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-1 concentrations) and were found to have in general poor inhibitory act...

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Main Authors:	Jiangseubchatveera N., Bouillon M.E., Liawruangrath B., Liawruangrath S., Nash R.J., Pyne S.G.
Format:	Article
Language:	English
Published:	2014
Online Access:	http://www.scopus.com/inward/record.url?eid=2-s2.0-84884564713&partnerID=40&md5=6b79c1d7dbf6c4e1824089596fd30b86 http://cmuir.cmu.ac.th/handle/6653943832/4763
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Institution:	Chiang Mai University
Language:	English

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spelling	th-cmuir.6653943832-47632014-08-30T02:55:44Z Concise synthesis of (-)-steviamine and analogues and their glycosidase inhibitory activities Jiangseubchatveera N. Bouillon M.E. Liawruangrath B. Liawruangrath S. Nash R.J. Pyne S.G. 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). This journal is © The Royal Society of Chemistry 2013. 2014-08-30T02:55:44Z 2014-08-30T02:55:44Z 2013 Article 14770520 10.1039/c3ob40374b OBCRA http://www.scopus.com/inward/record.url?eid=2-s2.0-84884564713&partnerID=40&md5=6b79c1d7dbf6c4e1824089596fd30b86 http://cmuir.cmu.ac.th/handle/6653943832/4763 English
institution	Chiang Mai University
building	Chiang Mai University Library
country	Thailand
collection	CMU Intellectual Repository
language	English
description	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). This journal is © The Royal Society of Chemistry 2013.
format	Article
author	Jiangseubchatveera N. Bouillon M.E. Liawruangrath B. Liawruangrath S. Nash R.J. Pyne S.G.
spellingShingle	Jiangseubchatveera N. Bouillon M.E. Liawruangrath B. Liawruangrath S. Nash R.J. Pyne S.G. Concise synthesis of (-)-steviamine and analogues and their glycosidase inhibitory activities
author_facet	Jiangseubchatveera N. Bouillon M.E. Liawruangrath B. Liawruangrath S. Nash R.J. Pyne S.G.
author_sort	Jiangseubchatveera N.
title	Concise synthesis of (-)-steviamine and analogues and their glycosidase inhibitory activities
title_short	Concise synthesis of (-)-steviamine and analogues and their glycosidase inhibitory activities
title_full	Concise synthesis of (-)-steviamine and analogues and their glycosidase inhibitory activities
title_fullStr	Concise synthesis of (-)-steviamine and analogues and their glycosidase inhibitory activities
title_full_unstemmed	Concise synthesis of (-)-steviamine and analogues and their glycosidase inhibitory activities
title_sort	concise synthesis of (-)-steviamine and analogues and their glycosidase inhibitory activities
publishDate	2014
url	http://www.scopus.com/inward/record.url?eid=2-s2.0-84884564713&partnerID=40&md5=6b79c1d7dbf6c4e1824089596fd30b86 http://cmuir.cmu.ac.th/handle/6653943832/4763
_version_	1681420298507780096

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

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