Phenolic compounds in peanut seeds: Enhanced elicitation by chitosan and effects on growth and aflatoxin B1 production by Aspergillus flavus

Effects of chitosan and Aspergillus flavus to enhance elicitation of phenolic compounds in viable peanut seeds were conducted at two water activity levels. In vitro effects of phenolic acids on A. flavus growth and aflatoxin B₁ production were also studied. Chitosan enhanced elicitation of free phenolic compounds (FPC) at Aw .85 and .95 levels. A. flavus initially decreased and subsequently increased FPC content, but bound phenolic compounds (BPC) decreased during incubation. Chitosan + A. flavus treatment caused an increase in FPC reaching a plateau between 24–48 h at Aw .85 while BPC levels increased over the same period at both Aw levels. Major free and bound phenolic acids detected were p‐coumaric, ferulic and an unknown phenolic acid eluting at a retention time of 22 min. Generally, chitosan significantly enhanced elicitation of free ferulic and p‐coumaric acids and bound p‐coumaric acid at Aw .95. Free unknown phenolic and bound ferulic acids at Aw .85 were enhanced by chitosan. A. flavus caused significant induction of bound p‐coumaric and ferulic acids and free unknown phenol at Aw .85. Chitosan + A. flavus enhanced free p‐coumaric (3 h) and unknown phenolic acids and bound p‐coumaric acid at Aw .95 while bound ferulic acid was enhanced at Aw .85. Chitosan limited A. flavus growth and subsequent aflatoxin production by inducing susceptible tissues to produce more preformed phenolic compounds.

Analysis of liquid cultures of A. flavus revealed that p‐coumaric, ferulic, and vanillic acids and a mixture of these phenolic acids slightly inhibited mycelial growth. Production of aflatoxin B₁ by A. flavus was completely inhibited at 1 mM and 10 mM concentrations of the phenolic acids and their mixture on four days of incubation. Mode of action of phenolic acids is likely on the secondary pathway for aflatoxin B₁ production and not on the primary metabolism for fungal growth.     

Composition and Nutrient Value Proposition of Brewers Spent Grain

Brewer's spent grain (BSG), a major brewing industry byproduct, is generated in large quantities annually. This review summarizes research into the composition and preservation of BSG, different extraction techniques for BSG proteins and phenolic acids, and the bioactivities of these phenolic components. Moreover, this article also highlights BSG integration into foodstuff for human consumption and animal feed supplements. BSG is considered a rich source of fiber, protein, and phenolic compounds. The phenolic acids present in BSG are hydroxycinnamic acids (ferulic, p‐coumaric, and caffeic acids), which have many biofunctions, such as antioxidant, anticarcinogenic, antiatherogenic, and antiinflammatory activities. Previously, attempts have been made to integrate BSG into human food, such as ready‐to‐eat snacks, cookies and bread, to increase fiber and protein contents. The addition of BSG to animal feed leads to increased milk yields, higher fat contents in milk, and is a good source of essential amino acids. Therefore, many studies have concluded that integrating the biofunctional compounds in BSG into human food and animal feed has various health benefits.     

Release of phenolic acids from defatted rice bran by subcritical water treatment

BACKGROUND: Oil production from rice bran, an undervalued by‐product of rice milling, produces defatted rice bran (DRB) as a waste material. Although it is considered a less valuable product, DRB still contains useful substances such as phenolic compounds with antioxidant, UV‐B‐protecting and anti‐tumour activities. In this study the phenolic acids in DRB were extracted with subcritical water at temperatures of 125, 150, 175 and 200 °C. RESULTS: Analysis of total phenolics using Folin–Ciocalteu reagent showed about 2–20 g gallic acid equivalent kg^?1 bran in the extracts. High‐performance liquid chromatography analysis showed low contents of phenolic acids (about 0.4–2 g kg^?1 bran). Ferulic, p‐coumaric, gallic and caffeic acids were the major phenolic acids identified in the extracts. Thermal analysis of the phenolic acids was also done. The thermogravimetric curves showed that p‐coumaric, caffeic and ferulic acids started to decompose at about 170 °C, while gallic acid did not start to decompose until about 200 °C. CONCLUSION: Subcritical water can be used to hydrolyse rice bran and release phenolic compounds, but the high temperatures used in the extraction can also cause the decomposition of phenolic acids. Copyright © 2010 Society of Chemical Industry     

果蔬酚酸生物合成及代谢调控研究进展

酚酸类物质是高等植物体内广泛分布的一类重要的次生代谢产物,具有抗氧化、抗炎、抗癌、抑菌、提高 免疫力等多种生物活性。近年来,大量的研究表明酚酸与植物生长发育及抗逆性、食品质量和人体健康密切相关, 有关植物酚酸的分离鉴定及生物合成途径已有广泛研究。本文综述了果蔬中酚酸的生物合成途径和酚酸与果蔬抗逆 性及品质间的关系,并对代谢组学在评价酚酸类物质分布规律中的应用进行了阐述,以期为酚酸类物质在果蔬中的 开发利用提供有益参考。     

Anthocyanins from Eugenia myrtifolia Sims

Eugenia myrtifolia Sims fruits have been characterized for their anthocyanin content and quality. Following the common procedures and validated methods for separation, identification and quantification of anthocyanins, we found the presence of malvidin 3,5-O-diglucoside as a unique anthocyanin (32,59 mg/100 g fresh weight of the fruit). An in vitro shoot culture of E. myrtifolia was established in order to explore the possibility to produce pigments in vitro. The presence of the only malvidin 3,5-O-diglucoside could be a useful feature in order to manipulate biotechnologically the anthocyanin biosynthetic pathway in the in vitro material (callus and suspension cultures).Industrial relevanceThe research interest on the phenolic composition of non-traditional food plants is a leading trend in the looking for biofunctional compounds to be included in “designer foods”.Eugenia myrtifolia, a Myrtaceae species from the South hemisphere, produces red edible fruits, that have been characterized for their anthocyanin composition, revealing the presence of the only malvidin 3,5-O-diglucoside, at relatively low amounts. Since attempts for in vitro callus production and for anthocyanin induction from the callus of E. myrtifolia have been carried out, the presence of the specific anthocyanin compound could be a useful feature in order to manipulate biotechnologically the anthocyanin biosynthetic pathway in the in vitro material, pushing the biosynthetic pathway towards the unique final product. Since malvidin is a final product (methoxylated anthocyanin) of the anthocyanin pathway, this in vitro system could help to study the regulation of the pathway, altering the genetic (regulator genes) or physiological control of the pathway. This could allow to obtain better product yields even in another in vitro systems, possibly overcoming the key bottleneck of the secondary metabolite production by plant cell and tissue cultures.     

Phenolic compounds in peanut seeds: Enhanced elicitation by chitosan and effects on growth and aflatoxin b1 production by aspergillus flavus

Effects of chitosan and Aspergillus flavus to enhance elicitation of phenolic compounds in viable peanut seeds were conducted at two water activity levels. In vitro effects of phenolic acids on A. flavus growth and aflatoxin B₁ production were also studied. Chitosan enhanced elicitation of free phenolic compounds (FPC) at Aw .85 and .95 levels. A. flavus treatment initially decreased and subsequently increased FPC content, but bound phenolic compounds (BPC) decreased during incubation. Chitosan + A. flavus treatments caused an increase in FPC that reached a plateau between 24–48 h at Aw .85 while BPC levels increased over the same time period at both Aw levels. The major free and bound phenolic acids detected were p‐coumaric and ferulic acids and an unknown phenol that eluted at a retention time of 22 min. Generally, chitosan treatment significantly enhanced elicitation of free ferulic and p‐coumaric acids and bound p‐coumaric acid at Aw .95. Free unknown phenolic and bound ferulic acids at Aw .85 were enhanced by chitosan. A. flavus treatment caused significant induction of bound p‐coumaric and ferulic acids and free unknown phenol at Aw .85. Chitosan + A. flavus treatment measure to reduce or eliminate pre‐harvest contamination by A. flavus and aflatoxins contributes to sustainable agriculture, especially to developing countries.

The enhanced elicitation of preformed phenolic compounds by chitosan may provide seed tissues an additive or synergistic effect in controlling aflatoxin‐producing fungi and preventing aflatoxin contamination. Further, such investigation will help elucidate the biochemical basis of elicitor‐host interaction that contribute to defensive responses of host tissues. Identification of biochemical factors in induced resistance involves a refinement in the separation and identification of induced phenolic compounds. Methodologies such as spectrophotometric assay or reverse‐phase high performance liquid chromatography (HPLC) may be used to evaluate phenolic compound induction by these elicitors. In addition, these compounds can be tested on their effects on A. flavus mycelial growth and subsequent aflatoxin production in vitro.

Hence, a study on the possible role of phenols on the natural resistance of peanuts to A. flavus invasion was conducted with the following objectives: 1) to quantitate changes in free and bound phenolic compounds influenced by chitosan, A. flavus, and water activity (Aw) levels by Folin‐Ciocalteu assay; 2) to separate, identify, and quantitate free and bound phenolic acids influenced by elicitors and Aw levels; and 3) to determine the effects of phenolic acids in liquid cultures at different concentrations on mycelial growth and aflatoxin B₁ production by A. flavus.     

Selected bioactivities of Vaccinium berries and other fruit crops in relation to their phenolic contents

Antioxidant activity, urinary tract protective activity, and cardioprotective anti‐platelet effects are among the bioactivities associated with dietary phenolics. These bioactivities were measured in vitro in fruit extracts from seven Vaccinium species and five non‐Vaccinium species to determine their relationship to total phenolic content and to anthocyanin and proanthocyanidin content. Berries belonging to the genus Vaccinium were particularly high in antioxidant activity and urinary tract protective anti‐adhesion activity, while anti‐platelet activity varied among species. There was a positive relationship between antioxidant activity (using the oxygen radical absorbing capacity (ORAC) assay) and both the total phenolic (R² = 0.76) and anthocyanin content (R² = 0.43) of the fruit, although there was no relationship between ORAC and proanthocyanidin content. There were no relationships between anti‐adhesion activity and total phenolic content, anthocyanin content, or proanthocyanidin content. Likewise, no relationships were observed between anti‐platelet activity and total phenolic content, anthocyanin content, or proanthocyanidin content. These results suggest that while antioxidant properties are characteristic of all fruit phenolics, in vitro anti‐adhesion and anti‐platelet bioactivities may be due to less abundant phenolic subgroups. Copyright © 2007 Crown in the right of Canada and Society of Chemical Industry     

Biotechnological production of zeaxanthin by microorganisms

BackgroundZeaxanthin is a natural xanthophyll carotenoid that is widely produced by plants, algae and microorganisms and plays a critical role in the prevention of age-related eye diseases, such as macular degeneration and cataracts. Zeaxanthin is also used in the food, pharmaceutical and nutraceutical industries because of its strong antioxidant and anti-cancer properties. To date, zeaxanthin has been primarily produced by extraction from natural resources, especially plants, which is costly and environmentally unfriendly. The biosynthesis of zeaxanthin by microorganisms has been reported in lots of works to provide another potential route for zeaxanthin production.Scope and approachIn this review, we discuss the zeaxanthin biosynthetic pathway, naturally occurring zeaxanthin-accumulating microorganisms containing bacteria and microalgae, the optimization of fermentation conditions using these microorganisms, and zeaxanthin production using microbial cells factory constructed by metabolic engineering. The different metabolic engineering strategies and the zeaxanthin-accumulating level of the reviewed wild and engineered microorganisms are also considered. Furthermore, this work presents perspectives concerning the microbial production of zeaxanthin, especially the trends to construct the metabolically engineered microorganisms for zeaxanthin production.Key findings and conclusionsTo date, all the reported wild zeaxanthin-accumulating microorganisms belong to either bacteria or microalgae, while most of the reported engineering microorganisms for zeaxanthin production are Escherichia coli or yeast. A feasible strategy for zeaxanthin production is the use of metabolic engineering to construct a zeaxanthin-accumulating microbial cells factories followed by the optimization of fermentation with the engineered strain. Besides the simple overexpression of the biosynthesizing genes, the dynamic regulation of the constructed pathway has also been used for zeaxanthin production by metabolic engineering. Construction of better microbial cells factories which produce more zeaxanthin will profit from the breakthrough of the following fields: Introduction of higher plant zeaxanthin biosynthesizing genes into microorganisms; Characterization of novel zeaxanthin pathway genes from the wild microorganisms producing high level of zeaxanthin; Deep investigation of the farnesyl diphosphate formation pathway; Construction of microbial host with weak antioxidative capacity.     

Determination of some individual phenolic compounds and antioxidant capacity of mead produced from different types of honey

The aim of this study was to promote mead (honey wine) production by testing the appropriateness of different honey varieties which were obtained from the flora of Turkey for the production of mead. Cotton‐Mezda (Gossypium spp.), pine (Pinus spp.) and flower honeys were used in the fermentation studies. Pure culture Saccharomyces cerevisiae yeasts were used in the mead studies. While determining the phenolic contents of meads via HPLC method, five phenolic acids and two flavonoids were used as standards with known antioxidant properties. In addition, total antioxidant activity was analysed in meads using trolox equivalent antioxidant capacity (TEAC). Among the phenolic acids, the most abundant one was protocatechuic acid (75.12–179.03 μg/L) and among flavonoids it was catechin (10.38–125.55 μg/L). It was found out that total phenolic content ranged from 103.56 GAE to 167.89 GAE mg/L. Copyright © 2017 The Institute of Brewing & Distilling     

Lotus Flavonoids and Phenolic Acids: Health Promotion and Safe Consumption Dosages

Nelumbo nucifera Gaertn., also known as the sacred lotus, is extensively cultivated in Southeast Asia, primarily for food and as an herbal medicine. This article reviews studies published between 1995 and 2017, on flavonoid and phenolic acid profiles and contents of 154 different cultivars of lotus. So far, some 12 phenolic acids and 89 to 90 flavonoids (47 flavonols, 25 to 26 flavons, 8 flavan‐3‐ols, 4 flavanons, and 5 anthocyanins) have been isolated from different parts of the lotus plant, including its leaves (whole leaf, leaf pulp, leaf vein, and leaf stalk), seeds (seedpod, epicarp, coat, kernel, and embryo), and flowers (stamen, petal, pistil, and stalk), although not all of them have been quantified. Factors affecting flavonoids and phenolic acid profiles, including types of tissues and extracting factors, are discussed in this review, in order to maximize the application of the lotus and its polyphenols in the food industry. Health promotion activities, attributed to the presence of flavonoids and phenolic acids, are described along with toxicology studies, illustrating appropriate usage and safe consumption dosages of lotus extracts. This review also presents the controversies and discusses the research gaps that limit our ability to obtain a thorough understanding of the bioactivities of lotus extracts.     

Anti-inflammatory potential of mushroom extracts and isolated metabolites

BackgroundIn the recent years natural resources are being in focus due to their great potential to be exploited in the discovery/development of novel bioactive compounds and, among them, mushrooms can be highlighted as alternative sources of anti-inflammatory agents.Scope and approachThe present review reports the anti-inflammatory activity of mushroom extracts and of their bioactive metabolites involved in this bioactive action. Additionally the most common assays used to evaluate mushrooms anti-inflammatory activity were also reviewed, including in vitro studies in cell lines, as well as in animal models in vivo.Key findings and conclusionsThe anti-inflammatory compounds identified in mushrooms include polysaccharides, terpenes, phenolic acids, steroids, fatty acids and other metabolites. Among them, polysaccharides, terpenoids and phenolic compounds seem to be the most important contributors to the anti-inflammatory activity of mushrooms as demonstrated by numerous studies. However, clinical trials need to be conducted in order to confirm the effectiveness of some of these mushroom compounds namely, inhibitors of NF-κB pathway and of cyclooxygenase related with the expression of many inflammatory mediators.     

Bioactive phenolic compounds of cowpeas (Vigna sinensis L). Modifications by fermentation with natural microflora and with Lactobacillus plantarum ATCC 14917

In this work we have determined the phenolic composition of raw cowpeas (Vigna sinensis L) of the variety Carilla by HPLC/PAD/MS and have studied the effect of fermentation, both spontaneous and with Lactobacillus plantarum ATCC 14917, on the phenolic compounds. This variety contains mainly ferulic and p‐coumaric acids esterified with aldaric acids, together with the cis and trans isomers of the corresponding free acids. Hydroxybenzoic acids such as gallic, vanillic, p‐hydroxybenzoic and protocatechuic were also found, along with flavonols such as a myricetin glucoside, mono‐ and diglycosides of quercetin and a quercetin diglycoside acylated with ferulic acid. Fermentation, both spontaneous and inoculated, modifies the content of phenolic compounds, but differently in each case. The antioxidant activity as free radical‐scavenging activity has also been evaluated. Fermentation followed by heating has been shown to be a very effective process to increase the functionality of this variety of V sinensis. For this reason, this cowpea variety could be used as an ingredient to obtain high value‐added flours. Copyright © 2004 Society of Chemical Industry     

CLONING OF A YEAST GENE WHICH CAUSES PHENOLIC OFF-FLAVOURS IN BEER

A gene (POF1) has been cloned, which confers upon yeast (Saccharomyces cerevisiae) the ability to decarboxylate phenolic acids such as ferulic and trans-cinnamic acid. This property was previously shown to be a cause of phenolic off-flavour production in wort fermentations. The identity of the cloned gene was confirmed as POF1 by gene disruption techniques. Southern blotting of total genomic DNA revealed that sequences homologous to POF1 are conserved in Pof^? brewing strains of Sacch. cerevisiae. The transformation of a Pof^? lager strain with the cloned POF1 gene led to the production of an aroma characteristic of a phenolic off-flavour, when the transformed strain was used in wort fermentations. This latter observation suggests that the Pof^? phenotype of brewers' yeast is specifically due to the absence of a functional POF1 gene.     

Fruit Phenolic Composition of Different Elderberry Species and Hybrids

The aim of this study was to investigate a detailed composition and content of phenolic compounds in fruits of 4 elderberry species (Sambucus nigra, S. cerulea, S. ebulus, and S racemosa) and 8 interspecific hybrids. Hydroxycinnamic acids (HCAs) represented the major share of phenolics in analyzed elderberries; caffeoylquinic and p‐coumaroylquinic acids were most abundant. Flavanols (catechin, epicatechin, and different procyanidins) were the second major phenolic group detected in range from 2% to 30% of total analyzed phenolics. From the group of flavonols, 13 different quercetin glycosides, 7 kaempferol glycosides, and 8 isorhamnetin glycosides have been quantified. Rutin was the major flavonol in all studied genotypes. S. ebulus was characterized by the highest level of total HCAs, catechin, epicatechin, and most flavonols. Some elderberry hybrids, for example JA × RAC, CER × NI, and JA × (JA × NI), are perspective for further studies because they have high content of phenolic compounds. The results of research could contribute to breed cultivars, which may prove interesting for food‐processing industries.     

p‐Coumaric acid and its conjugates: dietary sources,pharmacokinetic properties and biological activities

p‐Coumaric acid (4‐hydroxycinnamic acid) is a phenolic acid that has low toxicity in mice (LD₅₀ = 2850 mg kg^?1 body weight), serves as a precursor of other phenolic compounds, and exists either in free or conjugated form in plants. Conjugates of p‐coumaric acid have been extensively studied in recent years due to their bioactivities. In this review, the occurrence, bioavailability and bioaccessibility of p‐coumaric acid and its conjugates with mono‐, oligo‐ and polysaccharides, alkyl alcohols, organic acids, amine and lignin are discussed. Their biological activities, including antioxidant, anti‐cancer, antimicrobial, antivirus, anti‐inflammatory, antiplatelet aggregation, anxiolytic, antipyretic, analgesic, and anti‐arthritis activities, and their mitigatory effects against diabetes, obesity, hyperlipaemia and gout are compared. Cumulative evidence from multiple studies indicates that conjugation of p‐coumaric acid greatly strengthens its biological activities; however, the high biological activity but low absorption of its conjugates remains a puzzle. © 2015 Society of Chemical Industry     

Characterization of Enzyme Released Antioxidant Phenolic Acids and Xylooligosaccharides from Different Graminaceae or Poaceae Members

Xylooligosacchrides (XOS) and phenolic acids were simultaneously produced from hemicelluloses using crude enzyme mixture synthesized by a novel Bacillus subtilis KCX006. The strain synthesized XOS-forming endo-xylanase and de-branching α-L-arabinofuranosidase and esterase but not β-xylosidase. This enzyme mixture can improve the yield of XOS and phenolic acids from xylan due to the absence of hydrolysis of XOS by β-xylosidase and release of phenolic acids by esterase. Hence, the enzyme mixture was tested for simultaneous production of XOS and phenolic acids from xylan (28–35%)-rich Graminaceae or Poaceae plant biomass, such as wheat bran, sugarcane bagasse, bamboo, and rise husk. Hemicellulose fractions of the biomasses were extracted by alkaline treatment and hydrolyzed using crude xylanase mixture. The profiles of XOS and phenolic acids formed were analyzed by HPLC. The lyophilized hydrolytic products were further analysed by ¹H NMR to identify the substitutions in XOS. The observed profile of XOS and phenolic acids varied with the biomass sources. Maximum amounts of XOS (665.2 mg/g dwt) and phenolic acids (89.69 μg/g dwt) were produced from hemicellulose A fractions of sugarcane bagasse and bamboo bagasse, respectively. HPLC and ¹H NMR analysis of XOS revealed the formation of free- and arabino-XOS. Phenolic acids consisted of hydroxycinnamic and hydroxybenzoic acids and the antioxidant activity correlated well with hydroxycinnamic acids content. The crude enzyme of B. subtilis is useful to produce mixture of XOS and phenolic acids from biomass.     

Can plant phenolic compounds reduce Fusarium growth and mycotoxin production in cereals?

ABSTRACT

To assess the in vitro activity of three phenolic acids (ferulic acid, p-hydroxybenzoic acid, vanillic acid) and two flavonols (quercetin, rutin) on mycelial growth and mycotoxin accumulation of Fusarium graminearum (FG), F. langsethiae (FL) and F. poae (FP), two different approaches were chosen. First, grains from oat varieties were inoculated with a suspension of three FL isolates to determine the influence of phenolic compounds on the accumulation of mycotoxins. The oat variety Zorro showed a tendency for lower accumulation of T-2/HT-2, diacetoxyscirpenol and neosolaniol. Second, a mycelium growth assay was conducted to follow FG, FL and FP growth on cereal based media supplemented with phenolic compounds. Increasing concentrations of ferulic acid substantially inhibited growth of FG and FL, while FP growth was reduced to 57%. In contrast, p-hydroxybenzoic acid, vanillic acid, quercetin, and rutin slightly stimulated mycelium growth. Results about mycotoxin production in cereal based media were less conclusive.     

Millet grain phenolics and their role in disease risk reduction and health promotion: A review

Millets rank six in the world cereal grain production. In Africa and Asia, these underutilized grains play a major role in the food security of millions of people. In addition to being a rich source of nutrients, millet grains have an abundance of phytochemicals, particularly phenolic compounds. This review will focus on the bioactivities and health benefits of millet phenolics as revealed by in vitro and in vivo studies. Phenolic compounds in millets are found in the soluble as well as insoluble-bound forms. Both hydroxybenzoic and hydroxycinnamic acids and their derivatives are notably present in different types of millet grains in varying proportion. Meanwhile, flavonoids exist mainly in the free form. A wide variation exists in the phenolic content and antioxidant capacity of millet grains. Further, millet grain phenolics, are bioaccessible, possess bioactivities against several pathophysiological conditions and may serve as potential natural sources of antioxidants in food and biological systems. While this review also shows the existence of a substantial body of evidence for in vitro antioxidant activity of millet grain phenolics, there is a clear gap for in vivo information. However, the use of millets, as nutraceuticals and specialty foods in disease risk reduction and overall health and wellness is warranted.     

Phenolic Composition,Radical Scavenging Activity and an Approach for Authentication of Aronia melanocarpa Berries,Juice, and Pomace

Aronia melanocarpa is a rich source of phenolic compounds like anthocyanins, chlorogenic acids, quercetin derivatives, and proanthocyanidins possessing strong antioxidative potential. The consumption of A. melanocarpa is actually increasing because of the known bioactivity of its phenolic constituents. A. melanocarpa extracts are used as natural colorants and nutraceuticals. Several attempts of adulteration of aronia products have already been reported. In this study, we investigated changes in phenolic composition from berry to juice by HPLC‐PDA, and HPLC‐ESI‐MSⁿ analyses as well as fingerprint profiles for authentication of commercially available aronia products in order to detect possible adulteration. Additionally, the radical scavenging activity of aronia products was determined by using the TEAC (Trolox® equivalent antioxidant capacity) assay. Aronia pomace, a valuable by‐product of juice production, showed the highest phenolic content and possessed the highest radical scavenging activity.