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Issue 23, 2013
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Concise synthesis of (−)-steviamine and analogues and their glycosidase inhibitory activities

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Abstract

A concise synthesis of (−)-steviamine is reported along with the synthesis of its analogues 10-nor-steviamine, 10-nor-ent-steviamine and 5-epi-ent-steviamine. These compounds were tested against twelve glycosidases (at 143 μg mL−1 concentrations) and were found to have in general poor inhibitory activity against most enzymes. The 10-nor analogues however, showed 50–54% inhibition of α-L-rhamnosidase from Penicillium decumbens while one of these, 10-nor-steviamine, showed 51% inhibition of N-acetyl-β-D-glucosaminidase (from Jack bean) at the same concentration (760 μM).

Graphical abstract: Concise synthesis of (−)-steviamine and analogues and their glycosidase inhibitory activities

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Publication details

The article was received on 21 Feb 2013, accepted on 24 Apr 2013 and first published on 25 Apr 2013


Article type: Paper
DOI: 10.1039/C3OB40374B
Citation: Org. Biomol. Chem., 2013,11, 3826-3833
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    Concise synthesis of (−)-steviamine and analogues and their glycosidase inhibitory activities

    N. Jiangseubchatveera, M. E. Bouillon, B. Liawruangrath, S. Liawruangrath, R. J. Nash and S. G. Pyne, Org. Biomol. Chem., 2013, 11, 3826
    DOI: 10.1039/C3OB40374B

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