Min An

Allelochemicals in Wheat (Triticum aestivum L.): Variation of Phenolic Acids in Shoot Tissues

Seven known phenolic acids implicated in wheat allelopathy were analyzed in a worldwide collection of 58 wheat accessions by gas chromatography and tandem mass spectrometry (GC-MS-MS). Chemical analysis showed that accessions differed significantly in the production of p-hydroxybenzoic, vanillic, syringic, trans-p-coumaric, cis-p-coumaric, trans-ferulic, and cis-ferulic acids in the shoots of 17-day-old wheat seedlings. The concentrations of p-hydroxybenzoic, vanillic, cis-p-coumaric, and cis-ferulic acids were normally distributed in the 58 accessions. A binormal distribution was found for syringic and trans-ferulic acids and a skewed normal distribution for trans-p-coumaric acid. The concentration of each compound also varied with phenolic acids. The relative abundance of each phenolic acid was ordered decreasingly as trans-ferulic, vanillic, trans-p-coumaric, p-hydroxybenzoic, syringic, cis-ferulic, and cis-p-coumaric acids. The concentration of total identified phenolic acids varied from 93.2 to 453.8 mg/kg in the shoots of 58 accessions. The content of each phenolic acid or group was highly associated with others in the shoots of wheat seedlings. Wheat accessions with high levels of total identified phenolic acids in the shoots are generally strongly allelopathic to the growth of annual ryegrass.

Distribution and exudation of allelochemicals in wheat Triticum aestivum.

Wheat allelopathy has potential for weed suppression. Allelochemicals were identified in wheat seedlings, and they were exuded from seedlings into agar growth medium. p-Hydroxybenzoic, trans-p-coumaric, cis-p-coumaric, syringic, vanillic, trans-ferulic, and cis-ferulic acids and 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) were identified in both the shoots and roots of 17-day-old wheat seedlings and their associated agar growth medium. Wheat accessions with previously identified allelopathic activity tended to contain higher levels of allelochemicals than poorly allelopathic ones. The allelopathic compounds present in the shoots generally also were identified in the roots and in the agar medium. Allelochemicals were distributed differentially in wheat, with roots normally containing higher levels of allelochemicals than the shoots. When the eight allelochemicals were grouped into benzoic acid and cinnamic acid derivatives, DIMBOA, total coumaric, and total ferulic acids, the amount of each group of allelochemicals was correlated between the roots and the shoots. Most of the allelochemicals identified in the shoots and roots could be exuded by the living roots of wheat seedling into the agar growth medium. However, the amounts of allelochemicals in the agar growth medium were not proportional to those in the roots. Results suggest that wheat plants may retain allelochemicals once synthesized. The presence of allelochemicals in the agar growth medium demonstrated that wheat seedlings were able to synthesize and to exude phytotoxic compounds through their root system that could inhibit the root growth of annual ryegrass.

Identification and Quantitation of Compounds in a Series of Allelopathic and Non-Allelopathic Rice Root Exudates

An investigation of the chemical basis for rice allelopathy to the rice weed arrowhead (Sagittaria montevidensis) was undertaken using GC/MS and GC/MS/MS techniques. Twenty-five compounds were isolated and identified from the root exudates of both allelopathic and non-allelopathic rice varieties. Phenolics, phenylalkanoic acids, and indoles were among the chemical classes identified. Two indoles previously unreported in rice were detected in the exudates, 5-hydroxy-2-indolecarboxylic acid and 5-hydroxyindole-3-acetic acid. Several other compounds identified in this study have not previously been reported in rice root exudates, namely mercaptoacetic acid, 4-hydroxyphenylacetic acid, and 4-vinylphenol. The levels of 15 compounds present in the exudates were quantified using GC/MS/MS. Six of the seven most abundant compounds were phenolic acids. Significant differences exist between the allelopathic and non-allelopathic cultivars in their production of three of these six compounds. Greater amounts of trans-ferulic acid, p-hydroxybenzoic acid, and caffeic acid were detected in the exudates of allelopathic cultivars. The seventh compound, abietic acid, was significantly higher in the non-allelopathic cultivars.

Mathematical modeling of allelopathy: Biological response to allelochemicals and its interpretation

Allelochemicals are assumed to possess specific biological properties and responses of an organism are external expressions of such properties. Based on this assumption, a mathematical model has been constructed to interpret the characteristic responses of an organism to allelochemicals. Several sets of experimental data have been compared with the model predictions; good agreement between the model and data is observed.

Allelochemicals in Wheat (Triticum aestivum L.): Production and Exudation of 2,4-Dihydroxy-7-Methoxy-1,4-Benzoxazin-3-One

An analytical technique employing gas chromatography and tandem mass spectrometry (GC/MS/MS) was employed to systematically screen fifty-eight wheat accessions for their differential production of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) from three consecutive sources, i.e., the shoots, roots, and in the associated agar growth medium (collected as root exudates) of 17-day-old wheat seedlings. DIMBOA content differed significantly in the shoots, roots, or in the agar growth medium between accessions. DIMBOA accumulated differentially within the plant, with roots containing more DIMBOA than the shoots. Only 19% of accessions were able to exude DIMBOA from living roots into their growth medium, indicating the exudation of DIMBOA is accession-specific. DIMBOA level in root tissues is expected to be high when a high level of DIMBOA content is detected in the shoots. Wheat seedlings did not release detectable amounts of DIMBOA when the DIMBOA level was low in the root tissues. The valuable genetic material with high levels of DIMBOA in the shoots or roots identified in the present research could be used to breed for wheat cultivars with elevated allelopathic activity.

Autotoxicity of wheat (Triticum aestivum L.) as determined by laboratory bioassays

AbstractsWheat varietal autotoxicity and varietal allelopathy were assessed based on plant extract and root exudate bioassays under laboratory conditions. Aqueous extract of wheat differed in varietal autotoxicity and varietal allelopathy, inhibiting wheat germination by 2–21%, radicle growth by 15–30%, and coleoptile growth by 5–20%, depending on the combination of the receiver and donor. Extracts of cv Triller or cv Currawong were more allelopathic to other wheat varieties than cv Batavia and cv Federation. Triller extract was more autotoxic than Federation. Assessment of root exudates by the equal-compartment-agar-method further identified the significant differences in varietal autotoxicity and varietal allelopathy of root exudates between wheat varieties, with root exudates of Triller or Batavia showing stronger autotoxic or allelopathic effects than Currawong or Federation. The varietal autotoxicity and allelopathy of root exudates also showed a characteristic radial inhibitory pattern in the agar growth medium. These results suggest that careful selection of suitable wheat varieties is necessary in a continuous cropping system in order to minimize the negative impacts of varietal allelopathy and varietal autotoxicity. Factors affecting autotoxicity in the field and strategies in autotoxicity management are discussed.

Correlation between phytotoxicity on annual ryegrass (Lolium rigidum) and production dynamics of allelochemicals within root exudates of an allelopathic wheat

An improved allelopathic correlation between phytotoxicity measured in root growth bioassay upon annual ryegrass (Lolium rigidum Gaud.) and the concentrations of a selection of dynamically produced allelochemicals quantified in the root exudates of cv. Khapli wheat (Triticum turgidum ssp. durum (Desf.) Husn.) monitored during the first 15 days of wheat seedling growth in a sterile, agar–water medium, has been established. Changes over the 15-day growth period in the quantities of five exuded benzoxazinones and seven phenolic acids were measured simultaneously using GC/MS/MS. Substantiating pure compound dose–response measurements were conducted over a range of concentrations for the putative allelochemicals within the wheat exudates. One synergism-based proposal using the monitored compounds to explain the observed low-exudate-concentration phytotoxicity was explored, but was found to be experimentally inadequate.

On-site field sampling and analysis of fragrance from living lavender (Lavandula angustifolia L.) flowers by solid-phase microextraction coupled to gas chromatography and ion-trap mass spectrometry.

Solid-phase microextraction coupled to gas chromatography and mass spectrometry has been applied as a simple alternative method for the analysis of essential oil directly from lavender intact flowering spikes and genuine oils. All recognised major oil constituents were detected by this procedure, with results comparable to those given by a conventional method (organic solvent extraction). Distinctive chromatographic profiles were found for various species.

Simultaneous determination of phenolic acids and 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one in wheat (Triticum aestivum L.) by gas chromatography-tandem mass spectrometry.

A procedure using gas chromatography and tandem mass spectrometry (GC-MS-MS) has been developed for the identification and quantification of some allelochemicals in wheat (Triticum aestivum L.). The quantities of allelochemicals in wheat shoots ranged from 2.9 to 110 mg per kilogram of dry shoot residues. Compared with gas chromatography-mass spectrometry (GC-MS), the GC-MS-MS technique significantly increased instrument selectivity and sensitivity, thereby providing more reliable quantitation results in the determination of the phytotoxic compounds examined during this allelopathy research.

Mathematical Modeling of Allelopathy. III. A Model for Curve-Fitting Allelochemical Dose Responses.

Bioassay techniques are often used to study the effects of allelochemicals on plant processes, and it is generally observed that the processes are stimulated at low allelochemical concentrations and inhibited as the concentrations increase. A simple empirical model is presented to analyze this type of response. The stimulation-inhibition properties of allelochemical-dose responses can be described by the parameters in the model. The indices, p% reductions, are calculated to assess the allelochemical effects. The model is compared with experimental data for the response of lettuce seedling growth to Centaurepensin, the olfactory response of weevil larvae to α-terpineol, and the responses of annual ryegrass (Lolium multiflorum Lam.), creeping red fescue (Festuca rubra L., cv. Ensylva), Kentucky bluegrass (Poa pratensis L., cv. Kenblue), perennial ryegrass (L. perenne L., cv. Manhattan), and Rebel tall fescue (F. arundinacea Schreb) seedling growth to leachates of Rebel and Kentucky 31 tall fescue. The results show that the model gives a good description to observations and can be used to fit a wide range of dose responses. Assessments of the effects of leachates of Rebel and Kentucky 31 tall fescue clearly differentiate the properties of the allelopathic sources and the relative sensitivities of indicators such as the length of root and leaf.