Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines

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• 作者：Koushik Saha (1) (3)
  Kok Wai Lam (1) (4)
  Faridah Abas (1) (5)
  A. Sazali Hamzah (7)
  Johnson Stanslas (6)
  Lim Siang Hui (8)
  Nordin H. Lajis (1) (2)
  
• 关键词：Anthraquinones ; Synthesis ; Cytotoxicity ; Antioxidant activity
• 刊名：Medicinal Chemistry Research
• 出版年：2013
• 出版时间：May 2013
• 年：2013
• 卷：22
• 期：5
• 页码：2093-2104
• 全文大小：372KB
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• 作者单位：Koushik Saha (1) (3)
  Kok Wai Lam (1) (4)
  Faridah Abas (1) (5)
  A. Sazali Hamzah (7)
  Johnson Stanslas (6)
  Lim Siang Hui (8)
  Nordin H. Lajis (1) (2)
  
  1. Laboratory of Natural Products, Institute of Bioscience, University Putra Malaysia (UPM), 43400, Serdang, Selangor Darul Ehsan, Malaysia
  3. Department of Chemistry, Jahangirnagar University, Savar, Dhaka, 1342, Bangladesh
  4. Drug and Herbal Research Centre Faculty of Pharmacy, Universiti Kebangsaan Malaysia, Jalan Raja Muda Abd. Aziz, 50300, Kuala Lumpur, Malaysia
  5. Department of Food Science, Faculty of Food Science and Technology, University Putra Malaysia (UPM), 43400, Serdang, Selangor Darul Ehsan, Malaysia
  7. Department of Chemistry, Faculty of Applied Science, University Technology MARA, 40450, Shah Alam, Selangor Darul Ehsan, Malaysia
  6. Department of Medicine, Faculty of Medicine and Health Science, University Putra Malaysia (UPM), 43400, Serdang, Selangor Darul Ehsan, Malaysia
  8. Department of Biomedical Science, Faculty of Medicine and Health Science, University Putra Malaysia (UPM), 43400, Serdang, Selangor Darul Ehsan, Malaysia
  2. Scientific Chairs Unit, Taibah University, P.O. Box 30001, Madinah al-Munawarah, 41311, Saudi Arabia
  

文摘

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-?μM. 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.