Isolation synthesis and glycosidase inhibition profile of 3-epi-casuarine

Ameijde, Jeroen van; Horne, Graeme; Wormald, Mark R.; Dwek, Raymond A.; Nash, Robert J.; Jones, Phillip John; Evinson, Emma L.; Fleet, George W. J.

doi:10.1016/j.tetasy.2006.10.005

Cited by 38 publications

(38 citation statements)

References 47 publications

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“…Furthermore, very few total syntheses of casuarine (1) have been reported to date, [12,13] and no total synthesis of 2 has been previously described. The highly complex and challenging structure of casuarine, as it is the most highly hydroxylated pyrrolizidine alkaloid and possesses six contiguous carbon stereocenters, is presumably responsible for the limited number of synthetic approaches described.…”

Section: Introductionmentioning

confidence: 99%

Total Syntheses of Casuarine and Its 6‐O‐α‐Glucoside: Complementary Inhibition towards Glycoside Hydrolases of the GH31 and GH37 Families

Cardona

Parmeggiani

Faggi

et al. 2009

Chemistry A European J

100

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Total synthesis of naturally occurring casuarine (1) and the first total synthesis of casuarine 6-O-alpha-glucoside (2) were achieved through complete stereoselective nitrone cycloaddition, Tamao-Fleming oxidation and selective alpha-glucosylation as key steps. Biological assays of the two compounds proved their strong and selective inhibitory properties towards glucoamylase NtMGAM and trehalase Tre37A, respectively, which place them among the most powerful inhibitors of these enzymes. The structural determination of the complexes of NtMGAM with 1 and of Tre37A with 2 revealed interesting similarities in the catalytic sites of these two enzymes which belong to different families and clans.

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Section: Introductionmentioning

confidence: 99%

Total Syntheses of Casuarine and Its 6‐O‐α‐Glucoside: Complementary Inhibition towards Glycoside Hydrolases of the GH31 and GH37 Families

Cardona

Parmeggiani

Faggi

et al. 2009

Chemistry A European J

100

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“…700 M). In the same assay, casuarine 1 showed 0% inhibition of this latter enzyme at a concentration of 700 M, while castanospermine ("the bench mark for -D-glucosidase inhibition") had an IC 50 of 20 M [6].…”

Section: Glycosidase Inhibitory Activities Of the Natural Casuarinesmentioning

confidence: 95%

“…The absolute configuration of 3-epi-casuarine 4 was established by Xray crystallographic analysis [6].…”

Section: Isolation Of the Natural Casuarinesmentioning

confidence: 99%

“…In 2006, Izquierdo et al [45] published the synthesis of 3-epi-casuarine 4 in the same year that Fleet et al [6] reported its isolation as a natural product and also its synthesis. The synthesis of 3-epi-casuarine 4 by…”

Section: Synthesis Of 3-epi-casuarinementioning

confidence: 99%

“…Casuarine 1 [1], casuarine-6-O--glucoside 2 [2], 6-epi-casuarine 3 (uniflorine A) [3][4][5], and 3-epi-casuarine 4 [6] are members of the expanding group of polyhydroxylated 3-hydroxymethylpyrrolizidine natural products (Fig. (1)) [7].…”

Section: Introductionmentioning

confidence: 99%

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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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Stereocontrolled Cyclic Nitrone Cycloaddition Strategy for the Synthesis of Pyrrolizidine and Indolizidine Alkaloids

Brandi

Cardona

Cicchi

et al. 2009

Chemistry A European J

236

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The synthesis of polyhydroxylated indolizidines and pyrrolizidines belonging to the class of iminosugars, endowed with a vast and assorted biological activity, can be achieved in a straightforward manner by a general strategy consisting of a highly stereoselective 1,3-dipolar cycloaddition of polyhydroxylated pyrroline-N-oxides followed by simple transformations of the isoxazolidine adducts. The strategy allows the complete control of the relative and absolute stereochemistry of the numerous stereogenic centers decorating these compounds.

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Isolation synthesis and glycosidase inhibition profile of 3-epi-casuarine

Cited by 38 publications

References 47 publications

Total Syntheses of Casuarine and Its 6‐O‐α‐Glucoside: Complementary Inhibition towards Glycoside Hydrolases of the GH31 and GH37 Families

Total Syntheses of Casuarine and Its 6‐O‐α‐Glucoside: Complementary Inhibition towards Glycoside Hydrolases of the GH31 and GH37 Families

Isolation, Biological Activities, and Synthesis of the Natural Casuarines

Stereocontrolled Cyclic Nitrone Cycloaddition Strategy for the Synthesis of Pyrrolizidine and Indolizidine Alkaloids

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