Erythrophleum

All the erythrophleum alkaloids examined in detail so far are of the same type, viz., acyl esters of either monomethylaminoethanol, e.g., erythrophleine and coumingidine or dimethylaminoethanol, such as cassaine or cassaidine. The acyl substituents are complex, yield 1 7 8-trimethylphenanthrene on selenium dehydrogenation, and contain at least one hydroxyl group, which may be acylated by an aliphatic acid, e.g., coumingine forms three components on hydrolysis. 

The known diterpenoid norerythrophlamide has been isolated from the stem bark of Erythrophleum teysmannii Craib var. puberulum Craib... 

The 2-methylaminoethyl esters of the Erythrophleum alkaloids readily rearrange to the amides and this has in the past caused some confusion. The conditions for the isolation of the esters from Erythrophleum chlorostachys have now been carefully defined.40 3/3-Acetoxynorerythrosuamine (39) is a new highly cytotoxic alkaloid41 from this source. 

Cassaine Cassia carnaval, Erythrophleum Na+, K+-ATPase [anaesthetic,... 

Menispermaceae), Argemone, Chelidonium, Corydalis (Papaveraceae), Coptis, Thalictrum (Ranunculacae), Evodia, Toddalia, fanthoxylum (Rutaceae) spp. Erythrophleum guineense,... 

A useful review of the diterpene alkaloids has appeared.Partition chromatography of the Erythrophleum alkaloids from the bark of Erythrophleum guineense has led to the isolation of 8-dehydrocassaic acid. This may arise by the dehydration of a 6a-hydroxy-alkaloid (6a-hydroxycassaine), since erythro-phleguine (6a-hydroxycassamine) gives 8-dehydrocassamic acid on hydrolysis. 

Errazurizia (dunebroom) Erythrina (erythrina) Erythrophleum (sasswood) Eysenhardtia (kidneywood)... 

Erythrophleum guineense G. Don Blrem Whitlow Infected wounds cardiotoxic poison to kill noxious animals (B) Powder dilution of mashed bark... 

The Africans have long used the calabar bean as an ordeal poison. A person who was suspected of being guilty of a crime was forced to eat the crushed beans. If he survived, he was considered innocent. The bark of Erythrophleum pfuineense has also been used for this purpose... 

From another leguminous plant now classified in the Caesalpiniaceae, Erythrophleum chlorostachys, several alkaloids typified by norerythrostachamine (94) were isolated and their structures elucidated they occur as ethanolamine esters of diterpene acids, but readily rearrange to the corresponding amides [ 111J. These alkaloids are highly toxic and are responsible for cattle poisoning in the Darwin area. 

Cassanes.— -Caesalpin (41), from Caesalpinia pulcherrima, possesses the cassane skeleton, and is thus related to the bitter principles isolated from the seeds of Caesalpinia bonducella. Cassminic acid is a minor constituent of the bark of Erythrophleum guineense. Spectroscopic measurements and an interrelationship with cassane-16,19-dioic acid have established " it as 6-oxo-7-hydroxycass-13-ene-16,19-dioic acid. N.m.r. measurements and bromination-dehydrobromina-tion studies are in accord with the axial 14a-configuration now accepted for the cassamic acid diterpenes. 

The leaves of this plant grown at Mareeba, North Queensland, yielded j3-dimethylaminoethyl cinnamate, N-2-hydroxyethyl-N-cinna-mamide, iV-2-hydroxyethyl-N-methyl- ra s-p-hydroxycinnamamide, and 2-hydroxyethylcinnamamide. The structures were confirmed by syntheses. Though some of these may be artifacts, generated during the isolation, the same products were not found in leaves of the same plant grown at Darwin, N.T., or at Cooktown, North Queensland. The leaves of the latter two sources yielded the alkaloid esters of terpenoid acids as in other Erythrophleum species (93). 

Most of the members of the genus Erythrophleum contain alkaloids (233), and many have proved toxic to animals. In particular, ironwood (E. chlorostachys) has caused poisoning in horses, cattle, sheep, and goats in tropical Australia, a few ounces of the leaves being sufficient to cause death (234). 

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