Antiplasmodial anthraquinones and hemisynthetic derivatives from the leaves of Tectona grandis (Verbenaceae) |
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| Affiliation: | 1. Department of Chemistry, University of Dschang, P.O. Box 67, Dschang, Cameroon;2. Institute of Medical Research and Medicinal Plants Studies (IMPM), P.O. Box 6163, Yaounde, Cameroon;3. Laboratory of Pharmacognosy, Department of Pharmacy, CIRM, University of Liege, B36, 4000 Liege, Belgium;4. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan, PR China;5. Biotechnology Unit, University of Buea, P.O. Box 63, Buea, Cameroon;1. Centre for Atmospheric Science, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK;2. The Nanoscience Centre, Department of Engineering, University of Cambridge, 11 JJ Thomson Avenue, Cambridge CB3 0FF, UK;1. Department of Chemistry, University of Idaho, Moscow, ID 83844-2343, USA;2. Department of Chemistry, University of Utah, Salt Lake City, UT 84112-0850, USA;1. Department of Chemistry and Chemical Engineering, Royal Military College of Canada, PO Box 17000, Station Forces, Kingston, Ontario K7K 7B4, Canada;2. Department of Chemistry, University of Ottawa, 10 Maria Curie, Ottawa, Ontario K1N 6N5, Canada;1. Key Laboratory of Mountain Ecological Restoration and Bioresource Utilization, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, PR China;2. College of Life Science, Sichuan University, Chengdu 610064, PR China;3. Shanghai University of Traditional Chinese Medicine, Shanghai 201203, PR China |
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| Abstract: | Chemical investigation of the methanol extract of the leaves of Tectona grandis led to the isolation of one new anthraquinone derivative, grandiquinone A (3-acetoxy-8-hydroxy-2-methylanthraquinone) (1), along with nine known compounds: 5,8-dihydroxy-2-methylanthraquinone (2), hydroxysesamone (3), 3-hydroxy-2-methylanthraquinone (4), quinizarine (5), betulinic acid (6), ursolic acid (7), tectograndone (8), corosolic acid (9) and sitosterol 3-O-β-d-glucopyranoside (10). Compounds 2 and 3 were isolated for the first time from the leaves of this plant, while 5 has never been reported from the genus Tectona. Hydroxysesamone (3) and tectograndone (8) were subjected to cyclisation and acetylation reactions to afford two hemisynthetic derivatives, 6,9-dihydroxy-2,2-(dimethyldihydropyrano)-3,4-dihydro-2H-benzo[g]chromene-5,10-dione (11) and acetyltectograndone (12) respectively, which are reported here for the first time. The ethyl acetate-soluble portion, some of the isolated compounds and hemisynthetic derivatives were evaluated for their antiplasmodial activity against the multidrug-resistant Dd2 strain of Plasmodium falciparum. Compound 3 showed a prominent activity, while 2, 8, 9, 11 and 12 showed significant in vitro anti-malarial activity. Compound 1 was weakly active in this test. The structures of the compounds were elucidated by spectroscopic methods and comparison of the data with the literature. |
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| Keywords: | Verbenaceae Anthraquinone Napthoquinone Antiplasmodial activity |
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