Essential Oils from Two Apiaceae Species as Potential Agents in Organic Crops Protection.

Chemical composition and herbicidal, antifungal, antibacterial and molluscicidal activities of essential oils from Choukzerk, Eryngium triquetrum, and Alexander, Smyrnium olusatrum, from western Algeria were characterized. Capillary GC-FID and GC/MS were used to investigate chemical composition of both essential oils, and the antifungal, antibacterial, molluscicidal and herbicidal activities were determined by % inhibition. Collective essential oil of E. triquetrum was dominated by falcarinol (74.8%) and octane (5.6%). The collective essential oil of S. olusatrum was dominated by furanoeremophilone (31.5%), furanodiene+curzurene (19.3%) and (E)-ß-caryophyllene (11%). The E. triquetrum oil was tested and a pure falcarinol (99%) showed virtuous herbicidal and antibacterial activities against potato blackleg disease, Pectobacterium atrosepticum, and Gram-negative soil bacterium, Pseudomonas cichorii (85 and 100% inhibition, respectively), and high ecotoxic activity against brine shrimp, Artemia salina, and the freshwater snail, Biomphalaria glabrata, with an IC50 of 0.35 µg/mL and 0.61 µg/mL, respectively. Essential oil of S. olusatrum showed interesting antibacterial and ecotoxic activity and good herbicidal activity against watercress seeds, Lepidium sativum (74% inhibition of photosynthesis, 80% mortality on growth test on model watercress), while the furanoeremophilone isolated from the oil (99% pure) showed moderate herbicidal activity. Both oils showed excellent antifungal activity against Fusarium. Both oils and especially falcarinol demonstrated good potential as new biocontrol agents in organic crop protection.

How are 1,2,3-triazoles accommodated in helical secondary structures?

1,4-Disubstituted-1,2,3-triazole (Tz) is widely used in peptides as a trans-amide bond mimic, despite having hazardous effects on the native peptide activity. The impact of amide bond substitution by Tz on peptide secondary structures is scarcely documented. We performed a Tz scan, by systematically replacing peptide bonds following the Aib residues with Tz on two model peptaibols: alamethicin F50/5 and bergofungin D, which adopt stable α- and 310 helices, respectively. We observed that the Tz insertion, whatever its position in the peptide sequences, abolished their antimicrobial activity. The structural consequences of this insertion were further investigated using CD, NMR and X-ray diffraction. Importantly, five crystal structures that were incorporated with Tz were solved, showing various degrees of alteration of the helical structures, from minor structural perturbation of the helix to partial disorder. Together, these results showed that Tz insertions impair helical secondary structures.

Chemical composition and antifungal activity of plant extracts traditionally used in organic and biodynamic farming.

Five plant extracts traditionally used in organic and biodynamic farming for pest control and antifungal (downy mildew) disease management were selected after a farmer survey and analyzed for their chemical composition in LC-PDA-MS-MS and using adapted analytical method from food chemistry for determination of class of component (e.g., protein, sugar, lipids…). Their antifungal activity against Penicillium expansum, Botrytis cinerea, Botrytis allii, brown rot causing agents (Monilinia laxa and Monilinia fructigena), and grape downy mildew (Plasmopara viticola) was examined in vitro. White willow (Salix alba) and absinthe (Artemisia absinthium) ethanolic extracts were found to be the most effective in particular against Plasmopara viticola, with a total inhibition of spores germination when applied at 1000 mg/L. These extracts also showed a relatively low toxicity during preliminary ecotoxicological assays on Daphnia pulex. Extract from the bark of white willow contained some flavonoids, especially flavanones (eriodyctiol and derivates) and flavanols (catechins and derivates), as major compounds, whereas absinthe extract was rich in O-methylated flavanols and hydroxycinnamic acids. Thujone content in this extract was also determined by external calibration in GC-MS analysis, and its value was 0.004% dry extract.

Essential oils from Algerian species of Mentha as new bio-control agents against phytopathogen strains.

Chemical composition and antifungal activity of essential oils of Algerian Mentha species were studied. Chemical compositions of different Mentha species oils (Mentha rotundifolia, M. spicata, M. pulegium, and M. piperita) were investigated by capillary GC and GC/MS, and their antifungal activities were evaluated by means of paper disc diffusion method and minimum inhibitory concentration (MIC) assays. In total, 98 components from all Mentha species were identified. All oils were rich in monoterpene-oxygenated components. In addition, we reported fumigant antifungal activity of Algerian Mentha essential oils against four fungi: Botrytis cinerea, Penicillium expansum, Monilinia laxa, and M. fructigena. All oils demonstrated very good inhibition especially against B. cinerea, M. laxa, and M. fructigena. Both Monilinia fungi were extremely sensitive to all Algerian Mentha oils, which suggests that Mentha essential oils have the potential to be used as bio-pesticides to protect fruit trees, such as apple and pear trees, and provides an alternative to chemical pesticides.

Enhancing the Antimicrobial Activity of Alamethicin F50/5 by Incorporating N-terminal Hydrophobic Triazole Substituents.

A simple and efficient strategy is proposed to significantly improve the antibacterial activity of peptaibols and other antimicrobial peptides by N-terminal capping with 1,2,3-triazole bearing various hydrophobic substituents on C-4. Such N-terminal insertions on alamethicin F50/5 could enhance its antimicrobial activity on Gram-positive bacteria without modification of its overall three-dimensional structure. Although the native peptide and its analogues shared comparable helical contents, the crystal structure of one of the most active derivative showed a local slight distortion of the N-terminal extremity, which was also observed in solution using NMR spectroscopy. Importantly, fluorescence studies showed that the N-capped derivatives had increased affinity for liposomes, which may indicate they interacted more strongly with the bacterial membrane than alamethicin F50/5.