Objective: The purpose of this study was to identify the chemical constituents in the dichloromethane extract by gas chromatography-mass spectrometry (GC-MS) analysis and evaluate the cytotoxic effects on leukemia cells of isolated compounds from Caesalpinia sappan Linn.Methods: Dichloromethane extract obtained from the heartwood of C. sappan was investigated by GC-MS and column chromatography. Cytotoxic effects on leukemia cells of the isolated compounds were examined using MTT assay. Results:The GC-MS analysis of dichloromethane extract from C. sappan revealed the presence of 14 compounds. Linoleic acid and β-sitosterol were found to be the major compounds presenting in 14% and 13%, respectively. The separation of the dichloromethane extract led to the isolation of brazilin (1) as a major compound, together with lupeol (2), and a mixture of β-sitosterol (3), and stigmasterol (4). Their structures were elucidated based on spectroscopic methods. Brazilin (1) showed a cytotoxic effect on human acute myeloid leukemia cell (KG1) and human acute myeloid leukemia stem cell (KG1a) with inhibitory concentration at 50% growth (IC 50 ) values of 13.30 ± 0.49 and 12.24 ± 1.08 µg/ml, respectively. Conclusion:Many groups of phytochemical compounds in the dichloromethane extract of C. sappan were detected by GC-MS analysis. Some of them have been reported to possess various biological activities. Moreover, brazilin (1) isolated compound from C. sappan shows cytotoxicity on leukemia cells, which could be a potential anticancer property.
The Lycopodiaceae family is the main source of Lycopodium alkaloids (LAs). The phytochemical constituents of alkaloid extract from seven species of Thai club mosses: Phlegmariurus carinatus, P. squarrosus, P. nummularifolius, P. phlegmaria, Lycopodiella cernua, Lycopodium clavatum and L. complanatum, were reviewed and classified into four major groups consisting of: lycopodine, lycodine, fawcettimine and phlegmarine (or miscellaneous group). The phytochemical relationships between the genera, Phlegmariurus (4 species), Lycopodium (2 species) and Lycopodiella (1 species) were investigated and reviewed based on their isolated Lycopodium alkaloids. The structures of 38 Lycopodium alkaloids are presented and some LAs are marked as key representatives for classification of the genera. The content of huperzine A in the club moss species was evaluated for biological activities. Some isolated LAs were potent acetylcholinesterase (AChE) inhibitors. This review focuses on the structural classification of the LAs isolated from Thai club mosses and their biological activities, especially acetylcholinesterase inhibitory activity.
A facile and direct synthetic entry to the carbon skeleton of Clausena alkaloids, the benzo[d]azocin-4-one, is reported featuring the ring expansion of 1-phenyldihydroisoquinoline derivatives initially triggered by oxazolone under environmentally benign conditions in a one-pot procedure. Functionalization of the eight-membered lactam framework provided a set of Clausena alkaloid derivatives. Some derivatives show a promising inhibition toward acetylcholinesterase and a better selectivity index than the previously used Alzheimer’s disease (AD) drug, tacrine, and the currently used AD drug, galantamine.
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