NEW ANTHRANILIC AND METHYLSULFONYLPROPENOIC ACID-AMIDES FROM THAI GLYCOSMIS SPECIES

Five new methylsulfonylpropenamides were isolated from different Glyco smis species collected in Thailand. Four of these derivatives contain 4-geranyloxy-3-hydroxy-substituted phenethylamine moieties. Sakerine ( 1) has a simple geranyloxy side chain; sakerone (2), sakerol (3), and dihydroisosakerol (4) are characterized by different states of oxidati on in the geranyloxy residue. Methylgerambullal (5) contains a 4-geran yloxy-substituted phenethylamine unit with a terminal formyl group. Tw o additional amides, doisuthine (6) and methoxydoisutkine (7), exhibit the structures of N-methylanthranilic acid amides with phenethylamine and p-methoxyphenethylamine as amine components. All structures were elucidated by IR, UV, H-1-, C-13-, 2D-NMR spectroscopy, mass spectrome try, and CD spectroscopy.