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...
Main Authors: | , , , , , , , |
---|---|
Format: | Article |
Published: |
American Chemical Society
2018
|
Subjects: |
_version_ | 1796960851383549952 |
---|---|
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. |
first_indexed | 2024-03-06T05:50:46Z |
format | Article |
id | um.eprints-20287 |
institution | Universiti Malaya |
last_indexed | 2024-03-06T05:50:46Z |
publishDate | 2018 |
publisher | American Chemical Society |
record_format | dspace |
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 |
work_keys_str_mv | AT yeapjoannesoonyee ajmalineoxindoleandcytotoxicmacrolineakuammilinebisindolealkaloidsfromalstoniapenangiana AT navanesansuerialoasan ajmalineoxindoleandcytotoxicmacrolineakuammilinebisindolealkaloidsfromalstoniapenangiana AT simkaeshin ajmalineoxindoleandcytotoxicmacrolineakuammilinebisindolealkaloidsfromalstoniapenangiana AT yongkienthai ajmalineoxindoleandcytotoxicmacrolineakuammilinebisindolealkaloidsfromalstoniapenangiana AT gurusamysubramaniam ajmalineoxindoleandcytotoxicmacrolineakuammilinebisindolealkaloidsfromalstoniapenangiana AT limsiewhuah ajmalineoxindoleandcytotoxicmacrolineakuammilinebisindolealkaloidsfromalstoniapenangiana AT lowyunyee ajmalineoxindoleandcytotoxicmacrolineakuammilinebisindolealkaloidsfromalstoniapenangiana AT kamtohseok ajmalineoxindoleandcytotoxicmacrolineakuammilinebisindolealkaloidsfromalstoniapenangiana |