Phytochemical investigations of Stemona curtisii and synthetic studies on stemocurtisine alkaloids

The isolation of two new Stemona alkaloids, 1-hydroxyprotostemonine and stemocurtisine N-oxide, and a new benzofuran, stemofuran L, from the root extracts of Stemona curtisii is reported. The major known alkaloids from this plant extract, stemocurtisine, stemocurtisinol, and oxyprotostemonine, were...

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Main Authors: Chaiyong S., Jatisatienr A., Mungkornasawakul P., Sastraruji T., Pyne S., Ung A., Urathamakul T., Lie W.
Format: Journal
Published: 2017
Online Access:https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=78650219547&origin=inward
http://cmuir.cmu.ac.th/jspui/handle/6653943832/43209
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Institution: Chiang Mai University
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spelling th-cmuir.6653943832-432092017-09-28T06:52:01Z Phytochemical investigations of Stemona curtisii and synthetic studies on stemocurtisine alkaloids Chaiyong S. Jatisatienr A. Mungkornasawakul P. Sastraruji T. Pyne S. Ung A. Urathamakul T. Lie W. The isolation of two new Stemona alkaloids, 1-hydroxyprotostemonine and stemocurtisine N-oxide, and a new benzofuran, stemofuran L, from the root extracts of Stemona curtisii is reported. The major known alkaloids from this plant extract, stemocurtisine, stemocurtisinol, and oxyprotostemonine, were also isolated along with oxystemokerrine N-oxide. The nonalkaloid components of this extract included a new benzofuran derivative, stemofuran L, the known stemofurans F, J, and K, dihydro-γ-tocopherol, and stigmasterol. Stemocurtisine and stemocurtisinol were converted to their respective N-oxides by oxidation. Stemocurtisine was converted to a tetracyclic derivative by oxidative cleavage of the γ-butyrolactone ring, while stemocurtisinol gave a novel lactam derivative by oxidative cleavage of the C-4 side chain under basic conditions. The acetylcholinesterase inhibitory activities of some known and new alkaloids and their derivatives are also reported. All were 10-20 times less active as acetylcholinesterase inhibitors than the pyrrolo[1,2-a]azepine Stemona alkaloids stemofoline and 1′,2′-didehydrostemofoline. None of the stemofuran compounds showed significant antibacterial or antifungal activities. © 2010 The American Chemical Society and American Society of Pharmacognosy. 2017-09-28T06:52:01Z 2017-09-28T06:52:01Z 2010-11-29 Journal 01633864 2-s2.0-78650219547 10.1021/np100474y https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=78650219547&origin=inward http://cmuir.cmu.ac.th/jspui/handle/6653943832/43209
institution Chiang Mai University
building Chiang Mai University Library
country Thailand
collection CMU Intellectual Repository
description The isolation of two new Stemona alkaloids, 1-hydroxyprotostemonine and stemocurtisine N-oxide, and a new benzofuran, stemofuran L, from the root extracts of Stemona curtisii is reported. The major known alkaloids from this plant extract, stemocurtisine, stemocurtisinol, and oxyprotostemonine, were also isolated along with oxystemokerrine N-oxide. The nonalkaloid components of this extract included a new benzofuran derivative, stemofuran L, the known stemofurans F, J, and K, dihydro-γ-tocopherol, and stigmasterol. Stemocurtisine and stemocurtisinol were converted to their respective N-oxides by oxidation. Stemocurtisine was converted to a tetracyclic derivative by oxidative cleavage of the γ-butyrolactone ring, while stemocurtisinol gave a novel lactam derivative by oxidative cleavage of the C-4 side chain under basic conditions. The acetylcholinesterase inhibitory activities of some known and new alkaloids and their derivatives are also reported. All were 10-20 times less active as acetylcholinesterase inhibitors than the pyrrolo[1,2-a]azepine Stemona alkaloids stemofoline and 1′,2′-didehydrostemofoline. None of the stemofuran compounds showed significant antibacterial or antifungal activities. © 2010 The American Chemical Society and American Society of Pharmacognosy.
format Journal
author Chaiyong S.
Jatisatienr A.
Mungkornasawakul P.
Sastraruji T.
Pyne S.
Ung A.
Urathamakul T.
Lie W.
spellingShingle Chaiyong S.
Jatisatienr A.
Mungkornasawakul P.
Sastraruji T.
Pyne S.
Ung A.
Urathamakul T.
Lie W.
Phytochemical investigations of Stemona curtisii and synthetic studies on stemocurtisine alkaloids
author_facet Chaiyong S.
Jatisatienr A.
Mungkornasawakul P.
Sastraruji T.
Pyne S.
Ung A.
Urathamakul T.
Lie W.
author_sort Chaiyong S.
title Phytochemical investigations of Stemona curtisii and synthetic studies on stemocurtisine alkaloids
title_short Phytochemical investigations of Stemona curtisii and synthetic studies on stemocurtisine alkaloids
title_full Phytochemical investigations of Stemona curtisii and synthetic studies on stemocurtisine alkaloids
title_fullStr Phytochemical investigations of Stemona curtisii and synthetic studies on stemocurtisine alkaloids
title_full_unstemmed Phytochemical investigations of Stemona curtisii and synthetic studies on stemocurtisine alkaloids
title_sort phytochemical investigations of stemona curtisii and synthetic studies on stemocurtisine alkaloids
publishDate 2017
url https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=78650219547&origin=inward
http://cmuir.cmu.ac.th/jspui/handle/6653943832/43209
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