Anti-tuberculosis compounds from Mallotus philippinensis.

Bioassay-directed fractionation of the organic extract of Mallotus philippinensis gave five compounds (1-5), the most active of which against Mycobacterium tuberculosis was a new compound, 8-cinnamoyl-5,7-dihydroxy-2,2-dimethyl-6-geranylchromene (1) for which the name mallotophilippen F is suggested. Compound (2), 8-cinnamoyl-2,2-dimethyl-7-hydroxy-5-methoxychromene, was isolated from a natural source for the first time, while the remaining three compounds, rottlerin (3), isoallorottlerin=isorottlerin (4) and the so-called "red compound," 8-cinnamoyl-5,7-dihydroxy-2,2,6-trimethylchromene (5), had been isolated previously from this plant. All compounds were identified by analysis of their spectra including 2D-NMR, which was used to correct the literature NMR spectral assignments of compounds 2-4. The C-13 NMR of 5 is reported for the first time.