Pentasubstituted Aporphine Alkaloids From Phoebe molicella

Journal of Natural Products
1983.0

Abstract

The known aporphine alkaloids norpurpureine, purpureine, and preocoteine (previously incompletely characterized), as well as the new alkaloid norpreocoteine, have been isolated from Phoebe molicella (Lauraceae). The 13C-nmr spectra of three of these pentasubstituted aporphines is presented for the first time, as is a summary of previous work in the genus Phoebe. The genus Phoebe of the family Lauraceae is of wide tropical occurrence but has been little studied chemically. The leaf alkaloids of Phoebe clmsii (New Guinea) were found to be isocorydine (1), 10-hydroxy-1,2-methylenedioxyaporphine (2), and N-methyllindcarpine (3), while the bark consisted largely of laurolitsine (4) (1). Nine alkaloids were found in Phoebefomzosana (Taiwan): the wood yielding roemerine (5) and laurolitsine (plus two unknowns), and the bark containing laurolitsine, ushinsunine (6), and liriodenine (7), as well as three additional unknowns (2). An investigation of bark from Phoebe porfiria (Argentina) gave "quaternary and tertiary alkaloides," but only ocoteine (8) was identified (3). These three studies represent the only previous investigations we have been able to find. 1: Rl=R2=R4=OMe; R,=OH; R,=H. 2: R,, R2=OCH,0; R4=OH; R,=R,=H. 3: Rl=R,=OH; R,=R,=OMe; R,=H. 4: Rl=R4=OMe; R,=R,=OH; R,=H. 5: R,, R,=OCH,O; R,=R,=OH; R,=H. A screening program (4) revealed the presence of alkaloids in Phoebe pittieri (Costa Rica). Screening by the Centro de Investigacion en Productos Naturales (CIPRONA) group in Costa Rica identified additional alkaloid-containing species. The present work reports on one new and three known, but previously incompletely characterized, aporphines from Phoebe molicella.

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