Biotransformation of β-amyrin acetate by Rhodobacter sphaeroides

Guan-e, Yang; Zhang, Zhaoming; Bai, Hongjun; Gong, Jie; Wang, Yufen; Li, Baozhen; Li, Jiankuan

doi:10.1263/jbb.105.558

Cited by 15 publications

(9 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Additionally, the glycosylation of bioactive compounds can enhance their water-solubility, physicochemical stability, intestinal absorption, and biological half-life, and improve their bio-and pharmacological properties. [11][12][13][14][15][16][17][18] We recently reported that cultured cells of Phytolacca americana had high potential for the glucosylation of resveratrol, and that the glucosyltransferase from P. americana expressed in recombinant Escherichia coli catalyzed the glucosylation of stilbene compounds such as resveratrol. 19) Recently, an assay to measure hydrophilic antioxidant activity against ROS was developed based on the detection of chemical damage to β-phycoerythrins (PEs) through the decrease in their fluorescence emission.…”

mentioning

confidence: 99%

Synthesis, oxygen radical absorbance capacity, and tyrosinase inhibitory activity of glycosides of resveratrol, pterostilbene, and pinostilbene

Uesugi

Hamada

Shimoda

et al. 2017

Bioscience, Biotechnology, and Biochemistry

View full text Add to dashboard Cite

The stilbene compound resveratrol was glycosylated to give its 4'-O-β-D-glucoside as the major product in addition to its 3-O-β-D-glucoside by a plant glucosyltransferase from Phytolacca americana expressed in recombinant Escherichia coli. This enzyme transformed pterostilbene to its 4'-O-β-D-glucoside, and converted pinostilbene to its 4'-O-β-D-glucoside as a major product and its 3-O-β-D-glucoside as a minor product. An analysis of antioxidant capacity showed that the above stilbene glycosides had lower oxygen radical absorbance capacity (ORAC) values than those of the corresponding stilbene aglycones. The 3-O-β-D-glucoside of resveratrol showed the highest ORAC value among the stilbene glycosides tested, and pinostilbene had the highest value among the stilbene compounds. The tyrosinase inhibitory activities of the stilbene aglycones were improved by glycosylation; the stilbene glycosides had higher activities than the stilbene aglycones. Resveratrol 3-O-β-D-glucoside had the highest tyrosinase inhibitory activity among the stilbene compounds tested.

show abstract

mentioning

confidence: 99%

Synthesis, oxygen radical absorbance capacity, and tyrosinase inhibitory activity of glycosides of resveratrol, pterostilbene, and pinostilbene

Uesugi

Hamada

Shimoda

et al. 2017

Bioscience, Biotechnology, and Biochemistry

View full text Add to dashboard Cite

show abstract

“…The glycosylation of bioactive compounds can enhance their water-solubility, physicochemical stability, intestinal absorption, and biological half-life, and improve their bio-and pharmacological properties. [11][12][13][14][15][16][17][18] We report here the syntheses of glycosides of resveratrol, pterostilbene, and piceatannol by biocatalytic glycosylation using cultured cells of Phytolacca americana and cyclodextrin glucanotransferase (CGTase). In addition, we report the physiological properties of resveratrol, pterostilbene, piceatannol, and their glycosides, such as their 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical-scavenging, anti-allergic, and phosphodiesterase (PDE) inhibitory activities.…”

mentioning

confidence: 99%

Synthesis of glycosides of resveratrol, pterostilbene, and piceatannol, and their anti-oxidant, anti-allergic, and neuroprotective activities

Sato

Shimizu

et al. 2014

Bioscience, Biotechnology, and Biochemistry

View full text Add to dashboard Cite

Resveratrol was glucosylated to its 3- and 4′-β-glucosides by cultured cells of Phytolacca americana. On the other hand, cultured P. americana cells glucosylated pterostilbene to its 4′-β-glucoside. P. americana cells converted piceatannol into its 4′-β-glucoside. The 3- and 4′-β-glucosides of resveratrol were further glucosylated to 3- and 4′-β-maltosides of resveratrol, 4′-β-maltoside of which is a new compound, by cyclodextrin glucanotransferase. Resveratrol 3-β-glucoside and 3-β-maltoside showed low 2,2-diphenyl-1-picrylhydrazyl free-radical-scavenging activity, whereas other glucosides had no radical-scavenging activity. Piceatannol 4′-β-glucoside showed the strongest inhibitory activity among the stilbene glycosides towards histamine release from rat peritoneal mast cells. Pterostilbene 4′-β-glucoside showed high phosphodiesterase inhibitory activity.

show abstract

“…Many studies on glycosylation of exogenously added phenol compounds to their ␤-glucosides by cultured plant cells have been reported since Pilgrim's paper. [11][12][13][16][17][18][19][21][22][23] For example, it has been reported that cultured plant cells of Eucalyptus perriniana converted exogenously administered ␤-thujaplicin (4-isopropyltropolone) into ␤-glucosides of ␤-thujaplicin. 21 ␤-Thujaplicin formed a tautomeric mixture of 4-and 6-isopropyltropolones before glycosylation, and the corresponding ␤-glucosides of these compounds were produced by glycosylation with E. perriniana cells.…”

Section: Synthesis Of Monoglucosides Of Resveratrol Pterostilbene Amentioning

confidence: 99%

“…Furthermore, the biocatalytic glycosylation of exogenously added organic compounds can improve their water solubility, stability, and absorption after oral administration and increase their biological and pharmacological activities. [12][13][14][15][16][17][18][19] Here we describe published work showing the syntheses of monoglucosides (␤-glucosides) and/or diglycosides (␤-maltosides) of resveratrol, pterostilbene, and piceatannol by glycosylation with cultured plant cells of Phytolacca americana, glucosyltransferase (PaGT), and cyclodextrin glucanotransferase (CGTase). We also describe the pharmacological action of glycosides of resveratrol, pterostilbene, and piceatannol, such as their antioxidant (2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical-scavenging), antiallergic (antihistamine), and phosphodiesterase (PDE)-inhibitory activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and pharmacological evaluation of glycosides of resveratrol, pterostilbene, and piceatannol

Shimoda

Kubota

Uesugi

et al. 2015

Annals of the New York Academy of Sciences

View full text Add to dashboard Cite

To enhance their water solubility and pharmacological activities, the stilbenes resveratrol, pterostilbene, and piceatannol were glycosylated to their monoglucosides (β-glucosides) and diglycosides (β-maltosides) by cultured cells and cyclodextrin glucanotransferase (CGTase). Cultured cells of Phytolacca americana and glucosyltransferase (PaGT) were capable of glucosylation of resveratrol to its 3- and 4'-β-glucosides. Pterostilbene was slightly transformed into its 4'-β-glucoside by P. americana cells. Piceatannol was readily converted into piceatannol 4'-β-glucoside, with the highest yield among the three substrates. The 3- and 4'-β-glucosides of resveratrol were subjected to further glycosylation by CGTase to give 3- and 4'-β-maltoside derivatives. The inhibitory action of resveratrol and pterostilbene toward histamine release induced with compound 48/80 from rat peritoneal mast cells was improved by β-glucosylation and/or β-maltosylation (i.e., the inhibitory activity for histamine release of the 3- and 4'-β-glucosides of resveratrol, the 3- and 4'-β-maltosides of resveratrol, and the 4'-β-glucoside of pterostilbene was higher than that of the corresponding aglycones, resveratrol and pterostilbene, respectively). In addition, the phosphodiesterase (PDE) inhibitory activity of resveratrol and pterostilbene was enhanced by β-glucosylation and/or β-maltosylation (i.e., the PDE inhibitory activities of the 3- and 4'-β-glucosides of resveratrol, the 4'-β-maltoside of resveratrol, and the 4'-β-glucoside of pterostilbene were higher than those of the corresponding aglycones, resveratrol and pterostilbene, respectively).

show abstract

Biotransformation of β-amyrin acetate by Rhodobacter sphaeroides

Cited by 15 publications

References 17 publications

Synthesis, oxygen radical absorbance capacity, and tyrosinase inhibitory activity of glycosides of resveratrol, pterostilbene, and pinostilbene

Synthesis, oxygen radical absorbance capacity, and tyrosinase inhibitory activity of glycosides of resveratrol, pterostilbene, and pinostilbene

Synthesis of glycosides of resveratrol, pterostilbene, and piceatannol, and their anti-oxidant, anti-allergic, and neuroprotective activities

Synthesis and pharmacological evaluation of glycosides of resveratrol, pterostilbene, and piceatannol

Contact Info

Product

Resources

About