Issue 23, 2013

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

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

Supplementary files

Additions and corrections

Article information

Article type
Paper
Submitted
21 Feb 2013
Accepted
24 Apr 2013
First published
25 Apr 2013

Org. Biomol. Chem., 2013,11, 3826-3833

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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