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Transformation of Oligomeric Ellagitannins, Typical for Rubus and Fragaria Genus, during Strong Acid Hydrolysis.

ABSTRACT: The strong acid hydrolysis analysis of galloyl-O-digalloyl-type ellagitannins (ETs), lambertianin C (LC) and sanguiin H-6, and dehydrodigalloyl-type ET, agrimoniin (AM), was performed. A quantitative and qualitative analysis of the degradation products of individual ETs was conducted using high-performance liquid chromatography-diode array detecto-electrospray ionization interface-mass spectrometry (HPLC-DAD-ESI-MS). The data indicate that ETs undergo multidirectional changes in a strongly acidic environment, where the process of successive hydrolysis of ester bonds to form ellagic acid (EA) is the dominant phenomenon in the initial phase of the reaction, followed by the depolymerization process and the formation of low-molecular ETs. Characteristic products of ET hydrolysis were distinguished: for LC: dimeric ET plus one galloyl moiety without one EA moiety (M = 1736 Da), for all analyzed ETs: sanguisorbic acid dilactone (M = 470 Da), and for AM: dehydrodigallic acid (M = 338 Da). The research carried out has allowed to create a database of possible products and routes of transformation of individual ETs, which should facilitate future research on the transformation of ETs, including potential prohealth properties of its breakdown products, under conditions occurring during food processing or digestion.

SUBMITTER: Macierzynski J

PROVIDER: S-EPMC7458417 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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Transformation of Oligomeric Ellagitannins, Typical for Rubus and Fragaria Genus, during Strong Acid Hydrolysis.

Macierzyński Jakub J Sójka Michał M Kosmala Monika M Karlińska Elżbieta E

Journal of agricultural and food chemistry 20200721 31

The strong acid hydrolysis analysis of galloyl-O-digalloyl-type ellagitannins (ETs), lambertianin C (LC) and sanguiin H-6, and dehydrodigalloyl-type ET, agrimoniin (AM), was performed. A quantitative and qualitative analysis of the degradation products of individual ETs was conducted using high-performance liquid chromatography-diode array detecto-electrospray ionization interface-mass spectrometry (HPLC-DAD-ESI-MS). The data indicate that ETs undergo multidirectional changes in a strongl ...[more]

PMID: 32648752

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Project description:Ellagitannins have shown anti-inflammatory and anti-Helicobacter pylori properties; however, their anti-inflammatory activity at gastric level was not previously investigated. The aim of this research was to evaluate the effects of ellagitannins from Rubus berries on gastric inflammation. Ellagitannin enriched extracts (ETs) were prepared from Rubus fruticosus L. (blackberry) and Rubus idaeus L. (raspberry). The anti-inflammatory activity was tested on gastric cell line AGS stimulated by TNF-α and IL-1β for evaluating the effect on NF-kB driven transcription, nuclear translocation and IL-8 secretion. In vivo the protective effect of ellagitannins was evaluated in a rat model of ethanol-induced gastric lesions. Rats were treated orally for ten days with 20 mg/kg/day of ETs, and ethanol was given one hour before the sacrifice. Gastric mucosa was isolated and used for the determination of IL-8 release, NF-kB nuclear translocation, Trolox equivalents, superoxide dismutase and catalase activities. In vitro, ETs inhibited TNF-α induced NF-kB driven transcription (IC₅₀: 0.67-1.73 µg/mL) and reduced TNF-α-induced NF-kB nuclear translocation (57%-67% at 2 µg/mL). ETs inhibited IL-8 secretion induced by TNF-α and IL-1β at low concentrations (IC₅₀ range of 0.7-4 µg/mL). Sanguiin H-6 and lambertianin C, the major ETs present in the extracts, were found to be responsible, at least in part, for the effect of the mixtures. ETs of blackberry and raspberry decreased Ulcer Index by 88% and 75% respectively and protected from the ethanol induced oxidative stress in rats. CINC-1 (the rat homologue of IL-8) secretion in the gastric mucosa was reduced in the animals receiving blackberry and raspberry ETs. The effect of ETs on CINC-1 was associated to a decrease of NF-κB nuclear translocation in ETs treated animals. The results of the present study report for the first time the preventing effect of ETs in gastric inflammation and support for their use in dietary regimens against peptic ulcer.

Project description:Here, we report three new Acidiphilium genomes, reclassified existing Acidiphilium species, and performed the first comparative genomic analysis on Acidiphilium in an attempt to address the metabolic potential, ecological functions, and evolutionary history of the genus Acidiphilium In the genomes of Acidiphilium, we found an abundant repertoire of horizontally transferred genes (HTGs) contributing to environmental adaption and metabolic expansion, including genes conferring photosynthesis (puf, puh), CO2 assimilation (rbc), capacity for methane metabolism (mmo, mdh, frm), nitrogen source utilization (nar, cyn, hmp), sulfur compound utilization (sox, psr, sqr), and multiple metal and osmotic stress resistance capacities (czc, cop, ect). Additionally, the predicted donors of horizontal gene transfer were present in a cooccurrence network of Acidiphilium Genome-scale positive selection analysis revealed that 15 genes contained adaptive mutations, most of which were multifunctional and played critical roles in the survival of extreme conditions. We proposed that Acidiphilium originated in mild conditions and adapted to extreme environments such as acidic mineral sites after the acquisition of many essential functions.IMPORTANCE Extremophiles, organisms that thrive in extreme environments, are key models for research on biological adaption. They can provide hints for the origin and evolution of life, as well as improve the understanding of biogeochemical cycling of elements. Extremely acidophilic bacteria such as Acidiphilium are widespread in acid mine drainage (AMD) systems, but the metabolic potential, ecological functions, and evolutionary history of this genus are still ambiguous. Here, we sequenced the genomes of three new Acidiphilium strains and performed comparative genomic analysis on this extremely acidophilic bacterial genus. We found in the genomes of Acidiphilium an abundant repertoire of horizontally transferred genes (HTGs) contributing to environmental adaption and metabolic ability expansion, as indicated by phylogenetic reconstruction and gene context comparison. This study has advanced our understanding of microbial evolution and biogeochemical cycling in extreme niches.

Dataset Information

Transformation of Oligomeric Ellagitannins, Typical for Rubus and Fragaria Genus, during Strong Acid Hydrolysis.

Publications

Transformation of Oligomeric Ellagitannins, Typical for <i>Rubus</i> and <i>Fragaria</i> Genus, during Strong Acid Hydrolysis.

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