ArticleApplied microbiology and biotechnology2024
Enzymatic synthesis of phenolic acid glucosyl esters to test activities on cholangiocarcinoma cells.
Article in Applied microbiology and biotechnology, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed, 8 citations in OpenAlex.
- Discovery of Novel Phenolic Compounds fromInternational journal of molecular sciences · 2025Article
- Production of cinnamates and benzoates glucose esters by bioconversion usingPlant biotechnology (Tokyo, Japan) · 2024Article
- Aldo-keto reductases: Role in cancer development and theranostics.Oncology research · 2024Review
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7 authors at 3 institutions in 2 countries.
Funding
Abstract
While glycoside hydrolase family 1 (GH1) enzymes mostly catalyze hydrolysis reactions, rice Os9BGlu31 preferentially catalyzes transglycosylation to transfer a glucosyl moiety to another aglycone moiety to form a new glycosylated compound through a retaining mechanism. In this study, Os9BGlu31 was used to synthesize eight phenolic acid glucosyl esters, which were evaluated for activities in cholangiocarcinoma cells. The transglycosylation products of Os9BGlu31 wild type and its mutant variants were detected, produced on a milligram scale, and purified, and their structures were characterized by NMR spectroscopy. The transglycosylation products were evaluated by antioxidant and anti-proliferative assays, followed by an anti-migration assay for the selected phenolic acid glucosyl ester. Os9BGlu31 mutants produced higher yield and activity than wild-type enzymes on phenolic acids to produce phenolic acid glucosyl esters. Among these, gallic acid glucosyl ester (β-glucogallin) had the highest antioxidant activity and anti-proliferative activity in cholangiocarcinoma cells. It also inhibited the migration of cholangiocarcinoma cells. Our study demonstrated that rice Os9BGlu31 transglucosidase is a promising enzyme for glycosylation of bioactive compounds in one-step reactions and provides evidence that β-glucogallin inhibits cell proliferation and migration of cholangiocarcinoma cells. KEY POINTS: • Os9BGlu31 transglucosidases produced phenolic acid glucosyl esters for bioactivity testing. • Phenolic acid glucosyl esters were tested for cytotoxicity in cholangiocarcinoma cells. • β-Glucogallin displayed the highest inhibition of cholangiocarcinoma cell growth.
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