Heliotropium europaeum

Re-examination of the alkaloids of Heliotropium europaeum has revealed the presence of a new alkaloid, acetyllasiocarpine (17) as a minor component. The alkaloid could not be crystallized, but gave lasiocarpine (18) on partial hydrolysis. Proof that the acetoxy group was attached to C-3 was obtained from the C n.m.r. spectrum, which showed a downfield acylation shift of approximately 12 p.p.m. for C-3 by comparison with the corresponding signal in the spectrum of lasiocarpine (18). Acetyllasiocarpine (17) was regenerated from lasiocarpine (18) by acetylation with acetic anhydride. 

C13H33NO3 Supinine -oxide C15H35NO3 Tomentosine Heliotropium supinum L. (93a, 138) Toumefortia sarmentosa Lam. (139) Heliotropium europaeum L. (91, 92) Tournefortia sarmentosa Lam. (139) Senecio tomentosus (140) 232 14° ... 

The occurrence of pyrrolizidine derivatives in the Lepidoptera is not confined to butterflies, but has also been observed in the tiger moth, where their function may be similar to that established in one species of butterfly. Male tiger moths (fam. Arctiidae) possess scent organs in the form of inflatable coremata which have a pheromone-distributing function. Some of these species are known to use plants containing pyrrolizidine alkaloids, e.g. Heliotropium europaeum and Echium... 

Loss of livestock due to pyrrolizidine alkaloid poisoning is a growing economic problem. The effects of these alkaloids on animals was discussed at a recent symposium (750). An outbreak of chicken poisoning in Australia was caused by food containing seeds of Heliotropium europaeum 220). The toxicity of a range of pyrrolizidine esters on rats has been studied 81). 

Bull, L. B., Culvenor, C. C., Keast, J. C., and Edgar, G. 1956. An Experimental Investigation of the Hepatotoxic and of Other Effects on Sheep of the Consumption of Heliotropium europaeum L. Heliotrope Poisoning of Sheep. Australian Journal of Agricultural Research 7 281-332. 

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