A Flavone-5-O-glycosyltransferase Obtained through Domain Shuffling and Its Application in the Bioproduction of Luteolin-5-O-glucoside

Luteolin-5-O-glucoside is a rare luteolin glycoside compound with enormous potential for application. In order to promote sustainability and a circular economy, environmentally friendly catalysts and catalytic processes are in demand to produce luteolin-5-O-glucoside. Using glycosyltransferase transformation is an efficient method for synthesizing glycosylated flavonoids. However, most reported glycosyltransferases have not been able to catalyze glycosylation on the 5-OH site, and a method for the sustainable production of luteolin-5-O-glucoside has not been established. In this paper, a glycosyltransferase DoUGT71A15 was cloned from Dichanthelium oligosanthes. The N-terminal fragment of ZmUGT707A8 (Met1–Met93) was inserted into the N-terminus of DoUGT71A15 by domain shuffling, and a biological catalyst ZmDo was obtained. ZmDo could convert luteolin to luteolin-5-O-glucoside with Km and kcat/Km values of 0.13 mM and 1355.8 s–1·M–1, respectively. Then, the catalytic mechanism of region selectivity of ZmDo was studied by using bioinformatics methods, and the key site E89 was identified through alanine scanning. Finally, the strain BSZ containing the UDPG circulatory system, which could use cellobiose as a substrate and recycle UDP to synthesize UDPG, was used for efficient production of luteolin-5-O-glucoside, with a yield of 2253 mg/L and a molar conversion rate of 95.8%. This research obtained a novel flavone-5-OH glycosyltransferase and produced luteolin-5-O-glucoside by bioconversion, which provided the possibility for sustainable production and application of luteolin-5-O-glucoside.

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Publication Details

Journal
ACS Sustainable Chemistry & Engineering
Published
2024-10-07
DOI
https://doi.org/10.1021/acssuschemeng.4c04277
Citations
5
Primary Topic
Natural product bioactivities and synthesis
Type
article
Field-Weighted Citation Impact
1.17

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article

A Flavone-5-O-glycosyltransferase Obtained through Domain Shuffling and Its Application in the Bioproduction of Luteolin-5-O-glucoside

Linguo Zhao, Qiqi Xing, Shutong Jia, Changning Lu et al.
5 citations
ACS Sustainable Chemistry & Engineering
Natural product bioactivities and synthesis
1.17
article

A Flavone-5-O-glycosyltransferase Obtained through Domain Shuffling and Its Application in the Bioproduction of Luteolin-5-O-glucoside

Linguo Zhao, Qiqi Xing, Shutong Jia, Changning Lu, Zhenzhong Wang, Qi Li, H. Wang
article en
5 citations

Abstract

Luteolin-5-O-glucoside is a rare luteolin glycoside compound with enormous potential for application. In order to promote sustainability and a circular economy, environmentally friendly catalysts and catalytic processes are in demand to produce luteolin-5-O-glucoside. Using glycosyltransferase transformation is an efficient method for synthesizing glycosylated flavonoids. However, most reported glycosyltransferases have not been able to catalyze glycosylation on the 5-OH site, and a method for the sustainable production of luteolin-5-O-glucoside has not been established. In this paper, a glycosyltransferase DoUGT71A15 was cloned from Dichanthelium oligosanthes. The N-terminal fragment of ZmUGT707A8 (Met1–Met93) was inserted into the N-terminus of DoUGT71A15 by domain shuffling, and a biological catalyst ZmDo was obtained. ZmDo could convert luteolin to luteolin-5-O-glucoside with Km and kcat/Km values of 0.13 mM and 1355.8 s–1·M–1, respectively. Then, the catalytic mechanism of region selectivity of ZmDo was studied by using bioinformatics methods, and the key site E89 was identified through alanine scanning. Finally, the strain BSZ containing the UDPG circulatory system, which could use cellobiose as a substrate and recycle UDP to synthesize UDPG, was used for efficient production of luteolin-5-O-glucoside, with a yield of 2253 mg/L and a molar conversion rate of 95.8%. This research obtained a novel flavone-5-OH glycosyltransferase and produced luteolin-5-O-glucoside by bioconversion, which provided the possibility for sustainable production and application of luteolin-5-O-glucoside.

ACS Sustainable Chemistry & EngineeringVol. 12(42)
Nanjing Forestry University (CN), Kanion Pharmaceutical (China) (CN)
National Key Research and Development Program of China
Clean water and sanitation
Openalex Percentile: Top 22%
Natural product bioactivities and synthesis
1.17
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