Sesquiterpene lactones from the leaves of Hedyosmum brasiliense (Chloranthaceae) |
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| Affiliation: | 1. CIF, CCS, Universidade Federal de Santa Catarina, Florianópolis, SC, Brazil;2. Cristalografia, Departamento de Química, UNICAMP, Campinas, SP, Brazil;3. LIDI, CCB, Universidade Federal de Santa Catarina, Florianópolis, SC, Brazil;4. Departamento de Química, Universidade Federal do Paraná, Curitiba, PR, Brazil;1. Tobacco Research Institute of Chinese Academy of Agricultural Sciences, Qingdao 266101, China;2. Hubei University of Chinese Medicine, Wuhan 430070, China;3. Graduate School of Chinese Academy of Agricultural Sciences, Beijing 100081, China;1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;2. Yunnan University of Traditional Chinese Medicine, Kunming 650500, China;3. College of Plant Protection, Northwest A&F University, Yangling 712100, China;1. School of Pharmacy, Fudan University, Shanghai 201203, People’s Republic of China;2. School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240, People’s Republic of China;3. Key Laboratory of Chemical Biology and Molecular Engineering of Education Ministry, Institute of Molecular Science, Shanxi University, Taiyuan 030006, People’s Republic of China;1. Programa de Pós-Graduação em Farmácia, Universidade Federal de Santa Catarina – UFSC, Florianópolis, SC, Brazil;2. Laboratory of Pharmacognosy & Natural Products Chemistry, Faculty of Pharmacy, University of Athens, Panepistimioupoli, Zografou, 15771 Athens, Greece;3. Laboratório de Biologia Molecular e Micobactérias, Universidade Federal de Santa Catarina, Florianópolis, SC, Brazil;4. NMR Center, Universidade Federal do Paraná–UFPR, Curitiba, PR, Brazil |
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| Abstract: | Hedyosmum brasiliense Miq. is an endemic aromatic arborescent shrub that is the only representative of the Chloranthaceae in Brazil. There have been few studies seeking to determine its chemical constituents and/or pharmacological effects. This work describes the isolation and identification of sesquiterpene lactones from the leaves, including guaianolides, elemanolides and a lindenanolide. These were tested against Mycobacterium tuberculosis, together with podoandin, onoseriolide and some other common phenolics. The structures of the isolated compounds were determined based on extensive analysis of 1D and 2D NMR spectroscopic and MS data, as well as comparison with published data. The compounds found were the guaianolides, 1,2-epoxy-10α-hydroxy-podoandin and 1-hydroxy-10,15-methylenepodoandin, the elemenolide 15-acetoxy-isogermafurenolide and the lindenanolide 8α/β,9α-hydroxy-onoseriolide, along with the previously isolated guaianolide podoandin, the lindenanolide onoseriolide and the elemenolide 15-hydroxy-isogermafurenolide. The phenolic compounds isolated were scopoletin, vanillin, vanillic acid, protocatechuic aldehyde and ethyl caffeate. The isolated sesquiterpene lactones did not show anti-mycobacterial activity against isoniazid-sensitive M. tuberculosis cultures at concentrations of 1–30 μM. |
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