The bioactivity of prenylated stilbenoids and their structure-activity relationship

Dietary prenylated stilbenoids present in many food resources, and have good bioactivities. However, their structure-activity relationships are rarely reported. In this work, eighteen C-and O-prenylated stilbenoids were chemically semisynthesized using one-step approach. They all could inhibit sugar digestive enzymes, including alpha-glucosidase and alpha-amylase. 4-Geranyl piceatannol from jackfruit showed the strongest activity by suppressing dipeptidyl peptidase-IV (DPP-IV) activity. The enzyme inhibition kinetics were measured and the inhibition mechanism was revealed. Evaluation of antioxidant activity highlighted that the introduction of prenyl with increasing prenyl chain length can significantly increase the antioxidant activity of stilbenoids. Our results suggested that prenylated stilbenoids could be used as functional food additives to decrease postprandial blood sugar levels by inhibiting sugar digestive enzymes and DPP-IV. Prenylated stilbenoids present remarkable DPP-IV inhibitory activity, providing more useful information for the prevention of type 2 diabetes.

Automated summary

This study chemically semi-synthesized 18 prenylated stilbenoids and investigated their bioactivities. The results showed that these compounds could inhibit sugar digestive enzymes and DPP-IV activity, and the antioxidant activity increased with longer prenyl chains. Therefore, prenylated stilbenoids can be used as functional food additives to decrease postprandial blood sugar levels and have implications for the prevention of type 2 diabetes.