IMPORTANT HUMAN METABOLITES OF PHENOLIC ACIDS FROM DIET WITH WILD EDIBLE MUSHROOMS: CHEMICAL SYNTHESIS AND STUDIES OF THEIR ANTIOXIDANT AND ANTITUMOR PROPERTIES

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Avaliação da bioatividade do corpo frutífero e esporos de Ganoderma lucidum

Publication . Heleno, Sandrina A.; Tavares, Catarina; Vaz, Josiana A.; Almeida, Gabriela M.; Vasconcelos, M. Helena; Martins, Anabela; Queiroz, Maria João R.P.; Ferreira, Isabel C.F.R.

Ganoderma lucidum é uma das espécies de cogumelos mais estudadas do mundo devido às suas propriedades medicinais. Este trabalho descreve a avaliação da capacidade antioxidante in vitro e antiproliferativa em células tumorais do extrato obtido a partir de diferentes partes do cogumelo. A atividade antioxidante dos extratos metanólicos, obtidos a partir das duas amostras, foi avaliada através da captação de radicais livres, poder redutor e inibição da peroxidação lipídica pela descoloração do β-caroteno e em homogeneizados de células cerebrais animais. A atividade antiproliferativa dos mesmos extratos foi avaliada em quatro linhas celulares tumorais humanas (pulmão- NCI-H460, mama- MCF-7, cólon- HCT-15 e estômago- AGS) pelo método da sulforrodamina B. Os extratos foram caracterizados por HPLC-DAD-MS.

2012Conference object

Open access

Bioacessibility studies related to antioxidant phenolic extracts from two edible species of the genus Hericium

Publication . Heleno, Sandrina A.; Barros, Lillian; Martins, Anabela; Queiroz, Maria João R.P.; Morales, Patricia; Fernández-Ruiz, Virginia; Ferreira, Isabel C.F.R.

Mushrooms are rich sources of nutrients, but also of bioactive molecules such as phenolic compounds. Phenolic acids are among the major low molecular weight bioactive components usually found in mushroom species, contributing to their antioxidant properties [1]. Following the ingestion, these molecules have to be released from the food matrix and further transformed by the organism, to became accessible and exert their bioactive properties [2]. Several in vitro methodologies have been developed in arder to evaluate the bioacessibility of bioactive compounds, proving to be easy, cheap and reproducible, being possible to evaluate the digestivo stability of the food constituents [3]. Herein, two wild edible mushroom species originated from Northeast Portugal (Herícium erinaceus (Buli.) Persoon and Hericium coralloides (Scop.) Pers.), were analysed for their nutritional value, detailed chemical composition and antioxidant properties. Furthermore, in arder to evaluate the bioaccessibiljty of the compounds responsible for the mushrooms antioxidant properties, a digestion of the dry powder and phenolic extracts was performed under in vitro conditions. The Hericium species showed similar chemical profiles (except for tocopherols), varying only in the concentration of these compounds. The phenolic extracts presented the highest antioxidant activity that is in agreement with the highest concentration in phenolic acids found in those samples before in vitro digestion. This means that after in vitro gastrointestinal digestion, the bioactive compounds can suffer structural changes (losing the OH groups responsible for the antioxidant activity) that decreased the antioxidant properties. Nevertheless, they are bioaccessible and still display antioxidant activity.

2015Conference object

Open access

Coprinopsis atramentaria extract, its organic acids, and synthesized glucuronated and methylated derivatives as antibacterial and antifungal agents

Publication . Heleno, Sandrina A.; Ferreira, Isabel C.F.R.; Ćirić, Ana; Glamočlija, Jasmina; Martins, Anabela; Queiroz, Maria João R.P.; Soković, Marina

Despite the available data regarding antimicrobial activity of phenolic acids, studies dealing with the effects of their metabolites or derivatives are scarce. Therefore, the antimicrobial and demelanizing activities of Coprinopsis atramentaria extract, its organic acids, and methylated and glucuronated derivatives were evaluated. The antifungal activity was stronger than the antibacterial effects. In general, individual compounds (mostly organic acids) gave higher activity than the extract and even higher than the standards used in the assays. Methylated derivatives presented the highest demelanizing activity toward Aspergillus niger, A. fumigatus and Penicillium verrucosum var. cyclopium). The inclusion of methyl groups in the parental compound (CoAM1, CoAM2 and CoAM3) strongly increased antibacterial and antifungal activities of CoA, while the inclusion of acetyl groups (CoAGP) increased the antifungal activity but the antibacterial properties were maintained. For HA and CA, the inclusion of methyl groups (HAM1, HAM2, HAM3 and CAM) increased the demelanizing activity, but decreased the antimicrobial properties. The present work contributes to the knowledge of the mechanisms involved in the antimicrobial properties of organic acids namely, phenolic acids, usually present in mushrooms. Organic acids, methylated and glucuronated derivatives could be used as antimicrobial agents.

2014Journal article

Open access

Antimicrobial activity of Ganoderma lucidum extract, p-hydroxybenzoic and cinnamic acids and their synthetic acetylated glucuronide methyl esters

Publication . Heleno, Sandrina A.; Ferreira, Isabel C.F.R.; Esteves, Ana P.; Ćirić, Ana; Glamočlija, Jasmina; Martins, Anabela; Soković, Marina; Queiroz, Maria João R.P.

Ganoderma lucidumis one of the most famous traditional medicinal mushrooms, being used as functional food and in preventive medicines [1 ]. p-Hydroxybenzoic and cinnamic acids were previously identified, by our research group, in wild G. lucidum from Northeast of Portugal [2].Many studies suggest that phenolic compounds are rapidly metabolized in the human organism being glucuronidation the most prevalent metabolic pathway for phenolic compounds in humans. Despite the large data concerning the antimicrobial effects of phenolic acids [3], studies dealing with the antimicrobial properties of their metabolites or derivatives are scarce due to the fact that most of these compounds are not commercially available. Herein we describe the synthesis of protected (acetylated) glucuronide derivatives of p-hydroxybenzoic and cinnamic acids. Their antimicrobial activity was evaluated and compared to the parent acids and G. lucidum extract.p-Hydroxybenzoic and cinnamic acids, as also their protected glucuronide derivatives revealed high antimicrobial (antibacterial and antifungal) activity, even better than the one showed by commercial standards. Despite the variation in the order of parent acids and the protected glucuronide derivatives, their antimicrobial activity was always higher than the one revealed by the extract. The synthesized acetylated glucuronide derivatives could be deprotected to obtain glucuronide metabolites, which circulate in the human organism as products of the metabolism of the parent compounds.

2013Conference object

Open access

Composição química, atividade antioxidante e estudos de biodisponibilidade em extratos fenólicos de dois cogumelos silvestres do género Hericium

Publication . Heleno, Sandrina A.; Barros, Lillian; Martins, Anabela; Queiroz, Maria João R.P.; Morales, Patricia; Fernández-Ruiz, Virginia; Ferreira, Isabel C.F.R.

Além de serem importantes fontes de nutrientes, os cogumelos são também uma fonte rica em moléculas bioativas como os ácidos fen6licos, que contribuem para a sua bioatividade [1]. Quando ingeridas, estas moléculas tem de se libertar da matriz alimentar para que possam ser transformadas e absorvidas pelo organismo, de modo a poderem exercer as suas atividades biológicas [2]. Varias metodologias in vitro tem sido desenvolvidas para avaliação da biodisponibilidade destas moléculas [3]. No presente trabalho, duas espécies de cogumelos do género Hericium foram analisadas relativamente a sua composição química e atividade antioxidante. Para além disso, realizou-se uma digestão in vitro dos cogumelos liofilizados e dos seus extratos fen61icos; as amostras dialisadas foram também submetidas a ensaios de avalia<;:ao da atividade antioxidante a fim de avaliar a biodisponibilidade dos compostos responsáveis pela bioatividade. Hericium erinaceus (Bull.) Persoon e H. coraloides (Scop.) Pers., revelaram perfis semelhantes em termos de composição química (excetuando os tocoferois), apresentando apenas variações na concentração dos compostos. Os extratos fenólicos revelaram maior potencial antioxidante (atividade antioxidante e compostos antioxidantes, tais como os ácidos fenólicos) do que as amostras obtidas após digestão in vitro, significando que este processo pode diminuir o potencial antioxidante do extrato/cogumelo. No entanto, embora exibindo uma bioatividade mais fraca, os compostos bioativos continuaram biodisponíveis, uma vez que os ácidos fenólicos foram identificados nas amostras dialisadas.

2014Conference object

Open access