Enzymatic Synthesis of Puerarin Glucosides Using Cyclodextrin Glucanotransferase with Enhanced Antiosteoporosis Activity

Puerarin ( PU ) is the most abundant isoflavone from the root of Pueraria lobata and exhibits a broad range of pharmacological activities. However, poor water solubility and low bioavailability limit its use. Enzymatic transglycosylation is emerging as a new strategy to improve the pharmacodynamic a...

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Veröffentlicht in:ACS omega 2020-06, Vol.5 (21), p.12251-12258
Hauptverfasser: Huang, Wei, He, Qi, Zhou, Zhen-Ru, He, Hai-Bin, Jiang, Ren-Wang
Format: Artikel
Sprache:eng
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Zusammenfassung:Puerarin ( PU ) is the most abundant isoflavone from the root of Pueraria lobata and exhibits a broad range of pharmacological activities. However, poor water solubility and low bioavailability limit its use. Enzymatic transglycosylation is emerging as a new strategy to improve the pharmacodynamic and pharmacokinetic properties of natural products for drug development. In this study, three PU glucosides ( PU-G , PU-2G , and PU-3G ) were synthesized by using a cyclodextrin glucanotransferase from Bacillus licheniformis with PU as the acceptor and α-cyclodextrin as the sugar donor. The transglycosylation products were isolated and structurally identified by mass spectrometry and nuclear magnetic resonance. The water solubilities of PU-G , PU-2G , and PU-3G were 15.6, 100.9, and 179.1 times higher than that of PU , respectively. Moreover, the antiosteoporosis activities of these glucosides were tested, and PU-G was found to show much more potent antiosteoporosis activity as compared to the original PU .
ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.0c00950