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Efficient enzymatic synthesis and antibacterial activity of andrographolide glycoside

Paper ID Volume ID Publish Year Pages File Format Full-Text
34262 45013 2016 6 PDF Available
Title
Efficient enzymatic synthesis and antibacterial activity of andrographolide glycoside
Abstract

•Enzymatic galactosylation of andrographolide in co-solvents was carried out.•β-Galactosidase displayed high regioselectivity and stability in 5–15% DMSO–PBS.•Andrographolide glycoside has higher solubility in water than andrographolide.•Antibacterial activities of glycoside were higher than those of andrographolide.

19-O-β-Galactosyl andrographolide, a potential novel antibacterial agent, was synthesized through enzymatic transgalactosylation of andrographolide in co-solvent systems. Organic solvents and their contents have important influences on the regioselective galactosylation of andrographolide catalyzed by β-galactosidase from bovine liver in co-solvent systems. β-Galactosidase showed high activity and stability in 5–15% (v/v) DMSO with 22–52% total molar yields of andrographolide glycosides. The addition of hydrophilic DMSO not only greatly promoted the solubility of the substrate, but also improved the reaction efficiency of the process. β-Galactosidase displayed absolute regioselectivity toward the 19-position of andrographolide. The solubility of andrographolide glycoside in water was 42.1 mg ml−1, which is about 702 times that of andrographolide. The glycosylated andrographolide showed antibacterial activity against five representative species of food-borne pathogenic bacteria [with minimal inhibitory concentrations (MICs) as low as 8 μg ml−1], whereas andrographolide exhibited no such activity. These results indicate an enzymatic modification was not only facile and green, but an effective method for the preparation of an andrographolide monoglycoside.

Graphical abstractEnzymatic regioselective galactosylation of andrographolide catalyzed by β-galactosidase from bovine liver.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Andrographolide; β; -Galactosidase; Glycosylation; Regioselectivity; Organic solvent; Antibacterial activity
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Efficient enzymatic synthesis and antibacterial activity of andrographolide glycoside
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Publisher
Database: Elsevier - ScienceDirect
Journal: Process Biochemistry - Volume 51, Issue 5, May 2016, Pages 675–680
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us