4.8 Article

Enhanced extraction and biological activity of 7-hydroxymatairesinol obtained from Norway spruce knots using aqueous solutions of ionic liquids

期刊

GREEN CHEMISTRY
卷 19, 期 11, 页码 2626-2635

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/c7gc01091e

关键词

-

资金

  1. project CICECO-Aveiro Institute of Materials
  2. FCT [POCI-01-0145-FEDER-007679, UID/CTM/50011/2013, SFRH/BD/92200/2013]
  3. project DeepBiorefinery [PTDC/AGR-TEC/1191/2014]
  4. national funds through the FCT/MEC
  5. FEDER
  6. COST Action [CM 1206 EXIL - Exchange on Ionic Liquids]
  7. Fundação para a Ciência e a Tecnologia [SFRH/BD/92200/2013] Funding Source: FCT

向作者/读者索取更多资源

In the past few years, an increasing demand for therapeutic drugs obtained from natural products has been faced. Amongst the bioactive natural compounds with pharmacological properties, 7-hydroxy-matairesinol (HMR) has been commercially available since 2006 as a nutritional supplement due to its anticarcinogenic and antioxidative properties. The extraction of HMR from biomass is usually performed with sequential soxhlet extractions using volatile organic solvents (e.g. acetone, and water-acetone and water-ethanol mixtures). To avoid the use of volatile organic solvents, aqueous solutions of analogues of glycine-betaine ionic liquids (AGB-ILs) were here studied as alternative solvents for the extraction of HMR from knots of Norway spruce trees. A response surface methodology (RSM) was used to optimize the extraction operational parameters, in which extraction yields up to 9.46 wt% were obtained with aqueous solutions of AGB-ILs at 1.5 M and 25 degrees C. Furthermore, the cytotoxicity of the IL aqueous solutions containing the HMR extract was assessed in a macrophage cell line, as well as their anti-inflammatory potential via reduction of lipopolysaccharide-induced cellular oxidative stress. It was found that the antioxidant and anti-inflammatory potentials of IL aqueous solutions enriched in HMR are more promising than the recovered HMR-rich solid extracts and that these solutions can be safely used in nutraceutical and cosmetic applications. These results bring new perspectives into the design of new integrated approaches for the extraction and direct application of naturally derived high-value compounds using adequate ILs, without requiring an additional step involving the target product recovery and solvent recycling.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.8
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

Article Environmental Sciences

The role of biomass elemental composition and ion-exchange in metal sorption by algae

Ana R. F. Carreira, Telma Veloso, Ines P. E. Macario, Joana L. Pereira, Sonia P. M. Ventura, Helena Passos, Joao A. P. Coutinho

Summary: This study evaluated the metal sorption capacity of six macroalgae, two microalgae, and three cyanobacteria for Co2+, Cu2+, Ni2+, and Zn2+. Brown macroalgae, particularly Undaria pinnatifida, showed the highest metal sorption capacity. Overall, macroalgae performed better than microalgae, followed by cyanobacteria. Carboxyl groups were identified as the main functional groups involved in metal sorption, and all biomass samples were selective to Cu2+. The release of K+ and Ca2+ during the metal sorption process indicated an ion-exchange mechanism, except for red macroalgae.

CHEMOSPHERE (2023)

Article Engineering, Chemical

Supported ionic liquids as customizable materials to purify immunoglobulin G

Emanuel Capela, Jessica Bairos, Augusto Q. Pedro, Marcia C. Neves, M. Raquel Aires-Barros, Ana M. Azevedo, Joao A. P. Coutinho, Ana P. M. Tavares, Mara G. Freire

Summary: This work demonstrates that materials modified with ionic liquids (ILs) can be effectively used for the selective adsorption and purification of antibodies, such as IgG, from complex matrices. The developed strategy showed good purification results in various IgG-containing matrices and preserved the structural integrity and biological activity of IgG. This suggests that ILs have the potential to replace costly chromatographic columns currently used for IgG purification.

SEPARATION AND PURIFICATION TECHNOLOGY (2023)

Article Chemistry, Multidisciplinary

Use of Tunable Copolymers in Aqueous Biphasic Systems for Extractive Bioconversion Aimed at Continuous Fructooligosaccharide Production

Carlos M. N. Mendonc, Nathalia V. Verissimo, Wellison A. . Pereira, Paula M. Cunha, Michele Vitolo, Attilio Converti, Kiki Adi Kurnia, Fernando Segato, Pamela O. S. de Azevedo, Mara G. Freire, Koen Venema, Joao H. P. M. Santos, Ricardo P. S. Oliveira

Summary: Aqueous biphasic systems (ABSs) based on sodium polyacrylate (NaPA), ethylene oxide/propylene oxide (EO/PO) polymers, and (EO)x-(PO)y-(EO)x triblock copolymers were prepared and applied for continuous fructooligosaccharide (FOS) production and separation. The hydrophilicity/hydrophobicity balance of EO/PO had a significant effect on ABS formation. Different carbohydrates and levansucrase showed different partition behavior in these ABSs. By selecting the appropriate ABS composition, high yields of FOS and selective partitioning could be achieved. COSMO-RS suggested that ABS formation was due to competition between NaPA and polymers/copolymers to form hydrogen bonds with water molecules.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2023)

Article Engineering, Chemical

Using the SAFT-?-Mie to Generate Coarse-Grained Force Fields Useable in Molecular Dynamics Simulations: Describing the Micellar Phases of Polyalkylglycols in Aqueous Solutions

Goncalo M. C. Silva, German Perez-Sanchez, Diego A. Pantano, Sophie Loehle, Joao A. P. Coutinho

Summary: In this study, the SAFT-gamma-Mie equation of state was used to develop coarse-grained molecular models for describing micellization phenomena in a top-down approach. Polyethylene oxide (PEO)/polypropylene oxide (PPO) triblock copolymers in aqueous solutions were selected as the case study. The model was successfully fitted to reproduce the thermophysical properties and liquid-liquid phase diagrams of PEO/PPO oligomers and their mixtures with water. Molecular dynamics simulations showed the formation of spherical micelles with star-shaped or flower-shaped morphology at low concentrations, and the formation of larger micelles or aggregates at higher concentrations.

INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH (2023)

Correction Engineering, Chemical

Experimental and CPA EoS Description of the Key Components in the BTX Separation from Gasolines by Extractive Distillation with Tricyanomethanide-Based Ionic Liquids (vol 59, pg 15058, 2020)

Miguel Ayuso, Andre M. Palma, Marcos Larriba, Noemi Delgado-Mellado, Julian Garcia, Francisco Rodriguez, Joao A. P. Coutinho, A. P. Coutinho, Pedro J. Carvalho, Pablo Navarro

INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH (2023)

Article Chemistry, Multidisciplinary

Rationalizing the Design of Pluronics-Surfactant Mixed Micelles through Molecular Simulations and Experiments

Divya Patel, German Perez-Sanchez, Miguel Jorge, Debes Ray, Vinod K. . Aswal, Ketan Kuperkar, Joao A. P. Coutinho, Pratap Bahadur

Summary: In this study, the effects of cationic surfactants on the morphology of triblock copolymer nanoaggregates were investigated. The results from experiments, scattering data analysis, and molecular dynamics simulations provided a deep insight into the interactions controlling micellar aggregation in the mixed systems.

LANGMUIR (2023)

Article Biochemistry & Molecular Biology

Jucara Fruit (Euterpe Edulis Martius) Valorization Combining Emergent Extraction Technologies and Aqueous Solutions of Alkanediols

Bruna P. Soares, Ana M. Ferreira, Marina Justi, Luiz Gustavo Goncalves Rodrigues, J. Vladimir Oliveira, Simao P. Pinho, Joao A. P. Coutinho

Summary: Anthocyanins from jucara fruits were extracted using biobased solvents, 1,2-alkanediols and glycerol ethers, through either pressurized liquid extraction (PLE) or ultrasound-assisted extraction (UAE). The optimized PLE conditions resulted in 23.1 mg(anthocyanins)center dot g(dry biomass)(-1), while the UAE conditions with 1,2-propanediol yielded 50 mg(anthocyanins)center dot g(dry biomass)(-1). The biobased solvent solutions exhibited higher anthocyanin yields and antioxidant capacity compared to water and ethanolic extracts.

MOLECULES (2023)

Article Chemistry, Analytical

Combined Use of Ionic Liquid-Based Aqueous Biphasic Systems and Microfluidic Devices for the Detection of Prostate-Specific Antigen

Filipa C. Flora, Sofia B. Relvas, Francisca A. e Silva, Mara G. Freire, Virginia Chu, Joao Pedro Conde

Summary: Prostate cancer (PCa) is a major global health concern, and improved diagnostic strategies are urgently needed. This study shows that prostate-specific antigen (PSA) can be detected through an immunoassay performed in a microbead-based microfluidic device after being extracted and purified from a serum sample using an aqueous biphasic system (ABS). Ionic liquids (ILs) and polymers were used in combination with buffered salts to optimize the extraction process. The results demonstrate the potential of this method for future point-of-care measurements.

BIOSENSORS-BASEL (2023)

Article Chemistry, Multidisciplinary

Aqueous biphasic systems comprising analogues of glycine-betaine ionic liquids: Toward greener separation platforms

Ines S. Cardoso, Filipe H. B. Sosa, Armando J. D. Silvestre, Anthony Robert, Mara G. Freire, Aminou Mohamadou

Summary: The use of biobased and bioactive compounds has led to the development of sustainable extraction and purification processes using ionic liquids. In this study, six novel analogues of glycine-betaine ILs (AGB-ILs) were investigated for their potential use in IL-based ABS. The synthesized ILs showed relatively low ecotoxicity and good thermal stability. The extraction efficiency of furfural using AGB-ILs-based ABS was found to be up to 98%, suggesting the potential of these novel ABS for separation of bioactive compounds.

SUSTAINABLE CHEMISTRY AND PHARMACY (2023)

Review Chemistry, Multidisciplinary

Metal biosorption onto non-living algae: a critical review on metal recovery from wastewater

Ana R. F. Carreira, Helena Passos, Joao A. P. Coutinho

Summary: The widespread presence of metals in water bodies has driven the development of platforms for their removal and recovery. Biosorption, specifically using algae, has emerged as a sustainable and cost-effective method for metal removal from wastewater. However, there are still gaps in the research, such as limited studies in natural wastewater and a lack of consideration for ion and metal competition. This study explores the application of non-living algae for metal recovery and compares their sorption capacity with other wastewater matrices, as well as evaluating the cost performance compared to commercial and waste-based sorbents.

GREEN CHEMISTRY (2023)

Article Chemistry, Multidisciplinary

A lignin-based membrane fabricated with a deep eutectic solvent

Abaynesh Yihdego Gebreyohannes, Sandra L. L. Aristizabal, Liliana Silva, Eyad A. A. Qasem, Stefan Chisca, Lakshmeesha Upadhyaya, Daniyah Althobaiti, Joao A. P. Coutinho, Suzana P. P. Nunes

Summary: Membrane technology is a sustainable process of molecular separation with lower energy consumption. Currently, most membranes are made from petroleum-based polymers and organic solvents, which are not environmentally friendly. We propose a sustainable membrane fabrication method using lignin dissolved in a green deep eutectic solvent. The resulting membrane has the desired molecular weight cut-off for applications in the pharmaceutical and chemical industries.

GREEN CHEMISTRY (2023)

Article Chemistry, Multidisciplinary

Sustainable keratin recovery process using a bio-based ionic liquid aqueous solution and its techno-economic assessment

Cariny Polesca, Amir Al Ghatta, Helena Passos, Joao A. P. Coutinho, Jason P. Hallett, Mara G. Freire

Summary: This study successfully dissolved chicken feathers in an aqueous solution of bio-based ionic liquid, achieving efficient and environmentally friendly keratin recovery. Under optimal recovery conditions, a recovery rate of 93% was achieved, and the ionic liquid showed reusable properties. Techno-economic assessment showed that the produced keratin can be commercialized, with a minimum selling price of $22 per kg and low CO2 emission.

GREEN CHEMISTRY (2023)

Article Chemistry, Physical

The path towards type V deep eutectic solvents: inductive effects and steric hindrance in the system tert-butanol plus perfluoro tert-butanol

Ines C. M. Vaz, Ana I. M. C. Lobo Ferreira, Goncalo M. C. Silva, Pedro Morgado, Dinis O. Abranches, Margarida Bastos, Luis M. N. B. F. Santos, Eduardo J. M. Filipe, Joao A. P. Coutinho

Summary: The solid-liquid phase behavior of perfluoro-tert-butanol and tert-butanol was investigated using experimental and theoretical methods. The study revealed the formation of co-crystals and identified two eutectic points in the binary mixture. The results showed that the fluorination of tertiary alcohols can be used to tune the mixing properties and solid-liquid phase diagrams.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2023)

Article Chemistry, Physical

Using COSMO-RS to design organic biphasic systems containing deep eutectic solvents for the separation of natural compounds

Jean -Baptiste Chagnoleau, Nicolas Papaiconomou, Xavier Fernandez, Joao A. P. Coutinho

Summary: This study evaluates the potential of the conductor-like screening model for designing biphasic systems for natural compound separation. The model accurately predicts binodal curves and phases composition and shows excellent agreement with experimental data for partition coefficients of natural compounds. The model is able to capture the influence of changes in system composition on partition coefficients.

JOURNAL OF MOLECULAR LIQUIDS (2024)

Article Chemistry, Physical

Exploring asymmetry induced entropy in tetraalkylammonium-urea DES systems: what can be learned from inelastic neutron scattering?

Catarina F. Araujo, Paulo Ribeiro-Claro, Pedro D. Vaz, Svemir Rudic, Rafael A. F. Serrano, Liliana P. Silva, J. A. P. Coutinho, Mariela M. Nolasco

Summary: This study investigates the behavior of deep eutectic solvents (DES) using inelastic neutron scattering (INS) spectroscopy. By calculating the vibrational modes of pure compounds and analyzing the spectra of binary mixtures, deviations from ideality in the mixtures of tetraalkylammonium salts with urea are observed. Unlike other systems, the deviation from ideality in the deep eutectic system comprised of [N2,2,2,1]Cl and urea is attributed to entropic rather than enthalpic factors.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2023)

Article Chemistry, Multidisciplinary

The synergy of in situ-generated Ni0 and Ni2P to enhance CO adsorption and protonation for selective CH4 production from photocatalytic CO2 reduction

Xuemei Liu, Chaonan Cui, Shuoshuo Wei, Jinyu Han, Xinli Zhu, Qingfeng Ge, Hua Wang

Summary: This study presents a new strategy for designing efficient photocatalysts that can convert CO2 into hydrocarbons by utilizing synergistic catalytic sites. The findings provide a solution for the selective photocatalytic reduction of CO2 to CH4.

GREEN CHEMISTRY (2024)

Article Chemistry, Multidisciplinary

Cu-Catalyzed, electron-relayed three-component synthesis of 2-alkenylbenzothiazoles with cathodic ammonia evolution

Chengxian Hu, Dan Wang, Lu Wang, Ying Fu, Zhengyin Du

Summary: A novel one-pot, three-component reaction conducted under electrochemical conditions was studied. The reaction involved 2-aminothiophenols, aldehydes, and malononitrile, using TBABF4 as an electrolyte and CuI as a catalyst. The proposed reaction mechanism suggested that CuI served as an electron relay. This method offers simplified operation, high atom economy, and mild reaction conditions.

GREEN CHEMISTRY (2024)

Article Chemistry, Multidisciplinary

Iridium-catalyzed asymmetric, complete hydrogenation of pyrimidinium salts under batch and flow

Zhi Yang, Yu Chen, Linxi Wan, Yuxiao Li, Dan Chen, Jianlin Tao, Pei Tang, Fen-Er Chen

Summary: A highly enantioselective method for the complete hydrogenation of pyrimidinium salts using Ir/(S,S)-f-Binaphane complex as the catalyst was developed. This method provides easy access to fully saturated chiral hexahydropyrimidines, which are prevalent in many bioactive molecules. The reactions exhibit high yields and enantioselectivities under mild reaction conditions without additives. Successful application of this methodology in a continuous flow fashion further extends its practical utility.

GREEN CHEMISTRY (2024)

Article Chemistry, Multidisciplinary

Spatiotemporal dynamics of cellulose during enzymatic hydrolysis studied by infrared spectromicroscopy

Tina Jeoh, Jennifer Danger Nill, Wujun Zhao, Sankar Raju Narayanasamy, Liang Chen, Hoi-Ying N. Holman

Summary: In this study, the enzymatic hydrolysis of cellulose was investigated using real-time infrared spectromicroscopy. The spatial heterogeneity of cellulose was found to impact the hydrolysis kinetics. Hydration affected cellulose ordering, and Cel7A preferentially removed less extensively hydrogen bonded cellulose.

GREEN CHEMISTRY (2024)

Article Chemistry, Multidisciplinary

Efficient nickel-catalysed telomerisation on glycerol carbonate: a new linker route for lignin functionalisation

Tiphaine Richard, Walid Abdallah, Xavier Trivelli, Mathieu Sauthier, Clement Dumont

Summary: An effective method of grafting functionalities onto lignin based on glycerol carbonate has been developed using an efficient nickel-catalysed telomerisation reaction. This method allows lignin to have new reactive functions and reduces the glass transition temperatures of modified lignins, thereby expanding the application range of lignin-based resins.

GREEN CHEMISTRY (2024)

Article Chemistry, Multidisciplinary

Sustainable electrocatalytic oxidation of N-alkylamides to acyclic imides using H2O

Jing Qi, Xiyan Wang, Gan Wang, Srinivas Reddy Dubbaka, Patrick ONeill, Hwee Ting Ang, Jie Wu

Summary: This study presents a green and environmentally friendly approach for the synthesis of imides using electrocatalytic oxidation with H2O as the oxygen source. The method eliminates the need for toxic or expensive oxidants and achieves high yields under mild reaction conditions. It shows broad substrate compatibility and potential for industrial applications.

GREEN CHEMISTRY (2024)

Article Chemistry, Multidisciplinary

Visible light-driven highly atom-economical divergent synthesis of substituted fluorenols and cyclopropylcarbaldehydes

Babasaheb Sopan Gore, Lin-Wei Pan, Jun-Hao Lin, Yi-Chi Luo, Jeh-Jeng Wang

Summary: Here, we report a visible light-promoted intramolecular radical cascade reaction for the construction of fluorenol and naphthalene-fused cyclopropyl carbaldehyde derivatives. This method offers mild reaction conditions, a broad substrate scope, excellent step efficiency, and scalability, without the need for external chemical oxidants. The novelty of this protocol was demonstrated by synthesizing chrysene analogs and performing late-stage functionalizations.

GREEN CHEMISTRY (2024)

Article Chemistry, Multidisciplinary

Supramolecular interaction-driven delignification of lignocellulose

Juho Antti Sirvio, Idamaria Romakkaniemi, Juha Ahola, Svitlana Filonenko, Juha P. Heiskanen, Ari Ammala

Summary: This article discusses the method of using supramolecular interaction between an aromatic hydrogen bond donor and lignin to achieve rapid delignification of softwood at low temperatures.

GREEN CHEMISTRY (2024)

Article Chemistry, Multidisciplinary

Photocatalytic synthesis of 2,3-diamines from anilines and DIPEA via C-N bond cleavage and C-C bond formation

Yunyan Meng, Chunxiang Pan, Na Liu, Hongjiang Li, Zixiu Liu, Yao Deng, Zixiang Wei, Jianbin Xu, Baomin Fan

Summary: A novel visible light-driven synthesis method for 2,3-diamines has been developed, which has mild conditions, avoids the use of metal reagents, and can synthesize diamines and diols in one pot.

GREEN CHEMISTRY (2024)

Article Chemistry, Multidisciplinary

Direct air-induced arylphosphinoyl radicals for the synthesis of benzo[b]phosphole oxides

Mingqing Huang, Haiyang Huang, Mengyao You, Xinxin Zhang, Longgen Sun, Chao Chen, Zhichao Mei, Ruchun Yang, Qiang Xiao

Summary: A direct air-oxidized strategy for the synthesis of benzo[b]phosphole oxides was developed in this study. Arylphosphine oxides were transformed into phosphinoyl radicals, which were further combined with various alkynes to achieve the desired products. DFT calculations revealed the mechanism of phosphinoyl radical formation.

GREEN CHEMISTRY (2024)

Article Chemistry, Multidisciplinary

A simple and convenient strategy for the oxidation of C(sp3)-H bonds based on γ-valerolactone

Anwei Wang, Jiayin Huang, Chunsheng Zhao, Yu Fan, Junfeng Qian, Qun Chen, Mingyang He, Weiyou Zhou

Summary: This study demonstrates an innovative strategy for the aerobic oxidation of C(sp(3))-H bonds using gamma-valerolactone. By optimizing the reaction conditions and utilizing specific catalysts, efficient oxidation of C(sp(3))-H bonds is achieved with good chemoselectivity in certain cases.

GREEN CHEMISTRY (2024)

Article Chemistry, Multidisciplinary

A novel high-entropy sulfide (ZnCoMnFeAlMg)9S8 as a low potential and long life electrocatalyst for overall water splitting in experiments and DFT analysis

Shun Li, Likai Tong, Zhijian Peng, Bo Zhang, Xiuli Fu

Summary: Sulfide compounds show promise as electrocatalysts for water splitting, but their performance is limited by factors such as limited active sites and hindered substance transport. This study successfully prepared a high-entropy sulfide (ZnCoMnFeAlMg)(9)S-8, which reduced grain size and increased specific surface area, enabling the realization of a dual-functional catalyst with multiple catalytic sites. High entropy also modulated the electronic properties of sulfides, reducing the potential energy barrier for hydrolysis. This research introduces a new approach for functionalizing high entropy nanomaterials and improves the performance of water splitting catalysts.

GREEN CHEMISTRY (2024)