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Concept: Ferulic acid

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BACKGROUND: Hydroxycinnamates (HCs) are mainly produced in plants. Caffeic acid (CA), p-coumaric acid (PA), ferulic acid (FA) and sinapic acid (SA) are members of the HC family. The consumption of HC by human might prevent cardiovascular disease and some types of cancer. The solubility of HCs is increased through thioester conjugation to various compounds such as quinic acid, shikimic acid, malic acid, anthranilic acid, and glycerol. Although hydroxycinnamate conjugates can be obtained from diverse plant sources such as coffee, tomato, potato, apple, and sweet potato, some parts of the world have limited availability to these compounds. Thus, there is growing interest in producing HC conjugates as nutraceutical supplements. RESULTS: Hydroxycinnamoyl transferases (HCTs) including hydroxycinnamate-CoA shikimate transferase (HST) and hydroxycinnamate-CoA quinate transferase (HQT) were co-expressed with 4-coumarateCoA:ligase (4CL) in Escherichia coli cultured in media supplemented with HCs. Two hydroxycinnamoyl conjugates, p-coumaroyl shikimates and chlorogenic acid, were thereby synthesized. Total 29.1 mg/L of four different p-coumaroyl shikimates (3-p-coumaroyl shikimate, 4-p-coumaroyl shikimate, 3,4-di p-coumaroyl shikimate, 3,5-di p-coumaroyl shikimate, and 4,5-di p-coumaroyl shikimate) was obtained and 16 mg/L of chlorogenic acid was synthesized in the wild type E. coli strain. To increase the concentration of endogenous acceptor substrates such as shikimate and quinate, the shikimate pathway in E. coli was engineered. A E. coli aroL and aroK gene were mutated and the resulting mutants were used for the production of p-coumaroyl shikimate. An E. coli aroD mutant was used for the production of chlorogenic acid. We also optimized the vector and cell concentration optimization. CONCLUSIONS: To produce p-coumaroyl-shikimates and chlorogenic acid in E. coli, several E. coli mutants (an aroD mutant for chlorogenic acid production; an aroL, aroK, and aroKL mutant for p-coumaroyl-shikimates production) were made and each mutant was tested using an optimized construct. Using this strategy, we produced 235 mg/L of p-coumaroyl-shikimates and 450 mg/L of chlorogenic acid.

Concepts: Escherichia coli, Caffeic acid, Carboxylic acids, Ferulic acid, Matrix-assisted laser desorption/ionization, Chlorogenic acid, Quinic acid, Cyclitols

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Profound research has been done on the medicinal value of Brassica nigra (BN) seeds, and the leaves of the plant have been investigated in this study. The methanol extracts of the leaves were subjected to several in vitro studies. The antioxidant activity of methanol extract was demonstrated with a wide range of concentration, 10-500 µg mL(-1), and the antioxidant activity increased with the increase in concentration. Total phenol content was found to be 171.73 ± 5.043 gallic acid equivalents and the total flavonoid content 7.45 ± 0.0945 quercetin equivalents. Further quantification and identification of the compounds were done by HPTLC and GC-MS analyses. The predominant phenolic compounds determined by HPTLC were gallic acid, followed by quercetin, ferulic acid, caffeic acid and rutin. The free radical quenching property of BN leaf extract suggests the presence of bioactive natural compounds.

Concepts: Catechin, Quercetin, Caffeic acid, Resveratrol, Phenols, Ferulic acid, Gallic acid, Vanillin

27

A method of reversed-phase high-performance liquid chromatography (RP-HPLC) was established for the simultaneous determination of gallic acid, protocatechuic acid, catechin, vanillic acid, caffeic acid, ferulic acid, rutin, quercetin and syriacusin A in the ethanolic extracts from the five parts (roots, stems, leaves, seeds and exocarps) of Abutilon theophrasti Medic. The nine components in the sample were extracted with 70% ethanol solution in an ultrasonic bath for 25 min and chromatographically separated on a C18 analytical column (250 × 4.6 mm i.d., 5 µm) by gradient elution with water containing 0.1% (v/v) formic acid (pH 2.4) and acetonitrile as mobile phases, at a flow rate of 1.0 mL/min. The detection was conducted by ultraviolet-visible absorption. The proposed method showed good linearity between the peak area of each analyte and its concentration. Relative standard deviations of the instrumental intra-day and inter-day precision and method precision were less than 2.0, 3.5 and 2.0%. Recoveries were within the range of 87.3-100.8%. Limits of detection and quantification were 0.045-0.400 µg/mL (signal-to-noise ratio: 3) and 0.090-1.115 µg/mL (signal-to-noise ratio: 10), respectively. The proposed method was successfully applied to determine common phenols and flavonoids of Abutilon theophrasti Medic. The results indicated that the RP-HPLC system may provide a rapid method for the quality control of Abutilon theophrasti Medic.

Concepts: Chromatography, High performance liquid chromatography, Analytical chemistry, Acetic acid, Liquid chromatography-mass spectrometry, Caffeic acid, Ferulic acid

12

Conifers (softwoods) naturally lack syringyl units in their lignins, rendering lignocellulosic materials from such species more difficult to process than syringyl-rich hardwood species. Using a transformable Pinus radiata tracheary element (TE) system as an experimental platform, we investigated whether metabolic engineering can be used to create syringyl lignin in conifers. Pyrolysis-GC/MS and 2D-NMR analysis of P. radiata TE cultures transformed to express ferulate 5-hydroxylase (F5H) and caffeic acid O-methyltransferase (COMT) from Liquidambar styraciflua confirmed the production and incorporation of sinapyl alcohol into the lignin polymer. Transformation with F5H was sufficient for the production of syringyl lignin in TEs, but cotransformation with COMT improved its formation. In addition, lower levels of the pathway intermediate 5-hydroxyconiferyl alcohol were evidenced in cotransformation experiments, indicating that the introduction of the COMT overcame the inefficiency of the native pine methyltransferases for supporting sinapyl alcohol production.Our results provide the proof of concept that it is possible to generate a lignin polymer that contains syringyl units in softwood species such as P. radiata, suggesting that it might be possible to retain the outstanding fiber properties of softwoods while imbuing them with the lignin characteristics of hardwoods that are more favorable for industrial processing.

Concepts: Lignin, Caffeic acid, Wood, Ferulic acid, Pine, Liquidambar styraciflua, Hardwood, Softwood

6

A variety of natural vinegar products are found in civilizations around the world. A review of research on these fermented products indicates numerous reports of health benefits derived by consumption of vinegar components. Therapeutic effects of vinegar arising from consuming the inherent bioactive components including acetic acid, gallic acid, catechin, ephicatechin, chlorogenic acid, caffeic acid, p-coumaric acid, and ferulic acid cause antioxidative, antidiabetic, antimicrobial, antitumor, antiobesity, antihypertensive, and cholesterol-lowering responses. The aims of this article are to discuss vinegar history, production, varieties, acetic acid bacteria, and functional properties of vinegars.

Concepts: Ethanol, Acetic acid, Caffeic acid, Carboxylic acids, Ferulic acid, Matrix-assisted laser desorption/ionization, Vinegar, Chlorogenic acid

4

The present randomized controlled study aimed to investigate the in vivo distribution of constituents or metabolites of the standardized maritime pine bark extract Pycnogenol(®). Thirty-three patients with severe osteoarthritis scheduled for a knee arthroplasty were randomized to receive either 200 mg per day Pycnogenol(®) (P+) or no treatment (Co) over three weeks before surgery. Serum, blood cells, and synovial fluid samples were analyzed using liquid chromatography coupled to tandem mass spectrometry with electrospray ionization (LC-ESI/MS/MS). Considerable interindividual differences were observed indicating pronounced variability of the polyphenol pharmacokinetics. Notably, the highest polyphenol concentrations were not detected in serum. Catechin and taxifolin primarily resided within the blood cells while the microbial catechin metabolite δ-(3,4-dihydroxy-phenyl)-γ-valerolactone, ferulic, and caffeic acid were mainly present in synovial fluid samples. Taxifolin was detected in serum and synovial fluid exclusively in the P+ group. Likewise, no ferulic acid was found in serum samples of the Co group. Calculating ratios of analyte distribution in individual patients revealed a simultaneous presence of some polyphenols in serum, blood cells, and/or synovial fluid only in the P+ group. This is the first evidence that polyphenols distribute into the synovial fluid of patients with osteoarthritis which supports rationalizing the results of clinical efficacy studies.

Concepts: Protein, Mass spectrometry, Randomized controlled trial, Analytical chemistry, Caffeic acid, Ferulic acid, Matrix-assisted laser desorption/ionization, Tannin

3

Hydroxycinnamic acid derivatives are important class of polyphenolic compounds originated from the Mavolanate-Shikimate biosynthesis pathways in plants. Several simple phenolic compounds such as cinnamic acid, p-coumaric acid, ferulic acid, caffeic acid, chlorgenic acid, and rosmarinic acid belong to this class. These phenolic compounds possess potent antioxidant and anti-inflammatory properties. These compounds were also showed potential therapeutic benefit in experimental diabetes and hyperlipidemia. Recent evidences also suggest that they may serve as valuable molecule for the treatment of obesity related health complications. In adipose tissues, hydroxycinnamic acid derivatives inhibit macrophage infiltration and nuclear factor κB (NF-κB) activation in obese animals. Hydroxycinnamic acid derivatives also reduce the expression of the potent proinflammatory adipokines tumor necrosis factor-α (TNFα), monocyte chemoattractant protein-1 (MCP-1), and plasminogen activator inhibitor type-1 (PAI-1), and they increase the secretion of an anti-inflammatory agent adiponectin from adipocytes. Furthermore, hydroxycinnamic acid derivatives also prevent adipocyte differentiation and lower lipid profile in experimental animals. Through these diverse mechanisms hydroxycinnamic acid derivatives reduce obesity and curtail associated adverse health complications.

Concepts: Inflammation, Nutrition, Obesity, Adipose tissue, Anti-inflammatory, Carboxylic acids, Phenols, Ferulic acid

3

We analyzed the degree of browning (absorbance at 420 nm), the phenolics and the 5-hydroxymethylfurfural (5-HMF) content in six sparkling wines series kept at three temperatures (4 ºC, 16 ºC and 20 ºC) for over two years. Caffeic acid, trans-coutaric acid, p-coumaric acid and 5-HMF were the compounds with the greatest correlation with browning and time. 5-HMF was the only compound that evolved linearly at all temperatures. We propose that 5-HMF is a better time-temperature marker than the A420 parameter or phenolics, since it shows higher linearity with time at all temperatures, is more sensitive to temperature changes, and has lower variability. The kinetics of 5-HMF was studied showing a zero-order behavior. We propose mathematical models that wineries can use to predict the browning shelf life of their sparkling wines, as a function of storage time and temperature.

Concepts: Fundamental physics concepts, Temperature, Wine, Ferulic acid, Degrees of freedom, Fermentation, Winemaking, Chardonnay

2

Accumulating evidence suggest that diets rich in (poly)phenols may have positive effects on human health. Currently there is limited information regarding the effects of processing on the (poly)phenolic content of berries, in particular in processes related to the baking industry. This study investigated the impact of cooking, proving and baking on the anthocyanin, procyanidin, flavonol and phenolic acid content of wild blueberry using HPLC with UV and fluorescence detection. Anthocyanin levels decreased during cooking, proving, and baking, while no significant changes were observed for total procyanidins. However, lower molecular weight procyanidins increased and high molecular weight oligomers decreased during the process. Quercetin, ferulic and caffeic acid levels remained constant while increases were found for chlorogenic acid. Due to their possible health benefits, a better understanding of the impact of processing is important to maximize the retention of these phytochemicals in berry-containing-products.

Concepts: Nutrition, Quercetin, Caffeic acid, Ferulic acid, Baking, Chlorogenic acid, Anthocyanin, Blueberry

1

Vanillin is a popular and valuable flavour compound. It is the key constituent of the natural vanilla flavour obtained from cured vanilla pods. Here we show that a single hydratase/lyase type enzyme designated vanillin synthase (VpVAN) catalyses direct conversion of ferulic acid and its glucoside into vanillin and its glucoside, respectively. The enzyme shows high sequence similarity to cysteine proteinases and is specific to the substitution pattern at the aromatic ring and does not metabolize caffeic acid and p-coumaric acid as demonstrated by coupled transcription/translation assays. VpVAN localizes to the inner part of the vanilla pod and high transcript levels are found in single cells located a few cell layers from the inner epidermis. Transient expression of VpVAN in tobacco and stable expression in barley in combination with the action of endogenous alcohol dehydrogenases and UDP-glucosyltransferases result in vanillyl alcohol glucoside formation from endogenous ferulic acid. A gene encoding an enzyme showing 71% sequence identity to VpVAN was identified in another vanillin-producing plant species Glechoma hederacea and was also shown to be a vanillin synthase as demonstrated by transient expression in tobacco.

Concepts: DNA, Protein, Caffeic acid, Phenols, Ferulic acid, Matrix-assisted laser desorption/ionization, Vanillin, Vanilla