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

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 < sup > -1 < /sup > concentrations) and were found to have...

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Bibliographic Details
Main Authors: Nadechanok Jiangseubchatveera, Marc E. Bouillon, Boonsom Liawruangrath, Saisunee Liawruangrath, Robert J. Nash, Stephen G. Pyne
Format: Journal
Published: 2018
Online Access:https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84884564713&origin=inward
http://cmuir.cmu.ac.th/jspui/handle/6653943832/48303
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Institution: Chiang Mai University
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Summary: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 < sup > -1 < /sup > 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). © The Royal Society of Chemistry 2013.