Bioactive chemical constituents from Chisocheton Penduliflorus and CF. Aglaia Erythrosperma

Abstract

Chemical investigation of the leaves, wood and stem bark of Chisocheton penduliflorus Planch. ex Hiern (family Meliaceae) led to the isolation of three aromadendrane sesquiterpenes, namely 14-hydroxyviridiflorol, (-)-10β,13,14-trihydroxy-allo-aromadendrane and a new derivative, five dammarane triterpenes: dammaradienone, cabraleadiol, eichlerialactone, cabralealactone and cabraleahydroxylactone, a hexanortriterpene, hollongdione, two coumarins, scoparone and scopoletin, a chromone, 5-hydroxy-7-methoxy-2-pentylchromone, along with vanillic acid, ethyl orsellinate and β-sitosterol glucoside. Investigation of the leaves, fruits and seeds of another meliaceous plant, cf. Aglaia erythrosperma C.M. Pannell yielded two dammarane triterpenes, ethyl eichlerianoate and aglinin A, and two coumarins, scoparone and scopoletin. Futhermore, an aglalactone, 5,6-desmethylenedioxy-5-methoxy-aglalactone, and a flavagline, 4΄-demethoxy-3΄,4΄-methylenedioxy-methyl rocaglate, were also isolated. The structure determination of these compounds was accomplished by spectroscopic methods, including UV, IR, MS and NMR, and comparison with previously reported data. Cabraleadiol, cabraleahydroxylactone, cabralealactone, eichlerialactone, 14-hydroxyviridiflorol, (-)-10β,13,14-trihydroxy-allo-aromadendrane, a 3:2 mixture of 14-hydroxyviridiflorol and 14-hydroxyepiviridiflorol, 5,6-desmethylenedioxy-5-methoxy-aglalactone, 4΄-demethoxy-3΄,4΄-methylenedioxy-methyl rocaglate and ethyl eichlerianoate exhibited antituberculosis activity. Cabraleadiol, cabraleahydroxylactone, cabralealactone, eichlerialactone, 5,6-desmethylenedioxy-5-methoxy-aglalactone, 4΄-demethoxy-3΄,4΄-methylenedioxy-methyl rocaglate, ethyl eichlerianoate and aglinin A displayed cytotoxic activity, whereas cabraleahydroxylactone, 5,6-desmethylenedioxy-5-methoxy-aglalactone, 4΄-demethoxy-3΄,4΄-methylenedioxy-methyl rocaglate and aglinin A also showed anti HSV-1 activity. Furthermore, 4΄-demethoxy-3΄,4΄-methylenedioxy-methyl rocaglate exhibited antimalarial activity.