Molecules 2014, 19(2), 1732-1747; https://doi.org/10.3390/molecules19021732
Kingianic Acids A–G, Endiandric Acid Analogues from Endiandra kingiana
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 Natural Products Chemistry)
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 (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 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. View Full-TextKeywords:
Endiandra kingiana; lauraceae; endiandric acids; kingianic acids; anti-apoptotic proteins; Bcl-xL; Mcl-1
▼
Figures
Graphical abstract
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
Share & Cite This Article
MDPI and ACS Style
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.
Related Articles
Article Metrics
Comments
[Return to top]
Molecules
EISSN 1420-3049
Published by MDPI AG, Basel, Switzerland
RSS
E-Mail Table of Contents Alert