Necines of alkaloids in Heliotropium species from Mexico and the U.S.A.

The qualitative and quantitative compositions of necines in plants of 20 Heliotropium species collected in Mexico and the U.S.A. and one species from Spain are reported. Trachelanthamidine, supinidine and retronecine were found in all species after hydrolysis of their alkaloids; lindelofidine was detected in most species, whereas heliotridine only in four. Trachelanthamidine, lindelofidine, and supinidine were dominant in four, two and one species, respectively; retronecine was dominant in 15 species, whereas heliotridine only in one. The dominant necine in H. ternatum was either retronecine or lindelofidine depending on the collection locality. Qualitative as well as quantitative differences depending on the collection locality were found in H. curassavicum. Plants from Oaxaca, Mexico, contained lindelofidine and a pyrrolizidine-diol as major necines, trachelanthamidine as minor, and traces of retronecine. Plants originating from two other localities contained trachelanthamidine (dominant), retronecine, and supinidine. The necine patterns found in the examined species differ significantly from those previously reported for 21 species mainly collected in Asia, the Middle East and Australia.