scholarly journals Specificity of Saliva Esterases by Wine Carboxylic Esters and Inhibition by Wine Phenolic Compounds Under Simulated Oral Conditions

2021 ◽  
Vol 8 ◽  
Author(s):  
María Pérez-Jiménez ◽  
Carolina Muñoz-González ◽  
María Ángeles Pozo-Bayón
Keyword(s):  
Phenolic Compounds ◽  
Grape Seed ◽  
Carbon Chain ◽  
Wine Consumption ◽  
Salivary Ph ◽  
Wine Polyphenols ◽  
The Individual ◽  
Carboxylic Esters ◽  
Chain Lengths ◽  
Oral Conditions

The specificity of human esterase activity (EA) from the stimulated (SS) and non-stimulated (NSS) saliva toward different typical wine odorant carboxylic esters and its inhibition by the wine phenolic compounds has been evaluated. For the specificity, six p-nitrophenyl linked esters with different carbon chain lengths (from 2 to 12 carbons) were employed. The five single phenolic compounds (catechin, quercetin, kaempferol, myricetin, and resveratrol) at typical wine concentrations were assayed in the salivary EA inhibition study. Additionally, the inhibition exerted by the mixtures of wine polyphenols was evaluated using four commercial phenolic extracts [a grape seed extract (GSE), the monomers and oligomer fraction of the GSE, and a red wine extract (RWE)]. Finally, the saliva EA under the wine consumption conditions (pH = 5 and 11.3% ethanol) was evaluated. The results showed a higher EA in SS than NSS. It was also shown that the EA was higher toward the smaller than bigger esters regardless of the saliva types (SS or NSS). However, the inhibition exerted on saliva EA by the individual and mixtures of phenolic compounds was proven. Catechin was the phenolic compound that mostly inhibited saliva EA, while resveratrol showed the lowest EA inhibition. This inhibition was mainly related to the concentration of the phenolic compounds, but also with its structure. Finally, under simulated wine consumption, a decrease in EA was produced, which was mainly provoked by the decrease in the salivary pH. Nonetheless, since salivary pH recovers a few seconds after wine consumption, saliva EA might be relevant for the long-lasting perception of wine esters.

The Use of N-alkanes for Estimating Intake and Passage Rate in Horses

1996 ◽  
Vol 1996 ◽  
pp. 98-98
Author(s):  
B M L McLean ◽  
R W Mayes ◽  
F D DeB Hovell
Keyword(s):  
Recent Work ◽  
Chain Length ◽  
Carbon Chain ◽  
Carbon Chain Length ◽  
Passage Rate ◽  
Forage Crops ◽  
Carbon Chains ◽  
Naturally Occurring ◽  
Chain Lengths ◽  
Long Chain

Alkanes occur naturally in all plants, although forage crops tend to have higher alkane contents than cereals. N-alkanes have odd-numbered carbon chains. They are ideal for use as markers in feed trials, because, they are inert, indigestible and naturally occurring, and can be recovered in animal faeces. Synthetic alkanes (even-numbered carbon chains) are available commercially and can also used as external markers. Dove and Mayes (1991) cite evidence indicating that faecal recovery of alkanes in ruminants increases with increasing carbon-chain length. Thus the alkane “pairs” (e.g. C35 & C36, and C32 & C33) are used in calculating intake and digestibility because they are long chain and adjacent to each other. However, recent work by Cuddeford and Mayes (unpublished) has found that in horses the faecal recovery rates are similar regardless of chain lengths.

scholarly journals Terminal Olefin Profiles and Phylogenetic Analyses of Olefin Synthases of Diverse Cyanobacterial Species

2018 ◽  
Vol 84 (13) ◽  
Author(s):  
Tao Zhu ◽  
Thibault Scalvenzi ◽  
Nathalie Sassoon ◽  
Xuefeng Lu ◽  
Muriel Gugger
Keyword(s):  
Fatty Acid ◽  
Genetic Basis ◽  
Carbon Chain ◽  
Fatty Acyl ◽  
Carbon Chain Length ◽  
Substrate Activation ◽  
Chain Length Specificity ◽  
Modular Architectures ◽  
Terminal Olefins ◽  
Chain Lengths

ABSTRACT Cyanobacteria can synthesize alkanes and alkenes, which are considered to be infrastructure-compatible biofuels. In terms of physiological function, cyanobacterial hydrocarbons are thought to be essential for membrane flexibility for cell division, size, and growth. The genetic basis for the biosynthesis of terminal olefins (1-alkenes) is a modular type I polyketide synthase (PKS) termed olefin synthase (Ols). The modular architectures of Ols and structural characteristics of alkenes have been investigated only in a few species of the small percentage (approximately 10%) of cyanobacteria that harbor putative Ols pathways. In this study, investigations of the domains, modular architectures, and phylogenies of Ols in 28 cyanobacterial strains suggested distinctive pathway evolution. Structural feature analyses revealed 1-alkenes with three carbon chain lengths (C 15 , C 17 , and C 19 ). In addition, the total cellular fatty acid profile revealed the diversity of the carbon chain lengths, while the fatty acid feeding assay indicated substrate carbon chain length specificity of cyanobacterial Ols enzymes. Finally, in silico analyses suggested that the N terminus of the modular Ols enzyme exhibited characteristics typical of a fatty acyl-adenylate ligase (FAAL), suggesting a mechanism of fatty acid activation via the formation of acyl-adenylates. Our results shed new light on the diversity of cyanobacterial terminal olefins and a mechanism for substrate activation in the biosynthesis of these olefins. IMPORTANCE Cyanobacterial terminal olefins are hydrocarbons with promising applications as advanced biofuels. Despite the basic understanding of the genetic basis of olefin biosynthesis, the structural diversity and phylogeny of the key modular olefin synthase (Ols) have been poorly explored. An overview of the chemical structural traits of terminal olefins in cyanobacteria is provided in this study. In addition, we demonstrated by in vivo fatty acid feeding assays that cyanobacterial Ols enzymes might exhibit substrate carbon chain length specificity. Furthermore, by performing bioinformatic analyses, we observed that the substrate activation domain of Ols exhibited features typical of a fatty acyl-adenylate ligase (FAAL), which activates fatty acids by converting them to fatty acyl-adenylates. Our results provide further insight into the chemical structures of terminal olefins and further elucidate the mechanism of substrate activation for terminal olefin biosynthesis in cyanobacteria.

scholarly journals Biochemical Characterization of CYP505D6, a Self-Sufficient Cytochrome P450 from the White-Rot FungusPhanerochaete chrysosporium

2018 ◽  
Vol 84 (22) ◽  
Author(s):  
Kiyota Sakai ◽  
Fumiko Matsuzaki ◽  
Lisa Wise ◽  
Yu Sakai ◽  
Sadanari Jindou ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Cytochrome P450 ◽  
Phanerochaete Chrysosporium ◽  
Carbon Chain ◽  
Fatty Alcohols ◽  
White Rot ◽  
Wild Type ◽  
Content Type ◽  
Attractive Candidate ◽  
Chain Lengths

ABSTRACTThe activity of a self-sufficient cytochrome P450 enzyme, CYP505D6, from the lignin-degrading basidiomycetePhanerochaete chrysosporiumwas characterized. Recombinant CYP505D6 was produced inEscherichia coliand purified. In the presence of NADPH, CYP505D6 used a series of saturated fatty alcohols with C9–18carbon chain lengths as the substrates. Hydroxylation occurred at the ω-1 to ω-6 positions of such substrates with C9–15carbon chain lengths, except for 1-dodecanol, which was hydroxylated at the ω-1 to ω-7 positions. Fatty acids were also substrates of CYP505D6. Based on the sequence alignment, the corresponding amino acid of Tyr51, which is located at the entrance to the active-site pocket in CYP102A1, was Val51 in CYP505D6. To understand the diverse hydroxylation mechanism, wild-type CYP505D6 and its V51Y variant and wild-type CYP102A1 and its Y51V variant were generated, and the products of their reaction with dodecanoic acid were analyzed. Compared with wild-type CYP505D6, its V51Y variant generated few products hydroxylated at the ω-4 to ω-6 positions. The products generated by wild-type CYP102A1 were hydroxylated at the ω-1 to ω-4 positions, whereas its Y51V variant generated ω-1 to ω-7 hydroxydodecanoic acids. These observations indicated that Val51 plays an important role in determining the regiospecificity of fatty acid hydroxylation, at least that at the ω-4 to ω-6 positions. Aromatic compounds, such as naphthalene and 1-naphthol, were also hydroxylated by CYP505D6. These findings highlight a unique broad substrate spectrum of CYP505D6, rendering it an attractive candidate enzyme for the biotechnological industry.IMPORTANCEPhanerochaete chrysosporiumis a white-rot fungus whose metabolism of lignin, aromatic pollutants, and lipids has been most extensively studied. This fungus harbors 154 cytochrome P450-encoding genes in the genome. As evidenced in this study,P. chrysosporiumCYP505D6, a fused protein of P450 and its reductase, hydroxylates fatty alcohols (C9–15) and fatty acids (C9–15) at the ω-1 to ω-7 or ω-1 to ω-6 positions, respectively. Naphthalene and 1-naphthol were also hydroxylated, indicating that the substrate specificity of CYP505D6 is broader than those of the known fused proteins CYP102A1 and CYP505A1. The substrate versatility of CYP505D6 makes this enzyme an attractive candidate for biotechnological applications.

scholarly journals SELECTIVITY OF CANDIDA RUGOSA LIPASE IMMOBILIZED ONTO LAYERED DOUBLE HYDROXIDES AS CATALYST IN SYNTHESIS OF FATTY ACID ESTERS

2016 ◽  
Vol 78 (5-6) ◽  
Author(s):  
Mohd Basyaruddin Abdul Rahman ◽  
Siti Salhah Othman ◽  
Noor Mona Md Yunus
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Chain Length ◽  
Candida Rugosa ◽  
Candida Rugosa Lipase ◽  
Carbon Chain ◽  
Fatty Acid Esters ◽  
Carbon Chain Length ◽  
Chain Lengths ◽  
Acid Esters

The enzymatic selectivity of Lipase from Candida rugosa immobilized onto a calcined layered double hydroxide (CLDHs-CRL) towards the chain-length of fatty acids and alcohols in the synthesis of fatty acid esters was investigated.  The results showed that CMAN-CRL catalyzed the esterification process with fatty acids of medium chain lengths (C10-C14) effectively while, CNAN-CRL and CZAN-CRL exhibited high percentage conversion in fatty acids with carbon chain lengths of C8-C12 and C10-C18, respectively. In the alcohol selectivity study, CMAN-CRL showed high selectivity toward alcohols with carbon chain lengths of C4, C6 and C10.  On the other hand, both CNAN-CRL and CZAN-CRL exhibited rather low selectivity towards longer carbon chain length of alcohols. 

scholarly journals Recovery of Oligomeric Proanthocyanidins and Other Phenolic Compounds with Established Bioactivity from Grape Seed By-Products

Molecules ◽  
2019 ◽  
Vol 24 (4) ◽  
pp. 677 ◽  
Author(s):  
Federica Pasini ◽  
Fabio Chinnici ◽  
Maria Caboni ◽  
Vito Verardo
Keyword(s):  
Phenolic Compounds ◽  
Grape Seed ◽  
Grape Pomace ◽  
Grape Seeds ◽  
Esi Ms ◽  
Oligomeric Proanthocyanidins ◽  
Main Class ◽  
Normal Phase Hplc ◽  
By Products

Grape seeds are a copious part of the grape pomace produced by wine and juice industry and they represent an interesting source of phenolic compounds. Proanthocyanidins (PAs) are the main class of grape seed phenols and are important dietary supplements for their well-known beneficial properties. In this study enriched extracts obtained from Chardonnay and Pignoletto grape seeds were characterized for their proanthocyanidins and other minor phenolic compounds content and composition. Seed PAs were fractionated using Sephadex LH-20, using different ethanol aqueous solutions as mobile phase and analysed by normal phase HPLC-FLD-ESI-MS. Monomers, oligomers up to dodecamers and polymers were recorded in all samples. For both cultivars, the extracts showed a high content in PAs. The determination of other phenolic compounds was carried out using a HPLC-QqQ-ESI-MS and Chardonnay samples reported a greater content compared to Pignoletto samples. Contrary to PAs fraction, extracts obtained with ethanol/water 50/50 (v/v) presented a significant higher phenolic content than the others.

scholarly journals Advanced Analytical Methods for Phenolics in Fruits

2018 ◽  
Vol 2018 ◽  
pp. 1-6 ◽  
Author(s):  
Nesibe Ebru Kafkas ◽  
Müberra Kosar ◽  
Ayşe Tülin Öz ◽  
Alyson E. Mitchell
Keyword(s):  
Phenolic Compounds ◽  
Value Added ◽  
Biological Tissues ◽  
Carbon Chain ◽  
Polyphenolic Compounds ◽  
Hydroxyl Groups ◽  
Plant Metabolites ◽  
Secondary Plant Metabolites ◽  
Extraction Separation ◽  
Health Promoting

Phenolic compounds are a group of secondary plant metabolites, many with health-promoting properties that are present in all parts of plants. They have an aromatic structure, including either one or more hydroxyl groups giving them the ability to stabilize free radicals and protect biological tissues against damage related to reactive oxygen species. Phenolic compounds are concentrated in the fruit of plants, and therefore, the fruit can be an important dietary source of these phytochemicals, which exist as monomers, or bound to one another. Polyphenolic compounds are classified into different subclasses based upon the number of phenol ring systems that they contain, saturation, and length of the carbon chain that bind the rings to one another. The phenolic acids present in fruit tissues protect the plant against disease, infections, UV radiation, and insect damage. For this reason, the beneficiary effects of phenolic compounds are continually being investigated for their health-promoting properties and for meeting increased consumer demand for healthy nutritious food. Due to the functional properties of polyphenolic compounds, there is increased interest on improving extraction, separation, and quantification techniques of these valuable bioactive compounds, so they can be used as value-added ingredients in foods, pharmaceuticals, and cosmetics. This review provides information on the most advanced methods available for the analysis of phenolics in fruits.

scholarly journals The Impact of Dietary Grape Seed Meal on Healthy and Aflatoxin B1 Afflicted Microbiota of Pigs after Weaning

Toxins ◽  
2019 ◽  
Vol 11 (1) ◽  
pp. 25 ◽  
Author(s):  
Iulian A. Grosu ◽  
Gina C. Pistol ◽  
Ionelia Taranu ◽  
Daniela E. Marin
Keyword(s):  
Large Intestine ◽  
Relative Abundance ◽  
Aflatoxin B1 ◽  
Illumina Miseq ◽  
Grape Seed ◽  
Antagonistic Effect ◽  
Seed Meal ◽  
Control Group ◽  
The Individual ◽  
The Impact

The study investigated the effect of grape seed (GS) meal, aflatoxin (AFB1), or their combination on the large intestine microbiota of weanling piglets. Twenty-four piglets were allocated into four groups based on diet composition: (1) Control group; (2) AFB1 (320 g/kg feed) group; (3) GS group (8% inclusion in the diet); (4) AFB1 + GS group. After 30 days of experiment, the colon content was used for microbiota analyses; after isolation of total bacterial genomic DNA, V3/V4 regions of the 16S rRNA amplicons were sequenced using the Illumina MiSeq platform. The raw sequences were analyzed using the v.1.9.1 QIIME pipeline software. 157 numbers of OTUs were identified among all four dietary groups with 26 of them being prevalent above 0.05% in the total relative abundance. GS and AFB1 increase the relative abundance of phylum Bacteroidetes and Proteobacteria, while decreasing the Firmicutes abundance in a synergic manner as compared with the individual treatments. An additive or synergistic action of the two treatments was identified for Lactobacillus, Prevotella and Campylobacter, while rather an antagonistic effect was observed on Lachnospira. The action mechanisms of aflatoxin B1 and grape seed meal that drive the large intestine microbiota to these changes are not known and need further investigations.

scholarly journals Variability in the Qualitative and Quantitative Composition and Content of Phenolic Compounds in the Fruit of Introduced American Cranberry (Vaccinium macrocarpon Aiton)

Plants ◽  
2020 ◽  
Vol 9 (10) ◽  
pp. 1379
Author(s):  
Ieva Gudžinskaitė ◽  
Elicija Stackevičienė ◽  
Mindaugas Liaudanskas ◽  
Kristina Zymonė ◽  
Vaidotas Žvikas ◽  
...  
Keyword(s):  
Phenolic Compounds ◽  
Vaccinium Macrocarpon ◽  
Quantitative Composition ◽  
Qualitative And Quantitative ◽  
American Cranberry ◽  
Fruit Samples ◽  
Phytochemical Profile ◽  
Ethanol Extracts ◽  
The Individual

The aim of this study was to determine the composition and content of phenolic compounds in ethanol extracts of eight different cultivars of American cranberry (Vaccinium macrocarpon Aiton) fruit using spectrophotometric and UPLC-ESI-MS/MS analysis and to evaluate the antioxidant activity in vitro of these extracts. The highest total amount of phenolic compounds evaluated via Folin–Ciocalteu spectrophotometry was detected in American cranberry fruit samples of the ‘Bain’ clone, and the highest total amount of flavonoids was found in samples of the ‘Drever’ and ‘Baiwfay’ cultivars. The highest total amount of the individual phenolic compounds (519.53 ± 25.12 mg/g DW) identified and quantitatively evaluated via chromatography was detected in samples of the ‘Searles’ cranberry cultivar. In the studied cranberry samples, the predominant phenolic compounds were hyperoside, quercetin, and procyanidin A2, while the amounts of other compounds were significantly lower. HCA and PCA revealed that ‘Woolman’, ‘Holliston’, ‘Pilgrim, and ‘Searles’ fruit samples had different quantitative content of phenolic compounds from other cranberry cultivars. Meanwhile, fruit of ‘Baiwfay’, ‘Drever’, ‘Bain’, and ‘Bergman’ were similar in their phytochemical profile.

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