New Ester Alkaloids from Lupins (Genus Lupinus)

Abstract

Esters of 13-hydroxylupanine and 4-hydroxylupanine with acetic, propionic, butyric, isobutyric, valeric, isovaleric, tiglic, benzoic, and trans-cinnamic acid have been synthesized and characterized by capillary gas-liquid chromatography and mass spectrometry (EI-MS, CI-MS). In Lupinus polyphyllus, L. albus, L. angustifolius, and L. mutabilis we could identify new ester alkaloids (e.g. 13-propyloxylupanine, 13-butyryloxylupanine, 13-isobutyryloxylupanine, and 4-tigloyloxylupanine) besides the known esters, i.e. 13-acetoxylupanine, 13-isovaleroyloxylupanine, 13-angeloyloxylupanine, 13-tigloyloxylupanine, 13-benzoyloxylupanine, 13-cis-cinnamoyloxylupanine nine, and 13-trans-cinnamoyloxylupanine.