Bioassay-guided fractionation of the EtOH extract of licorice (Glycyrrhiza glabra roots), using a GAL-4-PPAR-γ chimera assay method, resulted in the isolation of 39 phenolics, including 10 new compounds (1–10). The structures of the new compounds were determined by analysis of their spectroscopic data. Among the isolated compounds, 5′-formylglabridin (5), (2R,3R)-3,4′,7-trihydroxy-3′-prenylflavane (7), echinatin, (3R)-2′,3′,7-trihydroxy-4′-methoxyisoflavan, kanzonol X, kanzonol W, shinpterocarpin, licoflavanone A, glabrol, shinflavanone, gancaonin L, and glabrone all exhibited significant PPAR-γ ligand-binding activity. The activity of these compounds at a sample concentration of 10 μg/mL was three times more potent than that of 0.5 μM troglitazone.Bioassay-guided fractionation of the EtOH extract of licorice (Glycyrrhiza glabra roots), using a GAL-4-PPAR-γ chimera assay method, resulted in the isolation of 39 phenolics, including 10 new compounds (1–10).

•Karataviosides G–K (1–5) were isolated the bulbs of Allium karataviense.•Compounds 1–5 are new bisdesmosidic steroidal glycosides.•The structures were elucidated by NMR analysis and the results of hydrolysis.•Compound 1 is furostanol glycoside with a triglucosyl unit at C-26 of the aglycone.•Compounds 1–5 were evaluated for their cytotoxic activities against tumor cell lines.We have analyzed the steroidal glycosides in Allium karataviense bulbs, and isolated five new bisdesmosidic steroidal glycosides: karataviosides G−K (1–5). The structures were elucidated by extensive spectroscopic analysis, including 2D NMR and enzymatic and hydrolytic cleavage. Karatavioside G (1) is an entirely novel furostanol glycoside, which has an O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl unit at C-26 of the aglycone. Although a variety of cholestanol glycosides have been isolated, mainly from Liliaceae and Agavaceae, karataviosides J and K (4 and 5) are also notable because they are the most polar cholestanol bisdesmosides discovered, in which a lycotetraose is attached to C-3 of the aglycone, and a glucose or O-glucosyl-(1 → 3)-glucose is attached at C-16. The isolated glycosides were also evaluated for their cytotoxic activities against cultured tumor cell lines.Download full-size image

Five new pregnane tetraglycosides, amurensiosides A–E (1–5), two new pregnane hexaglycosides, amurensiosides F (6) and I (9), two new 18-norpregnane hexaglycosides, amurensiosides G (7) and H (8), and two new pregnane octaglycosides, amurensiosides J (10) and K (11), were isolated from the MeOH extract of the roots of Adonis amurensis. The structures of the new compounds were determined on the basis of extensive spectroscopic analysis, including two-dimensional (2D) NMR data, and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activity against HSC-2 human oral squamous cell carcinoma cells.