Ajmaline, Oxindole, and Cytotoxic Macroline–Akuammiline Bisindole Alkaloids from Alstonia penangiana

Examination of the EtOH extract of the Malayan Alstonia penangiana resulted in the isolation of 10 new alkaloids, comprising two ajmaline (1, 2), four macroline oxindole (3-6), and four macroline-akuammiline bisindole alkaloids (7-10). The structures of these alkaloids were determined based on analy...

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Main Authors: Yeap, Joanne Soon Yee, Navanesan, Suerialoasan, Sim, Kae Shin, Yong, Kien Thai, Gurusamy, Subramaniam, Lim, Siew Huah, Low, Yun Yee, Kam, Toh Seok
Format: Article
Published: American Chemical Society 2018
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author Yeap, Joanne Soon Yee
Navanesan, Suerialoasan
Sim, Kae Shin
Yong, Kien Thai
Gurusamy, Subramaniam
Lim, Siew Huah
Low, Yun Yee
Kam, Toh Seok
author_facet Yeap, Joanne Soon Yee
Navanesan, Suerialoasan
Sim, Kae Shin
Yong, Kien Thai
Gurusamy, Subramaniam
Lim, Siew Huah
Low, Yun Yee
Kam, Toh Seok
author_sort Yeap, Joanne Soon Yee
collection UM
description Examination of the EtOH extract of the Malayan Alstonia penangiana resulted in the isolation of 10 new alkaloids, comprising two ajmaline (1, 2), four macroline oxindole (3-6), and four macroline-akuammiline bisindole alkaloids (7-10). The structures of these alkaloids were determined based on analysis of the spectroscopic data and, in the case of the oxindole 6 and the bisindole alkaloid 7, also confirmed by X-ray diffraction analysis. The bisindole alkaloids 7 and 8 showed pronounced in vitro growth inhibitory activity against an array of human cancer cell lines, including KB, vincristine-resistant KB, PC-3, LNCaP, MCF7, MDA-MB-231, HT-29, HCT 116, and A549 cells with IC50 values in the 0.3-8.3 μM range.
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spelling um.eprints-202872019-02-13T06:28:27Z http://eprints.um.edu.my/20287/ Ajmaline, Oxindole, and Cytotoxic Macroline–Akuammiline Bisindole Alkaloids from Alstonia penangiana Yeap, Joanne Soon Yee Navanesan, Suerialoasan Sim, Kae Shin Yong, Kien Thai Gurusamy, Subramaniam Lim, Siew Huah Low, Yun Yee Kam, Toh Seok Q Science (General) QD Chemistry QH Natural history Examination of the EtOH extract of the Malayan Alstonia penangiana resulted in the isolation of 10 new alkaloids, comprising two ajmaline (1, 2), four macroline oxindole (3-6), and four macroline-akuammiline bisindole alkaloids (7-10). The structures of these alkaloids were determined based on analysis of the spectroscopic data and, in the case of the oxindole 6 and the bisindole alkaloid 7, also confirmed by X-ray diffraction analysis. The bisindole alkaloids 7 and 8 showed pronounced in vitro growth inhibitory activity against an array of human cancer cell lines, including KB, vincristine-resistant KB, PC-3, LNCaP, MCF7, MDA-MB-231, HT-29, HCT 116, and A549 cells with IC50 values in the 0.3-8.3 μM range. American Chemical Society 2018 Article PeerReviewed Yeap, Joanne Soon Yee and Navanesan, Suerialoasan and Sim, Kae Shin and Yong, Kien Thai and Gurusamy, Subramaniam and Lim, Siew Huah and Low, Yun Yee and Kam, Toh Seok (2018) Ajmaline, Oxindole, and Cytotoxic Macroline–Akuammiline Bisindole Alkaloids from Alstonia penangiana. Journal of Natural Products, 81 (5). pp. 1266-1277. ISSN 0163-3864, DOI https://doi.org/10.1021/acs.jnatprod.8b00170 <https://doi.org/10.1021/acs.jnatprod.8b00170>. https://doi.org/10.1021/acs.jnatprod.8b00170 doi:10.1021/acs.jnatprod.8b00170
spellingShingle Q Science (General)
QD Chemistry
QH Natural history
Yeap, Joanne Soon Yee
Navanesan, Suerialoasan
Sim, Kae Shin
Yong, Kien Thai
Gurusamy, Subramaniam
Lim, Siew Huah
Low, Yun Yee
Kam, Toh Seok
Ajmaline, Oxindole, and Cytotoxic Macroline–Akuammiline Bisindole Alkaloids from Alstonia penangiana
title Ajmaline, Oxindole, and Cytotoxic Macroline–Akuammiline Bisindole Alkaloids from Alstonia penangiana
title_full Ajmaline, Oxindole, and Cytotoxic Macroline–Akuammiline Bisindole Alkaloids from Alstonia penangiana
title_fullStr Ajmaline, Oxindole, and Cytotoxic Macroline–Akuammiline Bisindole Alkaloids from Alstonia penangiana
title_full_unstemmed Ajmaline, Oxindole, and Cytotoxic Macroline–Akuammiline Bisindole Alkaloids from Alstonia penangiana
title_short Ajmaline, Oxindole, and Cytotoxic Macroline–Akuammiline Bisindole Alkaloids from Alstonia penangiana
title_sort ajmaline oxindole and cytotoxic macroline akuammiline bisindole alkaloids from alstonia penangiana
topic Q Science (General)
QD Chemistry
QH Natural history
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