Antifungal and Herbicidal Effects of Fruit Essential Oils of Four Myrtus communis Genotypes.

The chemical composition of the essential oils isolated by hydrodistillation from the fruits of four selected Myrtus communis L. genotypes from Turkey was characterized by GC-FID and GC/MS analyses. 1,8-Cineole (29.20-31.40%), linalool (15.67-19.13%), α-terpineol (8.40-18.43%), α-pinene (6.04-20.71%), and geranyl acetate (3.98-7.54%) were found to be the major constituents of the fruit essential oils of all M. communis genotypes investigated. The oils were characterized by high amounts of oxygenated monoterpenes, representing 73.02-83.83% of the total oil compositions. The results of the fungal growth inhibition assays showed that the oils inhibited the growth of 19 phytopathogenic fungi. However, their antifungal activity was generally lower than that of the commercial pesticide benomyl. The herbicidal effects of the oils on the seed germination and seedling growth of Amaranthus retroflexus L., Chenopodium album L., Cirsium arvense (L.) Scop., Lactuca serriola L., and Rumex crispus L. were also determined. The oils completely or partly inhibited the seed germinations and seedling growths of the plants. The findings of the present study suggest that the M. communis essential oils might have potential to be used as natural herbicides as well as fungicides.

Auxin and ABA act as central regulators of developmental networks associated with paradormancy in Canada thistle (Cirsium arvense).

Dormancy in underground vegetative buds of Canada thistle, an herbaceous perennial weed, allows escape from current control methods and contributes to its invasive nature. In this study, ~65 % of root sections obtained from greenhouse propagated Canada thistle produced new vegetative shoots by 14 days post-sectioning. RNA samples obtained from sectioned roots incubated 0, 24, 48, and 72 h at 25°C under 16:8 h light-dark conditions were used to construct four MID-tagged cDNA libraries. Analysis of in silico data obtained using Roche 454 GS-FLX pyrosequencing technologies identified molecular networks associated with paradormancy release in underground vegetative buds of Canada thistle. Sequencing of two replicate plates produced ~2.5 million ESTs with an average read length of 362 bases. These ESTs assembled into 67358 unique sequences (21777 contigs and 45581 singlets) and annotation against the Arabidopsis database identified 15232 unigenes. Among the 15232 unigenes, we identified processes enriched with transcripts involved in plant hormone signaling networks. To follow-up on these results, we examined hormone profiles in roots, which identified changes in abscisic acid (ABA) and ABA metabolites, auxins, and cytokinins post-sectioning. Transcriptome and hormone profiling data suggest that interaction between auxin- and ABA-signaling regulate paradormancy maintenance and release in underground adventitious buds of Canada thistle. Our proposed model shows that sectioning-induced changes in polar auxin transport alters ABA metabolism and signaling, which further impacts gibberellic acid signaling involving interactions between ABA and FUSCA3. Here we report that reduced auxin and ABA-signaling, in conjunction with increased cytokinin biosynthesis post-sectioning supports a model where interactions among hormones drives molecular networks leading to cell division, differentiation, and vegetative outgrowth.

[Isolation, identification, and characteristics of the phytotoxin produced by the fungus Alternaria cirsinoxia].

An individual substance (20 mg/l) exhibiting phytotoxic properties, which, on the basis its spectral characteristics, was identified as zinniol, was obtained from the fungus Alternaria cirsinoxia. The nonspecific activity of this phytotoxin, with respect to plants of different families, was demonstrated. The minimum concentration (200 microg/ml) at which zinniol damages creeping thistle leaves and the median inhibition concentration (IC50) for rat embryonic fibroblasts (264 microg/ml) were determined.

Stagonolides G-I and modiolide A, nonenolides produced by Stagonospora cirsii, a potential mycoherbicide for Cirsium arvense.

Stagonospora cirsii Davis, a fungal pathogen isolated from Cirsium arvense (commonly called Canada thistle) and proposed as a potential mycoherbicide of this perennial noxious weed, produces phytotoxic metabolites in liquid and solid cultures. Stagonolide, the main phytotoxic metabolite, and five new related nonenolides, named stagonolides B-F, were isolated from the fungus. When grown on solid culture, nonenolide yields increased. A further four nonenolides were isolated and characterized by spectroscopy. Three were new compounds and named stagonolides G-I, and the fourth was identified as modiolide A, previously isolated from Paraphaeosphaeria sp., a fungus separated from the horse mussel. Leaf disk-puncture assays at 1 mg/mL of stagonolides H-I and modiolide A were phytotoxic to C. arvense. Only stagonolide H inhibited chicory seedling root growth. The most potent toxin, stagonolide H, indicated selectivity when tested on leaves of eight different plants: Canada thistle was most sensitive to the compound.

Production of phytotoxins by Phoma exigua var. exigua, a potential mycoherbicide against perennial thistles.

The potential of the different Phoma exigua var. exigua strains for the biocontrol of the perennial weeds Sonchus arvensis and Cirsium arvense, occurring throughout temperate regions of the world, has been evaluated in previous studies. The majority of the above strains produced ascosonchine, a newly discovered enol tautomer of 4- pyridylpyruvic acid, whereas strains C-177 and S-9, though virulent to weeds, did not produce the above metabolite. In this study, it was demonstrated that the above two strains, grown in liquid and solid cultures, produced p-hydroxybenzaldehyde, cytochalasins B, F, Z2 and Z3, and deoxaphomin. When assayed on the leaves of both C. arvense and S. arvensis, p-hydroxybenzaldehyde was inactive, whereas deoxaphomin demonstrated the highest level of toxicity on leaves of S. arvensis. Cytochalasin Z2 appeared to be the less toxic cytochalasan on both plants according to the lack of the secondary hydroxyl group on C-7. Production of cytochalasins by P. exigua var. exigua strains isolated from C. arvense and S. arvensis is discussed in relation to chemotaxonomy and the biocontrol potential of the fungus.

Phyllostoxin and phyllostin, bioactive metabolites produced by Phyllosticta cirsii, a potential mycoherbicide for Cirsium arvense biocontrol.

Phyllosticta cirsii, a fungal pathogen isolated from diseased Cirsium arvense leaves and evaluated as a biocontrol agent of this noxious perennial weed, produces different phytotoxic metabolites with potential herbicidal activity when grown in liquid cultures. Phyllostictines A-D, four novel oxazatricycloalkenones, were recently isolated from this pathogen and chemically and biologically characterized. Further purification of the same organic extract provided two other metabolites, named phyllostoxin (1) and phyllostin (2), which were characterized by spectroscopic technique (essentially NMR and MS). Phyllostoxin and phyllostin proved to be a new pentasubstituted bicyclo-octatrienyl acetic acid ester and a new pentasubstituted hexahydrobenzodioxine carboxylic acid methyl ester, respectively. When tested on punctured C. arvense leaves, phyllostoxin proved to be highly phytotoxic, causing rapid and large necrosis, whereas phyllostin had no phytotoxicity in this bioassay. This is not surprising, considering the noteworthy structural differences between the two compounds, suggesting the presence of active functional groups in phyllostoxin not present in the other metabolite. These results further support the focused approach of finding novel metabolites with herbicidal properties by looking at the culture extracts of weed fungal pathogens.

Stagonolides B-F, nonenolides produced by Stagonospora cirsii, a potential mycoherbicide of Cirsium arvense.

Stagonospora cirsii, a fungal pathogen isolated from Cirsium arvense and proposed as a potential mycoherbicide of this perennial noxious weed, produces phytotoxic metabolites in liquid and solid cultures. Recently, the main metabolite, stagonolide (1), with interesting phytotoxic properties, was isolated from a liquid culture and characterized as a new nonenolide. In the present work this same fungus, grown in solid culture, exhibited an increased capacity to produce nonenolides. Five new nonenolides, named stagonolides B-F (2-6), were isolated and characterized using spectroscopic methods. When tested by a leaf disk puncture assay at a concentration of 1 mg/mL, these compounds showed no toxicity to C. arvense and Sonchus arvensis, whereas stagonolide (1) was highly toxic. Stagonolide (1) and stagonolide C (3) were weakly toxic to Colpoda steinii, a protozoan, when tested at 0.05 mg/mL, with the other stagonolides nontoxic. A number of structure-activity relationship observations were made.

Nonenolides and cytochalasins with phytotoxic activity against Cirsium arvense and Sonchus arvensis: a structure-activity relationships study.

A structure-activity relationships study was conducted assaying 15 natural analogues and derivatives belonging to two groups of organic compounds, nonenolides and cytochalasins, for their toxicity against the composite perennial weeds Cirsium arvense and Sonchus arvensis occurring through the temperate region of world. The toxic nonenolides (stagonolide, putaminoxin, pinolidoxin) and cytochalasins (deoxaphomin, cytochalasins A, B, F, T, Z2 and Z3) were isolated from phytopathogenic Stagonospora, Phoma and Ascochyta spp. The pinolidoxin (7,8-O,O'-diacetyl- and 7,8-O,O'-isopropylidene-pinolidoxin) and cytochalasins B (21,22-dihydro-, 7-O-acetyl- and 7,20-O,O'-diacetyl-cytochalasin B) derivatives were obtained by chemical modifications of the corresponding toxins. Among the 15 compounds tested, stagonolide and deoxaphomin proved to be the most phytotoxic to C. arvense and S. arvensis leaves, respectively. The tested phytotoxic nonenolides were stronger inhibitors of photosynthesis in C. arvense leaves than cytochalasines A and B. Stagonolide had less effect on membrane permeability in C. arvense leaves than cytochalasin B. Significant changes of light absorption by C. arvense leaves in visible and infrared spectra were caused by stagonolide. The functional groups and the conformational freedom of the ring, appear to be important structural features for the nonenolides toxicity, whereas and the presence of the hydroxy group at C-7, the functional group at C-20 and the conformational freedom of the macrocyclic ring are important for the cytochalasins toxicity.

Herbicidal potential of stagonolide, a new phytotoxic nonenolide from Stagonospora cirsii.

Stagonospora cirsii is a pathogen of Cirsium arvense, causing necrotic lesions on leaves of this noxious weed. The fungus produced toxic metabolites when grown in liquid culture. A new phytotoxin, named stagonolide, was isolated and characterized as (8R,9R)-8-hydroxy-7-oxo-9-propyl-5-nonen-9-olide by spectroscopic methods. Stagonolide was shown to be a nonhost-specific but selective phytotoxin. Leaves of C. arvense were most sensitive and leaves of tomato and pepper (both Solanaceae) were less sensitive to stagonolide, which was assayed at 5 x 10(-3) M, than other plants. Stagonolide assayed at 5 x 10(-6) M was demonstrated to be a strong inhibitor of root growth in seedlings of C. arvense and some other Asteraceae species. Seedlings growth in wheat and radish was much less affected by the toxin, and seedlings of cucumber were insensitive to it.

The macrocidins: novel cyclic tetramic acids with herbicidal activity produced by Phoma macrostoma.

Field isolates of Phoma macrostoma were obtained from diseased Canada thistle growing in several geographically diverse regions. Bleaching and chlorotic symptoms were present on the infected plants. The isolates grown in liquid culture were found to produce phytotoxic metabolites which also caused bleaching when applied foliarly to several broadleaf species. Bioassay-directed isolation led to the discovery of macrocidins A and B, the first representatives of a new family of cyclic tetramic acids. This new chemotype may offer significant potential as a template for herbicide design.