palustrine

Description

This alkaloid from Equisetum palustra was first obtained by Glet and his colleagues and examined further by Karrer and Eugster. It is dextrorotatory with [α]¹⁹_D + 15.8° (CHC13) and forms crystalline salts, e.g. the dihydrochloride hydrate, m.p. 188-190°C (dec.); [α]¹⁸_D + 8.4° (H20) which yields an acid solu_x0002_tion in H20; diperchlorate, m.p. 270 C (dec.); dipicrate, m.p. lS0-lS0.SoC; platinichloride as orange crystals, m.p. 221-3°C (dec.); dipicrolonate, m.p. 154°C and the reineckate, m.p. 174°C. The alkaloid contains two active hydrogens but no methoxyl groups and on reduction yields the dihydro derivative. The latter base, on Hofmann degradation followed by hydrogenation and hydrolysis yields dihydropalustramic acid, 6-(fj-hydroxypropyl)-piperid-2-yl-acetic acid. From these observations, a modified structure for the alkaloid has been suggested although the complete structure is not yet known with certainty. The plant has sometimes given rise to cases of poisoning in cattle which appear to be due to the alkaloid

Definition

ChEBI: Palustrine is a lactam and an azamacrocycle.

References

Glet, Gutschmidt, Glet., Zeit. Physiol. Chem., 244, 229 (1936)
Karrer, Eugster., Helv. Chim. Acta., 31, 1062 (1948)
Eugster.,Griot, Karrer., ibid, 36, 1387 (1953)
Structure:
Mayer et al., Helv. Chim. Acta, 51,661 (1968)

Raw materials

Preparation Products