Dihydromyricetin from Ampelopsis grossedentata and its derivatives: Structural characterization and anti-hepatocellular carcinoma activity

Dihydromyricetin (DMY) was efficiently extracted from Ampelopsis grossedentata and modified by esteri-fication to obtain two derivatives, which were named as benzoylated derivative (B-Z-DMY) and acetylated derivative (A(C)-DMY). The physicochemical characterizations of B-Z-DMY and A(C)-DMY were investigated by TLC, SEM, HPLC, FT-IR, NMR and MS analysis. Simultaneously, the anti-hepatocellular carcinoma activity was determined by cell experiment to investigate their structure-activity relationship. The results indi-cated that esterification of DMY were successfully modified by benzoyl and acetyl. The substitute posi-tions were C-3, C-5, C-7, C-3' , C-4' and C-5 ' respectively inferred from NMR analysis. In the experiment of anti-hepatocellular carcinoma activity, two novel derivatives showed better anti-tumor ability than DMY. Therefore, it can be concluded that esterified DMY could significantly induce HepG2 cells apoptosis and improve the anti-tumor activity of DMY. In summary, this research could not only enhance the development and utilization of Ampelopsis grossedentata, but also develop these two derivatives (B-Z-DMY and A(C)-DMY) as potential anti-hepatocellular carcinoma therapeutic drugs.(c) 2022 Elsevier B.V. All rights reserved.