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

Authors

Nadechanok Jiangseubchatveera, University of Wollongong
Marc E. Bouillon, University of WollongongFollow
Boonsom Liawruangrath, Chiang Mai University
Saisunee Liawruangrath, Chiang Mai University
Robert J. Nash, Phytoquest Ltd
Stephen G. Pyne, University of WollongongFollow

RIS ID

79924

Publication Details

Jiangseubchatveera, N., Bouillon, M. E., Liawruangrath, B., Liawruangrath, S., Nash, R. J. & Pyne, S. G. (2013). Concise synthesis of (-)-steviamine and analogues and their glycosidase inhibitory activities. Organic and Biomolecular Chemistry, 11 (23), 3826-3833.

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).