Dracontomelon dao (Blanco) Merr. et Rolfe of the family Anacardiaceae, locally known as dao is an indigenous Philippine tree which is also widely distributed through out the South and Southeast Asia. 1 The dao bark is used against dysentery. The mature fruits and kernel of the seeds are edible, while the flowers and young leaves are eaten as vegetables. The wood of dao is employed in light construction, timber and firewood. 2 The EtOAc extract of the leaves of D. dao was observed to exhibit strong antibacterial activity with an IC 50 of 98.5 µg/mL. 3 The crude methanolic extracts of the leaves, stem and root barks of D. dao exhibited a very good level of broad spectrum antibacterial activity, while the leaf extract exhibited antifungal activity. 4 The essential oil was extracted from the skins of stem of D. dao by steam distillation. GCMS analysis identified 13 compounds with the following major components: nhexadecanoic acid (46.13%), octadeca noic acid (15.44%), (E)9octadecenoic acid (13.73%), and (Z,Z)9,12octadecadienoic acid (7.79%). 5 We earlier reported the isolation of anacardic acid, βsitosteryl3βglucopyranoside6'Ofatty acid esters, βsitosterol, phytol, phytyl fatty acid esters, βsitosteryl fatty acid esters, chlorophyll a, squalene, longchain fatty alcohols, and longchain hydrocarbons from the leaves of D. dao. 6 We report herein the isolation ofcardol (1), βsitosteryl3βglucopyranoside6, Ofatty acid esters (2), βsitosteryl fatty acid esters (3), and a mixture Chemical Constituents of Dracontomelon Dao (Blanco) Merr. et Rolfe ABSTRACT Introduction: The leaves, twigs and flowers of Dracontomelon dao (Blanco) Merr. et Rolfe, an indigenous Philippine tree were investigated for their chemical constituents. Methods: The compounds were isolated by silica gel chromatography and their structures were identified by NMR spectroscopy. Results: Chemical investigation of D. dao led to the isolation of cardol (1), β-sitosteryl-3β-glucopyranoside-6, O-fatty acid esters (2), β-sitosteryl fatty acid esters (3), and a mixture of β-sitosterol (4a) and stigmasterol (4b) from the petiole; 1, a mixture of 4a and 4b, anacardic acid (5), triacylglycerols (6), monoacylglycerol (7), long-chain fatty acid esters (8), and linoleic acid (9) from the twigs; and a mixture of 4a and 4b, 5, 6, 8, long-chain fatty alcohols (10), and long-chain hydrocatbons (11) from the flowers of D. dao.The structures of 1 and 5 were elucidated by extensive 1D and 2D NMR spectroscopy, while those of 2-4 and 6-11 were identified by NMR spectroscopy. Conclusion: This is the first report on the isolation of 1, 4b and 6-9 from D. dao.
Ergosterol peroxide (1) and ergosterol (2) were commonly isolated as the major compounds of Philippine mushrooms. Sterols 1 and 2 from the dichloromethane extract of Geastrum triplex and Termitomyces clypeatus, respectively, were evaluated for their cytotoxic activities against four human cancer cell lines, viz., breast cancer (MCF-7), colon cancer (HT-29), leukemia (THP-1), and small lung cell carcinoma (H69PR), and a human normal cell line, human dermal fibroblast-neonatal (HDFn), using the PrestoBlue® cell viability assay. Compounds 1 and 2 exhibited the strongest activities against HT-29 with IC50 values of 1.79 and 2.98 μg/mL, respectively, while Zeocin gave an IC50 of 4.89 μg/mL. These compounds also exhibited strong antiproliferative effects against MCF-7 with IC50 values of 4.13 for 1 and 4.20 μg/mL for compound 2, comparable to Zeocin with IC50 = 3.68 μg/mL. Only moderate cytotoxicity resulted when compounds 1 and 2 were tested against H69PR with IC50 values of 7.78 and 6.83 μg/mL, respectively, while Zeocin exhibited an IC50 of 9.81 μg/mL. Furthermore, compounds 1 and 2 showed no effects against THP-1 (IC50 > 100 μg/mL), while Zeocin showed an IC50 of 4.73 μg/mL. Although compounds 1 and 2 have been reported to exhibit different bioactivities in previous studies, the cancer cell lines tested and/or the polarities of the solvents for extraction varied. Therefore, comparisons of the cytotoxic activities of compounds 1 and 2 with earlier studies could not be made extensively.
Chemical investigation of the dichloromethane extracts of Cordia dichotoma G. Forst led to the isolation of βsitosteryl-3β-glucopyranoside-6'-O-palmitate (1), nervonyl 4-hydroxy-trans-cinnamate ester (2), β-sitosterol (3), and chlorophyll a (4) from the leaves; and 4 and 1,2-dilinoleoyl-3-linolenoylglycerol ( 5) from the twigs. The structures of 1-5 were identified by comparison of their NMR data with those reported in the literature. The fatty acids in 1, 2 and 5 were deduced from ESI-MS data.
Aim: To investigate the chemical constituents of the dichloromethane extract of the fruiting bodies of the mushroom Lentinus tigrinus. Materials and Methods: The chemical constituents of L. tigrinus were isolated by silica gel chromatography, while the chemical structures of the isolated compounds were identified by NMR spectroscopy. Results: The dichloromethane extract of the fruiting bodies of L. tigrinus afforded cerevisterol (1), and a mixture of stellasterol (2) and ergosterol (3) in about 4:5 ratio. Conclusion: To the best of our knowledge, this is the first report on the isolation of 1-3 from the fruiting bodies of L. tigrinus.
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