- Efficient enzymatic synthesis and antibacterial activity of andrographolide glycoside
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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.
- Qiao, Ying,Huang, Yao,Feng, Fang,Chen, Zhi-Gang
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- Glucosyltransferase Capable of Catalyzing the Last Step in Neoandrographolide Biosynthesis
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ApUGT, a diterpene glycosyltransferase from Andrographis paniculata, could transfer a glucose to the C-19 hydroxyl moiety of andrograpanin to form neoandrographolide. This glycosyltransferase has a broad substrate scope, and it can glycosylate 26 natural and unnatural compounds of different structural types. This study provides a basis for exploring the glycosylation mechanism of ent-labdane-type diterpenes and plays an important role in diversifying the structures used in drug discovery.
- Li, Yuan,Lin, Hui-Xin,Wang, Jian,Yang, Jian,Lai, Chang-Jiang-Sheng,Wang, Xing,Ma, Bao-Wei,Tang, Jin-Fu,Li, Yong,Li, Xin-Lin,Guo, Juan,Gao, Wei,Huang, Lu-Qi
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p. 5999 - 6002
(2018/10/20)
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