A green approach for genistein and apigenin extraction optimization from by-products of soybean crops

Soybeans’ genistein and its isomer apigenin are widely studied bioactive compounds owing to their therapeutic potential for treating various health disfunctions. A green extraction of both from soy by-products could lead to a valuable and sustainable approach to adding value to these materials in a biorefinery context. Here Hansen Solubility Parameters (HSP) and the Conductor-like Screening MOdel for Real Solvents (COSMO-RS) were applied to screen green molecular solvents and Natural Eutectic Solvents for the extraction of genistein and apigenin from soy by-products. The predicted solubilities of genistein and apigenin in 18 shortlisted candidates were experimentally tested by dynamic maceration, the most industrially implemented natural products extraction technique. EtOH:H2O (8:2, v/v) and natural eutectic solvent (NAES) betaine:ethylene glycol (1:2, mol/mol) showed the highest performance. These were selected for extraction optimizations by Design of Experiments from soy branches, the largest by-product by mass. The optimum condition of each solvent was applied to extract all other parts of soy collected post-mechanical harvesting. The highest value of apigenin, 591.49±26.7 µg/g, was achieved from soy pods with EtOH:H2O (8:2, v/v), while the highest of genistein, 54.04±3.39 µg/g, was achieved from soybeans using the same solvent. Our findings highlight the necessity of exercising caution when interpreting in silico outcomes in the context of metabolite extractions from complex matrices. A trade-off between in silico solvent screening and experimental work should be followed when developing new phytochemical extraction processes. Furthermore, soy by-products emerged as competitive candidates for a long-term source of the bioactive apigenin in a biorefinery context

Analysis of propolis from Serra do Japi, determination of its botanical source and its effects on mouse fibroblasts

Atualmente, há uma considerável quantidade de informações relativas a aspectos químicos e biológicos da própolis, porém sua aplicação terapêutica ainda pode ser considerada incipiente. Isto se deve, principalmente, a grande variabilidade da composição química deste produto em função de sua origem geográfica/botânica, já que em diferentes ecossistemas as abelhas recorrem a distintas espécies vegetais como fontes de matérias-primas para sua elaboração. Desta forma, para se chegar a uma futura padronização, os conhecimentos da(s) fonte(s) botânica(s) e da origem geográfica da amostra são fundamentais e devem acompanhar qualquer estudo biológico, no sentido de se estabelecer quais atividades biológicas correspondem a um tipo específico de própolis. O presente trabalho objetiva contribuir para os conhecimentos da composição de própolis do estado de São Paulo (coletado na Serra do Japi) e de sua fonte botânica, bem como para a discussão dos possíveis mecanismos envolvidos em processos de cicatrização, influenciados pela aplicação tópica de própolis (um de seus usos mais difundidos mundialmente é como \"cicatrizante\"). Para tanto, traz análises físico-químicas, preconizadas pelo Ministério da Agricultura (teores de cinzas, cera, sólidos solúveis, flavonóides e fenóis totais, perda por dessecação a 105 ºC e massa mecânica), estudos de composição química pela técnica CLAE, análises cromatográficas comparativas entre o extrato metanólico de própolis e de sua suposta fonte botânica, quantifica a complexação de substâncias fenólicas da própolis ao pó de pele e traz estudos, in vitro, da influência deste produto sobre proliferação de fibroblastos de camundongos (células NIH 3T3). Excetuando-se a perda por dessecação a 105 ºC, todos os demais parâmetros estiveram dentro dos limites estabelecidos pelo Ministério da Agricultura, para a fixação de identidade e qualidade da própolis. Identifica os flavonóides canferol, canferida e isossacuranetina e os ácidos para-cumárico, ferúlico, clorogênico, cafeico, trans-cinâmico e Artepillin C, na própolis, e comprova ser a Baccharis dracunculifolia DC. (vassourinha) a sua fonte botânica. Mostra que a própolis foi tóxica aos fibroblastos nas concentrações de 125,00; 62,50 e 31,25 µg/mL e levemente proliferativa entre as concentrações 7,812 e 0,732 µg/mL, mas sem diferenças estatisticamente significativas em relação a seus controles. Indica que 68,12% das substâncias fenólicas presentes no extrato etanólico de própolis complexaram com pó de pele. Conclui, dentre outras coisas, que a própolis estudada apresenta grande variedade de substâncias fenólicas, adsorve fortemente a pele humana, não possui efeito proliferativo estatisticamente significativo sobre os fibroblastos de camundongo (células NIH 3T3) e, provavelmente, atua auxiliando o processo de cicatrização indiretamente, facilitando o estabelecimento das condições ideais para que a cicatrização ocorra.Nowadays a great amount of information relating chemical and biological aspects of propolis is available in the literature, but only a few data on its therapeutic uses are found. The major reason of this fact is due to the enormous variability of chemical composition of propolis regarding the geographiclbotanic source of the material, because bees prepare propolis using different vegetable species as raw materiais from different e cosystems in the environment. In order to increase the therapeutic use of propolis, it is important to establish which biological activity corresponds to a specific type of propolis (regarding its origin and chemical composition). Therefore, the botanical and geographic origin of propolis knowledge should follow any biological investigations with this material. This paper offers a contribution to the chemical composition knowledge of propolis from São Paulo state (Serra do Japi - Brazil) and its botanical vegetable source, as well as the discussion of possible mechanisms involved in wound healing process related to this material. For this reason, presents commended Ministry of Agricultural analysis (loss on drying at 105 ºC, determinations of extractable and non-extractable matter and determinations of ash, wax, flavonoids and total phenolic contents), chemical composition studies by HPLC, comparative chromatographic analysis between propolis and its expected vegetal source, adsorption determination of phenolic substances in skin powder and fibroblast proliferation assay (NIH 3T3 cells). Excepting the drying loss test at 105 ºC, all the parameters have been according the limits established by the Ministry of Agricultural to guarantee the identity and quality of propolis. Identification of kaempferol, kaempferide, isosakuranetin, Artepillin C, p-coumaric acid, ferulic acid, chlorogenic acid, caffeic acid and t-cinnamic acid in propolis was possible. The specie Baccharis dracunculifolia DC was identified as the vegetable source of the propolis. About 68% of phenolic substances present in the original extract adsorbed to the skin powder. Propolis was toxic to the fibroblasts at 125,0, 62,5, and 31,25 µg/mL and slightly proliferative between concentrations of 7,812 and 0,732 µg/mL but with no significant statistic differences relating the controls. It is conclusive that the propolis under study presents a great variety of phenolic substances, adheres strongly to the human skin, presents no proliferative effect to the mouse fibroblasts (NIH 3T3 cells) and probably helps to esta blish good conditions to the wound healing process

Analysis of propolis from Serra do Japi, determination of its botanical source and its effects on mouse fibroblasts

Atualmente, há uma considerável quantidade de informações relativas a aspectos químicos e biológicos da própolis, porém sua aplicação terapêutica ainda pode ser considerada incipiente. Isto se deve, principalmente, a grande variabilidade da composição química deste produto em função de sua origem geográfica/botânica, já que em diferentes ecossistemas as abelhas recorrem a distintas espécies vegetais como fontes de matérias-primas para sua elaboração. Desta forma, para se chegar a uma futura padronização, os conhecimentos da(s) fonte(s) botânica(s) e da origem geográfica da amostra são fundamentais e devem acompanhar qualquer estudo biológico, no sentido de se estabelecer quais atividades biológicas correspondem a um tipo específico de própolis. O presente trabalho objetiva contribuir para os conhecimentos da composição de própolis do estado de São Paulo (coletado na Serra do Japi) e de sua fonte botânica, bem como para a discussão dos possíveis mecanismos envolvidos em processos de cicatrização, influenciados pela aplicação tópica de própolis (um de seus usos mais difundidos mundialmente é como \"cicatrizante\"). Para tanto, traz análises físico-químicas, preconizadas pelo Ministério da Agricultura (teores de cinzas, cera, sólidos solúveis, flavonóides e fenóis totais, perda por dessecação a 105 ºC e massa mecânica), estudos de composição química pela técnica CLAE, análises cromatográficas comparativas entre o extrato metanólico de própolis e de sua suposta fonte botânica, quantifica a complexação de substâncias fenólicas da própolis ao pó de pele e traz estudos, in vitro, da influência deste produto sobre proliferação de fibroblastos de camundongos (células NIH 3T3). Excetuando-se a perda por dessecação a 105 ºC, todos os demais parâmetros estiveram dentro dos limites estabelecidos pelo Ministério da Agricultura, para a fixação de identidade e qualidade da própolis. Identifica os flavonóides canferol, canferida e isossacuranetina e os ácidos para-cumárico, ferúlico, clorogênico, cafeico, trans-cinâmico e Artepillin C, na própolis, e comprova ser a Baccharis dracunculifolia DC. (vassourinha) a sua fonte botânica. Mostra que a própolis foi tóxica aos fibroblastos nas concentrações de 125,00; 62,50 e 31,25 µg/mL e levemente proliferativa entre as concentrações 7,812 e 0,732 µg/mL, mas sem diferenças estatisticamente significativas em relação a seus controles. Indica que 68,12% das substâncias fenólicas presentes no extrato etanólico de própolis complexaram com pó de pele. Conclui, dentre outras coisas, que a própolis estudada apresenta grande variedade de substâncias fenólicas, adsorve fortemente a pele humana, não possui efeito proliferativo estatisticamente significativo sobre os fibroblastos de camundongo (células NIH 3T3) e, provavelmente, atua auxiliando o processo de cicatrização indiretamente, facilitando o estabelecimento das condições ideais para que a cicatrização ocorra.Nowadays a great amount of information relating chemical and biological aspects of propolis is available in the literature, but only a few data on its therapeutic uses are found. The major reason of this fact is due to the enormous variability of chemical composition of propolis regarding the geographiclbotanic source of the material, because bees prepare propolis using different vegetable species as raw materiais from different e cosystems in the environment. In order to increase the therapeutic use of propolis, it is important to establish which biological activity corresponds to a specific type of propolis (regarding its origin and chemical composition). Therefore, the botanical and geographic origin of propolis knowledge should follow any biological investigations with this material. This paper offers a contribution to the chemical composition knowledge of propolis from São Paulo state (Serra do Japi - Brazil) and its botanical vegetable source, as well as the discussion of possible mechanisms involved in wound healing process related to this material. For this reason, presents commended Ministry of Agricultural analysis (loss on drying at 105 ºC, determinations of extractable and non-extractable matter and determinations of ash, wax, flavonoids and total phenolic contents), chemical composition studies by HPLC, comparative chromatographic analysis between propolis and its expected vegetal source, adsorption determination of phenolic substances in skin powder and fibroblast proliferation assay (NIH 3T3 cells). Excepting the drying loss test at 105 ºC, all the parameters have been according the limits established by the Ministry of Agricultural to guarantee the identity and quality of propolis. Identification of kaempferol, kaempferide, isosakuranetin, Artepillin C, p-coumaric acid, ferulic acid, chlorogenic acid, caffeic acid and t-cinnamic acid in propolis was possible. The specie Baccharis dracunculifolia DC was identified as the vegetable source of the propolis. About 68% of phenolic substances present in the original extract adsorbed to the skin powder. Propolis was toxic to the fibroblasts at 125,0, 62,5, and 31,25 µg/mL and slightly proliferative between concentrations of 7,812 and 0,732 µg/mL but with no significant statistic differences relating the controls. It is conclusive that the propolis under study presents a great variety of phenolic substances, adheres strongly to the human skin, presents no proliferative effect to the mouse fibroblasts (NIH 3T3 cells) and probably helps to esta blish good conditions to the wound healing process

Estudos químicos e biológicos de espécies do gênero Lippia (Verbenaceae) nativas no Cerrado paulista

A criação de um modelo nacional de saúde pautado nas aptidões e carências brasileiras é tida como fundamental para tornar o acesso à saúde pública mais abrangente e de melhor qualidade. O histórico do desenvolvimento mundial de medicamentos, a biodiversidade e os conhecimentos tradicionais associados a esta, e as competências científicas existentes no Brasil evidenciam a importância da bioprospecção. O gênero Lippia é amplamente empregado em etnomedicina e é constituído principalmente por espécies aromáticas. As investigações químicas e farmacológicas estão majoritariamente concentradas nos seus óleos essenciais, mas alguns componentes fixos, como flavonóides, fenilpropanóides, naftoquinóides e iridóides glicosilados já foram relatados. O Brasil abriga a maioria das espécies deste gênero, mas diversos problemas taxonômicos dificultam o estabelecimento de dados precisos. O stress oxidativo é apontado como ponto central no desenvolvimento de processos degenerativos associados ao envelhecimento e a diversas doenças. Conseqüentemente, terapias antioxidantes estão sendo propostas para o seu tratamento ou prevenção. Este trabalho descreve o fracionamento de extratos de folhas e de ramos de L. salviaefolia guiado por testes antioxidantes que levou ao isolamento de 16 substâncias fenólicas, sendo 4 isômeros interconversíveis inéditos, 2S e 2R-3',4',5,6-tetraidroxi-7-O-β-glicopiranosil-flavanona (12a e 12b) e 2S e 2R-5,8,3',4'-tetraidroxi-7-O-β-glicopiranosil-flavanona (13a e 13b), que foram identificadas em mistura por estudos extensivos de Ressonância Magnética Nuclear e Espectrometria de Massas. Foram isoladas também 8 substâncias do extrato de raízes de L. lupulina, selecionado com base em estudos iniciais de desreplicação por Cromatografia Líquida de Alta Eficiência acoplada a Arranjo de Fotodiodos (CLAE-DAD). Os extratos...The creation of a national model of health guided by need and capacity in Brazil is seen as fundamental to making access to public health more comprehensive and of better quality. The historical development of world medicine, the biodiversity and traditional knowledge associated with this, and the scientific expertise available in Brazil highlight the significance of bioprospecting in this country. The genus Lippia is widely used in ethnomedicine. Since most of its species are aromatic, the studies on the chemistry and pharmacology of this genus are mainly focused in essential oils, but some fix compounds, such as flavonoids, phenylpropanoids, naphthoquinoids and iridoids glucosides have also been reported. It is estimated that Brazil hosts most of Lippia species, but several taxonomical problems related to this species hamper the establishment of accurate data difficult. Oxidative stress has a central role in the development of degenerative processes associated to aging and several diseases, including cancer and inflammation. Consequently, antioxidant therapies are being proposed for their treatment or prevention. This work describes the fractionation procedures of L. salviaefolia leaves and stems extracts guided by simple antioxidant assays which led to 16 phenolic compounds, including 4 novel interconverting isomers (2S) and (2R)-3',4',5,6-tetrahydroxyflavanone-7-O-β-glucopyranoside (12a and 12b) and (2S) and (2R)-3',4',5,8-tetrahydroxyflavanone-7-O-β-glucopyranoside (13a and 13b), which were identified in mixture by extensive use of 1D and 2D NMR and MS techniques. Additionaly, other 8 compounds were isolated from the extract of roots of L. lupulina, which led to its selection for dereplication studies by High Pressure Liquid Chromatography-Photodiode Array Detector (HPLC-DAD). The bioactivity evaluation of extracts and isolated compounds from L. salviaefolia was initiated... (Complete abstract click electronic access below)Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP

Metabolomics as a tool to study underused soy parts: In search of bioactive compounds

This article belongs to the Special Issue Recent Trends and Applications of Metabolomics in Food Analysis, Authentication and Process Monitoring.The valorization of agri-food by-products is essential from both economic and sustainability perspectives. The large quantity of such materials causes problems for the environment; however, they can also generate new valuable ingredients and products which promote beneficial effects on human health. It is estimated that soybean production, the major oilseed crop worldwide, will leave about 597 million metric tons of branches, leaves, pods, and roots on the ground post-harvesting in 2020/21. An alternative for the use of soy-related by-products arises from the several bioactive compounds found in this plant. Metabolomics studies have already identified isoflavonoids, saponins, and organic and fatty acids, among other metabolites, in all soy organs. The present review aims to show the application of metabolomics for identifying high-added-value compounds in underused parts of the soy plant, listing the main bioactive metabolites identified up to now, as well as the factors affecting their production.This research was funded by São Paulo Research Foundation—FAPESP, grant number 2020/09500-0, 2018/21128-9 and 2017/06216-6, and the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior—Brasil (CAPES)—Finance Code 001.Peer reviewe

Natural deep eutectic solvents for the green extraction of soy by-products

Resumen del trabajo presentado al 2nd International Meeting on Deep Eutectic Systems, celebrado online del 15 al 17 de junio de 2021.Peer reviewe

Production and Synthetic Possibilities of 5-Chloromethylfurfural as Alternative Biobased Furan

As fossil-based resource depletion intensifies and the use of lignocellulosic biomass gains more and more momentum for the development of biorefineries, the production of furans has received a great deal of attention considering their outstanding synthetic possibilities. The production of 5-hydroxymethylfurfural (HMF) is quite established in the recent scientific literature, with a large number of studies having been published in the last few years. Lately, there has been a growing interest in the synthesis of 5-chloromethylfurfural (CMF) as a novel building block of similar molecular structure to that of HMF. CMF has some advantages, such as its production taking place at milder reaction conditions, a lower polarity that enables easier separation with the aid of organic media, and the presence of chlorine as a better leaving group in synthesis. Precisely the latter aspect has given rise to several interesting products to be obtained therefrom, including 2,5-dimethylfuran, 2,5-furandicarboxylic acid, and 5-methylfurfural, to name a few. This work covers the most relevant aspects related to the production of CMF and an array of synthetic possibilities. Through varied catalysts and reaction conditions, value-added products can be obtained from this chemical, thus highlighting the advances in the production and use of this chemical in recent years