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Sinapic acid derivatives in defatted Oriental mustard (Brassica juncea L.) seed meal extracts using UHPLC-DAD-ESI-MSn and identification of compounds with antibacterial activity
Abstract
This study identified phenolic compounds from mustard seed meal and characterized their antibacterial activity. Phenolic compounds were extracted from defatted Oriental mustard (Brassica juncea L.) seed meal and characterized using ultra-high-performance liquid chromatography with diode array and electrospray ionization-mass spectrometric detection (UHPLC-DAD-ESI-MSn
). Sinapic acid and several sinapoyl conjugates were identified based on retention time, UV spectra, MS fragmentation pattern, and by comparison with the authentic sinapic acid reference substance. The crude extract and a purified phenolic fraction exhibited selective antibacterial effects against Gram-negative and Gram-positive spoilage bacteria including Staphylococcus aureus and Listeria monocytogenes; Lactobacillus plantarum was resistant. After alkaline hydrolysis, only sinapic acid could be detected, enabling quantification with the authentic reference substance. Alkaline hydrolysis released 2.66 ± 0.00 mg sinapic acid g−1 dry matter defatted mustard seed meal. Minimum inhibitory concentrations of the hydrolyzed extract against Bacillus subtilis, Escherichia coli, L. monocytogenes, Pseudomonas fluorescens, and S. aureus were 0.1 g L−1 or less. Growth of L. plantarum remained unaffected. Sinapic acid and sinapoyl esters are generally found in members of the Brassicaceae family. Methods for their fast identification will be useful in chemotaxonomic studies. The release of sinapic acid after alkaline hydrolysis not only allows for the quantification using the reference substances but also facilitates the standardization of the antibacterial activity of plant extracts for use as food preservative.
... Briefly, 1.5 g of dried material (DM) was placed in a 50 mL Erlenmeyer flask, which was then covered with a cotton plug, sterilized at 121°C for 15 min, cooled, and inoculated with a fungal suspension (10 7 spores/g DM) prepared in 0.9% saline solution at an adjusted pH of 3, 4, 5, 6, 7, or 8 to obtain a moisture content of 20, 30, 40, 50, 60, 70, 80, or 90%. The inoculated flasks were incubated at 24,27,30,33,36,39 or 42 o C for 2, 4, 5, 6, 7, 8, 9 or 10 days. The unfermented extract was prepared in the same manner as the fermented extract without the addition of fungi. ...
... Phenolic compounds with increased levels after fermentation may be the key contributor for the enhanced antibacterial activity of FAVRE since their antibacterial potential have been well documented. Specifically, these phenolic compounds, including ferulic acid [21,22], gallic acid [23,24], kaempferol [25,26] sinapic acid [27,28] and syringic acid [29,30], can inhibit both gram-positive and gram-negative bacteria and sensitize bacteria to antibiotics. In addition to phenolic compounds, other non-phenolic compounds in FAVRE may be responsible for the increased antibacterial activity. ...
... Regarding the phytochemical constituents that contribute to the disinfectant activity of FAVRE, an increase in the content of specific phenolic compounds, particularly ferulic acid, gallic acid, kaempferol, sinapic acid and syringic acid. may be an important contributor as the antibacterial activities of these compounds have previously been documented [22][23][24][25][26][27][28][29][30]. In general, phenolic compounds could modify the structure of the cell membrane, reduce the amount of lipids, and ultimately limit the growth and survival of microorganisms. ...
Purpose
The aim of the study was to identify the optimal conditions for the combined process, solid-state fermentation and maceration, for the highest recovery of polyphenols with disinfectant potency from aloe vera rind (AVR). After the process, the changes in phenolic compounds and the improvement of AVR extract in terms of antibacterial activity and surface disinfection efficiency and stability were determined.
Methods
Response surface methodology was used to optimize the process conditions. Phenolic compounds were determined by UHPLC-MS/MS. The fermented and unfermented extract was compared for the antibacterial activity along with disinfectant efficacy and stability, when being impregnated into wipes, against eight commonly infected pathogenic bacteria.
Results
Optimal fermentation and maceration conditions were identified, which were 5.7 days, 29.7oC, and 59.8% for fermentation time, temperature, and moisture content, respectively, and 45oC, 107.1 min, 71%, and 16.5 mL/g for maceration temperature and time, solvent concentration, and solvent/solid ratio, respectively. Under optimal conditions, the fermented extract had 294% higher total phenolic content, particularly higher levels of ferulic acid, gallic acid, kaempferol, sinapic acid and syringic acid, compared to the unfermented extract. In terms of antibacterial activity, the unfermented extract showed negligible anti-growth, anti-survival and anti-biofilm effects on all bacteria tested, in contrast to the significant effects of the fermented extract. In terms of disinfectant efficacy, the unfermented extract wipes showed no activity, whereas the fermented extract wipes reduced approximately 3–4 log numbers of tested bacteria both on the surface and in the wipes, and their surface disinfectant activity remained stable after six weeks.
Conclusion
Solid-state fermentation combined with maceration was demonstrated as a simple and cost-effective approach to enhance the disinfectant capacity and stability of AVR extract with prospective applications in ready-to-use disinfectant wipes.
... Extracts or simple chemical combinatorials can be more chemically stable and more effective than specific single chemical isolates [26,28,30] HPLC-UV-MS/MS methods are commonly used for detection and tentative identification of components in complex plant extracts. UV detection with a diode array detector coupled with electrospray ionization mass spectrometry (DAD-ESI-MS n ) in negative mode is a powerful tool for the analysis of phenolic compounds in botanical extracts, including extracts from Brassicaceae species [58]. In this study, the analysis parameters, such as the mobile phase gradient, UV detection wavelength and mass range, were optimized for efficient separation and detection of the phenylpropanoid constituents of broccoli extract. ...
... Several herein identified sinapic acid derivatives have been detected in other Brassicaceae plants, such as Brassica oleracea var. costata [59], Brassica napus [56,60,61] Brassica juncea [58] and Arabidopsis thaliana [15]. Sinapic acid and its esters are characteristic for the members of the Brassicaceae family. ...
... Sinapic acid and its esters are characteristic for the members of the Brassicaceae family. Sinapic acid is produced in the shikimate/phenylpropanoid pathway and then enzymatically converted into O-ester conjugates [58]. Sinapoyl-glucose (hexose) and sinapoyl malate are components of a well-known pathway of sinapate esters. ...
Background
Pain is a worldwide problem requiring an effective, affordable, non-addictive therapy. Using the edible plant broccoli, a growth protocol was developed to induce a concentrated combinatorial of potential anti-inflammatories in seedlings.
Methods
A growth method was utilized to produce a phenylpropanoid-rich broccoli sprout extract, referred to as Original Extract (OE). OE was concentrated and then resuspended for study of the effects on inflammation events. A rabbit disc model of inflammation and degeneration, and, a mouse model of pain behavior were used for in vivo and in vitro tests. To address aspects of mammalian metabolic processing, the OE was treated with the S9 liver microsome fraction derived from mouse, for use in a mouse in vivo study. Analytical chemistry was performed to identify major chemical species. Continuous variables were analyzed with a number of methods including ANOVA, and two-tailed t tests, as appropriate.
Results
In a rabbit spine (disc) injury model, inflammatory markers were reduced, and levels of regenerative markers were increased as a result of OE treatment, both in vivo and in vitro. In a mouse pain behavioral model, after treatment with S9 liver microsome fraction, the resultant extract significantly reduced early and late pain behavior in response to a pain stimulus. The OE itself reduced pain behavior in the mouse pain model, but did not achieve the level of significance observed for S9-treated extract. Analytical chemistry undertaken on the extract constituents revealed identities of the chemical species in OE, and how S9 liver microsome fraction treatment altered species identities and proportions.
Conclusions
In vitro and in vivo results indicate that the OE, and S9-treated OE broccoli extracts are worthwhile materials to develop a non-opiate inflammation and pain-reducing treatment.
... Natural phenolic acids have also been reported for their different biological activities, as represented in Table 1. Caffeic acid, which is a natural phenolic acid exhibits excellent antioxidant activity 7 and has been reported for its anti-inflammatory, antibacterial and anti-tumor activities 8 . Another natural cinnamic acid: sinapic acid extracted from mustard seeds, was tested against E. coli (Gramnegative) and S. aureus (Gram-positive) and found to exhibit antimicrobial activity 9 . ...
... The present study has reported the synthesis, antimicrobial and antioxidant activity of the synthesized derivatives of phenolic acids along with the preservative efficacy of ethyl 3, 4, 5trihydroxybenzoate, and propyl 3-(3,4dihydroxyphenyl) acrylate. 1 Vanillic acid Anti-cancer, Antimicrobial, Anti-tumor 3 2 Veratric acid Antitumor, Antihypertensive, Anti-inflammatory potential 14 3 Gallic acid Anti-bacterial 15 4 Syringic acid Anti-tumor, Anti-bacterial 16 6 Sinapic acid Antimicrobial, 12 7 Ferulic acid Anticancer, Antihypertension, Reducing type 2-diabetes 17 8 Coumaric acid Anticancer, Anti-inflammation, 18 9 Gentisic acid Anti-oxidant 19 10 Caffeic acid Anti-mutagenic and anticancer activity 20 11 Anisic acid Anti-fungal, Anti-bacterial 21 The reaction mixture was subjected to reflux on the water bath until the liberation of HCl gas was ceased, and the end of the reaction was confirmed with the appearance of single spot TLC. At the final stage, the ester was extracted with ether, and recrystallization was done with acetone. ...
Natural phenolic acids alkyl esters viz methyl, ethyl, propyl was synthesized and characterized by spectral means FTIR, 1HNMR, and 13CNMR. All the synthesized esters were examined for their antimicrobial potential, preservative efficacy and antioxidant potential. Among the synthesized ester derivative caffeic acid and gallic acid, derivatives were displayed excellent antioxidant and antimicrobial potential. They were further evaluated their preservative efficacy according to USP 2004 protocol for preservative effectiveness testing. Caffeic acid propyl ester and gallic acid ethyl ester exhibited promising preservative potential better than existing preservative agents. From the study, we can conclude that these caffeic and gallic acid derivatives can be used as lead compounds to further explore their application as preservative agents in pharmaceuticals and in the food industry.
... Sinapic acid showed selective antibacterial activity, inhibiting Gram-positive (S. aureus, Listeria monocytogenes) and Gram-negative bacteria (E. coli, P. fluorescens, Salmonella enterica), whereas Lactobacillus plantarum (G+) was not affected [41,42]. Such selective inhibition could be advantageous for using sinapic acid as food preservative to eliminate foodborne pathogens without affecting the growth of beneficial lactic acid bacteria, which are used as starter cultures, protective cultures, or probiotics [41,42]. ...
... coli, P. fluorescens, Salmonella enterica), whereas Lactobacillus plantarum (G+) was not affected [41,42]. Such selective inhibition could be advantageous for using sinapic acid as food preservative to eliminate foodborne pathogens without affecting the growth of beneficial lactic acid bacteria, which are used as starter cultures, protective cultures, or probiotics [41,42]. ...
Pseudomonas aeruginosa is one of the most antibiotic multi-resistant bacteria, causing chronic pulmonary disease and leading to respiratory failure and even mortality. Thus, there has been an ever-increasing search for novel and preferably natural antimicrobial compounds. Agrimonia eupatoria L. and Origanum vulgare L. shoots are commonly used as teas or alcoholic tinctures for their human health-promoting and antibacterial properties. Here, we explored the antimicrobial effects of all plant parts, i.e., leaf, flower, stem, and root extracts, prepared in water or in 60% ethanol, against P. aeruginosa. The impact of these extracts on bacterial survival was determined using a luminescent strain of P. aeruginosa, which emits light when alive. In addition, the antimicrobial effects were compared with the antioxidant properties and content of phenolic compounds of plant extracts. Ethanolic extracts of O. vulgare roots and flowers showed the highest antimicrobial activity, followed by A. eupatoria roots. In particular, chlorogenic acid, the ethanolic extract of O. vulgare roots contained high levels of protocatechuic acid, hesperidin, shikimic acid, rutin, quercetin, and morin. The synergistic effects of these phenolic compounds and flavonoids may play a key role in the antibacterial activity of teas and tinctures.
... The presence of the phenolic group in mustard mainly indicates the significant antioxidant, antifungal, and antibacterial effects. 26,27 The growth of S. rolfsii and R. solani was reduced while examined to assess the antifungal activity of mustard oil cake. 28,29 Samidurai et al. 30 reported that organic plantbased materials contain antifungal, antioxidant, and antibacterial effects which reduce the bacterial action while preserving raw hide/ skin. ...
Sodium chloride (NaCl), a globally used preserving agent, creates a large amount of chloride pollution known as salinity during soaking in the tannery. Increased salinity affects not only water quality but also the ecological balance. This study is focused on the minimization of sodium chloride (NaCl) use in goatskin preservation. The preliminary experiment revealed that a combination of 5% grounded mustard oil cake + 5% NaCl could be effective for the preservation of goatskin. Based on a preliminary experiment, the combination of preserving agents was applied on freshly flayed goatskin and assessed for 28 days considering parameters—moistness, Total Kjeldahl Nitrogen, hydroxyproline, microbial analysis, and hydrothermal stability. Gas chromatography–mass spectrometry (GC–MS) was performed with ethanol extract to identify the antimicrobial activity of mustard oil cake. The physicomechanical properties of produced leather were comparable to the standard requirements. Scanning electron microscope (SEM) images represented an intact form of a tanned collagen bundle. Pollution load of chloride content, biochemical oxygen demand (BOD), and chemical oxygen demand (COD) were reduced to 40.4%, 40.7%, and 48.4%, respectively, in soaking wastewater. Thus, a combination of mustard oil cake with the lower NaCl could be an eco‐friendly preservation technique to reduce pollution in the tannery wastewater.
... While the antibacterial activity of sinapic acid has been confirmed in various studies on plant and human pathogens [18], our results did not show a strong antimicrobial effect. Engels et al. [22] confirmed sinapic acid's antibacterial activity against multiple pathogens, including E. coli (MIC = 0.7 g/L). Liu et al. [23] attributed the limited efficacy of sinapic acid to its low solubility and its chemical structure. ...
Background:
The consumption of unpasteurized fruit juices poses a food safety risk due to the survival of pathogens such as Salmonella Enteritidis and Escherichia coli O157:H7.
Methods:
This study evaluated natural antimicrobials (nisin, coumaric acid, citral, sinapic acid, and vanillin) in orange juice as a strategy to ensure the control of these pathogens during the preservation of the non-thermally treated juices.
Results:
The addition of nisin, coumaric, or citral did not alter the juice's physicochemical characteristics, ensuring product quality. Nisin (1-2 mL/L), coumaric acid (0.25-0.5 g/L), and citral (0.25-0.5 mL/L) were the most effective in reducing bacterial populations. The antimicrobial activity of the most effective compounds was then tested against both acid-adapted and non-acid-adapted bacteria in refrigerated juice, applying Weibull and linear decay models to assess bacterial inactivation. Non-acid-adapted S. Enteritidis showed a rapid 5 log reduction after 30 h of refrigeration with the highest nisin dose, while the acid-adapted strain exhibited a smaller reduction (2 and 1.5 log units for 1 and 2 mL/L, respectively). Citral was effective but excluded due to solubility and aroma concerns. Non-acid-adapted E. coli O157:H7 showed a 5 log reduction with coumaric acid at 0.5 g/L, whereas acid-adapted strains exhibited a lower reduction (around 1.5 log units). Nisin and coumaric acid also reduced bacterial survival in gastrointestinal tract simulations. However, acid-adapted bacteria were more resistant.
Conclusions:
These findings highlight the potential of these antimicrobials for food safety applications, though further studies should explore their mechanisms and combinations for enhanced efficacy.
... The antibacterial activity present in this plant may be due to the presence of tannins and other phenolic constituents [62]. Engels et al. [63] indicate the inhibitory effect of sinapic acid against Gram-positive and Gram-negative bacteria. Bai et al. [64] demonstrated that quinic acid is capable of interacting with the cell membrane of S. aureus, leading to the dysfunction of oxidative phosphorylation, which favors the use of this acid as a potential antibacterial agent. ...
This work aimed to obtain a phytochemical extract from jambolan leaf using a hydroethanolic solvent and ultrasound-assisted extraction. For this purpose, an experimental design was applied to analyze the effect of process variables related to temperature (30–60 °C), time (10–30 min), and solvent to leaf ratio (5–15 mL g⁻¹), on the extraction mass yield (EMY) and on the yield of phenolic compounds (PCY). The effect of extractor solvent, AE (absolute ethanol), 75E (75% v·v⁻¹ ethanol) and 50E (50% v·v⁻¹), on the chemical characterization of the extracts, antidiabetic and antimicrobial activity, and cell viability, were also evaluated. The application of the highest values of process variables resulted in obtaining the maximum of the response variables (EMY = 9.94 wt% and PCY = 13.01 mg GAE g⁻¹ leaf). A higher content of phenolic compounds and flavonoids was obtained with 50E, which is mainly composed of sinapic, vanillic, trans-caffeic, and quinic acids, which were responsible for the greatest antioxidant potential, antibacterial activity (against Staphylococcus aureus and Pseudomonas aeruginosa), and inhibition of α-amylase. On the other hand, the use of AE allowed us to obtain extracts with higher concentrations of squalene, α-tocopherol, β-sitosterol, and friedelin. From cell viability tests, the extracts are not considered toxic at the concentration tested (100 µg mg⁻¹).
... Evaluating the activity of ferulic acid against the S. aureus CETC 976 strain, they demonstrated an MIC value of 1.1 mg/L (0.0057 mmol/L) [31]. In subsequent studies by Engels et al., an MIC value of 300 mg/L (1.34 mmol/L) was determined for sinapic acid against the S. aureus strain [32]. ...
Staphylococcus epidermidis, a component of human microbiota, may also cause life-threatening opportunistic infections. These are becoming increasingly common infections associated with the implantation of various implants. Due to the exhaustion of antibiotic resources, new substances with antimicrobial activity are being sought. The present study examined the antibacterial effect of cinnamic acid and its derivatives and their combinations with β-lactam antibiotics on the growth of Staphylococcus epidermidis strains isolated from vascular infections. The data obtained during the research indicated that cinnamic acid and its derivatives, sinapic acid, ferulic acid, and p-coumaric acid, have weak antibacterial activity (MIC values at the level of 2048 and 4096 mg/L). The combination of cinnamic acid and its derivatives with β-lactam antibiotics increases the effectiveness of their action and may demonstrate various pharmacological effects depending on the established cutoff.
... Its efficacy is purported to surpass that of ferulic acid [68], another hydroxycinnamic acid extensively utilized as a natural antioxidant in various food, beverage, and cosmetic products [69], and is comparable to caffeic acid [64,70,71]. Sinapic acid exhibits antimicrobial [72][73][74][75][76][77], anti-inflammatory [78], anticancer [79], and anti-anxiety properties [80]. ...
In this research, the chemical compositions of various extracts obtained from Ulva lactuca, a type of green seaweed collected from the Nador lagoon in the northern region of Morocco, were compared. Their antioxidant and anti-diabetic properties were also studied. Using GC–MS technology, the fatty acid content of the samples was analyzed, revealing that palmitic acid, eicosenoic acid, and linoleic acid were the most abundant unsaturated fatty acids present in all samples. The HPLC analysis indicated that sinapic acid, naringin, rutin, quercetin, cinnamic acid, salicylic acid, apigenin, flavone, and flavanone were the most prevalent phenolic compounds. The aqueous extract obtained by maceration showed high levels of polyphenols and flavonoids, with values of 379.67 ± 0.09 mg GAE/g and 212.11 ± 0.11 mg QE/g, respectively. This extract also exhibited an impressive ability to scavenge DPPH radicals, as indicated by its IC50 value of 0.095 ± 0.12 mg/mL. Additionally, the methanolic extract obtained using the Soxhlet method demonstrated antioxidant properties by preventing β-carotene discoloration, with an IC50 of 0.087 ± 0.14 mg/mL. Results from in-vitro studies showed that extracts from U. lactuca were able to significantly inhibit the enzymatic activity of α-amylase and α-glucosidase. Among the various extracts, methanolic extract (S) has been identified as the most potent inhibitor, exhibiting a statistically similar effect to that of acarbose. Furthermore, molecular docking models were used to evaluate the interaction between the primary phytochemicals found in these extracts and the human pancreatic α-amylase and α-glucosidase enzymes. These findings suggest that U. lactuca extracts contain bioactive substances that are capable of reducing enzyme activity more effectively than the commercially available drug, acarbose.
... Natural goods are increasingly being looked into as alternatives to conventional sanitizing agents in the washing processes for fresh produce. Essential oils (EOs) and hydrosols from aromatic plants are examples of natural plant extracts that are generally accepted as safe (GRAS) for use in the food industry and are also covered by EC Regulation No. 1334/2008 on flavorings and certain food ingredients with flavoring properties for use in and on foods [84,85]. Numerous EOs and other natural extracts, such as sage, Greek oregano, eucalyptus, and rosemary, have been used to preserve fresh produce and barely processed vegetables [86][87][88][89]. ...
The safety of vegetable food is compromised by various factors, including the inefficient or excessive use of sanitizers. Instances of individuals falling ill after consuming raw vegetables have been reported, with outbreaks of diseases caused by pathogens on fresh vegetables becoming increasingly prevalent globally, attracting significant media coverage and impacting the economic viability of vegetable cultivation. Measures to enhance food safety in postharvest horticultural produce involve controlling microbial proliferation and minimizing cross-contamination. Sanitizers were utilized in the food safety arsenal for a variety of purposes, including pathogen elimination and microbe reduction, hand, tool, and vegetable contact surface cleaning, and produce shelf-life extension. Choosing an appropriate sanitizer for all vegetables is difficult due to a lack of knowledge on which sanitizers are ideal for the many types of vegetables grown on farms under different environmental circumstances. Although chlorine-based sanitizers, such as sodium or calcium hypochlorite, have been widely used for the past 50 years, recent research has revealed that chlorine reacts with an organic compound in fresh vegetables to produce trihalomethane, a carcinogen precursor, and as a result, many countries have prohibited the use of chlorine in all foods. As a result, horticulture research groups worldwide are exploring non-chlorine, ecologically friendly sanitizers for the vegetable industry. They also want to understand more about the present procedures in the vegetable business for employing alternative sanitizers, as well as the efficacy and potential dangers to the food safety of fresh salad vegetables. This review paper presents detailed information on non-chlorine sanitizers, such as their efficacy, benefits, drawbacks, regulatory requirements, and the need for additional research to lower the risk of marketed salad vegetable food safety.
... Although the total concentration of polyphenols in the mustard seed meal was lower than in the other seed meal, the mustard meal polyphenolic extracts effectively suppressed the growth of E. coli suggesting that the efficiency was given by the individual compounds which have the ability to disrupt bacterial processes and inhibit their growth. Sinapic acid, for example, a prominent component among the polyphenols contained by mustard meal has been specifically highlighted for its inhibitory effects on the growth of E. coli (Engels et al. 2012). Additionally, 4-hydroxy-3-nitrophenylacetic acid derived from mustard seed meal exhibits significant antibacterial activity against E. coli. ...
Antibiotics and zinc oxide are therapeutic agents widely used in the livestock industries, reducing significantly the negative effects of weaning by improving the growth rate and decreasing mortality. Although, due to the potential public and environmental risks associated with antibiotic resistance and soil pollution their use in the E.U. has been drastically reduced or banned, thus, alternative solutions been necessary to be develop. The addition of polyphenols to animal feed has shown promising results, as they have a broad antimicrobial activity including against E. coli F4 (K88). Moreover, it has been observed to hold a wide range of beneficial properties such as antidiarrhoeic, anti-inflammatory, and antioxidant activity. In the present study in vitro experiments were performed in order to investigate the antimicrobial activity of several polyphenolic extracts obtained from mustard seed meals of two origins (Poland and Moldavia), grape seed meal, sea buckthorn seed meal, rapeseed meal, and rapeseed meal fermented with S. cerevisiae, against E. coli F4 (K88) proliferation measured at different intervals for 24 hours. The results revealed that polyphenols have a considerable antimicrobial effect in high concentrations. The inhibition was dependent also on polyphenol composition and even the origin place. Withal, it was observed that the polyphenols extracted from rapeseed meal and fermented rapeseed meal presented noticeable differences in inhibition, in similar concentrations, this suggesting that the fermentation process considerably affects the profile of rapeseed meal polyphenols. Likewise for the Moldavian mustard seed extract which significantly inhibited bacterial growth from very low concentrations although it had a low concentration of total polyphenols. Thus, the polyphenolic content of fermented rape seed meal extract presented an enhanced antimicrobial activity against E. coli F4 (K88) compared with the non-fermented rape seed meal extract. Although the total polyphenol concentration was lower in FRSM than in RSM. Polyphenols extracted from Moldavia mustard seed meal exhibited remarkable efficacy in inhibiting bacterial growth. Notably, even at a concentration as low as 3.71 µg/ml, the polyphenols demonstrated significant antimicrobial activity, effectively combating bacterial development. Overall, our study demonstrated that polyphenols represent a promising substitute for antibiotics and zinc oxide and might represent an encouraging long-term solution in overcoming the weaning crisis in pigs. In vivo experimentations are needed to validate these results.
... Furthermore, no variations in lowering E. coli O157: H7 and total coliforms in lettuce and spinach were discovered after washing with water and tannin solutions. (Engels et al. 2012). While washing spinach and lettuce samples in aqueous oregano extract for two minutes reduced E. coli O157:H7 counts by 2.1 log CFU g -1 and 3.7-4.0 ...
The safety of vegetable food is compromised by various factors, including the inefficient or excessive use of sanitizers. Instances of individuals falling ill after consuming raw vegetables have been reported, with outbreaks of diseases caused by pathogens on fresh vegetables becoming increasingly prevalent globally, attracting significant media coverage and impacting the economic viability of vegetable cultivation. Measures to enhance food safety in postharvest horticultural produce involve controlling microbial proliferation and minimizing cross-contamination. Sanitizers were utilized in the food safety arsenal for a variety of purposes, including pathogen elimination and microbe reduction, hand, tools, and vegetable contact surface cleaning, and produce shelf life extension. Choosing an appropriate sanitizer for all vegetables is difficult due to a lack of knowledge on which sanitizers are ideal for the many types of vegetables grown on farms under different environmental circumstances. Although chlorine-based sanitizers, such as sodium or calcium hypochlorite, have been widely used for the past 50 years, recent research has revealed that chlorine reacts with an organic compound in fresh vegetables to produce trihalomethane, a carcinogen precursor, and as a result, many countries have prohibited the use of chlorine in all foods. As a result, horticulture research groups worldwide are exploring for non-chlorine, ecologically friendly sanitizers for the vegetable industry. They also want to understand more about present procedures in the vegetable business for employing alternative sanitizers, as well as the efficacy and potential dangers to the food safety of fresh salad vegetables. This review-cum-research paper presented detailed information on non-chlorine sanitizers, such as their efficacy, benefits, drawbacks, regulatory requirements, and the need for additional research to lower the risk of marketed salad vegetable food safety.
... Sinapic acid (SA, 3,5-dimethoxy-4-hydroxycinnamic acid) is a naturally occurring hydroxycinnamic acid, found in plants, fruits, vegetables, several cereals, and oil crops [1][2][3][4] with potential use in food processing, cosmetics, and in the pharmaceutical industry. SA acts as an anti-inflammatory [5], antidiabetic [6], anticancer agent [7] with antioxidant [8], antibacterial [9], chemopreventive [10], neuroprotective [11], and antihypertensive [12] effects. ...
The thermal stability of bovine serum albumin (BSA) in Tris buffer, as well as the effect of sinapic acid (SA) on protein conformation were investigated via calorimetric (differential scanning microcalorimetry—μDSC), spectroscopic (dynamic light scattering—DLS; circular dichroism—CD), and molecular docking approaches. μDSC data revealed both the denaturation (endotherm) and aggregation (exotherm) of the protein, demonstrating the dual effect of SA on protein thermal stability. With an increase in ligand concentration, (i) protein denaturation shifts to a higher temperature (indicating native form stabilization), while (ii) the aggregation process shifts to a lower temperature (indicating enhanced reactivity of the denatured form). The stabilization effect of SA on the native structure of the protein was supported by CD results. High temperature (338 K) incubation induced protein unfolding and aggregation, and increasing the concentration of SA altered the size distribution of the protein population, as DLS measurements demonstrated. Complementary information offered by molecular docking allowed for the assessment of the ligand binding within the Sudlow’s site I of the protein. The deeper insight into the SA–BSA interaction offered by the present study may serve in the clarification of ligand pharmacokinetics and pharmacodynamics, thus opening paths for future research and therapeutic applications.
... However, using ClO2 to wash fresh products in gaseous and aqueous forms has benefits and drawbacks, which are listed in Table 4. Furthermore, no variations in lowering E. coli O157: H7 and total coliforms in lettuce and spinach were discovered after washing with water and tannin solutions. (Engels et al. 2012). While washing spinach and lettuce samples in aqueous oregano extract for two minutes reduced E. coli O157:H7 counts by 2.1 log CFU g -1 and 3.7-4.0 ...
Various reasons, including use, abuse, and excess using sanitizers ineffectively or at low doses, endanger vegetable food safety. People have become ill after eating raw vegetables, and pathogen-caused disease outbreaks on fresh vegetables have become more common worldwide, are widely covered in the media, and affect the profitability of producing vegetable crops. Postharvest horticultural produce environments can reduce food safety risks by limiting microbial development and preventing cross-contamination. In the food safety arsenal, sanitizers were used for various reasons, including eliminating pathogens and reducing lingering microorganisms, cleaning hands, tools, and vegetable contact surfaces, and extending produce shelf life. Choosing a suitable sanitizer for all vegetables is challenging because there is a lack of information on which sanitizers are best for the various types of vegetables grown on farms in various environmental conditions. Although chlorine-based sanitizers, such as sodium or calcium hypochlorite, have been widely used for the past 50 years, recent research has revealed that chlorine reacts with an organic compound in fresh vegetables to create trihalomethane, a carcinogen precursor, and thus, many countries have banned the use of chlorine in all foods. As a result, horticulture study groups worldwide are looking for non-chlorine and environmentally friendly sanitizers for the vegetable industry. They also want to learn more about the current practices for using alternative sanitizers in the vegetable industry and their efficacy and potential risks to the food safety of fresh salad vegetables. This review-cum-research paper provided comprehensive information on non-chlorine sanitizers, including their efficacy, benefits, drawbacks, regulatory requirements, and the need for additional research to reduce the risk of salad vegetable food safety.
... Aspergillus flavus was successfully combatted by hexane extract of plant seeds. 31 Aspergillus niger, Aspergillus flavus, Trichoderma viride, Candida albicans, Candida tropicalis, Cryptococcus neoformans, Trichosporon mucoides, Trichophyton tonsurans, and Geotrichum capitatum were all significantly inhibited by the oil from plant leaves when tested using the microbroth dilution and disc diffusion method. 32 When tested against Aspergillus flavus, Microsporum ferrogenium, and Mucormucaralis, the ethanolic extract of plant seeds exhibited a high zone of inhibition. ...
Since ancient times, many communities have employed plants to treat a wide range of illnesses, including infections. In underdeveloped and developed countries like, the aforementioned traditional plants serve a essential healthcare requirements. Plants' medicinal value is based on a number of secondary metabolites that are abundant in them and have pharmacological effects on the human body. Diverse products made from Brassica juncea have been used for a variety of medical purposes. Plant's seeds and the oils that can be extracted from them have been the focus of the majority of these historically recognized uses. The green edible leaves of this plant have also been described in more recent decades, and as a result, they are now frequently thought to be effective substitutes for other allegidly "healthy" Brassica vegetables. These green edible leaves contain a variety of bioactive molecules, as well as therapeutically intriguing pharmacological properties. The goal of this review is to summarize the molecular and scientific knowledge that is now available regarding Brassica juncea, including its phytochemical properties, pharmacological potential, and pharmacognostic traits. Data were acquired using Google, PubMed, Scholar, and other online venues
... B. rapa seeds showed that potential antimicrobial response against Salmonella paratyphi, Pseudomonas aeuriginosa, Staphylococcus aureus, Escherichia coli, and Klebsiella pneumonia (Muluye et al., 2015;Danlami et al., 2016). Researchers pointed out that Brassica species like radish root, kale leaves, and mustard seeds showed antimicrobial action against Bacillus subtilis, Staphylococcus aureus, Salmonella typhimurium, S. aureus, Enterobacter faecalis, Moraxella catarrhalis, Listeria monocytogenes and Escherichia coli (Ayaz et al., 2008;Beevi et al., 2009;Engels et al., 2012). ...
Brassicaceae familyare traditional, medicinal and nutritional value plants. Brassicaceae family produced valuable components to provide different types of beneficial effects for humans and animals such as anti-oxidant, antimicrobial, anticancer, anti-scurvy, anti-inflammatory, anti-hyperglycemic, anti-tumor, anti-diabetes, anti-stomach diseases, and anti-cardio, This review mainly focus to observe Brassicaceae family response in aquatic animalsandprovides some information collected from literature analysis regarding the development of aquaculture applications like Brassicaceae family plants used as a supplement to enhance nutritional value, replacement of fish meal, antimicrobial activity against pathogens, immunomodulatory effects, antioxidant, and growth activity of aquatic animals. This literature review analysis is helpful to enlighten for future research and development on the application in the aquaculture sector.
... TPC and TFC showed strong correlations with antioxidant capacities (DPPH and ABTS radical scavenging rates) in the control and red LED groups. Phenolic compounds, including cyanidin-3-glucoside, sinapine, and sinapic acid, also detected in this study, were reported to possess high antioxidant capacities [5,24,37]. Glucoraphenin and sulforaphene contents also strongly correlated with the antioxidant capacities in the control and red LED groups in this study, which was not directly investigated in the previous studies. Sulforaphane, a metabolite of glucoraphanin, a glucosinolate structurally similar to glucoraphenin, was reported to contribute to antioxidant capacities in broccoli in previous studies [8,11]. ...
Radish (Raphanus sativus) is one of the cruciferous vegetables containing high amounts of glucosinolates and phenolic compounds. The major glucosinolates in radish sprouts are glucoraphasatin and glucoraphenin. Glucoraphasatin can be converted to glucoraphenin and metabolized into sulforaphene, an isothiocyanate. This study aims to measure chemical compounds (total phenolics, flavonoids, glucoraphasatin, glucoraphenin, and sulforaphene) and bioactivities (antioxidant capacities and tyrosinase inhibitory effects) of extracts from radish sprouts exposed to red and blue LED during cultivation. On the fourth day of cultivation, total phenolic content (TPC), total flavonoid content (TFC), and glucoraphasatin content in radish sprout extracts (RSE) in the red LED group (TPC: 42.2 ± 2.01 mg gallic acid equivalent/g, dry weight) were significantly higher than those in the dark group (TFC: 1.71 ± 0.28 mg quercetin equivalent/g, dry weight; glucoraphasatin: 23.4 ± 7.76 mg/g, dry weight) (p < 0.05). ABTS free radical scavenging activities of the RSE in the red LED group were higher than those in the dark and blue LED groups on the fourth and seventh days of cultivation. On the seventh day of cultivation, in vitro tyrosinase inhibition rates of the RSE were the highest at concentrations of 0.5–1 mg/mL in the blue LED group. This study suggests that red LED exposure might promote the synthesis of glucoraphasatin during cultivation and contribute to high antioxidant capacities in radish sprouts. In addition, blue LED exposure might more efficiently promote the synthesis of substances possessing in vitro tyrosinase inhibitory effects of radish sprouts during cultivation.
... Commonly known as hydroxycinnamic acid, it includes p-coumaric acid (p-CoA), caffeic acid (CA), ferulic acid (FA), and sinapic acid (SA); (Natella et al. 1999;Teixeira et al. 2013;Neelam and Sharma 2020). A range of PPs and their derivatives have been illustrated to possess broad-spectrum antimicrobial activities (Engels et al. 2012;Khatkar et al. 2015;Lima et al. 2016) mainly due to their cell membrane damaging features (Hemaiswarya et al. 2011). Also, PPs possess strong antioxidant activity, primarily related to the presence of extended side-chain conjugation, hydroxyl function, and methoxyl group in their structure (Jia et al. 2018). ...
... 28,29 Sinapic acid derivatives, including sinapoyl malate, 1,2disinapoyldiglucoside, and 1,2-disinapoyl glucose are sinapate esters from canola seeds 30 and were identified by comparing with literature data. 31,32 Phenolic Compounds in Fermented and Uninoculated CM. Sinapic acid was the most abundant phenolic acid in free, conjugated, and bound fractions ( Table 4). ...
Canola meal (CM) is commonly used in poultry feeds. CM has a high protein content but also contains high levels of antimicrobial phenolic acids. Lactic acid bacteria can alter CM phenolic composition during fermentation and influence its antimicrobial activity against pathogens. Fermented CM was analyzed for phenolic composition using tandem mass spectrometry (LC-MS/MS) and high-performance liquid chromatography (HPLC). Sinapic acid and derivatives were the major phenolic acids in CM. Growth of lactobacilli in CM was attenuated when compared to cereal substrates. Glucosides and esters of sinapic acid were extensively hydrolyzed during fermentation with Lactiplantibacillus plantarum and Furfurilactobacillus milii. Lp. plantarum transformed hydroxycinnamic acids to dihydro, 4-vinyl, and 4-ethyl derivatives, Ff. milii reduced hydroxycinnamic acids to dihydroderivatives, but Limosilactobacillus reuteri did not convert hydroxycinnamic acids. The minimum inhibitory concentration of phenolic extracts was assessed with lactobacilli, Salmonella, and Campylobacter jejuni as indicator strains. Fermentation of CM with Lp. plantarum or Ff. milii increased the antimicrobial activity of phenolic extracts against Salmonella enterica and Campylobacter jejuni. Fermentation with Lm. reuteri TMW1.656 but not fermentation with Lm. reuteri TMW1.656ΔrtcN increased the antimicrobial activity of extracts owing to the production of reutericyclin. This study demonstrates that fermentation of CM with lactobacilli converts hydroxycinammic esters and may increase the antimicrobial activity of phenolic compounds in CM against pathogens.
... Sorghum and oats also contain glycerol esters of ferulic, p-coumaric and caffeic acid (Svensson et al., 2010;Varga et al., 2018). Phenolic acid glycosides are frequently found in sinapic acid rich flaxseed, canola, and mustard (Engels et al., 2012;Khattab et al., 2010). ...
Lactobacillaceae are among the major fermentation organisms in most food fermentations but the metabolic pathways for conversion of (poly)phenolic compounds by lactobacilli have been elucidated only in the past two decades. Hydroxycinnamic and hydroxybenzoic acids are metabolized by separate enzymes which include multiple esterases, decarboxylases and hydroxycinnamic acid reductases. Glycosides of phenolic compounds including flavonoids are metabolized by glycosidases, some of which are dedicated to glycosides of plant phytochemicals rather than oligosaccharides. Metabolism of phenolic compounds in food fermentations often differs from metabolism in vitro, likely reflecting the diversity of phenolic compounds and the unknown stimuli that induce expression of metabolic genes. Current knowledge will facilitate fermentation strategies to achieve improved food quality by targeted conversion of phenolic compounds.
... Hydroxycinnamic acid is a phenolic acid that contains bioactive carboxylic acids; examples include caffeic acid, ferulic acid, and sinapic acid (SA) [17][18][19]. SA is abundant in variety of plant sources, such as berry fruits, cereals, citrus, spices, oilseed crops, and vegetables [20]. SA has a molecular weight of 224.21 g/mol, and it is a yellow-brown crystalline powder [18]. ...
Sinapic acid (SA) is a poorly water-soluble substance which could result in poor bioavailability. The aim of this study was to determine the “hydroxypropyl β-cyclodextrin (HPβCD)” solubilization of SA in the presence of the auxiliary substance hydroxypropyl methylcellulose (HPMC) and to evaluate the ternary inclusion complex prepared by microwave technology. Phase-solubility profiles showed that HPβCD exhibited the greatest solubilizing effect on SA in the presence of HPMC. The enhanced rate of SA dissolution was exhibited by a ternary complex. Outcomes of analyses such as “DSC, FTIR, NMR, and SEM” confirmed the embedding of SA into the cavity of the HPβCD and the formation of a ternary inclusion complex. The outcomes of antioxidant activity (ABTS and nitric oxide scavenging activity) demonstrated that SA ternary inclusion complex (TIC) presented strong antioxidant activity, which might be a result of the enhanced solubility of SA in the TIC prepared by microwave technology. Hence, SA-TIC formulation could be a better dosage form which may protect the body from free radical damage and oxidative stress. Microwave technology greatly boosted the interaction of SA with HPβCD and HPMC, and such findings are expected to contribute to raising the solubility of SA, thereby improving the bioavailability of SA.
... The quantity of sinapic acid in B3 cultivar was much higher than other fruits and vegetable listed in Table 5. Currently, sinapic acid has already been evaluated for its various biological activities, such as antimicrobial [25], antioxidant [26], antiinflammatory [22], anticancer [27], and anti-anxiety activities [28]. In addition, this compound showed a protective effect over arsenic induced toxicity [29], and prevented lysosomal dysfunction in isoproterenol induced myocardial infarcted rats [30]. ...
The present study examined the correlation between phenolic acids and flavonoids with high rice yield traits of rice. It was observed that the difference of phenolic contents among the tested rice lines occurred only in the vegetative stage. The concentrations of phenolic acids were higher in the rice high yield cultivars than low yield variety in the vegetative stage, but they either decreased dramatically or disappeared during the development stage. Caffeic acid was found only in high yield rice, whereas chlorogenic acid was detected only in low yield rice. Sinapic acid was the dominant phenolic acid in high yield cultivars at vegetative stage (3.7 mg/g), followed by ferulic acid (1.2 mg/g). These findings suggest that caffeic acid, ferulic acid, sinapic acid and chlorogenic acid may play a particular role in forming yield components in rice. The cultivar B3 contained high amount of sinapic acid may be used as a natural source for pharmaceutical use.
... It is yellow-brown crystalline powder with the molecular weight of 224.21 g/mol [2]. It is a phytochemical that is present in various plant sources, such as berry fruits, cereals, citrus, oilseed crops, spices, and vegetables [4][5][6][7]. Previously, SA has shown activity against different conditions, such as oxidative stress [8], inflammation [9,10], anxiety [10], infections [11], diabetes [12], neurodegeneration [13], and cancer [14]. SA is a poorly soluble bioactive compound in water and, due to its limited dissolution rate, it restricts its permeability via the biological membranes, leading to decreased bioavailability [15][16][17]. ...
The goal of this study was to increase the aqueous solubility and dissolution rate of sinapic acid (SA) by formulating binary inclusion complex (BIC) of SA with hydroxypropyl-β-cyclodextrin (HPβCD) using solvent evaporation (SE) technology. The phase solubility and dissolution studies were conducted to determine the solubility and in vitro release rate of SA. In addition, the prepared inclusion complex was characterized for solid state characterization using techniques such as DSC, PXRD, SEM, and FTIR. Moreover, the prepared SA-BIC was evaluated for its antioxidant activity. Results revealed that the SA solubility can be shown to improve with a change in HPβCD concentration. About 2.59 times higher solubility of SA in water was noticed in the presence of HPβCD (10 mM). Dissolution study demonstrated that the 34.11 ± 4.51% of SA was released from binary physical mixture (BPM), while the maximum release of 46.27 ± 2.79% of SA was observed for SA-BIC prepared by SE method. The prepared SA-BIC demonstrated distinctive properties when compared to pure SA, which was demonstrated by different analytical methods, such as DSC, PXRD, SEM, and FTIR, as evidence of SA inclusion into HPβCD cavity. Further, it was observed that SA-BIC displayed stronger DPPH radical scavenging activity than SA. In conclusion, SE technology considerably enhanced the complexity of SA with HPβCD, and these observations could help to heighten the SA solubility, which may lead to a better bioavailability.
... Mustard seeds are characterized by the presence of secondary metabolites [79,80] mainly including phenolic compounds, GSLs, and omega-3 PUFAs that have attracted the attention of numerous researchers. Herein, we report their pharmacological potential highlighting the mechanisms of action. ...
Seeds from mustard (genera Brassica spp. and Sinapsis spp.), are known as a rich source of glucosinolates and omega-3 fatty acids. These compounds are widely known for their health benefits that include reducing inflammation and lowering the risk of cardiovascular diseases and cancer. This review presented a synthesis of published literature from Google Scholar, PubMed, Scopus, Sci Finder, and Web of Science regarding the different glucosinolates and omega-3 fatty acids isolated from mustard seeds. We presented an overview of extraction, isolation, purification, and structure elucidation of glucosinolates from the seeds of mustard plants. Moreover, we presented a compilation of in vitro, in vivo, and clinical studies showing the potential health benefits of glucosinolates and omega-3 fatty acids. Previous studies showed that glucosinolates have antimicrobial, antipain, and anticancer properties while omega-3 fatty acids are useful for their pharmacologic effects against sleep disorders, anxiety, cerebrovascular disease, neurodegenerative disease, hypercholesterolemia, and diabetes. Further studies are needed to investigate other naturally occurring glucosinolates and omega-3 fatty acids, improve and standardize the extraction and isolation methods from mustard seeds, and obtain more clinical evidence on the pharmacological applications of glucosinolates and omega-3 fatty acids from mustard seeds.
... Among foods that are good candidates for possible recycling and re-using, the Brassicaceae family including cauliflower, horseradish, and mustard seeds, represents a predominant class for the presence of nutritional components [2][3][4][5]. For instance, glucosinolates present in Brassicaceae samples are a large group of sulfur-containing secondary metabolites with anti-inflammatory and anti-cancer properties [6]. ...
The increasing demand for food and the need for a sustainability vision in the agri-food sector have boosted novel approaches for food management, enhancing the valorization of wastes and by-products belonging to the food industry. Herein, we present a novel paper-based origami device to assess the amount of both glucosinolate and glucose in a food waste product belonging to Brassicaceae plants, to evaluate the quality value and the correct management of waste samples. The device has been designed as an origami paper-based platform constituted of two paper-based biosensors to work synergistically in a multiplexed detection. In detail, a monoenzymatic biosensor and a bienzymatic biosensor were configured for the detection of glucose and glucosinolates, respectively, using filter paper pads preloaded with glucose oxidase and/or myrosinase. To complete the paper-based platform, the enzyme-preloaded pads were combined with office paper-based electrodes modified with Carbon black/Prussian Blue nanoparticles for the measurement of enzymatic by-product at a low applied potential (i.e., 0 V versus Ag/AgCl). Overall, this paper-based platform measured glucose and glucosinolate (i.e., sinigrin) with a linear range up to 2.5 and 1.5 mM, and detection limits of 0.05 and 0.07 mM, respectively. The repeatability corresponded to an RSD% equal to 5% by testing 10 mM of glucose, and 10% by testing 1 mM of sinigrin. The accuracy of the developed multiplex device was evaluated by recovery studies at two different levels of sinigrin, i.e., 0.25 and 0.5 mM, obtaining recoveries values equal to (111 ± 3) % and (86 ± 1) %, respectively. The multiplex detection of both glucose and glucosinolate in Brassicaceae samples evaluates the quality values of the waste sample, ensuring the quality of the re-used food product waste by using an eco-designed analytical tool. The combination of paper-based devices for quality control of food waste with the re-use of these food products represents a sustainable approach that perfectly matches sustainable agrifood practices as well as the overall approach of the circular economy.
Graphical abstract
Background
Diabetes mellitus (DM) is a major intricate metabolic disorder, being one of the chief causes of mortality worldwide. Coccoloba and Ruprechtia are two of the most intriguing polyphenol-rich genera within the Polygonaceae family. The potential of Coccoloba uvifera, Coccoloba peltata and Ruprechtia salicifolia total extracts and fractions as antioxidant, antidiabetic and anti-glycating agents was evaluated and correlated with their chemical composition via multiple approaches of metabolic profiling.
Results
All the total ethanolic extracts of plant leaves revealed remarkable antioxidant activities in terms of scavenging DPPH and ABTS radicals, as well as ferric reducing antioxidant power (FRAP). Despite having more or less comparable total phenolic and flavonoid contents, C. uvifera extract showed the highest inhibitory activity against α -glucosidase enzyme (IC 50 7.985 ± 1.08 μg/mL), being more potent than acarbose (20-fold). All total extracts demonstrated moderately high anti-AGEs (> 63% inhibition) in BSA-fructose model. Among all examined fractions, C. uvifera 50% MeOH fraction exhibited the most potent antioxidant activity in DPPH, ABTS and FRAP assays (5697.33 ± 360.7, 3078.9 ± 249, 1664.02 ± 220 µM ascorbic acid equivalent/mg extract, respectively) and the highest α -glucosidase inhibitory activity (IC 50 3.36 ± 1.04 μg/mL). A total of 140 compounds, belonging to different classes, were annotated in the three species via UPLC-HRMS, where flavonoids and phenolic acids represented the major classes. Multivariate and correlation analyses revealed the key phytochemicals contributing to α -glucosidase inhibition as 1- O -vanilloyl-hexoside, 1,3- O -diferuloylglycerol, drovomifoliol- O -glucopyranoside, protocatechuic acid glucoside, digalloyl glucose and coumaric acid sulphate.
Conclusion
C. uvifera leaves extract and its 50% MeOH fraction had a superb potential to alleviate DM and its complications through their antioxidant, antiglycation and α -glucosidase inhibitory activities mediated by their versatile polyphenolic phytochemicals.
Graphical abstract
Plant root exudates are involved in nutrient acquisition, microbial partnerships, and inter‐organism signaling. Yet, little is known about the genetic and environmental drivers of root exudate variation at large geographical scales, which may help understand the evolutionary trajectories of plants in heterogeneous environments.
We quantified natural variation in the chemical composition of Arabidopsis thaliana root exudates in 105 Iberian accessions. We identified up to 373 putative compounds using ultra‐high‐performance liquid chromatography coupled with mass spectrometry. We estimated the broad‐sense heritability of compounds and conducted a genome‐wide association (GWA) study. We associated variation in root exudates to variation in geographic, environmental, life history, and genetic attributes of Iberian accessions.
Only 25 of 373 compounds exhibited broad‐sense heritability values significantly different from zero. GWA analysis identified polymorphisms associated with 12 root exudate compounds and 26 known genes involved in metabolism, defense, signaling, and nutrient transport. The genetic structure influenced root exudate composition involving terpenoids. We detected five terpenoids related to plant defense significantly varying in mean abundances in two genetic clusters.
Our study provides first insights into the extent of root exudate natural variation at a regional scale depicting a diversified evolutionary trajectory among A. thaliana genetic clusters chiefly mediated by terpenoid composition.
The neuroprotective effects of polyphenols have been reported in the prevention of the early onset or delay of the progression of various neurodegenerative diseases, including Parkinson disease (PD). Neuroinflammation, oxidative stress, and mitochondrial dysfunction play significant roles in the pathophysiology of PD. Sinapic acid (SNP) is a naturally occurring polyphenol belonging to a group of hydroxycinnamic acids, which has gained importance owing to its beneficial effects, including antioxidant and anti-inflammatory properties. The present study aimed to develop an insight into the effects of sinapic acid on mitigating the inflammatory markers, oxidative stress, and deranged mitochondrial dynamics in human neuroblastoma cells (SHSY5Y) intoxicated with MPP ⁺ . The modulating variations of SNP on apoptosis, mitochondrial membrane potential (MMP), intracellular reactive oxygen species (ROS), and expression of proteins like PARKIN, PINK1, DJ-1, Bax, and BCl2 were analyzed in MPP+ induced PD-like toxic conditions. Pre-treatment with SNP decreased the levels of ROS and improved MMP. Also, SNP down-regulated the expression of PARKIN1, caspase-3, and DJ-1, along with a reduction in the expression of inflammatory markers such as IL-1β and TNF-α. Further, SNP was observed to increase the levels of BCl2, an anti-apoptotic protein, and the activity of superoxide dismutase (SOD), an enzymatic antioxidant. Based on the above results, the authors concluded that SNP exhibited neurotherapeutic potential in PD-like neurotoxic conditions. The present study reported the preclinical and mechanistic approach to identify the exact mechanism of action of SNP in PD.
Inflammation has been shown to trigger a wide range of chronic diseases, particularly inflammatory diseases. As a result, the focus of research has been on anti-inflammatory drugs and foods. In recent years, the field of medicinal and edible homology (MEH) has developed rapidly in both medical and food sciences, with 95% of MEH being associated with plants. Phenolic acids are a crucial group of natural bioactive substances found in medicinal and edible homologous plants (MEHPs). Their anti-inflammatory activity is significant as they play a vital role in treating several inflammatory diseases. These compounds possess enormous potential for developing anti-inflammatory drugs and functional foods. However, their development is far from satisfactory due to their diverse structure and intricate anti-inflammatory mechanisms. In this review, we summarize the various types, structures, and distribution of MEHP phenolic acids that have been identified as of 2023. We also analyze their anti-inflammatory activity and molecular mechanisms in inflammatory diseases through NF-κB, MAPK, NLRP3, Nrf2, TLRs, and IL-17 pathways. Additionally, we investigate their impact on regulating the composition of the gut microbiota and immune responses. This analysis lays the groundwork for further exploration of the anti-inflammatory structure-activity relationship of MEHP phenolic acids, aiming to inspire structural optimization and deepen our understanding of their mechanism, and provides valuable insights for future research and development in this field.
Sinapic acid (SA) is a potent nutraceutical or natural bioactive compound which is commonly present in the human diet. It was evaluated for its anti-inflammatory activity by in- vitro methods like albumin denaturation assay, heat induced and hypotonicity induced haemolysis, Cycloxygenase-2 (COX-2) and lipoxygenase (5-LOX) inhibition assay at different concentrations. Aspirin (200 μg/ml) and Indomethacin (100 μg/ml) were used as standard drugs. The results showed that Sinapic acid at a concentration range of 10-500 μg/ml significantly (P<0.001) protected the heat induced protein denaturation. Heat and hypotonicity induced haemolysis of erythrocyte was significantly (P<0.001) inhibited at the concentration of 500 μg/ml. The (COX-2) and (5-LOX) enzymes were significantly (P<0.001) inhibited by Sinapic acid. The results indicate that Sinapic acid may be a potential anti-inflammatory agent.
Sinapic acid (SA) is a bioactive phenolic acid; its diverse properties are its anti-inflammatory, antioxidant, anticancer, and antibacterial activities. The bioactive compound SA is poorly soluble in water. Our goal was to formulate SA-transethosomes using thin-film hydration. The prepared formulations were examined for various parameters. In addition, the optimized formulation was evaluated for surface morphology, in-vitro penetration studies across the Strat M®, and its antioxidant activity. The optimized formulation (F5) exhibited 74.36% entrapment efficacy. The vesicle size, zeta potential, and polydispersity index were found to be 111.67 nm, −7.253 mV, and 0.240, respectively. The surface morphology showed smooth and spherical vesicles of SA-transethosomes. In addition, the prepared SA-transethosomes exhibited enhanced antioxidant activity. The SA-transethosomes demonstrated considerably greater penetration across the Strat M® membrane during the study. The flux of SA and SA-transethosomes through the Strat M® membrane was 1.03 ± 0.07 µg/cm²/h and 2.93 ± 0.16 µg/cm²/h. The enhancement ratio of SA-transethosomes was 2.86 ± 0.35 compared to the control. The SA-transethosomes are flexible nano-sized vesicles and are able to penetrate the entrapped drug in a higher concentration. Hence, it was concluded that SA-transethosome-based approaches have the potential to be useful for accentuating the penetrability of SA across the skin.
Earlier, natural compounds and their structural analogs have significantly influenced pharmacology, particularly for the treatment of cancer and infectious disorders. However, natural products also pose difficulties for the development of new drugs, such as technological obstacles to screening, isolation, characterization, and optimization, which led to a drop in the pursuit of these substances. In this chapter, the therapeutic use of natural products and scaffold based on natural products have been discussed briefly.KeywordsDrugsScaffoldNatural products
Molecular target
Consumers have recently preferred food that is easy to make and of excellent quality, as well as food that is safe, natural, and minimally processed, but has a longer shelf life. Food deteriorates over time as a result of microbiological, chemical, or physical changes. Phytochemicals derived from medicinal and food plants have long been recognized for their biological activity to protect plants. These bioactivities are designed to increase the shelf life of food while inhibiting the growth of microorganisms. The use of natural plant food preservatives containing bioactive compounds as health-promoting agents is particularly intriguing. Furthermore, due to their effectiveness against food spoilage and foodborne pathogens, natural plant-origin antimicrobial compounds have been investigated as alternatives to synthetic antimicrobial compounds for preserving food quality. This review focused on the plant composition and properties that can be utilized as a natural food preservative, as well as the possibilities of using Mongolian medicinal plants.
Phenolic recovery from agricultural byproducts has been highlighted due to their health-promoting bioactivities. However, uncontrolled discard of residues after extraction process would induce environmental pollution and bioresource waste. In this study, biorefining of phenolic-rich rapeseed meal (RSM) and its defatted sample (dRSM) was attempted by holistic utilization of phenolic extract and residue separately. Phenolic removal could significantly improve residues' Cr(VI) adsorption capacities by about 21%, which presented extended physical surface and more released functional groups. Moreover, simulating raw material by remixing 3% separated phenolic extracts or main component sinapic acid therein with corresponding residues further improved about 12% adsorption efficiencies. These indicated that the different present forms of phenolics had opposite effects on Cr(VI) removal. While natural conjugational form inhibited hosts' biosorption, free form had enhanced functions for either extract or residue. Four optimal adsorption parameters (pH, adsorbent dosage, contact time and initial Cr(VI) concentration), three kinetic (pseudo-first order, pseudo-second order and intra-particle diffusion) models and two isotherms (Langmuir and Freundlich) were used to reveal the adsorption process. The maximum Cr(VI) adsorption capacity on residues could reach about 100 mg/g, which was superior to that of most biosorbents derived from agricultural byproducts, even some biochar. Together with the residues' advantages with everlasting capacity after 3 adsorption-desorption cycles and excellent abilities for adsorbing multiple co-existed metal ions (Cr(VI), Cd(II), Cu(II), Pb(II), Ni(II) and Zn(II)), phenolic recovery was first proved to be a new and sustainable strategy for modifying biosorbents from agricultural byproducts with zero waste.
In plants, hydroxycinnamic and hydroxybenzoic acids occur mainly as esters. This study aimed to determine the contribution of individual phenolic acid esterases in Lp. plantarum TMW1.460, which encodes for four esterases: TanA, Lp_0796, Est_1092 and a homolog of Lj0536 and Lj1228 that was termed HceP. To determine which of the phenolic acid esterases present in Lp plantarum TMW1.460 are responsible for esterase activity, mutants with deletions in lp_0796, est_1092, tanB, hceP, or hceP and est_1092 were constructed. The phenotype of wild type strain and mutants was determined with esters of hydroxycinnamic acids (chlorogenic acid and ethyl ferulate) and of hydroxybenzoic acids (methyl gallate, tannic acid and epigallocatechin-3-gallate). Lp. plantarum TMW1.460 hydrolysed chlorogenic acid, methyl ferulate and methyl gallate but not tannic acid or epigallocatechin gallate. The phenotype of mutant strains during growth in mMRS differed from the wild type as follows: Lp. plantarum TMW1.460ΔhceP did not hydrolyse esters of hydroxycinnamic acids; Lp. plantarum TMW1.460ΔtanB did not hydrolyse esters of hydroxybenzoic acids; disruption of est_1092 or Lp_0796 did not alter the phenotype. The phenotype of Lp. plantarum TMW1.460ΔΔhceP/est_1092 was identical to Lp. plantarum TMW1.460ΔhceP. The metabolism of phenolic acids during growth of the mutant strains in broccoli puree and wheat sourdough did not differ from metabolism of the wild type strain. In conclusion, esters of hydroxycinnamic and hydroxybenzoic acids each are hydrolysed by dedicated enzymes. The hydroxycinnamic acid esterase HceP is not expressed, or not active during growth of Lp. plantarum TMW1.460 in all food substrates.
There are numerous secondary plant metabolites found in the crop B. juncea, especially glucosinolates. Isothiocyanates, the by-products of glycosinolate breakdown, are beneficial to human health. A number of studies have also called attention to phenolic compounds and carotenoids, both well known for their anti-oxidant properties. A notable feature is that the profiles and concentrations of secondary plant metabolites vary greatly between varieties and that genetic factors are thought to be the most significant factors. In addition, environmental and agronomic factors have also been noted to change the concentrations of secondary plant metabolites. Secondary plant metabolites are primarily produced for defense purposes. Consequently, the intrinsic quality of Indian mustard, including color, aroma, taste, and medicinal properties, is profoundly influenced by its secondary metabolite profile. The health benefits of glycosinolates and the cancer prevention properties of their breakdown products make them of specific interest. Plant cells that have been injured undergo enzymatic decomposition of glucosinolate by endogenous enzymes such as myrosinase, which releases degradation products such as nitriles, epithionitriles, or isothiocyanates. The main phenolic compounds found in B. juncea are flavonoids and hydroxycinnamic acid derivatives. A diverse secondary metabolite pool is also essential for plant-environment interactions.
The objective was to study the phytochemical profile of yellow (Sinapis alba) and oriental mustard (Brassica juncea) flour and bran fractions. The HS-SPME-GC/MS technique was used to determine the volatile profile. Up to 53 volatiles, including isothiocyanates, alkanes, alcohols, ketones and esters were identified in the mustard powders. In addition, the free and bound bioactive fraction was studied and the determination was performed by UHPLC-MS/MS. A total of 26 compounds (phenolic acids, flavonoids and glucosinolates) were identified in the mustard samples. Sinapis alba, including the bran fraction, was richer in p-hydroxybenzoic, ferulic and p-coumaric acids compared to Brassica juncea. In addition, the volatile profile in yellow mustard seeds, as analysed by HS-SPME-GC/MS, has been described for the first time in this work. The study of the principal components showed that according to the bioactive compounds profile it is possible to differentiate between the two mustard species analysed. Moreover, the bran fraction, as a by-product of the seed processing, is a matrix rich in bioactive compounds and could be applied for the recovery of polyphenols for agro-industrial or pharmaceutical application.
Tyrosinase is a bifunctional polyphenol oxidase (PPO), catalyzing two oxidative reactions: monophenols to o-quinones (monophenolase activity) and o-diphenols to o-quinones (diphenolase activity). As tyrosinase is the rate-limiting enzyme for the melanogenesis process, it is an attractive target for melanogenesis inhibition. Aiming at skin whitening, anticancer, Parkinson’s disease (PD) treatment, antibacterial, fruit and vegetable preservation and other anti-pigmentation effect, medicinal chemists have exploited diverse tyrosinase inhibitors through various approaches. In addition to discovering inhibitors with novel scaffold, good activity and high safety, researchers also focused on developing strategies for synergistic effects of multiple inhibitors and simultaneously regulating multiple targets to treat cancer or neurodegenerative diseases. This review focused on multiple natural and synthetic tyrosinase inhibitors which could contribute to preventing fruit and vegetable browning, skin whitening, antibacterial, anticancer, Parkinson's Disease etc.
Chronic diseases including cardiovascular diseases, diabetes, cancers, neurodegenerative diseases and chronic respiratory diseases are the major causes of global deaths. Poor diet is the main risk factor that is linked to the occurrence of degenerative diseases. Owing to their potential effects in the prevention of chronic diseases, bioactive compounds have attracted great attention. The health beneficial effects of food bioactive compounds are attributed to their antioxidant, anti-inflammatory, antimicrobial, antiatherogenic, antithrombotic, cardioprotective and vasodilator properties, among others. In this chapter, the health promoting features of major bioactive compounds including polyphenols, carotenoids, vitamins, glucosinolates, triterpenes, phytosterols, alkaloids, capsaicinoids, polysaccharides, polyunsaturated fatty acids and bioactive peptides are discussed briefly.KeywordsPolyphenolsCarotenoidsVitaminsGlucosinolatesTriterpenesPhytosterolsAlkaloidsCapsaicinoidsPolysaccharidesPolyunsaturated fatty acidsBioactive peptides
In the present era, using natural antimicrobial agents has gained a wide recognition by consumers and the food industries alike, due to their safe nature as compared to the synthetic antibiotics that cause resistance in the microbes. These compounds have a potential to be used against broad range of microbes and food pathogens. There is a wide range of antimicrobials derived from plants, animals, and microbial sources as well as from the byproducts of food processing industry. The antimicrobial agents may be applied either directly in contact with the product or by indirect contact systems (as films, coatings, sachets and or encapsulated) of packaging. The mode of diffusion varies from one system to the other. Therefore, different packaging systems have different applications as per the requirement and or situation. The incorporation of antimicrobial agents in food packaging systems have been found to enhance the keeping quality in addition to the shelf-life extension of the food products. Despite the growing demand of the natural antimicrobials, there are certain limitations like objectionable flavors, authoritarian issues, undesirable interaction with the food components, and non-optimized standards associated with them. Hence, there are still many research gaps to be filled for commercializing or industrial applications of various types of antimicrobial agents. This article provides information about the antimicrobials from these sources along with their prospective applications in the food systems. Besides, a complete insight of their mode of application for the shelf-life enhancement in food products is also outlined.
Rapeseed meal is the dry residue of the rapeseed de-oiling process. It contains more phenolic compounds than any other oilseed meal. In analysis, rapeseed phenolic esters, mainly sinapine, are usually hydrolyzed to free phenolic acids, because sinapine is not available as a commercial standard. In this study, the efficiencies of different enzymes and enzyme preparations in hydrolyzing sinapine to sinapic acid were explored. The main phenolics in rapeseed meal were sinapine and sinapic acid. In rapeseed oil, the main phenolics were vinylsyringol, sinapine and sinapic acid. In hydrolyzing rapeseed meal, ferulic acid esterase and Ultraflo L were as effective in hydrolyzing sinapine as sodium hydroxide. Over 90% of sinapic acid derivatives were hydrolyzed to yield sinapic acid. Compared to base hydrolysis, enzyme treatment was not only as efficient but also less destructive to the liberated phenolics. Thus, enzymatic hydrolysis is a recommended procedure for optimal analysis of rapeseed phenolics. In rapeseed oils, hydrolysis was best applied in crude post-expelled rapeseed oils with high phenolic content.
Indian mustard [Brassica juncea (L.) Czern.] is a more productive oilseed than canola (B. napus L.) in hot regions of Russia, India, China, and Canada with somewhat unreliable rainfalls, whereas canola is the higher yielding species in more temperate, wetter regions. The specific agronomic features of the species, and their performance in various Australian regions are reviewed.
The discovery of the genes for low erucic acid oil production in the seeds of Indian mustard began the conversion of this ancient crop to a canola-type oilseed for dry areas. Initially, many accessions were field-tested at Wagga Wagga and Canberra, but 2 seed-borne diseases, leaf and stem blight and seed rot, were destructive. Accessions from South Asia were severely damaged by the blight caused by Pseudomonas syringae pv. maculicola Young, Dye & Wilkie 1978, whereas most of the cultivars from latitudes above 45°N were resistant. A phytotron procedure was developed for screening seedlings. The segregation pattern in F2 families from resistant × susceptible crosses suggested that reactions to a typical Pseudomonas isolate were controlled largely by co-dominant resistance (PsmR ) and susceptibility (PsmS ) alleles at one locus. F3 families with field resistance equal to the PsmR/PsmR parents were readily recovered, indicating that few or no modifying genes affected disease reactions. Resistant families selected from each of 6 crosses yielded 13.8% more seed (P < 0.001) than the corresponding segregating and susceptible families when these were tested at Canberra and Wagga Wagga. The disease became unimportant when most entries in field trials were resistant.
A seed-rotting disease caused by a yeast with distinctive ascospores closely resembling those of Nematospora sinecauda Holley, Allan-Wotjas & Phipps-Todd 1984 occurred in some imported and locally grown seed samples, but was eliminated by hot water treatment of seed prior to sowing and by control of the presumed insect vector, Nysius vinitor (Bergroth), during seed maturation in the field. No previous record of the occurrence of this disease in Australia was found in the literature by a plant pathologist.
The availability of breeding lines with low erucic acid seed oil, Pseudomonas resistance, and a predominance of propenyl glucosinolate in the meal permitted the development of a cold-pressed, edible oil industry by a family company (Yandilla Mustard Oil Enterprise) at Wallendbeen, NSW. The original oil has a mild nutty flavour, but now a larger proportion of the market requires a pungent, mustard-flavoured oil containing a trace of propenyl isothiocyanate, the hydrolytic product of the corresponding glucosinolate in the meal. The full-flavoured meal is sold for table mustard and pickle manufacture, as a stock feed ingredient containing approximately 30% protein and 18% oil, and for the distillation, by another small company at Cowra, NSW, of propenyl isothiocyanate, which is used as a flavouring and preservative in food, especially in Japan. This review describes the breeding of cultivars for cold-pressed oil production, as an off-shoot of the canola-grade B. juncea project.
Five successively improved, Pseudomonas-resistant cultivars were developed by crossing and pedigree selection for higher yield under a range of limiting conditions, and released for cold-pressed, low erucic acid oil production. The rate of yield increase in the cultivars released between 1989 and 2001 was 2.4% per annum as judged from small plot yields of all cultivars in each of 4 years at Wallendbeen. Flowering time adjustment provided a one-off improvement, but continued progress seems possible by field selection for traits such as increased resistance to the Sclerotinia and Alternaria pathogens, resistance to acid soils, waterlogging, frost at flowering, heat and drought during seed maturation, and increased efficiency of nutrient utilisation.
The nutraceutical properties of mustard oil, and the chemical differences among current B. juncea seed products, are described. Possible future developments are discussed.
Nine phenolic acids were identified and quantified by HPLC–MS in leaves and 10 in seeds of kale (black cabbage). The free, ester (methanol-soluble), glycoside and ester-bound (methanol-insoluble) phenolic acid contents of the leaves were 487, 532, 4989 and 6402 ng/g fresh weight, respectively. Ferulic and caffeic acids (total contents; 4269 and 4887 ng/g, respectively) were the most abundant. The seed contents of these fractions were 1993, 1477, 1231 and 4909 ng/g dry weight (DW), respectively, and sinapic acid was the most abundant (5037 ng/g DW). The fractions’ total phenolic contents, determined colorimetrically, were highly correlated with their DPPH scavenging capacity, and in antimicrobial activity assays, with nine test organisms representing a wide array of taxa, all of the fractions were effective against Staphylococcus aureus, Enterococcus faecalis, Bacillus subtilis and (most strongly) Moraxella catarrhalis. Antimicrobial and antioxidant activities of kale phenolics in free and conjugated forms are discussed.
Phenolic compounds are a large group of phytochemicals widespread in the plant kingdom. Depending on their structure they can be classified into simple phenols, phenolic acids, hydroxycinnamic acid derivatives and flavonoids. Phenolic compounds have received considerable attention for being potentially protective factors against cancer and heart diseases, in part because of their potent antioxidative properties and their ubiquity in a wide range of commonly consumed foods of plant origin. The Brassicaceae family includes a wide range of horticultural crops, some of them with economic significance and extensively used in the diet throughout the world. The phenolic composition of Brassica vegetables has been recently investigated and, nowadays, the profile of different Brassica species is well established. Here, we review the significance of phenolic compounds as a source of beneficial compounds for human health and the influence of environmental conditions and processing mechanisms on the phenolic composition of Brassica vegetables.
Brassicaceous plants are characterized by a pronounced metabolic flux toward sinapate, produced by the shikimate/phenylpropanoid pathway, which is converted into a broad spectrum of O-ester conjugates. The abundant sinapate esters in Brassica napus and Arabidopsis thaliana reflect a well-known metabolic network, including UDP-glucose:sinapate glucosyltransferase (SGT), sinapoylglucose:choline sinapoyltransferase (SCT), sinapoylglucose:L-malate sinapoyltransferase (SMT) and sinapoylcholine (sinapine) esterase (SCE). 1-O-Sinapoylglucose, produced by SGT during seed development, is converted to sinapine by SCT and hydrolyzed by SCE in germinating seeds. The released sinapate feeds via sinapoylglucose into the biosynthesis of sinapoylmalate in the seedlings catalyzed by SMT. Sinapoylmalate is involved in protecting the leaves against the deleterious effects of UV-B radiation. Sinapine might function as storage vehicle for ready supply of choline for phosphatidylcholine biosynthesis in young seedlings. The antinutritive character of sinapine and related sinapate esters hamper the use of the valuable seed protein of the oilseed crop B. napus for animal feed and human nutrition. Due to limited variation in seed sinapine content within the assortment of B. napus cultivars, low sinapine lines cannot be generated by conventional breeding giving rise to genetic engineering of sinapate ester metabolism as a promising means. In this article we review the progress made throughout the last decade in identification of genes involved in sinapate ester metabolism and characterization of the encoded enzymes. Based on gene structures and enzyme recruitment, evolution of sinapate ester metabolism is discussed. Strategies of targeted metabolic engineering, designed to generate low-sinapate ester lines of B. napus, are evaluated.
A high-performance liquid chromatographic (HPLC) method with diode array detection (DAD) was used to determine the total phenolics, including sinapic acid derivatives in canola. Ten Western Canadian canola seeds, six other commodity canola seeds, their corresponding press cakes and meals were analyzed. Seeds of European 00 rapeseed and Brassica Juncea (Indian mustard) were included for comparison. Phenolic compounds were separated using a gradient elution system of water-methanol-omicron-phosphoric acid solution with a flow rate of 0.8 ml/min. In addition to sinapine (SP) and sinapic acid (SA), sinapoyl glucose (SG) is reported in the methanolic extracts. The detection and quantification limits of these compounds were 0.20-0.40 and 0.50-0.80 mug/ml, respectively with recovery values over 98.0%. The content of total phenolics, SP, SA and SG in canola extracts ranged from 9.16 to 16.13, 6.39 to 12.28, 0.11 to 0.59 and 1.36 to 7.50 mg/g, respectively with significant differences among varieties.
The aim of the study was to evaluate the in vitro antibacterial effects of glucosinolate hydrolysis products (GHP) against plant pathogenic micro-organisms namely Agrobacterium tumefaciens, Erwinia chrysanthemi, Pseudomonas cichorii, Pseudomonas tomato, Xanthomonas campestris and Xanthomonas juglandis.
Using a disc diffusion assay, seven different doses of 10 GHP were tested against each bacteria. The results showed that the isothiocyanates were potent antibacterials, whilst the other GHP were much less efficient. Moreover, the antibacterial effects were dose-dependent, increasing with the dose applied; 2-phenylethylisothiocyanate and sulforaphane showed the strongest inhibitory effects. The overall results show a great potential for using the isothiocyanates as an alternative tool to control undesired bacterial growth in plants.
Glucosinolate hydrolysis products and more specifically the isothiocyanates: benzylisothiocyanate, 2-phenylethylisothiocyanate, the isothiocyanate Mix and sulforaphane, were effective phytochemicals against the in vitro growth of the phytopathogenic bacteria. The antibacterial activity exhibited by these phytochemicals reinforces their potential as alternatives to the traditional chemical control of phytopathogenic bacteria.
This current in vitro study is the first providing comparative data on GHP as potential control agents for plant pathogenic bacteria. However, more studies are needed to determine their possible allelopathic impacts e.g. inhibition of plant growth and negative effects on beneficial soil bacteria and fungi (mycorrhizae).
The bactericidal activity of allyl and methyl isothiocyanate (AITC and MITC) was tested with a rifampicin-resistant strain of Salmonella Montevideo and streptomycin-resistant strains of Escherichia coil O157:H7 and Listeria monocytogenes Scott A. Iceberg lettuce inoculated with high (10(7) to 10(8) CFU/g) and low (10(3) to 10(4) CFU/g) concentrations of bacterial pathogens was treated with AITC and MITC in sealed containers at 4 degrees C for 4 days. AITC showed stronger bactericidal activity than MITC against E. coli O157:H7 and Salmonella Montevideo, whereas MITC showed stronger activity against L. monocytogenes than E. coli O157:H7 and Salmonella Montevideo. Up to 8-log reduction occurred with E. coli O157:H7 and Salmonella Montevideo on lettuce following treatment with vapor generated from 400 microl of AITC for 2 and 4 days, respectively. AITC was used to treat tomatoes inoculated with Salmonella Montevideo on stem scars and skin and apples inoculated with E. coli O157:H7 on stem scars. The bactericidal effect of AITC varied with bacteria species and exposure time. Salmonella Montevideo inoculated on tomato skin was more sensitive to AITC than that on stem scars. Treatment with vapor generated from 500 microl of AITC caused an 8-log reduction in bacteria on tomato skin but only a 5-log reduction on tomato stem scars. The bactericidal activity of AITC was weaker for E. coli O157:H7 on apple stem scars; only a 3-log reduction in bacteria occurred when 600 microl of AITC was used.
Lactobacillus plantarum NC8 contains a pdcgene coding for p-coumaric acid decarboxylase activity (PDC). A food grade mutant, designated LPD1, in which the chromosomalpdc gene was replaced with the deleted pdc gene copy, was obtained by a two-step homologous recombination process using an unstable replicative vector. The LPD1 mutant
strain remained able to weakly metabolize p-coumaric and ferulic acids into vinyl derivatives or into substituted phenyl propionic acids. We have shown that L. plantarum has a second acid phenol decarboxylase enzyme, better induced with ferulic acid than withp-coumaric acid, which also displays inducible acid phenol reductase activity that is mostly active when glucose is added.
Those two enzymatic activities are in competition for p-coumaric and ferulic acid degradation, and the ratio of the corresponding derivatives depends on induction conditions. Moreover,
PDC appeared to decarboxylate ferulic acid in vitro with a specific activity of about 10 nmol · min−1 · mg−1 in the presence of ammonium sulfate. Finally, PDC activity was shown to confer a selective advantage on LPNC8 grown in acidic
media supplemented withp-coumaric acid, compared to the LPD1 mutant devoid of PDC activity.
To investigate the antimicrobial properties of phenolic compounds present in Finnish berries against probiotic bacteria and other intestinal bacteria, including pathogenic species.
Antimicrobial activity of pure phenolic compounds representing flavonoids and phenolic acids, and eight extracts from common Finnish berries, was measured against selected Gram-positive and Gram-negative bacterial species, including probiotic bacteria and the intestinal pathogen Salmonella. Antimicrobial activity was screened by an agar diffusion method and bacterial growth was measured in liquid culture as a more accurate assay. Myricetin inhibited the growth of all lactic acid bacteria derived from the human gastrointestinal tract flora but it did not affect the Salmonella strain. In general, berry extracts inhibited the growth of Gram-negative but not Gram-positive bacteria. These variations may reflect differences in cell surface structures between Gram-negative and Gram-positive bacteria. Cloudberry, raspberry and strawberry extracts were strong inhibitors of Salmonella. Sea buckthorn berry and blackcurrant showed the least activity against Gram-negative bacteria.
Different bacterial species exhibit different sensitivities towards phenolics.
These properties can be utilized in functional food development and in food preservative purposes.
The possible origin of beef contamination and genetic diversity of Escherichia coli populations in beef cattle, on carcasses and ground beef, was examined by using random amplification of polymorphic DNA (RAPD)
and PCR-restriction fragment length polymorphism (PCR-RFLP) analysis of the fliC gene. E. coli was recovered from the feces of 10 beef cattle during pasture grazing and feedlot finishing and from hides, carcasses, and
ground beef after slaughter. The 1,403 E. coli isolates (855 fecal, 320 hide, 153 carcass, and 75 ground beef) were grouped into 121 genetic subtypes by using the RAPD
method. Some of the genetic subtypes in cattle feces were also recovered from hides, prechilled carcasses, chilled carcasses,
and ground beef. E. coli genetic subtypes were shared among cattle at all sample times, but a number of transient types were unique to individual
animals. The genetic diversity of the E. coli population changed over time within individual animals grazing on pasture and in the feedlot. Isolates from one animal (59
fecal, 30 hide, 19 carcass, and 12 ground beef) were characterized by the PCR-RFLP analysis of the fliC gene and were grouped into eight genotypes. There was good agreement between the results obtained with the RAPD and PCR-RFLP
techniques. In conclusion, the E. coli contaminating meat can originate from cattle feces, and the E. coli population in beef cattle was highly diverse. Also, genetic subtypes can be shared among animals or can be unique to an animal,
and they are constantly changing.
Total contents of aromatic choline esters and sinapine have been investigated in seeds of cruciferous species belonging to Arabis, Brassica, Cakile, Diplotaxs, Eruca, Hesperis, Matthiola, Raphanobrassica, Raphanus and Sïnapis. Choline esters such as sinapine, isoferuloylcholine, feruloylcholine, hesperaline and 4-hydroxybenzoylcholine, have been found in many of the plants under study. Qualitative and quantitative distribution patterns of these compounds are genus-characteristic. This suggests them to be a useful tool in the chemotaxonomy of Crucifereae. In spite of their genus-specific distribution pattern, the capacity of plants to accumulate and store phenolic choline esters in seeds is highly variable within the genus Brassica. Besides a genetic control, the aromatic choline esters content is also influenced by environmental conditions. Brassica species with high and low chromosome numbers were compared according to their qualitative and quantitative aromatic choline ester content. Genomic divergence or affinity among the species under study are discussed.
Effect of hydrocinnamic acids on the growth of lactic bacteria. Hydroxycinnamic acids, their quinic esters and quinic acid are present in apple juice and cider. Effects of each of these compounds and of two mixtures on the growth of one strain of two lactic acid bacteria species were studied by a four level factorial design. Each design involved three factors. Thus sixteen designs were required to achieve the work described in the present paper. The compounds were the following hydroxycinnamic acids: Ferulic acid, p-Coumaric acid, Caffeic acids, p-Coumaroyl quinic acid, 5'-Caffeoyl quinic acid and the non-phenolic acid: Quinic acid. The two mixtures on an equimolecular basis were: p-Coumaric acid/Quinic acid and Caffeic acid/Quinic acid. The lactic bacteria species were: Oenococcus oeni and Lactobacillus plantarum. The factors involved were: pH, tested compound concentration and pitching rate. Two growth parameters were examined: apparent growth rate and biomass production. Results showed that esters and Quinic acid were not active and that bacterial growth was only affected by hydroxycinnamic acid concentrations. A decreasing inhibitory effect was shown from Ferulic acid to p-Coumaric acid and Caffeic acid. The two strains behaved differently: both apparent growth rate and biomass production decreased for Oenococcus oeni while only the apparent growth rate was affected for Lactobacillus plantarum.
AUTEUR(S)
A.G. SALIH, J.-M. LE QUÉRÉ, J.-F. DRILLEAU
Reçu le 10 septembre 1999. Accepté le 17 juillet 2000.
MOTS-CLÉS
composé phénolique, bactérie lactique, croissance bactérienne, pH, cidre.
KEYWORDS
lactic acid bacteria, bacterial growth, phenolic compounds, pH, cider.
LANGUE DE L'ARTICLE
Français
Antioxidative and bactericidal properties were investigated in isolated and fractionated phenolic compounds of rapeseeds. Among the investigated groups of compounds (phenolic acids, sinapine and the products of its hydrolysis) phenolic acids, and especially sinapic acid, were found to be the most active. Due to valuable properties of these compounds they can be considered to be applied for food and fodder preserving.
Antioxidative und antibakterielle Eigenschaften der Rapsphenolverbindungen
Antioxidative und antibakterielle Eigenschaften wurden in isolierten und fraktionierten Rapsphenolverbindungen untersucht. Unter den untersuchten Phenolverbindungen (Phenolsäuren, Sinapin und Produkte ihrer Hydrolyse) zeichneten sich Phenolsäuren sowie substantielle Ableitungen der Sinapinsäure durch die höchste Aktivität aus. Diese wertvollen Eigenschaften könnten bei der Haltbarmachung von Lebens- und Futtermitteln genutzt werden.
A methanol extract from yellow mustard seeds had antibacterial activity against Escherichia coli, Salmonella enteritidis, and Staphylococcus aureus. Two compounds with such activity were isolated from the extract. By instrumental analysis, the compounds were identified as 4-hydroxy-3-nitrophenylacetic and sinapic acids. Examination of the structure-activity relationship showed that the hydroxyl and nitro groups of the first compound were involved in the activity against all three species. The two methoxyl groups and the hydroxyl group in sinapic acid were effective against E. coli and all of the substituents of the benzene ring were effective against S. enteritidis. The presence of the propenoic group of the second compound was effective against S. aureus.
Hydroxycinnamic acid conjugates (HCAcs) and dihydrohydroxycinamic acid conjugates (DHCAcs) were identified and quantified in potato tuber extracts by UHPLC–DAD–ESI-MSn. The HCAcs and DHCAcs identification took place by screening for product ions and neutral losses in combination with UV spectra. Thirty-nine HCAcs/DHCAcs were detected, including 17 previously reported in potato. HCAs were found unconjugated, linked to hydroxyl-containing compounds including hexose, quinic acid and malic acid, to amino-containing compounds, such as putrescine and octopamine, and to unknown compounds. DHCAs were present linked to spermine, spermidine and to still unidentified compounds. Chlorogenic acid was the most abundant compound (25.43 ± 0.49 mg/g DW) followed by cryptochlorogenic acid (7.31 ± 0.38 mg/g DW), a non-hydrolyzable sinapic acid conjugate (2.80 ± 0.06 mg/g DW) and neochlorogenic acid (2.41 ± 0.10 mg/g DW), in total accounting for 83% (w/w) of the total concentration of HCAs/DHCAs-containing compounds. Quantifications of HCAs released after alkaline hydrolysis matched well with the quantification of the unhydrolyzed molecules. The UHPLC–DAD–ESI-MSn method showed a larger diversity of HCAcs and DHCAcs in potato than described before.
Phenolic acids account for almost one third of the dietary phenols and are associated with organoleptic, nutritional and antioxidant properties of foods. This study was undertaken to assess the ability of Lactobacillus plantarum CECT 748T to metabolize 19 food phenolic acids. Among the hydroxycinnamic acids studied, only p-coumaric, caffeic, ferulic and m-coumaric acids were metabolized by L. plantarum. Cultures of L. plantarum produced ethyl and vinyl derivatives from p-coumaric and caffeic acids, 4-vinyl guaiacol from ferulic acid, and 3-(3-hydroxyphenyl) propionic acid from m-coumaric acid. Among the hydroxybenzoic acids analysed, gallic acid and protocatechuic acid were decarboxylated to pyrogallol and catechol, respectively. Inducible enzymes seem to be involved, at least in m-coumaric and ferulic acid metabolism, since cell-free extracts from cultures grown in the absence of these phenolic acids were unable to metabolize them. Further work is needed for the identification of the enzymes involved, since the knowledge of the metabolism of phenolic compounds is an important issue for the food industry.
Amongst oilseeds, rapeseed and mustard are rich sources of phenolic compounds, which also prominent in the by-products of their respective oil processing or in commercial rapeseed and mustard press cakes. These cakes are rich sources of sinapic acid derivatives, which could be extracted as free sinapic acid or sinapine, the choline ester of sinapic acid. Sinapic acid is a widely investigated antioxidative compound. However, the main compound in the press cakes is present as sinapine. Investigations on the free-radical-scavenging activity of sinapic acid and sinapine indicate that sinapine had a significant but lower activity as compared to sinapic acid. Apart from this, sinapic acid, sinapine and different tocopherols were compared as antioxidants for inhibition of the formation of lipid oxidation products in purified rapeseed oils. The oxidation at 40 °C was monitored by the formation of hydroperoxides and propanal. The experiments indicate that in contrast to tocopherol mixtures addition of sinapic acid causes increasing inhibition of hydroperoxide formation when enhancing the concentration from 50 to 500 μmol/kg oil. Sinapine was not able to inhibit the formation of hydroperoxides, compared to sinapic acid. This indicates that sinapic acid-rich extracts, as compared to sinapine-rich fractions, could better inhibit the lipid oxidation in bulk lipid systems.
The effects of hop extract and ethanol on growth, high pressure inactivation, and survival of Lactobacillus plantarum were determined in model beer. Corresponding to the beer spoiling ability of this strain, levels of hops and ethanol typical for beer did not inhibit growth. Pressure death time curves determined at 300 MPa were described by an empirical model taking into account the sigmoid shape of survivor curves, sublethal injury, and the presence of baroresistant cells. Ethanol (5 and 10%) enhanced pressure effects on L. plantarum whereas hop extract (50 and 100 ppm) was less effective. In contrast, hop extracts killed pressurized cells during subsequent storage in beer but ethanol did not.
Four conjugates of gentiobiose were isolated, from fresh, raw broccoli florets, using mild extraction conditions and preparative HPLC. From spectroscopic evidence the structures were characterized as two novel conjugates of gentiobiose: 1,2′-disinapoyl-2-feruloygentiobiose and 1-sinapoyl-2-feruloylgentiobiose and, two compounds previously reported to be present in the fruits of Boreave orientalis, a member of the Cruciferae, 1,2,2′-trisinapovigentiobiose and 1,2-disinapoylgentiobiose. © 1997 Elsevier Science Ltd. All rights reserved
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.
Seven flavonol glycosides were isolated from a leaf extract of cabbage and characterized by chemical and spectroscopic methods including 1H and 13C NMR and negative ion FAB-MS. Five compounds were new natural products or were fully characterized for the first time. They are derivatives of kaempferol-3-O-β-d-sophoroside-7-O-β-d-glucoside acylated at C-2‴ with either caffeic acid, p-coumaric acid or ferulic acid, and of quercetin-3-O-β-d-sophoroside-7-O-β-d-glucoside acylated with either caffeic acid or ferulic acid. Kaempferol-3-O-β-d-sophoroside-7-O-β-d-glucoside and kaempferol-3-O-β-d-(2-sinapoylsophoroside)-7-O-β-d-glucoside were found for the first time in cabbage, but they have previously been found in other Brassica species.
The utilization of rapeseed/canola as a source of food-grade proteins is still limited due the presence of glucosinolates, phytates, hulls and phenolics. Phenolic acids and condensed tannins are the predominant phenolic compounds found in rapeseed. The content of phenolic compounds in rapeseed/canola products is much higher than that found in corresponding products from other oleaginous seeds. Phenolics such as free phenolic acids, sinapines and condensed tannins may contribute to the bitter taste and astringency of rapeseed products. In addition, both phenolic acids and condensed tannins may form complexes with proteins, thus lowering the nutritional value of rapeseed products. The specific mode of interaction of rapeseed phenolics with proteins is still not well understood. Therefore, a better knowledge of factors which influence the interactions between phenolics and proteins would be beneficial in developing more efficient technologies for production of phenolic-free rapeseed protein isolates.
An UHPLC-PDA-ESI/HRMS/MS(n) profiling method was used for a comprehensive study of the phenolic components of red mustard greens ( Brassica juncea Coss variety) and identified 67 anthocyanins, 102 flavonol glycosides, and 40 hydroxycinnamic acid derivatives. The glycosylation patterns of the flavonoids were assigned on the basis of direct comparison of the parent flavonoid glycosides with reference compounds. The putative identifications were obtained from tandem mass data analysis and confirmed by the retention time, elution order, and UV-vis and high-resolution mass spectra. Further identifications were made by comparing the UHPLC-PDA-ESI/HRMS/MS(n) data with those of reference compounds in the polyphenol database and in the literature. Twenty-seven acylated cyanidin 3-sophoroside-5-diglucosides, 24 acylated cyanidin 3-sophoroside-5-glucosides, 3 acylated cyanidin triglucoside-5-glucosides, 37 flavonol glycosides, and 10 hydroxycinnamic acid derivatives were detected for the first time in brassica vegetables. At least 50 of them are reported for the first time in any plant materials.
To determine structure-function relationships of antibacterial phenolic acids and their metabolites produced by lactic acid bacteria (LAB).
Minimum inhibitory concentrations (MICs) of 6 hydroxybenzoic and 6 hydroxycinnamic acids were determined with Lactobacillus plantarum, Lactobacillus hammesii, Escherichia coli and Bacillus subtilis as indicator strains. The antibacterial activity of phenolic acids increased at lower pH. A decreasing number of hydroxyl groups enhanced the activity of hydroxybenzoic acids, but had minor effects on hydroxycinnamic acids. Substitution of hydroxyl groups with methoxy groups increased the activity of hydroxybenzoic, but not of hydroxycinnamic, acid. Metabolism of chlorogenic, caffeic, p-coumaric, ferulic, protocatechuic or p-hydroxybenzoic acids by L. plantarum, L. hammesii, Lactobacillus fermentum and Lactobacillus reuteri was analysed by LC-DAD-MS. Furthermore, MICs of substrates and metabolites were compared. Decarboxylated and/or reduced metabolites of phenolic acids had a lower activity than the substrates. Strain-specific metabolism of phenolic acids generally corresponded to resistance.
The influence of lipophilicity on the antibacterial activity of hydroxybenzoic acids is stronger than that of hydroxycinnamic acids. Metabolism of phenolic acids by LAB detoxifies phenolic acids.
Results allow the targeted selection of plant extracts for food preservation, and selection of starter cultures for fermented products.
In this review, antimicrobials from a range of plant, animal, and microbial sources are reviewed along with their potential applications in food systems. Chemical and biochemical antimicrobial compounds derived from these natural sources and their activity against a range of pathogenic and spoilage microorganisms pertinent to food, together with their effects on food organoleptic properties, are outlined. Factors influencing the antimicrobial activity of such agents are discussed including extraction methods, molecular weight, and agent origin. These issues are considered in conjunction with the latest developments in the quantification of the minimum inhibitory (and noninhibitory) concentration of antimicrobials and/or their components. Natural antimicrobials can be used alone or in combination with other novel preservation technologies to facilitate the replacement of traditional approaches. Research priorities and future trends focusing on the impact of product formulation, intrinsic product parameters, and extrinsic storage parameters on the design of efficient food preservation systems are also presented.
Kale is a leafy green vegetable belonging to the Brassicaceae family, a group of vegetables including cabbage, broccoli, cauliflower, and Brussels sprouts, with a high content of health-promoting phytochemicals. The flavonoids and hydroxycinammic acids of curly kale ( Brassica oleracea L. ssp. oleracea convar. acephala (DC.) Alef. var. sabellica L.), a variety of kale, were characterized and identified primarily through HPLC-DAD-ESI-MS(n) analysis. Thirty-two phenolic compounds including glycosides of quercetin and kaempferol and derivatives of p-coumaric, ferulic, sinapic, and caffeic acid were tentatively identified, providing a more complete identification of phenolic compounds in curly kale than previously reported. Moreover, three hydroxycinnamic acids and one flavonoid with an unusual high grade of glycosylation, quercetin-3-disinapoyl-triglucoside-7-diglucoside, have been tentatively identified for the first time. The influence of different extraction conditions (extraction method, solvent type, solvent/solid ratio, and duration of extraction) was investigated. The total flavonol and hydroxycinnamic acid contents in curly kale determined as rutin equivalents (RE) were 646 and 204 mg of RE/100 g of fresh weight (fw), respectively. The contents of individual flavonoids ranged from 2 to 159 mg of RE/100 g of fw, with main compounds kaempferol-3-sinapoyl-diglucoside-7-diglucoside (18.7%) and quercetin-3-sinapoyl-diglucoside-7-diglucoside (16.5%). After acidic hydrolysis, two flavonol aglycones were identified in curly kale, quercetin and kaempferol, with total contents of 44 and 58 mg/100 g of fw, respectively.
This study shows that the growth of Oenococcus oeni CECT 4100 in a synthetic medium is affected by phenolic compounds in different ways, depending on their type and concentration. Generally they have no effects at low concentrations, but hydroxycinnamic acids are inhibitory at high concentrations. Malolactic fermentation was stimulated in the presence of catechin and quercetin, but increasingly delayed with increasing amounts of p-coumaric acid. Gallic acid appeared to delay or inhibit the formation of acetic acid from citric acid. This could lead to a better control of malolactic fermentation and suppress the increase in volatile acidity, which is undesirable in the wine-making process.
A high-performance liquid chromatographic (HPLC) method with diode-array detection (DAD) was used to identify and quantify free and total phenolic acids (m-hydroxybenzoic acid, p-hydroxybenzoic acid, protocatechuic acid, gallic acid, vanillic acid, syringic acid, o-coumaric acid, m-coumaric acid, p-coumaric acid, caffeic acid, ferulic acid, sinapic acid, chlorogenic acid, and ellagic acid) in plant foods. Free phenolic acids were extracted with a mixture of methanol and 10% acetic acid. Bound phenolic acids were liberated using first alkaline and then acid hydrolysis followed by extraction with diethyl ether/ethyl acetate (1:1). All fractions were quantified separately by HPLC. After HPLC quantification, results of alkali and acid hydrolysates were calculated to represent total phenolic acids. Ellagic acid was quantified separately after long (20 h) acid hydrolysis. The methods developed were effective for the determination of phenolic acids in plant foods. DAD response was linear for all phenolic acids within the ranges evaluated, with correlation coefficients exceeding 0.999. Coefficients of variation for 4-8 sample replicates were consistently below 10%. Recovery tests of phenolic acids were performed for every hydrolysis condition using several samples. Recoveries were generally good (mean >90%) with the exceptions of gallic acid and, in some cases, caffeic acid samples.
Aims: To determine the effect of several wine-associated, phenolic acids on the growth and viability of strains of Oenococcus oeni and Lactobacillus hilgardii.
Methods and Results: Growth was monitored in ethanol-containing medium supplemented with varying concentrations of hydroxybenzoic acids (p-hydroxybenzoic, protocatechuic, gallic, vanillic and syringic acids) and hydroxycinnamic acids (p-coumaric, caffeic and ferulic acids). Progressive inactivation was monitored in ethanol-containing phosphate buffer supplemented in a similar manner to the growth experiments. Hydroxycinnamic acids proved to be more inhibitory to the growth of O. oeni than hydroxybenzoic acids. On the other hand, some acids showed a beneficial effect on growth of Lact. hilgardii. p-Coumaric acid showed the strongest inhibitory effect on growth and survival of both bacteria.
Conclusions: Most phenolic acids had a negative effect on growth of O. oeni, for Lact. hilgardii this effect was only noted for p-coumaric acid. Generally, O. oeni was more sensitive to phenolic acid inactivation than Lact. hilgardii.
Significance and Impact of the Study: Eight wine-derived, phenolic acids were compared for their effects on wine lactic acid bacteria. Results indicate that phenolic acids have the capacity to influence growth and survival parameters. The differences found between phenolic compounds could be related to their different chemical structures.
Flavonoid differences between near-isogenic lines of yellow- and brown-seeded Brassica carinata were used to identify a genetic block in seed coat and seedling leaf pigment biosynthesis. Seed coat pigment in the brown-seeded line consisted of proanthocyanidins (condensed tannins), while anthocyanin was absent. Dihydroquercetin, dihydrokaempferol, quercetin and kaempferol accumulated only in the mature seed coat of the yellow-seeded line, indicating dihydroflavonol reductase (DFR) as an element of genetic control in pigment biosynthesis. DFR transcripts from the developing seed coat in the yellow-seeded line were absent or less abundant at 5-30 days after pollination compared to transcript levels in the brown-seeded line. Seedling leaves of the yellow-seeded line exhibited reduced expression of DFR and contained less anthocyanin compared to the respective tissues from plants of the brown-seeded line when grown at 25/20 degrees C (day/night). Cooler (18/15 degrees C) growing temperatures affected seedling leaf pigmentation, mature seed coat colouration and DFR expression in the yellow-seeded line. Comparable brown-seeded line tissues were unaffected by these temperature changes. These results are suggestive of a temperature-sensitive regulator of DFR in the yellow-seeded line of Brassica carinata which ultimately affects the formation of pigments in the seedling leaves and in the mature seed coats.
Glycosylated kaempferol derivatives from the external leaves of tronchuda cabbage (Brassica oleracea L. var. costata DC) characterized by reversed-phase HPLC-DAD-MS/MS-ESI were kaempferol 3-O-sophorotrioside-7-O-glucoside, kaempferol 3-O- (methoxycaffeoyl/caffeoyl)sophoroside-7-O-glucoside, kaempferol 3-O-sophoroside-7-O-glucoside, kaempferol 3-O-sophorotrioside-7-O-sophoroside, kaempferol 3-O-sophoroside-7-O-sophoroside, kaempferol 3-O-tetraglucoside-7-O-sophoroside, kaempferol 3-O-(sinapoyl/caffeoyl)sophoroside-7-O-glucoside, kaempferol 3-O-(feruloyl/caffeoyl)sophoroside-7-O-glucoside, kaempferol 3-O-sophorotrioside, kaempferol 3-O-(sinapoyl)sophoroside, kaempferol 3-O-(feruloyl)sophorotrioside, kaempferol 3-O-(feruloyl)sophoroside, kaempferol 3-O-sophoroside, and kaempferol 3-O-glucoside. These acylated derivatives are reported for the first time in nature, with the exception of kaempferol 3-O-(sinapoyl)sophoroside. Quantification of the identified compounds was achieved by HPLC-DAD and carried out in samples cultivated under conventional or organic practices and collected at different times. In general, samples from organic production exhibited higher total phenolics content than those from conventional practices collected in the same period.
Members of the Brassicaceae accumulate complex patterns of sinapate esters, as shown in this communication with seeds of oilseed rape (Brassica napus). Fifteen seed constituents were isolated and identified by a combination of high-field NMR spectroscopy and high resolution electrospray ionisation mass spectrometry. These include glucose, gentiobiose and kaempferol glycoside esters as well as sinapine (sinapoylcholine), sinapoylmalate and an unusual cyclic spermidine amide. One of the glucose esters (1,6-di-O-sinapoylglucose), two gentiobiose esters (1-O-caffeoylgentiobiose and 1,2,6'-tri-O-sinapoylgentiobiose) and two kaempferol conjugates [4'-(6-O-sinapoylglucoside)-3,7-di-O-glucoside and 3-O-sophoroside-7-O-(2-O-sinapoylglucoside)] seem to be new plant products. Serine carboxypeptidase-like (SCPL) acyltransferases catalyze the formation of sinapine and sinapoylmalate accepting 1-O-beta-acetal esters (1-O-beta-glucose esters) as acyl donors. To address the question whether the formation of other components of the complex pattern of the sinapate esters in B. napus seeds is catalyzed via 1-O-sinapoyl-beta-glucose, we performed a seed-specific dsRNAi-based suppression of the sinapate glucosyltransferase gene (BnSGT1) expression. In seeds of BnSGT1-suppressing plants the amount of sinapoylglucose decreased below the HPLC detection limit resulting in turn in the disappearance or marked decrease of all the other sinapate esters, indicating that formation of the complex pattern of these esters in B. napus seeds is dependent on sinapoylglucose. This gives rise to the assumption that enzymes of an SCPL acyltransferase family catalyze the appropriate transfer reactions to synthesize the accumulating esters.
Twenty-eight polyphenols (11 flavonoid derivatives and 17 hydroxycinnamic acid derivatives) were detected in different cultivars of the Chinese cabbage pak choi ( Brassica campestris L. ssp. chinensis var. communis) by HPLC-DAD-ESI-MS(n). Kaempferol was found to be the major flavonoid in pak choi, glycosylated and acylated with different compounds. Smaller amounts of isorhamnetin were also detected. A structural determination was carried out by (1)H and (13)C NMR spectroscopy for the main compound, kaempferol-3-O-hydroxyferuloylsophoroside-7-O-glucoside, for the first time. Hydroxycinnamic acid derivatives were identified as different esters of quinic acid, glycosides, and malic acid. The latter ones are described for the first time in cabbages. The content of polyphenols was determined in 11 cultivars of pak choi, with higher concentrations present in the leaf blade than in the leaf stem. Hydroxycinnamic acid esters, particularly malic acid derivatives, are present in both the leaf blade and leaf stem, whereas flavonoid levels were determined only in the leaf blade.
The aim of this work was to investigate the effect of wine phenolic aldehydes, flavonoids and tannins on growth and viability of strains of Oenococcus oeni and Lactobacillus hilgardii. Cultures were grown in ethanol-containing MRS/TJ medium supplemented with different concentrations of phenolic aldehydes or flavonoids and monitored spectrophotometrically. The effect of tannins was evaluated by monitoring the progressive inactivation of cells in ethanol-containing phosphate buffer supplemented with grape seed extracts with different molecular weight tannins. Of the phenolic aldehydes tested, sinapaldehyde, coniferaldehyde, p-hydroxybenzaldehyde, 3,4-dihydroxybenzaldehyde and 3,4,5-trihydroxybenzaldehyde significantly inhibited the growth of O. oeni VF, while vanillin and syringaldehyde had no effect at the concentrations tested. Lact. hilgardii 5 was only inhibited by sinapaldehyde and coniferaldehyde. Among the flavonoids, quercetin and kaempferol exerted an inhibitory effect especially on O. oeni VF. Myricetin and the flavan-3-ols studied (catechin and epicatechin) did not affect considerably the growth of both strains. Condensed tannins (particularly tetramers and pentamers) were found to strongly affect cell viability, especially in the case of O. oeni VF. In general, this strain was found to be more sensitive than Lact. hilgardii 5 to the phenolic compounds studied. This work contributes to the knowledge of the effect of different phenolic compounds on the activity of wine lactic acid bacteria, which, especially in the case of aldehydes and of different molecular weight fractions of tannins, is very scarce.
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