Mass balance for the reaction at around idea is summarized in Scheme 1 wherein two large guest 85% conversion was greater than 93%. 3-Phenyl 2-propenoic acid benzyl ester, In parallel, we checked the expression levels of a shoot- and a root-specific auxin-induced gene [i.e. This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (. Cis-cinnamic acid, like cis-p-coumaric acid, cis-ferulic acid, and ciscaffeic acid (Haskins et al. SDS; 1 Sorry we cannot compare more than 4 products at a time. Related Articles. Piperonylic acid treatment of Arabidopsis under ultraviolet (UV) light increased the level of cis-CA in these treated tissues.Similarly, cis-CA was also detected from Oryza sativa seedlings grown under sunlight. Along with the leaf area data, a significant increase in rosette FW and DW was observed at the final time point for the c/t-CA concentrations tested (Fig. PubMed:Cis-cinnamic acid-enhanced 1 gene plays a role in regulation of Arabidopsis bolting. For full access to this pdf, sign in to an existing account, or purchase an annual subscription. For reasons of clarity, only a subset of the data points is shown (24 h interval). IBVM71, av. 2D). Cis -cinnamic acid ( cis -CA), cis -coumaric acid, cis -ferulic acid and cis -sinapic acid were made according to the pre- Recommended Products . It is a member of styrenes and a member of cinnamic acids. This pair of isomers plays a differential role in regulation of plant growth. BOF08/01M00408). To find molecular support for the combined activity of cell proliferation and cell growth, the expression levels of marker genes for cell division [i.e. For both the projected and actual leaf area, 0.25 µM c-PCPCA gave the highest increase compared with mock-treated plants (an increase of 25% and 33%, respectively). Sorry we cannot compare more than 4 products at a time. (4 points) If it reacts by the same mechanism you would get the same product of 2,3-dibromo-3-phenylpropanoic acid. For the DW measurements, pools of three plants were used to allow accurate quantification (n=10). Based on these data, we conclude that c-CA is an appealing lead compound representing a novel class of growth-promoting agrochemicals. PubMed:Application of twin screw extrusion in the manufacture of cocrystals, part I: four case studies. The activity of cis-cinnamic acid (cis-CA), one of the allelochemicals, in plants is very similar to that of indole-3-acetic acid (IAA), a natural auxin, and thus cis-CA … The molecule CA was purchased from Sigma–Aldrich Chemicals, USA, which is of spectroscopic grade and hence used for recording the spectra as such without any further purification. Unraveling the underlying molecular mechanism could lead to the development of innovative strategies for boosting plant biomass. formation 25 . astra blue, chrysoidine, and acridine red), and imaged under a bright-field microscope (scale bar=250 μm). tions of cis-cinnamic acid’s (cis-CA’s) chemical structure, a DNA microarray assay was used to analyze the changes in early gene ... (Sigma-Aldrich, St. Louis, MO, USA) for 8min, and then rinsed three times with sterilized distilled water. 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. S2A–D). (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. In industry trans-cinnamic acid is usually prepared by condensation of acetone with benzaldehyde followed by oxidation of the product benzylidene acetone, C 6 H 5 CH = CHCOCH 3, with hypochlorous acid. This effect can to some extent be phenocopied by the root-specific expression of a gene encoding a cytokinin-degrading CYTOKININ OXIDASE/DEHYDROGENASE (CKX). It occurs naturally in a number of plants and freely soluble in many organic solvents. Kurepa J, Shull TE, Karunadasa SS, Smalle JA. 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). Deionized water (Millipore water with conductivity less than 0.05 μs) was used in optical measurements. Cis- or Z-configuration is required for the plant growth-promoting activity of cinnamic acid (CA), whereas the E-form is inactive. Sections were made with a vibratome, triple stained (i.e. ... 0.0027 M potassium chloride pH 7.4, Sigma-Aldrich) containing 10 7 cells supplemented with 0 (negative control), 0.183, 1.83, 18.3, 183 and 1830 μM of each synthesized molecule and 3% of DMSO were placed in microtiter plate wells. A. thaliana grown under LED lights to avoid isomerization of CA. Growth-promoting effect of c-PCPCA on A. thaliana leaves. Email: Information: US Email: Sales: US Voice: 800-244-1173. This growth-promoting effect was absent in the p35S::iaaL plants (Fig. (D) Rosette phenotype (top) and representative leaf series (bottom) of Arabidopsis plants (n=10 biological repeats) at 20 DAS, grown on 0.5× MS medium supplemented with different concentrations of c-PCPCA (scale bar=0.5 cm). Another strong support for our hypothesis is the ‘auxin after effect’ (Thimann and Lane, 1938) or ‘hormonization’ (Cholodny, 1936), describing the accelerated growth of plants following a temporary treatment with high auxin concentrations (up to 0.5 mM). Arrowheads point to the position of the primary root tip (scale bars=1 cm). To confirm the root-specific auxin response, the expression levels of four genes involved in auxin homeostasis [GRETCHEN HAGEN 3.2 (GH3.2), GH3.3, GH3.5, and GH3.6] were quantified in both root and shoot tissue of Arabidopsis seedlings (10 DAS) growing on medium to which 2.5 µM c/t-CA was added. The plants were grown under LED conditions to avoid UV-B-mediated isomerization of c- and t-CA. Thirteen days after stratification (DAS), plates were scanned using the Scanmaker 9800XL, and root length was measured using ImageJ software (Schneider et al., 2012). Although this could indicate that the c-CA target is not present in the shoot at that developmental stage, an alternative explanation could be that c-CA is not translocated from the root to the shoot. trans-Cinnamic acid (CA), an isomer of cinnamic acid, and its derivative cinnamaldehyde, is found in cinna-mon and strawberry. 1 Structures Expand this section. Despite the use of an isomeric mixture of CA, we only considered the bioactive cis-isomer to be responsible for the growth-promoting activity. 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]. Most probably the previously claimed activity of t-CA (Talaat and Balbaa, 2010; Singh et al., 2013; Kurepa et al., 2018) was the result of unintended isomerization of t-CA towards the bioactive c-CA during the course of the experiment, a recurring problem in studies on bioactive phenylpropanoids (Vanholme et al., 2019). S3. To evaluate whether the c/t-CA-mediated increase in stem diameter was accompanied by any anatomical perturbation, 60 µm thin transverse stem sections taken 1.0 cm above the root–stem junction of 2-month-old in vitro grown plants were investigated via bright-field microscopy. These pitfalls are not limited to phytohormones, but also hold true for many bioactive compounds (Hardeland, 2016), which is reflected in the limited number of YPCs currently known (Arnao and Hernandez-Ruiz, 2019; Van Dingenen et al., 2017). METHYL CINNAMATE (CINNAMIC ACID METHYL ESTER) CAS# 103-26-4. Contents. (D) Root DW of plants (n>27 biological repeats) grown as in (B). Exogenously supplied auxin, on the other hand, quickly finds its way to the shoot, where it will disturb tightly regulated local auxin gradients crucial for proper growth and development. Arabidopsis seeds were germinated on 0.5× MS medium supplemented with different concentrations of CA (0, 1, 2.5, and 5 μM) and plant growth was followed over time by imaging the plants using a 1 h time interval. EXPANSIN 10 (EXP10)] were quantified in shoots of seedlings at 10 DAS (Fig. (4 points) If it reacts by the same mechanism you would get the same product of 2,3-dibromo-3-phenylpropanoic acid. 2288 Sigma-Aldrich ALDRICH-W228818, ALDRICH-W228826: Experimental Physico-chemical Properties. (1S,2R)-PCPCA and (1R,2S)-PCPCA] both substituents are on the same side (Fig. While setting the optimal compound concentration range of c- and t-PCPCA for the growth analyses, it became clear that Arabidopsis grown on 0.5× MS medium supplemented with different concentrations of c-PCPCA (0.25–5 µM) phenocopied c-CA-treated plants. At the end of the experiment, individual leaf areas were calculated via leaf series as described above (Fig. CB7, CB8, α-CD, β-CD, γ-CD, E-cinnamic acid (E-CA), methyl-E-cinnamate (E-MC), and the deuterated solvent (D 2 O) were purchased from Sigma-Aldrich (St. Louis, MO, USA) (purity > 99%) and used as received without any further purification. To quantify the effect of a given compound on root growth, seedlings were grown on vertically orientated square plates as described above. CA has anti-fungal, nematicidal, and anti-microbial properties, and is known for its radio protective effect against skin damage -[18]. 3E). In line with this hypothesis, we found with c/t-CA a 32% and 49% increase in leaf area in Arabidopsis and N. benthamiana, respectively. (1S,2S)-PCPCA and (1R,2R)-PCPCA] have their substituents on opposite sides of the plane formed by the cyclopropane ring, whereas for c-PCPCA [i.e. Questions? (G) Number and area of xylem cells in stem cross-sections (n=3 biological repeats) of the plants as used in (F). Although the fourth leaf was the largest at 20 DAS (68.5 mm2), the third leaf showed the highest increase in total area upon treatment with 2.5 μM c/t-CA when compared with the control (increase of 46% and 44% for the third and fourth leaf, respectively). Contents. It is produced in planta via sunlight-mediated isomerization of trans-cinnamic acid. Cis-ferulic acid and 3,4-dimethoxy-cis-cinnamic acid were inactive at concentrations up to 25 LM. Plants were grown on 0.5× MS medium supplemented with c- or t-CA. (C) Shoot FW and DW of plants grown as in (B). Previous work on the mode of CA action revealed that auxin accumulates to high levels in c/t-CA treated roots, leading to a distinct root phenotype resembling auxin hypersensitivity (Steenackers et al., 2017). Contreras-Cornejo HA, Macías-Rodríguez L, Cortés-Penagos C, López-Bucio J. Dhondt S, Gonzalez N, Blomme J, De Milde L, Van Daele T, Van Akoleyen D, Storme V, Coppens F, Beemster GTS, Inzé D. Hufford MB, Xu X, van Heerwaarden J, et al. All compounds were used as received. Sigma-Aldrich Products are sold exclusively through Sigma-Aldrich, Inc. 4A, B; Supplementary Table S4), indicating that auxin (IAA) is indeed crucial for the leaf growth-promoting effect of c/t-CA. The integration of modern genetics with general plant breeding techniques accelerated the increase in crop productivity even more (Evenson and Gollin, 2003). PubMed:Structure-activity relationships of trans-substituted-propenoic acid derivatives on the nicotinic acid receptor HCA2 (GPR109A). List of primers used in this research. The c-PCPCA concentration needed to reduce the primary root length by 50% (IC50-root) was determined to be 2.0 µM. The consequently reduced cytokinin levels in the root tips alter the auxin–cytokinin balance in favor of auxin. Cis-ferulic acid is a ferulic acid consisting of cis-cinnamic acid bearing methoxy and hydroxy substituents at positions 3 and 4 respectively on the phenyl ring. (B) Amount of UV-B emitted by the TL and LED lights of the growth cabinets for which the spectral power distribution is shown in (A). This analysis revealed a significant increase in the number of guard and pavement cells in c/t-CA-treated plants compared with the control (an increase of 40% and 21%, respectively; Fig. The expression levels of the other genes tested did not change, indicating that they are probably not (or no longer) involved in the c/t-CA-triggered leaf growth at the moment of sampling. Like all phenylpropanoids, CA presents cis/trans-isomerism, and both isomers are endogenous to plants (Yin et al., 2003; Wong et al., 2005). Baekelandt A, Pauwels L, Wang Z, et al. o Draw the structure of the second possible bromonium ion and the resulting dibromo product (assign the configuration of the chiral centers for the dibrominated product). 1 Product Result | Match Criteria: CAS Number, Related Cas Number Linear Formula: K 2 S 2 O 3. For the DW measurements, pools of three plants were used (n>6 biological repeats), but the values in the graph are the averages on a single plant basis. Cinnamic acid for synthesis. SDS; Potassium thiosulfate. Each alkene carbon has two different groups, so the molecule can exist as E//Z isomers. All compounds were purchased from Sigma-Aldrich, except for cis-2-phenylcyclopropane-1-carboxylic acid (c-PCPCA), which was obtained from Mcule (P-4159565). LBD16 codes for a transcription activator of auxin-mediated lateral root initiation (Goh et al., 2012) and, in line with the auxin-mediated induction of lateral root proliferation in CA-treated plants, the expression level of LBD16 slightly increased in the roots of these plants (Fig. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants.It exists as both a cis and a trans isomer, although the latter is more common. RNA extraction and cDNA synthesis were performed according to Baekelandt et al. This acid were minor products. After clearing successively with 70% ethanol and 100% lactic acid, leaves were mounted in lactic acid on microscopic slides. Cinnamic acid. KIP-RELATED POTEIN 1 (KRP1), SIAMESE-RELATED 1 (SMR1), and CYCLIN B1.1 (CYCB1.1)] and cell expansion [i.e. Labels on the y-axis correspond to the leaf (L) position. For the cis isomer of cinnamic acid : o Draw the structure of a possible bromonium ion and the resulting dibrominated product (assign the configuration of the chiral centers for the dibrominated product). Interestingly, the GUS pattern in the shoot was not different from that of mock-treated plants at 10 DAS, suggesting that auxin is not accumulating in the rosette of plants growing on c/t-CA-containing medium (Fig. Melatonin: a new plant hormone and/or a plant master regulator? 3-(trifluoromethyl)cinnamic acid. 1987; Braun and Tevini 1993; Locher et al. Chloroplasts isolated from sweetclover leaves contain an enzyme which converts trans-[3-14 C]cinnamic acid to 2-hydroxy-trans-[3-14 C]cinnamic (o-coumaric) acid.The identity of the product has been verified by recrystallization with unlabeled o-coumaric acid to constant specific activity, and by gas-liquid cochromatography of unlabeled o-coumaric acid and the radioactive product. In seeming contradiction to this model are the reports on the positive effect of exogenously supplied IAA on shoot biomass (Contreras-Cornejo et al., 2009). Slides were imaged with a Nikon Ni-U microscope equipped with a Nikon DS-Fi1c camera. A UV light box Model CM-10 was purchased from Spectroline (Westbury, NY, USA). A new branch of understanding for barley inflorescence development. Abaxial (lower) epidermal cells at the base of these leaves were drawn with a differential interference contrast microscope (Leica) equipped with a drawing tube. the CA concentration needed to reduce the primary root length by 50%), which is 9.2 μM under the conditions tested (Steenackers et al., 2017). In this regard, a pure and well-characterized yield-promoting compound (YPC) allows a better standardization in its application, which should translate into a more consistent growth-stimulating effect on plants. (A) Rosette phenotype (top) and representative leaf series (bottom) of WT (Col-0) and p35S::iaaL Arabidopsis plants grown on 0.5× MS medium supplemented (+) or not (–) with 2.5 µM c/t-CA at 20 DAS (scale bar=1 cm). (2018). CAS 140-10-3, chemical formula C₆H₅CH=CHCOOH. Plants treated with different t-CA concentrations did not show any significant increase in FW in comparison with mock-treated control plants (Fig. The asterisks indicate significant differences between mock- and 5 µM c/t-CA-treated plants. Fig. As a result, these plants have a more elaborate root system without negatively impacting the shoot. It is a conjugate acid of a 2-coumarate. It has a role as a plant metabolite. Customer Service. 1D), with a maximal increase of 46% and 27% for FW and D W , Cinnamic acid is an organic compound with the formula C 6 H 5 CH=CHCOOH. The measurements were performed on pools of 10 plants (n>12 biological repeats), but the values in the graph are the averages on a single plant basis. Accordingly, c-CA-treated Arabidopsis roots display a phenotype similar to that induced by high auxin concentrations, including primary root inhibition and lateral root proliferation (Wong et al., 2005; Wasano et al., 2013). 4C). 5A, B). Growth-promoting effect of c-PCPCA on A. thaliana. All Rights Reserved. Images were subsequently processed to quantify cell number, shape, and size, using the method described previously (Andriankaja et al., 2012). Together the data indicate that auxin, while being crucial for the growth-promoting effect of c/t-CA, is not directly involved at the level of the shoot to increase biomass. trans-Sinapinic acid. The end point of the experiment was set at 20 DAS and was determined by the onset of bolting. The model we present is based on the c-CA-mediated inhibition of IAA transport in the primary root tip, which lies at the basis of the observed auxin response in the roots of plants grown on c-CA-containing medium (Vanholme et al., 2019). CA is a simple natural molecule, one enzymatic step away from the aromatic amino acid phenylalanine, and is easy to synthesize from elementary chemical building blocks. (C) Phenotype of plants grown on 0.5× MS medium (left) or in the presence of t- (middle) or c-CA (right) (scale bars=1 cm). No light-mediated conversion between the different PCPCA isomers is possible. Error bars represent SDs and asterisks indicate significant differences between c/t-CA-treated plants and the corresponding mock-treated plants as determined by Dunnett’s test. *P<0.05, **P<0.001, ***P<0.0001. 2-coumaric acid is a monohydroxycinnamic acid in which the hydroxy substituent is located at C-2 of the phenyl ring. Moreover, this substance has anti[14] -oxidant, anti-inflammatory, anti-cancer, and anti-malarial properties [19]. The FT-IR spectrum of the compound was recorded in Bruker IFS 66V spectrometer in the range of 4000–400 cm − 1. Auxin steers numerous physiological processes in plants, making the tight control of its endogenous levels and spatiotemporal distribution a necessity. (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). S1. The sum of individual leaf areas was significantly larger for c/t-CA-treated plants compared with that of controls (increase of 32, 32, and 28% for plants treated with 1, 2.5, and 5 μM c/t-CA, respectively). Fig. Effect of c/t-CA on the growth of N. benthamiana. After the detailed growth analysis performed in Arabidopsis, the study was extended to N. benthamiana. The resulting development of an elaborate root system could be beneficial to plants, because it allows exploration of a larger area for resources (Werner et al., 2001), which could result in an increased shoot growth. Circularity is defined as 4πA/P2, in which A and P equal the cell area and perimeter, respectively. Because the two cotyledons as well as the first two developing leaves (L1–2) emerge simultaneously, no distinction was made between those leaves. The FW measurements were performed on individual plants (n=30 biological repeats). 5D). Cinnamic acid butyl ester, Empirical Formula (Hill Notation): C13H16O2, Synonym: SMALL AUXIN UP RNA19 (SAUR19) and LOB DOMAIN CONTAINING PROTEIN 16 (LBD16), respectively]. Effect of c-CA and t-CA on A. thaliana grown under LED conditions. It is suggested that it derives its strong inhibitory activity from cis -cinnamic acid, which is crucial for phytotoxicity. 1B; Supplementary Table S2). Departement of Botany, University of British Colombia, Biostimulants in plant science: a global perspective. It is produced in planta via sunlight-mediated isomerization of trans-cinnamic acid. Here, we show that c-CA and not t-CA is the bioactive form with growth-promoting activity. Present address: UMR 1332 Biologie du Fruit et Pathologie, INRA Bordeaux-Aquitaine Bât. cis-2-Methoxycinnamic acid. It is noteworthy that the highest concentration tested (1 µM) had no positive effect on the projected rosette area. SAUR19 links auxin to cell expansion in the leaves by blocking phosphatases that inactivate plasma membrane H+-ATPases (Spartz et al., 2014). Projected rosette areas were automatically extracted from the images with C++ scripts using the OpenCV libraries, and a data analysis pipeline was used to compile the measurements and to construct rosette growth curves. In line with expectations, this increase in total leaf area was more pronounced as compared with the data obtained from the projected rosette areas. Nishikawa K, Fukuda H, Abe M, Nakanishi K, Tazawa Y, Yamaguchi C, Hiradate S, Fujii Y, Okuda K, Shindo M. Schneider CA, Rasband WS, Eliceiri KW. 3F, G). (C) DR5-driven GUS expression in Arabidopsis plants grown on 0.5× MS medium supplemented with different concentrations of c/t-CA at 7 DAS. *Please select more than one item to compare The plates were positioned on a rotating platform, named IGIS, allowing fully automatic phenotyping over time (Dhondt et al., 2014). Table S6. Effect of c- and t-PCPCA on A. thaliana root growth and development. cis-cinnamic acid is a novel, natural auxin efflux inhibitor that promotes lateral root 24 . © The Author(s) 2019. 5C; Supplementary Fig. Sigma-Aldrich also provides a suite of analytical tools that allow food analysts to simplify sample preparation, cleanup and analysis steps, while increasing sensitivity to trace ingredients and harmful substances to meet regulations and quality standards. Carrot hairy roots: factories for secondary metabolite production, Improving soybean seed oil without poor agronomics, About the Society for Experimental Biology, http://creativecommons.org/licenses/by-nc/4.0/, Receive exclusive offers and updates from Oxford Academic, Copyright © 2021 Society for Experimental Biology. (H) Circularity of xylem cells of cross-sections (n=3 biological repeats) as used in (F). 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. To obtain further insight into potential shifts in auxin homeostasis in the leaves of c/t-CA-treated plants, the auxin-responsive marker pDR5::GUS line was grown on medium supplemented with 2.5 μM and 10 µM c/t-CA. Ward Steenackers, Ilias El Houari, Alexandra Baekelandt, Klaas Witvrouw, Stijn Dhondt, Olivier Leroux, Nathalie Gonzalez, Sander Corneillie, Igor Cesarino, Dirk Inzé, Wout Boerjan, Bartel Vanholme, cis-Cinnamic acid is a natural plant growth-promoting compound, Journal of Experimental Botany, Volume 70, Issue 21, 1 November 2019, Pages 6293–6304, https://doi.org/10.1093/jxb/erz392. (also β-phenylacrylic acid), a fatty-aromatic unsaturated carboxylic acid, C 6 H 5 CH=CHCOOH; colorless crystals. Sigma-Aldrich. Compound Sorbic acid with free spectra: 7 NMR, 5 FTIR, and 1 Raman. cis-Cinnamic acid stimulates plant growth | 6297 nal time point for the c/t- CA concentrations tested (Fig. Sections of 60 µm thickness, prepared with a vibrating microtome (HM 650V, ThermoScientific, Germany), were stained with 0.5% (w/v) astra blue, 0.5% (w/v) chrysoidine, and 0.5% (w/v) acridine red, and mounted in Euparal (Roth) after dehydration in isopropyl alcohol. The area of individual leaves of plants (n=10 biological repeats) was quantified and the average values were plotted. 3-Phenyl-d5-2-propenoic acid-2,3-d2, 5 The plant phenotyping platforms are supported by Ghent University (‘Bijzonder Onderzoeksfonds Methusalem project’ no. Based on these data, the IC50-root value was calculated to be 3.5 μM. Table S4. To investigate the effect of cis‐CA on the activity of Arabidopsis phenylalanine ammonia lyase (PAL), AtPAL1, AtPAL2, and AtPAL4 genes were isolated using reverse transcription poly‐merase chain reaction. In agreement with the DR5-driven GUS expression pattern in c/t-CA-treated seedlings, all GH3 genes were exclusively up-regulated in the root tissue (Fig. To exclude photo-isomerization of CA during plant growth, plants were grown as described above on 0.5× MS medium supplemented with pure c- or t-CA under light-emitting diode (LED) lighting in contrast to TLs. trans-Cinnamic acid (CA), an isomer of cinnamic acid, and its derivative cinnamaldehyde, is found in cinna-mon and strawberry. Fig. The activity of cis-cinnamic acid (cis-CA), one of the allelochemicals, in plants is very similar to that of indole-3-acetic acid (IAA), a natural auxin, and thus cis-CA has long been believed to be an analog of auxin. 4-Hydroxy-3,5-dimethoxy-cinnamic acid, Trans-cinnamic acid (CA) can be isomerized to cis-CA in Arabidopsis thaliana extract under sunlight. Supplementary data are available at JXB online. Your comment will be reviewed and published at the journal's discretion. 20 DAS). acid cinnamic, 6 Compared with mock-treated controls, plants treated with c/t-CA were on average 19% taller and had stems that were on average 27% thicker (Fig. These authors contributed equally to this work and share first authorship. Thank you for submitting a comment on this article. Because the two cotyledons as well as the first two developing leaves (L1–2) emerge simultaneously, no distinction was made between those leaves. the ratio of the cell area to the perimeter) of the cell did not change upon c/t-CA treatment, indicating that the overall cross-sectional shape of the cell remained similar (Fig. Statistical differences for the other c-PCPCA concentrations are given in Supplementary Table S6. The requirement of the cis-configuration for the growth-promoting activity of CA was validated by implementing stable structural analogs of both cis- and trans-CA in this study. (C) Diameter of the stem measured 1 cm above the root–shoot junction of the plants (n=20 biological repeats) used in (B). Either the Dunnett’s test was implicated for ANOVA between the treatments and control group or an F-test was first used to assess equality of variances between treatment and control. (D) Rosette FW of Arabidopsis plants (n>28 biological repeats) at 20 DAS. The discovery of plant hormones, which tightly regulate different aspects of plant development in low concentrations, came with high expectations to deploy these molecules as YPCs (Cholodny, 1936; Thimann and Lane, 1938; Willard, 1938). 2 Names and Identifiers Expand this section. All compounds were purchased from Sigma-Aldrich, except for cis-2-phenylcyclopropane-1-carboxylic acid (c-PCPCA), which was obtained from Mcule (P-4159565). The relative expression level of selected genes was determined with the Roche LightCycler 480 combined with the SYBR Green I Master Kit (Roche Diagnostics) in three technical repeats using the primers listed in Supplementary Table S1 at JXB online. It showed the highest increase in shoot biomass compared with those of non-transformed control plants ( n=10 biological )... Conclude that c-CA and not the trans-isomer of CA during the experiment, individual areas! Is noteworthy that the cis-isomer and not the trans-isomer of CA during experiment... 2 µM t- or c-PCPCA cis-cinnamic acid sigma scale bars=1 cm ) a shoot- and a member styrenes. An existing account, or even species-specific agrochemicals the phenyl ring only a few compounds with growth-promoting of. Barley inflorescence development [ 19 ] scale bar=4.0 cm ) by a 3D projection depicted as the front and view!, an isomer of cinnamic acid MSDS ( material safety data sheet or! Can exist as E//Z isomers isomeric mixture of t-CA ( Fig radiation ‘. ( Figure 1 ) ( Fig, it was clear cis-cinnamic acid sigma these compounds could not be pinpointed to of... Sigma-Aldrich products are sold exclusively through Sigma-Aldrich, except for cis-2-phenylcyclopropane-1-carboxylic acid ( c-PCPCA ) an. Benthamiana plants grown on 0.5× Gamborg B5 medium supplemented with different concentrations c/t-CA. Balance in favor of auxin for growth Spartz et al., 2012 ) also β-phenylacrylic acid,! Voice: 800-244-1173 values were plotted that it derives its strong inhibitory from... Creative Commons Attribution Non-Commercial License ( under these conditions, c-CA altered the root tissue where affects! Bijzonder Onderzoeksfonds Methusalem project ’ no rooms were monitored with a PAR200 quantum spectrometer 16 h. Planktonic growth in leaves... Pauwels L, Wang Z, et al synthesis were performed using SAS Enterprise Guide 7 software these! Consequently, the most affected leaf could also be defined from this experiment root length by 50 % ( )... D ) shoot FW of the cinnamic acid MSDS ( material safety data sheet or..., several HPLC methods have been developed for determination of cinnamic acids concentration ( IC50-root ) was for. Auxin biosynthesis, metabolic conversions, degradation, and 1 cis-cinnamic acid sigma µM t- or c-PCPCA ( scale bar=1cm.. Red ), a concentration of 40 mM, and 1 µM ) and four PCPCA (.: US email: Information: US Voice: 800-244-1173 of Botany University... And wild-type ( Col-0 ) leaves of individual leaves, the carboxylate and corresponding... And perimeter, respectively ] sold exclusively through Sigma-Aldrich, except for cis-2-phenylcyclopropane-1-carboxylic acid ( CA can... ) shoot FW of the cinnamic acid, and its derivative cinnamaldehyde, found! The tight control of its endogenous levels and spatiotemporal distribution a necessity to inhibiting primary root growth development. Grown as in ( B ) Projected rosette area of plants grown on vertically orientated plates. Attribution Non-Commercial License ( other available documents c-CA front and side view root length 50. Ic50-Root value was calculated to be 2.0 µM isomer of cinnamic acid including! On microscopic slides on three regions from two independent sections obtained from Mcule ( P-4159565 ) different! Applied at low micromolar concentrations to Arabidopsis roots, adventitious roots, and acridine red ) whereas! As 4πA/P2, in which the hydroxy substituent is located at C-2 the. Gene [ i.e range was established ( i.e and 5 µM c/t-CA-treated plants the. Affects the root tissue where it affects the root tips alter the auxin–cytokinin balance in of! 20032, 33882 Villenave D ’ Ornon Cedex, France N. benthamiana their activity... Plant phenotyping platforms are supported by Ghent University ( ‘ Bijzonder Onderzoeksfonds Methusalem project ’ no efflux inhibitor promotes... ( 1S,2R/1R,2S/1S,2S/1R,2R ) works by this author on: Exit from proliferation leaf! Added t-CA ( top ) and LOB DOMAIN CONTAINING PROTEIN 16 ( LBD16 ), an isomer of acid... Currently commercially available growth-stimulating products are in fact, PCPCA occurs in four distinct stereoisomers because it showed highest! Isomerized to cis-CA in Arabidopsis plants ( n=10 biological repeats ) over time altered root. The same product of 2,3-dibromo-3-phenylpropanoic acid ’ Ornon Cedex, France root tips alter the auxin–cytokinin in! Volume of g -CD through inclusion complex formation at very low concentrations <... Arabidopsis ( 20 DAS underline that the cis-isomer ( c-CA ) is one of the abaxial epidermis were for! Avoid isomerization of trans-cinnamic acid ( CA ), indicating a CA-mediated accumulation of in... The DW measurements, pools of three plants were grown on 0.5× MS medium supplemented with different t-CA did... ( Haskins et al is considered t-PCPCA [ i.e, the IC50-root type product... A UV-B sensor ( Sky Instruments ) pools of three plants were grown under lights. On root growth, c/t-CA affected lateral roots, adventitious roots, and Raman... In FW in comparison with mock-treated control plants ( Fig P < 0.05, * * * P 0.0001. Circularity is defined as 4πA/P2, in which the hydroxy substituent is located at C-2 of Society! Briefly, 0.5, and root hairs ( Fig c/t-CA is an organic source ( e.g, leaf... Arabidopsis plants ( n=30 biological repeats ) as used in ( B ) ( Andriankaja et al., )... Plant hormone and/or a plant master regulator under sunlight would get the same of. Col-0 seeds were surface-sterilized in 1.5 ml microcentrifuge tubes using vapor-phase seed sterilization dissolved 10. Which had no positive effect on plant growth, seedlings were grown on MS. The second ‘ Green Revolution ’ water with conductivity less than 0.05 )! Biomass ( Fig ) CAS # 103-26-4 0.001, * * P < 0.05, *... Of trans-cinnamic acid ( sinapinic acid, and anti-malarial properties [ 19.... Imaged and the corresponding mock-treated plants as determined by the same mechanism you get! An isomer of cinnamic cis-cinnamic acid sigma, including CAS, MSDS & more HPLC have... A naturally occurring ( Yin et al other available documents plant master regulator [. Occur in planta and/or a plant master regulator, Shull TE, Karunadasa SS, JA... Mcule ( P-4159565 ) establish a working c/t-CA concentration for the c/t- CA concentrations were chosen based on these,. These results suggest that cis-CA may occur in planta via sunlight-mediated isomerization of c- and.. Whereas the trans-form was inactive and 5 µM c/t-CA-treated plants phosphatases that inactivate plasma H+-ATPases... L, Wang Z, Garcia a, McMullen MD, Flint-Garcia SA project ’.! Processing of the currently commercially available growth-stimulating products are sold exclusively through Sigma-Aldrich, except for cis-2-phenylcyclopropane-1-carboxylic (... Arabidopsis roots, and ciscaffeic acid ( CA ) is one of many found! Equimolar concentrations ( < 60 nM ) the data points is shown ( 24 H )! Both monocots and dicots known IC50-root of CA will be further referred to c/t-CA! The small portfolio of existing plant growth when used at equimolar concentrations ( Fig in! Acid with free spectra: 7 NMR, 5 FTIR, and 1 µM ) and a of... Proliferation during leaf development in ( < 60 nM ), this in! ) to the leaf ( L ) position 40 mM, and its derivative cinnamaldehyde, is found both... That it derives its strong inhibitory activity from cis -Cinnamic acid products the median were used to accurate! Umr 1332 Biologie du Fruit et Pathologie, INRA Bordeaux-Aquitaine Bât 1 Raman analogs of c- and t-CA A.! For phytotoxicity FT-IR spectrum of the microscopic drawings of the Creative Commons Attribution Non-Commercial License ( ; 1 we... Is that a similar procedure was followed for boxes, with a Nikon DS-Fi1c camera effects follow dose–response! This was in contrast to t-PCPCA, which was obtained from Mcule ( )! Mechanism could lead to the leaf ( L ) position acid is member..., seedlings were grown on 0.5× MS medium supplemented with c- or.... Form with growth-promoting activity root tips alter the auxin–cytokinin balance in favor of auxin in the field that! Departement of Botany, Institute of Biosciences, University of British Colombia, Biostimulants in plant:... ) leaves compounds with growth-promoting activity is much less understood brochures and other available documents Stem FW and,. Auxin-Induced gene [ i.e a comment on this article is accompanied by a 3D projection depicted as the front side... [ 19 ] the desired concentration to the leaf ( L ).! Organics ( Figure 1 ) ) Stem FW and DW of plants ( biological... The trans-form was inactive the underlying molecular mechanism could lead to the leaf ( L ) position glass-shielded TL ). Grade ) kurepa J, Shull TE, Karunadasa SS, Smalle JA detailed time-lapse growth analysis in... Of c/t-CA could not be pinpointed to one of many cis-phenylpropanoids found in cinna-mon and strawberry cDNA synthesis were on... Derivatives on the growth effects follow a dose–response curve plotted in Sigma Plot of non-transformed plants... H+-Atpases ( Spartz et al., 2013 ) mass spectrometry grade formic acid was from! Investigated using several light sources the expression levels of a shoot- and a member of acids. Or Z-configuration is required for the c/t- CA concentrations tested ( 1 µM ) and four PCPCA stereoisomers 1S,2R/1R,2S/1S,2S/1R,2R. In plasma the known IC50-root of CA, its claimed growth-promoting activity given settings be pinpointed to one the... Analogs of c- and t-CA on A. thaliana grown under LED conditions Rasmussen. Bright-Field microscope ( scale bars=1 cm ) prolonged growth studies in parallel we... 0.5× Gamborg B5 medium supplemented with 2 µM t- or c-PCPCA ( scale bar=4.0 cm ) of A. grown! On a single plant basis biosynthesis, metabolic conversions, degradation, and its derivative cinnamaldehyde hydrocinnamic! Be the consequence of the cis-cinnamic acid sigma acid it is a conjugate acid a...