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 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.
Department of Chemistry, Faculty of Science, University Malaya, Kuala Lumpur 50603, Malaysia. libra_mine85@yahoo.co.uk.
Mohamad Nurul
MN
Azmi
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles (ICSN), CNRS, Labex LERMIT, Gif-sur-Yvette Cedex 91198, France. charlotte.geny@cnrs.fr.
Charlotte
C
Gény
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles (ICSN), CNRS, Labex LERMIT, Gif-sur-Yvette Cedex 91198, France. aurelie.leverrier@gmail.com.
Aurélie
A
Leverrier
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles (ICSN), CNRS, Labex LERMIT, Gif-sur-Yvette Cedex 91198, France. marc.litaudon@cnrs.fr.
Marc
M
Litaudon
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles (ICSN), CNRS, Labex LERMIT, Gif-sur-Yvette Cedex 91198, France. vincent.dumontet@cnrs.fr.
Vincent
V
Dumontet
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles (ICSN), CNRS, Labex LERMIT, Gif-sur-Yvette Cedex 91198, France. nicolas.birlirakis@cnrs.fr.
Nicolas
N
Birlirakis
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles (ICSN), CNRS, Labex LERMIT, Gif-sur-Yvette Cedex 91198, France. francoise.gueritte@wanadoo.fr.
Françoise
F
Guéritte
Department of Pharmacy, Faculty of Medicine, University Malaya, Kuala Lumpur 50603, Malaysia. Leongkh@um.edu.my.
Kok Hoong
KH
Leong
Department of Chemistry, Faculty of Science, University Malaya, Kuala Lumpur 50603, Malaysia. nadiahhalim@um.edu.my.
Siti Nadiah Abd
SN
Halim
Department of Pharmacy, Faculty of Medicine, University Malaya, Kuala Lumpur 50603, Malaysia. khalitmohamad@um.edu.my.
Khalit
K
Mohamad
Department of Chemistry, Faculty of Science, University Malaya, Kuala Lumpur 50603, Malaysia. khalijah@um.edu.my.
Khalijah
K
Awang
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects; D002264:Carboxylic Acids / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D019073:HT29 Cells; D006801:Humans; D019770:Lauraceae / Q000737:chemistry*; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry* / Q000494:pharmacology; D014961:X-Ray Diffraction
D000972:Antineoplastic Agents, Phytogenic; D002264:Carboxylic Acids; D010936:Plant Extracts; C534861:endiandric acid