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

Mohamad Nurul Azmi; Charlotte Gény; Aurélie Leverrier; Marc Litaudon; Vincent Dumontet; Nicolas Birlirakis; Françoise Guéritte; Kok Hoong Leong; Siti Nadiah Abd Halim; Khalit Mohamad; Khalijah Awang

doi:10.3390/molecules19021732

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

Mohamad Nurul Azmi, Charlotte Gény, Aurélie Leverrier, Marc Litaudon, Vincent Dumontet, Nicolas Birlirakis, Françoise Guéritte, Kok Hoong Leong, Siti Nadiah Abd Halim, Khalit Mohamad, Khalijah Awang

Research output: Contribution to journal › Article › peer-review

19 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1732-1747
Number of pages	16
Journal	Molecules
Volume	19
Issue number	2
DOIs	https://doi.org/10.3390/molecules19021732
Publication status	Published - Feb 2014
Externally published	Yes

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.3390/molecules19021732

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title = "Kingianic Acids A-G, Endiandric Acid Analogues from Endiandra kingiana",

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.",

author = "Azmi, {Mohamad Nurul} and Charlotte G{\'e}ny and Aur{\'e}lie Leverrier and Marc Litaudon and Vincent Dumontet and Nicolas Birlirakis and Fran{\c c}oise Gu{\'e}ritte and Leong, {Kok Hoong} and Halim, {Siti Nadiah Abd} and Khalit Mohamad and Khalijah Awang",

year = "2014",

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doi = "10.3390/molecules19021732",

language = "English",

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AU - Azmi, Mohamad Nurul

AU - Gény, Charlotte

AU - Leverrier, Aurélie

AU - Litaudon, Marc

AU - Dumontet, Vincent

AU - Birlirakis, Nicolas

AU - Guéritte, Françoise

AU - Leong, Kok Hoong

AU - Halim, Siti Nadiah Abd

AU - Mohamad, Khalit

AU - Awang, Khalijah

PY - 2014/2

Y1 - 2014/2

N2 - 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.

AB - 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.

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

Abstract

All Science Journal Classification (ASJC) codes

UN SDGs

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