Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation aga
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Med Chem Res (2013) 22:2093–2104 DOI 10.1007/s00044-012-0197-5
ORIGINAL RESEARCH
Synthesis of damnacanthal, a naturally occurring 9,10anthraquinone and its analogues, and its biological evaluation against five cancer cell lines Koushik Saha • Kok Wai Lam • Faridah Abas A. Sazali Hamzah • Johnson Stanslas • Lim Siang Hui • Nordin H. Lajis
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Received: 2 February 2012 / Accepted: 8 August 2012 / Published online: 13 September 2012 Ó Springer Science+Business Media, LLC 2012
Abstract Damnacanthal and nordamnacanthal, two naturally occurring 9,10-anthraquinones, and their analogues were synthesized. Cytotoxic activity against five cancer cell lines was evaluated using MTT assay. 2-Bromomethyl-1,3-dimethoxyanthraquinone was found to display the highest activity against all cell lines with IC50 range of 2–8 lM. Structure– activity relationship (SAR) assessment was considered to rationalise the cytotoxic effect. Bromomethyl group at position C-2 of the anthraquinone was found to be important in exerting cytotoxic activity of this class of compounds. The presence of the flanking methoxyl or hydroxyl groups at C-1 and C-3 also contributes to this activity. Finally, the antioxidant effect of these compounds was evaluated. MTT assay was used to measure the cytotoxicity against different cancer
cell lines. Antioxidant activity was measured by FTC and TBA methods. Only two anthraquinones, damnacanthal and nordamnacanthal, were found to be antioxidative.
K. Saha K. W. Lam F. Abas N. H. Lajis (&) Laboratory of Natural Products, Institute of Bioscience, University Putra Malaysia (UPM), 43400 Serdang, Selangor Darul Ehsan, Malaysia e-mail: [email protected]
F. Abas Department of Food Science, Faculty of Food Science and Technology, University Putra Malaysia (UPM), 43400 Serdang, Selangor Darul Ehsan, Malaysia e-mail: [email protected]
Present Address: N. H. Lajis Scientific Chairs Unit, Taibah University, P.O. Box 30001, Madinah al-Munawarah 41311, Saudi Arabia
A. Sazali Hamzah Department of Chemistry, Faculty of Applied Science, University Technology MARA, 40450 Shah Alam, Selangor Darul Ehsan, Malaysia e-mail: [email protected]
K. Saha Department of Chemistry, Jahangirnagar University, Savar, Dhaka 1342, Bangladesh e-mail: [email protected]
J. Stanslas Department of Medicine, Faculty of Medicine and Health Science, University Putra Malaysia (UPM), 43400 Serdang, Selangor Darul Ehsan, Malaysia e-mail: [email protected]
K. W. Lam Drug and Herbal Research Centre Faculty of Pharmacy, Universiti Kebangsaan Malaysia, Jalan Raja Muda Abd. Aziz, 50300 Kuala Lumpur, Malaysia e-mail: [email protected]
Keywords Anthraquinones Synthesis Cytotoxicity Antioxidant activity
Introduction Anthraquinones continue to attract researchers due to its diverse potential uses. 9,10-Anthraquinone derivatives exhibit a quite potent anticancer activity
interest among pharmacological are known to (Jin et al., 2001;
L. S. Hui Department of Biomedical Science, Faculty of Medicine and Health Science, Uni
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