Bioassay-guided isolation of α-Glucosidase inhibitory constituents from Hypericum sampsonii.
10.1016/S1875-5364(23)60472-8
- Author:
Linlan TAO
1
,
2
,
3
;
Shuangyu XU
1
,
2
,
3
;
Zizhen ZHANG
1
,
2
,
3
;
Yanan LI
1
,
2
,
3
;
Jue YANG
1
,
2
,
3
;
Wei GU
1
,
2
,
3
;
Ping YI
1
,
2
,
4
;
Xiaojiang HAO
1
,
2
,
5
,
6
;
Chunmao YUAN
1
,
2
,
7
Author Information
1. State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, China
2. School of Pharmaceutical Sciences, Guizhou Medical University, Guiyang 550025, China
3. Natural Products Research Center of Guizhou Province, Guiyang 550014, China.
4. Natural Products Research Center of Guizhou Province, Guiyang 550014, China. Electronic address: yiping2100@aliyun.com.
5. Natural Products Research Center of Guizhou Province, Guiyang 550014, China
6. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China. Electronic address: haoxj@mail.kib.ac.cn.
7. Natural Products Research Center of Guizhou Province, Guiyang 550014, China. Electronic address: yuanchunmao01@126.com.
- Publication Type:Journal Article
- Keywords:
Chemical constituents;
Hypericum sampsonii;
Molecular docking;
Structure elucidation;
α-Glucosidase
- MeSH:
Molecular Structure;
Hypericum/chemistry*;
alpha-Glucosidases;
Magnetic Resonance Spectroscopy;
Glycoside Hydrolase Inhibitors/pharmacology*
- From:
Chinese Journal of Natural Medicines (English Ed.)
2023;21(6):443-453
- CountryChina
- Language:English
-
Abstract:
This study employed the α-glucosidase inhibitory activity model as an anti-diabetic assay and implemented a bioactivity-guided isolation strategy to identify novel natural compounds with potential therapeutic properties. Hypericum sampsoniiwas investigated, leading to the isolation of two highly modified seco-polycyclic polyprenylated acylphloroglucinols (PPAPs) (1 and 2), eight phenolic derivatives (3-10), and four terpene derivatives (11-14). The structures of compounds 1 and 2, featuring an unprecedented octahydro-2H-chromen-2-one ring system, were fully characterized using extensive spectroscopic data and quantum chemistry calculations. Six compounds (1, 5-7, 9, and 14) exhibited potential inhibitory effects against α-glucosidase, with IC50 values ranging from 0.050 ± 0.0016 to 366.70 ± 11.08 μg·mL-1. Notably, compound 5 (0.050 ± 0.0016 μg·mL-1) was identified as the most potential α-glucosidase inhibitor, with an inhibitory effect about 6900 times stronger than the positive control, acarbose (IC50 = 346.63 ± 15.65 μg·mL-1). A docking study was conducted to predict molecular interactions between two compounds (1 and 5) and α-glucosidase, and the hypothetical biosynthetic pathways of the two unprecedented seco-PPAPs were proposed.
