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Biomolecules 2018, 8(4), 142; https://doi.org/10.3390/biom8040142

Synthesis of a Novel α-Glucosyl Ginsenoside F1 by Cyclodextrin Glucanotransferase and Its In Vitro Cosmetic Applications

1
Department of Oriental Medicinal Biotechnology, College of Life Science, Kyung Hee University, 1 Seocheon-dong, Giheung-gu, Yongin-si, Gyeonggi-do 17104, Korea
2
Graduate School of Biotechnology, College of Life Science, Kyung Hee University, 1 Seocheon-dong, Giheung-gu, Yongin-si, Gyeonggi-do 17104, Korea
3
K-gen (corp), 218, Gajeong-ro, Yuseong-gu, Daejeon 34129, Korea
4
Department of Herbal Crop Research, National Institute of Horticultural and Herbal Science, RDA, Eumseong 27709, Korea
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 28 August 2018 / Revised: 30 October 2018 / Accepted: 30 October 2018 / Published: 10 November 2018
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Abstract

Ginsenosides from Panax ginseng (Korean ginseng) are unique triterpenoidal saponins that are considered to be responsible for most of the pharmacological activities of P. ginseng. However, the various linkage positions cause different pharmacological activities. In this context, we aimed to synthesize new derivatives of ginsenosides with unusual linkages that show enhanced pharmacological activities. Novel α-glycosylated derivatives of ginsenoside F1 were synthesized from transglycosylation reactions of dextrin (sugar donor) and ginsenoside F1 (acceptor) by the successive actions of Toruzyme®3.0L, a cyclodextrin glucanotransferase. One of the resultant products was isolated and identified as (20S)-3β,6α,12β-trihydroxydammar-24ene-(20-O-β-D-glucopyranosyl-(1→2)-α-D-glucopyranoside) by various spectroscopic characterization techniques of fast atom bombardment-mass spectrometry (FAB-MS), infrared spectroscopy (IR), proton-nuclear magnetic resonance (1H-NMR), 13C-NMR, gradient heteronuclear single quantum coherence (gHSQC), and gradient heteronuclear multiple bond coherence (gHMBC). As expected, the novel α-glycosylated ginsenoside F1 (G1-F1) exhibited increased solubility, lower cytotoxicity toward human dermal fibroblast cells (HDF), and higher tyrosinase activity and ultraviolet A (UVA)-induced inhibitory activity against matrix metalloproteinase-1 (MMP-1) than ginsenoside F1. Since F1 has been reported as an antiaging and antioxidant agent, the enhanced efficacies of the novel α-glycosylated ginsenoside F1 suggest that it might be useful in cosmetic applications after screening. View Full-Text
Keywords: cyclodextrin glycosyltransferase; cyclodextrin glycosyltransferase (CGTase); ginsenoside F1; α-glucosyl ginsenoside F1 cyclodextrin glycosyltransferase; cyclodextrin glycosyltransferase (CGTase); ginsenoside F1; α-glucosyl ginsenoside F1
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MDPI and ACS Style

Moon, S.S.; Lee, H.J.; Mathiyalagan, R.; Kim, Y.J.; Yang, D.U.; Lee, D.Y.; Min, J.W.; Jimenez, Z.; Yang, D.C. Synthesis of a Novel α-Glucosyl Ginsenoside F1 by Cyclodextrin Glucanotransferase and Its In Vitro Cosmetic Applications. Biomolecules 2018, 8, 142.

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