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

Abbas Mollataghi 1 email, A. Hamid A. Hadi 1,* email and Shiau-Chuen Cheah 2,3 email
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; in revised form: 21 March 2012 / Accepted: 22 March 2012 / Published: 5 April 2012
(This article belongs to the Section Natural Products)
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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

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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.

AMA Style

Mollataghi A, Hadi AHA, Cheah S-C. (−)-Kunstleramide, a New Antioxidant and Cytotoxic Dienamide from the Bark of Beilschmiedia kunstleri Gamble. Molecules. 2012; 17(4):4197-4208.

Chicago/Turabian Style

Mollataghi, Abbas; Hadi, A. Hamid A.; Cheah, Shiau-Chuen. 2012. "(−)-Kunstleramide, a New Antioxidant and Cytotoxic Dienamide from the Bark of Beilschmiedia kunstleri Gamble." Molecules 17, no. 4: 4197-4208.

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