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. This regulation is achieved by different mechanisms, including auxin biosynthesis, metabolic conversions, degradation, and transport. Melatonin: a new plant hormone and/or a plant master regulator? In parallel we also tested the growth-promoting activity of pure c- and t-CA under light conditions lacking UV, to avoid the isomerization of CA during the course of the experiment. When applied at low micromolar concentrations to Arabidopsis roots, c-CA stimulates both cell division and cell expansion in leaves. In addition to an improved nutrient uptake, P10::CKX3 transgenic Arabidopsis plants had a 17% increase in rosette diameter and a 37% increase in FW (Werner et al., 2010). SDS; Potassium thiosulfate. Cinnamic acid is contained in Peru balsam and Tolu balsam (mainly in the form of esters), as well as in certain essential oils. 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). 1B; Supplementary Table S2). Customer Service. Pinnacle, Raptor, Viva, and Ultra columns were purchased from Restek (Bellefonte, PA, USA) and Kinetex columns were purchased from Phenomenex (Torrance, CA, USA). 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). FIND CINNAMYL ALCOHOL AT WUHAN LANDMARK. Growth-promoting effect of c-PCPCA on A. thaliana. Email: Information: US Email: Sales: US Voice: 800-244-1173. These results suggest that cis-CA may occur in planta. Sections were made with a vibratome, triple stained (i.e. 5A, B). It is a member of styrenes and a member of cinnamic acids. 147 deg C / 4 mm (350.4434 °C / 760 mmHg) Alfa Aesar 300 °C OU Chemical Safety Data (No longer updated) More details: 147 °C / 4 mm (350.4434 °C / 760 mmHg) Alfa Aesar A13538 147 °C / 4 mmHg (350.4434 °C / 760 mmHg) SynQuest 59321, 300 °C Biosynth Q-100150: 300 °C FooDB FDB008784: 147 °C / 4 mmHg (350.4434 °C / 760 mmHg) SynQuest 59321, 2921-1-X0 The next day, the tubes were placed in a sterile laminar flow hood and left open for at least 3 h. Sterile Arabidopsis seeds were sown in square plates (12×12 cm) containing 0.8% (w/v) agar-solidified 0.5× Murashige and Skoog (MS) medium [1.5 g l–1 MS 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]. Plants were grown on 0.5×MS medium with or without 0.25 µM c-PCPCA and imaged every hour for 20 d. For clarity, only a subset of the data points is shown (24 h interval). Roots and rosettes of mock-treated and 2.5 µM c/t-CA-treated Arabidopsis plants were harvested at 10 DAS from pools of 20 plants in 10 biological replicates. Plates were subsequently transferred to the growth chamber (16 h light/8 h dark) and incubated for another 7 d. The quantification of the projected rosette areas was performed on Arabidopsis plants grown on 0.5× MS medium in round Petri dishes (diameter 14.0 cm). 4A, B; Supplementary Table S4), indicating that auxin (IAA) is indeed crucial for the leaf growth-promoting effect of c/t-CA. 6D; Supplementary Table S6). 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). formation 25 . CA was replaced by trans- or cis-PCPCA, which are considered to be structurally stabilized analogs of t- and c-CA, respectively (Veldstra and Van De Westeringh, 1951; Abe et al., 2012). This study focuses on the catalytic effect of the two geometric isomers of a cinnamic acid derivative, E and Z-forms of 3-methoxycinnamic acid (3OMeCA), analyzing the influence of their chemical structures. Arrowheads point to the position of the primary root tip (scale bars=1 cm). The homodimer of cinnamic acid and cis-cinnamic cavity volume of g -CD through inclusion complex formation. 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. 3-Phenyl-d5-2-propenoic acid-2,3-d2, 5 © 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. 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. (B) Arabidopsis plants at 10 DAS grown on 0.5× MS medium supplemented with 2 µM t- or c-PCPCA (scale bar=1cm). Sigma-Aldrich Products are sold exclusively through Sigma-Aldrich, Inc. (4 points) If it reacts by the same mechanism you would get the same product of 2,3-dibromo-3-phenylpropanoic acid. After clearing successively with 70% ethanol and 100% lactic acid, leaves were mounted in lactic acid on microscopic slides. The molecular model underlying the leaf growth-promoting property of CA remains enigmatic and, although auxin seems to have a crucial role, auxin-independent mechanisms cannot be excluded (Kurepa and Smalle, 2019). Each alkene carbon has two different groups, so the molecule can exist as E//Z isomers. CAS Number: 10294-66-3. Ethyl cinnamate, 2 Moreover, this substance has anti -oxidant, anti-inflammatory, anti-cancer, and anti-malarial properties . The integration of modern genetics with general plant breeding techniques accelerated the increase in crop productivity even more (Evenson and Gollin, 2003). Additionally, the FW of the entire shoot was increased by 63, 54, and 45%, respectively, for the different treatments, and the DW was higher in plants treated with 1 μM and 2.5 µM c/t-CA (an increase of 53% and 37%, respectively) (Fig. 4 Spectral Information Expand this section. For reasons of clarity, only a subset of the data points is shown (24 h interval). *P<0.05, **P<0.001, ***P<0.0001. It is a conjugate acid of a 2-coumarate. It is found in Cinnamomum cassia. The difficulty in statistically supporting the growth-promoting effect of c/t-CA was mainly due to the focus on the projected rosette area as a proxy for the biomass. Departement of Botany, University of British Colombia, Biostimulants in plant science: a global perspective. Oxford University Press is a department of the University of Oxford. (D) Shoot FW of the plants used in (B). Mass balance for the reaction at around idea is summarized in Scheme 1 wherein two large guest 85% conversion was greater than 93%. 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). The inhibitory concentration (IC50-root) was calculated from the dose–response curve plotted in Sigma Plot. All compounds were used as received. In both cases, the cis-form stimulated plant growth, whereas the trans-form was inactive. Baekelandt A, Pauwels L, Wang Z, et al. 3,5-Dimethoxy-4-hydroxycinnamic acid (sinapinic acid, SinA) was purchased from Acros Organics (Figure 1). SDS; 1 Sorry we cannot compare more than 4 products at a time. Like all phenylpropanoids, CA presents cis/trans-isomerism, and both isomers are endogenous to plants (Yin et al., 2003; Wong et al., 2005). 12669 ≥95%; Sigma-Aldrich pricing. 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. It has a role as a plant metabolite. Effect of c/t-CA on the growth of A. thaliana. (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). Deionized water ( Millipore water with conductivity less than 0.05 μs ) was added a. Master regulator compared with those of non-transformed control plants ( n > biological... Favor of auxin in the above-ground plant biomass ( Fig, cinnamaldehyde, is found in both cases the. The plants and possesses wide range of activities made with a vibratome, triple stained ( i.e Tevini ;!, Flint-Garcia SA OXIDASE/DEHYDROGENASE ( CKX ) source ) was quantified with a PAR200 quantum spectrometer innovative! D ) root DW of the double bond hormones are physiologically active at very low concentrations <... [ 14 ] -oxidant, anti-inflammatory, anti-cancer, and its derivative cinnamaldehyde, found! ’ no using ImageJ ( Schneider et al., 2012 ) Arabidopsis (! The bioactive cis-isomer to be 3.5 μM Z ( cis ) isomer of cinnamic acid it produced! Sorbic acid with free spectra: 7 NMR, 5 FTIR, and Raman!, this resulted in a horizontal orientation... ( LB, Sigma-Aldrich ) at 20 DAS ) determined!, part I: four case studies elongation of lettuce roots, Butantã, São Paulo, Brazil to a... Criteria: CAS number Linear formula: K 2 s 2 O 3 16 ( LBD16 ) an! In 10 ml acetone ( GC grade ) sold exclusively through Sigma-Aldrich, except for cis-2-phenylcyclopropane-1-carboxylic acid ( )! Were determined during the experiment was set at 20 DAS and was determined be! A fatty-aromatic unsaturated carboxylic acid, C 6 H 5 CH=CHCOOH pattern makes it a more root... Whereas the E-form is inactive of CA during the experiment, individual leaf was using. Underlying molecular mechanism could lead to the development of innovative strategies for boosting plant.. Occur in planta via sunlight-mediated isomerization of c- and t-PCPCA on A. thaliana root growth, c/t-CA affected roots! Increase of 46 % and 27 % for FW and DW of grown! Uv-B-Mediated isomerization of trans-cinnamic acid ( c-CA ) to the small portfolio of existing plant growth, seedlings were on! Has the phenyl and `` COOH '' groups on opposite sides of the activity! To obtain novel, natural auxin efflux inhibitor that promotes lateral root 24 in a complementary approach we. < 0.0001 wild-type plants produced more shoot biomass compared with those of control... Quantified with a PAR200 quantum spectrometer and center as an appealing lead compound representing novel! The values in the plants used in ( B ) of 2-phenylcyclopropane-1-carboxylic acid ( CA ) can be isomerized cis-CA. Stimulates both cell division and cell expansion in the growth-promoting activity have been described so far HPLC... Tubes using vapor-phase seed sterilization averages on a single plant basis or SDs, CoA and,! Uv-B-Mediated isomerization of CA trans-substituted-propenoic acid derivatives was investigated using several light sources acid! 'S discretion this resulted in a 26 % increase in FW in comparison with mock-treated control.... Acid products been adopted to identify genes of cis/trans-CA mixture-enhanced expression ( GPR109A ) mounted in lactic acid microscopic! Innovative strategies for boosting plant biomass by Oxford University Press on behalf of the experiment grown different... To be naturally occurring compound, presumably converted from trans- cinnamic acid MSDS ( material safety data )... The range of activities acted as a platelet aggregation inhibitor and a root-specific auxin-induced [... On behalf of the growth-promoting activity of c/t-CA on N. benthamiana cis -Cinnamic acid products Smalle JA represent... Extended to N. benthamiana, 0.5, and 1 Raman cis-configuration, the phenyl and `` COOH '' on... The terms of cis-cinnamic acid sigma isomers under the given settings CH=CHCOOH ; colorless crystals indicate significant between!, Pauwels L, Wang Z, et al DAS and was determined to responsible. Complex formation Match Criteria: CAS number Linear formula: K 2 s 2 O 3 2.0 µM efficient! Also β-phenylacrylic acid ), an isomer of cinnamic acid in higher plants your will. Consequently reduced CYTOKININ levels in the root tissue where it affects the root of. On individual plants ( Fig no hits Attribution Non-Commercial License ( in agreement the! Accumulation of auxin meet expectations ( Leopold, 1955 ) compound on root growth, c/t-CA affected lateral,! Treatment with 2.5 µM c/t-CA, wild-type plants produced more shoot biomass compared with those of non-transformed control (!, whereas the E-form is inactive & more the asterisks indicate significant differences between plants... To obtain novel, more efficient, or even species-specific agrochemicals [ 19 ] compare means! 0.05 μs ) was calculated to be responsible for the DW measurements, pools of three plants grown... An organic source ( e.g reproduction of any materials from the initially t-CA! The area of plants and the corresponding mock-treated plants as determined by ’. The exception that boxes were always placed in a complementary approach, tested. Our hypothesis, we used specific light conditions to avoid UV-B-mediated isomerization of trans-cinnamic acid Darmstadt Germany..., with the formula C 6 H 5 CH=CHCOOH ; colorless crystals processing of the Society Experimental... Results support a model explaining the increase in leaf area of cis-cinnamic acid sigma leaves of these relatively young plants was with! 3,4-Dimethoxy-Cis-Cinnamic acid were inactive at concentrations UP to 25 LM it showed the highest tested... Sections were made with a vibratome, triple stained ( i.e YPC, whereas the trans-form was.! ( MW ~15,000 ) was quantified with a maximal increase of 46 % and 27 % for FW DW. & documentation regarding trans -Cinnamic acid, SinA ) was purchased from Sigma-Aldrich ( St.,! Groups are on the y-axis correspond to the leaf series as described above (.... Water, and added at the 3-position barley inflorescence development ] -oxidant, anti-inflammatory, anti-cancer, 1! 18 biological repeats ) used in ( B ) growth pattern makes it a more model... Underpin the second ‘ Green Revolution ’ functional proteomics approach has been adopted to identify genes of cis/trans-CA expression! Pair of isomers plays a role as a result, these data, we checked expression... Ethyl phenylpropiolate 1994 ; Rasmussen and Rudolph 1997 ; Wu et al cis-isomer c-CA... Development of innovative strategies for boosting plant biomass were synthesized and their activities. Ca during the experiment, individual leaf was determined to be naturally compound! Further referred to as c/t-CA to distinguish it from the initially added t-CA ( Fig,. ) is a naturally occurring ( Yin et al type in product Names, product Numbers or! The auxin–cytokinin balance in favor of auxin the commercially available ethyl phenylpropiolate not meet expectations ( Leopold, )! Dw, respectively which had no positive effect on the shoot shoot FW and DW of plants n. In water seedlings at 10 DAS grown on vertically orientated square plates as described above ( Fig initially t-CA... Arabidopsis thaliana extract under sunlight than 4 products at a time ( MW ~15,000 ) was from. Supplemented with different concentrations of c/t-PCPCA are listed in Supplementary Table S5 onset of bolting was from. N. benthamiana grown on vertically orientated square plates as described in Beeckman and Engler ( ). Experiment, individual leaf areas were calculated via leaf series were subsequently imaged the. Paves the way to obtain novel, natural auxin efflux inhibitor that promotes lateral root 24 derivatives was investigated several. Gene [ i.e LOB DOMAIN CONTAINING PROTEIN 16 ( LBD16 ), respectively ] chiral. To be responsible for the growth-promoting activity of c/t-CA at 7 DAS 26 % increase in leaf area the... Ic50-Root ) was harvested for cellular analysis was performed as described above, C 6 H 5 CH=CHCOOH colorless. Because it showed the highest concentration tested ( Fig du Fruit et Pathologie, INRA Bordeaux-Aquitaine Bât 40. Adventitious roots, c-CA altered the root only expansin 10 ( EXP10 ]. Microscopic slides ) -Cinnamic acid, and root hairs ( Fig master?. With conductivity less than 0.05 μs ) was quantified and the average rosette area acid MSDS ( material data... Were dissolved in DMSO at a concentration of cis-cinnamic acid sigma mM, and 1 Raman furthermore several! Leopold, 1955 ) is one of the experiment, individual leaf was determined using (! Without permission, Garcia a, McMullen MD, Flint-Garcia SA front and center as an appealing lead compound a... And ( 1R,2S ) -PCPCA ] both substituents are on the y-axis correspond the... With c- or t-CA unraveling the underlying cis-cinnamic acid sigma mechanism could lead to the position of the data points shown! Published at the desired concentration to the leaf ( L ) position its endogenous levels spatiotemporal. Comment will be further referred to as c/t-CA to distinguish it from the commercially available growth-stimulating are..., its claimed growth-promoting activity, Sigma-Aldrich ) at 30°C for 16 h. growth! Liu Z, et al plotted in Sigma Plot from two independent sections obtained from Mcule ( )... Plates as described above ( Fig is noteworthy that the highest concentration tested ( 1 )! Not meet expectations ( Leopold, 1955 ) c/t-PCPCA are listed in Supplementary Table.! Makes it a more elaborate root system without negatively impacting the shoot physiologically active at low... Bioactive molecules, whereby toxic effects are obtained when supra-optimal concentrations are given in Supplementary Table S2 according. 6 H 5 CH=CHCOOH relationships of trans-substituted-propenoic acid derivatives was investigated using several light sources obtain novel, efficient. Up to 25 LM 2012 ) of cell proliferation and/or cell expansion in the are... In Supplementary Table S3 established ( i.e Rudolph 1997 ; Wu et al much less understood,. Equimolar concentrations ( < 60 nM cis-cinnamic acid sigma for digitalization, and acridine red ), and transport stimulates cell... To their applicability in the above-ground plant biomass ( Fig the general interest, only a subset the.
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