Isolation and identification of an allelopathic phenylethylamine in rice

Thi, Ho Le; Lin, Chung‐Ho; Smeda, Reid J.; Leigh, Nathan D.; Wycoff, Wei G.; Fritschi, Felix B.

doi:10.1016/j.phytochem.2014.08.019

Cited by 33 publications

(12 citation statements)

References 53 publications

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“…The majority of these studies were related to the metabolism of phenylpropanoids, indole alkaloids and terpenoids (Pauwels et al, 2008;Chen et al, 2013). Although the presence of 2-phenylethylamine (PEA) has been confirmed in several plant species (Smith, 1977;Horbowicz et al, 2011;Le Thi et al, 2014), there is little information regarding biosynthesis and metabolic transformations of this amine.…”

Section: Discussionmentioning

confidence: 99%

“…It is quite likely that PEA is responsible for allelopathic activity of common buckwheat. Le Thi et al (2014) found the allelopathic influence of tyramine cinnamide in barnyard grass, cress and red sprangletop. Recently, the presence of a similar compound, 2-phenylethylamine cinnamide, was confirmed in common buckwheat tissues (Horbowicz et al, 2015).…”

Section: Discussionmentioning

confidence: 99%

“…The presence of 2-phenylethylamine (PEA) has been confirmed in several species of plants (Smith, 1977;Horbowicz et al, 2011;Le Thi et al, 2014). Smith (1977) suggested the role of PEA in constituting the plant resistance towards a wide range of insect pests.…”

Section: Introductionmentioning

confidence: 99%

“…Smith (1977) suggested the role of PEA in constituting the plant resistance towards a wide range of insect pests. Interestingly, Le Thi et al (2014) documented the allelopathic potential of PEA derivative isolated from rice (Oryza sativa L.) against barnyard grass (Echinochloa crusgalli L.), cress (Lepidium sativum L.) and red sprangletop (Leptochloa chinensis L. Nees).…”

Section: Introductionmentioning

confidence: 99%

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Methyl Jasmonate Elicitation Affects Expression of Genes Involved in Biosynthesis and Turnover of 2-Phenylethylamine in Maize Seedlings

Sytykiewicz¹,

Horbowicz²,

Wiczkowski³

et al. 2016

Acta Biologica Cracoviensia S. Botanica

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The objective of the study was to assess the influence of methyl jasmonate (MJ) vapors on accumulation of 2-phenylethylamine (PEA), phenylacetic acid (PAA) and 2-phenylethanol (PE) in leaves and roots of maize (Zea mays L. subsp. mays, saccharata group, cv. Złota Karłowa) seedlings. Furthermore, we analyzed the expression patterns of eight genes (ADH1, ADH2, AO2, CAO, PDC1, PDC2, PTA and LOX, encoding alcohol dehydrogenase 1 and 2, primary amine oxidase, aldehyde oxidase 2, phenylalanine decarboxylase 1 and 2, phenylalanine (histidine) transaminase and lipoxygenase, respectively) involved in biosynthesis and turnover of PEA in maize tissues. In addition, the effect of MJ application on fresh biomass and growth of the tested seedlings was recorded. Oneday MJ exposure increased the fresh weight of aerial parts and roots of Z. mays seedlings, whereas the opposite tendency occurred after 4-day of MJ treatment. One-day application of MJ resulted in an increase in the length of roots and its fluctuations in the aerial parts of maize plants, but extended exposure declined the growth of both parts of the seedlings. Methyl jasmonate elicitation caused various changes in the contents of PEA, PAA and PE in the maize seedlings. MJ treatments led to high upregulation of most genes, with the exception of three genes (i.e., ADH1, ADH2 and AO2) whose expression was downregulated after a 4-day exposure.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Methyl Jasmonate Elicitation Affects Expression of Genes Involved in Biosynthesis and Turnover of 2-Phenylethylamine in Maize Seedlings

Sytykiewicz¹,

Horbowicz²,

Wiczkowski³

et al. 2016

Acta Biologica Cracoviensia S. Botanica

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“…In addition to UV and pathogen induced accumulation of phenylamide phytoalexins in rice leaves, CinTrp and BenTrp were isolated from rice roots without external stimulus [ 57 ]. A recent study also demonstrated that the phenylamide CinTyr isolated from rice acts as an allelochemical that inhibited root and hypocotyl growth of cress, barnyard grass, and red sprangletop [ 58 ]. This result suggests that phenylamide phytoalexins are potential allelochemicals in rice.…”

Section: Phenolic Phytoalexins In Ricementioning

confidence: 99%

Phenolic Phytoalexins in Rice: Biological Functions and Biosynthesis

Cho

Lee

2015

IJMS

100

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Phytoalexins are inducible secondary metabolites possessing antimicrobial activity against phytopathogens. Rice produces a wide array of phytoalexins in response to pathogen attacks and environmental stresses. With few exceptions, most phytoalexins identified in rice are diterpenoid compounds. Until very recently, flavonoid sakuranetin was the only known phenolic phytoalexin in rice. However, recent studies have shown that phenylamides are involved in defense against pathogen attacks in rice. Phenylamides are amine-conjugated phenolic acids that are induced by pathogen infections and abiotic stresses including ultra violet (UV) radiation in rice. Stress-induced phenylamides, such as N-trans-cinnamoyltryptamine, N-p-coumaroylserotonin and N-cinnamoyltyramine, have been reported to possess antimicrobial activities against rice bacterial and fungal pathogens, an indication of their direct inhibitory roles against invading pathogens. This finding suggests that phenylamides act as phytoalexins in rice and belong to phenolic phytoalexins along with sakuranetin. Phenylamides also have been implicated in cell wall reinforcement for disease resistance and allelopathy of rice. Synthesis of phenolic phytoalexins is stimulated by phytopathogen attacks and abiotic challenges including UV radiation. Accumulating evidence has demonstrated that biosynthetic pathways including the shikimate, phenylpropanoid and arylmonoamine pathways are coordinately activated for phenolic phytoalexin synthesis, and related genes are induced by biotic and abiotic stresses in rice.

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Inhibitory effects of N‐trans‐cinnamoyltyramine on growth of invasive weeds and weedy rice

Le,

Nguyen,

Luu

et al. 2024

Plant Enviro Interactions

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N‐trans‐cinnamoyltyramine (NTCT) has been identified from an allelopathic Vietnamese rice accession OM 5930. This study employed bioassays to analyze NTCT's effects on shoot and root growth of multiple test and weed species. NTCT demonstrated potent inhibitory effects on cress, lettuce, canola, palmer amaranth, timothy, barnyardgrass, red sprangletop, and weedy rice, with increasing concentrations leading to substantial reductions in growth in all species. Linear regression analysis of dose response curves revealed ED50 values for NTCT, providing critical insights into the concentration required for 50% growth inhibition in each species. They revealed high sensitivity of the test species cress and lettuce, intermediate sensitivities of barnyardgrass, red sprangletop, timothy, and amaranth, and comparatively lower sensitivity of two weedy rice accessions. The findings underscore NTCT's efficacy in suppressing the growth of a wide range of weeds, including both grasses and broadleaf species. As such, NTCT may hold promise as a tool for sustainable weed management, particularly in addressing herbicide‐resistant weeds in diverse ecological settings.

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Isolation and identification of an allelopathic phenylethylamine in rice

Cited by 33 publications

References 53 publications

Methyl Jasmonate Elicitation Affects Expression of Genes Involved in Biosynthesis and Turnover of 2-Phenylethylamine in Maize Seedlings

Methyl Jasmonate Elicitation Affects Expression of Genes Involved in Biosynthesis and Turnover of 2-Phenylethylamine in Maize Seedlings

Phenolic Phytoalexins in Rice: Biological Functions and Biosynthesis

Inhibitory effects of N‐trans‐cinnamoyltyramine on growth of invasive weeds and weedy rice

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