Anti-inflammatory,antimicrobial and acetylcholinesterase inhibitory activities of friedelanes from Maytenus robusta branches and isolation of further triterpenoids |
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| Affiliation: | 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. 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 Chemistry, Faculty of Science, Ege University, 35100 Bornova, Izmir, Turkey;2. Department of Chemistry, Faculty of Science, Çankırı Karatekin University, Çankırı, Turkey;1. Faculty of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650050, China;2. College of Pharmaceutical Science, Yunnan University of Traditional Chinese Medicine, Kunming 650050, China;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 |
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| Abstract: | The new pentacyclic triterpenoids friedel-1-en-3,16-dione (1), 1α,29-dihydroxyfriedelan-3-one (2) and 16β,28,29-trihydroxyfriedelan-3-one (3) were isolated from Maytenus robusta branches in addition to the known, but new for this species, triterpenoid 12α,29-dihydroxyfriedelan-3-one (4). The structures and stereochemistry of the novel triterpenoids were established by IR, 1D/2D NMR and HR-APCIMS spectral data. In addition, the biological activity of compound 2 and the previously isolated friedelanes 5–8 (friedelan-3,16-dione, 29-hydroxyfriedelan-3-one, 29-hydroxyfriedelan-3,16-dione and 16β,29-dihydroxyfriedelan-3-one) was investigated. Compounds 2 and 8 were tested for their acetylcholinesterase properties and antimicrobial activity against the bacteria Staphylococcus aureus, Pseudomonas aeruginosa, Listeria monocytogenes, Citrobacter freundii, and the fungus Candida albicans. Compound 2 was the most active compound for both assays, with values of 32.3% acetylcholinesterase inhibition, 42% activity against the fungus Candida albicans and 34% against the bacterium Pseudomonas aeruginosa. Compounds 5–8 were assayed for their antiedematogenic activity using the carrageenan-induced paw edema assay. At maximum inflammation after three hours, compounds 6 and 8 showed 42% and 57% activity, respectively. After four hours, compounds 5 and 7 showed activity of 71% and 75% compared to 79% of the control indomethacin. |
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| Keywords: | Friedel-1-en-3,16-dione 1α,29-dihydroxyfriedelan-3-one 16β,28,29-trihydroxyfriedelan-3-one Anti-inflammatory activity |
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