An α-glucoside of 1,4-dideoxy-1,4-imino-d-lyxitol with an eleven carbon side chain

Atsushi Kato; Jackie Hollinshead; Yukiko Yamashita; Shinpei Nakagawa; Yuriko Koike; Isao Adachi; Chu Yi Yu; George W.J. Fleet; Robert J. Nash

doi:10.1016/j.phytol.2010.08.006

An α-glucoside of 1,4-dideoxy-1,4-imino-d-lyxitol with an eleven carbon side chain

Atsushi Kato^*, Jackie Hollinshead, Yukiko Yamashita, Shinpei Nakagawa, Yuriko Koike, Isao Adachi, Chu Yi Yu, George W.J. Fleet, Robert J. Nash

^*Corresponding author for this work

Hospital Pharmacy

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

15 Scopus citations

Abstract

The distribution of pyrrolidine-type iminosugars with a long-side chain appears to be restricted to the relatively unrelated plant families Moraceae, Campanulaceae, and Hyacinthaceae. In a search for glycosidase inhibitors in these plant families, we isolated the 1,4-dideoxy-1,4-imino-d-lyxitol (DIL) glucoside bearing the 1,2,11-trihydroxyundec-4-ene side chain at the C-1α position from the roots of Adenophora triphylla. This iminosugar was a powerful and selective inhibitor of coffee bean α-galactosidase, with an IC ₅₀ value of 8 μM.

Original language	English
Pages (from-to)	230-233
Number of pages	4
Journal	Phytochemistry Letters
Volume	3
Issue number	4
DOIs	https://doi.org/10.1016/j.phytol.2010.08.006
State	Published - 2010/12/17

Keywords

1,4-Dideoxy-1,4-imino-d-lyxitol
Glycosidase inhibitor
Iminosugars
Pyrrolidine alkaloids
α-Galactosidase inhibitor

ASJC Scopus subject areas

Biotechnology
Biochemistry
Agronomy and Crop Science
Plant Science

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10.1016/j.phytol.2010.08.006

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@article{f6554f91b83c4f0bb433e794258e04ac,

title = "An α-glucoside of 1,4-dideoxy-1,4-imino-d-lyxitol with an eleven carbon side chain",

abstract = "The distribution of pyrrolidine-type iminosugars with a long-side chain appears to be restricted to the relatively unrelated plant families Moraceae, Campanulaceae, and Hyacinthaceae. In a search for glycosidase inhibitors in these plant families, we isolated the 1,4-dideoxy-1,4-imino-d-lyxitol (DIL) glucoside bearing the 1,2,11-trihydroxyundec-4-ene side chain at the C-1α position from the roots of Adenophora triphylla. This iminosugar was a powerful and selective inhibitor of coffee bean α-galactosidase, with an IC 50 value of 8 μM.",

keywords = "1,4-Dideoxy-1,4-imino-d-lyxitol, Glycosidase inhibitor, Iminosugars, Pyrrolidine alkaloids, α-Galactosidase inhibitor",

author = "Atsushi Kato and Jackie Hollinshead and Yukiko Yamashita and Shinpei Nakagawa and Yuriko Koike and Isao Adachi and Yu, {Chu Yi} and Fleet, {George W.J.} and Nash, {Robert J.}",

year = "2010",

month = dec,

day = "17",

doi = "10.1016/j.phytol.2010.08.006",

language = "英語",

volume = "3",

pages = "230--233",

journal = "Phytochemistry Letters",

issn = "1874-3900",

publisher = "Elsevier Ltd.",

number = "4",

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TY - JOUR

T1 - An α-glucoside of 1,4-dideoxy-1,4-imino-d-lyxitol with an eleven carbon side chain

AU - Kato, Atsushi

AU - Hollinshead, Jackie

AU - Yamashita, Yukiko

AU - Nakagawa, Shinpei

AU - Koike, Yuriko

AU - Adachi, Isao

AU - Yu, Chu Yi

AU - Fleet, George W.J.

AU - Nash, Robert J.

PY - 2010/12/17

Y1 - 2010/12/17

N2 - The distribution of pyrrolidine-type iminosugars with a long-side chain appears to be restricted to the relatively unrelated plant families Moraceae, Campanulaceae, and Hyacinthaceae. In a search for glycosidase inhibitors in these plant families, we isolated the 1,4-dideoxy-1,4-imino-d-lyxitol (DIL) glucoside bearing the 1,2,11-trihydroxyundec-4-ene side chain at the C-1α position from the roots of Adenophora triphylla. This iminosugar was a powerful and selective inhibitor of coffee bean α-galactosidase, with an IC 50 value of 8 μM.

AB - The distribution of pyrrolidine-type iminosugars with a long-side chain appears to be restricted to the relatively unrelated plant families Moraceae, Campanulaceae, and Hyacinthaceae. In a search for glycosidase inhibitors in these plant families, we isolated the 1,4-dideoxy-1,4-imino-d-lyxitol (DIL) glucoside bearing the 1,2,11-trihydroxyundec-4-ene side chain at the C-1α position from the roots of Adenophora triphylla. This iminosugar was a powerful and selective inhibitor of coffee bean α-galactosidase, with an IC 50 value of 8 μM.

KW - 1,4-Dideoxy-1,4-imino-d-lyxitol

KW - Glycosidase inhibitor

KW - Iminosugars

KW - Pyrrolidine alkaloids

KW - α-Galactosidase inhibitor

UR - http://www.scopus.com/inward/record.url?scp=78649495379&partnerID=8YFLogxK

U2 - 10.1016/j.phytol.2010.08.006

DO - 10.1016/j.phytol.2010.08.006

M3 - 学術論文

AN - SCOPUS:78649495379

SN - 1874-3900

VL - 3

SP - 230

EP - 233

JO - Phytochemistry Letters

JF - Phytochemistry Letters

IS - 4

ER -

An α-glucoside of 1,4-dideoxy-1,4-imino-d-lyxitol with an eleven carbon side chain

Abstract

Keywords

ASJC Scopus subject areas

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