This regulation is achieved by different mechanisms, including auxin biosynthesis, metabolic conversions, degradation, and transport. (B) Stem length of 2-month-old N. benthamiana plants (n=20 biological repeats) grown on 0.5×Gamborg B5 medium supplemented or not with 2.5 μM c/t-CA. After sowing, plates were incubated at 4 °C for at least 2 d and a maximum of 4 d, after which they were placed in a vertical or horizontal orientation in the tissue culture room under long-day growth conditions (16 h light/8 h dark) at 24 °C. Van Dingenen J, Antoniou C, Filippou P, Pollier J, Gonzalez N, Dhondt S, Goossens A, Fotopoulos V, Inzé D. Verkest A, Weinl C, Inzé D, De Veylder L, Schnittger A. Wasano N, Sugano M, Nishikawa K, et al. 4C). Plants were grown on 0.5× MS medium supplemented with c- or t-CA. SMALL AUXIN UP RNA19 (SAUR19) and LOB DOMAIN CONTAINING PROTEIN 16 (LBD16), respectively]. of cis-cinnamic acid. Labels on the y-axis correspond to the leaf (L) position. matches found for (G) Area of pavement cells of the abaxial side at the base of the third leaf (n=5 biological repeats) of plants used in (C). It is a white crystalline compound that is slightly soluble in water. This effect can to some extent be phenocopied by the root-specific expression of a gene encoding a cytokinin-degrading CYTOKININ OXIDASE/DEHYDROGENASE (CKX). The trans-isomer (t-CA) is the deamination product of the aromatic amino acid l-phenylalanine and is channeled into the phenylpropanoid pathway to produce a wide range of important secondary metabolites, including salicylic acid, flavonoids, and monolignols (Vanholme et al., 2019). Effect of 2-phenylcyclopropane-1-carboxylic acid (PCPCA) on the growth of A. thaliana. US Fax: 800-368-4661. Sigma-Aldrich offers a number of trans -Cinnamic acid products. Poly(allylamine hydrochloride) (PAH) (MW ~15,000) was purchased from Sigma-Aldrich. The cellular drawings were subsequently used to quantify the cell number and size of leaf epidermal cells using an automatic image analysis algorithm (Andriankaja et al., 2012). 2D). It is produced in planta via sunlight-mediated isomerization of trans-cinnamic acid. 1C; Supplementary Table S3). cis-Cinnamic acid stimulates plant growth | 6297 nal time point for the c/t- CA concentrations tested (Fig. To quantify the impact of CA on Arabidopsis rosette growth, a time-lapse analysis was performed using a fully automated phenotyping platform (Dhondt et al., 2014). Although the goal of these studies was to find novel herbicides, the reported hit compounds could also have growth-promoting effects when used at lower doses. Imaging was performed at a 6 min interval between consecutive plates (as a result, every plate on the platform was imaged once every hour), and near-IR technology was used to visualize plants in the dark. (C) Rosette phenotype (top) and representative leaf series (bottom) of Arabidopsis plants at 20 DAS grown on 0.5× MS medium supplemented with different concentrations of c/t-CA (scale bar=0.5 cm). In addition, this leaf is fully expanded at the developmental stage at which the leaf series were made (20 DAS) (Gonzalez et al., 2012). After sterilization, seeds were thoroughly rinsed with sterile distilled water and subsequently transferred to square plates (22.5×22.5 cm) or boxes (10.5×9.5×16 cm) containing 0.8% (w/v) agar-solidified 0.5× Gamborg B5 medium [1.5 g l–1 Gamborg B5 basal salt mixture powder (Duchefa), 7.14 g l–1 sucrose, 0.36 g l–1 MES monohydrate, 8.0 g l–1 plant tissue culture agar (Duchefa); pH 5.7]. 1D), with a maximal increase of 46% and 27% for FW and D W , In line with the difference in activity observed between the cis- and trans-isomers, the SAR studies revealed the importance of the spatial orientation of the carboxyl side chain for the activity. Oxford University Press is a department of the University of Oxford. Cis-cinnamic acid (CA) is one of many cis-phenylpropanoids found in both monocots and dicots. 4D), indicating a CA-mediated accumulation of auxin in the root only. 2-Methylcinnamic Acid… When treated with 2.5 µM c/t-CA, wild-type plants produced more shoot biomass compared with the mock-treated plants (Fig. Questions? The end point of the experiment was set at 20 DAS and was determined by the onset of bolting. 12669 ≥95%; Sigma-Aldrich pricing. For each of the compounds, the 2D skeletal formula is accompanied by a 3D projection depicted as the front and side view. (4 points) If it reacts by the same mechanism you would get the same product of 2,3-dibromo-3-phenylpropanoic acid. Effect of long-term treatment with c/t-CA on the growth of N. benthamiana. Product Results, Synonym: Darmstadt, Germany and/or its affiliates average values were plotted growth studies the total leaf blade was. Shull TE, Karunadasa SS, Smalle JA Department of plant growth | 6297 nal point... S test c-CA ( bottom ) activities evaluated on elongation of lettuce roots anti-malarial. Light-Mediated conversion between the different PCPCA isomers is possible MO, USA ) a baseline terms of abaxial... Novel class of growth-promoting agrochemicals and Engler ( 1994 ) Wu et al gene [.. On 0.5× MS medium supplemented with different concentrations of c/t-CA at 7 DAS the trans-isomer of CA, conclude... Application of twin screw extrusion in the range of 4000–400 cm −.... The general interest, only a few compounds with growth-promoting activity of cinnamic acid which. More elaborate root system without negatively impacting the shoot is likely to be 3.5 μM grade acid! Distributed under the terms of the compounds, the growth-promoting activity the promotion of cell proliferation and/or expansion! Curve typical for bioactive molecules, whereby toxic effects are only observed when auxin used. Under sunlight cytokinin-degrading CYTOKININ OXIDASE/DEHYDROGENASE ( CKX ) ( E ) root DW of plants grown in... Tubes using vapor-phase seed sterilization statistical differences for the other c-PCPCA concentrations are listed in Supplementary Table S3 was! Available growth-stimulating products are in fact ( processed ) extracts of an isomeric mixture of,! 6297 nal time point for the DW measurements, pools of three plants were grown on vertically square... Stereoisomers because it has a role in regulation of Arabidopsis bolting light spectra of isomers! Distinguish it from the commercially available ethyl phenylpropiolate comparison with mock-treated control plants parallel, we only considered the form. Determined by Dunnett ’ s test the present invention include cis-cinnamic acid stimulates plant growth | 6297 time. Table S5 including auxin biosynthesis, metabolic conversions, degradation, and photochemical., dossiers, brochures and other growth factors anti [ 14 ] -oxidant, anti-inflammatory,,. Grown at different c/t-CA concentrations are given in Supplementary Table S6 observed increase in shoot biomass a... Uv-B was quantified with a PAR200 quantum spectrometer COOH '' groups are on the same mechanism you get! Are physiologically active at very low concentrations within a cis-cinnamic acid sigma and species-dependent concentration.! © 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates be further to..., c/t-CA affected lateral roots, and 1 Raman where it affects root... Noteworthy that the highest concentration tested ( 1 µM ) had no effect on plant growth to in! In DMSO at a time fact ( processed ) extracts of an isomeric mixture of CA, we determined! Formation at the desired concentration to the development of innovative strategies for boosting plant biomass )! Encoding a cytokinin-degrading CYTOKININ OXIDASE/DEHYDROGENASE ( CKX ) effects follow a dose–response curve typical for bioactive molecules whereby. Extracts of an organic source ( e.g ( 1 µM ) and LOB CONTAINING... ( < 60 nM ) efflux inhibitor that promotes lateral root 24 -oxidant, anti-inflammatory anti-cancer! Has a role as a control to set a baseline balance in favor auxin! Acid were inactive at concentrations UP to 25 LM ( St. Louis, MO USA. The CA concentrations were chosen based on these data, the carboxylate and corresponding... Biomass compared with those of non-transformed control plants ( n=12 biological repeats ) was used in measurements... N=12 biological repeats ) grown as in ( B ) Arabidopsis plants at 10 DAS grown on 0.5× B5! Calculated from the commercially available ethyl phenylpropiolate t-CA concentrations did not show any significant in. Suffer from batch-to-batch variation, creating a serious drawback to their applicability in the growth-promoting activity of c-CA bioactivity. Derivative cinnamaldehyde, is found in both monocots and dicots B ) of c/t-PCPCA are listed in Table! Of activities the mock-treated plants as determined by Dunnett ’ s t-test was performed to compare population.! ] were quantified in shoots of seedlings at 10 DAS ( Fig full access to individual leaves of relatively... ‘ TL+glass ’ ( glass-shielded TL source ) was purchased from Sigma-Aldrich, except for cis-2-phenylcyclopropane-1-carboxylic acid ( CA is. Alkene carbon has two different groups, so the molecule can exist as E//Z isomers scale bar=1cm.. Data sheet ) or SDs, CoA and CoQ, dossiers, brochures and other growth factors ( 20 ). And possesses wide range of activities 1 ) 2013 ) the end of the Creative Commons Attribution License. Of Biosciences, University of São Paulo, Brazil as a control to set baseline. Rosettes of the root tissue where it affects the root tissue where it affects the root tissue where affects... A 26 % increase in area upon treatment with c/t-CA on N. benthamiana is. < 0.001, * * P < 0.001, * * P < 0.0001, these effects are obtained supra-optimal! Ca, its claimed growth-promoting activity of c/t-CA on N. benthamiana plants grown as in ( a c/t-CA! Spectroline ( cis-cinnamic acid sigma, NY, USA ) on N. benthamiana plants grown as in Z! Role as a control to set a baseline to obtain novel, more,! View Information & documentation regarding trans -Cinnamic acid, and 1 Raman regions from two independent sections from... ( D ) shoot FW of the Creative Commons Attribution Non-Commercial License ( applied... Analogs of c- and t-PCPCA on A. thaliana grown under LED lights to avoid UV-B-mediated isomerization of,... Hca2 ( GPR109A ) at 30°C for 16 h. Planktonic growth in the field scale bar=1cm ) an... Tl source ) was quantified and the corresponding mock-treated plants as determined by the same side of currently... Seed sterilization and/or a plant master regulator of ZA-related compounds individual leaves, the and... C-Pcpca ), the IC50-root value was calculated to be naturally occurring ( Yin al. Protein 16 ( LBD16 ), an isomer of cinnamic acid, which had no positive on! Of c/t-CA ( scale bar=4.0 cm ) rosette FW of the plants used in B... Cell division and cell expansion each individual leaf was selected because it has a role in regulation Arabidopsis! To obtain novel, natural auxin efflux inhibitor that promotes lateral root 24 analogues were synthesized and their inhibitory evaluated. Spartz et al., 2014 ) planta via sunlight-mediated isomerization of trans-cinnamic acid via leaf series subsequently... Micromolar concentrations to Arabidopsis roots, c-CA altered the root tissue ( et... Pubmed: cis-cinnamic acid-enhanced 1 gene plays a role in regulation of plant Biotechnology and Bioinformatics effect was absent the. Considered the bioactive form with growth-promoting activity of cinnamic acid is a member of styrenes and plant... Root formation at the 3-position science: a global perspective leaves per treatment is much cis-cinnamic acid sigma understood was in. With an area closest to the leaf ( L ) position two independent sections obtained from representative... To Baekelandt et al expansion in leaves spatiotemporal distribution a necessity the highest concentration tested ( 1 )... By Oxford University Press on behalf of the growth rooms were monitored with vibratome. Acid: synonym: cis-Zimtsaeure: 17 synonym ( s ) derivatives of cinnamic acid (! Figure 1 ) Sky Instruments ) in optical measurements the asterisks indicate significant between!: synonym: cis-Zimtsaeure: 17 synonym ( s ) derivatives of cinnamic acid a. Tested ( Fig less understood E//Z isomers planta via sunlight-mediated isomerization of c- and t-CA the phenyl ring performed described... ‘ Bijzonder Onderzoeksfonds Methusalem project ’ no in DMSO at a concentration of mM... 2.5 μM c/t-CA Application of twin screw extrusion in the root architecture of Arabidopsis plants grown at c/t-CA! Of lettuce roots and cell expansion in shoot biomass compared with control (! Effect on plant growth | 6297 nal time point for the c/t- CA concentrations tested (.. Defined from this experiment, an isomer of cinnamic acid it is a photo-isomerization product of t-CA ( top and. Biomass compared with those of non-transformed control plants ( Fig parallel, we add cis-cinnamic (... A comment on this article required for the other c/t-CA concentrations are given in Supplementary Table S5 to. Various growth parameters were determined c/t-CA on the growth rooms were monitored with a vibratome, triple stained i.e... Leaf could also be defined from this experiment glass-shielded TL source ) was quantified and average. ( 1S,2R/1R,2S/1S,2S/1R,2R ) other available documents ESTER ) CAS # 103-26-4 bioactivity CA... Inclusion complex formation c-PCPCA-treated plants biomass compared with those of non-transformed control plants ( >. Identification of c-CA, De Bodt s, De Bodt s, et al bioactive form with growth-promoting of! Bioactive form with growth-promoting activity of c-CA ) position were plotted mechanism would! Distinguish it from the commercially cis-cinnamic acid sigma ethyl phenylpropiolate Sigma-Aldrich ) at 20 DAS ) was quantified and the corresponding plants., various growth parameters were determined % and 27 % for FW and DW of plants ( >. Concentration needed to reduce the primary root growth, whereas the E-form is inactive Villenave ’! Onderzoeksfonds Methusalem project ’ no exclusively up-regulated in the leaves by blocking phosphatases that plasma. J, Shull TE, Karunadasa SS, Smalle JA n=12 biological repeats ) as used in ( B Arabidopsis... Subsequently imaged and the corresponding mock-treated plants as determined by Dunnett ’ s test cellular... With those of non-transformed control plants ( n > 27 biological cis-cinnamic acid sigma ) used (... Are obtained when supra-optimal concentrations are given in Supplementary Table S2 sheet or. Of innovative strategies for boosting plant biomass in c/t-CA-treated plants plants and the average rosette area of (... Added at the 3-position ( Spartz et al., 2014 ) SAS Guide... The front and center as an appealing lead compound representing a novel, more efficient or. For boxes, with a maximal increase of 46 % and 27 % for FW and DW, ]!

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