New polyhydroxylated pyrrolizidine alkaloids from Muscari armeniacum: Structural determination and biological activity

Naoki Asano; Hiroyo Kuroi; Kyoko Ikeda; Haruhisa Kizu; Yukihiko Kameda; Atsushi Kato; Isao Adachi; Alison A. Watson; Robert J. Nash; George W.J. Fleet

doi:10.1016/S0957-4166(99)00508-X

New polyhydroxylated pyrrolizidine alkaloids from Muscari armeniacum: Structural determination and biological activity

Naoki Asano^*, Hiroyo Kuroi, Kyoko Ikeda, Haruhisa Kizu, Yukihiko Kameda, Atsushi Kato, Isao Adachi, Alison A. Watson, Robert J. Nash, George W.J. Fleet

^*Corresponding author for this work

Hospital Pharmacy

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

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Abstract

Four new polyhydroxypyrrolizidines, hyacinthacines A₁, A₂, A₃ and B₃, have been isolated from the bulbs of Muscari armeniacum (Hyacinthaceae) in addition to the known hyacinthacine C₁, which was isolated from Hyacinthoides non-scripta (Hyacinthaceae). The structures of hyacinthacines A₁, A₂, A₃ and B₃ were identified on the basis of extensive NMR studies as (1S,2R,3R,7aR)-1,2-dihydroxy-3-hydroxymethylpyrrolizidine, (1R,2R,3R,7aR)-1,2-dihydroxy-3-hydroxymethylpyrrolizidine, (1R,2R,3R,5R,7aR)-1,2-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine and (1S,2R,3R,5R,7R,7aR)-3-hydroxymethyl-5-methyl-1,2,7-trihydroxypyrrolizidine, respectively, or the corresponding enantiomers. The inhibitory activities of these new hyacinthacines against a variety of glycosidases are described. Copyright (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	1-8
Number of pages	8
Journal	Tetrahedron Asymmetry
Volume	11
Issue number	1
DOIs	https://doi.org/10.1016/S0957-4166(99)00508-X
State	Published - 2000/01/28

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "New polyhydroxylated pyrrolizidine alkaloids from Muscari armeniacum: Structural determination and biological activity",

abstract = "Four new polyhydroxypyrrolizidines, hyacinthacines A1, A2, A3 and B3, have been isolated from the bulbs of Muscari armeniacum (Hyacinthaceae) in addition to the known hyacinthacine C1, which was isolated from Hyacinthoides non-scripta (Hyacinthaceae). The structures of hyacinthacines A1, A2, A3 and B3 were identified on the basis of extensive NMR studies as (1S,2R,3R,7aR)-1,2-dihydroxy-3-hydroxymethylpyrrolizidine, (1R,2R,3R,7aR)-1,2-dihydroxy-3-hydroxymethylpyrrolizidine, (1R,2R,3R,5R,7aR)-1,2-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine and (1S,2R,3R,5R,7R,7aR)-3-hydroxymethyl-5-methyl-1,2,7-trihydroxypyrrolizidine, respectively, or the corresponding enantiomers. The inhibitory activities of these new hyacinthacines against a variety of glycosidases are described. Copyright (C) 2000 Elsevier Science Ltd.",

author = "Naoki Asano and Hiroyo Kuroi and Kyoko Ikeda and Haruhisa Kizu and Yukihiko Kameda and Atsushi Kato and Isao Adachi and Watson, {Alison A.} and Nash, {Robert J.} and Fleet, {George W.J.}",

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T1 - New polyhydroxylated pyrrolizidine alkaloids from Muscari armeniacum

T2 - Structural determination and biological activity

AU - Asano, Naoki

AU - Kuroi, Hiroyo

AU - Ikeda, Kyoko

AU - Kizu, Haruhisa

AU - Kameda, Yukihiko

AU - Kato, Atsushi

AU - Adachi, Isao

AU - Watson, Alison A.

AU - Nash, Robert J.

AU - Fleet, George W.J.

PY - 2000/1/28

Y1 - 2000/1/28

N2 - Four new polyhydroxypyrrolizidines, hyacinthacines A1, A2, A3 and B3, have been isolated from the bulbs of Muscari armeniacum (Hyacinthaceae) in addition to the known hyacinthacine C1, which was isolated from Hyacinthoides non-scripta (Hyacinthaceae). The structures of hyacinthacines A1, A2, A3 and B3 were identified on the basis of extensive NMR studies as (1S,2R,3R,7aR)-1,2-dihydroxy-3-hydroxymethylpyrrolizidine, (1R,2R,3R,7aR)-1,2-dihydroxy-3-hydroxymethylpyrrolizidine, (1R,2R,3R,5R,7aR)-1,2-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine and (1S,2R,3R,5R,7R,7aR)-3-hydroxymethyl-5-methyl-1,2,7-trihydroxypyrrolizidine, respectively, or the corresponding enantiomers. The inhibitory activities of these new hyacinthacines against a variety of glycosidases are described. Copyright (C) 2000 Elsevier Science Ltd.

AB - Four new polyhydroxypyrrolizidines, hyacinthacines A1, A2, A3 and B3, have been isolated from the bulbs of Muscari armeniacum (Hyacinthaceae) in addition to the known hyacinthacine C1, which was isolated from Hyacinthoides non-scripta (Hyacinthaceae). The structures of hyacinthacines A1, A2, A3 and B3 were identified on the basis of extensive NMR studies as (1S,2R,3R,7aR)-1,2-dihydroxy-3-hydroxymethylpyrrolizidine, (1R,2R,3R,7aR)-1,2-dihydroxy-3-hydroxymethylpyrrolizidine, (1R,2R,3R,5R,7aR)-1,2-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine and (1S,2R,3R,5R,7R,7aR)-3-hydroxymethyl-5-methyl-1,2,7-trihydroxypyrrolizidine, respectively, or the corresponding enantiomers. The inhibitory activities of these new hyacinthacines against a variety of glycosidases are described. Copyright (C) 2000 Elsevier Science Ltd.

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IS - 1

ER -

New polyhydroxylated pyrrolizidine alkaloids from Muscari armeniacum: Structural determination and biological activity

Abstract

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