between EGCG and glucose were evaluated using the spectra obtained via homonuclear (35).…”

Section: Methodsmentioning

confidence: 99%

“…To overcome this problem, a great deal of research has been done concerning the glycosylations of a variety of polyphenols ( − ). The resultant transglycosylated compounds have sometimes exhibited increased solubility in water, increased stability against light or oxidation, improved taste qualities, and stronger tyrosinase inhibitory effects ( − ). When improved in such ways, glycosylated bioactive substances have proven to be much more useful as food additives and cosmetics.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure Analyses, and Characterization of Novel Epigallocatechin Gallate (EGCG) Glycosides Using the Glucansucrase from Leuconostoc mesenteroides B-1299CB

Moon

Lee

Ahn

et al. 2006

J. Agric. Food Chem.

View full text Add to dashboard Cite

In this study, three epigallocatechin gallate glycosides were synthesized by the acceptor reaction of a glucansucrase produced by Leuconostoc mesenteroides B-1299CB with epigallocatechin gallate (EGCG) and sucrose. Each of these glycosides was then purified, and the structures were assigned as follows: epigallocatechin gallate 7-O-alpha-D-glucopyranoside (EGCG-G1); epigallocatechin gallate 4'-O-alpha-D-glucopyranoside (EGCG-G1'); and epigallocatechin gallate 7,4'-O-alpha-D-glucopyranoside (EGCG-G2). One of these compounds (EGCG-G1) was a novel compound. The EGCG glycosides exhibited similar or slower antioxidant effects, depending on their structures (EGCG > or = EGCG-G1 > EGCG-G1' > EGCG-G2), and also manifested a higher degree of browning resistance than was previously noted in EGCG. Also, EGCG-G1, EGCG-G1', and EGCG-G2 were 49, 55, and 114 times as water soluble, respectively, as EGCG.

show abstract

“…Glycosylation process is a very common and key structural modification for enhancement of light and oxidation stability. This process improves hydrophilicity, pharmacokinetic, and physicochemical properties of bioactive phenolic substances (Nakano et al, 2002). In a study, Li et al designed a complex of arbutin and hydroxypropyl-β-cyclodextrin.…”

Section: Antiapoptotic Role and Radioprotectormentioning

confidence: 99%

A comprehensive review of the therapeutic potential of α‐arbutin

Saeedi

Khezri

Zakaryaei

et al. 2021

Phytotherapy Research

View full text Add to dashboard Cite

Cosmetic dermatology preparations such as bleaching agents are ingredients with skin‐related biological activities for increasing and improving skin beauty. The possibility of controlling skin hyperpigmentation disorders is one of the most important research goals in cosmetic preparations. Recently, cosmetics containing herbal and botanical ingredients have attracted many interests for consumers of cosmetic products because these preparations are found safer than other preparations with synthetic components. However, high‐quality trial studies in larger samples are needed to confirm safety and clinical efficacy of phytotherapeutic agents with high therapeutic index. Arbutin (p‐hydroxyphenyl‐β‐d‐glucopyranoside) is a bioactive hydrophilic polyphenol with two isomers including alpha‐arbutin (4‐hydroxyphenyl‐α‐glucopyranoside) and β‐arbutin (4‐hydroxyphenyl‐β‐glucopyranoside). It is used as a medicinal plant in phytopharmacy. Studies have shown that alpha‐arbutin is 10 times more effective than natural arbutin. A comparison of IC50 values showed that α‐arbutin (with concentration 2.0 mM) has a more potent inhibitory activity on human tyrosinase against natural arbutin (with higher concentration than 30 mM). A review of recent studies showed that arbutin could be beneficial in treatment of various diseases such as hyperpigmentation disorders, types of cancers, central nervous system disorders, osteoporosis, diabetes, etc. This study was designed to describe the therapeutic efficiencies of arbutin.

show abstract

Transglycosylation of Hydroquinone and Epicatechin by .BETA.-Fructofuranosidase from Arthrobacter sp.

Cited by 11 publications

References 9 publications

Synthesis and Biological Testing of Novel Glucosylated Epigallocatechin Gallate (EGCG) Derivatives

Synthesis and Biological Testing of Novel Glucosylated Epigallocatechin Gallate (EGCG) Derivatives

Synthesis, Structure Analyses, and Characterization of Novel Epigallocatechin Gallate (EGCG) Glycosides Using the Glucansucrase from Leuconostoc mesenteroides B-1299CB

A comprehensive review of the therapeutic potential of α‐arbutin

Contact Info

Product

Resources

About