Flavonoids from the cultured cells of Glycyrrhiza echinata

Article abstract of DOI:10.1016/S0031-9422(00)82219-0

Constituents of the cultured cells of Glycyrrhiza echinata have been investigated. Echinatin (4,4′-dihydroxy-2-methoxychalcone), a biosynthetically unique retrochalcone, and licodione (1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1,3-propanedione), a dibezoylmethane derivative, which is the possible precursor of echinatin, were obtained. The structures were determined by spectroscopic methods and syntheses. ¹H NMR of licodione revealed new features in chemical shifts of protons of diketonic and keto-enolic forms. 7,4′-Dihydroxyflavone, two of its prenyl derivatives and formononetin were also isolated. A discussion on retrochalcone biosynthesis is presented.