New Sugar-Mimic Alkaloids from the Pods of Angylocalyx pynaertii

Kayo Yasuda, Haruhisa Kizu, Toru Yamashita, Yukihiko Kameda, Atsushi Kato, Robert J. Nash, George W. J. Fleet, Russell J. Molyneux, Naoki Asano

Research output: Contribution to journalArticlepeer-review

80 Citations (Scopus)

Abstract

Chromatographic separation of the pod extract of Angylocalyx pynaertii resulted in the isolation of 13 sugar-mimic alkaloids (1−13). The structures of the new alkaloids were elucidated by spectroscopic methods as the 6-O-β-d-glucoside (10) and N-hydroxyethyl derivative (11) of 1,4-dideoxy-1,4-imino-d-arabinitol (DAB) (1), 1,6-dideoxynojirimycin (12), and 1,3,4-trideoxynojirimycin (13). 2,5-Imino-1,2,5-trideoxy-l-glucitol (7), 2,5-dideoxy-2,5-imino-d-fucitol (8), and β-homofuconojirimycin (9), isolated from the pods as well as the bark, were very specific inhibitors of α-l-fucosidase with no significant inhibitory activity toward other glycosidases. In this work, 1,4-dideoxy-1,4-imino-d-ribitol (6) was found to be a better inhibitor of lysosomal β-mannosidase than 2,5-imino-1,2,5-trideoxy-d-mannitol (2). N-Hydroxyethyl-1-deoxynojirimycin (miglitol), which is commercially available for the treatment of diabetes, retained its inhibitory potential toward rat intestinal maltase and sucrase, whereas 11 and the synthetic N-hydroxyethyl derivative of 2,5-dideoxy-2,5-imino-d-mannitol markedly lowered or abolished their inhibition toward all enzymes tested.
Original languageEnglish
Pages (from-to)198-202
Number of pages5
JournalJournal of Natural Products
Volume65
Issue number2
DOIs
Publication statusPublished - 06 Feb 2002

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