Iteamine, the first alkaloid isolated from Itea virginica L. inflorescence

Iteamine, o-aminobenzyl β-d-glucopyranoside, is the first alkaloid isolated from Itea, the only plant source of the rare sugar d-psicose in development as a zero calorie food. •The discovery of iteamine, the first alkaloid isolated from Itea virginica.•Confirmation of the structure of iteamine by synthesis, and the synthesis of the galacto-epimer.•The galacto-epimer of iteamine showed weak but interesting inhibition of alpha-GalNAcase. Iteamine, o-aminobenzyl β-d-glucopyranoside, is the first alkaloid to be isolated from Itea virginica. Itea is the sole plant source of d-psicose, a rare sugar likely to be a major dietary supplement. The structure of iteamine was established by NMR and confirmed by total synthesis. Iteamine and its galacto-analog (which was not found in Itea plants) showed no strong inhibition of any of the 15 glycosidases tested; unnatural galacto-iteamine was a weak inhibitor of chicken liver α-N-acetylgalactosaminidase.