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

Nash, Robert J.; Fellows, Linda E.; Dring, J. V.; Fleet, George W. J.; Derome, Andrew E.; Hamor, T. A.; Scofield, A. M.; Watkin, David J.

doi:10.1016/s0040-4039(00)87914-9

Cited by 134 publications

(53 citation statements)

References 9 publications

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“…For example, the pyrrolizidine alkaloids australine 1 [1] and casuarine 2 [2], and related alkaloids [3,4], are powerful inhibitors of glycosidase enzymes and thus exhibit antiviral and anti-HIV activity by effectively inhibiting the enzymatic processing of glycoproteins [5]. More recently, the structurally related polyhydroxylated pyrrolizidine alkaloids, for example, hyacinthacines A 1 (3) and A 2 (4) were isolated from the bulbs of Hyacinthaceae [6]. Compound 3 was found to be an inhibitor of rat intestinal lactase (IC 50 = 4.4 µM) while 4, the C-1 epimer of 3, was a selective inhibitor of amyloglucosidase [6].…”

Section: Polyhydroxylated Pyrrolidine Pyrrolizidine and Indolizidinmentioning

confidence: 99%

Exploiting the borono-Mannich reaction in bioactive alkaloid synthesis

Pyne

Davis

et al. 2008

Pure and Applied Chemistry

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Abstract:We have demonstrated that the borono-Mannich reaction is a versatile and efficient reaction for the diastereoselective preparation of chiral 1,2-amino alcohols. These Mannich products are valuable starting materials as shown in this report by the synthesis of bioactive polyhydroxylated pyrrolizidine and indolizidine alkaloids. Initial studies, directed at the more complex Stemona alkaloids and using the borono-Mannich reaction on cyclic N-acyliminium ions, are encouraging, as demonstrated by the synthesis of the pyrido[1,2-a]azepine core structure of stemocurtisinol.

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Section: Polyhydroxylated Pyrrolidine Pyrrolizidine and Indolizidinmentioning

confidence: 99%

Exploiting the borono-Mannich reaction in bioactive alkaloid synthesis

Pyne

Davis

et al. 2008

Pure and Applied Chemistry

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“…NJ, like its isomers, is an unstable product because of its hemiacetal structure and therefore its corresponding 1-deoxy analog, 1-deoxynojirimycin (9; DNJ), was synthesized by reduction with NaBH 4 or from l-sorbofuranose by Paulsen and coworkers.…”

Section: Natural Occurrence Of Piperidinic Imino Sugarsmentioning

confidence: 99%

“…The main representatives of these different classes are respectively NJ (1), isolated from Streptomycin filtrate, [1] CYB 3 (2), found in the seeds and leaves of Castanospermum australe, [2] swainsonine (3), isolated from Swainsona canescens in 1979, [3] alexine (4), isolated from Alexa leiopetala, [4] and calystegines like 5 present in the roots of Lycium chinense [5] (Figure 1). …”

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Total Synthesis of Piperidine Azasugars

et al. 2005

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Since the discovery of nojirimycin, a glycosidase inhibitor, polyhydroxylated piperidines (also called azasugars: the ring O‐atom of a carbohydrate is replaced by nitrogen) have attracted considerable attention and have been the target of numerous synthetic strategies during the last decade. The efficient synthesis of naturally occurring azasugars and their analogs is of considerable importance due to their potential glycosidase inhibitor properties. Some of them have been widely investigated as candidates for drugs to treat a variety of carbohydrate‐mediated diseases such as diabetes, viral infections, including HIV, cancer metastasis, hepatitis, and Gaucher’s disease. This microreview focuses on recent syntheses of azasugars. In addition, the biology of these compounds is briefly considered. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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“…(1)) [7]. This group also includes, australine [8], alexine [9] (7a-epi-australine), several other epi-australines (1-epiaustraline, 3-epi-australine [10], 2,3-diepi-australine, 2,3,7-tri-epiaustraline) [11], 1-epi-australine-2-O--glucoside and the more recently isolated hyacinthacine alkaloids of which nineteen novel compounds have been identified [12]. This group, along with the polyhydroxylated pyrrolidine, piperidine, indolizidine and nortropane alkaloids, have glycosidase inhibitory activities and thus have potential utility as antiviral, anticancer, antidiabetic and antiobesity drugs [7].…”

Section: Introductionmentioning

confidence: 99%

Isolation, Biological Activities, and Synthesis of the Natural Casuarines

Ritthiwigrom

Pyne

2012

Bioactive Natural Products

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This chapter describes the isolation, structure elucidation, glycosidase inhibitory activities, and the synthesis of the four naturally occurring casuarines. These are casuarine, casuarine-6-O-α-d-glucoside, 6-epi-casuarine (uniflorine A), and 3-epi-casuarine. ABSTRACT: This chapter describes the isolation, structure elucidation, glycosidase inhibitory activities and the synthesis of the four naturally occurring casuarines. These are casuarine, casuarine-6-O--D-glucoside, 6-epi-casuarine (uniflorine A) and 3-epicasuarine.

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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

Cited by 134 publications

References 9 publications

Exploiting the borono-Mannich reaction in bioactive alkaloid synthesis

Exploiting the borono-Mannich reaction in bioactive alkaloid synthesis

Recent Advances in the Total Synthesis of Piperidine Azasugars

Isolation, Biological Activities, and Synthesis of the Natural Casuarines

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