Synthesis and plant growth inhibitory activity of <i>N-trans</i>-cinnamoyltyramine: its possible inhibition mechanisms and biosynthesis pathway

Thi, Ho Le; Zhou, Haiying; Lin, Chung‐Ho; Liu, Sheng-Jun; Berezin, Mikhail Y.; Smeda, Reid J.; Fritschi, Felix B.

doi:10.1080/17429145.2016.1278050

Cited by 8 publications

(6 citation statements)

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“…A large number of studies have shown that phenylpropanoid amides have significant inhibitory effects on plant growth ( Vishnoi et al., 2009 ; Thi et al., 2014 ; Thi et al., 2017 ), and we speculated that these compounds may be the potential phytotoxic substances for S. rostratum. In addition, A. thaliana is an important model plant for evaluating phytotoxic effects, which has been reported in many literatures ( Liu et al., 2013 ; Chen et al., 2016 ; Li et al., 2019 ).…”

Section: Resultsmentioning

confidence: 97%

“…Among them, phenylpropanoid amides compounds are biosynthesized from cinnamic acid and phenylethylamine derivatives, which has complex chemical structures and diverse biological activities ( Sun et al., 2015 ; Hao et al., 2022 ). A large number of studies have shown that phenylpropanoid amides have significant inhibitory effects on plant growth ( Vishnoi et al., 2009 ; Thi et al., 2014 ; Thi et al., 2017 ), and we speculated that these compounds may be the potential phytotoxic substances for S. rostratum.…”

Section: Introductionmentioning

confidence: 97%

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Phenylpropanoid amides from Solanum rostratum and their phytotoxic activities against Arabidopsis thaliana

Liu

Zhang

et al. 2023

Front. Plant Sci.

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IntroductionSolanum rostratum, an annual malignant weed, has seriously damaged the ecological environment and biodiversity of invasion area. This alien plant gains a competitive advantage by producing some new phytotoxic substances to inhibit the growth of native plants, thus achieving successful invasion. However, the chemical structures, inhibitory functions and action mechanisms of phytotoxic substances of S. rostratum remain unclear.MethodsIn this study, to clarify the chemical structures of phytotoxic substances from S. rostratum, we isolated phenylpropanoid amides from the plant. Their structures were identified by comprehensive HR-ESIMS, NMR and ECD data. And the inhibitory functions of isolated phenylpropanoid amides on one model plant (Arabidopsis thaliana) were also investigated. In addition, the action mechanisms of active phenylpropanoid amides were revealed by antioxidant-related enzymes [Catalase (CAT), Peroxidase (POD), Superoxide dismutase (SOD)] activities and corresponding molecular docking analyses.Results and DiscussionPhytochemical research on the whole plant of S. rostratum led to the isolation and identification of four new phenylpropanoid amides (1−4), together with two known analogues (5−6). All the compounds showed phytotoxic effects with varying levels on the seed germination and root elongation of one model plant (Arabidopsis thaliana), especially compound 2 and 4. Likewise, compounds 2 and 4 displayed potent inhibitory effects on antioxidant-related enzyme (POD). In addition, compounds 2 and 4 formed common conventional hydrogen bonds with residues Ala34 and Ser35 in POD revealed by molecular docking analyses. These findings not only helped to reveal the invasion mechanism of S. rostratum from the perspective of “novel weapons hypothesis”, but also opened up new ways for the exploitation and utilization of S. rostratum.

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Section: Resultsmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 97%

Phenylpropanoid amides from Solanum rostratum and their phytotoxic activities against Arabidopsis thaliana

Liu

Zhang

et al. 2023

Front. Plant Sci.

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“…This is consistent with our earlier reports [ 43 , 44 , 45 ], that some natural and synthetic substances exhibited more harmful effect on roots of Chinese amaranth and barnyard grass than shoots. Comparably, Thi et al [ 46 ] reported that root growth of barnyard grass was more sensitive to N - trans -cinnamoyltyramine herbicide than shoot growth. This was attributed to different permeabilities of active chemicals into roots and shoots, different enzyme profiles, plant organs, and growth stages.…”

Section: Discussionmentioning

confidence: 99%

Enantioselective and Synergistic Herbicidal Activities of Common Amino Acids Against Amaranthus tricolor and Echinochloa crus-galli

2021

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Amino acids have a wide range of biological activities, which usually rely on the stereoisomer presented. In this study, glycine and 21 common α-amino acids were investigated for their herbicidal property against Chinese amaranth (Amaranthus tricolor L.) and barnyard grass (Echinochloa crus-galli (L.) Beauv.). Both d- and l-isomers, as well as a racemic mixture, were tested and found that most compounds barely inhibited germination but moderately suppressed seedling growth. Various ratios of d:l-mixture were studied and synergy between enantiomers was found. For Chinese amaranth, the most toxic d:l-mixtures were at 3:7 (for glutamine), 8:2 (for methionine), and 5:5 (for tryptophan). For barnyard grass, rac-glutamine was more toxic than the pure forms; however, d-tryptophan exhibited greater activity than racemate and l-isomer, indicating the sign of enantioselective toxicity. The mode of action was unclear, but d-tryptophan caused bleaching of leaves, indicating pigment synthesis of the grass was inhibited. The results highlighted the enantioselective and synergistic toxicity of some amino acids, which relied upon plant species, chemical structures, and concentrations. Overall, our finding clarifies the effect of stereoisomers, and provides a chemical clue of amino acid herbicides, which may be useful in the development of herbicides from natural substances.

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“…As reported in Scheme 3 , cinnamic acid was converted by COA ligase into the corresponding activate form [ 10 ]. The final step provides the conjugation of cinnamoylCoA and tyramine catalyzed by the tyramine n -hydroxycinnamoyl transferase (THT): this enzyme is not specific to cinnamoylCoA and tyramine, but also catalyzes the conjugation of tyramine with the other CoA-activated cinnamic acids cited above [ 11 , 12 ].…”

Section: Biosynthesis Of N - Trans -Cinnamoyltyraminementioning

confidence: 99%

Natural Bioactive Cinnamoyltyramine Alkylamides and Co-Metabolites

Evidente

Masi

2021

Biomolecules

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Natural products are a vital source for agriculture, medicine, cosmetic and other fields. Among them alkylamides are a broad and expanding group found in at least 33 plant families. Frequently, they possess a simple carbon skeleton architecture but show broad structural variability and important properties such as immunomodulatory, antimicrobial, antiviral, larvicidal, insecticidal and antioxidant properties, amongst others. Despite to these several and promising biological activities, up to today, only two reviews have been published on natural alkylamides. One focuses on their potential pharmacology application and their distribution in the plant kingdom and the other one on the bioactive alkylamides specifically found in Annona spp. The present review is focused on the plant bioactive cinnamoyltyramine alkylamides, which are subject of several works reported in the literature. Furthermore, the co-metabolites isolated from the same natural sources and their biological activities are also reported.

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Synthesis and plant growth inhibitory activity of N-trans-cinnamoyltyramine: its possible inhibition mechanisms and biosynthesis pathway

Cited by 8 publications

References 48 publications

Phenylpropanoid amides from Solanum rostratum and their phytotoxic activities against Arabidopsis thaliana

Phenylpropanoid amides from Solanum rostratum and their phytotoxic activities against Arabidopsis thaliana

Enantioselective and Synergistic Herbicidal Activities of Common Amino Acids Against Amaranthus tricolor and Echinochloa crus-galli

Natural Bioactive Cinnamoyltyramine Alkylamides and Co-Metabolites

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