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Taking into account the increasing number of antibiotic-resistant bacteria, actual research focused on plant extracts is vital. The aim of our study was to investigate leaf and stem ethanolic extracts of Artemisia absinthium L. and Artemisia annua L. in order to explore their antioxidant and antibacterial activities. Total phenolic content (TPC) was evaluated spectrophotometrically. Antioxidant activity was evaluated by DPPH and ABTS. The antibacterial activity of wormwood extracts was assessed by minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) in Escherichia coli, Staphylococcus aureus, Listeria monocytogenes, and Salmonella enteritidis cultures, and by zone of inhibition in Klebsiella carbapenem-resistant enterobacteriaceae (CRE) and Escherichia coli extended-spectrum β-lactamases cultures (ESBL). The Artemisia annua L. leaf extract (AnL) exhibited the highest TPC (518.09 mg/mL) and the highest expression of sinapic acid (285.69 ± 0.002 µg/mL). Nevertheless, the highest antioxidant capacity (1360.51 ± 0.04 µM Trolox/g DW by ABTS and 735.77 ± 0.02 µM Trolox/g DW by DPPH) was found in Artemisia absinthium L. leaf from the second year of vegetation (AbL2). AnL extract exhibited the lowest MIC and MBC for all tested bacteria and the maximal zone of inhibition for Klebsiella CRE and Escherichiacoli ESBL. Our study revealed that AbL2 exhibited the best antioxidant potential, while AnL extract had the strongest antibacterial effect.

Background Laccases and laccase-like multicopper oxidases (LMCOs) oxidize a vast array of phenolic compounds and amines, releasing water as a byproduct. Their low substrate specificity is responsible for their tremendous biotechnological interest, since they have been used for numerous applications. However, the laccases characterized so far correspond to only a small fraction of the laccase genes identified in fungal genomes. Therefore, the knowledge regarding the biochemistry and physiological role of minor laccase-like isoforms is still limited. Results In the present work, we describe the isolation, purification and characterization of two novel LMCOs, PcLac1 and PcLac2, from Pleurotus citrinopileatus. Both LMCOs were purified with ion-exchange chromatographic methods. PcLac2 was found to oxidize a broader substrate range than PcLac1, but both LMCOs showed similar formal potentials, lower than those reported previously for laccases from white-rot fungi. Proteomic analysis of both proteins revealed their similarity with other well-characterized laccases from Pleurotus strains. Both LMCOs were applied to the oxidation of ferulic and sinapic acid, yielding oligomers with possible antioxidant activity. Conclusions Overall, the findings of the present work can offer new insights regarding the biochemistry and variability of low-redox potential laccases of fungal origin. Low-redox potential biocatalysts could offer higher substrate selectivity than their high-redox counterparts, and thus, they could be of applied value in the field of biocatalysis.

Human Group IIA secreted phospholipase A2 (sPLA2-IIA) enzyme plays a crucial role in several chronic inflammatory diseases such asasthma, atherosclerosis, gout, bronchitis, etc. Several studies showed that the antioxidants exert an anti-inflammatory function by inhibiting the sPLA2-IIA enzyme. Hence, the present study evaluated an antioxidant molecule, sinapic acid, for sPLA2-IIA inhibition as an anti-inflammatory function. Initially, the antioxidant efficacy of sinapic acid was evaluated, and it showed greater antioxidant potency. Further, sinapic acid inhibited 94.4 ± 4.83% of sPLA2-IIA activity with an IC50 value of 4.16 ± 0.13 µM. The mode of sPLA2-IIA inhibition was examined by increasing the substrate concentration from 30 to 120nM and the calcium concentration from 2.5 to 15 mM, which did not change the level of inhibition. Further, sinapic acid altered the intrinsic fluorescence and distorted the far UltraViolet Circular Dichroism (UV-CD) spectra of the sPLA2-IIA, indicating the direct enzyme-inhibitor interaction. Sinapic acid reduced the sPLA2-IIA mediated hemolytic activity from 94 ± 2.19% to 12.35 ± 2.57% and mouse paw edema from 171.75 ± 2.2% to 114.8 ± 1.98%, demonstrating the anti-inflammatory efficiency of sinapic acid by in situ and in vivo methods, respectively. Finally, sinapic acid reduced the hemorrhagic effect of Vipera russelli venom hemorrhagic complex-I (VR-HC-I) as an anti-hemorrhagic function. Thus, the above experimental results revealed the sinapic acid potency to be an antioxidant, anti-inflammatory and anti-hemorrhagic molecule, and therefore, it appears to be a promising therapeutic agent.

Background: Vriddhi is one of the Rasayana herbs in Ayurveda broadly used in vitality, strengthening Ayurvedic formulations. To fulfill steeply increased demand and declined supply, tubers have been collected in destructive manner resulting in reduced plant population and pushing the plant in Red list of IUCN endangered species. However, manufacturers are using substitutes and other substandard drugs leading to adulteration which puts the importance of therapeutically rich herbal plants at stake. Lack of chemical markers is the main inability of regulatory authorities for not taking any action against this adulteration. Objective: Isolation of chemical marker of plant that can be used as a reference compound for identification of unauthorized substitution. Methods: Preliminary phytochemical screening of methanolic and toluene extract of H. intermedia D. Don was done using standard methods followed by column chromatography for the isolation of phytoconstituents. A total of 3004 fractions were collected with Thin Layer Chromatography (TLC) profiling and different fractions were pooled. A single compound was isolated and confirmed by chemical test, melting point, spectral analysis and compared with the literature. Results: Phytochemical screening of extracts shows the presence of alkaloids, carbohydrates, steroids, terpenoids, flavonoids, tannins and phenolics. A pure white crystalline powder was isolated by column chromatography which was characterized as 3,5-dimethoxy-4- hydroxycinnamic acid (Sinapic acid) with the help of IR and Mass spectroscopy. Conclusion: This is the first report of Sinapic acid as a novel compound from Vriddhi, Habenaria genus and Orchidaceae family. It can be used as a marker for the identification of unauthorized substitution and adulteration claiming the use of Vriddhi.

Lipid accumulation in white adipose tissue is the key contributor to the obesity and orchestrates numerous metabolic health problems such as type 2 diabetes, hypertension, atherosclerosis, and cancer. Nonetheless, the prevention and treatment of obesity are still inadequate. Recently, scientists found that brown adipose tissue (BAT) in adult humans has functions that are diametrically opposite to those of white adipose tissue and that BAT holds promise for a new strategy to counteract obesity. In this study, we evaluated the potential of sinapic acid (SA) to promote the thermogenic program and lipolysis in BAT. SA treatment of brown adipocytes induced the expression of brown-adipocyte activation-related genes such as Ucp1, Pgc-1α, and Prdm16. Furthermore, structural analysis and western blot revealed that SA upregulates protein kinase A (PKA) phosphorylation with competitive inhibition by a pan-PKA inhibitor, H89. SA binds to the adenosine triphosphate (ATP) site on the PKA catalytic subunit where H89 binds specifically. PKA-cat-α1 gene-silencing experiments confirmed that SA activates the thermogenic program via a mechanism involving PKA and cyclic AMP response element-binding protein (CREB) signaling. Moreover, SA treatment promoted lipolysis via a PKA/p38-mediated pathway. Our findings may allow us to open a new avenue of strategies against obesity and need further investigation. [BMB Reports 2020; 53(3): 142-147]

Microbial secondary metabolite discovery is often conducted in pure monocultures. In a natural setting, however, where metabolites are constantly exchanged, bio-synthetic precursors are likely provided by symbionts or hosts. In the current work, we report eight novel and architecturally unusual secondary metabolites synthesized by the bacterial symbiont Phaeobacter inhibens from precursors that, in a native context, would be provided by their algal hosts. Three of these were produced at low titres and their structures were determined de novo using the emerging microcrystal electron diffraction method. Some of the new metabolites exhibited potent algaecidal activity suggesting that the bacterial symbiont can convert algal precursors, tryptophan and sinapic acid, into complex cytotoxins. Our results have important implications for the parasitic phase of algal-bacterial symbiotic interactions.

Synthesis of copper oxide nanoparticles without any chemical reductant is always a challenging methodology for biological studies. In this study, sinapic acid, a phytochemical, is used for the synthesis of stable copper oxide nanoparticles. The as-synthesized nanoparticles were characterized thoroughly using UV-Visible, IR spectroscopy, Transmission Electron Microscopy (TEM) and X-ray photoelectron spectroscopy (XPS). Nanoparticles collected during different time intervals of synthesis (60,120 and 180 min) were subjected for analysis, where the occurrence of copper oxide nanoparticles with substantial morphology was seen at 180 min. Further, nanoparticles synthesized at 120 and 180 min were studied for their potential biological applications. These copper oxide nanoparticles evinced potential cytotoxic effects on breast cancer cells, MCF7 and MDA-MB231. Supplementarily, it also exhibited anti-angiogenic effect on endothelial cells (EA.hy926), thus confirming its potential to inhibit angiogenesis in cancer.

Sinapic acid (SinA) and corresponding esters are secondary metabolites abundantly found in plants of Brassica family. Belonging to the family of p-hydroxycinnamic acids, SinA and its esters analogues are present in different plant parts and involved in multiple biological processes in planta. Moreover, these metabolites are also found in relatively large quantities in agro-industrial wastes. Nowadays, these metabolites are increasingly drawing attention due to their bioactivities which include antioxidant, anti-microbial, anti-cancer and UV filtering activities. As a result, these metabolites find applications in pharmaceutical, cosmetic and food industries. In this context, this article reviews innate occurrence, biosynthesis, accessibility via chemical synthesis or direct extraction from agro-industrial wastes. Biological activities of SinA and its main corresponding esters will also be discussed.

SARS CoV-2 is still considered a global health issue, and its threat keeps growing with the emergence of newly evolved strains. Despite the success in developing some vaccines as a protective measure, finding cost-effective treatments is urgent. Accordingly, we screened a number of phenolic natural compounds for their in vitro anti-SARS CoV-2 activity. We found sinapic acid (SA) selectively inhibited the viral replication in vitro with an half-maximal inhibitory concentration (IC50) value of 2.69 µg/mL with significantly low cytotoxicity (CC50 = 189.3 µg/mL). Subsequently, we virtually screened all currently available molecular targets using a multistep in silico protocol to find out the most probable molecular target that mediates this compound’s antiviral activity. As a result, the viral envelope protein (E-protein) was suggested as the most possible hit for SA. Further in-depth molecular dynamic simulation-based investigation revealed the essential structural features of SA antiviral activity and its binding mode with E-protein. The structural and experimental results presented in this study strongly recommend SA as a promising structural motif for anti-SARS CoV-2 agent development.

Flax lignans (SDG) and sinapic acid (SA) both have the function of antioxidation and anti-inflammation. However, previous studies have focused mainly on biochemical measurements, gene expression analysis, and clinical assessments. There are limited studies that systematically reveal the underlying mechanism of the anti-inflammation effect of SDG or SA from the lipidomic point of view. Herein, the integrated lipidomic profiling platform was used for the analysis of free fatty acids (FFAs), phospholipids (PLs), triacylglycerols (TAGs), and oxylipins in high-fat (HF)-diet-fed mice after SDG or SA administration. Dietary supplementation of SDG or SA downregulated the levels of total TAGs and FFAs in the ApoE-/- mice model. Furthermore, 28 potential lipids were screened out and considered as key evaluation factors to understand the anti-inflammation function and mechanism of SDG and SA. The results indicated that the anti-inflammatory effect of SDG and SA was principally exerted via regulation of lipid homeostasis.

Objectives The aim of this research was to investigate whether sinapic acid (SA) can alleviate oxidative damage, apoptosis, and inflammation in I/R induced renal injury. Methods A total of 24 male rats were randomly separated into four groups as six rats in each group. Group 1 (Sham), Group 2 (I/R), Group 3 (I/R + SA, 10 mg/kg), Group 4 (I/R + SA, 20 mg/kg). In order to evaluate kidney function serum BUN, Cr, and AST were measured in an autoanalyzer. SOD, GSH-Px, MDA, PC and NO oxidative stress parameters were measured with spectrophotometric methods and TNF-α, IL-1β, IL-6, KIM-1 and NGAL parameters were measured with the ELISA method. In addition, H&E method and immunohistochemical examinations were performed for histological evaluations of kidney tissue. Results SA significantly decreases the increase in kidney damage, inflammation, oxidative stress, cell death and restore the decrease in antioxidant enzyme activities (p Conclusions The development of oxidative stress and lipid peroxidation seems to be the leading factors that accelerate inflammation and cell death during renal IRI. The antioxidant, anti-inflammatory, and anti-apoptotic features of SA displayed a renoprotective effect.

In 2021, Hawaii will permanently ban the use and sale of octinoxate-based sunscreens as studies have shown serious impacts of such UV filters on the coral reef. This ban, which could be generalized to other countries, highlights the extreme need to offer alternative UV filters that are not only effective in terms of sun protection, but also healthy with regards to human health and the environment. In this context, a wide library of p-hydroxycinnamic esters deriving from naturally occurring sinapic acid has been synthesized using a Knoevenagel&ndash, Doebner condensation. The UV filtering activities as well as the antioxidant properties of these sinapic acid esters were then investigated. The results showed promising UVB protection and antioxidant efficacy. A Structure&ndash, Activity Relationship (SAR) study on the sinapic acid esters highlighted the need of a free phenol to, as expected, observe antioxidant activity, but also to obtain a higher intensity of protection. Moreover, the nature of the ester moiety also proved to be a key structural feature for the UV absorbance, as higher steric hindrance on the ester moiety leads to more active compounds. The judicious structural design of sinapic esters thus provides promising compounds combining UV protection and antioxidant activity.

The secondary metabolome of the representative Roseobacter, Phaeobacter inhibens, was examined in response to algal sinapic acid. In addition to roseobacticides, sinapic acid induced the production of two new natural products, roseochelin A and B, which were characterized by NMR and X-ray crystallography. Functional assays showed that roseochelin B binds iron and is algaecidal against the algal host Emiliania huxleyi. It appears to be produced by a rarely observed combination of nonenzymatic and enzymatic transformations.

Cardiovascular diseases are one of the most common complications of type 2 diabetes. They are considered the leading cause of death among diabetics. One of the mechanisms underlying diabetic cardiovascular complications is oxidative stress. Many phenolic acids are regarded as antioxidants. The aim of the study was to investigate the effect of rosmarinic acid (RA) and sinapic acid (SA) on oxidative stress parameters in the cardiac tissue and serum of type 2 diabetic female rats. Additionally, the effect of these compounds on glucose homeostasis and lipid profile in the serum was evaluated. Type 2 diabetes was induced with high-fat diet and streptozotocin. RA at the doses of 10 and 50 mg/kg and SA at the doses of 5 and 25 mg/kg were administrated orally for 28 days. Untreated diabetic rats exhibited unfavorable changes in glucose metabolism and lipid profile. Changes in the enzymatic and non-enzymatic markers indicated the onset of oxidative stress in these animals. The results showed that the higher doses of the tested phenolic acids&mdash, 50 mg/kg of RA and 25 mg/kg of SA&mdash, revealed beneficial effects on oxidative stress in the cardiac tissue of diabetic rats.

Phenolic compounds, a group of plant metabolites, are of considerable interest because of their antioxidant pro-perties. Sinapic acid, a phenolic compound, is widely distributed in various fruits and vegetables. It is suggested to show some pharmacological effects such as antioxidant, antimicrobial, and anticancer. However, there is not eno-ugh data about the cytotoxicity of sinapic acid; the available data are limited. This study was aimed to assess the cytotoxic profiles of sinapic acid in a wide range of concentrations for 18 h exposure in two different cell lines, Chi-nese hamster lung fibroblasts (V79) and human cervical carcinoma (HeLa) cells using Neutral Red Uptake assay. The concentrations up to 500 μM and 2000 μM had no significant effect on V79 and HeLa cells, respectively, but the cell viabilities decreased below 50 % at concentrations higher than 1000 μM and 5000 μM for V79 and HeLa cells, res-pectively. IC50 values were found to be 1860 μM and 7248 μM in V79 and HeLa cells, respectively. This study has shown that sinapic acid have no cytotoxic effects in two different cell lines except at very high concentrations

Sinapic acid (SA) is a naturally occurring phenolic compound with antioxidant properties. It also has a wide range of pharmacological properties, such as anti-inflammatory, anticancer, and hepatoprotective properties. The present study aimed to evaluate the potential pharmacological effects of SA against hypertrophic responses in neonatal rat cardiomyocytes. In order to evaluate the preventive effect of SA on cardiac hypertrophy, phenylephrine (PE)-induced hypertrophic cardiomyocytes were treated with subcytotoxic concentrations of SA. SA effectively suppressed hypertrophic responses, such as cell size enlargement, sarcomeric rearrangement, and fetal gene re-expression. In addition, SA significantly inhibited the expression of mitogen-activated protein kinase (MAPK) proteins as pro-hypertrophic factors and protected the mitochondrial functions from hypertrophic stimuli. Notably, SA activated Sirt3, a mitochondrial deacetylase, and SOD2, a mitochondrial antioxidant, in hypertrophic cardiomyocytes. SA also inhibited oxidative stress in hypertrophic cardiomyocytes. However, the protective effect of SA was significantly reduced in Sirt3-silenced hypertrophic cardiomyocytes, indicating that SA exerts its beneficial effect through Sirt3/SOD signaling. In summary, this is the first study to reveal the potential pharmacological action and inhibitory mechanism of SA as an antioxidant against cardiac hypertrophy, suggesting that SA could be utilized for the treatment of cardiac hypertrophy.

As an approach to search for chemopreventive agents, we tested p-coumaric acid, 3-methoxy-p-coumaric acid (ferulic acid), and 3,5-dimethoxy-p-coumaric acid (sinapic acid) in B16/F10 melanoma cells. Intracellular melanin contents were determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay and cytotoxicity of the compounds were examined by lactate dehydrogenase (LDH) release. p-Coumaric acid showed inhibitory effect on melanogenesis, but ferulic acid increased melanin content, and sinapic acid had almost no effect on melanogenesis. Treatment with ferulic acid resulted in a 2 to 3 fold elevation in the production of melanin. Correlatively, cell viability decreased in a dose-dependent manner when treated with ferulic acid. However, ferulic acid did not affect the LDH release from the cells. Treatment with sinapic acid resulted in a 50∼60% elevation in the release of LDH when treated with a 200 μg/mL concentration and showed neither cytostasis nor increase of melanin synthesis in a dose-dependent manner. Taken together, p-coumaric acid inhibits melanogenesis, ferulic acid induces melanogenesis, and sinapic acid exerts cytotoxic effects in B16/F10 murine melanoma cells. The results indicate that the addition of methoxy groups to p-coumaric acid shows the melanogenic or cytotoxic effects in melanoma cells compared to the original compound. Therefore, this study suggests the possibility that methoxylated p-coumaric acid, ferulic acid can be used as a chemopreventive agent.

According to WHO, cancer is a leading cause of death worldwide, accounting for 8.2 million deaths in 2012. Among several factors involved in the pathogenesis of cancer, free radical formation followed by damage to DNA and cell protein is one of the causes. Natural plant products have gained enormous interest in the prevention or treatment of chronic diseases. Ferulic acid, like other phenolic acids (caffeic acid, sinapic acid) possess anti cancer activity. A series of ferulic esters (FE1 - FE11) and ferulic amides (FA1 - FA10) were synthesized and evaluated for their cytotoxic activity.

Hepatocellular carcinoma is one of the most common malignancies in worldwide. Sinapic acid (SA) is a phytochemical found in various fruits and vegetables. The aim of the study was to investigate the effect of SA on apoptosis in Hep3B and HepG2 hepatocellular carcinoma cells. XTT assay was used to determine the cytotoxic effect of SA. Total RNA isolation was conducted using TRIzol Reagent. Relative mRNA expression levels of important genes in apoptosis including CASP3, CASP7, CASP8, CASP9, BAX, BCL2, FAS and CYCS were quantified using qPCR in control and dose groups. The IC50 dose of SA in Hep3B and HepG2 cells were found to be 1000 µM and 1150 µM for 72 h, respectively. According to qPCR results, significant increases in the expressions of CASP3 and FAS were determined as 23.37 and 27.47 folds in treated Hep3B cells. On the other hand, SA in HepG2 cells caused a significant increase in the expressions of CASP3, CASP8, CASP9, BAX and FAS as 1.53, 1.77, 1.21, 1.47 and 1.39 folds respectively, compared with the control group. It is considered that SA may cause apoptosis in Hep3B and HepG2 cells. Further studies with SA should be conducted to can be therapeutic agent on hepatocellular carcinoma.

Plant-derived compounds for reducing the mycotoxin load in food and feed have become a rapidly developing research field of importance for plant breeding efforts and in the search for natural fungicides. In this study, toxigenic strains of Fusarium culmorum and F. graminearum sensu stricto were exposed to sinapic acid on solid YES media at levels close to those reported in wheat bran. Fusaria produced phenolic acids, whose accumulation was decreased by exogenous sinapic acid. Strains exposed to the lowest doses of sinapic acid showed more efficient reduction of phenolic acid production than fungi kept at higher concentrations of this compound. Fungi reduced exogenous sinapic acid, leading to the formation of syringic aldehyde. Treatment with sinapic acid led to a dramatic accumulation of its parent compound ferulic acid, presumably due to inhibition of the further conversion of this phenolic compound. Exogenous sinapic acid decreased the production of trichothecenes by fungi. Higher doses of sinapic acid resulted in more efficient reduction of mycotoxin accumulation in the media. Gene expression studies of Tri genes responsible for trichothecene biosynthesis (Tri4, Tri5 and Tri10) proved that the inhibition of mycotoxin production by sinapic acid occurred at the transcriptional level. Fusaria respond to sinapic acid by stimulation of ergosterol biosynthesis.

Scolymus hispanicus or the Golden Thistle, locally known as ‘Guernina’ or ‘Taghediwt’, is one of the most appreciated wild vegetables in Morocco. This study aims to characterise the functional chemical and pharmacological variability of Scolymus hispanicus parts (roots, stems, leaves and flowers). The chemical analysis revealed higher content of α-tocopherol in the flowers (2.79 ± 0.07 mg/100 g) and lead to the identification of 3 flavonoids and 13 phenolic acids, with high content of gallic acid in leaves (187.01 ± 10.19 mg/kg); chlorogenic (936.18 ± 92.66 mg/kg) and caffeic (4400.14 ± 191.43 mg/kg) acids in flowers, roots were much more higher in sinapic acid (0.25 ± 0.03 mg/kg) compared to the other parts. Moreover, Scolymus hispanicus ethanolic extracts exhibited interesting antioxidant and antimicrobial properties, promising anti-amylase and anti-glucosidase activities and relevant diuretic effect that confirms its traditional uses.

WOS: 000392591100021, PubMed ID: 28111996, Aldose reductase (AR) inhibitors have vital importance in the treatment and prevention of diabetic complications. In this study, rat kidney AR was purified 19.34-fold with a yield of 3.49% and a specific activity of 0.88 U/mg using DE-52 Cellulose anion exchange chromatography, gel filtration chromatography and 2'5' ADP Sepharose-4B affinity chromatography, respectively. After purification, the in vitro inhibition effects of some phenolic acids (tannic acid, chlorogenic acid, sinapic acid, protocatechuic acid, 4-hydroxybenzoic acid, p-coumaric acid, ferulic acid, vanillic acid, syringic acid, alpha-resorcylic acid, 3-hydroxybenzoic acid and gallic acid) were investigated on purified enzyme. We determined IC50, K-i values and inhibition types of these phenolic acids. As a result, tannic and chlorogenic acid had a strong inhibition effect. On the other hand, gallic acid had a weak inhibition effect. In this study, all phenolic acids except for chlorogenic acid and p-coumaric acid showed non-competitive inhibition effects on rat kidney AR.

Köpeklerde kemik kanserinin oluşumu hakkında ve olası sinyal yolakları ile ilgili çeşitli çalışmalar gün geçtikçe artmakta ve yeni tedavi yöntemleri aranmaktadır. Bu çalışmada, D17 kemik kanseri hücre hattında çeşitli besinlerde fenolik bir bileşik olarak bulunan sinapik asitin (SA) hücre döngüsü, sinyal iletimi ve apoptoz yolaklarında gen ekspresyonları üzerine etkilerinin araştırılması hedeflenmiştir. Ekspresyon düzeyinin araştırılmasından önce uygun SA dozunu bulmak için XTT yöntemi ile SA'in hücre canlılığına etkisi belirlenmiştir. IC50 dozu D17 hücre hattında 72. saatte 750 μM olarak saptanmıştır. Ardından, tamamlayıcı DNA'nın (cDNA) sentezi için Transkriptor First Strand cDNA Sentez Kiti (Roche Diagnostics) kullanılarak çalışmalar yürütülmüştür.Sinapik asitin, D17 hücre hattında apoptoz yolaklarındaki gen ekspresyonu üzerine etkileri gerçek zamanlı kantitatif PZR (qPZR) ile analiz edilmiştir. Analiz sonucunda nörogenez biyobelirteçleri olan BAX, BCL2, CASP3, CASP7, CASP8, CASP9, CYCS, FAS ve P53 genlerinin ekspresyonları çalışılmıştır. Ayrıca internal kontrol ve referans gen olarak RPL32 ve YWHAZ genleri kullanılmıştır. BAX, CASP3, CASP7, CASP8, CASP9, FAS ve P53 genlerindeki ekspresyon artışlarının istatistiksel olarak anlamlı (p

International audience; Rapeseed meal is a cheap and abundant raw material, particularly rich in phenolic compounds of biotechnological interest. In this study, we developed a two-step bioconversion process of naturally occurring sinapic acid (4-hydroxy-3,5-dimethoxycinnamic acid) from rapeseed meal into canolol by combining the complementary potentialities of two filamentous fungi, the micromycete Aspergillus niger and the basidiomycete Neolentinus lepideus. Canolol could display numerous industrial applications because of its high antioxidant, antimutagenic and anticarcinogenic properties. In the first step of the process, the use of the enzyme feruloyl esterase type-A (named AnFaeA) produced with the recombinant strain A. niger BRFM451 made it possible to release free sinapic acid from the raw meal by hydrolysing the conjugated forms of sinapic acid in the meal (mainly sinapine and glucopyranosyl sinapate). An amount of 39 nkat AnFaeA per gram of raw meal, at 55 °C and pH 5, led to the recovery of 6.6 to 7.4 mg of free sinapic acid per gram raw meal, which corresponded to a global hydrolysis yield of 68 to 76% and a 100% hydrolysis of sinapine. Then, the XAD2 adsorbent (a styrene and divinylbenzene copolymer resin), used at pH 4, enabled the efficient recovery of the released sinapic acid, and its concentration after elution with ethanol. In the second step, 3-day-old submerged cultures of the strain N.lepideus BRFM15 were supplied with the recovered sinapic acid as the substrate of bioconversion into canolol by a non-oxidative decarboxylation pathway. Canolol production reached 1.3 g/L with a molar yield of bioconversion of 80% and a productivity of 100 mg/L day. The same XAD2 resin, when used at pH 7, allowed the recovery and purification of canolol from the culture broth of N. lepideus. The two-step process used mild conditions compatible with green chemistry.

Acylated anthocyanins from the red-purple flowers of Arabis blepharophylla 1: pigment 1, R 1 = H, trans , R 2 = malonic acid 2: pigment 2, R 1 = OCH 3 , trans , R 2 = malonic acid 3: pigment 3, R 1 = H, cis , R 2 = malonic acid 4: pigment 4, R 1 = H, trans , R 2 = H 5: pigment 5, R 1 = OCH 3 , trans , R 2 = H. Figure options Download full-size image Download as PowerPoint slide

Two new acylated anthocyanins were isolated from beninabana, Brassica campestris var. chinensis, in addition to two known anthocyanins. The structures were established by spectral analyses.

Microwave treatment is a new method for rapeseed processing. To better understand the benefits of microwave pretreatment on rapeseed processing, qualitative and quantitative analysis of sinapic acid derivatives is needed. In this study, the effect of microwave treatment on the content of sinapic acid derivatives in rapeseed and the effect of cold-press and solvent extraction on the content of sinapic acid derivatives in rapeseed meal were evaluated using ultrahigh pressure liquid chromatography. It was found that during the microwave treatment, the content of sinapine and sinapic acid in the rapeseed increased slightly at the outset of treatment and significantly decreased thereafter. Following 7 min of microwave treatment, the content of sinapine in rapeseed exhibited its largest decrease of 16.7 %. By contrast, microwave heating of the rapeseed increased the canolol content significantly. We employed two sample paired t tests as a means to analyze the difference between meal and defatted cold-pressed cake. The results indicated that the content of sinapine and sinapic acid in defatted cake was significantly higher than that in meal, while the different extraction methods (solvent extraction and cold-press) did not appear to have a significant influence on the content of canolol in meal (p ≤ 0.05).

Consumption of whole-wheat products, including whole-wheat spaghetti, is associated with beneficial health effects. Flavonoids and lignans are antioxidant phytochemicals that have received much attention from researchers. Investigations were conducted on the content of flavonoid glycosides, lignan diglucoside, and secoisolariciresinol diglucoside (SDG) as contributors to the health-promoting properties of whole-wheat spaghetti. Flavonoid glycosides present in regular and whole-wheat spaghetti samples were identified as 6-C-glucosyl-8-C-arabinosyl apigenin and the sinapic acid ester of apigenin-C-diglycoside while, in a previous study, the sinapic acid ester of apigenin-C-diglycoside was found only in wheat germ tissues. The content of these compounds was significantly higher in whole-wheat spaghetti (17.0 and 15.1 μg of apigenin equivalent/g) compared to the regular brands (9.5 and 5.8 μg apigenin equivalent/g). SDG content was also significantly higher in whole-wheat spaghetti (41.8 μg/g) compar...

De-oiled rapeseed is a rich source of proteins and phenolic compounds. The phenolic compounds, namely sinapic acid derivatives (SAD), could occur as free sinapic acid, esterified (as sinapine, the choline ester of sinapic acid) and decarboxylated (as canolol) forms. Rapeseed protein preparations containing very low phenolic compounds have been the focus of our ongoing research. A precipitated rapeseed protein isolate is investigated for SAD such as sinapine, sinapoyl glucose, canolol using HPLC–DAD and LC–MS. Profile of the phenolic compounds of de-oiled rapeseed, press cakes and the precipitated protein isolate are compared. HPLC–DAD analysis indicated SAD; particularly sinapine is the main phenolic compound of all the substrates. The protein derivation process did not remarkably alter the profile of the investigated protein isolate.

As a part of our research project on the elucidation of the chain-breaking antioxidation mechanism for natural phenols in food components, the antioxidation products from a sinapic acid methyl ester in lipid oxidation were identified. Sinapic acid is a potent antioxidative phenolic acid widely distributed in edible plants. The structural determination of the four isolated products revealed them each to have a tricyclic structure consisting of ethyl linoleate, methyl sinapate and molecular oxygen, and these were isomeric compounds for the substituents on the tricyclic moiety.

From the lees of bokbunja wine (LBW) made from Rubus coreanus Miquel, we have identified six compounds (1: trans-4-hydroxycinnamic acid; 2: trans-4-hydroxy-3-methoxycinnamic acid; 3: 3,4-dihydroxycinnamic acid; 4: 4-hydroxy-3-methoxybenzoic acid; 5: 3,5-dimethoxy-4- hydroxybenzoic acid; and 6: 3,5-dimethoxy-4-hydroxycinnamic acid (sinapic acid)) through silica gel chromatography and UHPLC-MS. The compounds 1-6 showed strong anticoagulation and platelet aggregation inhibitory activities without hemolytic effect against human red blood cells. To date, this is the first report of the in vitro anti-thrombosis activity of sinapic acid. Our results suggest that different cinnamic and benzoic acid derivatives are closely linked to the anti-thrombosis activity of LBW, and sinapic acid could be developed as a promising anti-thrombosis agent.

Shanxi aged vinegar (SAV) is the most famous one among the four typical famous vinegars in China, which is produced by spontaneous solid-state fermentation using sorghum, bran, and millet chaff and Daqu. In this study, free phenolic acids (FPAs) species and changes during SAV aging, and the synergistic antioxidant activities between FPAs was investigated. The results revealed that eight FPAs, including protocatechuic acid, p-hydroxybenzoic acid, salicylic acid, dihydro sinapic acid, p-coumaric acid, sinapic acid, dihydro ferulic acid, and ferulic acid, stably existed during SAV 0–5 year aging periods, whereas during the aging time evaporation of water and FPAs combining with melanoidins made prediction of precise FPAs contents difficult. With regard to FPAs synergistic antioxidant activities, it was observed that the FPAs antioxidative interrelations were antagonism in antiradical activity experiments. And, only a few groups of FPAs mixtures showed antagonism in reduction experiments.

Two 8-8-coupled sinapic acid dehydrodimers and at least three sinapate-ferulate heterodimers have been identified as saponification products from different insoluble and soluble cereal grain dietary fibers. The two 8-8-disinapates were authenticated by comparison of their GC retention times and mass spectra with authentic dehydrodimers synthesized from methyl or ethyl sinapate using two different single-electron metal oxidant systems. The highest amounts (481 microg/g) were found in wild rice insoluble dietary fiber. Model reactions showed that it is unlikely that the dehydrodisinapates detected are artifacts formed from free sinapic acid during the saponification procedure. The dehydrodisinapates presumably derive from radical coupling of sinapate-polymer esters in the cell wall; the radical coupling origin is further confirmed by finding 8-8 and 8-5 (and possibly 8-O-4) sinapate-ferulate cross-products. Sinapates therefore appear to have an analogous role to ferulates in cross-linking polysaccharides in cereal grains and presumably grass cell walls in general.

Cancer is the most dangerous disease that causes deaths all over the world. Natural products have afforded a rich source of drugs in a number of therapeutic fields including anticancer agents. Many significant drugs have been derived from natural sources by structural optimization of natural products. Cinnamic acid has gained great interest due to its antiproliferative, antioxidant, antiangiogenic and antitumorigenic potency. Currently it has been observed that cinnamic acid and its analogs such as caffeic acid, sinapic acid, ferulic acid, and isoferulic acid display various pharmacological activities, such as immunomodulation, anti-inflammation, anticancer and antioxidant. They have served to be the major sources of potential leading anticancer compounds. In this review, we focus on the anticancer potency of cinnamic acid derivatives and novel strategies to design these derivatives. We hope this review will be useful for researchers who are interested in developing anticancer agents.

Ultraviolet spectroscopy of sinapoyl malate, an essential UV-B screening agent in plants, was carried out in the cold, isolated environment of a supersonic expansion to explore its intrinsic UV spectral properties in detail. Despite these conditions, sinapoyl malate displays anomalous spectral broadening extending well over 1000 cm(-1) in the UV-B region, presenting the tantalizing prospect that nature's selection of UV-B sunscreen is based in part on the inherent quantum mechanical features of its excited states. Jet-cooling provides an ideal setting in which to explore this topic, where complications from intermolecular interactions are eliminated. In order to better understand the structural causes of this behavior, the UV spectroscopy of a series of sinapate esters was undertaken and compared with ab initio calculations, starting with the simplest sinapate chromophore sinapic acid, and building up the ester side chain to sinapoyl malate. This "deconstruction" approach provided insight into the active mechanism intrinsic to sinapoyl malate, which is tentatively attributed to mixing of the bright V ((1)pp*) state with an adiabatically lower (1)np* state which, according to calculations, shows unique charge-transfer characteristics brought on by the electron-rich malate side chain. All members of the series absorb strongly in the UV-B region, but significant differences emerge in the appearance of the spectrum among the series, with derivatives most closely associated with sinapoyl malate showing characteristic broadening even under jet-cooled conditions. The long vibronic progressions, conformational distribution, and large oscillator strength of the V (pp*) transition in sinapates makes them ideal candidates for their role as UV-B screening agents in plants.

We have examined the antioxidant activity of the major phenolic compounds in Broccoli: two flavonol glycosides (quercetin 3-O-sophoroside and kaempferol 3-O-sophoroside) and four hydroxycinnamic acid esters (1,2'-disinapoyl-2-feruloyl gentiobiose, 1-sinapoyl-2-feruloyl gentiobiose, 1,2,2'-trisinapoyl gentiobiose and 1,2-disinapoyl gentiobiose). The Trolox C equivalent antioxidant capacity (TEAC) and inhibition of iron/ascorbate-induced lipid peroxidation of phosphatidyl choline vesicles were measured. In the aqueous phase TEAC assay, the two flavonol glycosides were less active than their respective aglycones. TEAC values for the hydroxycinnamic acid esters were less than the sum of their constituent hydroxycinnamic acids on a molar basis. Quercetin 3-O-sophoroside was a potent inhibitor of lipid peroxidation, in contrast to kaempferol 3-O-sophoroside. The hydroxycinnamic acid esters were highly effective at preventing lipid damage with the exception of 1,2,2'-trisinapoyl gentiobiose. The six compounds analysed herein demonstrate the antioxidant activity of the major phenolics in broccoli and indicate the effect on antioxidant activity of sugar substitutions in the phenolic B ring.

Brachypodium distachyon (Brachypodium) has been proposed as a model for grasses, but there is limited knowledge regarding its lignins and no data on lignin-related mutants. The cinnamyl alcohol dehydrogenase (CAD) genes involved in lignification are promising targets to improve the cellulose-to-ethanol conversion process. Down-regulation of CAD often induces a reddish coloration of lignified tissues. Based on this observation, we screened a chemically induced population of Brachypodium mutants (Bd21-3 background) for red culm coloration. We identified two mutants (Bd4179 and Bd7591), with mutations in the BdCAD1 gene. The mature stems of these mutants displayed reduced CAD activity and lower lignin content. Their lignins were enriched in 8-O-4- and 4-O-5-coupled sinapaldehyde units, as well as resistant inter-unit bonds and free phenolic groups. By contrast, there was no increase in coniferaldehyde end groups. Moreover, the amount of sinapic acid ester-linked to cell walls was measured for the first time in a lignin-related CAD grass mutant. Functional complementation of the Bd4179 mutant with the wild-type BdCAD1 allele restored the wild-type phenotype and lignification. Saccharification assays revealed that Bd4179 and Bd7591 lines were more susceptible to enzymatic hydrolysis than wild-type plants. Here, we have demonstrated that BdCAD1 is involved in lignification of Brachypodium. We have shown that a single nucleotide change in BdCAD1 reduces the lignin level and increases the degree of branching of lignins through incorporation of sinapaldehyde. These changes make saccharification of cells walls pre-treated with alkaline easier without compromising plant growth.

To stabilize the color and the antioxidant activity of black soybean anthocyanin, the potential of nanoencapsulation and copigmentation was investigated. Anthocyanin was copigmented with sinapic acid and nanoencapsulated by the ionic gelation method. The stability of anthocyanin in terms of color and antioxidant activity was significantly improved by both nanoencapsulation and copigmentation (P < 0.05). The nanoencapsulation was more efficient in improving the antioxidant activity and the color stability of Anthocyanin at high temperature. In addition, the highest stability of anthocyanin was observed in the copigmented anthocyanin-loaded nanoparticles, in which half-lives and retention were more than 2.6 and 7.4-fold greater than those of nonencapsulated anthocyanin. These results suggested that a combination of copigmentation and nanoencapsulation could be an effective technique for improving the color and antioxidant stability of anthocyanin. Practical Applications Although anthocyanin of black soybean has diverse health-promoting properties, such as antioxidant, anti-obesity, and hypolipidemic effects, few studies have been conducted with black soybean anthocyanin. In this manuscript, to stabilize the color and the antioxidant activity of black soybean anthocyanin, the potential of nanoencapsulation and copigmentation was investigated. The result suggests that a combination of copigmentation and nanoencapsulation could be useful for improving anthocyanin stability in terms of color and antioxidant activity. Therefore, this strategy for stability of black soybean anthocyanin could be practically employed in the food and nutrition industry because it can improve not only visual color but also biological activity of anthocyanin-related products.

The antioxidant capacity of 15 rapeseed varieties was determined by the proposed silver nanoparticle-based (AgNP) method and three modified assays: ferric reducing antioxidant power (FRAP), 2,2'-diphenyl-1-picrylhydrazyl (DPPH) and Folin-Ciocalteu reducing capacity (FC). The average antioxidant capacities of the studied rapeseed cultivars ranged between 5261-9462, 3708-7112, 18864-31245 and 5816-9937 μmol sinapic acid (SA)/100g for AgNP, FRAP, DPPH and FC methods, respectively. There are significant, positive correlations between antioxidant capacities of the studied rapeseed cultivars determined by four analytical methods (r=0.5971-0.9149, p0.05). The comparable precision for the proposed AgNP method (RSD=1.4-4.4%) and the modified FRAP, DPPH and FC methods (RSD=1.0-4.4%, 0.7-2.1% and 0.8-3.6%, respectively), demonstrate the benefit of the AgNP method in the routine analysis of antioxidant capacity of rapeseed cultivars. The principal component analysis (PCA) and hierarchical cluster analysis (HCA) were used for discrimination the quality of the studied rapeseed varieties based on their antioxidant potential determined by different analytical methods. Three main groups were identified by HCA, while the classification and characterisation of rapeseed varieties within each of these groups were obtained from PCA. The chemometric analyses demonstrated that, rapeseed variety S13 had the highest antioxidant capacity, thus this cultivar should be considered as the richest source of natural antioxidants.

A new sinapic acid ester, 6- O -β- d -(2′- O -sinapoyl)glucopyranosyl β- d -(1,2- O -disinapoyl)glucopyranose, was identified from fruits of Boreava orientalis . Structural elucidation was carried out on basis of UV, mass, 1 H and 13 C NMR spectral data, including 2D shift correlation and selective INEPT experiments.

Two sinapic acid conjugates and one phenolic glycoside were isolated from the roots of Cynanchum hancockianum . From spectroscopic evidence, the structures were characterized as 6- O -[ E ]-sinapoyl-(α- and β)- d -glucopyranoside, β- d -fructofuranosyl-α- d -(6- O -[ E ]-sinapoylglucopyranoside) and 2-acetylphenol-1-β- d -gluco- pyranosyl (1→6)-β- d -xylpyranoside. The latter two compounds are novel and were purified by preparation of their peracetylated derivatives.

[O-14CH3] Sinapic acid was synthesized with a specific activity of 54 mCi/mmol. Radiolabelled was carried out on methyl-3-(4-benzyloxy 3-hydroxy 5-methoxy phenyl) 2-propenoate with high yield, the deprotection of phenolic function and acid function are quantitative.