title: Iteamine, the first alkaloid isolated from Itea virginica L. inflorescence.
abstract: 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.
authors.affiliation: Chemistry Research Laboratory, University of Oxford, Oxford OX1 3TA, UK. Electronic address: benjamin.ayers@chem.ox.ac.uk.
authors.forename: Benjamin J
authors.initials: BJ
authors.lastname: Ayers
authors.affiliation: Phytoquest Limited, IBERS, Plas Gogerddan, Ceredigion, Aberystwyth SY23 3EB, Wales, UK.
authors.forename: Jacqueline
authors.initials: J
authors.lastname: Hollinshead
authors.affiliation: Chemistry Research Laboratory, University of Oxford, Oxford OX1 3TA, UK.
authors.forename: Alexander W
authors.initials: AW
authors.lastname: Saville
authors.affiliation: Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
authors.forename: Shinpei
authors.initials: S
authors.lastname: Nakagawa
authors.affiliation: Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
authors.forename: Isao
authors.initials: I
authors.lastname: Adachi
authors.affiliation: Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kato
authors.affiliation: Rare Sugar Research Center, Kagawa University, 2393 Ikenobe, Miki-cho, Kita-gun, Kagawa 761-07, Japan.
authors.forename: Ken
authors.initials: K
authors.lastname: Izumori
authors.affiliation: Phytoquest Limited, IBERS, Plas Gogerddan, Ceredigion, Aberystwyth SY23 3EB, Wales, UK.
authors.forename: Barbara
authors.initials: B
authors.lastname: Bartholomew
authors.affiliation: Chemistry Research Laboratory, University of Oxford, Oxford OX1 3TA, UK.
authors.forename: George W J
authors.initials: GW
authors.lastname: Fleet
authors.affiliation: Phytoquest Limited, IBERS, Plas Gogerddan, Ceredigion, Aberystwyth SY23 3EB, Wales, UK. Electronic address: rob.nash@phytoquest.co.uk.
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Nash
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000818:Animals; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D005960:Glucosides; D056626:Inflorescence / Q000737:chemistry*; D064028:Tracheophyta / Q000737:chemistry*; D048809:alpha-N-Acetylgalactosaminidase / Q000037:antagonists & inhibitors
chemical_list: D000470:Alkaloids; D004791:Enzyme Inhibitors; D005960:Glucosides; C000592500:iteamine; D048809:alpha-N-Acetylgalactosaminidase
keywords: Grossulariaceae; Itea virginica; Iteamine; d-Psicose; α-N-acetylgalactosaminidase