NATURAL PRODUCT RESEARCH AND DEVELOPMENT ›› 2024, Vol. 36 ›› Issue (8): 1307-1319.doi: 10.16333/j.1001-6880.2024.8.004

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Chemical constituents from roots of Adina rubella and their α-glucosidase inhibitory activity

LI Ru1,2,CHEN Xue-lin1,WANG Han-lei1,2,ZHANG Zhen-nan1,2,ZHAO Xia1,ZHANG Ku1,2,ZHANG Yu-mei1*   

  1. 1CAS Key Laboratory of Tropical Plant Resource and Sustainable Use,Xishuangbanna Tropical Botanical Garden,Chinese  Academy of Sciences,Kunming 650223,China;2University of Chinese Academy of Sciences,Beijing 100049,China
  • Online:2024-08-28 Published:2024-08-29

Abstract:

This study aims to investigate the chemical components of Adina rubella and evaluate its α-glucosidase inhibitory activity.The constituents from the ethyl acetate fraction of the root of A. rubella were separated and purified by chromatographic techniques including column chromatography of silica gel,Sephadex LH-20 and HPLC.Their structures were mainly elucidated by NMR and MS spectroscopic techniques.Twenty-five compounds were isolated and purified,and use modern wave spectroscopy methods to identify their structures as quinovic acid (1),quinovic acid 3-O-β-D-glucopyranoside (2),quinovic acid 3-O-β-D-fucopyranoside (3),quinovic acid 3-O-β-D-glucopyranosyl-28-O-β-D-glucopyranosyl ester (4),gongganoside C (5),gongganoside A (6),quinovic acid 3-O-β-D-fucopyranosyl-28-O-β-D-glucopyranosyl ester (7),quinovic acid 3-O-β-D-quinovopyranosyl-28-O-β-D-glucopyranosyl ester (8),oleanolic acid (9),sinapic aldehyde (10),coniferaldehyde (11),3,5-di-O-caffeoylquinic methyl ester (12),3,4-di-O-caffeoylquinic methyl ester (13),methyl 4,5-di-caffeoyl-quinate (14),grandifloroside (15),undulatoside A (16),5,7-dihydroxy-2-methylchromone-7-O-β-D-apiosyl-(1→6)-O-β-D-glucoside (17),loganin (18),loganic acid (19),sitosterol (20),6′-O-acetyl-β-daucosterol (21),daucosterol (22),syringaldehyde (23),3,4,5-trimethoxyphenyl-1-O-β-D-apiofuranosyl-(1′′→6′)-O-β-D-glucopyranoside (24),lucidol (25).Among which compounds 2-8,10-14,16,17,19,21,23-25 were isolated from A. rubella for the first time.The results of α-glucosidase inhibition activities showed that compounds 12 and 13 exhibited significant inhibitory activities against α-glucosidase,with IC50 values of 8.83 ± 0.54,8.36 ± 1.01 μmol/L,respectively.Enzyme kinetic analysis showed that the type of inhibition of α-glucosidase by compounds 12 and 13 was mixed competitive inhibition,followed by molecular docking and molecular dynamics simulation results showed that compounds 12 and 13 have superior binding capacities with α-glucosidase (binding energy:-10.08 and -10.65 kcal/mol).Compounds 12 and 13 showed significant α-glucosidase inhibitory activities,and they might be the material basis for the α-glucosidase inhibitory activity of eathy lacetata extract from the root of A. rubella.

Key words: Adina rubella, chemical constituents, hypoglycemic activity, α-glucosidase, molecular docking

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