108 results on '"Joaquín Altarejos"'
Search Results
2. Chemical Characterization of Pruning Wood Extracts from Six Japanese Plum (Prunus salicina Lindl.) Cultivars and Their Antitumor Activity
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Juan Ortega-Vidal, Nuria Mut-Salud, José M. de la Torre, Joaquín Altarejos, and Sofía Salido
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Prunus salicina (Rosaceae) ,pruning woods ,agricultural wastes ,phenolics ,proanthocyanidins ,HPLC quantification ,Organic chemistry ,QD241-441 - Abstract
The Japanese plum tree (Prunus salicina Lindl.) is mainly cultivated in temperate areas of China and some European countries. Certain amounts of wood (from pruning works) are generated every year from this crop of worldwide commercial significance. The main objective of this work was to value this agricultural woody residue, for which the chemical composition of pruning wood extracts from six Japanese plum cultivars was investigated, and the antiproliferative activity of extracts and pure phenolics present in those extracts was measured. For the chemical characterization, total phenolic content and DPPH radical-scavenging assays and HPLC‒DAD/ESI‒MS analyses were performed, with the procyanidin (−)-ent-epicatechin-(2α→O→7,4α→8)-epicatechin (5) and the propelargonidin (+)-epiafzelechin-(2β→O→7,4β→8)-epicatechin (7) being the major components of the wood extracts. Some quantitative differences were found among plum cultivars, and the content of proanthocyanidins ranged from 1.50 (cv. ‘Fortune’) to 4.44 (cv. ‘Showtime’) mg/g of dry wood. Regarding the antitumoral activity, eight wood extracts and four phenolic compounds were evaluated in MCF-7 cells after 48 h of induction, showing the wood extract from cv. ‘Songold’ and (‒)-annphenone (3), the best antiproliferative activity (IC50: 424 μg/mL and 405 μg/mL, respectively).
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- 2024
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3. Halogenated Analogs to Natural A-Type Proanthocyanidins: Evaluation of Their Antioxidant and Antimicrobial Properties and Possible Application in Food Industries
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Antonio Cobo, Alfonso Alejo-Armijo, Daniel Cruz, Joaquín Altarejos, Sofía Salido, and Elena Ortega-Morente
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A-type proanthocyanidin analogs ,flavylium chemistry ,antimicrobial activity ,antibiofilm activity ,antioxidant activity ,Organic chemistry ,QD241-441 - Abstract
A description of new antimicrobial agents suitable for food industries has become necessary, and natural compounds are being considered as promising sources of new active derivatives to be used with the aim of improving food safety. We have previously described desirable antimicrobial and antibiofilm activities against foodborne bacteria by analogs to A-type proanthocyanidins (PACs) with a nitro (NO2) group at carbon 6 of the A-ring. We report herein the synthesis of eight additional analogs with chloro and bromo atoms at the A-ring and the systematic study of their antimicrobial and antioxidant activities in order to evaluate their possible application as biocides or food preservatives, as well as to elucidate new structure–activity relationships. The results from this study show that halogenated analogs to natural A-type proanthocyanidins rise above the nitro derivatives previously reported in their antimicrobial activities. Gram-positive bacteria are the most sensitive to all the analogs and combinations assayed, showing MICs from 10 to 50 μg/mL in most cases, as well as reductions in biofilm formation and the disruption of preformed biofilms of at least 75%. Some structure–activity relationships previously described have also been corroborated. Analogs with just one OH group at the B-ring show better antimicrobial activities than those with two OH groups, and those analogs with two or three OH groups in the whole structure are more active than those with four OH groups. In addition, the analogs with two OH groups at the B-ring and chloro at the A-ring are the most effective when antibiofilm activities are studied, especially at low concentrations.
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- 2024
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4. Biological effects of olive oil phenolic compounds on mitochondria
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Mercedes Blanco-Benítez, Ana Calderón-Fernández, Saray Canales-Cortés, Eva Alegre-Cortés, Elisabet Uribe-Carretero, Marta Paredes-Barquero, Alberto Gimenez-Bejarano, Gema Duque González, Patricia Gómez-Suaga, Juan Ortega-Vidal, Sofía Salido, Joaquín Altarejos, Guadalupe Martínez-Chacón, Mireia Niso-Santano, José M. Fuentes, Rosa A. González-Polo, and Sokhna M. S. Yakhine-Diop
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antioxidants ,cell death ,hydroxytyrosol ,mediterranean diet ,mitophagy ,oleuropein ,Neoplasms. Tumors. Oncology. Including cancer and carcinogens ,RC254-282 - Abstract
Phenolic compounds derived from olive oil have beneficial health properties against cancer, neurodegenerative, and metabolic diseases. Therefore, there are discrepancies in their impact on mitochondrial function that result in changes in oxidative capacity, mitochondrial respiration, and energetic demands. This review focuses on the versatile role of oleuropein, a potent antioxidant that regulates the AMPK/SIRT1/mTOR pathway to modulate autophagy/mitophagy and maintain metabolic homeostasis.
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- 2022
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5. Synthesis of Analogs to A-Type Proanthocyanidin Natural Products with Enhanced Antimicrobial Properties against Foodborne Microorganisms
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Antonio Cobo, Alfonso Alejo-Armijo, Daniel Cruz, Joaquín Altarejos, Sofía Salido, and Elena Ortega-Morente
- Subjects
A-type proanthocyanidin analogs ,flavylium chemistry ,antimicrobial activity ,antibiofilm activity ,antioxidant activity ,Organic chemistry ,QD241-441 - Abstract
Developing new types of effective antimicrobial compounds derived from natural products is of interest for the food industry. Some analogs to A-type proanthocyanidins have shown promising antimicrobial and antibiofilm activities against foodborne bacteria. We report herein the synthesis of seven additional analogs with NO2 group at A-ring and their abilities for inhibiting the growth and the biofilm formation by twenty-one foodborne bacteria. Among them, analog 4 (one OH at B-ring; two OHs at D-ring) showed the highest antimicrobial activity. The best results with these new analogs were obtained in terms of their antibiofilm activities: analog 1 (two OHs at B-ring; one OH at D-ring) inhibited at least 75% of biofilm formation by six strains at all of the concentrations tested, analog 2 (two OHs at B-ring; two OHs at D-ring; one CH3 at C-ring) also showed antibiofilm activity on thirteen of the bacteria tested, and analog 5 (one OH at B-ring; one OH at D-ring) was able to disrupt preformed biofilms in eleven strains. The description of new and more active analogs of natural compounds and the elucidation of their structure-activity relationships may contribute to the active development of new food packaging for preventing biofilm formation and lengthening the food shelf life.
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- 2023
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6. Gene flow between diploid and tetraploid junipers - two contrasting evolutionary pathways in two Juniperus populations
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Perla Farhat, Sonja Siljak-Yakovlev, Nicolas Valentin, Carlos Fabregat, Silvia Lopez-Udias, Carlos Salazar-Mendias, Joaquín Altarejos, and Robert P. Adams
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Juniperus ,Gene flow ,Polyploidy ,Triploid bridge ,Hybridization ,Introgression ,Evolution ,QH359-425 - Abstract
Abstract Background Gene flow and polyploidy have been found to be important in Juniperus evolution. However, little evidence has been published elucidating the association of both phenomena in juniper taxa in the wild. Two main areas were studied in Spain (Eastern Iberian Range and Sierra de Baza) with both diploid and tetraploid taxa present in sympatry. Gene flow and ploidy level were assessed for these taxa and the resulted offspring. Results Twenty-two allo-triploid hybrids between J. sabina var. sabina and J. thurifera were found in the Eastern Iberian Range population. However, in the Sierra de Baza population no triploids were found. Instead, 18 allo-tetraploid hybrids between two tetraploid taxa: J. sabina var. balkanensis and J. thurifera were discovered. High genetic diversity was exhibited among the tetraploid hybrids at Sierra de Baza, in contrast to the genetically identical triploid hybrids at the Eastern Iberian Range; this suggests meiotic difficulties within the triploid hybrids. In addition, unidirectional gene flow was observed in both studied areas. Conclusion Polyploidy and hybridization can be complementary partners in the evolution of Juniperus taxa in sympatric occurrences. Juniperus was shown to be an ideal coniferous model to study these two phenomena, independently or in concert.
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- 2020
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7. Effects of Oleacein, a New Epinutraceutical Bioproduct from Extra Virgin Olive Oil, in LPS-Activated Murine Immune Cells
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Rocío Muñoz-García, Marina Sánchez-Hidalgo, Tatiana Montoya, Manuel Alcarranza, Juan Ortega-Vidal, Joaquín Altarejos, and Catalina Alarcón-de-la-Lastra
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epigenetic ,histone ,inflammation ,immunity ,macrophages ,oleacein ,Medicine ,Pharmacy and materia medica ,RS1-441 - Abstract
The present study was designed to evaluate the immunomodulatory effects of the secoiridoid from extra virgin olive oil, oleacein (OLA), deepening into the possible signaling pathways involved in LPS-activated murine peritoneal macrophages. Moreover, we have explored OLA-induced epigenetic changes in histone markers and related cytokine production in murine LPS-stimulated murine splenocytes. Murine cells were treated with OLA in the presence or absence of LPS (5 μg/mL) for 18 or 24 h. OLA modulated the oxidative stress and the inflammatory response produced by LPS stimulation in murine peritoneal macrophages, by the inhibition of pro-inflammatory cytokines (TNF-α, IL-6, IL-1β, IFN-γ, IL-17 and IL-18) and ROS production and the expression of pro-inflammatory enzymes such as iNOS, COX-2 and m-PGES1. These protective effects could be due to the activation of the Nrf-2/HO-1 axis and the inhibition of JAK/STAT, ERK and P38 MAPKs and inflammasome canonical and non-canonical signaling pathways. Moreover, OLA modulated epigenetic modifications throughout histone methylation deacetylation (H3K18ac) and (H3K9me3 and H3K27me) in LPS-activated spleen cells. In conclusion, our data present OLA as an interesting anti-inflammatory and antioxidant natural compound that is able to regulate histone epigenetic markers. Nevertheless, additional in vivo studies are required to further investigate the beneficial effects of this EVOO secoiridoid, which might be a promising epinutraceutical bioproduct for the management of immune-related inflammatory diseases.
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- 2022
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8. (−)-Methyl-Oleocanthal, a New Oleocanthal Metabolite Reduces LPS-Induced Inflammatory and Oxidative Response: Molecular Signaling Pathways and Histones Epigenetic Modulation
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Tatiana Montoya, Catalina Alarcón-de-la-Lastra, María Luisa Castejón, Juan Ortega-Vidal, Joaquín Altarejos, and Marina Sánchez-Hidalgo
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antioxidant ,histones ,inflammation ,macrophages ,metabolite ,methylation ,Therapeutics. Pharmacology ,RM1-950 - Abstract
The antioxidant and anti-inflammatory responses of (−)-methyl-oleocanthal (met-OLE), a new metabolite of the extra virgin olive oil (EVOO) phenolic oleocanthal (OLE), were explored in lipopolysaccharide (LPS)-induced murine peritoneal macrophages. Possible signaling pathways and epigenetic modulation of histones were studied. Met-OLE inhibited LPS-induced intracellular reactive oxygen species (ROS) and nitrite (NO) production and decreased the overexpression of the pro-inflammatory enzymes COX-2, mPGES-1 and iNOS in murine macrophages. In addition, met-OLE was able to significantly decrease the activation of p38, JNK, and ERK mitogen-activated protein kinases (MAPKs) and blocked canonical and non-canonical inflammasome signaling pathways. On the contrary, met-OLE upregulated haem oxigenase 1 (HO-1) and nuclear factor (erythroid-derived 2)-like 2 (Nrf-2) expression in treated cells. Finally, met-OLE pretreated spleen cells counteracted LPS induction, preventing H3K18 acetylation or H3K9 and H3K27 demethylation. Overall, these results provide novel mechanistic insights into the beneficial effects of met-OLE regarding the regulation of the immune–inflammatory response through epigenetic changes in histone markers. This revealing evidence suggests that the methylated metabolite of OLE may contribute significantly to the beneficial effects that are associated with the secoiridoid-related compound and the usual consumption of EVOO.
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- 2021
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9. Synthesis and Olfactory Evaluation of Bulky Moiety-Modified Analogues to the Sandalwood Odorant Polysantol®
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Adolfo Sánchez, Manuel Nogueras, Sofía Salido, Concepción Badía, Joaquín Altarejos, Pablo J. Linares-Palomino, and Laura Chapado
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sandalwood odorants ,Polysantol® analogues ,nopol derivative ,odour evaluation ,Organic chemistry ,QD241-441 - Abstract
Five new bulky moiety-modified analogues of the sandalwood odorant Polysantol® have been synthesized by aldol condensation of appropriate aldehydes with butanone, deconjugative α-methylation of the resulting α,β-unsaturated ketones, and reduction of the corresponding β,γ-unsaturated ketones. The final compounds were evaluated organoleptically and one of them seemed to be of special interest for its natural sandalwood scent.
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- 2009
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10. Effect of Extraction Conditions on the Antioxidant Activity of Olive Wood Extracts
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Mercedes Pérez-Bonilla, Sofía Salido, Adolfo Sánchez, Teris A. van Beek, and Joaquín Altarejos
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Nutrition. Foods and food supply ,TX341-641 ,Food processing and manufacture ,TP368-456 - Abstract
An investigation to optimize the extraction yield and the radical scavenging activity from the agricultural by-product olive tree wood (Olea europaea L., cultivar Picual) using six different extraction protocols was carried out. Four olive wood samples from different geographical origin, and harvesting time have been used for comparison purposes. Among the fifty olive wood extracts obtained in this study, the most active ones were those prepared with ethyl acetate, either through direct extraction or by successive liquid-liquid partitioning procedures, the main components being the secoiridoids oleuropein and ligustroside. An acid hydrolysis pretreatment of olive wood samples before extractions did not improve the results. In the course of this study, two compounds were isolated from the ethanolic extracts of olive wood collected during the olives’ harvesting season and identified as (7′′R)-7′′-ethoxyoleuropein (1) and (7′′S)-7′′-ethoxyoleuropein (2).
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- 2013
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11. 2-(1-Bromo-1-methyl-ethyl)-2-methyl-[1,3]dioxolane
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Adolfo Sánchez, Manuel Nogueras, Joaquín Altarejos, Sofía Salido, Pablo J. Linares-Palomino, and Juan M. Castro
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Bromination ,a-bromoketone ,dioxolane ring. ,Inorganic chemistry ,QD146-197 - Abstract
n/a
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- 2004
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12. (E)-6-(2,2,3-Trimethyl-cyclopent-3-enyl)-hex-4-en-3-one
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Manuel Nogueras, Joaquín Altarejos, Sofía Salido, Pablo J. Linares-Palomino, Juan M. Castro, Concepción Badía, and Adolfo Sánchez
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a-Campholenic aldehyde ,ethyl 2-methylacetoacetate ,aldol condensation. ,Inorganic chemistry ,QD146-197 - Abstract
n/a
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- 2004
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13. endo-N-(5,5-Dimethyl-6-methylene-bicyclo[2.2.1]hept-2-yl)-4-methyl-benzenesulfonamide
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Manuel Nogueras, Joaquín Altarejos, Sofía Salido, Pablo J. Linares-Palomino, Juan M. Castro, Concepción Badía, and Adolfo Sánchez
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a-Campholenic aldehyde ,acid-catalyzed rearrangement ,intramolecular cyclization. ,Inorganic chemistry ,QD146-197 - Abstract
n/a
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- 2004
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14. Synthesis of Analogs to A-Type Proanthocyanidin Natural Products with Enhanced Antimicrobial Properties against Foodborne Microorganisms
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Ortega-Morente, Antonio Cobo, Alfonso Alejo-Armijo, Daniel Cruz, Joaquín Altarejos, Sofía Salido, and Elena
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A-type proanthocyanidin analogs ,flavylium chemistry ,antimicrobial activity ,antibiofilm activity ,antioxidant activity - Abstract
Developing new types of effective antimicrobial compounds derived from natural products is of interest for the food industry. Some analogs to A-type proanthocyanidins have shown promising antimicrobial and antibiofilm activities against foodborne bacteria. We report herein the synthesis of seven additional analogs with NO2 group at A-ring and their abilities for inhibiting the growth and the biofilm formation by twenty-one foodborne bacteria. Among them, analog 4 (one OH at B-ring; two OHs at D-ring) showed the highest antimicrobial activity. The best results with these new analogs were obtained in terms of their antibiofilm activities: analog 1 (two OHs at B-ring; one OH at D-ring) inhibited at least 75% of biofilm formation by six strains at all of the concentrations tested, analog 2 (two OHs at B-ring; two OHs at D-ring; one CH3 at C-ring) also showed antibiofilm activity on thirteen of the bacteria tested, and analog 5 (one OH at B-ring; one OH at D-ring) was able to disrupt preformed biofilms in eleven strains. The description of new and more active analogs of natural compounds and the elucidation of their structure-activity relationships may contribute to the active development of new food packaging for preventing biofilm formation and lengthening the food shelf life.
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- 2023
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15. Proanthocyanidins in Pruning Wood Extracts of Four European Plum ( Prunus domestica L.) Cultivars and Their h LDHA Inhibitory Activity
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Juan Ortega‐Vidal, Lucía Ruiz‐Martos, Sofía Salido, and Joaquín Altarejos
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Molecular Medicine ,Bioengineering ,General Chemistry ,General Medicine ,Molecular Biology ,Biochemistry - Published
- 2023
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16. (−)-Oleocanthal induces death preferentially in tumor hematopoietic cells through caspase dependent and independent mechanisms
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Chiara Pastorio, Sara Torres-Rusillo, Juan Ortega-Vidal, M. Carmen Jiménez-López, Inmaculada Iañez, Sofía Salido, Manuel Santamaría, Joaquín Altarejos, and Ignacio J. Molina
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Annexins ,Caspase 3 ,Caspases ,Cell Line, Tumor ,Hematologic Neoplasms ,Humans ,Apoptosis ,General Medicine ,Reactive Oxygen Species ,Olive Oil ,Cyclopentane Monoterpenes ,Food Science - Abstract
Olive oil is a key component of the highly cardiovascular protective Mediterranean diet. (−)-Oleocanthal (OLC) is one of the most interesting phenolics present in virgin olive oil, and is formed from secoiridoid ligustroside during the processing of olives to yield the oil. Anti-inflammatory and anti-oxidant properties were identified shortly after OLC isolation, followed by the discovery of anti-tumor activities in a few nonhematopoietic cell lineages. Because of the scarcity of tissues potentially targeted by OLC analyzed so far and the unresolved mechanism(s) for OLC anti-tumor properties, we used a panel of 17 cell lines belonging to 11 tissue lineages to carry out a detailed examination of targets and pathways leading to cell growth inhibition and death. We found that OLC inhibits cell proliferation and induces apoptotic death as revealed by sub-G1 cell cycle analyses and Annexin-V staining in all lineages analyzed except lung carcinoma cell lines. Hematopoietic tumor cell lines, untested until now, were the most sensitive to OLC treatment, whereas non-transformed cells were significantly resistant to cell death. The specificity of OLC-mediated caspase activation was confirmed by blocking experiments and the use of transfectants overexpressing anti apoptotic genes. OLC triggers typical mediators of the intrinsic apoptotic pathway such as production of reactive oxygen species and mitochondrial membrane depolarization (Δψm). Complete blockade of caspases, however, did not result in parallel abrogation of Annexin-V staining, thus suggesting that complex mechanisms are involved in triggering OLC-mediated cell death. Our results demonstrate that OLC preferentially targets hematopoietic tumor cell lines and support that cell death is mediated by caspase-dependent and independent mechanisms., Universidad de Granada-Junta de Andalucia A-CTS-480-UGR18 B.CTS.690.UGR20, Action for AT, United Kingdom charity AAT-8GRA02
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- 2022
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17. Ligstroside aglycon, an extra virgin olive oil secoiridoid, prevents inflammation by regulation of MAPKs, JAK/STAT, NF-κB, Nrf2/HO-1, and NLRP3 inflammasome signaling pathways in LPS-stimulated murine peritoneal macrophages
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María Luisa Castejón, Tatiana Montoya, Juan Ortega-Vidal, Joaquín Altarejos, and Catalina Alarcón-de-la-Lastra
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Lipopolysaccharides ,Inflammasomes ,NF-E2-Related Factor 2 ,Anti-Inflammatory Agents ,Nitric Oxide Synthase Type II ,Nitric Oxide ,Antioxidants ,Mice ,Glucosides ,NLR Family, Pyrin Domain-Containing 3 Protein ,Animals ,Iridoids ,Olive Oil ,Janus Kinases ,Prostaglandin-E Synthases ,Pyrans ,Inflammation ,Nucleotides ,NF-kappa B ,NADPH Oxidases ,General Medicine ,Cyclooxygenase 2 ,Macrophages, Peritoneal ,Cytokines ,Mitogen-Activated Protein Kinases ,Heme Oxygenase-1 ,Signal Transduction ,Food Science - Abstract
Ligstroside aglycon (LA) is one of the main polyphenols in extra virgin olive oil (EVOO); nevertheless, it is scarcely investigated. The aim of this study was to evaluate the immunomodulatory and anti-inflammatory effects of LA on lipopolysaccharide (LPS)-stimulated murine peritoneal macrophages, as well as the potential signaling pathways involved. Isolated macrophages were treated with LA (50, 25, and 12.5 μM) in the presence or absence of LPS (5 μg ml
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- 2022
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18. Antimicrobial and antioxidant activities of flavonoids isolated from wood of sweet cherry tree (Prunus avium L.)
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Antonio Cobo, Antonio Gálvez, Sofía Salido, Juan Ortega-Vidal, Elena Ortega-Morente, Joaquín Altarejos, and Alfonso Alejo-Armijo
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0106 biological sciences ,Chemistry ,General Chemical Engineering ,02 engineering and technology ,General Chemistry ,021001 nanoscience & nanotechnology ,Antimicrobial ,01 natural sciences ,metropolitan_transit.transit_stop ,Prunus ,Horticulture ,Tree (data structure) ,010608 biotechnology ,Temperate climate ,General Materials Science ,metropolitan_transit ,0210 nano-technology ,Pruning ,Cherry tree - Abstract
Sweet cherry (Prunus avium L.) is a tree widely cultivated in temperate regions for its tasty and healing fruits. Pruning works on the tree give each year considerable amounts of woody wastes that hardly have any utility. The aims of this work were to detect the most active antioxidants present in a cherry pruning wood sample, to isolate and characterize them, and study the antimicrobial and antibiofilm activities of components found in the wood ethyl acetate extract against a selection of foodborne microorganisms. The online HPLC–DPPH technique allowed the detection of two active antioxidant peaks that, after being isolated by a combination of countercurrent chromatography (FCPC) and conventional preparative techniques, and subsequent structural characterization by NMR, MS and polarimetry, resulted to be (‒)-catechin (1) and (‒)-taxifolin (4). Other components of the cherry wood extract were also isolated, among which compounds 1, 4, and (+)-dihydrowogonin (12) have never been reported in P. avium. A selection of the isolated flavonoids was submitted to antimicrobial and antibiofilm activity evaluations against strains from type culture collections, as well as on multi-resistant strains previously isolated in our laboratory. Those compounds with antimicrobial activity detected in preliminary screenings by standard agar diffusion tests ‒the flavan-3-ol 1, the flavanonols 4 and (+)-aromadendrin (5), the flavanone (+)-pinocembrin (15), and the flavone tectochrysin (17)‒ were subjected to the minimal inhibitory concentration (MIC) test, showing all of them MIC values of 100 μg/mL. Compound 4 also induced a significative inhibition on the formation of biofilms by Enterobacter sp. UJA37p at a concentration of 1 μg/mL and a significative disruption of preformed biofilm by this strain at 0.1 µg/mL. Similar results on biofilm disruption were observed with compound 17.
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- 2021
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19. Recovery and Seasonal Variation of Cinnamtannin B‐1 from Laurel ( Laurus nobilis L.) Pruning Wood Wastes
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Joaquín Altarejos, Juan Ortega-Vidal, Sofia Salido, and Alfonso Alejo Armijo
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Molecular Medicine ,Proanthocyanidins ,Bioengineering ,Seasons ,General Chemistry ,General Medicine ,Laurus ,Wood ,Molecular Biology ,Biochemistry ,Catechin - Abstract
Cinnamtannin B-1 (C-B1) is a commercially-available trimeric A-type procyanidin with remarkable cellular actions mainly derived from its high radical scavenging activity. C-B1 is the main phenolic compound of laurel wood, which has previously been isolated by a combination of conventional chromatographic techniques. The first aim of this work was to find laurel trees containing as much C-B1 as possible, and learn about the influence of variables, such as gender and harvest time, on the production of C-B1 by the tree. It was found that all studied trees tend to give higher C-B1 percentages in the May-July period, from 6 % to 18 %, and lower ones around March (spring) and November (fall), from 1 % to 8 %. In a general way, it also seems that the female trees tend to produce a bit more C-B1 (from 2.8 % to 17.3 %) than male ones (from 1.7 % to 13.4 %). In addition, eight minor phenolic compounds [(-)-ent-catechin (1), (-)-ent-epicatechin-(4α→8)-ent-epicatechin (2), (epi)catechin-(4→8)-(epi)afzelechin-(4→8)-(epi)catechin (3), (+)-epiafzelechin-(4β→8)-epicatechin (4), (-)-epicatechin (5), (-)-afzelechin-(4α→8)-epicatechin (6), (epi)afzelechin-(4→8)-(epi)afzelechin-(4→8)-(epi)catechin (7) and (+)-epicatechin-(4β→8,2β→O-7)-epicatechin-(4β→8)-catechin (C-D1)] were found and quantified in the ethyl acetate extract of the wood samples. The second aim of this work was to improve the recovery of C-B1 from laurel wood. The use of the fast centrifugal partition chromatography (FCPC) technique has allowed for a recovery of 96 % of a technical-grade C-B1 (64 % in a previous protocol using conventional column chromatography on silica gel and size-exclusion chromatography).
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- 2022
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20. (-)-Methyl-Oleocanthal, a New Oleocanthal Metabolite Reduces LPS-Induced Inflammatory and Oxidative Response: Molecular Signaling Pathways and Histones Epigenetic Modulation
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Tatiana Montoya, Catalina Alarcón-de-la-Lastra, María Luisa Castejón, Juan Ortega-Vidal, Joaquín Altarejos, Marina Sánchez-Hidalgo, Universidad de Sevilla. Departamento de Farmacología, Ministerio de Economía y Competitividad (MINECO). España, and Junta de Andalucía
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antioxidant ,Physiology ,Clinical Biochemistry ,metabolite ,Cell Biology ,RM1-950 ,olive oil ,Biochemistry ,Article ,oleocanthal ,macrophages ,inflammation ,histones ,methylation ,Therapeutics. Pharmacology ,Molecular Biology - Abstract
The antioxidant and anti-inflammatory responses of (−)-methyl-oleocanthal (met-OLE), a new metabolite of the extra virgin olive oil (EVOO) phenolic oleocanthal (OLE), were explored in lipopolysaccharide (LPS)-induced murine peritoneal macrophages. Possible signaling pathways and epigenetic modulation of histones were studied. Met-OLE inhibited LPS-induced intracellular reactive oxygen species (ROS) and nitrite (NO) production and decreased the overexpression of the pro-inflammatory enzymes COX-2, mPGES-1 and iNOS in murine macrophages. In addition, met-OLE was able to significantly decrease the activation of p38, JNK, and ERK mitogen-activated protein kinases (MAPKs) and blocked canonical and non-canonical inflammasome signaling pathways. On the contrary, met-OLE upregulated haem oxigenase 1 (HO-1) and nuclear factor (erythroid-derived 2)-like 2 (Nrf-2) expression in treated cells. Finally, met-OLE pretreated spleen cells counteracted LPS induction, preventing H3K18 acetylation or H3K9 and H3K27 demethylation. Overall, these results provide novel mechanistic insights into the beneficial effects of met-OLE regarding the regulation of the immune–inflammatory response through epigenetic changes in histone markers. This revealing evidence suggests that the methylated metabolite of OLE may contribute significantly to the beneficial effects that are associated with the secoiridoid-related compound and the usual consumption of EVOO. España Ministerio de Economía y Competitividad grant number AG-2017-89342-P Junta de Andalucía funded by CTS-259, FQM-182
- Published
- 2021
21. (−)‑Oleocanthal inhibits proliferation and migration by modulating Ca2+ entry through TRPC6 in breast cancer cells
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Ginés M. Salido, Juan Ortega-Vidal, Joaquín Altarejos, M. El Haouari, Jose J. Lopez, Raquel Diez-Bello, Isaac Jardin, Sofía Salido, and Juan A. Rosado
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0301 basic medicine ,Cell growth ,Chemistry ,Cancer ,Cell Biology ,medicine.disease ,03 medical and health sciences ,030104 developmental biology ,0302 clinical medicine ,Downregulation and upregulation ,030220 oncology & carcinogenesis ,Cancer research ,medicine ,Gene silencing ,Cytotoxic T cell ,Hormonal therapy ,Viability assay ,skin and connective tissue diseases ,Molecular Biology ,Triple-negative breast cancer - Abstract
Triple negative breast cancer is an aggressive type of cancer that does not respond to hormonal therapy and current therapeutic strategies are accompanied by side effects due to cytotoxic actions on normal tissues. Therefore, there is a need for the identification of anti-cancer compounds with negligible effects on non-tumoral cells. Here we show that (−)‑oleocanthal (OLCT), a phenolic compound isolated from olive oil, selectively impairs MDA-MB-231 cell proliferation and viability without affecting the ability of non-tumoral MCF10A cells to proliferate or their viability. Similarly, OLCT selectively impairs the ability of MDA-MB-231 cells to migrate while the ability of MCF10A to migrate was unaffected. The effect of OLCT was not exclusive for triple negative breast cancer cells as we found that OLCT also attenuate cell viability and proliferation of MCF7 cells. Our results indicate that OLCT is unable to induce Ca2+ mobilization in non-tumoral cells. By contrast, OLCT induces Ca2+ entry in MCF7 and MDA-MB-231 cells, which is impaired by TRPC6 expression silencing. We have found that MDA-MB-231 and MCF7 cells overexpress the channel TRPC6 as compared to non-tumoral MCF10A and treatment with OLCT for 24–72 h downregulates TRPC6 expression in MDA-MB-231 cells. These findings indicate that OLCT impairs the ability of breast cancer cells to proliferate and migrate via downregulation of TRPC6 channel expression while having no effect on the biology of non-tumoral breast cells.
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- 2019
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22. Small Molecule-Based Enzyme Inhibitors in the Treatment of Primary Hyperoxalurias
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José A. Gómez-Vidal, Maria Dolores Moya-Garzon, Joaquín Altarejos, Alfonso Alejo-Armijo, Sofía Salido, Miguel X. Fernandes, Mónica Díaz-Gavilán, Juan R. Rodriguez-Madoz, and Eduardo Salido
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Drug ,analytical_chemistry ,liver selective distribution ,media_common.quotation_subject ,Medicine (miscellaneous) ,lcsh:Medicine ,Review ,Gene mutation ,Pharmacology ,03 medical and health sciences ,chemistry.chemical_compound ,0302 clinical medicine ,Pharmacokinetics ,In vivo ,Lactate dehydrogenase ,glycolate oxidase ,030304 developmental biology ,media_common ,chemistry.chemical_classification ,0303 health sciences ,oxalate ,hyperoxaluria ,Chemistry ,lcsh:R ,lactate dehydrogenase ,Small molecule ,In vitro ,inhibitor ,Enzyme ,small molecule drug ,030220 oncology & carcinogenesis - Abstract
Primary hyperoxalurias (PHs) are a group of inherited alterations of the hepatic glyoxylate metabolism. PHs classification based on gene mutations parallel a variety of enzymatic defects, and all involve the harmful accumulation of calcium oxalate crystals that produce systemic damage. These geographically widespread rare diseases have a deep impact in the life quality of the patients. Until recently, treatments were limited to palliative measures and kidney/liver transplants in the most severe forms. Efforts made to develop pharmacological treatments succeeded with the biotechnological agent lumasiran, a siRNA product against glycolate oxidase, which has become the first effective therapy to treat PH1. However, small molecule drugs have classically been preferred since they benefit from experience and have better pharmacological properties. The development of small molecule inhibitors designed against key enzymes of glyoxylate metabolism is on the focus of research. Enzyme inhibitors are successful and widely used in several diseases and their pharmacokinetic advantages are well known. In PHs, effective enzymatic targets have been determined and characterized for drug design and interesting inhibitory activities have been achieved both in vitro and in vivo. This review describes the most recent advances towards the development of small molecule enzyme inhibitors in the treatment of PHs, introducing the multi-target approach as a more effective and safe therapeutic option.
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- 2020
23. Synthesis of A-Type Proanthocyanidins and Their Analogues: A Comprehensive Review
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Joaquín Altarejos, Alfonso Alejo-Armijo, and Sofía Salido
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Chalcone ,endocrine system diseases ,Molecular Structure ,education ,food and beverages ,General Chemistry ,Chemistry Techniques, Synthetic ,Health benefits ,Combinatorial chemistry ,humanities ,chemistry.chemical_compound ,Monomer ,chemistry ,Proanthocyanidin ,health services administration ,Organic synthesis ,Proanthocyanidins ,General Agricultural and Biological Sciences - Abstract
Proanthocyanidins (PACs) are oligomers or polymers composed of units of flavanols. A-type PACs are a subclass of PACs characterized by the presence of at least a double linkage between two consecutive monomers of flavanol. These A-type PACs are found in some fruits and spices and possess potential health benefits as a result of their interesting biological activities, and consequently, their isolation and synthesis have given rise to great interest in the past. This review summarizes the synthetic efforts made to obtain both naturally occurring A-type PACs and their structurally simplified analogues. Most of the synthetic protocols reported involve the addition of a π-nucleophilic molecule over a molecule with two electrophilic carbons, such as a chalcone, a flavylium salt, or a flavanol derivative, among others. Synthesis of A-type PACs remains an issue at a very early stage of development compared to that of PACs with single linkages between monomers (B-type PACs), but the advances that are taking place in the last few years point to a significant development of the subject in the near future.
- Published
- 2020
24. Gene flow between diploid and tetraploid junipers - two contrasting evolutionary pathways in two Juniperus populations
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Nicolas Valentin, Carlos Salazar-Mendías, Perla Farhat, Silvia López-Udias, Robert P. Adams, Sonja Siljak-Yakovlev, Carlos Fabregat, Joaquín Altarejos, Institut de Biologie Intégrative de la Cellule (I2BC), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Cytométrie (CYTO), Département Plateforme (PF I2BC), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Biologie Intégrative de la Cellule (I2BC), and Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)
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0106 biological sciences ,0301 basic medicine ,Sympatry ,Gene Flow ,Triploid bridge ,Evolution ,Range (biology) ,Introgression ,[SDV]Life Sciences [q-bio] ,Population ,Zoology ,010603 evolutionary biology ,01 natural sciences ,Gene flow ,Polyploidy ,03 medical and health sciences ,QH359-425 ,Conifer evolution ,education ,Hybridization ,Ecology, Evolution, Behavior and Systematics ,Hybrid ,education.field_of_study ,biology ,15. Life on land ,biology.organism_classification ,Diploidy ,Tetraploidy ,030104 developmental biology ,Sympatric speciation ,Spain ,Juniperus ,Hybridization, Genetic ,Juniper ,Research Article - Abstract
Background Gene flow and polyploidy have been found to be important in Juniperus evolution. However, little evidence has been published elucidating the association of both phenomena in juniper taxa in the wild. Two main areas were studied in Spain (Eastern Iberian Range and Sierra de Baza) with both diploid and tetraploid taxa present in sympatry. Gene flow and ploidy level were assessed for these taxa and the resulted offspring. Results Twenty-two allo-triploid hybrids between J. sabina var. sabina and J. thurifera were found in the Eastern Iberian Range population. However, in the Sierra de Baza population no triploids were found. Instead, 18 allo-tetraploid hybrids between two tetraploid taxa: J. sabina var. balkanensis and J. thurifera were discovered. High genetic diversity was exhibited among the tetraploid hybrids at Sierra de Baza, in contrast to the genetically identical triploid hybrids at the Eastern Iberian Range; this suggests meiotic difficulties within the triploid hybrids. In addition, unidirectional gene flow was observed in both studied areas. Conclusion Polyploidy and hybridization can be complementary partners in the evolution of Juniperus taxa in sympatric occurrences. Juniperus was shown to be an ideal coniferous model to study these two phenomena, independently or in concert.
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- 2020
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25. Antimicrobial activity of phenolics isolated from the pruning wood residue of European plum (Prunus domestica L.)
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Macarena Martínez-Bailén, Antonio Gálvez, Juan Ortega-Vidal, Sofía Salido, Antonio Cobo, Joaquín Altarejos, and Elena Ortega-Morente
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Biocide ,biology ,Catechin ,Antimicrobial ,biology.organism_classification ,High-performance liquid chromatography ,chemistry.chemical_compound ,Prunus ,chemistry ,Glucoside ,Proanthocyanidin ,Food science ,Agronomy and Crop Science ,Bacteria - Abstract
European plum (Prunus domestica L.) is a tree cultivated in many countries for its edible fruits, and necessarily certain amounts of useless woody residues are generated every year during pruning works. The objectives of this research were to recover the phenolics present on that wood wastes and study their antimicrobial and antibiofilm activities against a selection of foodborne microorganisms, including multi-resistant strains. The isolation of components was carried out by combining fast centrifugal partition chromatography (FCPC) and semi-preparative high-performance liquid chromatography (HPLC), and the identification was achieved by conventional techniques. Nine compounds were identified: 2 flavan-3-ols [catechin (1) and epicatechin (2)]; 1 phenolic glucoside [annphenone (3)]; and 6 dimeric A-type proanthocyanidins (4–9). All of them have been reported in Prunus domestica by the first time in this work, with the exception of 1 and 2. Extracts, fractions and purified phenolics were submitted to antimicrobial and antibiofilm activity evaluations. The most significative antimicrobial effect was detected on the strain Enterobacter sp. UJA37p, previously isolated from organic tomato and with high tolerance to different biocides. All pure compounds showed MIC values of 100 μg/mL against this resistant bacterium. On the other hand, when bacteria were previously allowed to attach and form biofilm before treatments, we found interesting results in disruption of preformed biofilms with compound 7 [(+)-epiafzelechin-(2β→O→7,4β→8)-epicatechin], followed by compound 6 [(−)-ent-epiafzelechin-(2α→O→7,4α→8)-catechin] and compound 3 at a concentration of 0.1 μg/mL.
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- 2022
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26. Thermodynamic Stability of Flavylium Salts as a Valuable Tool To Design the Synthesis of A-Type Proanthocyanidin Analogues
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Joaquín Altarejos, Fernando Pina, A. Jorge Parola, Sofía Salido, and Alfonso Alejo-Armijo
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Proanthocyanidin ,010405 organic chemistry ,Computational chemistry ,Chemistry ,Organic Chemistry ,Chemical stability ,010402 general chemistry ,01 natural sciences ,A-type proanthocyanidin ,0104 chemical sciences - Abstract
A convenient method to synthesize A-type proanthocyanidin analogues from flavylium salts and π-nucleophiles has been developed. It was found that the thermodynamic stability of the starting flavylium salt, assessed by the measurement of the apparent acidity constant ( K'
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- 2018
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27. Synthesis and Evaluation of Antimicrobial and Antibiofilm Properties of A-Type Procyanidin Analogues against Resistant Bacteria in Food
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Antonio Gálvez, María Pilar Frías, Joaquín Altarejos, Alfonso Alejo-Armijo, Sofía Salido, Nicolás Glibota, and Elena Ortega-Morente
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0301 basic medicine ,030106 microbiology ,Microbial Sensitivity Tests ,Bacterial Physiological Phenomena ,medicine.disease_cause ,01 natural sciences ,Catechin ,03 medical and health sciences ,medicine ,Biflavonoids ,Proanthocyanidins ,Food science ,Gram ,Bacteria ,010405 organic chemistry ,Chemistry ,Biofilm ,Pathogenic bacteria ,General Chemistry ,Antimicrobial ,Anti-Bacterial Agents ,0104 chemical sciences ,Resistant bacteria ,Proanthocyanidin ,Biofilms ,Food Microbiology ,General Agricultural and Biological Sciences - Abstract
Natural A-type procyanidins have shown very interesting biological activities, such as their proven antiadherence properties against pathogenic bacteria. In order to find the structural features responsible for their activities, we describe herein the design and synthesis of six A-type procyanidin analogues and the evaluation of their antimicrobial and antibiofilm properties against 12 resistant bacteria, both Gram positive and Gram negative, isolated from organic foods. The natural A-type procyanidin A-2, which had known antiadherence activity, was also tested as a reference compound for the comparative studies. Within the series, analogue 4, which had a NO2 group on ring A, showed the highest antimicrobial activity (MIC of 10 μg/mL) and was one of the best molecules at preventing biofilm formation (up to 40% decreases at 100 μg/mL) and disrupting preformed biofilms (up to 40% reductions at 0.1 μg/mL). Structure–activity relationships are also analyzed.
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- 2018
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28. Synthesis of cassane-type diterpenes from abietane compounds: the first synthesis of taepeenin F
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Pablo J. Linares-Palomino, Rachid Chahboun, Enrique Alvarez-Manzaneda, Pilar Gutierrez, and Joaquín Altarejos
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010405 organic chemistry ,Stereochemistry ,Organic Chemistry ,010402 general chemistry ,Formyl group ,01 natural sciences ,0104 chemical sciences ,chemistry.chemical_compound ,chemistry ,Diterpene ,Oxidative cleavage ,Abietic acid ,After treatment ,Isopropyl ,Abietane - Abstract
The first synthesis of the aromatic cassane-type diterpene taepeenin F from abietic acid is reported. The key steps of the synthetic sequence are the ipso-substitution of the isopropyl group of a dehydroabietane derivative by a formyl group, after treatment with Cl2CHOMe and AlCl3, and the oxidative cleavage of a dihydronaphthalene intermediate. The deisopropylation reaction of dehydroabietane derivatives is revised and a complementary study on this subject is included. A mechanism for this reaction is postulated.
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- 2018
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29. Antimicrobial and antibiofilm activities of procyanidins extracted from laurel wood against a selection of foodborne microorganisms
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Sofía Salido, Elena Ortega-Morente, Joaquín Altarejos, María Pilar Frías, Nicolás Glibota, Antonio Gálvez, and Alfonso Alejo-Armijo
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0301 basic medicine ,Preservative ,Microorganism ,030106 microbiology ,Biofilm ,Ethyl acetate ,04 agricultural and veterinary sciences ,Bacterial growth ,Biology ,Antimicrobial ,medicine.disease_cause ,040401 food science ,Industrial and Manufacturing Engineering ,Microbiology ,03 medical and health sciences ,chemistry.chemical_compound ,0404 agricultural biotechnology ,Proanthocyanidin ,Listeria monocytogenes ,chemistry ,medicine ,Food Science - Abstract
Summary This study aimed to evaluate the antimicrobial and antibiofilm activities of two procyanidins isolated from an ethyl acetate extract of laurel wood against a selection of foodborne pathogens. The analysis of the extract by HPLC–DAD/ESI–MS allowed us to detect the presence of two procyanidins, which were selectively isolated and identified by chromatographic and spectroscopic means as cinnamtannin B-1 (1) and procyanidin B-2 (2). Procyanidins 1 and 2 exhibited two biological activities: inhibition of bacterial growth at high concentrations and prevention of biofilm formation at lower concentrations. Synergistic effect was also detected when both compounds were tested in combination against Listeria monocytogenes. Significant effects were also detected on disruption of preformed biofilm. The ability of procyanidins to inhibit microbial growth and biofilm formation and to synergistically work with each other may stimulate a market as natural food preservatives, and/or natural sanitisers for processing equipment where foodborne pathogens reside.
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- 2016
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30. Phenolic Compounds in Laurel Wood: a New Source of Proanthocyanidins
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Sofía Salido, Joaquín Altarejos, Alfonso Alejo-Armijo, and Almudena Tello-Abolafia
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0106 biological sciences ,Chemistry ,General Chemical Engineering ,02 engineering and technology ,General Chemistry ,021001 nanoscience & nanotechnology ,01 natural sciences ,food.food ,Horticulture ,Tree (data structure) ,Laurus nobilis ,food ,Hplc esi ms ,Proanthocyanidin ,010608 biotechnology ,General Materials Science ,0210 nano-technology ,Pruning - Abstract
Laurel tree (Laurus nobilis L.) wood is a byproduct of the pruning of this tree widely cultivated for its aromatic leaves. The phenolic composition of laurel wood has not been reported yet. The aim of this work was to study the phenolic profile of an ethyl acetate extract of laurel wood in order to know its potential as a source of antioxidants and valuable compounds. Three flavan-3-ols, 4 dimeric B-type proanthocyanidins, and 2 trimeric A-type procyanidins were isolated by preparative column chromatography and semi-preparative HPLC, using a fast online post-column radical scavenging detection technique as guidance. All isolated compounds were fully characterized by spectroscopic (NMR, IR, UV) and spectrometric (MS) techniques. In addition, 17 minor proanthocyanidins were tentatively identified by liquid chromatography coupled to mass spectrometry (HPLC–ESI–MS). The extract was dominated by the presence of cinnamtannin B-1, a bioactive trimeric A-type procyanidin reported as a strong antioxidant of commercial value. According to the chemical composition found, it can be concluded that laurel wood is a renewable source of potential bioactive phenolic compounds.
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- 2019
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31. Phenolic Components and Antioxidant Activity of Wood Extracts from 10 Main Spanish Olive Cultivars
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Joaquín Altarejos, Sofía Salido, Mercedes Pérez-Bonilla, and Robert P. Adams
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Spectrometry, Mass, Electrospray Ionization ,Iridoid ,medicine.drug_class ,Flavonoid ,Antioxidants ,Lignans ,chemistry.chemical_compound ,Phenols ,Species Specificity ,Oleuropein ,Olea ,Botany ,medicine ,Iridoids ,Cultivar ,Chromatography, High Pressure Liquid ,Flavonoids ,chemistry.chemical_classification ,Lignan ,biology ,Plant Extracts ,Free Radical Scavengers ,General Chemistry ,biology.organism_classification ,Wood ,Horticulture ,chemistry ,Spain ,General Agricultural and Biological Sciences ,Pruning - Abstract
The chemical composition and radical-scavenging activity of wood samples from 10 main Spanish olive cultivars were studied. The wood samples were collected during the pruning works from trees growing under the same agronomical and environmental conditions. The 10 ethyl acetate extracts were submitted to HPLC-DAD/ESI-MS analysis to determine the phenolic constituents. Seventeen compounds were identified (10 secoiridoids, 3 lignans, 2 phenol alcohols, 1 iridoid, and 1 flavonoid) by comparison with authentic samples. Significant quantitative and qualitative differences were found among olive cultivars. The lignan (+)-1-hydroxypinoresinol 1-O-β-d-glucopyranoside was the major compound in all olive cultivars, except in cultivars 'Farga' and 'Picual'. The multivariate analysis of all data revealed three sets of cultivars with similar compositions. Cultivars 'Gordal sevillana' and 'Picual' had the most distinct chemical profiles. With regard to the radical-scavenging activity, cultivar 'Picual', with oleuropein as the major phenolic, showed the highest activity (91.4 versus 18.6-32.7%).
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- 2015
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32. Evaluation of the antiaggregant activity of ascorbyl phenolic esters with antioxidant properties
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Ginés M. Salido, Joaquín Altarejos, Juan A. Rosado, Pedro C. Redondo, Esther Lopez, Sofía Salido, and María del Carmen Ortega-Liébana
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Blood Platelets ,Agonist ,endocrine system ,animal structures ,Antioxidant ,Platelet Aggregation ,Physiology ,medicine.drug_class ,animal diseases ,medicine.medical_treatment ,Drug Evaluation, Preclinical ,Ascorbic Acid ,Pharmacology ,Biochemistry ,Thrombin ,Phenols ,medicine ,Humans ,Platelet ,Calcium Signaling ,Platelet activation ,Phosphorylation ,Calcium metabolism ,Chemistry ,TOR Serine-Threonine Kinases ,Esters ,hemic and immune systems ,Free Radical Scavengers ,General Medicine ,Ascorbic acid ,eye diseases ,Platelet aggregation inhibitor ,Protein Processing, Post-Translational ,Platelet Aggregation Inhibitors ,medicine.drug - Abstract
Beneficial effects of the antioxidant L-ascorbic acid (Asc) in human health are well known. Its particular role in hemostasis deserves further consideration, since it has been described a dose-dependent effect of Asc in platelet activity. Contrary, it has been demonstrated that phenolic compounds have inhibitory effects on platelet aggregation stimulated by the physiological agonist thrombin (Thr). Here, we have evaluated the actions of three synthetic phenolic esters of Asc: L-ascorbyl 6-protocatechuate (Prot Asc), L-ascorbyl 6-gallate (Gal Asc), and L-ascorbyl 6-caffeate (Caf Asc). All these Asc derivatives exhibited greater radical scavenging activity than Asc, and in experiments using human platelets from healthy subjects, they do not evoke changes in platelet viability upon their administration. Nevertheless, these compounds altered platelet calcium homeostasis in response to Thr, although Prot Asc induced a smaller effect than Gal Asc, Caf Asc, and Asc. As a consequence, platelet aggregation was also impaired by these compounds, reporting Prot Asc and Caf Asc a weaker antiaggregant action than Gal Asc and Asc. Treatments with Gal Asc and Caf Asc altered in larger extent the phosphorylation pattern of pp60(Src) and mammalian target of rapamycin (mTOR) evoked by stimulating human platelets with Thr. Summarizing, Prot Asc is the ascorbyl phenolic ester with the strongest antioxidant properties and weakest antiaggregant actions, and its use as antioxidant may be safer than the rest of derivatives in order to prevent thrombotic alteration in patients that need treatment with antioxidant therapies.
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- 2015
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33. Effect of Methyl, Hydroxyl, and Chloro Substituents in Position 3 of 3',4',7-Trihydroxyflavylium: Stability, Kinetics, and Thermodynamics
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Sofía Salido, Alfonso Alejo-Armijo, A. Jorge Parola, Joaquín Altarejos, Luis Cabrita, Sandra Gago, Nuno Basílio, and Fernando Pina
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Organic Chemistry ,Kinetics ,Substituent ,Thermodynamics ,02 engineering and technology ,General Chemistry ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Photochemistry ,Mole fraction ,01 natural sciences ,Chloride ,Catalysis ,0104 chemical sciences ,Anthocyanidins ,chemistry.chemical_compound ,Chemical species ,Photochromism ,chemistry ,medicine ,Irradiation ,0210 nano-technology ,medicine.drug - Abstract
The effect of methyl, hydroxyl, and chloride substituents in position 3 of the 3′,4′,7-trihydroxyflavylium core structure was studied. The stability, relative energy of each of chemical species (thermodynamics), and their rates of interconversion (kinetics) are very dependent on these substituents. By comparing the mole fraction distribution at equilibrium of the three multistate systems with the parent 3′,4′,7-trihydroxyflavylium, introduction of a methyl substituent in position 3 increases the mole fraction of hemiketal at the expense of the trans-chalcone and increases the hydration rate very significantly; a hydroxyl substituent in position 3 gives rise to a degradation process, as observed in anthocyanidins. In the case of 3-chloro-3′,4′,7-trihydroxyflavylium, a dramatic increase of the flavylium cation acidity was observed and a photochromic system can be operated upon irradiation of the respective trans-chalcone in 1 m HCl. According to the photochromic response of 3,3′,4′,7-tetrahydroxyflavylium and 3′,4′,7-trihydroxyflavylium, some requirements for a good photochromic performance are discussed.
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- 2016
34. On-Line Radical Scavenging Detection and Characterization of Antioxidants from Artemisia herba-alba
- Author
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N. Dahmani-Hamzaoui, Aoumeur Baaliouamer, Joaquín Altarejos, Sofía Salido, and Pablo J. Linares-Palomino
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Chromatography ,Antioxidant ,biology ,DPPH ,Artemisia herba-alba ,medicine.medical_treatment ,Organic Chemistry ,biology.organism_classification ,Biochemistry ,Catalysis ,Inorganic Chemistry ,chemistry.chemical_compound ,Caffeoylquinic acid ,chemistry ,Drug Discovery ,medicine ,Organic chemistry ,Artemisia ,Physical and Theoretical Chemistry ,Scavenging - Abstract
Four caffeoylquinic acid (CQA) derivatives, 5-O-caffeoylquinic acid (1), 3,5-di-O-caffeoylquinic acid (3), 4,5-di-O-caffeoylquinic acid (4), and 3,4,5-tri-O-caffeoylquinic acid (5), have been isolated from Artemisia herba-alba growing wild in Algeria, using the on-line HPLCDADDPPH radical-scavenging detection technique as guidance. In the course of the purification work, the non-frequent (E)-2-(β-D-glucopyranosyloxy)-4-methoxycinnamic acid (2) has also been isolated. The CQAs showed fair-to-good antioxidant activities determined by the DPPH. scavenging assay. The structures of the five isolated compounds were determined by spectroscopic methods. The on-line HPLCDADDPPH technique allowed for a rapid pinpointing of antioxidants in the studied plant, accomplishing the facile guided isolation of the target molecules. Algerian A. herba-alba could be an interesting source of natural antioxidants that deserve further work.
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- 2012
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35. Antioxidant activity and free radical-scavenging capacity of a selection of wild-growing Colombian plants
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Juan Carlos Argoti, Joaquín Altarejos, Bernardo Ramírez, Braulio Insuasty, Pablo J. Linares-Palomino, and Sofía Salido
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Nutrition and Dietetics ,Antioxidant ,biology ,Traditional medicine ,Chemistry ,Baccharis ,DPPH ,medicine.medical_treatment ,Lepechinia conferta ,biology.organism_classification ,Quercus humboldtii ,chemistry.chemical_compound ,Botany ,medicine ,Lachemilla orbiculata ,Oleoresin ,Agronomy and Crop Science ,Scavenging ,Food Science ,Biotechnology - Abstract
BACKGROUND: The replacement of some synthetic food antioxidants by safe natural antioxidants has fostered research on the screening of raw materials to find new vegetable sources of antioxidants. In this study the antioxidant activity of eight wild-growing Colombian plants was assessed by four complementary assays. RESULTS: An evaluation of the antioxidant activity of ten ethanolic extracts from Baccharis chilco, Cinnamomum triplinerve, Ilex laurina, Lachemilla orbiculata, Lepechinia conferta, Quercus humboldtii, Rubus urticifolius and Tephrosia cinerea was carried out. Furthermore, the total phenolic content was determined by the Folin–Ciocalteu method, and the relationship between phenolic content and activity was also statistically investigated. Cinnamomum triplinerve, L. conferta and I. laurina were found to have the highest phenolic contents. Baccharis chilco, C. triplinerve, I. laurina, L. conferta, Q. humboldtii and R. urticifolius showed higher radical-scavenging activity (DPPH and superoxide assays) than commercial rosemary oleoresin (reference). Lachemilla orbiculata and R. urticifolius showed higher antioxidant activity (β-carotene-bleaching test) than the reference. The protection factor of all studied plant extracts was below that of the reference according to the Rancimat test. CONCLUSION: On the basis of the results obtained, C. triplinerve, Q. humboldtii and R. urticifolius seem to be the most promising species for further investigation in order to identify the compounds responsible for their activity. Copyright © 2011 Society of Chemical Industry
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- 2011
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36. Isolation of antioxidative secoiridoids from olive wood (Olea europaea L.) guided by on-line HPLC–DAD–radical scavenging detection
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Pieter de Waard, Mercedes Pérez-Bonilla, Pablo J. Linares-Palomino, Adolfo Sánchez, Joaquín Altarejos, Teris A. van Beek, and Sofía Salido
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extracts ,mill wastewaters ,Antioxidant ,jasminum polyanthum ,DPPH ,medicine.medical_treatment ,Biophysics ,Ethyl acetate ,Analytical Chemistry ,chemistry.chemical_compound ,Glucoside ,Oleuropein ,liquid-chromatography ,Jasminum polyanthum ,medicine ,Organic chemistry ,by-products ,VLAG ,glucosides ,natural antioxidants ,phenolic-compounds ,Chromatography ,biology ,plants ,Rosmarinic acid ,Organic Chemistry ,General Medicine ,biology.organism_classification ,Organische Chemie ,Biofysica ,chemistry ,Olea ,identification ,Food Science - Abstract
The woody portion of olive tree pruning is a source of natural antioxidants of potential interest for the food industry. This work deals with the isolation and identification of further antioxidants present in an ethyl acetate extract of olive ( Olea europaea L.) wood. Thus, a new secoiridoid, oleuropein-3″-methyl ether ( 1 ), together with six known secoiridoids, 7″ S -hydroxyoleuropein ( 2 ), jaspolyanoside ( 3 ), ligustroside 3′- O -β- d -glucoside ( 4 ), jaspolyoside ( 5 ), isojaspolyoside A ( 6 ) and oleuropein 3′- O -β- d -glucoside ( 7 ) were isolated by combining HPLC with fast on-line post-column radical scavenging activity evaluation. The structures of these compounds were determined by spectroscopic methods. The antioxidant activity of the pure compounds was determined by measuring the radical scavenging activity against 2,2-diphenyl-1-picrylhydrazyl radical (DPPH ). Compounds 2 , 5 and 7 displayed a higher antioxidative effect than the synthetic antioxidant BHT and lower than rosmarinic acid, whereas compounds 3 and 4 showed weak DPPH scavenging activity.
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- 2011
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37. Synthesis of (+)-Sclareolide Based on a Cyclic Enol Ether Ring Contraction Induced by Peroxy Acids
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Joaquín Altarejos, Adolfo Sánchez, Juan M. Castro, and Sofía Salido
- Subjects
chemistry.chemical_classification ,chemistry.chemical_compound ,Contraction (grammar) ,chemistry ,Double bond ,Organic Chemistry ,Enol ether ,Oxide ,Organic chemistry ,Oxidative cleavage ,Medicinal chemistry - Abstract
(+)-Sclareolide has been synthesised from (+)-sclareol oxide in one step in high yield, by treatment with peroxy acids under very mild conditions. The reaction pathway does not follow the usual oxidative cleavage of the double bond of (+)-sclareol oxide, but the key intermediate is a five-membered ring hemiketal. The direct conversion of a six-membered cyclic enol ether into a γ-lactone is described for the first time.
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- 2010
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38. Synthesis and Olfactory Evaluation of Bulky Moiety-Modified Analogues to the Sandalwood Odorant Polysantol®
- Author
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Sofía Salido, Manuel Nogueras, Concepción Badía, Pablo J. Linares-Palomino, Laura Chapado, Adolfo Sánchez, and Joaquín Altarejos
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Magnetic Resonance Spectroscopy ,Plant composition ,Santalum ,Pharmaceutical Science ,Article ,Analytical Chemistry ,nopol derivative ,lcsh:QD241-441 ,chemistry.chemical_compound ,Structure-Activity Relationship ,lcsh:Organic chemistry ,Drug Discovery ,Organic chemistry ,Structure–activity relationship ,Moiety ,Physical and Theoretical Chemistry ,Organic Chemicals ,odour evaluation ,sandalwood odorants ,Sandalwood ,Polycyclic Sesquiterpenes ,biology ,Molecular Structure ,Organic chemicals ,Organic Chemistry ,Butanone ,Polysantol® analogues ,biology.organism_classification ,chemistry ,Chemistry (miscellaneous) ,Odorants ,Molecular Medicine ,Aldol condensation ,Sesquiterpenes - Abstract
Five new bulky moiety-modified analogues of the sandalwood odorant Polysantol have been synthesized by aldol condensation of appropriate aldehydes with butanone, deconjugative alpha-methylation of the resulting alpha,beta-unsaturated ketones, and reduction of the corresponding beta,gamma-unsaturated ketones. The final compounds were evaluated organoleptically and one of them seemed to be of special interest for its natural sandalwood scent.
- Published
- 2009
39. Antihyperlipidemic Effects of Sour Cherries Characterized by Different In Vitro Antioxidant Power and Polyphenolic Composition
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Anna Blázovics, Éva Stefanovits-Bányai, Sofía Salido, Ibolya Kocsis, László Abrankó, A. Hegedűs, Nóra Papp, Erzsébet Fehér, Joaquín Altarejos, Klára Szentmihályi, and Hedvig Fébel
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Male ,Antioxidant ,Normal diet ,medicine.medical_treatment ,Flavonoid ,Hyperlipidemias ,Prunus avium ,Antioxidants ,Anthocyanins ,chemistry.chemical_compound ,stomatognathic system ,Species Specificity ,Hyperlipidemia ,Botany ,medicine ,Animals ,Food science ,Rats, Wistar ,Hypolipidemic Agents ,chemistry.chemical_classification ,Flavonoids ,Cholesterol ,Cholesterol, HDL ,food and beverages ,Polyphenols ,Cholesterol, LDL ,medicine.disease ,Dietary Fats ,Diet ,Rats ,chemistry ,Chemistry (miscellaneous) ,Polyphenol ,Anthocyanin ,Fruit ,Composition (visual arts) ,Food Science ,Phytotherapy - Abstract
The aims of the present study were to clarify in vivo effects of three sour cherry cultivars characterized by different polyphenolic composition in hyperlipidemic animals in a short term experiment. The three different sour cherry cultivars were chosen based on their total in vitro antioxidant capacity, total polyphenolic, monomeric anthocyanin and flavonoid content. Male Wistar rats were divided randomly into eight groups: rats kept on normal diet (control) and normal diet supplied with sour cherry powder of one of the three cultivars; others were kept on fat-rich diet and fat-rich diet supplied with sour cherry powder prepared from one of the three cultivars. The treatment lasted 10 days. Lyophilized sour cherry administered in the diet decreased both total cholesterol and LDL cholesterol levels, and increased the HDL cholesterol concentration in sera of hyperlipidemic animals. Significant differences were found in the efficacy of different sour cherry cultivars in case of hyperlipidemia. Sour cherries characterized by higher polyphenol content seem to have a more pronounced effect on serum cholesterol levels. Our results suggest that besides anthocyanins, colourless polyphenols also have lipid lowering effect.
- Published
- 2015
40. Seasonal Variation of Leaf, Stem and Umbel Ray Essential Oils ofBupleurum gibraltariumLam
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M. C. García-Vallejo, María José Pérez-Alonso, Carlos Fernández-López, Jesús Palá-Paúl, Joaquín Altarejos, Ana Fernández-Ocaña, Arturo Velasco-Negueruela, and Ana M. Camacho-Simarro
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Bupleurum ,Limonene ,Apiaceae ,2,3,4-trimethylbenzaldehyde ,biology ,Bupleurum gibraltarium ,Seasonal variation ,Umbel ,Sabinene ,General Chemistry ,Seasonality ,biology.organism_classification ,medicine.disease ,chemistry.chemical_compound ,chemistry ,Oil content ,α-pinene ,Botany ,Essential oil composition ,medicine ,Composition (visual arts) - Abstract
The yield and composition of essential oils from leaves, stems, umbel rays and also from whole aerial parts of Bupleurum gibraltarium Lam. (Apiaceae) were determined during the pre-flowering, full flowering, late flowering, and fruiting vegetative periods. A fruit sample was also studied for comparative purposes. Leaves (0.8–1.8% yield) and stems (0.3–0.7%) reached their maximum oil content during the late flowering period, whereas umbel rays (2.2–3.7%) reached it in full flowering. Oil samples were analyzed by capillary GC and GC/MS components which were found in amounts greater than 2% were selected to carry out a seasonal study. In the leaf oils, sabinene (12.0–33.9%) and limonene (7.8–23.4%) were the main components, the sabinene level being minimum in full flowering and maximum in fruiting. In stem oils, sabinene (4.7–21.6%) and 2,3,4-trimethylbenzaldehyde (9.3–13.6%) were the main components, the sabinene level being minimum in pre-flowering and maximum in full flowering. In umbel ray oils, sabinene (20.7–43.1%) was the first component in all the phenological periods, followed by α-pinene (7.3–28.2%). Both monoterpenes increased their levels in late flowering and reached minimum amounts in fruiting. © 2006, Taylor & Francis Group, LLC. All rights reserved.
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- 2006
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41. Synthesis and odour evaluation of stereoisomers of octahydrobenzopyran derivatives
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Sofía Salido, Joaquín Altarejos, Adolfo Sánchez, Pablo J. Linares-Palomino, and Manuel Nogueras
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chemistry.chemical_compound ,chemistry ,Bicyclic molecule ,Stereochemistry ,Yield (chemistry) ,Organic chemistry ,General Chemistry ,Carbon-13 NMR ,Ionone ,Chlorosulfonic acid ,Chemical synthesis ,Food Science - Abstract
The synthesis and isolation of the four racemic 2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-2H-1-benzopyran stereoisomers from β-ionone and α-ionone is reported. It was based on the cyclization of dihydro-β-ionone and dihydro-α-ionone with chlorosulfonic acid at low temperature to yield stereospecifically the trans-fused and cis-fused hexahydrobenzopyran derivatives, respectively. The direct cyclization of dihydro-β-ionol and dihydro-α-ionol under identical conditions was also explored. In addition to the complete spectroscopic characterization of every isolated isomer, a description of their olfactory properties is displayed. Copyright © 2006 John Wiley & Sons, Ltd.
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- 2006
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42. Enantiospecific synthesis, separation and olfactory evaluation of all diastereomers of a homologue of the sandalwood odorant Polysantol®
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Pablo J. Linares-Palomino, Manuel Nogueras, Juan M. Castro, Joaquín Altarejos, Adolfo Sánchez, and Sofía Salido
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chemistry.chemical_classification ,Sandalwood ,biology ,Stereochemistry ,Organic Chemistry ,Diastereomer ,biology.organism_classification ,Biochemistry ,Aldehyde ,Chloride ,chemistry.chemical_compound ,Organoleptic evaluation ,chemistry ,Drug Discovery ,medicine ,Organic chemistry ,Aldol condensation ,Derivatization ,medicine.drug - Abstract
The four stereoisomers of (5E)-4,4-dimethyl-6-(2′,2′,3′-trimethylcyclopent-3′-en-1′-yl)-hex-5-en-3-ol, a homologue of the valuable sandalwood-type odorant Polysantol®, were enantiospecifically synthesized from (+)- and (−)-α-pinene, through (−)- and (+)-campholenic aldehyde, by aldol condensation with 3-pentanone, deconjugative α-methylation and reduction. The mixtures of epimeric alcohols obtained after reduction were separated by means of derivatization with (−)-(1S)-camphanic chloride. The enantiomerically pure final products were evaluated organoleptically.
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- 2005
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43. Synthesis of Polysantol® and related sandalwood-type odorants using magnesium α-bromoketone enolates
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Pablo J. Linares-Palomino, Adolfo Sánchez, Juan M. Castro, Joaquín Altarejos, Manuel Nogueras, and Sofía Salido
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chemistry.chemical_classification ,Sandalwood ,biology ,Magnesium ,Organic Chemistry ,chemistry.chemical_element ,Alcohol ,biology.organism_classification ,Biochemistry ,Aldehyde ,Carbonyl group ,chemistry.chemical_compound ,chemistry ,Aldol reaction ,Drug Discovery ,Organic chemistry ,Molecule - Abstract
The syntheses of the commercial sandalwood-type odorant Polysantol ® and several structurally related compounds are described. The methodology followed is based on a selective and efficient magnesium-mediated aldol reaction of the starting material, α-campholenic aldehyde and different α-bromoketones. Dehydration of the resulting secondary alcohol and reduction of the carbonyl group allowed the completion of the syntheses of the target molecules in 30–56% overall yields.
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- 2004
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44. Composition and infraspecific variability of Artemisia herba-alba from southern Spain
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Sofía Salido, A. Sánchez, Eusebio Cano, Joaquín Altarejos, Luis Ruiz Valenzuela, and Manuel Nogueras
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biology ,Artemisia herba-alba ,Asteraceae ,biology.organism_classification ,Biochemistry ,law.invention ,chemistry.chemical_compound ,Taxon ,chemistry ,law ,Botany ,Artemisia ,Kovats retention index ,Composition (visual arts) ,Chrysanthenone ,Ecology, Evolution, Behavior and Systematics ,Essential oil - Abstract
The composition of the essential oils of 16 individual plants of Artemisia herba-alba Asso ssp. valentina (Lam.) Marcl. (at the full bloom stage) growing wild in four different locations from southern Spain were investigated by capillary GC and GC–MS in combination with retention indices. Among the 60 identified constituents (accounting for 80.6–95.0% of the oils), 33 have been reported for the first time in Spanish A. herba-alba oil and 17 of them have not been previously described in A. herba-alba oil. From the analysis of the oil samples, it could be deduced that a noticeable chemical polymorphism typified this taxon. Four groups of essential oils exhibited a single compound with percentages near 30% or higher: davanone, 1,8-cineole, chrysanthenone and cis-chrysanthenol. Two further oil types showed p-cymene and cis-chrysanthenyl acetate as major components in moderate amounts (ca. 20%). All of these types of essential oils have not been previously found in A. herba-alba from Spain and the appearance of such considerable amount of p-cymene is described here for the first time in A. herba-alba. # 2003 Published by Elsevier Ltd.
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- 2004
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45. Chlorosulfonic acid as a convenient electrophilic olefin cyclization agent
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Joaquín Altarejos, Sofía Salido, Pablo J. Linares-Palomino, and Adolfo Sánchez
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Olefin fiber ,Nucleophile ,Chemistry ,Fluorosulfonic acid ,Organic Chemistry ,Drug Discovery ,Electrophile ,Organic chemistry ,Benzopyrans ,Chlorosulfonic acid ,Biochemistry - Abstract
Among several sulfonic acids studied (MeSO3H, p-TsOH, H2SO4, ClSO3H, FSO3H), the scarcely used chlorosulfonic acid showed to be an efficient agent for electrophilic olefin cyclizations with internal nucleophilic termination, in a similar manner that is well-established with fluorosulfonic acid. Its availability, lower price and relatively lesser handling problems makes ClSO3H an advantageous cyclizing agent particularly for high-scale applications. The stereochemical outcome of these cyclizations has been rationalized.
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- 2003
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46. Chemical Composition and Seasonal Variations of Rosemary Oil from Southern Spain
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Joaquín Altarejos, Manuel Nogueras, Sofía Salido, Pascual Luque, and Adolfo Saánchez
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Chemotype ,General Chemistry ,law.invention ,Borneol ,Steam distillation ,chemistry.chemical_compound ,Horticulture ,Camphor ,chemistry ,Linalool ,law ,Myrcene ,Botany ,Camphene ,Essential oil - Abstract
The composition of 12 essential oil samples, obtained by steam distillation of twigs of rosemary (Rosmarinus officinalis L.) harvested in four different locations from southern Spain and during three phenological stages, has been analyzed by capillary GC and GC/MS in combination with retention indices. Quantitative data relative to 53 constituents (accounting for 96.7-99.2% of the oils), 12 of which being reported for the first time in Spanish rosemary oil, are described. All samples studied belong to the chemotype α-pinene/l,8-cineole/eamphor, the main and characteristic components being camphor (17.2-34.7%), α-pinene (10.2-21.6%), 1,8-cineole (12.1-14.4%), camphene (5.2-8.6%), borneol (3.2-7.7%), β-pinene (2.3-7.5%), verbenone (2.2-5.8%), β-caryophyllene (1.8-5.1%), limonene (2.0-3.8%), α-terpineol (1.2-2.5%), myrcene (0.9-4.5%), p-cymene (0.2-3.4%), bornyl acetate (0.2-2.3%), linalool (0.3-1.0%) and terpinen-4-ol (0.4-0.9%). The effect of harvest time on the oil production and chemical composi...
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- 2003
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47. Synthesis of Ambrox® from labdanolic acid
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Sofía Salido, Adolfo Sánchez, Joaquín Altarejos, Manuel Nogueras, and Juan M. Castro
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Solvent ,chemistry.chemical_compound ,chemistry ,Reagent ,Yield (chemistry) ,Organic Chemistry ,Drug Discovery ,Diol ,Side chain ,Organic chemistry ,Biochemistry ,Terpenoid - Abstract
A synthesis of the valuable amber-type odorant Ambrox® from labdanolic acid (main diterpenoid of the acid fraction of non-polar extracts of Cistus ladaniferus L.) is reported. The conversion is based on (a) the α,β-dehydrogenation of methyl labdanolate using an organoselenium reagent, (b) subsequent oxidative degradations of the side chain, and (c) final acid-promoted cyclization of the resulting tetranorlabdan-8α,12-diol. The influence of the temperature and solvent in the cyclization of the diol with p-toluenesulfonic acid is also described. Thus, Ambrox® has been obtained by a six-step procedure in 33% overall yield from methyl labdanolate.
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- 2002
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48. Chemical Composition of the Essential Oil ofArtemisia herba-albaAsso ssp.valentina(Lam.) Marcl
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Adolfo Sánchez, Sofía Salido, Joaquín Altarejos, and Manuel Nogueras
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p-Cymene ,biology ,Traditional medicine ,Chemistry ,Artemisia herba-alba ,General Chemistry ,biology.organism_classification ,Sesquiterpene ,law.invention ,chemistry.chemical_compound ,Camphor ,law ,Myrcene ,Botany ,Artemisia ,Chrysanthenone ,Essential oil - Abstract
The composition of the oil, steam-distilled from aerial parts of Artemisia herha-alba Asso ssp. valentina (Lam.) Marcl. (Asteraceae) collected from the south of Spain, has been analyzed by GC/MS. Among the 65 constituents investigated (representing 93.6 % of the oil composition), 61 were identified (90.3% of the oil composition). The major constituents detected were the sesquiterpene davanone (18.1%) and monoterpenes p-cymene (13.5%), 1,8-cineole (10.2%), chrysanthenone (6.7%), cis-chrysanthenyl acetate (5.6%), γ-terpinene (5.5%), myrcene (5.1%) and camphor (4.0%). The oil was dominated by monoterpenes (ca. 66% of the oil), p-menthane and pinane being the most representative skeleta of the group. The oil sample studied did not contain thujones, unlike most A. herba-alba oils described in the literature.
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- 2001
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49. Composition of the Essential Oils from Galls and Aerial Parts ofPistacia lentiscusL
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Pilar Gómez Pérez, Joaquín Altarejos, Ana Claudia Aparecida Mariano Fernandez, Ana Camacho, and Carlos Fernandez
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Limonene ,beta-Pinene ,alpha-Pinene ,biology ,Monoterpene ,General Chemistry ,Sesquiterpene ,biology.organism_classification ,chemistry.chemical_compound ,chemistry ,Pistacia lentiscus ,Botany ,Anacardiaceae ,Chemical composition - Abstract
The chemical composition of the essential oils obtained from the galls and the aerial parts of Pistacia lentiscus L. (Anacardiaceae) was analyzed by GC/MS. Among the 58 constituents identified (representing 82.8% of the oil composition) sesquiterpene hydrocarbons predominated (ca. 47%), β-caryophyllene (13-1%), δ-cadinene (8.1%) and Germacrene D (6.8%) being the major components. Although galls and oils of the aerial parts were similar from a qualitative viewpoint, the latter oil was somewhat more complex (73 components identified, accounting for 85.4% of the oil) and the monoterpene hydrocarbons fraction (ca. 35%) was now dominant in the oil, α-pinene (13.0%), β-caryophyllene (6.9%), limonene and β-phellandrene (5.4%), β-pinene (4.9%) and p-cymene (4.7%) being the main components.
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- 2000
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50. The Leaf Essential Oils and Taxonomy ofJuniperus oxycedrusL. subsp.oxycedrus,subsp.badia(H. Gay) Debeaux, and subsp.macrocarpa(Sibth. & Sm.) Ball
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Joaquín Altarejos, Robert P. Adams, Ana Camacho, and Carlos Fernandez
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Limonene ,biology ,Cupressaceae ,Sabinene ,General Chemistry ,Subspecies ,biology.organism_classification ,Terpene ,chemistry.chemical_compound ,chemistry ,Myrcene ,Botany ,Taxonomy (biology) ,Juniperus oxycedrus - Abstract
The leaf essential oils of Juniperus oxycedrus L. subsp. oxycedrus, subsp. badia (H. Gay) Debeaux and subsp. macrocarpa (Sm.) Ball have been analyzed by GC/MS. One hundred twenty two compounds were found in these three subspecies. The leaf oils of J. oxycedrus were dominated by α-pinene (25–43%), and limonene (4.5–28%), with moderate amounts of β-pinene, myrcene, p-cymene, β-phellandrene and manoyl oxide, whereas the leaf oils of J. oxycedrus subsp. badia were dominated by α-pinene and germacrene D with variable amounts of manoyl oxide and moderate amounts of α-campholenal, β-bourbenene and several unknown sesquiterpenes. The oils of subsp. badia contained nine unknown sesquiterpenes that were only found in this taxon. The oil of subsp. macrocarpa was dominated by sabinene and α-pinene with moderate amounts of p-cymene, γ-terpinene and terpinen-4-ol. Chemically, the three subspecies appear to be distinct and this warrants the continued recognition of these subspecies.
- Published
- 1999
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