Abstract
Steroidal glycosides are important sources of innovative drugs. The increased diversification of steroidal glycosides will expand the probability of discovering active molecules. It is an efficient approach to diversify steroidal glycosides by using steroidal glycosyltransferases. OcUGT1, a uridine diphosphate-d-glucose (UDP-Glc)-dependent glycosyltransferase from Ornithogalum caudatum, is a multifunctional enzyme, and its glycodiversification potential towards steroids has never been fully explored. Herein, the glycodiversification capability of OcUGT1 towards 25 steroids through glucosylation and transglucosylation reactions were explored. Firstly, each of 25 compounds was glucosylated with UDP-Glc. Under the action of OcUGT1, five steroids (testosterone, deoxycorticosterone, hydrocortisone, estradiol, and 4-androstenediol) were glucosylated to form corresponding mono-glucosides and biosides. Next, OcUGT1-mediated transglucosylation activity of these compounds with another sugar donor ortho-nitrophenyl-β-d-glucopyranoside (oNPGlc) was investigated. Results revealed that the same five steroids could be glucosylated to generate mono-glucosides and biosides by OcUGT1 through transglucosylation reactions. These data indicated that OcUGT1-assisted glycodiversification of steroids could be achieved through glucosylation and transglucosylation reactions. These results provide a way to diversify steroidal glycosides, which lays the foundation for the increase of the probability of obtaining active lead compounds.
Highlights
Steroidal glycosides (SGs) possess broad biological activities, such as anti-inflammatory effect [1,2], anticancer activity [3,4,5], antifungal property [6,7,8], and antiviral activity [9,10]
Results revealed that the same five steroids could be glucosylated to generate mono-glucosides and biosides by OcUGT1 through transglucosylation reactions. These data indicated that OcUGT1-assisted glycodiversification of steroids could be achieved through glucosylation and transglucosylation reactions
These results provide a way to diversify steroidal glycosides, which lays the foundation for the increase of the probability of obtaining active lead compounds
Summary
Steroidal glycosides (SGs) possess broad biological activities, such as anti-inflammatory effect [1,2], anticancer activity [3,4,5], antifungal property [6,7,8], and antiviral activity [9,10]. Steroidal glycosides are able to serve as the precursors of pharmaceutical steroids [11] These data indicate that steroidal glycosides are a kind of important natural products with pharmaceutical potential. The enzymatic glycodiversification is becoming a main strategy for diversifying glycosylated natural products due to the great strides made in the generation of glycosyltransferases (GTs) with catalytic promiscuity [13,14,15]. OcUGT1 was characterized to be a UDP-Glc-dependent glycosyltransferase with a catalytic flexibility, catalyzing diverse aglycons to form corresponding glycosides [23,24]. It is of great significance to carry out the research of OcUGT1 on glycodiversification of steroids for enriching the steroidal glycosides and expanding the enzymatic tools for glycodiversification of steroids. OcUGT1 may be deemed as a potential enzymatic tool for glycodiversification of steroids
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