Antimycobacterial triterpenes from Melia volkensii.

Abstract

In a bioassay-guided search for antimycobacterial compounds from higher plants, we have chemically investigated methanolic extracts of seeds of Melia volkensii. Chromatographic fractions provided two new euphane (20R)-type triterpenoids. The structures of the new compounds, 12beta-hydroxykulactone (1) and 6beta-hydroxykulactone (2), were elucidated by 1D and 2D NMR (13C, 1H, 1H-1H COSY, HMQC, HMBC, and NOESY spectra) and FABMS studies and shown to be hydroxyl derivatives of kulactone (3). Also isolated was the known kulonate (4). In a radiorespirometric bioassay against Mycobacterium tuberculosis, compounds 1, 2, and 4 exhibited minimum inhibitory concentrations of 16, 4, and 16 microg/mL, respectively.