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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th-cmuir.6653943832-505272018-09-04T04:52:31Z Phytochemical investigations of Stemona curtisii and synthetic studies on stemocurtisine alkaloids Sukanda Chaiyong Araya Jatisatienr Pitchaya Mungkornasawakul Thanapat Sastraruji Stephen G. Pyne Alison T. Ung Thitima Urathamakul Wilford Lie Biochemistry, Genetics and Molecular Biology Chemistry Medicine Pharmacology, Toxicology and Pharmaceutics 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. 2018-09-04T04:41:56Z 2018-09-04T04:41:56Z 2010-11-29 Journal 15206025 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/6653943832/50527 |
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Biochemistry, Genetics and Molecular Biology Chemistry Medicine Pharmacology, Toxicology and Pharmaceutics Sukanda Chaiyong Araya Jatisatienr Pitchaya Mungkornasawakul Thanapat Sastraruji Stephen G. Pyne Alison T. Ung Thitima Urathamakul Wilford Lie Phytochemical investigations of Stemona curtisii and synthetic studies on stemocurtisine alkaloids |
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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 |
Sukanda Chaiyong Araya Jatisatienr Pitchaya Mungkornasawakul Thanapat Sastraruji Stephen G. Pyne Alison T. Ung Thitima Urathamakul Wilford Lie |
author_facet |
Sukanda Chaiyong Araya Jatisatienr Pitchaya Mungkornasawakul Thanapat Sastraruji Stephen G. Pyne Alison T. Ung Thitima Urathamakul Wilford Lie |
author_sort |
Sukanda Chaiyong |
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 |
2018 |
url |
https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=78650219547&origin=inward http://cmuir.cmu.ac.th/jspui/handle/6653943832/50527 |
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1681423605935636480 |