Saundersiosides C-H, rearranged cholestane glycosides from the bulbs of Ornithogalum saundersiae and their cytostatic activity on HL-60 cells.
Six novel rearranged cholestane glycosides with a six-membered hemiacetal ring system, designated as saundersiosides C-H, were isolated from the bulbs of Ornithogalum saundersiae. Their structures were determined on the basis of spectroscopic analysis and the result of hydrolysis. The conformation of the six-membered hemiacetal ring of the rearranged cholestanes was shown to be almost a boat-form by molecular mechanics and molecular dynamics calculation studies. Among the isolated compounds, saundersioside E, F, G and H with an aromatic acid ester group at the glycoside moiety were found to be highly cytostatic to human leukemia HL-60 cells, showing IC50 values of 0.021, 0.019, 0.063 and 0.052 microM, respectively, which are as potent as those of the clinically applied anticancer agents, etoposide and methotrexate.
Kuroda
M
M
School of Pharmacy, Tokyo University of Pharmacy and Life Science, Japan.
Mimaki
Y
Y
Sashida
Y
Y
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002776:Cholestanes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry; D018922:HL-60 Cells; D006801:Humans; D019668:Liliaceae / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D013055:Spectrophotometry, Infrared
D000972:Antineoplastic Agents, Phytogenic; D002776:Cholestanes; D006027:Glycosides