Antioxidative and α-glucosidase inhibitory constituents of Polyscias guilfoylei: experimental and computational assessments

Searching for bioactive agents from medicinal plants, eleven constituents were isolated from Polyscias guilfoylei stem for the first time, including a nucleoside uracil ( 1 ), two sterols β-sitosterol ( 2 ) and daucosterol ( 3 ), a saponin androseptoside A ( 4 ), two lignans (+)-pinoresinol ( 5 ) an...

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Published in:Molecular diversity 2022-02, Vol.26 (1), p.229-243
Main Authors: Anh, Le Thi Tu, Son, Ninh The, Van Tuyen, Nguyen, Thuy, Phan Thi, Quan, Pham Minh, Ha, Nguyen Thi Thu, Tra, Nguyen Thanh
Format: Article
Language:English
Subjects:
alpha-Glucosidases - metabolism
Antioxidants - chemistry
Antioxidants - pharmacology
Araliaceae - metabolism
Binding sites
Biochemistry
Biomedical and Life Sciences
Flavonoids
Glycoside Hydrolase Inhibitors - chemistry
Glycoside Hydrolase Inhibitors - pharmacology
Humans
Life Sciences
Molecular Docking Simulation
Organic Chemistry
Original Article
Pharmacy
Polymer Sciences
Sterols
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Summary:Searching for bioactive agents from medicinal plants, eleven constituents were isolated from Polyscias guilfoylei stem for the first time, including a nucleoside uracil ( 1 ), two sterols β-sitosterol ( 2 ) and daucosterol ( 3 ), a saponin androseptoside A ( 4 ), two lignans (+)-pinoresinol ( 5 ) and (+)-syringaresinol ( 6 ), four phenolic acids protocatechuic acid ( 7 ), methyl protocatechuate ( 8 ), caffeic acid ( 9 ), and 5- O -caffeoylquinic acid ( 10 ), and a flavonoid quercitrin ( 11 ). Metabolites 1 , 4 , and 6–11 have never been observed in genus Polyscias before. Phenolic compounds 7 and 9 possessed the respective IC 50 values of 21.33 and 13.88 µg/mL in DPPH (2,2-diphenyl-1-picrylhydrazyl) antioxidative assay, as compared with that of the positive control resveratrol (IC 50  = 13.21 µg/mL). From density functional theory (DFT) calculated approach, the DPPH free radical scavenging capacity of two compounds 7 and 9 can be explained by the role of OH groups at carbons C-3 and C-4. Antioxidative actions of these two potential agents are followed HAT (H atom transfer) mechanism by OH bond disruption in gas, but SPLET (sequential proton loss electron transfer) mechanism in solvents water and methanol. Compared to 4-OH group, 3-OH group showed better bond disruption enthalpies and better kinetic energies since it reacted with HOO • and DPPH radicals. Sterols 2–3 and flavonoid 11 induced the IC 50 values of 
ISSN:1381-1991
1573-501X
DOI:10.1007/s11030-021-10206-6