Melosmine and Melosmidine 7,7-Dimethyltetradehydroaporphine Alkaloids From Guatteria melosma

Journal of Natural Products
1982.0

Abstract

Fractionation and chromatography of an ethanol extract of the stembark of Guatteria melosma Diels (Annonaceae) afforded melosmine (2) and melosmidine (3), two members of a new class of aporphine alkaloids (7,7-dimethyltetradehydroaporphines). A consideration of the spectral data of melosmine (2) and its O,O-dimethyl-(5), tetrahydro-(6), O,O-dimethyltetrahydro-(7), N-methyltetrahydro-(8), N-methyl-O,O-dimethyltetrahydro-(9) and O,O-diacetyl-(10) derivatives suggested the structure to be 2 (2,3-dimethoxy-7,7-dimethyl-7H-dibenzo [de,g] quinolin-1,9-diol). This was confirmed by x-ray crystallographic analysis. A consideration of the spectral data of melosmidine (3) and its O-methyl-(5), tetrahydro-(11), N-methyltetrahydro-(12) and O-acetyl-(13) derivatives indicated that melosmidine was 3 (1,2,3-trimethoxy-7,7-dimethyl-7H-dibenzo [de,g] quinolin-9-ol). O-Methylmelosmidine (5) is identical to O,O-dimethylmelosmine (5). In addition, isoboldine (4) and two uncharacterized alkaloids, GMA 1 and GMA 2, were isolated. © 1982, American Chemical Society. All rights reserved.

Knowledge Graph

Similar Paper