PHYTOCHEMICAL AND CYTOTOXIC INVESTIGATIONS OF THE HEARTWOOD OF CAESALPINIA SAPPAN LINN
Keywords:Caesalpinia sappan, Nil, Brazilin, Cytotoxicity, Leukemia cells
Â Â Objective: The purpose of this study was to identify the chemical constituents in the dichloromethane extract by gas chromatographyâ€“mass spectrometry (GCâ€“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 GCâ€“MS and column chromatography. Cytotoxic effects on leukemia cells of the isolated compounds were examined using MTT assay.
Results: The GCâ€“MS analysis of dichloromethane extract from C. sappan revealed the presence of 14 compounds. Linoleic acid and Î²-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 Î²-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 (IC50) values of 13.30 Â± 0.49 and 12.24 Â± 1.08 Î¼g/ml, respectively.
Conclusion: Many groups of phytochemical compounds in the dichloromethane extract of C. sappan were detected by GCâ€“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.
Sireeratawong S, Piyabhan P, Singhalak T, Wongkrajang Y, Temsiririrkkul R, Punsrirat J, et al. Toxicity evaluation of sappan wood extract in rats. J Med Assoc Thai 2010;93 Suppl 7:S50-7.
Nirmal NP, Rajput MS, Prasad RG, Ahmad M. Brazilin from Caesalpinia sappan heartwood and its pharmacological activities: A review. Asian Pac J Trop Med 2015;8:421-30.
Chen YP, Liu L, Zhou YH, Wen J, Jiang Y, Tu PF. Chemical constituents from Sappan lignum. J Chin Pharm Sci 2008;17:82-6.
Pawar CR, Landge AD, Surana SJ. Phytochemical and pharmacological aspects of Caesalpinia sappan. J Pharm Res 2008;1:131-8.
Zhao MB, Li J, Shi SP, Cai CQ, Tu PF, Tang L, et al. Two new phenolic compounds from the heartwood of Caesalpinia sappan L. Molecules 2014;19:1-8.
Namikoshi M, Nakata H, Saitoh T. Homoisoflavonoids from Caesalpinia sappan. Phytochemistry 1987;26:1831-3.
Namikoshi M, Nakata H, Yamada H, Nakai M, Saitoh T. Homoisoflavonoids and Related compounds II. 1). Isolation and absolute configurations of 3, 4-dihydroxylated homoisoflavan and brazilins from Caesalpinia sappan L. Chem Pharm Bull 1987;35:2761-73.
Nguyen HX, Nguyen MT, Nguyen TA, Nguyen NY, Phan DA, Thi PH, et al. Cleistanthane diterpenes from the seed of Caesalpinia sappan and their ant austerity activity against PANC-1 human pancreatic cancer cell line. Fitoterapia 2013;91:148-53.
Jeong IY, Jin CH, Park YD, Lee HJ, Choi DS, Byun MW. Anti-inflammatory activity of an ethanol extract of Caesalpinia sappan L. in LPS-induced RAW 264.7 cells. J Food Sci Nutr 2008;13:253-8.
Sasaki Y, Hosokawa T, Nagai M, Nagumo S. In vitro study for inhibition of NO production about constituents of Sappan lignum. Biol Pharm Bull 2007;30:193-6.
Safitria R, Tarigana P, Freislebenb HJ, Rumampukc RJ, Murakamid A. Antioxidant activity in vitro of two aromatic compounds from Caesalpinia sappan L. BioFactors 2003;19:71-7.
Kadchumsang S, Sirisa-ard P, Sookkhee S, Chansakaow S. Antibacterial and Antioxidant activities of lanna medicinal plants used in mahoog formula. Int J Pharm Pharm Sci 2015;7:366-70.
Hung TM, Hai NX, Nhan NT, Quang TT, Quan TL, Cuong TD, et al. Cytotoxicity of new phenolic compounds from vietnamese Caesalpinia sappan. Biosci Biotechnol Biochem 2013;77:2378-82.
Laksmiani NP, Susidarti RA, Meiyanto E. Brazilein increases the sensitivity of doxorubicin on MCF-7 resistant doxorubicin (MCF-7/
DOX) cells through inhibition of HER-2 activation. Int J Pharm Pharm Sci 2015;7:525-8.
Nugraheni K, Saputri FC. The effect of secang extract (Caesalpinia sappan Linn) on the weight and histology appearance of white male ratsâ€™ heart induced by isoproterenol. Int J Appl Pharm 2017;9:59-61.
Sermakkani M, Thangapandian V. GC-MS analysis of Cassia italica leaf methanol extract. Asian J Pharm Clin Res 2012;5:90-4.
Bennani H, Drissi A, Giton F, Kheuang L, Fiet J, Adlouni A. Antiproliferative effect of polyphenols and sterols of virgin Argan oil on human prostate cancer cell lines. Cancer Detect Prev 2007;31:64-9.
Klippel KF, Hiltl DM, Schipp B. A multicentric, placebo-controlled, double-blind clinical trial of beta-sitosterol (phytosterol) for the treatment of benign prostatic hyperplasia. German BPH-Phyto study group. Br J Urol 1997;80:427-32.
Wilt TJ, MacDonald R, Ishani A. Beta-sitosterol for the treatment of benign prostatic hyperplasia: A systematic review. BJU Int 1999;83:976-83.
Fotie J, Bohle DS, Leimanis ML, Georges E, Rukunga G, Nkengfack AE. Lupeol long-chain fatty acid esters with antimalarial activity from Holarrhena floribunda. J Nat Prod 2006;69:62-7.
De-Eknamkul W, Potduang B. Biosynthesis of Î²-sitosterol and stigmasterol in Croton sublyratus proceeds via a mixed origin of isoprene units. Phytochemistry 2003;62:389-98.
Forgo P, Kover KE. Gradient enhanced selective experiments in the 1H NMR chemical shift assignment of the skeleton and side-chain resonances of stigmasterol, a phytosterol derivative. Steroids 2004;69:43-50.
Hung TM, Dang NH, Dat NT. Methanol extract from vietnamese Caesalpinia sappan induces apoptosis in HeLa cells. Biol Res 2014;47:1-5.
Lee DY, Lee MK, Kim GS, Noh HJ, Lee MH. Brazilin inhibits growth and induces apoptosis in human glioblastoma cells. Molecules 2013;18:2449-57.
How to Cite
The publication is licensed under CC By and is open access. Copyright is with author and allowed to retain publishing rights without restrictions.