The Canadian medicinal plant Heracleum maximum contains antimycobacterial diynes and furanocoumarins |
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Authors: | Taryn O?Neill John A Johnson Duncan Webster Christopher A Gray |
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Institution: | 1. Department of Biology, University of New Brunswick, Saint John, New Brunswick, Canada E2L 4L5;2. Division of Infectious Diseases, Department of Medicine, Saint John Regional Hospital, Saint John, New Brunswick, Canada E2L 4L2;3. Department of Chemistry, University of New Brunswick, Saint John, New Brunswick, Canada E2L 4L5 |
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Abstract: | Ethnopharmacological relevanceHeracleum maximum is amongst the most commonly used plants by the indigenous peoples of North America. The First Nations of the eastern Canada use infusions of Heracleum maximum roots for the treatment of respiratory ailments including tuberculosis. Previous investigations of extracts derived from the roots of Heracleum maximum have shown it to possess antimycobacterial activity. Aim of the study: To isolate and identify antimycobacterial constituents from the roots of Heracleum maximum.Materials and methodsA methanolic extract of Heracleum maximum roots was subjected to bioassay guided fractionation using the microplate resazurin assay (MRA) to assess inhibitory activity against Mycobacterium tuberculosis strain H37Ra. The antimycobacterial constituents were identified by NMR, MS and polarimetry.ResultsThe polyacetylene (3R,8S)-falcarindiol and the furanocoumarins bergapten, isobergapten, angelicin, sphondin, pimpinellin, isopimpinellin and 6-isopentenyloxyisobergapten were isolated from the Heracleum maximum root extract. (3R,8S)-Falcarindiol and 6-isopentenyloxyisobergapten exhibited MICs of 24 μM and 167 μM and IC50s of 6 μM and 27 μM against Mycobacterium tuberculosis H37Ra respectively. The remaining furanocoumarins bergapten, isobergapten, angelicin, sphondin, pimpinellin, and isopimpinellin were less active, with MICs of 925, 1850, 2149, 1859, 812 and 1625 μM and IC50s of 125, 344, 350, 351, 389 and 406 μM.Conclusions(3R,8S)-Falcarindiol, bergapten, isobergapten, angelicin, sphondin, pimpinellin, isopimpinellin and 6-isopentenyloxyisobergapten were identified as the principal constituents responsible for the antimycobacterial activity of the roots of Heracleum maximum. This work supports the ethnopharmacological use of Heracleum maximum by Canadian First Nations and Native American communities as a treatment for infectious diseases, specifically tuberculosis. |
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Keywords: | [α]D specific rotation measured at 589 nm and the temperature indicated 1D one dimensional 2D two dimensional ACS American Chemical Society bs broad singlet c concentration in g/100 mL CH2Cl2 dichloromethane d doublet DMSO dimethyl sulfoxide EtOAc ethyl acetate HPLC high performance liquid chromatography HRESIMS high resolution electrospray ionization mass spectrometry IC50 median inhibitory concentration IR infrared LC&ndash MS liquid chromatography&ndash mass spectrometry m multiplet MeOH methanol MIC minimum inhibitory concentration MRA microplate resazurin assay MS mass spectroscopy NaCl sodium chloride nBuOH 1-butanol NMR nuclear magnetic resonance q quartet s singlet SD standard deviation t triplet TLC thin layer chromatography |
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