Tags

Type your tag names separated by a space and hit enter

Identification of highly potent α-glucosidase inhibitory and antioxidant constituents from Zizyphus rugosa bark: enzyme kinetic and molecular docking studies with active metabolites.
Pharm Biol. 2017 Dec; 55(1):1436-1441.PB

Abstract

CONTEXT

Previous studies have shown that extracts of Zizyphus rugosa Lam. (Rhamnaceae) bark contained phytoconstituents with antidiabetic potential to lower blood glucose levels in diabetic rats. However, there has been no report on the active compounds in this plant as potential antidiabetic inhibitors.

OBJECTIVE

We evaluated the α-glucosidase inhibitory and antioxidant activities of Z. rugosa extract. Moreover, the active phytochemical constituents were isolated and characterized.

MATERIALS AND METHODS

The α-glucosidase inhibition of crude ethanol extract obtained from the bark of Z. rugosa was assayed as well as the antioxidant activity. Active compounds (1-6) were isolated, the structures were determined, and derivatives (2a-2 l) were prepared. All compounds were tested for their α-glucosidase inhibitory (yeast and rat intestine) and antioxidant (DPPH) activities.

RESULTS

The active α-glucosidase inhibitors (1-6) were isolated from Z. rugosa bark and 12 derivatives (2a-2 l) were prepared. Compound 2 showed the most powerful yeast α-glucosidase inhibitory activity (IC50 16.3 μM), while compounds 3 and 4 display only weak inhibition toward rat intestinal α-glucosidase. Moreover, compound 6 showed the most potent antioxidant activity (IC50 42.8 μM). The molecular docking results highlighted the role of the carboxyl moiety of 2 for yeast α-glucosidase inhibition through H-bonding.

DISCUSSION AND CONCLUSIONS

These results suggest the potential of Z. rugosa bark for future application in the treatment of diabetes and active compounds 1 and 2 have emerged as promising molecules for therapy.

Links

PMC Free PDF

Authors+Show Affiliations

Sichaem J
a Natural Products Research Unit, Department of Chemistry, Faculty of Science , Chulalongkorn University , Bangkok , Thailand.
Aree T
a Natural Products Research Unit, Department of Chemistry, Faculty of Science , Chulalongkorn University , Bangkok , Thailand.
Lugsanangarm K
b Program of Chemistry, Faculty of Science and Technology , Bansomdej Chaopraya Rajabhat University , Bangkok , Thailand.
Tip-Pyang S
a Natural Products Research Unit, Department of Chemistry, Faculty of Science , Chulalongkorn University , Bangkok , Thailand.

MeSH

AntioxidantsBiphenyl CompoundsEthanolGlycoside Hydrolase InhibitorsKineticsMolecular Docking SimulationPhytotherapyPicratesPlant BarkPlant ExtractsPlants, MedicinalProtein BindingProtein ConformationSaccharomyces cerevisiae ProteinsSolventsStructure-Activity RelationshipZiziphusalpha-Glucosidases

Pub Type(s)

Comparative Study
Journal Article

Language

eng

PubMed ID

28320255

Citation

Sichaem, Jirapast, et al. "Identification of Highly Potent Α-glucosidase Inhibitory and Antioxidant Constituents From Zizyphus Rugosa Bark: Enzyme Kinetic and Molecular Docking Studies With Active Metabolites." Pharmaceutical Biology, vol. 55, no. 1, 2017, pp. 1436-1441.
Sichaem J, Aree T, Lugsanangarm K, et al. Identification of highly potent α-glucosidase inhibitory and antioxidant constituents from Zizyphus rugosa bark: enzyme kinetic and molecular docking studies with active metabolites. Pharm Biol. 2017;55(1):1436-1441.
Sichaem, J., Aree, T., Lugsanangarm, K., & Tip-Pyang, S. (2017). Identification of highly potent α-glucosidase inhibitory and antioxidant constituents from Zizyphus rugosa bark: enzyme kinetic and molecular docking studies with active metabolites. Pharmaceutical Biology, 55(1), 1436-1441. https://doi.org/10.1080/13880209.2017.1304426
Sichaem J, et al. Identification of Highly Potent Α-glucosidase Inhibitory and Antioxidant Constituents From Zizyphus Rugosa Bark: Enzyme Kinetic and Molecular Docking Studies With Active Metabolites. Pharm Biol. 2017;55(1):1436-1441. PubMed PMID: 28320255.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Identification of highly potent α-glucosidase inhibitory and antioxidant constituents from Zizyphus rugosa bark: enzyme kinetic and molecular docking studies with active metabolites. AU - Sichaem,Jirapast, AU - Aree,Thammarat, AU - Lugsanangarm,Kiattisak, AU - Tip-Pyang,Santi, PY - 2017/3/22/entrez PY - 2017/3/23/pubmed PY - 2017/6/6/medline KW - Lupane-type triterpenes KW - flavonoid glycosides KW - lignan glycosides SP - 1436 EP - 1441 JF - Pharmaceutical biology JO - Pharm Biol VL - 55 IS - 1 N2 - CONTEXT: Previous studies have shown that extracts of Zizyphus rugosa Lam. (Rhamnaceae) bark contained phytoconstituents with antidiabetic potential to lower blood glucose levels in diabetic rats. However, there has been no report on the active compounds in this plant as potential antidiabetic inhibitors. OBJECTIVE: We evaluated the α-glucosidase inhibitory and antioxidant activities of Z. rugosa extract. Moreover, the active phytochemical constituents were isolated and characterized. MATERIALS AND METHODS: The α-glucosidase inhibition of crude ethanol extract obtained from the bark of Z. rugosa was assayed as well as the antioxidant activity. Active compounds (1-6) were isolated, the structures were determined, and derivatives (2a-2 l) were prepared. All compounds were tested for their α-glucosidase inhibitory (yeast and rat intestine) and antioxidant (DPPH) activities. RESULTS: The active α-glucosidase inhibitors (1-6) were isolated from Z. rugosa bark and 12 derivatives (2a-2 l) were prepared. Compound 2 showed the most powerful yeast α-glucosidase inhibitory activity (IC50 16.3 μM), while compounds 3 and 4 display only weak inhibition toward rat intestinal α-glucosidase. Moreover, compound 6 showed the most potent antioxidant activity (IC50 42.8 μM). The molecular docking results highlighted the role of the carboxyl moiety of 2 for yeast α-glucosidase inhibition through H-bonding. DISCUSSION AND CONCLUSIONS: These results suggest the potential of Z. rugosa bark for future application in the treatment of diabetes and active compounds 1 and 2 have emerged as promising molecules for therapy. SN - 1744-5116 UR - https://www.unboundmedicine.com/medline/citation/28320255/Identification_of_highly_potent_α_glucosidase_inhibitory_and_antioxidant_constituents_from_Zizyphus_rugosa_bark:_enzyme_kinetic_and_molecular_docking_studies_with_active_metabolites_ DB - PRIME DP - Unbound Medicine ER -