Constituents from the Roots of Semiaquilegia adoxoides

In present literature search, some cyano-containing compounds, which are very rare in plants, from the traditional anticancer herb Tiankuizi were reported. To find more cyano-containing compounds in the important plant Semiaquilegia adoxoides (DC) Makino (Chinese name Tiankuizi), the isolation of the chemical constituents was investigated for advancing the research. Two new compounds, a new alkaloid, 1,2,3,4-tetrahydro-6-hydroxy-1- [(3,4-dihydroxyphenyl)methyl]-7-methoxy-2,2-dimethyl-isoquinolinium, named Semiaquilegine A (1), and a new ester, 3-(4′-hydroxyphenyl)-2-propenoic acid (4′′-carboxyl)-phenyl ester (2), and four cyano-containing compounds, (Z)-6α-(β-D-glucosyloxy)-4α,5α-dihydroxy-2-cyclohexene-Δ¹,α-acetonitrile (3), (Z)-6α-(β-D-glucosyloxy)-4α-hy-droxy-2-cyclohexene-Δ¹,α-acetonitrile (4), lithospermoside (5), ehretioside B (6), as well as eleven known compounds, were isolated from the roots of Semiaquilegia adoxoides. The structures of new compounds 1 and 2 were elucidated mainly by 1D/2D-NMR techniques. Very unusual cyano-containing compounds 3 and 4 were first isolated from Ranunculaceae family. Hitherto, there were six cyano-containing compounds found in the herb.