Phytochemical and Cytotoxic Investigations of the Heartwood of Caesalpinia Sappan Linn

Abstract

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.

Antioxidant activity and phenolic content of ginger (Zingiber officinale Roscoe) combination with cinnamon (Cinnamomum burmanii) and Sappan wood (Caesalpinia sappan) as an anti-diabetic

“…Brazilin has the potential to develop into a drug and also act as a nutraceutical [11]. Brazilin also as anti-cancer [12].…”

The cytotoxicity of brazilin and derivatives might be due to an inhibition of the c-Src-kinase

“…Furthermore, a neuroprotective effect of 1 has been established in a human neuroblastoma model 13 . There are also some reports on the cytotoxic activity of brazilein but less for brazilin 11,[14][15][16][17][18][19][20][21] .…”

“…This is in contradiction, however, with those publications reporting minor toxic or cytotoxic effects for 1. Therefore, we were interested in evaluating the cytotoxic potential of 1 18,21 . To also determine a possible influence of lipophilicity on cytotoxic behavior, different acyl derivatives of 1 (log Po/w = 1.51) were prepared, such as acetates 2 and 3 (log Po/w = 2.52 and 3.00), a tris-chloro-acetate 4 (log Po/w = 3.45) and a tris-chlorobutyrate 5 (log Po/w = 5.11).…”