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

• Published in: Tetrahedron: asymmetry Vol. 11; no. 1; pp. 1 - 8
• Main Authors: Asano, Naoki, Kuroi, Hiroyo, Ikeda, Kyoko, Kizu, Haruhisa, Kameda, Yukihiko, Kato, Atsushi, Adachi, Isao, Watson, Alison A, Nash, Robert J, Fleet, George W.J
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.01.2000; Elsevier
• Subjects: Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Chemistry, Physical; Physical Sciences; Science & Technology; GLYCOPROTEIN
• ISSN: 0957-4166; 1362-511X
• DOI: 10.1016/S0957-4166(99)00508-X

Four new polyhydroxypyrrolizidines, hyacinthacines A 1, A 2, A 3 and B 3, have been isolated from the bulbs of Muscari armeniacum (Hyacinthaceae) in addition to the known hyacinthacine C 1, which was isolated from Hyacinthoides non-scripta (Hyacinthaceae). The structures of hyacinthacines A 1, A 2, A 3 and B 3 were identified on the basis of extensive NMR studies as (1 S,2 R,3 R,7a R)-1,2-dihydroxy-3-hydroxymethylpyrrolizidine, (1 R,2 R,3 R,7a R)-1,2-dihydroxy-3-hydroxymethylpyrrolizidine, (1 R,2 R,3R,5 R,7a R)-1,2-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine and (1 S,2 R,3 R,5 R,7 R,7a R)-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.