The first total synthesis of apigenin 7-O-β-D-cellobiosyl-4′-O-β-D-glucopyranoside isolated from Salvia uliginosa

Abstract

The first total synthesis of apigenin 7-O-β-D-cellobioside (5) and apigenin 7-O-β-D-cellobiosyl-4′-O-β-D-glucopyranoside (8), which were isolated from petals of Salvia patens and Salvia uliginosa, were achieved in four and six steps and 76% and 57%, respectively, overall yield, from naringenin (1). The total synthesis contained two-glycosylation, acetylation, oxidation, selective deacetylation and deprotection steps. Although this route contained six steps, the targeted compounds were obtained with higher yields and easier purifications than other synthetic methods.

Keywords:

• flavonoid glycoside
• apigenin 7-O-β-D-cellobioside
• apigenin 7-O-β-D-cellobiosyl-4′-O-β-D-glucopyranoside
• total synthesis

Acknowledgements

We gratefully acknowledge The Scientific and Technological Research Council of Turkey (TUBITAK) for the financial support of this research granted 105T251.