The Experts below are selected from a list of 360 Experts worldwide ranked by ideXlab platform
Maria F. Duarte - One of the best experts on this subject based on the ideXlab platform.
-
ultrasound assisted extraction of Cynaropicrin from cynara cardunculus leaves optimization using the response surface methodology and the effect of pulse mode
Industrial Crops and Products, 2020Co-Authors: Luisa A Neves, Teresa Brás, Joao G Crespo, Ana F C Paulino, Maria F. DuarteAbstract:Abstract In this study, conditions for ultrasound assisted extraction (UAE) of Cynaropicrin from Cynara cardunculus leaves by assessing the effect of pulsed mode and different duty cycles were optimized. Pulse mode presented a reduction of 45 % on energy consumption/ g Cynaropicrin extracted, comparatively to continuous mode, and a duty cycle of 25 % presented the highest kinetic rate between the duty cycles under study, with a lower number of pulse repetitions necessary to reach a steady state conditions. The extraction methodology was further optimized by response surface methodology (RSM), using a Box-Bhenken design with 3 factors (solid/liquid ratio, amplitude and temperature), and 3 levels for correlation of independent variables with the extraction yield (mg of Cynaropicrin/g dry weight) and Cynaropicrin concentration (mg Cynaropicrin /g extract). Experimental results were fitted to a second order polynomial model, using multiple regression and analysis of variance to determine the fitness of the model. Optimal conditions were found for a solid/liquid ratio of 1/27, amplitude of 67 % and temperature of 44 °C, with a predicted value of 23.99 mg/g DW and 192.23 mg/g extract for extraction yield and Cynaropicrin concentration, respectively. The predicted values fit the experimental ones, with a 95 % confidence level showing the accuracy of the model. The results obtained suggest the applicability of the UAE optimization methodologies described, for Cynaropicrin extraction from Cynara cardunculus leaves, illustrating its potential application on biotechnological and agro food industries.
-
effect of extraction methodologies and solvent selection upon Cynaropicrin extraction from cynara cardunculus leaves
Separation and Purification Technology, 2020Co-Authors: Maria F. Duarte, Teresa Brás, Luisa A Neves, Joao G CrespoAbstract:Abstract Conventional extraction technologies to recover sesquiterpene lactones, relay on long extraction periods, with high temperatures, and use of organic solvents, often leading to degradation of target compounds. Within the present study, the effect of environmentally friendly, and economically viable methodologies, namely ultrasound assisted extraction, using biocompatible solvents, upon Cynaropicrin, a sesquiterpene lactone found in Cynara cardunculus leaves was evaluated. Hansen solubility parameters, Cynaropicrin extraction yield and energy consumption were evaluated. The ultrasound assisted extraction, using ethanol, showed to be the best Cynaropicrin extraction methodology, leading to a reduction of 99% of extraction time (7 h to 5 min), a 30% increase of the Cynaropicrin extraction yield (40.32–55.00 mg/g Dry Weight), and a 97% reduction of energy consumption (1.160–0.027 kWh/gCynaropicrin), compared to Soxhlet extraction. The results obtained from this study may be easily transposed to other sesquiterpene lactones extraction processes, with industrial relevance, as an alternative to conventional extraction methodologies.
-
Biosynthesis and bioactivity of Cynara cardunculus L. guaianolides and hydroxycinnamic acids: a genomic, biochemical and health-promoting perspective
Phytochemistry Reviews, 2019Co-Authors: Patrícia A. B. Ramos, Ana M. Ferro, M. Margarida Oliveira, António Jorge Silvestre, Sónia Gonçalves, Carmen S.r. Freire, Maria F. DuarteAbstract:Cynara cardunculus health benefits have aroused much interest, leading to the discovery of valuable bioactive compounds with a crucial role in plant defence. Guaianolides and hydroxycinnamic acids, mainly represented by Cynaropicrin and chlorogenic acid, constitute the major secondary metabolites in leaves (9.5% and 10.4% dry weight, respectively). These compounds evidence biological activity, namely antioxidant, antitumoral, hepatoprotective, antimicrobial and anti-hyperlipidemic effects. Therefore, numerous efforts have been undertaken in this species to unveil the biosynthetic pathways of such compounds, by means of genomic and biochemical approaches, which could support advances, via breeding programs, in C. cardunculus chemical composition and, consequently, in the improvement of its extracts biological activity. Addressing this challenge, relevant genes in Cynaropicrin biosynthesis, as well as in chlorogenic acid biosynthesis have been widely studied. The present review highlights the current knowledge on the biosynthesis and distribution of guaianolides and hydroxycinnamic acids, especially of Cynaropicrin and chlorogenic acid in C. cardunculus, as well as their association with plant defence mechanisms and human health-promoting effects, prospecting the valorisation of this Mediterranean species as a potential source of bioactive compounds for food, nutraceutical and pharmaceutical purposes.
-
antiproliferative effects of cynara cardunculus l var altilis dc lipophilic extracts
International Journal of Molecular Sciences, 2016Co-Authors: Patrícia A. B. Ramos, Carmen S.r. Freire, Ângela R. Guerra, Olinda Guerreiro, Armando J D Silvestre, Sonia A O Santos, Helena Oliveira, Maria F. DuarteAbstract:Besides being traditionally used to relieve hepatobiliary disorders, Cynara cardunculus L. has evidenced anticancer potential on triple-negative breast cancer (TNBC). This study highlights the antiproliferative effects of lipophilic extracts from C. cardunculus L. var. altilis (DC) leaves and florets, and of their major compounds, namely Cynaropicrin and taraxasteryl acetate, against MDA-MB-231 cells. Our results demonstrated that MDA-MB-231 cells were much less resistant to leaves extract (IC50 10.39 µg/mL) than to florets extract (IC50 315.22 µg/mL), during 48 h. Moreover, leaves extract and Cynaropicrin (IC50 6.19 µg/mL) suppressed MDA-MB-231 cells colonies formation, via an anchorage-independent growth assay. Leaves extract and Cynaropicrin were also assessed regarding their regulation on caspase-3 activity, by using a spectrophotometric assay, and expression levels of G2/mitosis checkpoint and Akt signaling pathway proteins, by Western blotting. Leaves extract increased caspase-3 activity, while Cynaropicrin did not affect it. Additionally, they caused p21Waf1/Cip1 upregulation, as well as cyclin B1 and phospho(Tyr15)-CDK1 accumulation, which may be related to G2 cell cycle arrest. They also downregulated phospho(Ser473)-Akt, without changing total Akt1 level. Cynaropicrin probably contributed to leaves extract antiproliferative action. These promising insights suggest that cultivated cardoon leaves lipophilic extract and Cynaropicrin may be considered toward a natural-based therapeutic approach on TNBC.
-
Lipophilic Extracts of Cynara cardunculus L. var. altilis (DC): A Source of Valuable Bioactive Terpenic Compounds
2016Co-Authors: Patrícia A. B. Ramos, Maria F. Duarte, Carmen S.r. Freire, Olinda Guerreiro, Ângela R. Guerra, Artur M. S. Silva, Armando J D SilvestreAbstract:Lipophilic extracts of Cynara cardunculus L. var. altilis (DC) from the south of Portugal (Baixo Alentejo) were studied by gas chromatography–mass spectrometry. One sesquiterpene lactone, four pentacyclic triterpenes, and four sterols were reported for the first time as cultivated cardoon components, namely, deacylCynaropicrin, β- and α-amyrin, lupenyl and ψ-taraxasteryl acetates, stigmasterol, 24-methylenecholesterol, campesterol, and Δ5-avenasterol. In addition, other new compounds were identified: ten fatty acids, eight long-chain aliphatic alcohols, and six aromatic compounds. Four triterpenyl fatty acid esters were also detected. Sesquiterpene lactones and pentacyclic triterpenes were the major lipophilic families, representing respectively 2–46% and 10–89% of the detected compounds. Cynaropicrin was the most abundant sesquiterpene lactone, while taraxasteryl acetate was the main pentacyclic triterpene. Fatty acids and sterols, mainly hexadecanoic acid and β-sitosterol, were present at lower amounts (1–20% and 1–11% of the detected compounds). Long-chain aliphatic alcohols and aromatic compounds were detected at reduced abundances (1–6% of the detected compounds)
Jules Beekwilder - One of the best experts on this subject based on the ideXlab platform.
-
Accumulation of Cynaropicrin in globe artichoke and localization of enzymes involved in its biosynthesis
Plant Science, 2015Co-Authors: K. Eljounaidi, Andrea Moglia, Cinzia Comino, Katarina Cankar, Jules Beekwilder, A. Genre, Alain Hehn, Frédéric Bourgaud, S. LanteriAbstract:Globe artichoke (Cynara cardunculus var. scolymus) belongs to the Asteraceae family, in which one of the most biologically significant class of secondary metabolites are sesquiterpene lactones (STLs). In globe artichoke the principal STL is the Cynaropicrin, which contributes to approximately 80% of its characteristic bitter taste. Cynaropicrin content was assessed in globe artichoke tissues and was observed to accumulate in leaves of different developmental stages. In the receptacle, a progressive decrease was observed during inflorescence development, while the STL could not be detected in the inflorescence bracts. Almost undetectable amounts were found in the roots and inflorescence stems at the commercial stage. Cynaropicrin content was found to correlate with expression of genes encoding CcGAS, CcGAO and CcCOS, which are involved in the STL biosynthesis. A more detailed study of leaf material revealed that Cynaropicrin predominantly accumulates in the trichomes, and not in the apoplastic cavity fluids. Analysis of the promoter regions of CcGAO and CcCOS revealed the presence of L1-box motifs, which confers trichome-specific expression in Arabidopsis, suggesting that Cynaropicrin is not only stored but also synthesized in trichomes. A transient expression of GFP fusion proteins was performed in Nicotiana benthamiana plants: the CcGAS fluorescence signal was located in the cytoplasm while the CcGAO and CcCOS localized to the endoplasmatic reticulum.
-
Cytochrome P450s from Cynara cardunculus L. CYP71AV9 and CYP71BL5, catalyze distinct hydroxylations in the sesquiterpene lactone biosynthetic pathway
Plant Science, 2014Co-Authors: Kaouthar Eljounaidi, Barbara Menin, Andrea Moglia, Cinzia Comino, Katarina Cankar, Sergio Lanteri, Alain Hehn, Frédéric Bourgaud, Harro Bouwmeester, Jules BeekwilderAbstract:Cynara cardunculus (Asteraceae) is a cross pollinated perennial crop which includes the two cultivated taxa globe artichoke and cultivated cardoon. The leaves of these plants contain high concentrations of sesquiterpene lactones (STLs) among which Cynaropicrin is the most represented, and has recently attracted attention because of its therapeutic potential as anti-tumor and anti-photoaging agent. Costunolide is considered the common precursor of the STLs and three enzymes are involved in its biosynthetic pathway: i.e. the germacrene A synthase (GAS), the germacrene A oxidase (GAO) and the costunolide synthase (COS). Here we report on the isolation of two P450 genes, (i.e. CYP71AV9 and CYP71BL5), in a set of 19,000 C cardunculus unigenes, and their functional characterization in yeast and in planta. The metabolite analyses revealed that the co-expression of CYP71AV9 together with GAS resulted in the biosynthesis of germacra-1(10),4,11(13)-trien-12-oic acid in yeast. The co-expression of CYP71BL5 and CYP71AV9 with GAS led to biosynthesis of the free costunolide in yeast and costunolide conjugates in Nicotiana benthamiana, demonstrating their involvement in STL biosynthesis as GAO and COS enzymes. The substrate specificity of CYP71AV9 was investigated by testing its ability to convert amorpha-4,11-diene, (+)-germacrene D and cascarilladiene to their oxidized products when co-expressed in yeast with the corresponding terpene synthases.
-
genetic mapping and characterization of the globe artichoke germacrene a synthase gene encoding the first dedicated enzyme for biosynthesis of the bitter sesquiterpene lactone Cynaropicrin
Plant Science, 2012Co-Authors: Barbara Menin, Hj Bouwmeester, Andrea Moglia, Cinzia Comino, Ezio Portis, Katarina Cankar, Sergio Lanteri, Jules BeekwilderAbstract:Abstract Globe artichoke (Cynara cardunculus var. scolymus L., Asteraceae) is a perennial crop traditionally consumed as a vegetable in the Mediterranean countries and rich in nutraceutically and pharmaceutically active compounds, including phenolic and terpenoid compounds. Its bitter taste is caused by its high content of sesquiterpene lactones (STLs), such as Cynaropicrin. The biosynthetic pathway responsible for STL biosynthesis in globe artichoke is unknown, but likely proceeds through germacrene A, as has been shown for other Asteraceae species. Here, we investigated the accumulation of Cynaropicrin in different tissues of globe artichoke, and compared it to accumulation of phenolic compounds. Cynaropicrin concentration was highest in old leaves. A putative germacrene A synthase (GAS) gene was identified in a set of ∼19,000 globe artichoke unigenes. When heterologously expressed in Escherichia coli, the putative globe artichoke GAS converted farnesyl diphosphate (FPP) into (+)-germacrene A. Among various tissues assayed, the level of globe artichoke GAS expression was highest in mature (six week old) leaves. A sequence polymorphism within a mapping population parent allowed the corresponding GAS gene to be positioned on a genetic map. This study reports the isolation, expression and mapping of a key gene involved in STL biosynthesis in C. cardunculus. This is a good basis for further investigation of this pathway.
-
Genetic mapping and characterization of the globe artichoke (+)-germacrene A synthase gene, encoding the first dedicated enzyme for biosynthesis of the bitter sesquiterpene lactone Cynaropicrin
Plant Science, 2012Co-Authors: Barbara Menin, Hj Bouwmeester, Andrea Moglia, Cinzia Comino, Ezio Portis, Katarina Cankar, Sergio Lanteri, Jules BeekwilderAbstract:Abstract Globe artichoke (Cynara cardunculus var. scolymus L., Asteraceae) is a perennial crop traditionally consumed as a vegetable in the Mediterranean countries and rich in nutraceutically and pharmaceutically active compounds, including phenolic and terpenoid compounds. Its bitter taste is caused by its high content of sesquiterpene lactones (STLs), such as Cynaropicrin. The biosynthetic pathway responsible for STL biosynthesis in globe artichoke is unknown, but likely proceeds through germacrene A, as has been shown for other Asteraceae species. Here, we investigated the accumulation of Cynaropicrin in different tissues of globe artichoke, and compared it to accumulation of phenolic compounds. Cynaropicrin concentration was highest in old leaves. A putative germacrene A synthase (GAS) gene was identified in a set of ∼19,000 globe artichoke unigenes. When heterologously expressed in Escherichia coli, the putative globe artichoke GAS converted farnesyl diphosphate (FPP) into (+)-germacrene A. Among various tissues assayed, the level of globe artichoke GAS expression was highest in mature (six week old) leaves. A sequence polymorphism within a mapping population parent allowed the corresponding GAS gene to be positioned on a genetic map. This study reports the isolation, expression and mapping of a key gene involved in STL biosynthesis in C. cardunculus. This is a good basis for further investigation of this pathway.
Teresa Brás - One of the best experts on this subject based on the ideXlab platform.
-
ultrasound assisted extraction of Cynaropicrin from cynara cardunculus leaves optimization using the response surface methodology and the effect of pulse mode
Industrial Crops and Products, 2020Co-Authors: Luisa A Neves, Teresa Brás, Joao G Crespo, Ana F C Paulino, Maria F. DuarteAbstract:Abstract In this study, conditions for ultrasound assisted extraction (UAE) of Cynaropicrin from Cynara cardunculus leaves by assessing the effect of pulsed mode and different duty cycles were optimized. Pulse mode presented a reduction of 45 % on energy consumption/ g Cynaropicrin extracted, comparatively to continuous mode, and a duty cycle of 25 % presented the highest kinetic rate between the duty cycles under study, with a lower number of pulse repetitions necessary to reach a steady state conditions. The extraction methodology was further optimized by response surface methodology (RSM), using a Box-Bhenken design with 3 factors (solid/liquid ratio, amplitude and temperature), and 3 levels for correlation of independent variables with the extraction yield (mg of Cynaropicrin/g dry weight) and Cynaropicrin concentration (mg Cynaropicrin /g extract). Experimental results were fitted to a second order polynomial model, using multiple regression and analysis of variance to determine the fitness of the model. Optimal conditions were found for a solid/liquid ratio of 1/27, amplitude of 67 % and temperature of 44 °C, with a predicted value of 23.99 mg/g DW and 192.23 mg/g extract for extraction yield and Cynaropicrin concentration, respectively. The predicted values fit the experimental ones, with a 95 % confidence level showing the accuracy of the model. The results obtained suggest the applicability of the UAE optimization methodologies described, for Cynaropicrin extraction from Cynara cardunculus leaves, illustrating its potential application on biotechnological and agro food industries.
-
effect of extraction methodologies and solvent selection upon Cynaropicrin extraction from cynara cardunculus leaves
Separation and Purification Technology, 2020Co-Authors: Maria F. Duarte, Teresa Brás, Luisa A Neves, Joao G CrespoAbstract:Abstract Conventional extraction technologies to recover sesquiterpene lactones, relay on long extraction periods, with high temperatures, and use of organic solvents, often leading to degradation of target compounds. Within the present study, the effect of environmentally friendly, and economically viable methodologies, namely ultrasound assisted extraction, using biocompatible solvents, upon Cynaropicrin, a sesquiterpene lactone found in Cynara cardunculus leaves was evaluated. Hansen solubility parameters, Cynaropicrin extraction yield and energy consumption were evaluated. The ultrasound assisted extraction, using ethanol, showed to be the best Cynaropicrin extraction methodology, leading to a reduction of 99% of extraction time (7 h to 5 min), a 30% increase of the Cynaropicrin extraction yield (40.32–55.00 mg/g Dry Weight), and a 97% reduction of energy consumption (1.160–0.027 kWh/gCynaropicrin), compared to Soxhlet extraction. The results obtained from this study may be easily transposed to other sesquiterpene lactones extraction processes, with industrial relevance, as an alternative to conventional extraction methodologies.
-
haplotype analysis of the germacrene a synthase gene and association with Cynaropicrin content and biological activities in cynara cardunculus
Molecular Genetics and Genomics, 2018Co-Authors: Patrícia A. B. Ramos, Ângela R. Guerra, Teresa Brás, Ana Margarida Ferro, Paula Parreira, Olinda GuerreiroAbstract:Cynara cardunculus: L. represents a natural source of terpenic compounds, with the predominant molecule being Cynaropicrin. Cynaropicrin is gaining interest since it has been correlated to anti-hyperlipidaemia, antispasmodic and cytotoxicity activity against leukocyte cancer cells. The objective of this work was to screen a collection of C. cardunculus, from different origins, for new allelic variants in germacrene A synthase (GAS) gene involved in the Cynaropicrin biosynthesis and correlate them with improved Cynaropicrin content and biological activities. Using high-resolution melting, nine haplotypes were identified. The putative impact of the identified allelic variants in GAS protein was evaluated by bioinformatic tools and polymorphisms that putatively lead to protein conformational changes were described. Additionally, Cynaropicrin and main pentacyclic triterpenes contents, and antithrombin, antimicrobial and antiproliferative activities were also determined in C. cardunculus leaf lipophilic-derived extracts. In this work we identified allelic variants with putative impact on GAS protein, which are significantly associated with Cynaropicrin content and antiproliferative activity. The results obtained suggest that the identified polymorphisms should be explored as putative genetic markers correlated with biological properties in Cynara cardunculus.
Armando J D Silvestre - One of the best experts on this subject based on the ideXlab platform.
-
extraction and recovery processes for Cynaropicrin from cynara cardunculus l using aqueous solutions of surface active ionic liquids
Biophysical Reviews, 2018Co-Authors: Emanuelle L P De Faria, Carmen S.r. Freire, Melissa V Gomes, Ana Filipa M Claudio, Armando J D Silvestre, Mara G FreireAbstract:Due to the wide range of relevant biological activities and high commercial value of Cynaropicrin, and aiming at developing cost-effective processes, aqueous solutions of ionic liquids (ILs) were investigated for the extraction and recovery of Cynaropicrin from the leaves of Cynara cardunculus L. Both cationic (1-alkyl-3-methylimidazolium chloride) and anionic (cholinium carboxylate) surface-active ILs were investigated, as well as a wide range of conventional surfactants and molecular organic solvents, allowing us to conclude that aqueous solutions of cationic surface-active ILs display a better performance for the extraction of Cynaropicrin. Operational conditions were optimized, leading to a Cynaropicrin extraction yield of 3.73 wt%. The recycling of both the biomass and the solvent were further investigated to appraise the extraction media saturation and to achieve a higher Cynaropicrin extraction yield (6.47 wt%). Finally, it was demonstrated that 65 wt% of the extracted Cynaropicrin can be efficiently recovered by precipitation from the IL aqueous extract through the addition of water as anti-solvent, allowing us to put forward both the extraction and recovery processes of the target value-added compound from biomass followed by solvent recycling. This approach opens the door to the development of more sustainable processes using aqueous solutions of ILs instead of the volatile organic solvents commonly used in biomass processing.
-
deep eutectic solvents as efficient media for the extraction and recovery of Cynaropicrin from cynara cardunculus l leaves
International Journal of Molecular Sciences, 2017Co-Authors: Emanuelle L P De Faria, Carmen S.r. Freire, Ana Filipa M Claudio, Mara G Freire, Rafael Do S Carmo, Armando J D SilvestreAbstract:In recent years a high demand for natural ingredients with nutraceutical properties has been witnessed, for which the development of more environmentally-friendly and cost-efficient extraction solvents and methods play a primary role. In this perspective, in this work, the application of deep eutectic solvents (DES), composed of quaternary ammonium salts and organic acids, as alternative solvents for the extraction of Cynaropicrin from Cynara cardunculus L. leaves was studied. After selecting the most promising DES, their aqueous solutions were investigated, allowing to obtain a maximum Cynaropicrin extraction yield of 6.20 wt %, using 70 wt % of water. The sustainability of the extraction process was further optimized by carrying out several extraction cycles, reusing either the biomass or the aqueous solutions of DES. A maximum Cynaropicrin extraction yield of 7.76 wt % by reusing the solvent, and of 8.96 wt % by reusing the biomass, have been obtained. Taking advantage of the Cynaropicrin solubility limit in aqueous solutions, water was added as an anti-solvent, allowing to recover 73.6 wt % of the extracted Cynaropicrin. This work demonstrates the potential of aqueous solutions of DES for the extraction of value-added compounds from biomass and the possible recovery of both the target compounds and solvents.
-
antiproliferative effects of cynara cardunculus l var altilis dc lipophilic extracts
International Journal of Molecular Sciences, 2016Co-Authors: Patrícia A. B. Ramos, Carmen S.r. Freire, Ângela R. Guerra, Olinda Guerreiro, Armando J D Silvestre, Sonia A O Santos, Helena Oliveira, Maria F. DuarteAbstract:Besides being traditionally used to relieve hepatobiliary disorders, Cynara cardunculus L. has evidenced anticancer potential on triple-negative breast cancer (TNBC). This study highlights the antiproliferative effects of lipophilic extracts from C. cardunculus L. var. altilis (DC) leaves and florets, and of their major compounds, namely Cynaropicrin and taraxasteryl acetate, against MDA-MB-231 cells. Our results demonstrated that MDA-MB-231 cells were much less resistant to leaves extract (IC50 10.39 µg/mL) than to florets extract (IC50 315.22 µg/mL), during 48 h. Moreover, leaves extract and Cynaropicrin (IC50 6.19 µg/mL) suppressed MDA-MB-231 cells colonies formation, via an anchorage-independent growth assay. Leaves extract and Cynaropicrin were also assessed regarding their regulation on caspase-3 activity, by using a spectrophotometric assay, and expression levels of G2/mitosis checkpoint and Akt signaling pathway proteins, by Western blotting. Leaves extract increased caspase-3 activity, while Cynaropicrin did not affect it. Additionally, they caused p21Waf1/Cip1 upregulation, as well as cyclin B1 and phospho(Tyr15)-CDK1 accumulation, which may be related to G2 cell cycle arrest. They also downregulated phospho(Ser473)-Akt, without changing total Akt1 level. Cynaropicrin probably contributed to leaves extract antiproliferative action. These promising insights suggest that cultivated cardoon leaves lipophilic extract and Cynaropicrin may be considered toward a natural-based therapeutic approach on TNBC.
-
Lipophilic Extracts of Cynara cardunculus L. var. altilis (DC): A Source of Valuable Bioactive Terpenic Compounds
2016Co-Authors: Patrícia A. B. Ramos, Maria F. Duarte, Carmen S.r. Freire, Olinda Guerreiro, Ângela R. Guerra, Artur M. S. Silva, Armando J D SilvestreAbstract:Lipophilic extracts of Cynara cardunculus L. var. altilis (DC) from the south of Portugal (Baixo Alentejo) were studied by gas chromatography–mass spectrometry. One sesquiterpene lactone, four pentacyclic triterpenes, and four sterols were reported for the first time as cultivated cardoon components, namely, deacylCynaropicrin, β- and α-amyrin, lupenyl and ψ-taraxasteryl acetates, stigmasterol, 24-methylenecholesterol, campesterol, and Δ5-avenasterol. In addition, other new compounds were identified: ten fatty acids, eight long-chain aliphatic alcohols, and six aromatic compounds. Four triterpenyl fatty acid esters were also detected. Sesquiterpene lactones and pentacyclic triterpenes were the major lipophilic families, representing respectively 2–46% and 10–89% of the detected compounds. Cynaropicrin was the most abundant sesquiterpene lactone, while taraxasteryl acetate was the main pentacyclic triterpene. Fatty acids and sterols, mainly hexadecanoic acid and β-sitosterol, were present at lower amounts (1–20% and 1–11% of the detected compounds). Long-chain aliphatic alcohols and aromatic compounds were detected at reduced abundances (1–6% of the detected compounds)
Carmen S.r. Freire - One of the best experts on this subject based on the ideXlab platform.
-
Biosynthesis and bioactivity of Cynara cardunculus L. guaianolides and hydroxycinnamic acids: a genomic, biochemical and health-promoting perspective
Phytochemistry Reviews, 2019Co-Authors: Patrícia A. B. Ramos, Ana M. Ferro, M. Margarida Oliveira, António Jorge Silvestre, Sónia Gonçalves, Carmen S.r. Freire, Maria F. DuarteAbstract:Cynara cardunculus health benefits have aroused much interest, leading to the discovery of valuable bioactive compounds with a crucial role in plant defence. Guaianolides and hydroxycinnamic acids, mainly represented by Cynaropicrin and chlorogenic acid, constitute the major secondary metabolites in leaves (9.5% and 10.4% dry weight, respectively). These compounds evidence biological activity, namely antioxidant, antitumoral, hepatoprotective, antimicrobial and anti-hyperlipidemic effects. Therefore, numerous efforts have been undertaken in this species to unveil the biosynthetic pathways of such compounds, by means of genomic and biochemical approaches, which could support advances, via breeding programs, in C. cardunculus chemical composition and, consequently, in the improvement of its extracts biological activity. Addressing this challenge, relevant genes in Cynaropicrin biosynthesis, as well as in chlorogenic acid biosynthesis have been widely studied. The present review highlights the current knowledge on the biosynthesis and distribution of guaianolides and hydroxycinnamic acids, especially of Cynaropicrin and chlorogenic acid in C. cardunculus, as well as their association with plant defence mechanisms and human health-promoting effects, prospecting the valorisation of this Mediterranean species as a potential source of bioactive compounds for food, nutraceutical and pharmaceutical purposes.
-
extraction and recovery processes for Cynaropicrin from cynara cardunculus l using aqueous solutions of surface active ionic liquids
Biophysical Reviews, 2018Co-Authors: Emanuelle L P De Faria, Carmen S.r. Freire, Melissa V Gomes, Ana Filipa M Claudio, Armando J D Silvestre, Mara G FreireAbstract:Due to the wide range of relevant biological activities and high commercial value of Cynaropicrin, and aiming at developing cost-effective processes, aqueous solutions of ionic liquids (ILs) were investigated for the extraction and recovery of Cynaropicrin from the leaves of Cynara cardunculus L. Both cationic (1-alkyl-3-methylimidazolium chloride) and anionic (cholinium carboxylate) surface-active ILs were investigated, as well as a wide range of conventional surfactants and molecular organic solvents, allowing us to conclude that aqueous solutions of cationic surface-active ILs display a better performance for the extraction of Cynaropicrin. Operational conditions were optimized, leading to a Cynaropicrin extraction yield of 3.73 wt%. The recycling of both the biomass and the solvent were further investigated to appraise the extraction media saturation and to achieve a higher Cynaropicrin extraction yield (6.47 wt%). Finally, it was demonstrated that 65 wt% of the extracted Cynaropicrin can be efficiently recovered by precipitation from the IL aqueous extract through the addition of water as anti-solvent, allowing us to put forward both the extraction and recovery processes of the target value-added compound from biomass followed by solvent recycling. This approach opens the door to the development of more sustainable processes using aqueous solutions of ILs instead of the volatile organic solvents commonly used in biomass processing.
-
deep eutectic solvents as efficient media for the extraction and recovery of Cynaropicrin from cynara cardunculus l leaves
International Journal of Molecular Sciences, 2017Co-Authors: Emanuelle L P De Faria, Carmen S.r. Freire, Ana Filipa M Claudio, Mara G Freire, Rafael Do S Carmo, Armando J D SilvestreAbstract:In recent years a high demand for natural ingredients with nutraceutical properties has been witnessed, for which the development of more environmentally-friendly and cost-efficient extraction solvents and methods play a primary role. In this perspective, in this work, the application of deep eutectic solvents (DES), composed of quaternary ammonium salts and organic acids, as alternative solvents for the extraction of Cynaropicrin from Cynara cardunculus L. leaves was studied. After selecting the most promising DES, their aqueous solutions were investigated, allowing to obtain a maximum Cynaropicrin extraction yield of 6.20 wt %, using 70 wt % of water. The sustainability of the extraction process was further optimized by carrying out several extraction cycles, reusing either the biomass or the aqueous solutions of DES. A maximum Cynaropicrin extraction yield of 7.76 wt % by reusing the solvent, and of 8.96 wt % by reusing the biomass, have been obtained. Taking advantage of the Cynaropicrin solubility limit in aqueous solutions, water was added as an anti-solvent, allowing to recover 73.6 wt % of the extracted Cynaropicrin. This work demonstrates the potential of aqueous solutions of DES for the extraction of value-added compounds from biomass and the possible recovery of both the target compounds and solvents.
-
antiproliferative effects of cynara cardunculus l var altilis dc lipophilic extracts
International Journal of Molecular Sciences, 2016Co-Authors: Patrícia A. B. Ramos, Carmen S.r. Freire, Ângela R. Guerra, Olinda Guerreiro, Armando J D Silvestre, Sonia A O Santos, Helena Oliveira, Maria F. DuarteAbstract:Besides being traditionally used to relieve hepatobiliary disorders, Cynara cardunculus L. has evidenced anticancer potential on triple-negative breast cancer (TNBC). This study highlights the antiproliferative effects of lipophilic extracts from C. cardunculus L. var. altilis (DC) leaves and florets, and of their major compounds, namely Cynaropicrin and taraxasteryl acetate, against MDA-MB-231 cells. Our results demonstrated that MDA-MB-231 cells were much less resistant to leaves extract (IC50 10.39 µg/mL) than to florets extract (IC50 315.22 µg/mL), during 48 h. Moreover, leaves extract and Cynaropicrin (IC50 6.19 µg/mL) suppressed MDA-MB-231 cells colonies formation, via an anchorage-independent growth assay. Leaves extract and Cynaropicrin were also assessed regarding their regulation on caspase-3 activity, by using a spectrophotometric assay, and expression levels of G2/mitosis checkpoint and Akt signaling pathway proteins, by Western blotting. Leaves extract increased caspase-3 activity, while Cynaropicrin did not affect it. Additionally, they caused p21Waf1/Cip1 upregulation, as well as cyclin B1 and phospho(Tyr15)-CDK1 accumulation, which may be related to G2 cell cycle arrest. They also downregulated phospho(Ser473)-Akt, without changing total Akt1 level. Cynaropicrin probably contributed to leaves extract antiproliferative action. These promising insights suggest that cultivated cardoon leaves lipophilic extract and Cynaropicrin may be considered toward a natural-based therapeutic approach on TNBC.
-
Lipophilic Extracts of Cynara cardunculus L. var. altilis (DC): A Source of Valuable Bioactive Terpenic Compounds
2016Co-Authors: Patrícia A. B. Ramos, Maria F. Duarte, Carmen S.r. Freire, Olinda Guerreiro, Ângela R. Guerra, Artur M. S. Silva, Armando J D SilvestreAbstract:Lipophilic extracts of Cynara cardunculus L. var. altilis (DC) from the south of Portugal (Baixo Alentejo) were studied by gas chromatography–mass spectrometry. One sesquiterpene lactone, four pentacyclic triterpenes, and four sterols were reported for the first time as cultivated cardoon components, namely, deacylCynaropicrin, β- and α-amyrin, lupenyl and ψ-taraxasteryl acetates, stigmasterol, 24-methylenecholesterol, campesterol, and Δ5-avenasterol. In addition, other new compounds were identified: ten fatty acids, eight long-chain aliphatic alcohols, and six aromatic compounds. Four triterpenyl fatty acid esters were also detected. Sesquiterpene lactones and pentacyclic triterpenes were the major lipophilic families, representing respectively 2–46% and 10–89% of the detected compounds. Cynaropicrin was the most abundant sesquiterpene lactone, while taraxasteryl acetate was the main pentacyclic triterpene. Fatty acids and sterols, mainly hexadecanoic acid and β-sitosterol, were present at lower amounts (1–20% and 1–11% of the detected compounds). Long-chain aliphatic alcohols and aromatic compounds were detected at reduced abundances (1–6% of the detected compounds)
