Next Article in Journal
Synthesis and NMR Spectral Studies of the 7-C60-Adduct of N,N-(Tetrachlorophthaloyl) Dehydroabietylamine
Previous Article in Journal
Synthetic Study on the Relationship Between Structure and Sweet Taste Properties of Steviol Glycosides
Molecules 2012, 17(4), 4197-4208; doi:10.3390/molecules17044197
Article

(−)-Kunstleramide, a New Antioxidant and Cytotoxic Dienamide from the Bark of Beilschmiedia kunstleri Gamble

1
, 1,*  and 2,3
1 Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia 2 Centre for Natural Products Research and Drug Discovery (CENAR), Department of Pharmacology, Faculty of Medicine, University of Malaya, Kuala Lumpur 50603, Malaysia 3 School of Medicine, Faculty of Medical Sciences, UCSI University, Kuala Lumpur 56000, Malaysia
* Author to whom correspondence should be addressed.
Received: 13 February 2012 / Revised: 21 March 2012 / Accepted: 22 March 2012 / Published: 5 April 2012
(This article belongs to the Section Metabolites)
View Full-Text   |   Download PDF [340 KB, uploaded 18 June 2014]   |   Browse Figures

Abstract

A new dienamide, (2E,4E)-7-(3',4'-dimethoxyphenyl)-N-ethyl-6-(R)-hydroxyhepta- 2,4-dienamide, named (-)-kunstleramide (1), were isolated from the bark of Beilschmiedia kunstleri Gamble together with one neolignan: (+)-kunstlerone (2) and seven known alkaloids: (+)-nornuciferine (3), (-)-isocaryachine (4), (+)-cassythicine (5), (+)-laurotetanine (6), (+)-boldine (7), noratherosperminine (8), (+)-N-demethylphyllocaryptine (9). Their structures were established from spectroscopic techniques, most notably 1D- and 2D-NMR, UV, IR, OR, circular dichroism (CD) spectra and LCMS-IT-TOF. (-)-Kunstleramide (1) exhibited very poor dose-dependent inhibition of DPPH activity, with an IC50 value of 179.5 ± 4.4 μg/mL, but showed a moderate cytotoxic effect on MTT assays of A375, A549, HT-29, PC-3 and WRL-68 with EC50 values of 64.65, 44.74, 55.94, 73.87 and 70.95 µg/mL, respectively.
Keywords: Beilschmiedia kunstleri; lauraceae; alkaloid; dienamide; antioxidant; cytotoxicity Beilschmiedia kunstleri; lauraceae; alkaloid; dienamide; antioxidant; cytotoxicity
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.

Share & Cite This Article

Export to BibTeX |
EndNote


MDPI and ACS Style

Mollataghi, A.; Hadi, A.H.A.; Cheah, S.-C. (−)-Kunstleramide, a New Antioxidant and Cytotoxic Dienamide from the Bark of Beilschmiedia kunstleri Gamble. Molecules 2012, 17, 4197-4208.

View more citation formats

Supplement

Related Articles

Article Metrics

Comments

Citing Articles

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert