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Kingianic Acids A–G, Endiandric Acid Analogues from Endiandra kingiana

A phytochemical investigation of the methanolic extract of the bark of Endiandra kingiana led to the isolation of seven new tetracyclic endiandric acid analogues, kingianic acids A–G (1–7), together with endiandric acid M (8), tsangibeilin B (9) and endiandric acid (10). Their structures were determ...

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Autores principales: Azmi, Mohamad Nurul, Gény, Charlotte, Leverrier, Aurélie, Litaudon, Marc, Dumontet, Vincent, Birlirakis, Nicolas, Guéritte, Françoise, Leong, Kok Hoong, Halim, Siti Nadiah Abd., Mohamad, Khalit, Awang, Khalijah
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270856/
https://www.ncbi.nlm.nih.gov/pubmed/24492595
http://dx.doi.org/10.3390/molecules19021732
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author Azmi, Mohamad Nurul
Gény, Charlotte
Leverrier, Aurélie
Litaudon, Marc
Dumontet, Vincent
Birlirakis, Nicolas
Guéritte, Françoise
Leong, Kok Hoong
Halim, Siti Nadiah Abd.
Mohamad, Khalit
Awang, Khalijah
author_facet Azmi, Mohamad Nurul
Gény, Charlotte
Leverrier, Aurélie
Litaudon, Marc
Dumontet, Vincent
Birlirakis, Nicolas
Guéritte, Françoise
Leong, Kok Hoong
Halim, Siti Nadiah Abd.
Mohamad, Khalit
Awang, Khalijah
author_sort Azmi, Mohamad Nurul
collection PubMed
description A phytochemical investigation of the methanolic extract of the bark of Endiandra kingiana led to the isolation of seven new tetracyclic endiandric acid analogues, kingianic acids A–G (1–7), together with endiandric acid M (8), tsangibeilin B (9) and endiandric acid (10). Their structures were determined by 1D- and 2D-NMR analysis in combination with HRMS experiments. The structure of compounds 9 and 10 were confirmed by single-crystal X-ray diffraction analysis. These compounds were screened for Bcl-xL and Mcl-1 binding affinities and cytotoxic activity on various cancer cell lines. Compound 5 showed moderate cytotoxic activity against human colorectal adeno-carcinoma (HT-29) and lung adenocarcinoma epithelial (A549) cell lines, with IC(50) values in the range 15–17 µM, and compounds 3, 6 and 9 exhibited weak binding affinity for the anti-apoptotic protein Mcl-1.
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spelling pubmed-62708562018-12-20 Kingianic Acids A–G, Endiandric Acid Analogues from Endiandra kingiana Azmi, Mohamad Nurul Gény, Charlotte Leverrier, Aurélie Litaudon, Marc Dumontet, Vincent Birlirakis, Nicolas Guéritte, Françoise Leong, Kok Hoong Halim, Siti Nadiah Abd. Mohamad, Khalit Awang, Khalijah Molecules Article A phytochemical investigation of the methanolic extract of the bark of Endiandra kingiana led to the isolation of seven new tetracyclic endiandric acid analogues, kingianic acids A–G (1–7), together with endiandric acid M (8), tsangibeilin B (9) and endiandric acid (10). Their structures were determined by 1D- and 2D-NMR analysis in combination with HRMS experiments. The structure of compounds 9 and 10 were confirmed by single-crystal X-ray diffraction analysis. These compounds were screened for Bcl-xL and Mcl-1 binding affinities and cytotoxic activity on various cancer cell lines. Compound 5 showed moderate cytotoxic activity against human colorectal adeno-carcinoma (HT-29) and lung adenocarcinoma epithelial (A549) cell lines, with IC(50) values in the range 15–17 µM, and compounds 3, 6 and 9 exhibited weak binding affinity for the anti-apoptotic protein Mcl-1. MDPI 2014-01-31 /pmc/articles/PMC6270856/ /pubmed/24492595 http://dx.doi.org/10.3390/molecules19021732 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Azmi, Mohamad Nurul
Gény, Charlotte
Leverrier, Aurélie
Litaudon, Marc
Dumontet, Vincent
Birlirakis, Nicolas
Guéritte, Françoise
Leong, Kok Hoong
Halim, Siti Nadiah Abd.
Mohamad, Khalit
Awang, Khalijah
Kingianic Acids A–G, Endiandric Acid Analogues from Endiandra kingiana
title Kingianic Acids A–G, Endiandric Acid Analogues from Endiandra kingiana
title_full Kingianic Acids A–G, Endiandric Acid Analogues from Endiandra kingiana
title_fullStr Kingianic Acids A–G, Endiandric Acid Analogues from Endiandra kingiana
title_full_unstemmed Kingianic Acids A–G, Endiandric Acid Analogues from Endiandra kingiana
title_short Kingianic Acids A–G, Endiandric Acid Analogues from Endiandra kingiana
title_sort kingianic acids a–g, endiandric acid analogues from endiandra kingiana
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270856/
https://www.ncbi.nlm.nih.gov/pubmed/24492595
http://dx.doi.org/10.3390/molecules19021732
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