Isolation from and x-ray crystal structure of alexine, (1r,2r,3r,7s,8s)-3-hydroxymethyl-1,2,7-trihydroxypyrrolizidine [(2r,3r,4r,5s,6s)-2-hydroxymethyl-1-azabicyclo[3.3.0]octan-3,4,6-triol], a unique pyrrolizidine alkaloid
TL;DR: The isolation from Alexa leiopetala and identification by X-ray crystal structure analysis of (1R,2R,3R,4R,5S,6S)-2-hydroxymethyl-1-azabicyclo[3.3.0]octan-3,4,6-triol], a unique pyrrolizidine alkaloid, is described in this paper.
About: This article is published in Tetrahedron Letters.The article was published on 1988-01-01. It has received 117 citations till now. The article focuses on the topics: Pyrrolizidine alkaloid & Hydroxymethyl.
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TL;DR: The structural basis for the specificity of inhibition of alkaloidal sugar mimics and their current and potential application to biomedical problems will be reviewed.
Abstract: Alkaloids mimicking the structures of monosaccharides are now believed to be widespread in plants and microorganisms, and these sugar mimics inhibit glycosidases because of a structural resemblance to the sugar moiety of the natural substrate. Naturally occurring sugar mimics with a nitrogen in the ring are classified into five structural classes: polyhydroxylated piperidines, pyrrolidines, indolizidines, pyrrolizidines and nortropanes. Glycosidases are involved in a wide range of important biological processes, such as intestinal digestion, post-translational processing of glycoproteins and the lysosomal catabolism of glycoconjugates. The realization that alkaloidal sugar mimics might have enormous therapeutic potential in many diseases such as viral infection, cancer and diabetes has led to increasing interest and demand for these compounds. Most of these effects can be shown to result from the direct or indirect inhibition of glycosidases. The glycosphingolipid (GSL) storage diseases are relatively rare hereditary disorders that are severe in nature and frequently fatal. Possible strategies for the treatment of these lysosomal storage diseases include enzyme replacement therapy, gene therapy and substrate deprivation. Recently, quite a new therapy for lysosomal storage diseases has been reported, namely a ‘chemical chaperone therapy’ for Fabry disease. In this report, the structural basis for the specificity of inhibition of alkaloidal sugar mimics and their current and potential application to biomedical problems will be reviewed.
881 citations
TL;DR: Over one hundred polyhydroxylated alkaloids have been isolated from plants and micro-organisms, and only three of the natural products so far have been widely studied for therapeutic potential due largely to the limited commercial availability of the other compounds.
643 citations
Cites background from "Isolation from and x-ray crystal st..."
...…1990) Castanospermine Castanospermum australe (Leguminosae) seeds/leaves/bark (Hohenschutz et al., 1981) Alexa spp. (Leguminosae) seeds/leaves/bark (Nash et al., 1988c) 6-Epicastanospermine Castanospermum australe (Leguminosae) seeds/leaves/bark (Molyneux et al., 1986; Nash et al.,…...
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...Alexine Disaccharidase-type a-glucosidases (trehalase, amyloglucosidase) and b-galactosidase (Nash et al., 1988a, 1990a) 3,7a-Diepialexine Disaccharidase-type a-glucosidases (amyloglucosidase and sucrase) (Nash et al., 1990a) 7a-Epialexine (Australine) Disaccharidase-type a-glucosidases…...
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...5) Alexine Alexa spp. (Leguminosae) seeds/leaves (Nash et al., 1988a) 3,7a-Diepialexine Castanospermum australe (Leguminosae) seeds/leaves (Nash et al., 1988b) 7a-Epialexine (Australine) Castanospermum australe (Leguminosae) seeds/leaves (Molyneux et al., 1988) 1,7a-Diepialexine Alexa spp. and…...
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TL;DR: In this paper, a microreview of recent syntheses of polyhydroxylated piperidines is presented, focusing on recent synthesises of azasugars and their analogs.
202 citations
TL;DR: In this article, the use of isoxazolidine as a versatile intermediate in highly selective 1,3-dipolar cycloaddition reactions constitutes the key step for novel total syntheses of hyacinthacine A2 (3 ) and 7-deoxycasuarine (20 ) by simple transformations of a common isoxozolidine adduct.
126 citations
TL;DR: The isolation from Casuarina equisetifolia L. (Casuarinaceae) bark of casuarine 1, (1R,2R,3R,6S,7S, 7aR)-3-(hydroxymethyl)-1,2,6,7-tetrahydroxypyrrolizidine is reported as mentioned in this paper.
97 citations
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TL;DR: In this article, the inhibitory properties of three plant alkaloids, deoxynojirimycin, 2,5-dihydroxymethyl-3,4-dhydroxypyrrolidine and 1,5 dideoxy-1,5 -imino-D -mannitol towards glycosidases from several sources have been compared.
169 citations
TL;DR: Several polyhydroxy alkaloids, including the eight presently known to occur in plants, have been compared as inhibitors of mouse gut digestive disaccharidases and the indolizidine castanospermine inhibited all activities tested, but others showed a selectivity which could be of value in studies of carbohydrate digestion and errors of metabolism.
132 citations
TL;DR: Polyhydroxy derivatives of octahydroindolizine, piperidine and pyrrolidine have been isolated from plants and microorganisms and many have proved to be potent and specific inhibitors of glycosidase enzymes from a variety of organisms.
Abstract: Polyhydroxy derivatives of octahydroindolizine, piperidine and pyrrolidine have been isolated from plants and microorganisms Many have proved to be potent and specific inhibitors of glycosidase enzymes from a variety of organisms: as such they have potential application in several areas of agricultural and medical research
50 citations
24 citations