Staff View: Conolodinines A–D, Aspidosperma–Aspidosperma Bisindole Alkaloids with Antiproliferative Activity from Tabernaemontana corymbosa

Conolodinines A–D, Aspidosperma–Aspidosperma Bisindole Alkaloids with Antiproliferative Activity from Tabernaemontana corymbosa

Examination of the EtOH extract of the leaves of the Malayan Tabernaemontana corymbosa resulted in the isolation of four new (1-4) and two known bisindole alkaloids (5, 6) of the Aspidosperma-Aspidosperma type. The structures of these alkaloids were determined based on analysis of the spectroscopic...

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Main Authors:	Sim, Dawn Su Yin, Navanesan, Suerialoasan, Sim, Kae Shin, Gurusamy, Subramaniam, Lim, Siew Huah, Low, Yun Yee, Kam, Toh Seok
Format:	Article
Published:	American Chemical Society 2019
Subjects:	Q Science (General) QD Chemistry QH Natural history QR Microbiology
Online Access:	http://eprints.um.edu.my/23429/ https://doi.org/10.1021/acs.jnatprod.8b00919
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spelling	my.um.eprints.234292020-01-14T04:24:59Z http://eprints.um.edu.my/23429/ Conolodinines A–D, Aspidosperma–Aspidosperma Bisindole Alkaloids with Antiproliferative Activity from Tabernaemontana corymbosa Sim, Dawn Su Yin Navanesan, Suerialoasan Sim, Kae Shin Gurusamy, Subramaniam Lim, Siew Huah Low, Yun Yee Kam, Toh Seok Q Science (General) QD Chemistry QH Natural history QR Microbiology Examination of the EtOH extract of the leaves of the Malayan Tabernaemontana corymbosa resulted in the isolation of four new (1-4) and two known bisindole alkaloids (5, 6) of the Aspidosperma-Aspidosperma type. The structures of these alkaloids were determined based on analysis of the spectroscopic data (NMR and HRESIMS). X-ray diffraction analyses of the related bisindole alkaloids conophylline (5) and conophyllinine (6) established the absolute configurations. Treatment of the bisindole alkaloid conophylline (5) with benzeneselenic anhydride gave, in addition to the known bisindole polyervinine (7) previously isolated from another Malayan Tabernaemontana, another bisindole product, 8, an isolable tautomer of 7. X-ray diffraction analyses yielded the absolute configurations of both bisindoles and in addition showed that polyervinine (7) exists primarily as the neutral dione structure. The bisindoles (1-8) and the related conophylline-type bisindoles (9-13) 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, A549, HT-29, and HCT 116 cells, with IC50 values for the active compounds in the 0.01-5 μM range. © 2019 American Chemical Society and American Society of Pharmacognosy. American Chemical Society 2019 Article PeerReviewed Sim, Dawn Su Yin and Navanesan, Suerialoasan and Sim, Kae Shin and Gurusamy, Subramaniam and Lim, Siew Huah and Low, Yun Yee and Kam, Toh Seok (2019) Conolodinines A–D, Aspidosperma–Aspidosperma Bisindole Alkaloids with Antiproliferative Activity from Tabernaemontana corymbosa. Journal of Natural Products, 82 (4). pp. 850-858. ISSN 0163-3864 https://doi.org/10.1021/acs.jnatprod.8b00919 doi:10.1021/acs.jnatprod.8b00919
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	Q Science (General) QD Chemistry QH Natural history QR Microbiology
spellingShingle	Q Science (General) QD Chemistry QH Natural history QR Microbiology Sim, Dawn Su Yin Navanesan, Suerialoasan Sim, Kae Shin Gurusamy, Subramaniam Lim, Siew Huah Low, Yun Yee Kam, Toh Seok Conolodinines A–D, Aspidosperma–Aspidosperma Bisindole Alkaloids with Antiproliferative Activity from Tabernaemontana corymbosa
description	Examination of the EtOH extract of the leaves of the Malayan Tabernaemontana corymbosa resulted in the isolation of four new (1-4) and two known bisindole alkaloids (5, 6) of the Aspidosperma-Aspidosperma type. The structures of these alkaloids were determined based on analysis of the spectroscopic data (NMR and HRESIMS). X-ray diffraction analyses of the related bisindole alkaloids conophylline (5) and conophyllinine (6) established the absolute configurations. Treatment of the bisindole alkaloid conophylline (5) with benzeneselenic anhydride gave, in addition to the known bisindole polyervinine (7) previously isolated from another Malayan Tabernaemontana, another bisindole product, 8, an isolable tautomer of 7. X-ray diffraction analyses yielded the absolute configurations of both bisindoles and in addition showed that polyervinine (7) exists primarily as the neutral dione structure. The bisindoles (1-8) and the related conophylline-type bisindoles (9-13) 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, A549, HT-29, and HCT 116 cells, with IC50 values for the active compounds in the 0.01-5 μM range. © 2019 American Chemical Society and American Society of Pharmacognosy.
format	Article
author	Sim, Dawn Su Yin Navanesan, Suerialoasan Sim, Kae Shin Gurusamy, Subramaniam Lim, Siew Huah Low, Yun Yee Kam, Toh Seok
author_facet	Sim, Dawn Su Yin Navanesan, Suerialoasan Sim, Kae Shin Gurusamy, Subramaniam Lim, Siew Huah Low, Yun Yee Kam, Toh Seok
author_sort	Sim, Dawn Su Yin
title	Conolodinines A–D, Aspidosperma–Aspidosperma Bisindole Alkaloids with Antiproliferative Activity from Tabernaemontana corymbosa
title_short	Conolodinines A–D, Aspidosperma–Aspidosperma Bisindole Alkaloids with Antiproliferative Activity from Tabernaemontana corymbosa
title_full	Conolodinines A–D, Aspidosperma–Aspidosperma Bisindole Alkaloids with Antiproliferative Activity from Tabernaemontana corymbosa
title_fullStr	Conolodinines A–D, Aspidosperma–Aspidosperma Bisindole Alkaloids with Antiproliferative Activity from Tabernaemontana corymbosa
title_full_unstemmed	Conolodinines A–D, Aspidosperma–Aspidosperma Bisindole Alkaloids with Antiproliferative Activity from Tabernaemontana corymbosa
title_sort	conolodinines a–d, aspidosperma–aspidosperma bisindole alkaloids with antiproliferative activity from tabernaemontana corymbosa
publisher	American Chemical Society
publishDate	2019
url	http://eprints.um.edu.my/23429/ https://doi.org/10.1021/acs.jnatprod.8b00919
_version_	1657488208365092864
score	13.211869

Conolodinines A–D, Aspidosperma–Aspidosperma Bisindole Alkaloids with Antiproliferative Activity from Tabernaemontana corymbosa

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