Balfourodendron riedelianum

Alkaloids Isolated from Lunasia amara and Balfourodendron riedelianum ... 

O-Methylbalfourodinium salt (11) is the major quaternary alkaloid of young Brazilian trees of the Balfourodendron riedelianum Engl, species... 

Corral and Orazi (46) isolated a number of new tertiary bases from Argentinian Balfourodendron riedelianum. The phenolic alkaloids ribaline and ribalinidine were not found in the tertiary base fraction but were precipitated as reineckates with the quaternary alkaloids, presumably because of their zwitterion character and their low solubility in chloroform. 

Balfourodine was reported to rearrange with acetic anhydride and pyridine into (+)-isobalfourodine acetate (122), which was hydrolyzed to (-t-)-isobalfourodine (overall 48% racemization), but it is now known that these products are derived from (+)-balfourodine rather than from the levorotatory enantiomer. Because (+)-balfourodine occurs in Balfourodendron riedelianum, and there is no indication that (—)-balfourodine was available from another source, it appears probable that (—)-balfourodine is a misprint for (+)-balfourodine in the earlier paper. Alternative mechanisms involving inversion at the chiral center were proposed for the rearrangement of balfourodine effected by acetic anhydride... 

Alkaloids of this type have been described previously, and during the last ten years new sources of known alkaloids have been recorded. Thus, the simplest member of the group 309, previously obtained only from Balfourodendron riedelianum, has now been isolated from Haplophyllum foliosum (164). Graveoline (rutamine) (310), a characteristic alkaloid of... 

Balfourodendron riedelianum [42], Ruta graveolens [42], R. graveolens spp. hortensis [44]... 

Rapoport H, Holden K G 1959 Isolation of alkaloids from Balfourodendron riedelianum. J Am Chem Soc 81 3738-3743... 

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