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

Abstract

Dihydromyricetin (DMY) was efficiently extracted from Ampelopsis grossedentata and modified by esterification to obtain two derivatives, which were named as benzoylated derivative (BZ-DMY) and acetylated derivative (AC-DMY). The physicochemical characterizations of BZ-DMY and AC-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 indicated that esterification of DMY were successfully modified by benzoyl and acetyl. The substitute positions 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 (BZ-DMY and AC-DMY) as potential anti-hepatocellular carcinoma therapeutic drugs.