Sesquiterpene lactones from the leaves of Hedyosmum brasiliense (Chloranthaceae)

• Published in: Phytochemistry (Oxford) 2013-03, Vol.87, p.126-132
• Main Authors: Amoah, Solomon K.S., de Oliveira, Fabio L., da Cruz, Ana Caroline H., de Souza, Nicole M., Campos, Francinete R., Barison, Andersson, Biavatti, Maique W.
• Format: Article
• Language: English
• Subjects: chemical composition; Chloranthaceae; Elemenolides; Guaianolides; Hedyosmum; Hedyosmum brasiliense; Lactones - chemistry; Lactones - pharmacology; leaves; Lindenanolides; Magnetic Resonance Spectroscopy; Magnoliopsida - chemistry; Mycobacterium tuberculosis; Mycobacterium tuberculosis - drug effects; nuclear magnetic resonance spectroscopy; Plant Leaves - chemistry; scopoletin; Sesquiterpenes - chemistry; Sesquiterpenes - pharmacology; shrubs; vanillic acid; vanillin
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2012.11.018

Sesquiterpene lactones were isolated from Hedyosmum brasiliense and tested against Mycobacterium tuberculosis. All isolated compounds were identified based on extensive analysis of 1D and 2D NMR and MS data. [Display omitted] ► Sesquiterpene lactone structures were established from 1D and 2D NMR and MS data. ► The relative configurations of compounds were deduced on basis of key 1D NOE NMR experiments. ► EXSY NMR showed 7 as a compound with two isomers. ► No in vitro anti-mycobacterial activity was observed for the test lactones in the assay performed. 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 1–30μM.