Synthesis and cytotoxicity evaluation of A-ring derivatives of cycloartanone |
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| Institution: | 1. Facultad de Ciencias Exactas, Universidad Nacional de Salta (UNSa), 4400 Salta, Argentina;3. Universidad de Buenos Aires, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellón 2 – (1428), Buenos Aires, Argentina;4. CONICET-Universidad de Buenos Aires, Unidad de Microanálisis y Métodos Físicos en Química Orgánica (UMYMFOR), Buenos Aires, Argentina;1. Departamento de Química, Universidade Federal de Minas Gerais, Avenida Presidente Antônio Carlos, 6627, Pampulha, 31270-901, Belo Horizonte-MG, Brazil;2. Instituto de Química, Universidade Federal de Alfenas, Rua Gabriel Monteiro da Silva, 700, Centro, 37130-000, Alfenas-MG, Brazil;3. Departamento de Nutrição e Saúde, Universidade Federal de Viçosa, Avenida Peter Henry Rolfs, s/n, Campus Universitário, 36570-900, Viçosa-MG, Brazil;4. Escola de Farmácia, Universidade Federal de Ouro Preto, Rua Costa Sena, 171, Centro, 35400-000, Ouro Preto-MG, Brazil;5. Departamento de Biodiversidade, Evolução e Meio Ambiente, Universidade Federal de Ouro Preto, Campus Universitário do Morro do Cruzeiro, Rua Professor Paulo Magalhães Gomes, s/n, 35400-000, Ouro Preto-MG, Brazil;1. Pharmacy College, Jiangxi University of Traditional Chinese Medicine, 818 Xinwan Avenue, Nanchang 330004, Jiangxi, PR China;2. Technology Center, Jiangzhong Group, 618 Huoju Road, Nanchang 330096, Jiangxi, PR China;3. Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, PR China;1. Marine Drugs Research Center, College of Pharmacy, Jinan University, Guangzhou 510632, China;2. State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, and Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, 830011, China;1. Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 404, Taiwan;2. Faculty of Pharmacy, School of Pharmaceutical Sciences, National Yang-Ming University, Taipei 112, Taiwan;3. Department of Medical Research, China Medical University Hospital, China Medical University, Taichung 404, Taiwan;4. Department of Forestry, National Chung-Hsing University, Taichung 402, Taiwan;5. Agricultural Biotechnology Research Center, Academia Sinica, Taipei 115, Taiwan;6. Department of Cosmeceutics, China Medical University Hospital, China Medical University, Taichung 404, Taiwan;7. Department of Exercise Health Science, National Taiwan University of Physical Eucation and Sport, Taichung 404, Taiwan;8. Department of Biotechnology, Asia University, Taichung 413, Taiwan |
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| Abstract: | Sixteen derivatives, eight of which are new compounds, were prepared from cycloartenone (1) and cycloartanone (2), and the cytotoxic activity of 14 of these compounds, together with 1 and 2, was evaluated against a panel of four cell lines. Compound 1 was obtained from the epiphyte plant Tillandsia tenuifolia collected at Salta, Argentina. Due to chemoselectivity and regioselectivity problems observed in the reactions of compound 1, this substance was hydrogenated to compound 2. The attempted transformations were focused on ring A of the cited triterpenes with the aim to verify previous structure-activity relationships obtained from related compounds. The cytotoxicity results of the derivatives showed that only the diosphenol 13 displayed significant activity against all the tested cell lines. These results show that an oxidized side chain, for example an ether bridge between the side chain and ring D, is necessary for the cytotoxic activity of cycloartane derivatives. |
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| Keywords: | Cycloartanes Cycloartanone Synthetic derivatives Cytotoxicity |
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