Exploring gingerol glucosides with enhanced anti-inflammatory activity through a newly identified α-glucosidase (ArG) from Agrobacterium radiobacter DSM 30147.
J Biosci Bioeng
; 138(3): 218-224, 2024 Sep.
Article
de En
| MEDLINE
| ID: mdl-38997871
ABSTRACT
Gingerols are phenolic biomedical compounds found in ginger (Zingiber officinale) whose low aqueous solubility limits their medical application. To improve their solubility and produce novel glucosides, an α-glucosidase (glycoside hydrolase) from Agrobacterium radiobacter DSM 30147 (ArG) was subcloned, expressed, purified, and then confirmed to have additional α-glycosyltransferase activity. After optimization, the ArG could glycosylate gingerols into three mono-glucosides based on the length of their acyl side chains. Compound 1 yielded 63.0 %, compound 2 yielded 26.9 %, and compound 3 yielded 4.37 %. The production yield of the gingerol glucosides optimally increased in 50 mM phosphate buffer (pH 6) with 50 % (w/v) maltose and 1000 mM Li+ at 40 °C for an 24-h incubation. The structures of purified compound 1 and compound 2 were determined as 6-gingerol-5-O-α-glucoside (1) and novel 8-gingerol-5-O-α-glucoside (2), respectively, using nucleic magnetic resonance and mass spectral analyses. The aqueous solubility of the gingerol glucosides was greatly improved. Further assays showed that, unusually, 6-gingerol-5-O-α-glucoside had 10-fold higher anti-inflammatory activity (IC50 value of 15.3 ± 0.5 µM) than 6-gingerol, while the novel 8-gingerol-5-O-α-glucoside retained 42.7 % activity (IC50 value of 106 ± 4 µM) compared with 8-gingerol. The new α-glucosidase (ArG) was confirmed to have acidic α-glycosyltransferase activity and could be applied in the production of α-glycosyl derivatives. The 6-gingerol-5-O-α-glucoside can be applied as a clinical drug for anti-inflammatory activity.
Mots clés
Texte intégral:
1
Collection:
01-internacional
Base de données:
MEDLINE
Sujet principal:
Catéchols
/
Agrobacterium tumefaciens
/
Alpha-Glucosidase
/
Alcools gras
/
Glucosides
/
Anti-inflammatoires
Langue:
En
Journal:
J Biosci Bioeng
Sujet du journal:
ENGENHARIA BIOMEDICA
/
MICROBIOLOGIA
Année:
2024
Type de document:
Article
Pays d'affiliation:
Taïwan
Pays de publication:
Japon