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Journal articles on the topic 'Hydroxycinnamate'

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Author: Grafiati

Published: 10 December 2022

Last updated: 29 January 2023

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1

Yang, Tzu-Yen, Mei-Li Wu, Chi-I. Chang, Chih-I. Liu, Te-Chih Cheng, and Yu-Jen Wu. "Bornyl cis-4-Hydroxycinnamate Suppresses Cell Metastasis of Melanoma through FAK/PI3K/Akt/mTOR and MAPK Signaling Pathways and Inhibition of the Epithelial-to-Mesenchymal Transition." International Journal of Molecular Sciences 19, no. 8 (July 24, 2018): 2152. http://dx.doi.org/10.3390/ijms19082152.

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Bornyl cis-4-hydroxycinnamate, a bioactive compound isolated from Piper betle stems, has the potential for use as an anti-cancer agent. This study investigated the effects of bornyl cis-4-hydroxycinnamate on cell migration and invasion in melanoma cells. Cell migration and invasion were compared in A2058 and A375 melanoma cell lines treated with/without bornyl cis-4-hydroxycinnamate (1–6 µM). To examine whether bornyl cis-4-hydroxycinnamate has a potential anti-metastatic effect on melanoma cells, cell migration and invasion assays were performed using a Boyden chamber assay and a transwell chamber in A2058 and A375 cells. Gelatin zymography was employed to determine the enzyme activities of MMP-2 and MMP-9. Cell lysates were collected for Western blotting analysis of matrix metalloproteinase (MMP)-2, MMP-9 and tissue inhibitors of metalloproteinase-1/2 (TIMP-1/2), as well as key molecules in the mitogen-activated protein kinase (MAPK), focal adhesion kinase (FAK)/ phosphatidylinositide-3 kinases (PI3K)/Akt/ mammalian target of rapamycin (mTOR), growth factor receptor-bound protein 2 (GRB2) signaling pathways. Our results demonstrated that bornyl cis-4-hydroxycinnamate is a potentially useful agent that inhibits melanoma cell migration and invasion, and altered melanoma cell metastasis by reducing MMP-2 and MMP-9 expression through inhibition of the FAK/PI3K/Akt/mTOR, MAPK, and GRB2 signaling pathways. Moreover, bornyl cis-4-hydroxycinnamate inhibited the process of the epithelial-to-mesenchymal transition in A2058 and A375 melanoma cells. These findings suggested that bornyl cis-4-hydroxycinnamate has potential as a chemotherapeutic agent, and warrants further investigation for its use in the management of human melanoma.

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2

Bahri, Meriem, Philippe Hance, Sébastien Grec, Marie-Christine Quillet, Francis Trotin, Jean-Louis Hilbert, and Theo Hendriks. "A “Novel” Protocol for the Analysis of Hydroxycinnamic Acids in Leaf Tissue of Chicory (Cichorium intybusL., Asteraceae)." Scientific World Journal 2012 (2012): 1–8. http://dx.doi.org/10.1100/2012/142983.

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A “novel” protocol is presented for easy and reliable estimation of soluble hydroxycinnamate levels inCichorium intybusL. leaf tissue in large-scale experiments. Samples were standardized by punching 6 discs per leaf, and hydroxycinnamates were extracted by submerging the discs in 80% ethanol with 5% acetic acid for at least 48 h in the darkness at 4°C. Residual dry mass of the discs was used fora posterioricorrection of compound levels. Chlorophyll was eliminated by chloroform, and the aqueous phases were transferred to microplates, dried, and dissolved in 50% methanol for HPLC analysis and storage. An HPLC program of 8 min was developed for the analysis of the extracts. Comparisons with extractions of liquid nitrogen powders indicated that the novel extraction method was reliable. No degradation of the major hydroxycinnamates—caftaric, chlorogenic, and chicoric acids—was observed, during maceration at ambient temperatures, or after storage for 1 year.

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3

López-Malvar, Ana, Zoila Reséndiz, Rogelio Santiago, José Cruz Jiménez-Galindo, and Rosa Ana Malvar. "Relationships between Stalk Resistance and Corn Borers, Agronomic Traits, and Cell Wall Hydroxycinnamates in a Set of Recombinant Inbred Lines from a Maize MAGIC Population." Agronomy 11, no. 6 (June 2, 2021): 1132. http://dx.doi.org/10.3390/agronomy11061132.

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Corn borers are the most important pest affecting maize. Resistance to corn borer attack may compromise plant fitness being detrimental for some important agronomic traits such as yield. Against the attack of this pest, cell wall-bound hydroxycinnamates have been previously described as a possible defense mechanism. In this study, agronomic characterization and cell wall-bound hydroxycinnamates quantification was performed in a subset of Recombinant Inbred Lines (RILs) from a Multiparent Advanced Generation Intercross (MAGIC) population that showed contrasting behavior against corn borer attack. Resistant lines showed greater concentration of p-coumaric acid, the only hydroxycinnamate that could have a role in the resistance in these particular materials. In addition, results indicated that resistant lines showed precocity, low grain moisture at harvest, and reduced plant height, thus, selecting for resistance may be detrimental for yield. In this way, a breeding strategy directly targeting grain yield in order to tolerate corn borer attack would be the recommended one.

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4

Trachtenberg, Aviram, Katarzyna Sidoryk, Somaya Alreate, Suchismita Muduli, Andrzej Leś, Marcin Cybulski, and Michael Danilenko. "Structure-Activity Relationship of Hydroxycinnamic Acid Derivatives for Cooperating with Carnosic Acid and Calcitriol in Acute Myeloid Leukemia Cells." Biomedicines 9, no. 11 (October 21, 2021): 1517. http://dx.doi.org/10.3390/biomedicines9111517.

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Plant phenolic compounds have shown the ability to cooperate with one another at low doses in producing enhanced anticancer effects. This may overcome the limitations (e.g., poor bioavailability and high-dose toxicity) in developing these agents as cancer medicines. We have previously reported that the hydroxycinnamic acid derivative (HCAD) methyl-4-hydroxycinnamate and the phenolic diterpene carnosic acid (CA) can synergistically induce massive calcium-dependent apoptosis in acute myeloid leukemia (AML) at non-cytotoxic concentrations of each agent. Here, we explored the chemical nature of the synergy between HCADs and either CA, in inducing cytotoxicity, or the active metabolite of vitamin D (calcitriol), in enhancing the differentiation of AML cells. This was done by determining the structure–activity relationship of a series of hydroxycinnamic acids and their derivatives (methyl hydroxycinnamates and hydroxybenzylideneacetones) in combination with CA or calcitriol. The HCAD/CA synergy required the following critical structural elements of an HCAD molecule: (a) the para-hydroxyl on the phenolic ring, (b) the carbon C7–C8 double bond, and (c) the methyl-esterified carboxyl. Thus, the only HCADs capable of synergizing with CA were found to be methyl-4-hydroxycinnamate and methyl ferulate, which also most potently enhanced calcitriol-induced cell differentiation. Notably, the C7–C8 double bond was the major requirement for this HCAD/calcitriol cooperation. Our findings may contribute to the rational design of novel synergistically acting AML drugs based on prototype combinations of HCADs with other agents studied here.

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5

Rawel, Harshadrai M., and Sascha Rohn. "Nature of hydroxycinnamate-protein interactions." Phytochemistry Reviews 9, no. 1 (December 10, 2009): 93–109. http://dx.doi.org/10.1007/s11101-009-9154-4.

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6

Wu, Huilu, Wei Ying, Jingkun Yuana, and Jian Dinga. "A Manganese(II) 4-Hydroxycinnamate Complex with the Tripod Ligand Tris(2-benzimidazolylmethyl)amine." Zeitschrift für Naturforschung B 63, no. 1 (January 1, 2008): 11–15. http://dx.doi.org/10.1515/znb-2008-0103.

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A six-coordinate manganese (II) complex with the tripod ligand tris(2-benzimidazolylmethyl) amine (ntb), with composition [Mn(ntb) (4-hydroxycinnamate)](4-hydroxycinnamate) · (DMF)0.5 · (H2O)3, was synthesized and characterized by elemental and thermal analyses, electrical conductivity, IR, and UV/vis spectral measurements. The crystal structure of the complex has been determined by the single-crystal X-ray diffraction. The Mn (II) cation is bonded to an ntb ligand and a 4-hydroxycinnamate ligand through four N atoms and two O atoms, giving a distorted octahedral coordination geometry. Cyclic voltammograms of the complex indicate a quasi-reversible Mn3+/Mn2+ couple. The X-band EPR spectrum of the complex exhibits a six-line manganese hyperfine splitting pattern with g = 2, A = 95, and confirms that the material is high-spin Mn(II).

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7

Parke, Donna, and L. Nicholas Ornston. "Toxicity Caused by Hydroxycinnamoyl-Coenzyme A Thioester Accumulation in Mutants of Acinetobacter sp. Strain ADP1." Applied and Environmental Microbiology 70, no. 5 (May 2004): 2974–83. http://dx.doi.org/10.1128/aem.70.5.2974-2983.2004.

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ABSTRACT Hydroxycinnamates, aromatic compounds that play diverse roles in plants, are dissimilated by enzymes encoded by the hca genes in the nutritionally versatile, naturally transformable bacterium Acinetobacter sp. strain ADP1. A key step in the hca-encoded pathway is activation of the natural substrates caffeate, p-coumarate, and ferulate by an acyl:coenzyme A (acyl:CoA) ligase encoded by hcaC. As described in this paper, Acinetobacter cells with a knockout of the next enzyme in the pathway, hydroxycinnamoyl-CoA hydratase/lyase (HcaA), are extremely sensitive to the presence of the three natural hydroxycinnamate substrates; Escherichia coli cells carrying a subclone with the hcaC gene are hydroxycinnamate sensitive as well. When the hcaA mutation was combined with a mutation in the repressor HcaR, exposure of the doubly mutated Acinetobacter cells to caffeate, p-coumarate, or ferulate at 10−6 M totally inhibited the growth of cells. The toxicity of p-coumarate and ferulate to a ΔhcaA strain was found to be a bacteriostatic effect. Although not toxic to wild-type cells initially, the diphenolic caffeate was itself converted to a toxin over time in the absence of cells; the converted toxin was bactericidal. In an Acinetobacter strain blocked in hcaA, a secondary mutation in the ligase (HcaC) suppresses the toxic effect. Analysis of suppression due to the mutation of hcaC led to the development of a positive-selection strategy that targets mutations blocking HcaC. An hcaC mutation from one isolate was characterized and was found to result in the substitution of an amino acid that is conserved in a functionally characterized homolog of HcaC.

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8

Nam, Nguyễn Đăng. "AN INVESTIGATION ON CORROSION INHIBITORS FOR STEEL IN ETHANOL FUEL BLEND." Vietnam Journal of Science and Technology 56, no. 3B (September 13, 2018): 11. http://dx.doi.org/10.15625/2525-2518/56/3b/12726.

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Cerium (III) chloride, sodium 4-hydroxycinnamate, and cerium 4-hydroxycinnamate have been successfully characterized as effective anodic, cathodic, and mixed inhibitors for steel in ethanol fuel blend by electrochemical and surface analyses. Electrochemical and surface analyses indicate that good inhibition performances are due to the formation of protective layer as a result of adsorption between the metal and inhibitor components. In addition, the inhibition mechanism of each inhibitor is also suggested and discussed in detail.

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9

Poole, R. C., and A. P. Halestrap. "Purification of aldehyde dehydrogenase from rat liver mitochondria by α-cyanocinnamate affinity chromatography." Biochemical Journal 259, no. 1 (April 1, 1989): 105–10. http://dx.doi.org/10.1042/bj2590105.

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1. alpha-Cyano-4-hydroxycinnamate was coupled to Sepharose CL-4B activated with 1,2:3,4-bisepoxybutane. 2. The low-Km rat liver mitochondrial aldehyde dehydrogenase was specifically bound to this affinity medium, and could subsequently be eluted with alpha-cyano-4-hydroxycinnamate. 3. The enzyme purified in this manner had a subunit molecular mass of 55 kDa and a pI of approx. 6.5. A minor component of approx. 57 kDa was also present and had a significantly higher pI value; this may be the precursor for aldehyde dehydrogenase. 4. alpha-Cyanocinnamate and some related compounds were found to be uncompetitive inhibitors of the enzyme. 5. No cytosolic aldehyde dehydrogenase was bound to the affinity column, but a protein from a rat liver post-mitochondrial supernatant with a molecular mass of approx. 25 kDa was bound, and could be eluted subsequently with alpha-cyano-4-hydroxycinnamate.

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10

Joachimiak, Andrzej, Grazyna Joachimiak, Lance Bigelow, Garrett Cobb, and Youngchang Kim. "HcaR Ligand and DNA Interactions in the Regulation of Catabolic Gene Expression." Acta Crystallographica Section A Foundations and Advances 70, a1 (August 5, 2014): C203. http://dx.doi.org/10.1107/s2053273314097964.

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Precise tuning of gene expression by transcriptional regulators determines the response to internal and external chemical signals and adjusts the metabolic machinery for many cellular processes. As a part of ongoing efforts by the Midwest Center for Structural Genomics, a number of transcription factors were selected to study protein-ligand and protein-DNA interactions. HcaR, a new member of the MarR/SlyA family of transcription regulators from soil bacteria Acinetobacter sp. ADP1, is an evolutionarily atypical regulator and represses hydroxycinnamate (hca) catabolic genes. Hydroxycinnamates containing an aromatic ring play diverse, critical roles in plant architecture and defense. HcaR regulates the expression of the hca catabolic operon, allowing this and related bacterial strains to utilize hydroxycinnamates: ferulate, p-coumarate, and caffeate as sole sources of carbon and energy. HcaR appears to be capable of responding to multiple aromatic ligands. These aromatic compounds bind to HcaR and reduce its affinity to the specific DNA sites. As a result, the transcription of genes encoding several catabolic enzymes is up-regulated. The HcaR structures of the apo-form and in a complex with several ligands: ferulic acid, 3,4 dihydroxybenzoic acid, vanillin and p-coumaric acid have been determined to understand how HcaR accommodates various aromatic compounds using the same binding pocket. We also have identified a potential DNA site for HcaR in the regulatory region upstream of the genes of the hca catabolic operon in Acinetobacter sp. ADP1 and have confirmed DNA binding by EMSA. The co-crystal structure of HcaR and palindromic 24-mer DNA has been determined for this DNA site. The crystal structures of HcaR, the apo-form, ligand-bound forms, and the specific DNA-bound form provide critical structural basis of protein-ligand (substrates or product) and protein-DNA interactions to understand the regulation of the expression of hydroxycinnamate (hca) catabolic genes. Our studies allow for better understanding of DNA-binding and regulation by this important group of transcription factors belonging to the MarR/SlyA families. This work was supported by National Institutes of Health grant GM094585 and by the U. S. Department of Energy, Office of Biological and Environmental Research, under contract DE-AC02-06CH11357.

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11

Bunzel, Mirko. "Chemistry and occurrence of hydroxycinnamate oligomers." Phytochemistry Reviews 9, no. 1 (July 25, 2009): 47–64. http://dx.doi.org/10.1007/s11101-009-9139-3.

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12

Li, Zhangmin, Zhenping Cai, Qiang Zeng, Tian Zhang, Liam John France, Changhua Song, Yaqin Zhang, et al. "Selective catalytic tailoring of the H unit in herbaceous lignin for methyl p-hydroxycinnamate production over metal-based ionic liquids." Green Chemistry 20, no. 16 (2018): 3743–52. http://dx.doi.org/10.1039/c8gc01252k.

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13

Soldevila-Sanmartín, Joan, Teresa Calvet, Merce Font-Bardia, Concepción Domingo, José A. Ayllón, and Josefina Pons. "Modulatingp-hydroxycinnamate behavior as a ditopic linker or photoacid in copper(ii) complexes with an auxiliary pyridine ligand." Dalton Transactions 47, no. 18 (2018): 6479–93. http://dx.doi.org/10.1039/c8dt00645h.

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14

Anwar, Hany F., Lars Skattebøl, Jan Skramstad, and Trond Vidar Hansen. "One-pot synthesis of ortho-hydroxycinnamate esters." Tetrahedron Letters 46, no. 32 (August 2005): 5285–87. http://dx.doi.org/10.1016/j.tetlet.2005.06.017.

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15

HASHIDOKO, Yasuyuki, Tomoko TANAKA, and Satoshi TAHARA. "Induction of 4-Hydroxycinnamate Decarboxylase in Klebsiella oxytoca Cells Exposed to Substrates and Non-substrate 4-Hydroxycinnamate Analogs." Bioscience, Biotechnology, and Biochemistry 65, no. 12 (January 2001): 2604–12. http://dx.doi.org/10.1271/bbb.65.2604.

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16

Paul, Amrita, Rakesh Mengji, Olive Abraham Chandy, Surajit Nandi, Manoranjan Bera, Avijit Jana, Anakuthil Anoop, and N. D. Pradeep Singh. "ESIPT-induced fluorescent o-hydroxycinnamate: a self-monitoring phototrigger for prompt image-guided uncaging of alcohols." Org. Biomol. Chem. 15, no. 40 (2017): 8544–52. http://dx.doi.org/10.1039/c7ob02280h.

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17

Qin, Xiaohan, Mengzhu Zhang, Xu Hu, Qian Du, Zhipeng Zhao, Yue Jiang, and Yuxia Luan. "Nanoengineering of a newly designed chlorin e6 derivative for amplified photodynamic therapy via regulating lactate metabolism." Nanoscale 13, no. 27 (2021): 11953–62. http://dx.doi.org/10.1039/d1nr01083b.

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18

Poole, R. C., and A. P. Halestrap. "Reconstitution of the l-lactate carrier from rat and rabbit erythrocyte plasma membranes." Biochemical Journal 254, no. 2 (September 1, 1988): 385–90. http://dx.doi.org/10.1042/bj2540385.

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1. Rat and rabbit erythrocyte plasma-membrane proteins were solubilized with decanoyl-N-methylglucamide and reconstituted into liposomes. The procedure includes detergent removal by gel filtration, followed by a freeze-thaw step. 2. The rate of [1-14C]pyruvate uptake into these vesicles was inhibited by approx. 70% by alpha-cyano-4-hydroxycinnamate and p-chloromercuribenzenesulphonate. The extent of uptake at equilibrium was not affected by the presence of these inhibitors, but was dependent on the osmolarity of the suspending medium. 3. Reconstituted bovine erythrocyte membranes, which have no lactate carrier, showed a much slower time course of pyruvate uptake, with no inhibitor-sensitive component. 4. L- but not D-lactate competed for alpha-cyano-4-hydroxycinnamate-sensitive [1-14C]pyruvate uptake.

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19

Marks, Serena C., William Mullen, and Alan Crozier. "Flavonoid and Hydroxycinnamate Profiles of English Apple Ciders." Journal of Agricultural and Food Chemistry 55, no. 21 (October 2007): 8723–30. http://dx.doi.org/10.1021/jf071155u.

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20

Milkowski, Carsten, Alfred Baumert, and Dieter Strack. "Identification of four Arabidopsis genes encoding hydroxycinnamate glucosyltransferases." FEBS Letters 486, no. 2 (December 7, 2000): 183–84. http://dx.doi.org/10.1016/s0014-5793(00)02270-5.

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21

Edlund, G. L., and A. P. Halestrap. "The kinetics of transport of lactate and pyruvate into rat hepatocytes. Evidence for the presence of a specific carrier similar to that in erythrocytes." Biochemical Journal 249, no. 1 (January 1, 1988): 117–26. http://dx.doi.org/10.1042/bj2490117.

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Time courses of L-lactate and pyruvate uptake into isolated rat hepatocytes were measured in a citrate-based medium to generate a pH gradient (alkaline inside), by using the silicone-oil-filtration technique at 0 degrees C to minimize metabolism. At low concentrations of lactate and pyruvate (0.5 mM), transport was inhibited by over 95% by 5 mM-alpha-cyano-4-hydroxycinnamate, whereas at higher concentrations (greater than 10 mM) a significant proportion of transport could not be inhibited. The rate of this non-inhibitable transport was linearly related to the substrate concentration, was less with pyruvate than with L-lactate, and appeared to be due to diffusion of undissociated acid. Uptake of D-lactate was not inhibited by alpha-cyano-4-hydroxycinnamate and occurred only by diffusion. Kinetic parameters for the carrier-mediated transport process were obtained after correction of the initial rates of uptake of lactate and pyruvate in the absence of 5 mM-alpha-cyano-4-hydroxycinnamate by that in the presence of inhibitor. Under the conditions used, the Km values for L-lactate and pyruvate were 2.4 and 0.6 mM respectively and the Ki for alpha-cyano-4-hydroxycinnamate as a competitive inhibitor was 0.11 mM. Km values for the transport of L-lactate and pyruvate into rat erythrocytes under similar conditions were 3.0 and 0.96 mM. The Vmax. of lactate and pyruvate transport into hepatocytes at 0 degrees C was 3 nmol/min per mg of protein. Carrier-mediated transport of 0.5 mM-L-lactate was inhibited by 0.2 mM-p-chloromercuribenzenesulphonate (greater than 90%), 0.5 mM-quercetin (80%), 0.6 mM-isobutylcarbonyl-lactyl anhydride (70%) and 0.5 mM-4,4′-di-isothiocyanostilbene-2,2′-disulphonate (50%). A similar pattern of inhibition of lactate transport is seen in erythrocytes. It is suggested that the same or a similar carrier protein exists in both tissues. The results also show that L-lactate transport into rat hepatocytes is very rapid at physiological temperatures and is unlikely to restrict the rate of its metabolism. Differences between our results and those of Fafournoux, Demigne & Remesy [(1985) J. Biol. Chem. 260, 292-299] are discussed.

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22

Poole, R. C., A. P. Halestrap, S. J. Price, and A. J. Levi. "The kinetics of transport of lactate and pyruvate into isolated cardiac myocytes from guinea pig. Kinetic evidence for the presence of a carrier distinct from that in erythrocytes and hepatocytes." Biochemical Journal 264, no. 2 (December 1, 1989): 409–18. http://dx.doi.org/10.1042/bj2640409.

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1. Time courses for the uptake of L-lactate, D-lactate and pyruvate into isolated cardiac ventricular myocytes from guinea pig were determined at 11 degrees C or 0 degrees C (for pyruvate) in a citrate-based buffer by using a silicone-oil-filtration technique. These conditions enabled initial rates of transport to be measured without interference from metabolism of the substrates. 2. At a concentration of 0.5 mM, transport of all these substrates was inhibited by approx. 90% by 5 mM-alpha-cyano-4-hydroxycinnamate; at 10 mM-L-lactate a considerable portion of transport could not be inhibited. 3. Initial rates of L-lactate and pyruvate uptake in the presence of 5 mM-alpha-cyano-4-hydroxycinnamate were linearly related to the concentration of the monocarboxylate and probably represented diffusion of the free acid. The inhibitor-sensitive component of uptake obeyed Michaelis-Menten kinetics, with Km values for L-lactate and pyruvate of 2.3 and 0.066 mM respectively. 4. Pyruvate and D-lactate inhibited the transport of L-lactate, with Ki values (competitive) of 0.077 and 6.6 mM respectively; the Ki for pyruvate was very similar to its Km for transport. The Ki for alpha-cyano-4-hydroxycinnamate as a non-competitive inhibitor was 0.042 mM. 5. These results indicate that L-lactate, D-lactate and pyruvate share a common carrier in guinea-pig cardiac myocytes; the low stereoselectivity for L-lactate over D-lactate and the high affinity for pyruvate distinguish it from the carrier in erythrocytes and hepatocytes. The metabolic roles for this novel carrier in heart are discussed.

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23

Wiemer, E. A. C., P. A. M. Michels, and F. R. Opperdoes. "The inhibition of pyruvate transport across the plasma membrane of the bloodstream form of Trypanosoma brucei and its metabolic implications." Biochemical Journal 312, no. 2 (December 1, 1995): 479–84. http://dx.doi.org/10.1042/bj3120479.

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The pyruvate produced by glycolysis in the bloodstream form of the trypanosome is excreted into the host bloodstream by a facilitated diffusion carrier. The sensitivity of pyruvate transport for alpha-cyano-4-hydroxycinnamate and the compound UK5099 [alpha-cyano-beta-(1-phenylindol-3-yl)acrylate], which are known to be selective inhibitors of pyruvate (monocarboxylate) transporters present in mitochondria and the plasma membrane of eukaryotic cells, was examined. The trypanosomal pyruvate carrier was found to be rather insensitive to inhibition by alpha-cyano-4-hydroxycinnamate (Ki = 17 mM) but could be completely blocked by UK5099 (Ki = 49 microM). Inhibition of pyruvate transport resulted in the retention, and concomitant accumulation, of pyruvate within the trypanosomes, causing acidification of the cytosol and osmotic destabilization of the cells. Our results indicate that this physiological state has serious metabolic consequences and ultimately leads to cell death; thereby identifying the pyruvate carrier as a possible target for chemotherapeutic intervention.

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24

Babst, Benjamin A., Han-Yi Chen, Hong-Qiang Wang, Raja S. Payyavula, Tina P. Thomas, Scott A. Harding, and Chung-Jui Tsai. "Stress-responsive hydroxycinnamate glycosyltransferase modulates phenylpropanoid metabolism in Populus." Journal of Experimental Botany 65, no. 15 (May 6, 2014): 4191–200. http://dx.doi.org/10.1093/jxb/eru192.

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25

Otani, H., Y. E. Lee, I. Casabon, and L. D. Eltis. "Characterization of p-Hydroxycinnamate Catabolism in a Soil Actinobacterium." Journal of Bacteriology 196, no. 24 (September 29, 2014): 4293–303. http://dx.doi.org/10.1128/jb.02247-14.

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26

Santiago, Rogelio, Rosa Ana Malvar, Jaime Barros-Rios, Luis Fernando Samayoa, and Ana Butrón. "Hydroxycinnamate Synthesis and Association with Mediterranean Corn Borer Resistance." Journal of Agricultural and Food Chemistry 64, no. 3 (January 12, 2016): 539–51. http://dx.doi.org/10.1021/acs.jafc.5b04862.

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27

Edlin, Duncan A. N., Arjan Narbad, Michael J. Gasson, J. Richard Dickinson, and David Lloyd. "Purification and characterization of hydroxycinnamate decarboxylase from Brettanomyces anomalus." Enzyme and Microbial Technology 22, no. 4 (March 1998): 232–39. http://dx.doi.org/10.1016/s0141-0229(97)00169-5.

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28

Chen, Ling. "Tetraaquabis(4,4′-bipyridine)zinc(II) bis(trans-4-hydroxycinnamate)." Acta Crystallographica Section E Structure Reports Online 65, no. 7 (June 20, 2009): m807. http://dx.doi.org/10.1107/s1600536809023204.

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29

Parke, Donna, and L. Nicholas Ornston. "Hydroxycinnamate (hca) Catabolic Genes from Acinetobacter sp. Strain ADP1 Are Repressed by HcaR and Are Induced by Hydroxycinnamoyl-Coenzyme A Thioesters." Applied and Environmental Microbiology 69, no. 9 (September 2003): 5398–409. http://dx.doi.org/10.1128/aem.69.9.5398-5409.2003.

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ABSTRACT Hydroxycinnamates are plant products catabolized through the diphenol protocatechuate in the naturally transformable bacterium Acinetobacter sp. strain ADP1. Genes for protocatechuate catabolism are central to the dca-pca-qui-pob-hca chromosomal island, for which gene designations corresponding to catabolic function are dca (dicarboxylic acid), pca (protocatechuate), qui (quinate), pob (p-hydroxybenzoate), and hca (hydroxycinnamate). Acinetobacter hcaC had been cloned and shown to encode a hydroxycinnamate:coenzyme A (CoA) SH ligase that acts upon caffeate, p-coumarate, and ferulate, but genes for conversion of hydroxycinnamoyl-CoA to protocatechuate had not been characterized. In this investigation, DNA from pobS to an XbaI site 5.3 kb beyond hcaC was captured in the plasmid pZR8200 by a strategy that involved in vivo integration of a cloning vector near the hca region of the chromosome. pZR8200 enabled Escherichia coli to convert p-coumarate to protocatechuate in vivo. Sequence analysis of the newly cloned DNA identified five open reading frames designated hcaA, hcaB, hcaK, hcaR, and ORF1. An Acinetobacter strain with a knockout of HcaA, a homolog of hydroxycinnamoyl-CoA hydratase/lyases, was unable to grow at the expense of hydroxycinnamates, whereas a strain mutated in HcaB, homologous to aldehyde dehydrogenases, grew poorly with ferulate and caffeate but well with p-coumarate. A chromosomal fusion of lacZ to the hcaE gene was used to monitor expression of the hcaABCDE promoter. LacZ was induced over 100-fold by growth in the presence of caffeate, p-coumarate, or ferulate. The protein deduced to be encoded by hcaR shares 28% identity with the aligned E. coli repressor, MarR. A knockout of hcaR produced a constitutive phenotype, as assessed in the hcaE::lacZ-Kmr genetic background, revealing HcaR to be a repressor as well. Expression of hcaE::lacZ in strains with knockouts in hcaA, hcaB, or hcaC revealed unambiguously that hydroxycinnamoyl-CoA thioesters relieve repression of the hcaABCDE genes by HcaR.

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30

Smith, Michael A., Valerie B. Weaver, David M. Young, and L. Nicholas Ornston. "Genes for Chlorogenate and Hydroxycinnamate Catabolism (hca) Are Linked to Functionally Related Genes in the dca-pca-qui-pob-hca Chromosomal Cluster of Acinetobacter sp. Strain ADP1." Applied and Environmental Microbiology 69, no. 1 (January 2003): 524–32. http://dx.doi.org/10.1128/aem.69.1.524-532.2003.

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ABSTRACT Hydroxycinnamates are ubiquitous in the environment because of their contributions to the structure and defense mechanisms of plants. Additional plant products, many of which are formed in response to stress, support the growth of Acinetobacter sp. strain ADP1 through pathways encoded by genes in the dca-pca-qui-pob chromosomal cluster. In an appropriate genetic background, it was possible to select for an Acinetobacter strain that had lost the ability to grow with caffeate, a commonly occurring hydroxycinnamate. The newly identified mutation was shown to be a deletion in a gene designated hcaC and encoding a ligase required for conversion of commonly occurring hydroxycinnamates (caffeate, ferulate, coumarate, and 3,4-dihydroxyphenylpropionate) to thioesters. Linkage analysis showed that hcaC is linked to pobA. Downstream from hcaC and transcribed in the direction opposite the direction of pobA transcription are open reading frames designated hcaDEFG. Functions of these genes were inferred from sequence comparisons and from the properties of knockout mutants. HcaD corresponded to an acyl coenzyme A (acyl-CoA) dehydrogenase required for conversion of 3,4-dihydroxyphenylpropionyl-CoA to caffeoyl-CoA. HcaE appears to encode a member of a family of outer membrane proteins known as porins. Knockout mutations in hcaF confer no discernible phenotype. Knockout mutations in hcaG indicate that this gene encodes a membrane-associated esterase that hydrolyzes chlorogenate to quinate, which is metabolized in the periplasm, and caffeate, which is metabolized by intracellular enzymes. The chromosomal location of hcaG, between hcaC (required for growth with caffeate) and quiA (required for growth with quinate), provided the essential clue that led to the genetic test of HcaG as the esterase that produces caffeate and quinate from chlorogenate. Thus, in this study, organization within what is now established as the dca-pca-qui-pob-hca chromosomal cluster provided essential information about the function of genes in the environment.

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Kumar, Ajay, Shiva Kant, and Sukh Mahendra Singh. "α-Cyano-4-hydroxycinnamate induces apoptosis in Dalton’s lymphoma cells." Anti-Cancer Drugs 24, no. 2 (February 2013): 158–71. http://dx.doi.org/10.1097/cad.0b013e3283586743.

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32

UCHIYAMA, Hirofumi, Yasuyuki HASHIDOKO, Yuhki KURIYAMA, and Satoshi TAHARA. "Identification of the 4-Hydroxycinnamate Decarboxylase (PAD) Gene ofKlebsiella oxytoca." Bioscience, Biotechnology, and Biochemistry 72, no. 1 (January 23, 2008): 116–23. http://dx.doi.org/10.1271/bbb.70496.

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Majumder, P. L., and Anjali Pal. "24-Methylene cycloartanyl p-hydroxycinnamate from the orchid Cirrhopetalum elatum." Phytochemistry 24, no. 9 (January 1985): 2120–22. http://dx.doi.org/10.1016/s0031-9422(00)83137-4.

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34

Kokpol, Udom, Warinthorn Chavasiri, Vallapa Chittawong, and D. Howard Miles. "Taraxeryl cis-p-Hydroxycinnamate, a Novel Taraxeryl from Rhizophora apiculata." Journal of Natural Products 53, no. 4 (July 1990): 953–55. http://dx.doi.org/10.1021/np50070a026.

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35

Jezek, Petr, and Jirí Borecky. "Mitochondrial uncoupling protein may participate in futile cycling of pyruvate and other monocarboxylates." American Journal of Physiology-Cell Physiology 275, no. 2 (August 1, 1998): C496—C504. http://dx.doi.org/10.1152/ajpcell.1998.275.2.c496.

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The physiological role of monocarboxylate transport in brown adipose tissue mitochondria has been reevaluated. We studied pyruvate, α-ketoisovalerate, α-ketoisocaproate, and phenylpyruvate uniport via the uncoupling protein (UCP1) as a GDP-sensitive swelling in K+ salts induced by valinomycin or by monensin and carbonyl cyanide- p-(trifluoromethoxy)phenylhydrazone in Na+ salts. We have demonstrated that this uniport is inhibited by fatty acids. GDP inhibition in K+ salts was not abolished by an uncoupler, indicating a negligible monocarboxylic acid penetration via the lipid bilayer. In contrast, the electroneutral pyruvate uptake (swelling in ammonium pyruvate or potassium pyruvate induced by change in pH) mediated by the pyruvate carrier was inhibited by its specific inhibitor α-cyano-4-hydroxycinnamate but not by fatty acids. Moreover, α-cyano-4-hydroxycinnamate enhanced the energization of brown adipose tissue mitochondria, which was monitored fluorometrically by 2-(4-dimethylaminostyryl)-1-methylpyridinium iodide and safranin O. Consequently, we suggest that UCP1 might participate in futile cycling of unipolar ketocarboxylates under certain physiological conditions while expelling these anions from the matrix. The cycle is completed on their return via the pyruvate carrier in an H+ symport mode.

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36

Liu, Chang-Jun. "Biosynthesis of hydroxycinnamate conjugates: implications for sustainable biomass and biofuel production." Biofuels 1, no. 5 (September 2010): 745–61. http://dx.doi.org/10.4155/bfs.10.48.

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37

Tang, Zhi-Wei, Jun-Dan Fu, Long-Ping Jiang, and Yi-Hang Wen. "catena-Poly[[[tetraaquamanganese(II)]-μ-4,4′-bipyridine] bis(3-hydroxycinnamate) dihydrate]." Acta Crystallographica Section E Structure Reports Online 65, no. 8 (July 22, 2009): m979. http://dx.doi.org/10.1107/s1600536809028360.

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38

Bisby, Roger H., and Anthony W. Parker. "Structure of the radical from one-electron oxidation of 4-hydroxycinnamate." Free Radical Research 35, no. 1 (January 2001): 85–91. http://dx.doi.org/10.1080/10715760100300621.

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39

Bunce, Richard A., and Joel D. Moore. "TETRAHYDROPYRANYLOXY-DIRECTEDorthoLITHIATION OF AROMATIC SYSTEMS. SYNTHESIS OFo-HYDROXYCINNAMATE ESTERS FROM PHENOLS." Organic Preparations and Procedures International 29, no. 3 (June 1997): 293–99. http://dx.doi.org/10.1080/00304949709355199.

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40

WILLIAMSON, G., and C. B. FAULDS. "ChemInform Abstract: Enzymic Hydrolysis of Naturally Occurring Flavonoid and Hydroxycinnamate Esters." ChemInform 30, no. 1 (June 18, 2010): no. http://dx.doi.org/10.1002/chin.199901290.

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41

Lee, Jeong-Sun, Song-Hae Bok, Yong Bok Park, Mi-Kyung Lee, and Myung-Sook Choi. "4-Hydroxycinnamate Lowers Plasma and Hepatic Lipids without Changing Antioxidant Enzyme Activities." Annals of Nutrition and Metabolism 47, no. 3-4 (2003): 144–51. http://dx.doi.org/10.1159/000070037.

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42

Dudáš, Matej, Mária Vilková, Tibor Béres, Miroslav Repčák, and Pavol Mártonfi. "Two New Isomers of Palmityl-4-hydroxycinnamate from Flowers of Taraxacum Species." Natural Product Communications 11, no. 6 (June 2016): 1934578X1601100. http://dx.doi.org/10.1177/1934578x1601100635.

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Two isomers, (Z)- and (E)-palmityl 4-hydroxycinnamate [hexadecyl(2Z)-3-(4-hydroxyphenyl)prop-2-enoate and hexadecyl(2E)-3-(4-hydroxyphenyl)prop-2-enoate] were isolated for the first time from ligulate flowers of Taraxacum linearisquameum Soest (sect. Taraxacum). The highest amount of these compounds was detected in pollen grains; 0.26 mg/100 mg DW of the (E)-isomer and 0.096 mg/100 mg DW of the (Z)-isomer. The structures of these compounds were elucidated by a combination of HPLC-ESI-Qtof-MS and ID and 2D NMR spectroscopy. Their presence was confirmed in other species of Taraxacum, but they were not found in the male-sterile triploid agamospermous taxon T. parnassicum.

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43

Jaiswal, Rakesh, Joseph Kiprotich, and Nikolai Kuhnert. "Determination of the hydroxycinnamate profile of 12 members of the Asteraceae family." Phytochemistry 72, no. 8 (June 2011): 781–90. http://dx.doi.org/10.1016/j.phytochem.2011.02.027.

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44

Rautengarten, Carsten, Edward Baidoo, Jay D. Keasling, and Henrik Vibe Scheller. "A Simple Method for Enzymatic Synthesis of Unlabeled and Radiolabeled Hydroxycinnamate-CoA." BioEnergy Research 3, no. 2 (March 30, 2010): 115–22. http://dx.doi.org/10.1007/s12155-010-9085-3.

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45

Best, Leonard, and Stephen Tomlinson. "Inhibition of pyruvate oxidation in rat islets by α-cyano-4-hydroxycinnamate." Biochemical Pharmacology 37, no. 10 (May 1988): 2019–22. http://dx.doi.org/10.1016/0006-2952(88)90550-3.

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46

Beaugrand, J., D. Crônier, P. Debeire, and B. Chabbert. "Arabinoxylan and hydroxycinnamate content of wheat bran in relation to endoxylanase susceptibility." Journal of Cereal Science 40, no. 3 (November 2004): 223–30. http://dx.doi.org/10.1016/j.jcs.2004.05.003.

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47

Metcalfe, H. K., J. P. Monson, S. G. Welch, and R. D. Cohen. "Carrier-mediated efflux of ketone bodies in isolated rat hepatocytes." Clinical Science 71, no. 6 (December 1, 1986): 755–61. http://dx.doi.org/10.1042/cs0710755.

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1. The rate of efflux of ketone bodies has been studied in isolated hepatocytes prepared from starved rats and preloaded with d-3-[14C]hydroxybutyrate. 2. Efflux of ketone bodies was temperature-dependent, saturable and inhibited by α-cyano-3-hydroxycinnamate and phloretin. The rate of efflux was also reduced by 6 mmol/l lactate and pyruvate added to the external medium. 3. Under conditions of simulated metabolic acidosis in the hepatocyte suspension medium, ketone body efflux rate was reduced. 4. The experimental data suggest that hepatic plasma membrane ketone body transit is carrier-mediated.

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Tan, Eric M. M., Saeed Amirjalayer, Szymon Smolarek, Alexander Vdovin, Anouk M. Rijs, and Wybren J. Buma. "Conformational Heterogeneity of Methyl 4-Hydroxycinnamate: A Gas-Phase UV–IR Spectroscopic Study." Journal of Physical Chemistry B 117, no. 17 (April 23, 2013): 4798–805. http://dx.doi.org/10.1021/jp312624e.

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de Groot, Mattijs, Evgeniy V. Gromov, Horst Köppel, and Wybren Jan Buma. "High-Resolution Spectroscopy of Methyl 4-Hydroxycinnamate and Its Hydrogen-Bonded Water Complex." Journal of Physical Chemistry B 112, no. 14 (April 2008): 4427–34. http://dx.doi.org/10.1021/jp7101308.

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50

Mullen, W., B. Nemzer, A. Stalmach, S. Ali, and E. Combet. "Polyphenolic and Hydroxycinnamate Contents of Whole Coffee Fruits from China, India, and Mexico." Journal of Agricultural and Food Chemistry 61, no. 22 (May 28, 2013): 5298–309. http://dx.doi.org/10.1021/jf4003126.

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