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The use and production of chemical compounds are subjected to strong legislative pressure. Chemical toxicity and adverse effects derived from exposure to chemicals are key regulatory aspects for a multitude of industries, such as chemical, pharmaceutical, or food, due to direct harm to humans, animals, plants, or the environment. Simultaneously, there are growing demands on the authorities to replace traditional in vivo toxicity tests carried out on laboratory animals (e.g., European Union REACH/3R principles, Tox21 and ToxCast by the U.S. government, etc.) with in silica computational models. This is not only for ethical aspects, but also because of its greater economic and time efficiency, as well as more recently because of their superior reliability and robustness than in vivo tests, mainly since the entry into the scene of artificial intelligence (AI)‐based models, promoting and setting the necessary requirements that these new in silico methodologies must meet. This review offers a multidisciplinary overview of the state of the art in the application of AI‐based methodologies for the fulfillment of regulatory‐related toxicological issues. This article is categorized under: Data Science > Chemoinformatics Data Science > Artificial Intelligence/Machine Learning
Efrén Pérez Santín; Raquel Rodríguez Solana; Mariano González García; María Del Mar García Suárez; Gerardo David Blanco Díaz; María Dolores Cima Cabal; José Manuel Moreno Rojas; José Ignacio López Sánchez. Toxicity prediction based on artificial intelligence: A multidisciplinary overview. WIREs Computational Molecular Science 2021, 11, e1516 .
AMA StyleEfrén Pérez Santín, Raquel Rodríguez Solana, Mariano González García, María Del Mar García Suárez, Gerardo David Blanco Díaz, María Dolores Cima Cabal, José Manuel Moreno Rojas, José Ignacio López Sánchez. Toxicity prediction based on artificial intelligence: A multidisciplinary overview. WIREs Computational Molecular Science. 2021; 11 (5):e1516.
Chicago/Turabian StyleEfrén Pérez Santín; Raquel Rodríguez Solana; Mariano González García; María Del Mar García Suárez; Gerardo David Blanco Díaz; María Dolores Cima Cabal; José Manuel Moreno Rojas; José Ignacio López Sánchez. 2021. "Toxicity prediction based on artificial intelligence: A multidisciplinary overview." WIREs Computational Molecular Science 11, no. 5: e1516.
BACKGROUND Mentha pulegium is an aromatic and medicinal plant used in different Mediterranean herb‐based liqueurs, whose phytochemical composition depends on the elaboration technique used. The aim of this work was to investigate differences in the sensory, chemical, and biological characteristics of pennyroyal liqueurs elaborated by hydro‐alcoholic (HI) and aqueous (AI) infusions, percolation (P), maceration (M), and distillation (D) techniques, and by the mixture of spirit with pennyroyal essential oil (EO). The volatile composition determined by gas chromatography–mass spectrometry (GC–MS) and gas chromatography coupled to flame ionization detection (GC–FID), the total phenolic (TPC) and flavonoid (TFC) contents, the antioxidant (AC), and enzyme (α‐glucosidase, tyrosinase, and acetylcholinesterase) inhibitory capacities, and the sensory analysis by napping, were evaluated in the liqueurs obtained. RESULTS Monoterpenes and sesquiterpenes were the main volatiles present in liqueurs. The M, P, HI, and AI liqueurs showed the highest TPC, TFC, and AC values; and pulegone, the main hepatotoxic chemotype, was found in concentrations that gave rise to concern. The D and EO liqueurs stand out for their acceptable pulegone content and greater tyrosinase inhibition. Similar liqueur classifications were achieved by sensory analyses, and physico‐chemical and biological analyses using multiple factor and principal component analyses, respectively. CONCLUSION These results are an important contribution to the identification of the most appropriate elaboration conditions for herbal liqueurs with the healthiest chemical composition and functional properties. © 2020 Society of Chemical Industry
Raquel Rodríguez‐Solana; Eduardo Esteves; Inês Mansinhos; Sandra Gonçalves; Efrén Pérez‐Santín; Ludovina Galego; Anabela Romano. Influence of elaboration process on chemical, biological, and sensory characteristics of E uropean pennyroyal liqueurs. Journal of the Science of Food and Agriculture 2020, 101, 4076 -4089.
AMA StyleRaquel Rodríguez‐Solana, Eduardo Esteves, Inês Mansinhos, Sandra Gonçalves, Efrén Pérez‐Santín, Ludovina Galego, Anabela Romano. Influence of elaboration process on chemical, biological, and sensory characteristics of E uropean pennyroyal liqueurs. Journal of the Science of Food and Agriculture. 2020; 101 (10):4076-4089.
Chicago/Turabian StyleRaquel Rodríguez‐Solana; Eduardo Esteves; Inês Mansinhos; Sandra Gonçalves; Efrén Pérez‐Santín; Ludovina Galego; Anabela Romano. 2020. "Influence of elaboration process on chemical, biological, and sensory characteristics of E uropean pennyroyal liqueurs." Journal of the Science of Food and Agriculture 101, no. 10: 4076-4089.
Carob liqueur is a traditional Mediterranean alcoholic beverage obtained via a wide range of production techniques contributing to the different organoleptic attributes of the final product. The aim of this research was to evaluate the stability of the chemical composition and biological capacities (antioxidant and enzyme inhibition) under in vitro simulated gastrointestinal digestion of liqueurs prepared by flavouring the fig spirit with carob pulp by maceration, distillation, percolation, or aqueous and hydro-alcoholic infusions. For this purpose, the phenolic and furanic compositions, the total phenolic (TPC) and flavonoid (TFC) contents, antioxidant capacity (AC), and enzyme inhibitory potential against acethylcholinesterase, tyrosinase, α-glucosidase and α-amylase enzymes were evaluated. The content of gallic acid decreased after gastrointestinal digestion, while TPC, TFC, and AC significantly increased after each digestion phase. Overall, no significantly different enzyme inhibitions (p < 0.05) were observed among digested liqueurs, with moderate inhibition against acethylcholinesterase and tyrosinase (enzymes related with neurodegenerative diseases), and potent and low inhibitory capacities for α-glucosidase and α-amylase, respectively (ideal conditions employed in antidiabetic therapy). The study indicates that hydro-alcoholic infusion and maceration were the most appropriate methods to obtain liqueurs with higher values of the aforementioned parameters and safe levels of toxic furanics.
Raquel Rodríguez-Solana; Natacha Coelho; Antonio Santos-Rufo; Sandra Gonçalves; Efrén Pérez-Santín; Anabela Romano. The Influence of In Vitro Gastrointestinal Digestion on the Chemical Composition and Antioxidant and Enzyme Inhibitory Capacities of Carob Liqueurs Obtained with Different Elaboration Techniques. Antioxidants 2019, 8, 563 .
AMA StyleRaquel Rodríguez-Solana, Natacha Coelho, Antonio Santos-Rufo, Sandra Gonçalves, Efrén Pérez-Santín, Anabela Romano. The Influence of In Vitro Gastrointestinal Digestion on the Chemical Composition and Antioxidant and Enzyme Inhibitory Capacities of Carob Liqueurs Obtained with Different Elaboration Techniques. Antioxidants. 2019; 8 (11):563.
Chicago/Turabian StyleRaquel Rodríguez-Solana; Natacha Coelho; Antonio Santos-Rufo; Sandra Gonçalves; Efrén Pérez-Santín; Anabela Romano. 2019. "The Influence of In Vitro Gastrointestinal Digestion on the Chemical Composition and Antioxidant and Enzyme Inhibitory Capacities of Carob Liqueurs Obtained with Different Elaboration Techniques." Antioxidants 8, no. 11: 563.
Thymus lotocephalus G. Lopez & R. Morales is an aromatic species endemic to the south of Portugal with medicinal properties. The aim of this work was to evaluate the effect of elicitors, cytokinin, and different sucrose concentrations on chemical composition and antioxidant activity of extracts from in vitro regenerated shoots. Elicitors (YE: yeast extract, salicylic acid, and AgNO3) were added directly to the medium. Phytochemical analysis include evaluation of total phenolic (TPC), flavonoid (TFC), and rosmarinic acid (RAC) contents. The TPCs and TFCs were determined by Folin-Ciocalteu and aluminum chloride colorimetric assays, respectively. Rosmarinic acid (RA), the main compound found in the studied extracts, was quantified by liquid chromatography-photodiode array detector. Results showed that the cytokinin benzyladenine has an inhibitory effect on TPC, TFC and RAC, as well as on antioxidant activity. TPC was only significantly improved by the presence of YE (from 95.49 ± 3.34 to 118.34 ± 6.24 mgGAE/gextract) and TFCs were not affected by elicitation. The increase in sucrose concentration, from 2 to 4%, and the three elicitors tested, particularly YE, enhanced RACs (from 48.61 ± 0.09 in the control medium to 78.57 ± 0.99 mg/gextract in YE-elicited medium). In accordance with these results, the antioxidant activity measured by 2,2-diphenyl-1-picrylhydrazyl, 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), and ferric reducing antioxidant power assays was significantly greater in extracts from elicited shoots. Overall, the results obtained suggest that shoots of T. lotocephalus are a good source of antioxidant compounds and showed that the production of RA can be promoted by altering in vitro culture conditions.
Sandra Gonçalves; Inês Mansinhos; Raquel Rodríguez-Solana; Efrén Pérez Santín; Natacha Coelho; Anabela Romano. Elicitation improves rosmarinic acid content and antioxidant activity in Thymus lotocephalus shoot cultures. Industrial Crops and Products 2019, 137, 214 -220.
AMA StyleSandra Gonçalves, Inês Mansinhos, Raquel Rodríguez-Solana, Efrén Pérez Santín, Natacha Coelho, Anabela Romano. Elicitation improves rosmarinic acid content and antioxidant activity in Thymus lotocephalus shoot cultures. Industrial Crops and Products. 2019; 137 ():214-220.
Chicago/Turabian StyleSandra Gonçalves; Inês Mansinhos; Raquel Rodríguez-Solana; Efrén Pérez Santín; Natacha Coelho; Anabela Romano. 2019. "Elicitation improves rosmarinic acid content and antioxidant activity in Thymus lotocephalus shoot cultures." Industrial Crops and Products 137, no. : 214-220.
BACKGROUND The production of the traditional carob liquor from Algarve (Portugal) depends on numerous factors such as carob processing, variety and maceration conditions. An experimental design with 36 runs was created to evaluate the effect of the roasting temperature, particle size, variety of carob and time of maceration on several parameters of carob liquors as gallic acid and total phenolic content, the furanic composition (furfural and 5‐(hydroxymethyl)furfural), browning index and in vitro antioxidant capacity. RESULTS The results revealed that carob variety was the independent variable with the greatest effect on antioxidant capacity, total phenolic and gallic acid content. In particular, AIDA liquors presented the highest results, mainly those prepared with unroasted carob. Meanwhile, Galhosa and Mulata liquors showed the greatest concentrations when the carob pulp was roasted at 150 °C. The furanic composition and browning index were greatly influenced by the carob roasting degree. CONCLUSION The levels of the main toxic furanics present in carob liquors, furfural and 5‐(hydroxymethyl)furfural, suggest a safe consumption of these beverages even in samples of carobs with the maximum roasting degree. The smallest carob particle size favoured the highest phenolic extraction, while the longest maceration periods decreased the concentration of the toxic furanic compounds studied. This article is protected by copyright. All rights reserved.
Raquel Rodríguez-Solana; José Manuel Salgado; Efrén Pérez-Santín; Anabela Romano. Effect of carob variety and roasting on the antioxidant capacity, and the phenolic and furanic contents of carob liquors. Journal of the Science of Food and Agriculture 2018, 99, 2697 -2707.
AMA StyleRaquel Rodríguez-Solana, José Manuel Salgado, Efrén Pérez-Santín, Anabela Romano. Effect of carob variety and roasting on the antioxidant capacity, and the phenolic and furanic contents of carob liquors. Journal of the Science of Food and Agriculture. 2018; 99 (6):2697-2707.
Chicago/Turabian StyleRaquel Rodríguez-Solana; José Manuel Salgado; Efrén Pérez-Santín; Anabela Romano. 2018. "Effect of carob variety and roasting on the antioxidant capacity, and the phenolic and furanic contents of carob liquors." Journal of the Science of Food and Agriculture 99, no. 6: 2697-2707.
Fig fruits (Ficus carica L.) are used in several Mediterranean countries to produce alcoholic spirits, with either plurivarietal dried figs or, monovarietal fresh figs as the raw material. To determine the influence of different varietal attributes and production methods on the quality of fig spirits, we analyzed the volatile compounds that contribute to the aroma and organoleptic characteristics of spirits derived from eight Portuguese varieties of fresh figs, as well as mixtures of dried figs processed in the laboratory and plurivarietal fig spirits already in the market. The quantification of major and minor volatiles by GC-FID revealed that the plurivarietal dried fig spirits contained greater quantities of short-chain fatty acid esters and higher alcohols (associated with poor-quality spirits) and compounds with a negative influence on aroma and flavor (such as ethyl lactate, ethyl acetate and diethyl succinate) than the fresh fig spirits. HS-SPME/GC–MS analysis detected 130 volatile compounds, among which the esters ethyl decanoate, ethyl octanoate and ethyl dodecanoate, the aldehydes benzaldehyde and furfural, the monoterpene limonene and the norisoprenoide β-damascenone were common constituents in most of the spirits. The volatile profile of all dried fig distillates was similar and diverse, reflecting the plurivarietal origin, whereas the monovarietal fresh fig spirits produced distinct profiles (sufficient for varietal chemical differentiation), with Burjassote branco distillates containing the greatest number of volatile compounds. This volatile analysis provides a way to determine the quality of fig spirits objectively and to develop spirits with novel characteristics for the market.
Raquel Rodríguez-Solana; Ludovina R. Galego; Efrén Pérez-Santín; Anabela Romano. Production method and varietal source influence the volatile profiles of spirits prepared from fig fruits (Ficus carica L.). European Food Research and Technology 2018, 244, 2213 -2229.
AMA StyleRaquel Rodríguez-Solana, Ludovina R. Galego, Efrén Pérez-Santín, Anabela Romano. Production method and varietal source influence the volatile profiles of spirits prepared from fig fruits (Ficus carica L.). European Food Research and Technology. 2018; 244 (12):2213-2229.
Chicago/Turabian StyleRaquel Rodríguez-Solana; Ludovina R. Galego; Efrén Pérez-Santín; Anabela Romano. 2018. "Production method and varietal source influence the volatile profiles of spirits prepared from fig fruits (Ficus carica L.)." European Food Research and Technology 244, no. 12: 2213-2229.
This study evaluates the antioxidant properties and ACE inhibition capacities of eight individual flavonoids before and after incubation with Bifidobacterium animalis ssp. lactis [email protected]®. Changes in flavonoid content and the survival of the probiotics, incubated in individual flavonoid solutions as the only source of carbon, were also determined. The glycosylated flavonoids permitted a higher survival rate of the probiotic bacteria with survival percentages above 50% at 48 h of incubation. The incubation of B. animalis B94 with individual catechins would supposedly produce an increase in all the biological activities tested (ABTS, FRAP and ACE inhibition), but the increments were minor or imperceptible in the flavonol solutions. Epigallocatechin, catechin and epicatechin solutions registered the most important changes in ABTS, FRAP and ACE inhibition capacity, in some cases even doubling their biological activities after incubation with the bacteria. These results are encouraging as the incorporation of B. animalis B94 in various polyphenol-rich foods could be a way of improving the antioxidant properties of the foods. In addition, the polyphenol-rich food could act as a matrix for probiotic strains. © 2014 Elsevier Ltd.Peer Reviewe
Ana M. López de Lacey; Efrén Pérez-Santín; M. Elvira López-Caballero; Pilar Montero. Biotransformation and resulting biological properties of green tea polyphenols produced by probiotic bacteria. LWT - Food Science and Technology 2014, 58, 633 -638.
AMA StyleAna M. López de Lacey, Efrén Pérez-Santín, M. Elvira López-Caballero, Pilar Montero. Biotransformation and resulting biological properties of green tea polyphenols produced by probiotic bacteria. LWT - Food Science and Technology. 2014; 58 (2):633-638.
Chicago/Turabian StyleAna M. López de Lacey; Efrén Pérez-Santín; M. Elvira López-Caballero; Pilar Montero. 2014. "Biotransformation and resulting biological properties of green tea polyphenols produced by probiotic bacteria." LWT - Food Science and Technology 58, no. 2: 633-638.
A functional concentrate rich in proteins and lipids was obtained from an industrial shrimp cooking juice by using a centrifugal separator, and it was characterized in terms of chemical composition parameters and functional or biological activity (antioxidant and ACE-inhibitory capacities). The concentrate presented 116g/kg protein, 135g/kg crude fat and ash content less than 10g/kg, with predominance of Na ions, followed by K, Ca, Mg, Cu, Fe, Zn and Mn. A relative abundance of glucose, glycerol, polyalcohols, acetate and phosphate was found. The antioxidant (as determined by ABTS, FRAP, chelating and photoluminescence assays) and ACE-inhibitory capacities of the material recovered from the shrimp cooking juice were strongly related to the presence of small peptides (1355-502Da), with a clear predominance of Gly, Pro, Glu, Asp and Arg. Other antioxidants, such as free astaxanthin (cis and trans isomers) and derived esters, were also detected. © 2013 Elsevier Ltd.This research was financed by the Spanish Ministry of Economy and Competitiveness through project AGL2011-27607.Peer Reviewe
Efrén Pérez Santín; M.M. Calvo; M.E. López-Caballero; P. Montero; M. Carmen Gómez-Guillén. Compositional properties and bioactive potential of waste material from shrimp cooking juice. LWT 2013, 54, 87 -94.
AMA StyleEfrén Pérez Santín, M.M. Calvo, M.E. López-Caballero, P. Montero, M. Carmen Gómez-Guillén. Compositional properties and bioactive potential of waste material from shrimp cooking juice. LWT. 2013; 54 (1):87-94.
Chicago/Turabian StyleEfrén Pérez Santín; M.M. Calvo; M.E. López-Caballero; P. Montero; M. Carmen Gómez-Guillén. 2013. "Compositional properties and bioactive potential of waste material from shrimp cooking juice." LWT 54, no. 1: 87-94.
The aim of this study was to determine the enzymatic activity and survival of three probiotic strains (Lactobacillus paracasei LAFTI-L26, Lactobacillus acidophilus LAFTI-L10 and Bifidobacterium animalis ssp. lactis LAFTI-B94) during incubation in six different varieties of green tea extracts. The polyphenol content, antioxidant, antimicrobial and antihypertensive properties in green tea (variety Wu Lu Mountain) and in two standards (epigallocatechin-3-gallate and rutin) were also investigated before and after incubation with B. animalis B94. The green tea extracts permitted the survival of the selected probiotic strains better than the saline solution, with B. animalis B94 maintaining the highest levels of viable cells. These selected probiotic bacteria exhibited β-glucosidase, β-galactosidase and α-rhamnosidase activity. The antioxidant and antihypertensive properties of standard solutions of epigallocatechin-3-gallate and rutin increased after incubation with B. animalis B94, caused by polyphenol content reduction and the formation of other more highly biologically active metabolites. However, during the incubation of green tea with B. animalis B94, changes in the concentration of the most abundant green tea polyphenols did not enhance the biological activity.
Antonio López De Lacey; Efrén Pérez Santín; M. E. López Caballero; P. Montero. Survival and metabolic activity of probiotic bacteria in green tea. LWT 2013, 55, 314 -322.
AMA StyleAntonio López De Lacey, Efrén Pérez Santín, M. E. López Caballero, P. Montero. Survival and metabolic activity of probiotic bacteria in green tea. LWT. 2013; 55 (1):314-322.
Chicago/Turabian StyleAntonio López De Lacey; Efrén Pérez Santín; M. E. López Caballero; P. Montero. 2013. "Survival and metabolic activity of probiotic bacteria in green tea." LWT 55, no. 1: 314-322.
Active biodegradable films based on agar and agar-fish gelatin were developed by the incorporation of green tea aqueous extract to the film forming solution. The effect of the partial replacement of agar by fish skin gelatin as well as the addition of the green tea extract on the physical properties of the resultant films was evaluated. Special attention was given to the release of antioxidant and antimicrobial compounds from the agar film matrices with and without gelatin. Agar-gelatin films were less resistant and more deformable than agar films. The inclusion of green tea extract decreased tensile strength and elongation at break in both agar and agar-gelatin films. Water vapour permeability and water resistance was not affected either by the replacement of agar by gelatin or the addition of green tea extract, but the water solubility noticeably increased in the films containing green tea extract. The presence of gelatin in the agar-green tea matrix film hindered the release of total phenolic compounds, catechins and flavonols in water. As a consequence, the antioxidant power released by the films was lower in the case of films containing gelatin. However, the antimicrobial activity of the films was not affected by the presence of gelatin. © 2012 Elsevier Ltd.Peer Reviewe
B. Giménez; A. López de Lacey; Efrén Pérez Santín; M.E. López-Caballero; P. Montero. Release of active compounds from agar and agar–gelatin films with green tea extract. Food Hydrocolloids 2013, 30, 264 -271.
AMA StyleB. Giménez, A. López de Lacey, Efrén Pérez Santín, M.E. López-Caballero, P. Montero. Release of active compounds from agar and agar–gelatin films with green tea extract. Food Hydrocolloids. 2013; 30 (1):264-271.
Chicago/Turabian StyleB. Giménez; A. López de Lacey; Efrén Pérez Santín; M.E. López-Caballero; P. Montero. 2013. "Release of active compounds from agar and agar–gelatin films with green tea extract." Food Hydrocolloids 30, no. 1: 264-271.
Simple edible films can be manufactured to meet not only their primary protective purpose but can be easily manipulated to meet sensory expectations and to contain compounds which enhance the protective properties or even have the potential to deliver health benefits. However, the use of such edible films not only to protect the food but as a vehicle to deliver health benefits has not been investigated. In this paper we study agar films containing an aqueous extract of green tea, rich in polyphenol compounds, and the bioaccessibility of these compounds during simulated digestion in the upper gastro-intestinal tract using a dynamic gastric model (DGM) and a static duodenal model. It is concluded that the recovery of the tea compounds added to the agar film mainly occurs in the stomach (50–80%) and that little or no additional recovery is observed in the duodenum. Furthermore, the green tea compounds recovered show both reducing power and radical scavenging ability, but not antimicrobial activity. The bioaccessibility of the green tea flavonols is reduced in the presence of gelatin used to simulate the presence of protein in the stomach, but it is not clear if this is due to reduced release or sequestration of released compounds by the gelatin.
A.M. López de Lacey; B. Giménez; Efrén Pérez Santín; R. Faulks; G. Mandalari; M.E. López-Caballero; P. Montero. Bioaccessibility of green tea polyphenols incorporated into an edible agar film during simulated human digestion. Food Research International 2012, 48, 462 -469.
AMA StyleA.M. López de Lacey, B. Giménez, Efrén Pérez Santín, R. Faulks, G. Mandalari, M.E. López-Caballero, P. Montero. Bioaccessibility of green tea polyphenols incorporated into an edible agar film during simulated human digestion. Food Research International. 2012; 48 (2):462-469.
Chicago/Turabian StyleA.M. López de Lacey; B. Giménez; Efrén Pérez Santín; R. Faulks; G. Mandalari; M.E. López-Caballero; P. Montero. 2012. "Bioaccessibility of green tea polyphenols incorporated into an edible agar film during simulated human digestion." Food Research International 48, no. 2: 462-469.
Gelatin obtained from giant squid (Dosidicus gigas) inner and outer tunics was hydrolyzed by seven commercial proteases (Protamex, Trypsin, Neutrase, Savinase, NS37005, Esperase and Alcalase) to produce bioactive hydrolysates. The Alcalase hydrolysate was the most potent angiotensin-converting enzyme (ACE) inhibitor (IC50=0.34mg/mL) while the Esperase hydrolysate showed the highest cytotoxic effect on cancer cells, with IC50 values of 0.13 and 0.10mg/mL for MCF-7 (human breast carcinoma) and U87 (glioma) cell lines, respectively. The radical scavenging capacity of gelatin increased approximately 3-fold for Protamex, Neutrase and NS37005 hydrolysates and between 7 and 10-fold for Trypsin, Savinase, Esperase and Alcalase hydrolysates. Trypsin, Savinase, Esperase and Alcalase hydrolysates had a metal chelating capacity above 80% whereas Protamex, Neutrase and NS37005 hydrolysates registered less than 25%. The antioxidant activity measured by FRAP (ferric ion reducing power) was largely unaffected by the enzyme used, increasing approximately 2-fold for all hydrolysates. The most active hydrolysates (Alcalase and Esperase) were comprised mostly of peptides with molecular weights ranging from 500 to 1400Da, however, a clear relationship between bioactive properties and molecular weight distribution of all the hydrolysates was not fully established. © 2011 Elsevier Ltd.Peer Reviewe
Ailen Aleman; Efrén Pérez Santín; Stéphanie Bordenave; Ingrid Arnaudin; M. Carmen Gómez-Guillén; P. Montero. Squid gelatin hydrolysates with antihypertensive, anticancer and antioxidant activity. Food Research International 2011, 44, 1044 -1051.
AMA StyleAilen Aleman, Efrén Pérez Santín, Stéphanie Bordenave, Ingrid Arnaudin, M. Carmen Gómez-Guillén, P. Montero. Squid gelatin hydrolysates with antihypertensive, anticancer and antioxidant activity. Food Research International. 2011; 44 (4):1044-1051.
Chicago/Turabian StyleAilen Aleman; Efrén Pérez Santín; Stéphanie Bordenave; Ingrid Arnaudin; M. Carmen Gómez-Guillén; P. Montero. 2011. "Squid gelatin hydrolysates with antihypertensive, anticancer and antioxidant activity." Food Research International 44, no. 4: 1044-1051.
Squid gelatin obtained from inner and outer tunics was hydrolysed with Alcalase to isolate antioxidant peptide sequences. The ACE-inhibitory activity of the isolated peptides was also evaluated. After fractionation by ultrafiltration and size-exclusion chromatography into four fractions, the antioxidant activity of the peptide fractions was determined by radical scavenging ability and ferric reducing power. Fraction FIII showed the highest antioxidant activity, although slight differences could be expected in the antioxidant activity of the different fractions based on the amino acid composition. FIII was subjected to liquid chromatography and tandem mass spectrometry (LC–MS/MS) and two major compounds were identified: the compound with m/z 952.42, which could be mostly comprised by the carbohydrate fucose, and the peptide with m/z 1410.63. Three possible sequences were proposed and synthesised for this peptide, and the contribution of Leu or Hyp residues to the antioxidant and ACE-inhibitory activities of the resulting sequence was evaluated. The presence of Leu residues in the peptide sequence in replacement of Hyp seems to play an important role in the antioxidant and ACE-inhibitory activity.
Ailen Aleman; B. Giménez; Efrén Pérez Santín; M. Carmen Gómez-Guillén; P. Montero. Contribution of Leu and Hyp residues to antioxidant and ACE-inhibitory activities of peptide sequences isolated from squid gelatin hydrolysate. Food Chemistry 2011, 125, 334 -341.
AMA StyleAilen Aleman, B. Giménez, Efrén Pérez Santín, M. Carmen Gómez-Guillén, P. Montero. Contribution of Leu and Hyp residues to antioxidant and ACE-inhibitory activities of peptide sequences isolated from squid gelatin hydrolysate. Food Chemistry. 2011; 125 (2):334-341.
Chicago/Turabian StyleAilen Aleman; B. Giménez; Efrén Pérez Santín; M. Carmen Gómez-Guillén; P. Montero. 2011. "Contribution of Leu and Hyp residues to antioxidant and ACE-inhibitory activities of peptide sequences isolated from squid gelatin hydrolysate." Food Chemistry 125, no. 2: 334-341.
Rexinoids are ligands for the retinoid X receptor (RXR) that have great promise for both the prevention and treatment of cancer and metabolic diseases. In this regard, synthetic, functional, and structural investigations into the structure-activity relationships of derivatives of the potent RXR agonist (E)-3-[3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-4-hydroxyphenyl]acrylic acid (CD3254, 9) have been conducted. We recently reported on the characterization of a series of C3'-substituted alkyl ether analogues of 9 (10a-f), which display activities ranging from partial agonists to pure antagonists. The importance of the position of the alkoxy side chain for ligand activity has been further explored with the synthesis of C4'-substituted analogues (11a-f). Here we describe the synthesis of compounds 11a-f, which appear functionally different from their isomeric counterparts, as judged from transactivation assays and fluorescence anisotropy experiments. We also report on the 2.0 A resolution structure of RXR in complex with the parent compound 9, which helps understanding of the impact of the alkyl side chain location on ligand activity.
Efrén Pérez Santín; Pierre Germain; Fabien Quillard; Harshal Khanwalkar; Fátima Rodríguez-Barrios; Hinrich Gronemeyer; Angel Rodriguez de Lera; William Bourguet. Modulating Retinoid X Receptor with a Series of (E)-3-[4-Hydroxy-3-(3-alkoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)phenyl]acrylic Acids and Their 4-Alkoxy Isomers†. Journal of Medicinal Chemistry 2009, 52, 3150 -3158.
AMA StyleEfrén Pérez Santín, Pierre Germain, Fabien Quillard, Harshal Khanwalkar, Fátima Rodríguez-Barrios, Hinrich Gronemeyer, Angel Rodriguez de Lera, William Bourguet. Modulating Retinoid X Receptor with a Series of (E)-3-[4-Hydroxy-3-(3-alkoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)phenyl]acrylic Acids and Their 4-Alkoxy Isomers†. Journal of Medicinal Chemistry. 2009; 52 (10):3150-3158.
Chicago/Turabian StyleEfrén Pérez Santín; Pierre Germain; Fabien Quillard; Harshal Khanwalkar; Fátima Rodríguez-Barrios; Hinrich Gronemeyer; Angel Rodriguez de Lera; William Bourguet. 2009. "Modulating Retinoid X Receptor with a Series of (E)-3-[4-Hydroxy-3-(3-alkoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)phenyl]acrylic Acids and Their 4-Alkoxy Isomers†." Journal of Medicinal Chemistry 52, no. 10: 3150-3158.
International audienceA collection of arotinoids with a central benzofuran or naphthofuran ring structure was efficiently synthesized by a three-step process that comprises a Sonogashira coupling, an iodine-induced 5-endo-dig cyclization of the o-methoxyphenyl- or naphthyl-ethynyl benzoates, and finally a Suzuki/Sonogashira coupling of the corresponding 3-iodobenzo- or naphthofurans. Most of these 3-substituted naphthofuran arotinoids (but not the 5,7-di-tert-butylbenzofurans with the same substitution pattern at the C2 and C3 positions) are potent agonists of the retinoic acid receptor (RAR) subtypes, with activities in the nanomolar range
Efrén Pérez Santín; Harshal Khanwalkar; Johannes Voegel; Pascal Collette; Pascale Mauvais; Hinrich Gronemeyer; Angel Rodriguez De Lera. Highly Potent Naphthofuran-Based Retinoic Acid Receptor Agonists. ChemMedChem 2009, 4, 780 -791.
AMA StyleEfrén Pérez Santín, Harshal Khanwalkar, Johannes Voegel, Pascal Collette, Pascale Mauvais, Hinrich Gronemeyer, Angel Rodriguez De Lera. Highly Potent Naphthofuran-Based Retinoic Acid Receptor Agonists. ChemMedChem. 2009; 4 (5):780-791.
Chicago/Turabian StyleEfrén Pérez Santín; Harshal Khanwalkar; Johannes Voegel; Pascal Collette; Pascale Mauvais; Hinrich Gronemeyer; Angel Rodriguez De Lera. 2009. "Highly Potent Naphthofuran-Based Retinoic Acid Receptor Agonists." ChemMedChem 4, no. 5: 780-791.
A series of analogues of the PPARγ ligand 15-deoxy-Δ12,14-PGJ2 have been synthesized by functionalization of a 5-alkyl-4-hydroxycyclopentenone core structure obtained by Piancatelli rearrangement of precursor furylcarbinol. Transient transactivation assays indicate that analogues 18 and 20 are selective nanomolar agonists of PPARγ. This subtype selectivity is lost in derivatives (23, 24) with an alkynyl (oct-1-yn) chain at the C3 position, although the cyclopentenone derivative with cis relative configuration (23) showed greater affinity for PPARα.
M. Paz Otero; Efrén Pérez Santín; Fátima Rodríguez-Barrios; Belén Vaz; Ángel R. de Lera. Selective, potent PPARγ agonists with cyclopentenone core structure. Bioorganic & Medicinal Chemistry Letters 2009, 19, 1883 -1886.
AMA StyleM. Paz Otero, Efrén Pérez Santín, Fátima Rodríguez-Barrios, Belén Vaz, Ángel R. de Lera. Selective, potent PPARγ agonists with cyclopentenone core structure. Bioorganic & Medicinal Chemistry Letters. 2009; 19 (7):1883-1886.
Chicago/Turabian StyleM. Paz Otero; Efrén Pérez Santín; Fátima Rodríguez-Barrios; Belén Vaz; Ángel R. de Lera. 2009. "Selective, potent PPARγ agonists with cyclopentenone core structure." Bioorganic & Medicinal Chemistry Letters 19, no. 7: 1883-1886.