The Canadian medicinal plant Heracleum maximum contains antimycobacterial diynes and furanocoumarins

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• 作者：Taryn O?Neill^a ; John A. Johnson^a ; Duncan Webster^b ; Christopher A. Gray^a ; ^c ; ^cgray@unb.ca
• 关键词：[¦Á]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 ; dime
• 刊名：Journal of Ethnopharmacology
• 出版年：2013
• 出版时间：2 May, 2013
• 年：2013
• 卷：147
• 期：1
• 页码：232-237
• 全文大小：366 K

文摘

Ethnopharmacological relevance

Heracleum 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 methods

A 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.

Results

The 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 ¦ÌM and 167 ¦ÌM and IC₅₀s of 6 ¦ÌM and 27 ¦ÌM 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 ¦ÌM and IC₅₀s of 125, 344, 350, 351, 389 and 406 ¦ÌM.

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.