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

Benjamin J. Ayers; Jacqueline Hollinshead; Alexander W. Saville; Shinpei Nakagawa; Isao Adachi; Atsushi Kato; Ken Izumori; Barbara Bartholomew; George W.J. Fleet; Robert J. Nash

doi:10.1016/j.phytochem.2014.01.012

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

Benjamin J. Ayers^*, Jacqueline Hollinshead, Alexander W. Saville, Shinpei Nakagawa, Isao Adachi, Atsushi Kato, Ken Izumori, Barbara Bartholomew, George W.J. Fleet, Robert J. Nash

^*Corresponding author for this work

Hospital Pharmacy

Research output: Contribution to journal › Article › peer-review

29 Scopus citations

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.

Original language	English
Pages (from-to)	126-131
Number of pages	6
Journal	Phytochemistry
Volume	100
DOIs	https://doi.org/10.1016/j.phytochem.2014.01.012
State	Published - 2014/04

Keywords

Grossulariaceae
Itea virginica
Iteamine
d-Psicose
α-N-acetylgalactosaminidase

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Plant Science
Horticulture

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10.1016/j.phytochem.2014.01.012

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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.",

keywords = "Grossulariaceae, Itea virginica, Iteamine, d-Psicose, α-N-acetylgalactosaminidase",

author = "Ayers, {Benjamin J.} and Jacqueline Hollinshead and Saville, {Alexander W.} and Shinpei Nakagawa and Isao Adachi and Atsushi Kato and Ken Izumori and Barbara Bartholomew and Fleet, {George W.J.} and Nash, {Robert J.}",

note = "Funding Information: This work was supported by the Newton Abraham Research Fund (B.J.A.), the Leverhulme Trust (G.W.J.F.) and a Grant-in-Aid for Scientific Research (C) (No: 23590127 ) (A.K.) from the Japanese Society for the Promotion of Science (JSPS) . ",

year = "2014",

month = apr,

doi = "10.1016/j.phytochem.2014.01.012",

language = "英語",

volume = "100",

pages = "126--131",

journal = "Phytochemistry",

issn = "0031-9422",

publisher = "Elsevier Ltd.",

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TY - JOUR

T1 - Iteamine, the first alkaloid isolated from Itea virginica L. inflorescence

AU - Ayers, Benjamin J.

AU - Hollinshead, Jacqueline

AU - Saville, Alexander W.

AU - Nakagawa, Shinpei

AU - Adachi, Isao

AU - Kato, Atsushi

AU - Izumori, Ken

AU - Bartholomew, Barbara

AU - Fleet, George W.J.

AU - Nash, Robert J.

N1 - Funding Information: This work was supported by the Newton Abraham Research Fund (B.J.A.), the Leverhulme Trust (G.W.J.F.) and a Grant-in-Aid for Scientific Research (C) (No: 23590127 ) (A.K.) from the Japanese Society for the Promotion of Science (JSPS) .

PY - 2014/4

Y1 - 2014/4

N2 - 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.

AB - 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.

KW - Grossulariaceae

KW - Itea virginica

KW - Iteamine

KW - d-Psicose

KW - α-N-acetylgalactosaminidase

UR - http://www.scopus.com/inward/record.url?scp=84897623617&partnerID=8YFLogxK

U2 - 10.1016/j.phytochem.2014.01.012

DO - 10.1016/j.phytochem.2014.01.012

M3 - 学術論文

C2 - 24534106

AN - SCOPUS:84897623617

SN - 0031-9422

VL - 100

SP - 126

EP - 131

JO - Phytochemistry

JF - Phytochemistry

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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