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- In Vitro Study of the Bioavailability and Bioaccessibility of the Main Compounds Present in Ayahuasca BeveragesPublication . Gonçalves, Joana; Castilho, Miguel; Rosado, Tiago; Luís, Ângelo; Restolho, José; Fernández, Nicolás; Gallardo, Eugenia; Duarte, Ana PaulaAyahuasca is a psychoactive beverage that contains the psychoactive compound N,N-dimethyltryptamine and β-carboline alkaloids. This study aims at determining in vitro the bioavailability and bioaccessibility of the main compounds present in decoctions of four individual plants, in a commercial mixture and in four mixtures of two individual plants used in the preparation of Ayahuasca. The samples were subjected to an in vitro digestion process, and the Caco-2 cell line was used as an absorption model. The integrity and permeability of the cell monolayer were evaluated, as well as the cytotoxicity of the extracts. After digestion and cell incubation, the compounds absorbed by the cell monolayer were quantified by high-performance liquid chromatography coupled to a diode array detector. The results showed that compounds such as N,N-dimethyltryptamine, Harmine, Harmaline, Harmol, Harmalol and Tetrahydroharmine were released from the matrix during the in vitro digestion process, becoming bioaccessible. Similarly, some of these compounds, after being incubated with the cell monolayer, were absorbed, becoming bioavailable. The extracts did not show cytotoxicity after cell incubation, and the integrity and permeability of the cell monolayer were not compromised.
- Novel synthetic opioids - toxicological aspects and analysisPublication . Tabarra, Inês Pires; Soares, Sofia; Rosado, Tiago; Gonçalves, Joana; Luís, Ângelo; Malaca, Sara; Barroso, Mário; Keller, Thomas; Restolho, José; Gallardo, EugeniaOver the past few years, there has been an emerging number of new psychoactive drugs. These drugs are frequently mentioned as "legal highs", "herbal highs", "bath salts" and "research chemicals". They are mostly sold and advertised on online forums and on the dark web. The emerging new psychoactive substances are designed to mimic the effects of psychoactive groups, which are often abused drugs. Novel synthetic opioids are a new trend in this context and represent an alarming threat to public health. Given the wide number of fatalities related to these compounds reported within the last few years, it is an important task to accurately identify these compounds in biologic matrices in order to administer an effective treatment and reverse the respiratory depression caused by opioid related substances. Clinicians dealing with fentanyl intoxication cases should consider that it could, in fact, be a fentanyl analogue. For this reason, it is a helpful recommendation to include synthetic opioids in the routine toxicological screening procedures, including analysis in alternative matrices, if available, to investigate poly-drug use and possible tolerance to opioids. To address this public health problem, better international collaboration, effective legislation, effective investigation, control of suspicious "research chemicals" online forums and continuous community alertness are required. This article aims to review diverse reported fatalities associated with new synthetic opioids describing them in terms of pharmacology, metabolism, posology, available forms, as well as their toxic effects, highlighting the sample procedures and analytical techniques available for their detection and quantification in biological matrices.
- Comparative study of sample preparation procedures to determine the main compounds in ayahuasca beverages by QuEChERS and high‐performance liquid chromatography analysisPublication . Gonçalves, Joana; Rosado, Tiago; Barroso, Mário; Restolho, José; Fernández, Nicolás; Luís, Ângelo; Gallardo, Eugenia; Duarte, Ana PaulaIntroduction Ayahuasca is a psychoactive drink originally consumed by indigenous people of the Amazon. The lack of regulation of this drink leads to uncontrolled consumption, and it is often consumed in religious contexts. Objective The aim of this work is to compare three miniaturised extraction techniques for extracting the main ayahuasca compounds from beverages. Methodology Three sample pretreatment techniques were evaluated (dispersive liquid–liquid microextraction [DLLME], microextraction by packed sorbent [MEPS] and QuEChERS [Quick, Easy, Cheap, Effective, Rugged and Safe]) for the simultaneous extraction of N,N-dimethyltryptamine (DMT), tetrahydroharmine (THH), harmine, harmaline, harmol and harmalol from ayahuasca beverage samples. Then, the most promising technique (QuEChERS) was chosen to pre-concentrate the analytes, subsequently detected by high-performance liquid chromatography coupled to a diode array detector (HPLC-DAD). Results The procedure was optimised, with the final conditions being 500 μL of extractor solvent, 85 mg of primary secondary amine (PSA) and 4 s of vortexing. The analytical method was validated, showing to be linear between 0.16 and 10 μg/mL for β-carbolines and between 0.016 and 1 μg/mL for DMT, with coefficients of determination (R2) between 0.9968 and 0.9993. The limit of detection (LOD) and lower limit of quantification (LLOQ) were 0.16 μg/mL for all compounds, except for DMT (0.016 μg/mL) and extraction efficiencies varied between 60.2% and 88.0%. Conclusion The analytical methodology proved to be accurate and precise, with good linearity, LODs and LLOQs. This method has been fully validated and successfully applied to ayahuasca beverage samples.
- Ayahuasca Beverages: Phytochemical Analysis and Biological PropertiesPublication . Gonçalves, Joana; Luís, Ângelo; Gradillas, Ana; García, Antonia; Restolho, José; Fernández, Nicolás; Domingues, F.C.; Gallardo, Eugenia; Duarte, Ana PaulaAyahuasca is a psychoactive beverage, originally consumed by indigenous Amazon tribes, of which consumption has been increasing worldwide. The aim of this study was to evaluate the phytochemical profile, as well as the antioxidant, anti-inflammatory and antimicrobial properties of decoctions of four individual plants, a commercial mixture and four mixtures of two individual plants used in the Ayahuasca preparation. For this purpose, a phytochemical characterization was performed, determining the content of flavonoids, total phenolic compounds, and analyzing the phenolic profile. Besides, 48 secondary metabolites were investigated by ultra-high performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UHPLC-Q/TOF-MS) and their concentration estimated with real standards when present. The antioxidant activity was evaluated by both the β-carotene bleaching test and DPPH free radical scavenging assay, and the anti-inflammatory activity was determined by a protein denaturation method. Finally, the antimicrobial properties were evaluated using the disc diffusion assay, resazurin microtiter method, anti-quorum sensing and anti-biofilm activity assays. The obtained results showed that, in general, the samples have a high content of phenolic compounds and flavonoids with noticeable differences, reflecting on remarkable antioxidant and anti-inflammatory activities. Significant antimicrobial properties were also observed, with emphasis on the effect of B. caapi and P. harmala on planktonic and biofilm cells of A. baumannii, inhibiting both the biofilm formation and the production of violacein pigment.