Rutaceous constituents—13

Chemistry of Acronycine VI. Proton NMR Spectral Assignments of Acronycine and Derivatives and the Formation of Isonoracronycine

“…Consequently, we were interested in the comparison between the two nuclei and also in simple methods to distinguish the two skeleta since this had been such a problem in the past. Some assignments of the 1H-NMR spectra of acronycine (5,21), noracronycine (6,10,22), des-N-methylacronycine (17), isonoracronycine (21) and several other simple acronycine derivatives (14,21,(23)(24)(25)(26) have been reported previously. However, this report constitutes the first complete set of assignments for any unsubstituted acronycine derivatives.…”

“…In general terms, the chemistry of acronycine (1) has not been well investigated, although dihydro-and dihydronor- (3) and nitro- (8) derivatives have been reported. Subsequently, a number of syntheses of acronycine and related derivatives have appeared (9)(10)(11)(12)(13)(14)(15)(16)(17).…”

N-Phenyl-2-nitrobenzamide, an acridone alkaloid precursor

“…The isolation of both of these compounds from the same plants, Teclea verdoorniana and Oricio suareolens, has led to the proposal that aminobenzophenones are probable intermediates in the biosynthesis of acridone alkaloids (Adams et al, 1981). This step is of great importance in biological systems as acridone alkaloids have reported success as anticancer drugs (Adams et al, 1981). The conclusion that aminobenzophenones are likely intermediates in the synthesis of acridone alkaloids is further supported by the biomimetic synthesis of acronycine from a benzophenone precursor.…”

“…These compounds have very similar structures and the former is thought to be a precursor in the biosynthesis of the latter. The isolation of both of these compounds from the same plants, Teclea verdoorniana and Oricio suareolens, has led to the proposal that aminobenzophenones are probable intermediates in the biosynthesis of acridone alkaloids (Adams et al, 1981). This step is of great importance in biological systems as acridone alkaloids have reported success as anticancer drugs (Adams et al, 1981).…”

Chemistry of Acronycine IV. Minor Constituents of Acronine and the Phytochemistry of the Genus Acronychia

“…sample confirmed the identity. The alkaloid has previously been isolated from G. pentapbylla (33) and 1. paniculata (34) and synthesized en route to acronycine (1) (39,40).…”