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Molecules 2014, 19(2), 1732-1747; doi:10.3390/molecules19021732
Article

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

1,†
, 2,†
, 2
, 2,* , 2
, 2
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, 3
, 1
, 3
 and 1,*
1 Department of Chemistry, Faculty of Science, University Malaya, Kuala Lumpur 50603, Malaysia 2 Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles (ICSN), CNRS, Labex LERMIT, Gif-sur-Yvette Cedex 91198, France 3 Department of Pharmacy, Faculty of Medicine, University Malaya, Kuala Lumpur 50603, Malaysia These authors contributed equally to this work. Dedicated to the memory of Dr. Khalit Mohamad.
* Authors to whom correspondence should be addressed.
Received: 14 November 2013 / Revised: 3 January 2014 / Accepted: 23 January 2014 / Published: 31 January 2014
(This article belongs to the Section Metabolites)
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Abstract

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 (17), 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 IC50 values in the range 15–17 µM, and compounds 3, 6 and 9 exhibited weak binding affinity for the anti-apoptotic protein Mcl-1.
Keywords: Endiandra kingiana; lauraceae; endiandric acids; kingianic acids; anti-apoptotic proteins; Bcl-xL; Mcl-1 Endiandra kingiana; lauraceae; endiandric acids; kingianic acids; anti-apoptotic proteins; Bcl-xL; Mcl-1
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Azmi, M.N.; Gény, C.; Leverrier, A.; Litaudon, M.; Dumontet, V.; Birlirakis, N.; Guéritte, F.; Leong, K.H.; Halim, S.N.A.; Mohamad, K.; Awang, K. Kingianic Acids A–G, Endiandric Acid Analogues from Endiandra kingiana. Molecules 2014, 19, 1732-1747.

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