Antimycobacterial Polyynes of Devil's Club (<i>Oplopanax horridus</i>), a North American Native Medicinal Plant

Kobaisy, Mozaina; Abramowski, Z.; Lermer, Leonard; Saxena, Geeta; Hancock, Robert E. W.; Towers, G. H. N.; Doxsee, Daniel D.; Stokes, Richard W.

doi:10.1021/np970182j

Cited by 128 publications

(138 citation statements)

References 21 publications

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“…The chloroform extract of aerial parts significantly inhibited the growth of resistant Gram-negative bacteria P. aeruginosa (MIC 7.8 μg mL -1 ). Falcarinol, linoleic acid and palmitic acid, the main compounds in the chloroform extract of the aerial parts, exert antimicrobial activity [26,27]. Unsaturated fatty acids such as linoleic acid inhibit bacterial fatty acid synthesis by blocking bacterial enoyl-acyl carrier protein reductase (FabI) which is essential for production of lipidcontaining components such as cell membranes [28].…”

Section: Antimicrobial Activitymentioning

confidence: 99%

Composition, antimicrobial and antioxidant activity of the extracts of Eryngium palmatum Pančić and Vis. (Apiaceae)

et al. 2013

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The chemical composition, antimicrobial and antioxidant activity of Eryngium palmatum, an endemic plant species from the Balkan Peninsula, were investigated. The flavonoids apigenin (9.5±0.3 mg g−1) and apigenin 7-O-glucoside (2.4±0.1 mg g−1) were determined in a methanol extract of aerial parts using HPLC analysis. The methanol extract of roots contained catechin (5.0±0.1 mg g−1), epicatechin (2.9±0.1 mg g−1), chlorogenic acid (1.6±0.0 mg g−1), gallic acid (0.9±0.0 mg g−1) and rosmarinic acid (0.9±0.2 mg g−1). GC-FID and GCMS analysis of a chloroform extract of aerial parts showed that the main volatile constituents were falcarinol, linoleic acid, hexadecanoic acid and methyl linoleate (comprising 32.6%; 24.4%; 19.9; 13.2% of the volatile fraction, respectively), while octanoic acid, tetradecanol and dodecanol dominated in the chloroform extract of the roots (34.9%; 25.8%; 22.2% of the volatile fraction, respectively). Investigation of antimicrobial activity by broth microdilution showed that the methanol and chloroform extracts of aerial parts and roots exerted a significant effect (MIC 3.5–15.6 μg mL−1) against tested Gram-positive and Gram-negative bacteria. The methanol extracts of aerial parts or roots exerted moderate ferric reducing antioxidant power, DPPH radical scavenging activity and hydroxyl radical scavenging activity.

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Section: Antimicrobial Activitymentioning

confidence: 99%

Composition, antimicrobial and antioxidant activity of the extracts of Eryngium palmatum Pančić and Vis. (Apiaceae)

et al. 2013

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“…Falcarindiol (4C) was the most active constituent assayed in Angelica pubescens, a Chinese traditional treatment for arthritis, inhibiting 5-lipoxygenase with an IC 50 of 0.4 μM [297]. The (3S,8S) and (3R,8S)-isomers of 4C were shown to have antimycobacterial activity and to be active against multi-drug resistant strains of S. aureus [298,299]. Acetoxy modifications found in the known Apiaceae acetate 25I and oplopandiol acetate (25H) from Oplopanax horridus increase selectivity towards Mycobacterium spp.. Falcarindiol ethers with furanocoumarins, named japoangelols A-D (25J-M), are novel structures with the potential for enhanced contact toxicity [300]; both polyacetylenes and furanocoumarins in Apiaceae species are known to cause dermatitis.…”

Section: New Natural Productsmentioning

confidence: 99%

Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

296

228

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Polyacetylenic natural products are a substantial class of often unstable compounds containing a unique carbon-carbon triple bond functionality, that are intriguing for their wide variety of biochemical and ecological functions, economic potential, and surprising mode of biosynthesis. Isotopic tracer experiments between 1960 and 1990 demonstrated that the majority of these compounds are derived from fatty acid and polyketide precursors. During the past decade, research into the metabolism of polyacetylenes has swiftly advanced, driven by the cloning of the first genes responsible for polyacetylene biosynthesis in plants, moss, fungi, and actinomycetes, and the initial characterization of the gene products.The current state of knowledge of the biochemistry and molecular genetics of polyacetylenic secondary metabolic pathways will be presented together with an up-to-date survey of new terrestrial and marine natural products, their known biological activities, and a discussion of their likely metabolic origins.

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“…Very few studies on the natural products of this plant have been reported. 4,5 A study has described the presence of antimycobacterial polyynes in a methanol extract. 4 A recent publication reported the presence of some bioactive constituents in the root bark extracts of O. horridus from Alaska.…”

Section: -3mentioning

confidence: 99%

“…4,5 A study has described the presence of antimycobacterial polyynes in a methanol extract. 4 A recent publication reported the presence of some bioactive constituents in the root bark extracts of O. horridus from Alaska. 5 Silica gel chromatography of the extracts resulted in the isolation of certain essential oil constituents, such as (E)-nerolidol, the major component, followed by spathulenol, oplopanone and α-cubebene in lesser amounts.…”

Section: -3mentioning

confidence: 99%

The essential oil composition of devil's club, Oplopanax horridus J. E. Smith Miq.

Garneau

Collin

Gagnon

et al. 2006

Flavour & Fragrance J

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Devil's club has been used in folk medicine by the native tribes of Alaska and British Columbia for centuries for the treatment of colds, fever, burns, stomach troubles and even tuberculosis. 4,5 ExperimentalStems and roots of O. horridus were collected from the same plant stands on 30 December 2002 near Chilliwack, British Columbia, Canada, at about 200 -300 m altitude. A voucher specimen (no. V219467) was deposited at the Herbarium of the University of British Columbia, Vancouver, Canada. Both oils, the one from the stem and the one from the root, were obtained by steam distillation using a low pressure system with an external steam source. The duration of each distillation was approximately 1 h.The essential oils were analysed by GC on a gas chromatograph Hewlett-Packard 5890 (FID detector) equipped with a polar Supelcowax 10 column and a nonpolar DB-5 column (30 m × 0.25 mm × 0.25 µm). Analyses by GC/MS were performed on a Hewlett-Packard mass spectrometer 5972 at 70 eV coupled to an HP 5890 gas chromatograph using a DB-5 and a Supelcowax 10 column (same as above). The temperature program, used for both GC and GC/MS analyses, was 40°C for 2 min, then 2°C/min to 210°C and held constant for 33 min. The identification of the components was done by comparison of their retention indices with standards and by comparison of their mass spectra with literature values 6 and with our data bank.

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Antimycobacterial Polyynes of Devil's Club (Oplopanax horridus), a North American Native Medicinal Plant

Cited by 128 publications

References 21 publications

Composition, antimicrobial and antioxidant activity of the extracts of Eryngium palmatum Pančić and Vis. (Apiaceae)

Composition, antimicrobial and antioxidant activity of the extracts of Eryngium palmatum Pančić and Vis. (Apiaceae)

Biosynthesis and function of polyacetylenes and allied natural products

The essential oil composition of devil's club, Oplopanax horridus J. E. Smith Miq.

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