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Macroline, talpinine, and sarpagine alkaloids from Alstonia penangiana. An NMR-based method for differentiating between A. penangiana and A. macrophylla

Fourteen previously undescribed alkaloids comprising two N-1-hydroxymethylmacroline alkaloids, one talpinine-type oxindole acetal, a pair of equilibrating talpinine-type oxindole hemiacetals, eight oxidized derivatives of sarpagine- and akuammiline-type indole alkaloids, in addition to alstochalotin...

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Main Authors:	Yeap, Joanne Soon Yee, Tan, Chun Hoe, Yong, Kien Thai, Lim, Kuan Hon, Lim, Siew Huah, Low, Yun Yee, Kam, Toh Seok
Format:	Article
Published:	Elsevier 2020
Subjects:	QD Chemistry QH Natural history
Online Access:	http://eprints.um.edu.my/24656/ https://doi.org/10.1016/j.phytochem.2020.112391
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id	my.um.eprints.24656
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spelling	my.um.eprints.246562020-06-04T04:18:37Z http://eprints.um.edu.my/24656/ Macroline, talpinine, and sarpagine alkaloids from Alstonia penangiana. An NMR-based method for differentiating between A. penangiana and A. macrophylla Yeap, Joanne Soon Yee Tan, Chun Hoe Yong, Kien Thai Lim, Kuan Hon Lim, Siew Huah Low, Yun Yee Kam, Toh Seok QD Chemistry QH Natural history Fourteen previously undescribed alkaloids comprising two N-1-hydroxymethylmacroline alkaloids, one talpinine-type oxindole acetal, a pair of equilibrating talpinine-type oxindole hemiacetals, eight oxidized derivatives of sarpagine- and akuammiline-type indole alkaloids, in addition to alstochalotine a diastereomer of gelsochalotine recently isolated from Gelsemium elegans, were isolated from the leaf and stem-bark extracts of Alstonia penangiana. The structures and relative configurations of these alkaloids were established using NMR, MS, and in one instance, confirmed by X-ray diffraction analysis. An NMR-based method is described as a useful chemotaxonomic tool for differentiating between A. penangiana and A. macrophylla. Several of the alkaloids isolated showed appreciable growth inhibitory effects when tested against a number of human cancer cell lines. © 2020 Elsevier Ltd Elsevier 2020 Article PeerReviewed Yeap, Joanne Soon Yee and Tan, Chun Hoe and Yong, Kien Thai and Lim, Kuan Hon and Lim, Siew Huah and Low, Yun Yee and Kam, Toh Seok (2020) Macroline, talpinine, and sarpagine alkaloids from Alstonia penangiana. An NMR-based method for differentiating between A. penangiana and A. macrophylla. Phytochemistry, 176. p. 112391. ISSN 0031-9422 https://doi.org/10.1016/j.phytochem.2020.112391 doi:10.1016/j.phytochem.2020.112391
institution	Universiti Malaya
building	UM Library
collection	Institutional Repository
continent	Asia
country	Malaysia
content_provider	Universiti Malaya
content_source	UM Research Repository
url_provider	http://eprints.um.edu.my/
topic	QD Chemistry QH Natural history
spellingShingle	QD Chemistry QH Natural history Yeap, Joanne Soon Yee Tan, Chun Hoe Yong, Kien Thai Lim, Kuan Hon Lim, Siew Huah Low, Yun Yee Kam, Toh Seok Macroline, talpinine, and sarpagine alkaloids from Alstonia penangiana. An NMR-based method for differentiating between A. penangiana and A. macrophylla
description	Fourteen previously undescribed alkaloids comprising two N-1-hydroxymethylmacroline alkaloids, one talpinine-type oxindole acetal, a pair of equilibrating talpinine-type oxindole hemiacetals, eight oxidized derivatives of sarpagine- and akuammiline-type indole alkaloids, in addition to alstochalotine a diastereomer of gelsochalotine recently isolated from Gelsemium elegans, were isolated from the leaf and stem-bark extracts of Alstonia penangiana. The structures and relative configurations of these alkaloids were established using NMR, MS, and in one instance, confirmed by X-ray diffraction analysis. An NMR-based method is described as a useful chemotaxonomic tool for differentiating between A. penangiana and A. macrophylla. Several of the alkaloids isolated showed appreciable growth inhibitory effects when tested against a number of human cancer cell lines. © 2020 Elsevier Ltd
format	Article
author	Yeap, Joanne Soon Yee Tan, Chun Hoe Yong, Kien Thai Lim, Kuan Hon Lim, Siew Huah Low, Yun Yee Kam, Toh Seok
author_facet	Yeap, Joanne Soon Yee Tan, Chun Hoe Yong, Kien Thai Lim, Kuan Hon Lim, Siew Huah Low, Yun Yee Kam, Toh Seok
author_sort	Yeap, Joanne Soon Yee
title	Macroline, talpinine, and sarpagine alkaloids from Alstonia penangiana. An NMR-based method for differentiating between A. penangiana and A. macrophylla
title_short	Macroline, talpinine, and sarpagine alkaloids from Alstonia penangiana. An NMR-based method for differentiating between A. penangiana and A. macrophylla
title_full	Macroline, talpinine, and sarpagine alkaloids from Alstonia penangiana. An NMR-based method for differentiating between A. penangiana and A. macrophylla
title_fullStr	Macroline, talpinine, and sarpagine alkaloids from Alstonia penangiana. An NMR-based method for differentiating between A. penangiana and A. macrophylla
title_full_unstemmed	Macroline, talpinine, and sarpagine alkaloids from Alstonia penangiana. An NMR-based method for differentiating between A. penangiana and A. macrophylla
title_sort	macroline, talpinine, and sarpagine alkaloids from alstonia penangiana. an nmr-based method for differentiating between a. penangiana and a. macrophylla
publisher	Elsevier
publishDate	2020
url	http://eprints.um.edu.my/24656/ https://doi.org/10.1016/j.phytochem.2020.112391
_version_	1669008009299230720
score	13.211869

Macroline, talpinine, and sarpagine alkaloids from Alstonia penangiana. An NMR-based method for differentiating between A. penangiana and A. macrophylla

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