First total synthesis of (±)-sanggenon F and its osteogenic differentiation promoting activity on human mesenchymal stem cells

Sanggenon F is a flavanone-type natural product with different bioactivities, but its total synthesis has never been reported. In the present study, the first total synthesis of (±)-sanggenon F was accomplished in ten steps and 2.4% overall yield, involving two key reactions of the Aldol condensation and oxa-Michael addition. The promoting activity of (±)-sanggenon F on the osteogenic differentiation of human umbilical cord-derived mesenchymal stem cells (MSC) and human adipose-derived MSC was assessed <i>via</i> alkaline phosphatase staining and alizarin red S staining. Excitingly, (±)-sanggenon F displayed significant osteogenic differentiation promoting effect towards both cell lines and it might be used as a template molecule for the future design and development of adjuvant drugs in MSC therapy.