Annonaceae oxoaporphines

New oxoaporphines are oxolaureline (lauterine) (55), obtained from Magnolia soulangeana Soul-Bod (Magnoliaceae),63 from Laurelia novae-zelandiae A. Cunn. (Monimiaceae),64 and from Guatteria elata R. E. Fries (Annonaceae),65 and oxo-puterine (56), which is present, with (55), in G. elata.65... 

A variety of aporphine, proaporphine, oxoaporphine, and 4,5-dioxo-aporphine alkaloids are known from plants of the families Annonaceae, Lauraceae, and Menispermaceae. 

Azafluorenone and diazafluoranthene alkaloids, which are biogenetically related to oxoaporphines, usually co-occur in plants of the family Annona-ceae. Cyathocaline (53), C14H11NO4, mp 222-224°, is a new azafluorenone alkaloid isolated from the stem bark of Cyathocalyx zeylanica Champ, ex Hook. f. and Thoms., a species of the Annonaceae endemic to Sri Lanka (50). Its structure was elucidated using spectroscopic techniques and by... 

Oxoaporphines.—Recent sources for known oxoaporphines are liriodenine, Melodorum punctulatum (Annonaceae) 0-methylatheroline and cassamedine, Annona purpurea L. (Annonaceae) and dicentrinone, Ocotea macropoda (Lauraceae). New oxoaporphines are oxopurpureine (122), isolated from Annona purpurea L., and hernandonine (123) found in Hernandia ovigera and H. jamaicensis (Hernandiaceae). ... 

Splendidine (37), a new oxoaporphine, has been obtained from Abuta rufescens Aublet ( = A. splendida) (Menispermaceae). Following its structural elucidation, its total synthesis was achieved via a Reissert-Pschorr sequence The known phenolic oxoaporphine subsessiline, found in a Guatteria species (Annonaceae), has been established to possess structure (39) instead of the... 

A new violet oxoaporphine alkaloid, liriodendronine (49), has been isolated from the discolored sapwood of Liriodendron tulipifera. The compound exists primarily as a quinone methide in neutral medium, as a dianion in base, and as an isoquinolinium ion in weak acid/ Another new oxoaporphine is oxopukateine (50), present in Duguetia eximia (Annonaceae) together with the known O-methylmoschatoline (1,2,3-trimethoxyoxoaporphine) and oxoputerine (1,2-methylenedioxy-ll-methoxyoxoaporphine)/ ... 

The simplest derivatives of the tetrahydrobenzylisoquinoline alkaloids are the aporphine alkaloids (Fig. 32.12). Aporphine alkaloids (about 650) are widespread and occur in almost the same families as benzylisoquinoline alkaloids (Guinaudeau and Bruneton, 1993 Kametani and Honda, 1985). Several subgroups of aporphine alkaloids are known [noraporphines, dehydroaporphines (34), oxoaporphines (35), dimeric apor-phines, and phenanthrenes (36)] (Fig. 32.13) (Cave et al., 1987). The aporphine alkaloids present in members of the Annonaceae and in the genus Thalictrum (Ranunculaceae) have been reviewed (Cave et al., 1987 Schiff, 1987). 

From the benzylisoquinolines are derived all the types of isoquinoline alkaloids found in the Annonaceae (Fig. 3) berberines, aporphines, oxoaporphines, phenanthrenes, cularines, morphinanedienones, isoquinolones, dimethylaminoethyl-benziles and bisbenzylisoquinolines. 

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