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- Plant-Based Beverages: Consumption Habits, Perception and Knowledge on a Sample of Portuguese CitizensPublication . Anjos, Ofélia; Pires, Patrícia C. P.; Gonçalves, Joana; Estevinho, Maria Letícia; Mendonça, António José Geraldes de; Guiné, Raquel P. F.Plant-based beverages (PBB) consumption has increased significantly worldwide due to an interest in vegetarian/vegan diets, taste preferences, health and ethical and environmental issues. Therefore, this study intends to investigate consumption habits, consumer preferences and consumers’ level of knowledge about PBB. In this study, a voluntary, anonymous questionnaire survey was applied to a sample of participants from Portugal. The sample was recruited by convenience, and therefore, the distribution among the groups was not even. Data analysis involved different statistical techniques: basic statistics, chi-square tests, factor analysis, cluster analysis and tree classification analysis. The results indicated that the most consumed PBB were almond, soy and oat beverages. The majority of consumers chose these beverages for nutritional and health reasons, while a smaller number consumed them as part of a vegetarian or vegan diet. The main motivations for consuming PBB are mainly associated with sustainability and health benefits. The results regarding the respondents’ knowledge about PBB revealed that a health-related profession was the most significant predictor. These results allowed us to conclude that the factors of nutrition, health, ethics and practice of a vegetarian/vegan diet influence the consumption of PBB. It was also concluded that being in a healthcare profession, along with age and professional status within this field, were significant factors influencing the level of knowledge about PBB.
- Cannabis and Its Secondary Metabolites: Their Use as Therapeutic Drugs, Toxicological Aspects, and Analytical DeterminationPublication . Gonçalves, Joana; Rosado, Tiago; Soares, Sofia; Simão, Ana; Caramelo, Débora Almeida; Luís, Ângelo; Fernández, Nicolás; Barroso, Mário; Gallardo, Eugenia; Duarte, Ana PaulaAlthough the medicinal properties of Cannabis species have been known for centuries, the interest on its main active secondary metabolites as therapeutic alternatives for several pathologies has grown in recent years. This potential use has been a revolution worldwide concerning public health, production, use and sale of cannabis, and has led inclusively to legislation changes in some countries. The scientific advances and concerns of the scientific community have allowed a better understanding of cannabis derivatives as pharmacological options in several conditions, such as appetite stimulation, pain treatment, skin pathologies, anticonvulsant therapy, neurodegenerative diseases, and infectious diseases. However, there is some controversy regarding the legal and ethical implications of their use and routes of administration, also concerning the adverse health consequences and deaths attributed to marijuana consumption, and these represent some of the complexities associated with the use of these compounds as therapeutic drugs. This review comprehends the main secondary metabolites of Cannabis, approaching their therapeutic potential and applications, as well as their potential risks, in order to differentiate the consumption as recreational drugs. There will be also a focus on the analytical methodologies for their analysis, in order to aid health professionals and toxicologists in cases where these compounds are present.
- 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.
- Julbernardia paniculata and Pterocarpus angolensis: From Ethnobotanical Surveys to Phytochemical Characterization and Bioactivities EvaluationPublication . Santos, Eugénia Solange; Luís, Ângelo; Gonçalves, Joana; Rosado, Tiago; Pereira, L.; Gallardo, Eugenia; Duarte, A. P.Julbernardia paniculata and Pterocarpus angolensis are two plant species with important application in African traditional medicine, particularly in Angola, in the treatment of several diseases. However, scientific studies concerning these species are scarce. The goal of this work was to know better which medicinal approaches are used by the Huíla population in Angola by means of ethnobotanical surveys. Furthermore, extracts of both plants were phytochemically characterized. Antioxidant, anti-inflammatory, wound-healing activities, and potential cytotoxicity were also studied. With this study it was possible to verify that 67% of the individuals that use medicinal plants are women, and their main therapeutic uses are the treatment of problems of the digestive system and skin disorders. Barks of J. paniculata and leaves of P. angolensis are the most often used plant parts. Through high-performance liquid chromatography coupled to diode-array detector (HPLC-DAD) and GC-MS it was possible to characterize the chemical composition of the two species, which are rich in phenolic compounds, terpenes, terpenoids, sesquiterpenoids and fatty acids. Both plants showed to possess antioxidant, anti-inflammatory proprieties, and wound-healing activity. To the best of our knowledge, this is the most comprehensive study of these two species and the first ethnobotanical and ethnopharmacological study of medicinal plants from this region of Angola.
- Psychoactive Substances of Natural Origin: Toxicological Aspects, Therapeutic Properties and Analysis in Biological SamplesPublication . Gonçalves, Joana; Luís, Ângelo; Gallardo, Eugenia; Duarte, Ana PaulaThe consumption of new psychoactive substances (NPSs) has been increasing, and this problem affects several countries worldwide. There is a class of NPSs of natural origin, consisting of plants and fungi, which have a wide range of alkaloids, responsible for causing relaxing, stimulating or hallucinogenic effects. The consumption of some of these substances is prompted by religious beliefs and cultural reasons, making the legislation very variable or even ambiguous. However, the abusive consumption of these substances can present an enormous risk to the health of the individuals, since their metabolism and effects are not yet fully known. Additionally, NPSs are widely spread over the internet, and their appearance is very fast, which requires the development of sophisticated analytical methodologies, capable of detecting these compounds. Thus, the objective of this work is to review the toxicological aspects, traditional use/therapeutic potential and the analytical methods developed in biological matrices in twelve plant specimens (Areca catechu, Argyreia nervosa, Ayahuasca, Catha edulis, Datura stramonium, Lophophora williamsii, Mandragora officinarum, Mitragyna speciosa, Piper methysticum Forst, Psilocybe, Salvia divinorum and Tabernanthe iboga).
- Assessment of the Bioaccessibility and Bioavailability of the Phenolic Compounds of Prunus avium L. by in Vitro Digestion and Cell ModelPublication . Gonçalves, Joana; Ramos, Rodrigo; Luís, Ângelo; Rocha, Sandra; Rosado, Tiago; Gallardo, Eugenia; Duarte, Ana PaulaThe fruit of Prunus avium L., commonly known as sweet cherry, is an excellent source of phytochemicals, namely, phenolic compounds. This study aims to determine in vitro the bioavailability and the bioactivity of phenolic compounds present in cherries. Caco-2 cells were used, and the permeability and integrity of the monolayer formed were investigated. After incubation, the phenolic compounds that permeabilized the cell monolayer were quantified using a high-performance liquid chromatography–diode array detector, and the antioxidant activity was evaluated by the 1,1-diphenyl-2-picrylhydrazyl method. The results demonstrated that the phenolic compounds of sweet cherries after undergoing a simulated digestion were absorbed by the cellular barrier, becoming bioavailable. Contrary to what was found after incubation with the in vitro digested extract, the integrity of the cell monolayer was altered and its permeability increased upon incubation with the sweet cherry phenolic extract. Regarding the antioxidant activity, it was verified that this decreased after the absorption by the cellular monolayer. This study suggests that digestion is an indispensable process for absorption because without it the phenolic content of the food matrix does not become bioaccessible.
- 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.
- Synthetic cannabinoids in biological specimens: a review of current analytical methods and sample preparation techniquesPublication . Rosado, Tiago; Gonçalves, Joana; Luís, Ângelo; Malaca, Sara; Soares, Sofia; Vieira, Duarte Nuno; Barroso, Mário; Gallardo, EugeniaSynthetic cannabinoids are a new class of chemical drugs capable of modifying human behavior. These products do not contain cannabis, but produce similar effects after consumption. The fact that they are easily accessed, and are many times considered to be harmless, justifies their widespread use among young people. This fact, together with the difficulty in their detection by routine drug tests, makes it extremely important to develop new procedures able to detect and monitor their consumption. The aim of this work is to perform a critical review regarding the human biological samples that can be used for the determination of synthetic cannabinoids, paying special attention to analytical methods and sample preparation techniques. The reviewed articles deal with the determination of synthetic cannabinoids in the context of forensic and toxicological analysis.
- Avaliação In Vitro dos Potenciais Efeitos Terapêuticos e Toxicológicos Associados ao Consumo de AyahuascaPublication . Gonçalves, Joana Domingos; Duarte, Ana Paula Coelho; Alba, Maria Eugénia Gallardo; Luís, Ângelo Filipe SantosAyahuasca is a psychoactive beverage that has been consumed for centuries and was originally used by indigenous tribes in the northwest of the Amazon. This beverage consists of a decoction, thick, oily, and brownish in color, which is originally prepared from the leaves of Psychotria viridis Ruiz & Pav. and the scrapings of the stem of Banisteriopsis caapi (Spruce ex Griseb.) C.V.Morton, although over the years several modifications of this decoction have been developed. Currently, some natural or synthetic adulterants that can mimic the effects of the plants originally used are known. This decoction contains the hallucinogenic compound N,N-dimethyltryptamine (DMT) from Psychotria viridis, and β-carboline alkaloids such as harmine, tetrahydroharmine (THH) and harmaline, which come from Banisteriopsis caapi. DMT is the main psychoactive component of ayahuasca, since it acts as a serotonin receptor (5-HT1A/2A/2C) agonist and, when ingested alone, is metabolized by peripheral monoamine oxidase A (MAO-A), making it if harmless. However, together with the β-carboline alkaloids, it can reach the circulation and the central nervous system, by temporarily inhibiting MAO-A. Additionally, THH also inhibits serotonin reuptake enhancing the effects of DMT. This synergy between compounds is known by the indigenous peoples for about 3000 years. Thus, originally, the tribes resorted to this beverage for therapeutic and religious purposes. It was also used by native healers to treat psychological disorders, stimulate visual creativity and creative thinking. More recently, non-indigenous religious entities in various countries, especially in Latin America, also used this beverage for their ceremonies, namely Barquinha, União do Vegetal and Santo Daime. These last two, currently spread to other continents. In recent decades, the popularity of ayahuasca has increased worldwide, being seen as a natural remedy used for millennia to cure various diseases. Thus, currently this beverage, despite continuing to be used in a traditional way, is also consumed recreationally all over the world, as well as used in modern medicine. When consuming ayahuasca, vomiting, diarrhea and nausea often occur. In addition to these physical symptoms, changes in body temperature, pupil size and immunological, endocrine, and cardiovascular changes were observed. Psychological symptoms such as changes in perception (time, space, and the senses) and at the cognitive level have been also described. Additionally, connections with divine and mythical entities are also described, which is the aspect that motivates its consumption in a religious context. Despite all the effects described, over the years several beneficial properties have been pointed out to ayahuasca, even believing in its therapeutic potential in psychological illnesses, such as depression, anxiety, addiction, and psychological disorders. Additionally, beneficial properties in physiological treatments are also pointed out. In recent decades, the consumption of psychoactive substances has been increasing, namely substances of natural origin, such as ayahuasca. This consumption is often incited by cultural motivations or by spiritual and religious beliefs, making it difficult to measure its worldwide use. According to the literature, the ayahuasca consumption of in controlled environments is not dangerous and is not associated with psychotic episodes. However, the expansion of its consumption has raised some concerns. Although the consumption of DMT source plants is not controlled, it has become a controlled substance in some countries, due to the increase in its demand. However, the legislation regulating psychoactive substances is very variable and may even be ambiguous. Considering the potential of ayahuasca, the first objective of this thesis was to develop an analytical methodology for determine and quantify the main compounds present in ayahuasca decoctions, as well as to understand their behavior throughout the digestive process. The second objective was to carry out a phytochemical characterization of ayahuasca decoctions and to evaluate their potential antioxidant, anti-inflammatory, antimicrobial effects and their therapeutic properties in wound healing and cancer treatment. Thus, initially decoctions, in sufficient quantity to carry out the entire study, of four individual plants commonly used in ayahuasca preparations (P. viridis (leaves), Mimosa hostilis Benth. (root), B. caapi (stem) and Peganum harmala L. (seeds)), a decoction of a commercial mixture and four decoctions of mixtures of two of the above plants (P. viridis and B. caapi, P. viridis and Peganum harmala, Mimosa hostilis and B. caapi and M. hostilis and P. harmala) were prepared. The samples were submitted to three microextraction procedures and later, an analytical method was developed and validated for the determination and quantification of the main compounds of these samples. The Quick, Easy, Cheap, Effective, Rugged and Safe (QuEChERS) technique proved to be the most promising and, therefore, was chosen for application in the samples. The analytical method showed to be linear between 0.16 and 10 μg/mL for β-carbolines and between 0.016 and 1 μg/mL for DMT, with determination coefficients (R2) between 0.9968 and 0.9993. The limit of detection (LOD) and lower limit of quantification (LLOQ) were 0.16 μg/mL (0.016 μg/mL for DMT) and extraction efficiencies ranged from 60 to 88%. The bioavailability and bioaccessibility of the same compounds were also evaluated in vitro. The bioaccessibility of the samples was assessed using an in vitro digestion process, and subsequently their bioavailability was evaluated using the colorectal adenocarcinoma cell line (Caco-2). After quantification, it was verified that the compounds (DMT, harmine, harmaline, harmol, harmalol and THH) were released from the matrix during the in vitro digestion process, becoming bioaccessible. Likewise, some of these compounds, after being incubated with the cell monolayer, were absorbed, becoming bioavailable, without presenting a risk to its integrity. The phytochemical profile of the samples was evaluated, and it was demonstrated that, in general, the samples have a high content of phenolic compounds and flavonoids. These results reflect the antioxidant and anti-inflammatory activities also determined. Additionally, the samples showed antimicrobial properties, with emphasis on the effect of B. caapi and P. harmala on the A. baumannii strain, which resulted in the inhibition of both biofilm formation and quorum sensing. Ayahuasca samples also demonstrated their therapeutic potential, particularly in terms of wound healing. Using normal human dermal fibroblasts (NHDF), a scratch assay was performed, and it was found that only one sample showed cytotoxicity and the others promoted the migration of skin fibroblasts, without cutaneous absorption of DMT and β-carboline alkaloids. Likewise, the ayahuasca samples showed a great anticancer potential in Caco-2 cells, having been verified that after incubation, the samples significantly induced apoptosis while cell proliferation decreased significantly. There was also a significant reduction in oxidative stress with some samples, with a significant increase in the activity of antioxidant enzymes. Similarly, in gastric adenocarcinoma (AGS) cells, an increase in the induction of apoptosis and a reduction in oxidative stress were observed after incubation with the ayahuasca samples. In conclusion, the main results of this thesis demonstrated that ayahuasca does indeed have a great therapeutic potential, with emphasis on its antimicrobial, antioxidant, anti-inflammatory, and healing actions, but above all its anticancer activity studied in two different cell lines. Also noteworthy was the development and validation of the analytical method where three miniaturized extraction techniques were compared and where the QuEChERS technique was applied to ayahuasca samples for the first time.
- 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.