ABSTRACT
A phytochemical investigation of the liana of Artabotrys thomsonii led to the isolation of a new oxoberberine alkaloid, 2,10-dihydroxy-3,9-dimethoxy-8-oxo-protoberberine (7), along with six known compounds. Their chemical structures were elucidated by 1 D and 2 D NMR spectroscopic methods and HRESI-MSn data analysis. Compounds 4 and 7 were selected for further in vitro investigations. In accordance with expectations from their chemical structures, compounds 7 and 4 showed a clear antioxidant activity in a cell-free assay, with compound 7 being 7-fold more active than 4. Cytotoxicity, cytostatic and genotoxic effects only occurred at high micromolar concentrations of 50 µM or more. Compound 7 was slightly less effective than compound 4. A low micromolar concentration of 10 µM did not cause any damaging cellular effects but showed potential for a protection against the micronucleus-inducing effect of reactive oxygen species hydrogen peroxide, although not to a significant extent.
Subject(s)
Alkaloids , Annonaceae , Antineoplastic Agents , Alkaloids/pharmacology , Annonaceae/chemistry , DNA Damage , Molecular StructureABSTRACT
Two new 5-methylcoumarin glycosides named diosfeboside A (1) and B (2) and five known compounds namely kaempferol 3-O-α-L-rhamnopyranosyl-(1 â 2)-ß-D-glucopyranoside (3), ursolic acid (4), betulinic acid (5), stigmasterol (6) and stigmasterol 3-O-ß-D-glucopyranoside (7) were isolated from the leaves of Diospyros crassiflora (Hiern). Their structures were established through interpretation of 1 and 2D NMR, mass spectra analysis and comparison with reported data. In vitro cytotoxic activity of the new compounds against human carcinoma cell lines (HL-60, Bel-7402, BGC-823, and KB) was evaluated and no cytotoxicity was observed for each of them.
