Glycosylation of flavonoids with a glycosyltransferase from Bacillus cereus.
Microbial glycosyltransferases can convert many small lipophilic compounds such as phenolics, terpenoids, cyanohydrins and alkaloids into glycons using uridine-diphosphate-activated sugars. The main chemical functions of glycosylation processes are stabilization, detoxification and solubilization of the substrates. The gene encoding the UDP-glycosyltransferase from Bacillus cereus, BcGT-1, was cloned by PCR and sequenced. BcGT-1 was expressed in Escherichia coli BL21 (DE3) with a his-tag and purified using a His-tag affinity column. BcGT-1 could use apigenin, genistein, kaempferol, luteolin, naringenin and quercetin as substrates and gave two reaction products. The enzyme preferentially glycosylated at the 3-hydroxyl group, but it could transfer a glucose group onto the 7-hydroxyl group when the 3-hydroxyl group was not available. The reaction products made by biotransformation of flavonoids with E. coli expressing BcGT-1 are similar to those produced with the purified recombinant enzyme. Thus, this work provides a method that might be useful for the biosynthesis of flavonoid glucosides and for the glycosylation of related compounds.
Hyung Ko
Jae
J
Division of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Seoul, Korea.
Gyu Kim
Bong
B
Joong-Hoon
Ahn
A
D000595:Amino Acid Sequence; D001409:Bacillus cereus / Q000201:enzymology*; D001426:Bacterial Proteins / Q000737:chemistry / Q000378:metabolism / Q000502:physiology*; D003001:Cloning, Molecular; D004926:Escherichia coli / Q000235:genetics; D005419:Flavonoids / Q000737:chemistry / Q000378:metabolism*; D006031:Glycosylation; D016695:Glycosyltransferases / Q000737:chemistry / Q000502:physiology*; D008969:Molecular Sequence Data; D011993:Recombinant Fusion Proteins / Q000378:metabolism / Q000502:physiology; D016415:Sequence Alignment; D020539:Sequence Analysis, Protein
D001426:Bacterial Proteins; D005419:Flavonoids; D011993:Recombinant Fusion Proteins; D016695:Glycosyltransferases