Triterpene saponins from Cyclamen hederifolium.
Five triterpene saponins never reported before, hederifoliosides A-E, and four known triterpene saponins were isolated from the tubers of Cyclamen hederifolium. The structures of hederifoliosides A-E were determined as 3β,16α-dihydroxy-13β,28-epoxyolean-30-oic acid 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, 3β,16α-dihydroxy-13β,28-epoxyolean-30-oic acid 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, 3β,16α-dihydroxy-13β,28-epoxyolean-30-al 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-[β-D-glucopyranosyl-(1 → 6)]-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, 30-O-β-D-glucopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-3β,16α,30-trihydroxyolean-12-en-28-al 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, 30-O-β-D-glucopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-3β,16α,28,30-tetrahydroxyolean-12-en 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, by a combination of one- and two-dimensional NMR techniques, and mass spectrometry. The cytotoxic activity of the isolated compounds was evaluated against a small panel of cancer cell lines including Hela, H-446, HT-29, and U937. None of the tested compounds, in a range of concentrations between 1 and 50 μM, caused a significant reduction of the cell number.
Chemistry Department, Faculty of Science, Ege University, 35100 Bornova, Izmir, Turkey.
Hilal
H
Altunkeyik
Derya
D
Gülcemal
Milena
M
Masullo
Ozgen
O
Alankus-Caliskan
Sonia
S
Piacente
Tamer
T
Karayildirim
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D031824:Cyclamen / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D019073:HT29 Cells; D006367:HeLa Cells; D006801:Humans; D015394:Molecular Structure; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014421:Turkey
D000972:Antineoplastic Agents, Phytogenic; D012503:Saponins; D014315:Triterpenes