Guatteria alkaloids

Dielsiquinone (134) is the only Guatteria alkaloid known to possess the 1-azaanthracene ring system (22). This skeleton was found for the first time in the parent compound cleistopholine (154), isolated successively from the An-nonaceae Cleistopholis patens (77) and Meiogyne virgata (78), and later also from Annona cherimolia (79) and A. hayesii (80). The latter species also contains the related annopholine (155). Annona ambotay (81) is the only known... 

Montenegro, H., Gutidrrez, M., Romero, L. L, Ortega-Barrfa, E., Capson, T. L. and Rios, L. C. 2003. Aporhine alkaloids from Guatteria spp. with Leishmanicidal activity. Planta Medica, 69 677-679. 

Guatteria megalophylla Diels (Annonaceae) afforded (/ ,/ )- , 0-dimethylcur-ine (144), C38H42N206, mp 133-136°C (EtOAc-cyclohexane), identified by UV, NMR, MS, and ORD, and by comparison with a sample synthesized by CH2N2 methylation of (/ ,/ )-l2 -0-methyIcurme (145, Section II,C,64), also isolated from this plant (82). (/ ,/ )-< ,0,-Dimethylcurine had been prepared by methylation of (/ ,/ )-curine (75) (83), but was not previously reported in nature however, (5,S)-0,0-dimethylcurine is a known alkaloid of Cissampelos pareira (84). 

III. Alkaloids from Chemically Investigated Guatteria Species. 3... 

Previous volumes of this treatise have addressed the occurrence, chemistry, and pharmacology of the major structural types of alkaloids found in Guatteria. Nevertheless, of the 20 bisbenzylisoquinolines described to date as Guatteria constituents, only 2 are discussed in the chapter by Cava et al. (1), and only... 

The emergence of the azafluorenone alkaloids as a sizable group and the discovery of the azaanthracenes and azahomoaporphines, all represented in Guat-teria, are very new developments. This chapter reviews these novel substances as completely as possible, discusses a small number of structurally unusual though not unprecedented compounds, and also updates the older contributions on the mainline isoquinoline alkaloids insofar as the genus Guatteria is concerned. 

A new review of the bisbenzylisoquinoline alkaloids, entitled The bisbenzylisoquinoline alkaloids," which covers some of the Guatteria constituents described here, appeared in print after this chapter had been submitted for publication K. T. Buck, in The Alkaloids (A. Brossi, ed.), Vol. 30, pp. 1-222. Academic Press, San Diego, California, 1987. 

Chemically Investigated Guatteria Species and Their Contained Alkaloids... 

Fig. 1. Structural types of alkaloids isolated from Guatteria species.

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