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Purine alkaloids in Paullinia

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Abstract

Among the few purine alkaloid-containing genera consumed as stimulants, Paullinia is the least investigated with respect to both chemotaxonomy and within-the-plant allocation of caffeine and its allies. Since purine alkaloids (PuA) have been proved to be valuable marker compounds in chemotaxonomy, 34 species of Paullinia and related genera were screened for them, but only one, P. pachycarpa, was positive in addition to the already known P. cupana and P. yoco. The PuA allocation in P. pachycarpa was examined and found to be restricted to theobromine in the stem, leaves and flowers. Moreover, the theobromine concentration in the stem cortex increased significantly towards the base of the plant. Since the stem cortex of P. yoco is traditionally used by the natives of Colombia and Ecuador to prepare a caffeine-rich beverage, we suspected that within the genus Paullinia the PuA are preferentially allocated to the older parts of the stem and not to young shoots like e.g., in the coffee plant (Coffea spp.). Indeed, the axis (greenhouse) of P. cupana (guaraná), known for its caffeine-rich seeds, exhibited a basipetal PuA gradient (0.005-0.145%). Moreover, the analysis of young cortex samples (herbarium) and of one piece of old stem (museum collection) revealed the same for P. yoco, even though we found much less (0.5 vs 2.5%) caffeine in the old cortex as compared to the only two analyses in 1926 of similar material. However, this discrepancy may be explained by the high variability of the PuA pattern we detected among yoco, the diversity of which the Indians take advantage.

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... Stimulating beverages have been developed and are consumed by virtually all human cultures (Weinberg & Bealer 2001). Of the six caffeine-containing plant genera used as stimulants (Coffea, Camellia, Theobroma, Cola, Ilex, and Paullinia), Paullinia, a genera of woody vines or lianas in the Sapindaceae family, is the least studied (Weckerle et al. 2003). Two species within this genus have been found to contain purine Alkaloids (PuA): Paullinia cupana Kunth and Paullinia yoco R.E. ...
... To assess the economic potential of P. yoco, a better understanding of the plant's stimulant chemical concentration , the within-plant distribution of stimulant chemicals, and variance in chemistry between genetic provenances is critical. To date, very little research has been conducted on P. yoco, and worldwide only 40 herbarium specimens have been collected (Weckerle et al. 2003). The first reported chemical analysis was in 1926, where levels of caffeine were found to range between 2.0 and 2.7% (Michiels & Denis 1926). ...
... Another more recent study used previously collected herbarium specimens and found concentrations two orders of magnitude lower—median values for phloem material were 0.1% caffeine and 0.05% theobromine; and for leaf material were 0.03% caffeine and 0.03% theobromine. This contrast resulted in Weckerle et al. (2003) summarizing their findings by saying " clearly fresh stem material of various P. yoco provenances will be necessary to fully resolve the 'yoco mystery.' " This research, therefore, aims to elucidate the 'mystery' of this Amazonian liana through the analysis of fresh stem material of 18 P. yoco provenances , with sampling from multiple stem diameters and vegetative parts, collected under the guidance of indigenous experts. Specifically, the following hypotheses will be addressed: (1) caffeine and theobromine concentrations from fresh material are higher than those found in herbarium material by Weckerle et al. (2003) , (2) caffeine and theobromine concentrations are higher in phloem than in leaves and positively correlated to stem diameter, and (3) there is considerable between-plant variation in caffeine and theobromine content. ...
Article
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Paullinia yoco R.E. Schult. & Killip (Sapindaceae) or 'yoco', is a liana (a woody vine) used traditionally by indigenous peoples of the upper Amazon region as a stimulating beverage, because it contains both caffeine and theobromine. However, as the wild plants become increasingly rare and hard to find because of permanent settlement within a much-reduced territory, there is growing interest among indigenous tribes to learn how to successfully cultivate it for community consumption and potentially as a cash crop. To date, there has been very little research conducted on the stimulant chemical composition of the liana and biochemical variation within-and between plants. This paper provides the results of chemical (high-performance liquid chromatography) analysis of caffeine and theobromine concentrations of multiple samples of phloem and leaf material from 18 Paullinia yoco lianas. Caffeine values ranged from 0.1% to 3.6% with a significantly higher amount in the stem phloem material than the leaf material, and there was a positive linear correlation between stem diameter and caffeine concentration (% dry weight). Although the highest theobromine level was found in leaf material (1.8%), overall there was no significant difference between phloem and leaf material, and no correlation between stem diameter and theobromine concentration. Finally, we found a significant amount of variance of both caffeine and theobromine between individual plants. These results are important, first because they shed light on the apparently conflicting previous reports on P. yoco caffeine and theobromine content; and second, they provide important clues about the phytochemical architecture of P. yoco which in turn has important implications for the design of a cultivation strategy for local indigenous communities to potentially produce a yet-to-be domesticated plant of substantial market potential. Paullinia yoco R. E. Schult. Y Killip (Sapindaceae) o 'yoco', es una liana (una enredadera leñosa) utilizado tradicionalmente por los pueblos indígenas de la región amazónica superior como una bebida estimulante, ya que contiene cafeína y teobromina. Sin embargo, como las plantas silvestres son cada vez más raros y difíciles de encon-trar debido a asentamiento permanente en un territorio muy reducido, existe un creciente interés entre las tribus indígenas para aprender cómo cultivar con éxito para el consumo de la comunidad y, potencialmente, como cultivo comercial. Hasta la fecha, ha habido muy poca investigación realizada sobre la composición química estimulante de la liana y bioquímica intra-variación y entre plantas. Este trabajo presenta los resultados del análisis química (cromatografía líquida de alta resolución) de las con-centraciones de cafeína y teobromina de múltiples muestras de material floema y hoja de 18 lianas Paullinia yoco. Valores de cafeína variaron de 0,1% a 3,6% con una cantidad significativamente mayor en el material de floema * Luke Weiss was born in British Columbia, and with most of his upbringing in Manchester, Michigan. He received a B.S. in biology from The Evergreen State College. Before coming to Yale F&ES, he spent 18 years living in the tropics of northeastern Ecuador working on numerous conservation and development projects with the Secoya indigenous nation. Currently he is an MF candidate, with interests in tropical restoration and sustainable land-use management. His research is focused on designing a sustainable cultivation system for a caffeine-rich liana traditionally consumed by the Secoya people which is becoming increasingly rare in the wild. Correspondence: de que el material de hoja, y había una correlación lineal positiva entre el diámetro del tallo y la concen-tración de cafeína (% peso seco). Aunque el nivel teobromina más alta se encontró en el material de la hoja (1,8%), no hubo diferencia significativa entre el floema y el material de hoja, y no hay correlación entre el diámetro del tallo y la concentración de teobromina. Finalmente, se encontró una cantidad significativa de varianza de cafeína y teobromina, tanto entre los individuos. Estos resultados son importantes, primero porque arrojan luz sobre las aparentemente contradictorios informes anteriores sobre P. yoco cafeína y teobromina contenido; y segundo, que proporcionan importantes pistas sobre la arquitectura fitoquímico de P. yoco que a su vez tiene implicaciones im-portantes durante el diseño de una estrategia de cultivo para las comunidades indígenas locales para producir una planta todavía-a-ser domesticada del potencial de mercado importante.
... Generally, caffeine is measured at outstanding levels in phytochemical analyses, which roughly comprises 2.5% to 5% of the guarana dry weight extract (Weckerle et al., 2013). Caffeine is a natural alkaloid that, depending on the dose and the frequency of use, has varied beneficial biological properties: it acts as an antioxidant, an antibacterial and an anti-inflammatory substance, besides acting as an antidepressant, anti-mutagenic, cyto-protective, and neuro-protective agent (Da Silva et al., 2018;Viana et al., 2020). ...
... The species P. cupana (guarana) contains high levels of caffeine (1,3,7-trimethylxanthine) in its chemical composition, especially the seed to which the stimulant properties of guarana are best attributed (Schimpl et al., 2013;Tfouni et al., 2017). In order to estimate, the caffeine content in guarana is 4 times greater than in coffee (Coffea arabica L.) and 10 times greater than in tea (Camellia sinensis L.) (Weckerle et al., 2013). Namely, Caffeine is one of the most ingested alkaloids whose effects on humans have been the subject of studies for some decades because it presents several pharmacological actions to the body (Viana et al., 2021a), mainly related to an increase in alertness (Nawrot et al., 2003), a reduction in fatigue (Espinosa;Sobrino Mejía, 2017), as well as an improvement in the performance of different activities (Temple et al., 2017). ...
Article
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Paullinia cupana (Kunth), popularly known as guarana, is a plant species from the Amazon Region of Brazil that stands out for being one of the most promising herbal medicines of the Brazilian flora since it has relevant biological properties. However, studies are still needed to use this species as a direct approach to evaluate aspects related to behavior and oxidative stress in invertebrate model animals. In this context, we aimed to evaluate the stimulant and the antioxidant effects of P. cupana in lobster cockroach Nauphoeta cinerea. For that, cockroaches were exposed to a diet separately supplemented by the decoction of P. cupana powder decoction at increasing concentrations of 1, 25, 50 and 100 mg/g for 42 days. Behavioral and biochemical assays were performed, respectively, to assess the locomotor/exploratory performance and oxidative stress marker levels of the cockroaches. They exhibited an outstanding increase in the locomotion performance and in the cell viability content, as well as in the protein and non-protein thiol levels. Moreover, there was a decrease in lipid peroxidation levels and in free Fe2+ ion contents. Together, our results demonstrate the stimulant and the antioxidant capacity of P. cupana by acting positively in behavioral patterns and by regulating oxidative stress markers in lobster cockroach N cinerea. These findings encourage further laboratory analyzes in order to better enlighten the specific mechanisms of action attributed to guarana.
... There is no evidence in the literature of the metabolic role of theophylline in the tissues of guarana, although it is eventually detected in seeds (Machado et al., 2018;Schimpl et al., 2014). Weckerle, Stutz, and Baumann (2003) found TB content (0.015%) in Paullinia cupana seeds. In other CFaccumulating plants, such as Paullinia pachycarpa Benth. ...
... In other CFaccumulating plants, such as Paullinia pachycarpa Benth. and tea, TB and theophylline were not detected (Ashihara & Kubota, 1986;Weckerle et al., 2003). Cardozo et al. (2007) found significant differences in the total content of methylxanthine (CF and TB) and phenolic compounds in yerba mate progenies. ...
Article
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Guarana is a typical South American plant, native to the Amazon, with subspontaneous occurrence in Maués, Amazonas‐Brazil, where it was domesticated and cultivated by the Sateré‐Mawé indigenous community. Guarana is an original Brazilian product with great economic and industrial potential owing to the energetic, antioxidant and medicinal properties of its seeds. In spite of its importance, there is still a gap in knowledge about genetic diversity and adaptations that might improve agro‐industrial uses of guarana seeds. This study was aimed at estimating phytochemical diversity, classification and typology of guarana genotypes. Agro‐industrial potential among eight genotypes was estimated based on phytochemical characters (theobromine, caffeine, catechin and epicatechin content (quantified by HPLC) and yield in three locations, in harvests between 2015 and 2016. Phytochemical divergence was assessed by the mean Euclidean distance. Grouping was performed by the Unweighted pair‐group method using arithmetic averages (UPGMA). Metabolite content varied considerably between genotypes; for example, caffeine (3.23 to 7.35%), catechin (0.20 to 3.57%) and epicatechin (0.09 to 4.22%), and dry seed yield was the character with the highest variation (0.048 to 5.13 kg.plant−1). The metabolic profile variations of the genotypes were clustered into three chemotypes: energetic and antioxidant guarana (genotypes CIR815, CIR904, CMA498); antioxidant guarana (genotypes BRS‐Maués, CMU874); and energetic guarana (genotypes CMA831, CMU952, BRS‐CG372). Genotypes CIR815, CIR904, and CMU874 have the potential to be future commercial cultivars, providing quality raw material for soft drinks, energy drinks and pharmaceutical products. This article is protected by copyright. All rights reserved
... sorbilis), which are utilized commercially in South America as a beverage and flavouring ingredient, contain high concentrations (2.5-6.5% d.w.) of caffeine with lower amounts of theobromine and theophylline (Schimpl et al. 2014 of theobromine (0.015%) and theophylline (0.007%). Caffeine also occurs in the testa and septa while, in contrast, theobromine was detected mainly in the leaves, stem, and pericarp (Table 14.8) (Baumann et al. 1995;Weckerle et al. 2003). ...
... Smaller amounts of theobromine (0.03-0.05%) accumulate in the mature leaves, axis cortex, and floral buds, while theophylline has not been detected in any part of this plant. P. pachycarpa accumulated only small amounts of theobromine (<0.03%) in the leaves and stems, and no purine alkaloids were detected in the fruits (Weckerle et al. 2003). Stewart (1985) reported the presence of a low concentration of caffeine in the flower buds of eight cultivars of citrus and in the leaves of Valencia orange (Citrus sinensis). ...
Chapter
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The most well‐known secondary metabolites synthesized from nucleotides are purine alkaloids. Purine alkaloids, namely methylxanthines and methylurates, occur in a variety of plant species. The major purine alkaloid typically is caffeine, which is found in popular non‐alcoholic beverages such as coffee, tea, and matĕ. The biosynthetic pathway of caffeine from purine nucleotides was established by extensive purification of tea caffeine synthase and the cloning of the gene encoding this enzyme. The distribution of purine alkaloids within matĕ plants has been reported. Theacrine is a purine alkaloid found in seeds of many Theobroma species except for Theobroma cacao: Theobroma speciosum, Theobroma micro‐carpum, Theobroma angustifolium, Theobroma grandiforum, Theobroma subincanaum, and Theobroma mammosum. Sapindales, Paullinia (Sapindaceae) and Citrus (Rutaceae) species also contain purine alkaloids. Biosynthesis of purine alkaloids is well‐documented in Camellia and Coffea species, although different routes may be operative in other species.
... sorbilis), which are utilized commercially in South America as a beverage and flavouring ingredient, contain high concentrations (2.5-6.5% d.w.) of caffeine with lower amounts of theobromine and theophylline (Schimpl et al. 2014 of theobromine (0.015%) and theophylline (0.007%). Caffeine also occurs in the testa and septa while, in contrast, theobromine was detected mainly in the leaves, stem, and pericarp (Table 14.8) (Baumann et al. 1995;Weckerle et al. 2003). ...
... Smaller amounts of theobromine (0.03-0.05%) accumulate in the mature leaves, axis cortex, and floral buds, while theophylline has not been detected in any part of this plant. P. pachycarpa accumulated only small amounts of theobromine (<0.03%) in the leaves and stems, and no purine alkaloids were detected in the fruits (Weckerle et al. 2003). Stewart (1985) reported the presence of a low concentration of caffeine in the flower buds of eight cultivars of citrus and in the leaves of Valencia orange (Citrus sinensis). ...
Chapter
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Purines and pyrimidines are major chemical constituents of cells and occur primarily as components of DNA and RNA (polymerized nucleotides), and to a much lesser extent in the form of ‘free’ (aka ‘soluble’) nucleotides. Compared with nucleotides, free nucleosides and bases usually represent a very small fraction of the total purine and pyrimidine content of living cells, including plant cells. However, there are exceptions to this generalization, including the occurrence of substantial amounts caffeine in plants such as coffee (Coffea arabica and Coffea robusta) and tea (Camellia sinensis), and theobromine in cocoa (Theobroma cocao). This chapter summarizes occurrence of major purine, pyrimidine, and pyridine nucleotides in plants. For comparison, it considers cytokinins and nucleotide alkaloids. In most plants, the concentration of nucleotides is higher than nucleosides and bases. Cytokinins occur in much lower amounts than purine nucleotides. A much higher concentration of caffeine is found in tea and coffee plants.
... The Shuar use Eupatorium macrophyllum leaves to treat headache [12]. From Perymenium ecuadoricum some kaurene diterpenes and some kaurene isovalerian esters (92)(93)(94)(95)(96) were isolated ( Figure 12) [34]. Schistoscarpha eupatorioides, an Asteraceae from the Heliantheae tribe, is used to cure internal ulcers and diarrhea and to heal wounds. ...
... The compounds are shown in Figure 37. The stem cortex of Paullinia yoco (Sapindaceae) is traditionally used by the natives of Ecuador to prepare a caffeine rich beverage [95]. Picramnia sp. ...
Article
Ecuador owns many high quantity and wealthy ecosystems that contain an elevated biodiversity in flora and fauna. The use of native medicinal plants has been maintained by at least 18 different indigenous cultures; furthermore, this country has been the witness of the discovery of important medicinal plants, such as Cinchona, and is an understudied resource of new natural products. The objective of this review is to update the ethnopharmacological and phytochemical studies accomplished on the Ecuadorian flora, pointing to the 253 native families and more than 15,000 species registered at present.
... Weckerle y col. (1), abordan en una publicación reciente la investigación de la composición quimiotaxonómica de 34 distintas especies del género Paullinia. ...
... El guaraná ha sido objeto de diversos estudios químicos como la determinación de aceites esenciales (51), el estudio de los componentes del aceite de la semilla (52), la extracción de su metilxantinas por métodos supercríticos (21), la determinación de metales (57), el contenido de cafeína en diferentes variedades (1). A nivel fisiológico se han estudiado sus efectos adelgazantes (50,53), efectos mutagénicos y genotóxicos (54), sus efectos estimulantes tanto en animales de laboratorio como en humanos (24,30,55), y sus efectos tóxicos in vitro (56), De todos ellos, los que más se destacan son los que tratan de la seguridad del consumo de guaraná y de sus propiedades. ...
Article
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This review involves a general description of Guaraná, including its chemical and pharmacological properties as well as its production, consumption and economical importance. The revision covers the period between 1931 and 2005, in which 82 papers are considered concerning the botanic and chemical characteristics, the pharmacological activity and the medicinal properties of Guaraná.
... Weckerle y col. (1), abordan en una publicación reciente la investigación de la composición quimiotaxonómica de 34 distintas especies del género Paullinia. ...
... El guaraná ha sido objeto de diversos estudios químicos como la determinación de aceites esenciales (51), el estudio de los componentes del aceite de la semilla (52), la extracción de su metilxantinas por métodos supercríticos (21), la determinación de metales (57), el contenido de cafeína en diferentes variedades (1). A nivel fisiológico se han estudiado sus efectos adelgazantes (50,53), efectos mutagénicos y genotóxicos (54), sus efectos estimulantes tanto en animales de laboratorio como en humanos (24,30,55), y sus efectos tóxicos in vitro (56), De todos ellos, los que más se destacan son los que tratan de la seguridad del consumo de guaraná y de sus propiedades. ...
Article
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RESUMEN Esta revisión tiene por objeto presentar una descripción general del Guaraná, abarcando tanto sus propiedades químicas y farmacológicas como su aspecto económico, producción y consumo. Se han seleccionado un total de 82 artículos de los que se recogen las características botánicas y químicas, la actividad farmacológica y las propiedades medicinales del Guaraná, en el período comprendido entre 1931 y 2005. ABSTRACT This review involves a general description of Guaraná, including its chemical and pharmacological properties as well as its production, consumption and economical importance. The revision covers the period between 1931 and 2005, in which 82 papers are considered concerning the botanic and chemical characteristics, the pharmacological activity and the medicinal properties of Guaraná.
... Several species of Paullinia contain purine alkaloids (Weckerle et al., 2003). The leaf extracts of P. pinnata contain paullinoside A, paullinomide A, as well as β-amyrin (Miemanang et al., 2006). ...
... Coffee is the primary source of caffeine ingested by adults, whereas soft drinks and tea are the predominant sources for adolescents (van Dam et al., 2020). Caffeine is also present in Camellia, Theobroma, Cola, Ilex, and Paullinia (Weckerle et al., 2003). Additionally, caffeine is one of the main ingredients for several industries, such as the pharmaceutical, cosmetic, nutraceutical, and energy drink industries (McLellan & Lieberman, 2012). ...
Article
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This study compared the green solvents ethyl acetate and water for caffeine extraction from coffee pills against four traditional solvents (ethanol, methanol, acetone, and acetonitrile). Each solvent's green degree (GD) was calculated using seven environmental and technical performance parameters. The environmental parameters were obtained from the Glaxo Smith Kline guide. Fick's law of effective diffusion was used as the technical parameter. Water was selected as the preferred solvent (among the six evaluated in this study), and its ultrasound‐assisted extraction (UAE) conditions were optimized. The optimal conditions were estimated by ridge analysis. It was found that caffeine extraction was approximately 4.3 times higher in UAE than in conventional solid–liquid processes, and the extraction time was reduced by 96%. Moreover, this process improved caffeine extraction with water. Therefore, the use of UAE over conventional solid extraction and water as an inexpensive, easily accessible, manageable, and environmentally friendly solvent provides extraction alternatives for caffeine in different matrices. Additionally, a methodology is proposed to evaluate the GD for each solvent in the green chemistry framework to achieve sustainable development goals. Process of caffeine extraction.
... Reported phytoconstituents of the leaves of several Paullinia species include purine alkaloids (Weckerle et al., 2003). Flavonoids, phenolic compounds, triterpenes, cardiotonic catechol tannins, and saponins have been isolated from the plant (Bowden, 1962;Broadbent, 1962). ...
Article
Purpose Leaf extracts of Paullinia pinnata L. (Sapindaceae) are used in ethnomedicine for the treatment of central nervous system-related diseases such as insomnia and epilepsy. We determined the bioactive constituents, sleep-enhancing and anti-convulsant potentials, and possible mechanisms of action of P. pinnata methanol leaf extract (PPME). Methods Gas Chromatography-Mass spectrometry (GC-MS) was used to identify the bioactive compounds in PPME. Adult Swiss albino mice were used. Oral LD50 was estimated before administering PPME at oral doses of 100, 200, and 400 mg/kg to test for sleep-enhancing and anticonvulsant properties. To evaluate the possible mechanisms involved, mice were pretreated for five days with isoniazid (NIH) a GABA synthesis inhibitor before re-evaluation of sleep-enhancing property. The activities of glutamic acid decarboxylase (GAD), superoxide dismutase (SOD), catalase (CAT), and the level of malondialdehyde (MAD) in the brain of mice were also evaluated after a 7-day treatment with the extract. Results Twenty-five phytochemical compounds were identified from GC-MS analysis with fatty acid esters of lauric and fumaric acids being the most abundant. The oral LD50 of PPME was estimated to be greater than 5000 mg/kg. Doses of PPME significantly (p < 0.001) reduced sleep latency and increased the duration of sleep of phenobarbital-treated mice. Except for 100 mg/kg, the doses also significantly protected mice against maximum electroshock (p < 0.001) and pentylenetetrazole (p < 0.05) but not strychnine-induced convulsions. Pretreatment with isoniazid (INH) almost completely reversed the sleep-enhancing effects of PPME. The activities of GAD, SOD, and CAT, and level of MDA in brains of the mice were significantly (p < 0.001) increased by doses of PPME administered for five days. Conclusion The extract possesses sleep-enhancing and anticonvulsant properties which depend on increased level of GABA in the brain. Its antioxidant action may be neuroprotective against free radicals-induced damage.
... Paullinia cupana (Guarana seeds) is mainly used by the soft drink industries to produce non-alcoholic beverages. Guarana drinks have potent stimulating properties because of its seeds rich in caffeine (Weckerle et al., 2003). It possesses weight loss by increasing metabolism and suppressing appetite, improves cognitive performance as well as used as antidepressant (Andersen & Fogh, 2011;Kennedy, 2008;Scholey & Haskell, 2008). ...
Article
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The low calorie diet drinks is entering into a new era as preferred by different age groups. All these beverages are having no fruit or vegetable juice, which need to be taken care. Therefore, present study was aimed to develop a fruit‐oriented (watermelon) diet drink using different variables i.e. tea extract (0‐20%), herb extract (0‐5%) and sorbitol (5‐10%) and the optimization was carried out using CCD of RSM. The optimum quality attributes; TSS sucrose (14.85°B), glucose (14.96°B), titratable acidity (citric acid) (0.161%), pH (3.97), reducing sugars (1395 mg/100 ml), total sugars (10.97 g/100 ml), anti‐diabetic assay (72.42 %), calorific value (41.88 kcals/100 ml), total proteins (166.03 mg/100 ml), total phenolics (362.03 mg/100 ml), total tannins (173.20 mg/100 ml), anti‐oxidant activity (56.02%), total flavonoids (1696 mg/100 ml), caffeine (45.33 mg/100 ml), sodium (14.35 ppm), potassium (69.03 ppm) and overall acceptability (8.08) was obtained using 8.74% tea extract, 2.5% herb extract and 6.75% sorbitol with 0.853 desirability. FTIR analysis also confirmed the presence of physiochemical and phytochemicals and cluster analysis revealed that tea extract concentration has a more influence on the quality attributes of drink. The developed conditions will help the industrials and researchers for development of fruit‐based diet drink will high range of phytochemical potential.
... 301-324; Vickers, William y Thimoty Plowman (1984). "Useful Planls of the Siona Secoya Indians of Eastern Ecuador", Fieldiana 15;Weckerle C.S. (2003). "Purine alkaloids in Paullinia". ...
Thesis
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Legal institutions exclusively focused on human perspectives seem insufficiently capable of addressing current socio-ecological challenges in the Andean-Amazonian foothills of Colombia. It is critical to probe new analytical frameworks that integrate other-than-human beings within legal institutions and decision-making protocols in this region. Such an approach weaves together various fields of knowledge and world-making practices that include—but are not limited to—Indigenous legal traditions, ecological law, multispecies ethnography, and ecological economics. My dissertation discusses how human and other-than-human beings such as medicinal plants and what Indigenous peoples in Southwestern Colombia call the “invisible ones” (los invisibles) co-create legal protocols and institutions. Furthermore, it studies the conceptual openings, methodological challenges, and ethical conundrums of this approach for the broader Earth Law movement, particularly the rights of nature. What happens when we consider forms of agency beyond symbolic and multicultural frameworks in legal theory and practice? How does a law that emerges from plant-human-“invisible” peoples’ entanglements challenge concepts of justice, agency, and value in times of socio-ecological transitions? How do forests become legal agents through different sets of territorial practices? My dissertation combines a multi-sited ethnography and a post-humanist approach in anthropology, law, and decision-making theory to study the entangled lives of law and ecology in the regions of Nariño and Putumayo, as well as the potential contributions of this framework towards a post-anthropocentric legal theory. In conversations with biologists, Indigenous practitioners from the Cofán and the Inga communities, legal scholars, and medicinal plants, particularly Yoco (Paullinia yoco) and Yagé (Banisteriopsis caapi), Legal Lives looks at how legal institutions emerge from the fabric of human and other-than-human forms of agency. This relational approach is at the core of the Earth Law movement and the radical paradigm shift it proposes for legal theory and practice in Latin America and beyond. The dissertation is divided into three parts. The first one (I. Towards a Law Otherwise) offers an ethnographic approach to the law and comprises two chapters on the relationship between medicinal plants and legal protocols. Moreover, it includes three sub-chapters with the name of three different plants where I discuss the implications of vegetal agencies for socio-legal thought in the Andean-Amazonian region today. To further explore the connections between other-than-humans and the law, chapter 2 (“Los Invisibles”) focuses on the making of an ethnobotanical research protocol with humans, plants, and what members of the Cofán community in the regions of Nariño and Putumayo refer to as the “invisible people” (los invisibles). Thus, Towards a Law Otherwise provides an ethnographic and conceptual basis to support the theoretical claims of the second part of the dissertation, namely: The Rights of Nature: Limits and Possibilities. Part II addresses some of the conceptual limits and political possibilities of the Rights of Nature in Latin America in the context of an emerging Earth Law movement. By attending to the social and legal worlds of other-than-human beings introduced in the first part of the dissertation, Rights of Nature proposes to reimagine fundamental premises of social and legal sciences at present, namely, (a) the idea that the law is primarily symbolic or propositional; (b) the notion that rights and responsibilities are commensurable across different legal cultures and cosmologies (Ch. 3 “Conjuring”), and that (c) the concept of legal personhood is fundamental for legal redress (Ch. 4 “Forest on trial”). Part II, a contribution to a relational theory of legal agency, therefore critically assesses core notions of Western law such as legal personhood, standing, rights and responsibilities. The third and final part of the dissertation (III. Rhizomatic Agencies) reviews and summarizes the argument concerning agency and discusses how parts I and II could serve as tools for legal transformation in concrete scenarios of learning and judicial decision-making. A summary of agency theory with ethnographic insights from the first section, chapter 5 (“Agency Scaffolding”) dives into the limits of individual and collective forms of agency and explores the possibility of plural and rhizomatic agencies that include other-than-human beings in decision-making protocols. Chapter 6 (“Worlding with Indigenous Law: A teaching and learning proposal”) can be considered as coursework material concerning Indigenous legalities. It refers to a specific Indigenous legal tradition—the Inga—as it transforms State law, while contributing with an emerging global Earth Law movement. The dissertation closes with a syllabus on “Indigenous legal traditions: from the Boreal to the Amazonian forests” (Chapter 7).
... Coffee is the primary source of caffeine ingested by adults, whereas soft drinks and tea are the predominant sources for adolescents (van Dam et al., 2020). Caffeine is also present in Camellia, Theobroma, Cola, Ilex, and Paullinia (Weckerle et al., 2003). Additionally, caffeine is one of the main ingredients for several industries, such as the pharmaceutical, cosmetic, nutraceutical, and energy drink industries (McLellan & Lieberman, 2012). ...
... The cognitive benefit of guarana is proposed to be related to its ability to decrease the physiological response to physical or psychological stressors [59]. It has been proposed that the impact of guarana on cognition is due to the synergistic effect of its constituents, such as caffeine [105] and theanine [106]. ...
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Intake of dietary supplements has increased, despite evidence that some of these have adverse side effects and uncertainty about their effectiveness. This systematic review examined the evidence for the cognitive benefits of a wide range of dietary supplements in healthy young adult samples; the aim was to identify if any might be useful for optimising cognitive performance during deployment in military personnel. Searches were conducted in 9 databases and 13 grey literature repositories for relevant studies published between January 2000 and June 2017. Eligible studies recruited healthy young adults (18–35 years), administered a legal dietary supplement, included a comparison control group, and assessed cognitive outcome(s). Thirty-seven of 394 identified studies met inclusion criteria and were included for synthesis. Most research was deemed of low quality (72.97%; SIGN50 guidelines), highlighting the need for sound empirical research in this area. Nonetheless, we suggest that tyrosine or caffeine could be used in healthy young adults in a military context to enhance cognitive performance when personnel are sleep-deprived. Caffeine also has the potential benefit of improving vigilance and attention during sustained operations offering little opportunity for sleep. Inconsistent findings and methodological limitations preclude firm recommendations about the use of other specific dietary supplements.
... The seeds contain about twice the concentration of caffeine than that found in coffee seeds (about 2-4.5% caffeine in guarana seeds compared with 1-2% for coffee seeds) with 1 g of guarana being equivalent to about 40-mg caffeine [46]. Guarana contains other xanthine alkaloids, like theobromine and theophylline, however, at much lower levels compared with caffeine [47]. Guarana has become an increasingly common natural additive in energy drinks mainly for its stimulatory effect, which is anyway slighter and featured by a slower action than pure caffeine [48]. ...
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Energy drinks are increasingly used by young people and young athletes in order to improve their performance alone or in association of other substances, particularly alcohol. In recent years, a number of reports of reports have raised attention on the side-effects associated with the use or abuse of energy drinks particularly serious cardiovascular events. The European Cardiac Arrhythmia Society (ECAS) has undertaken a systematic and critical review of reported data on cardiovascular events including life-threatening arrhythmias with or without cardiac arrest and other cardiovascular events, and discussed in this review the possible causal effect of caffeine and other ingredients contained in energy drinks and the reported events. Twenty-two cardiovascular events were reported in association with the use or abuse of energy drinks. The European Cardiac Arrhythmia Society would like to draw attention on the possible cardiovascular complications that may occur with the consumption of these beverages and to emphasize the prevention measures to be taken particularly in the young population. Well-designed prospective studies are needed to clarify the possible role of energy drinks in inducing the cardiovascular events reported.
... The stimulant properties of guarana drinks are reportedly due to caffeine. It contains about twice the concentration of caffeine as found in coffee beans, as 1 gm of guarana is equivalent to 40 mg of caffeine (125). Guarana seeds are a richer source of epicatechin which has potent antioxidant and anti-inflammatory effects (66). ...
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Background: The purpose of this review paper was to explore the components and their respective health effects and safety aspects regarding the consumption of diet drinks (DDs). Methods: A wide variety of the relevant publications (published before 2018) were identified through searching electronic databases (ScienceDirect, PubMed, SciELO, Google Scholar, Springer Link, and ResearchGate) on the basis of different keywords such as diet drink, market status, consumption pattern, composition, health effects, and regulations related to DDs. After the search of suitable literature, 139 papers were screened and reviewed. Results: Numerous brands of DDs have been introduced in the market along with a wide variety of modifications in order to attract the consumers of all age groups along with their respective professions. The major components of DDs are caffeine, taurine, ginseng, guarana, sodium, potassium, and sweeteners that contribute to the good taste, stimulating effect, increased performance and cognitive function, and reduced stress. However, ingestion of DDs over a prolonged course of time can pose multiple deleterious effects, i.e., intoxication, affective disorder, hypertension, reproductive toxicity, and neurological disorders. Consequently, different regulatory bodies of respective countries have formulated and enforced rules and regulations regarding the composition, consumption, labeling, distribution, and sales of DDs. Conclusions: An awareness regarding the components, consumption, and health effects is greatly required in the present era, and authors have tried to fill this gap. • Key teaching points • Rise in socio-economic status, health awareness and change in dietary lifestyle are the major factors that fuel the demand of diet drinks; which has been witnessed by a drastic increase in the consumption pattern of the diet drinks among young to middle-age adults since last decade. • A wide variety of the ingredients are used in the preparation of diet drinks including caffeine, ginseng (Panax ginseng), guarana (Paullinia cupana), taurine, artificial sweeteners, B Vitamins, sodium, potassium etc. • Diet drinks are generally served cold and contain high levels of caffeine and other artificial sweeteners; which based on dosage, have been known to be beneficial as well as harmful. • These ingredients possess numerous health benefits including anti-hypertensive, anti-oxidant, anti-cancer properties, improved metabolic functions, stress reduction and enhanced endurance, exercise and performance and increased cognitive function. • A wide range of the adverse health effects such as nervousness, sleeplessness, behavioral changes, decreased appetite, heart palpitations, nausea, vomiting, dehydration etc. is being possessed by diet drinks upon the ingestion of these drinks over a prolonged course of time. • Regulatory bodies should determine the safe limits of all ingredients for different age groups to get maximum health benefits.
... Paullinia cupana Kunth, commonly known as guarana, is a typical Brazilian plant species and is of major economic interest within the genus Paullinia (Henman 1982;Beck 1990). Chemically the seeds contain high concentrations of methylxanthines such as caffeine, theophylline and theobromine, as well as saponins and polyphenols, especially condensed tannins, while the seed oil contains cyanolipids (Pagliarussi et al. 2002;Avato et al. 2003;Weckerle et al. 2003;Antonelli-Ushirobira et al. 2007;Yamaguti-Sasaki et al. 2007;Marques et al. 2016). Plant extracts containing polyphenols have shown significant antimicrobial activity against H. pylori, as demonstrated by Pastene et al. (2009). ...
Article
Paullinia cupana Kunth, commonly known as guarana, is a native Brazilian plant species from the Amazon area that presents various biological effects, including antimicrobial action. The aim of this study was to chemically analyse the semipurified aqueous extract (AqF) of the plant and to evaluate the activity of crude (CE), ethyl-acetate (EAF), and AqF extracts against Helicobacter pylori. The chemical profile of AqF was determined based on solid analysis ¹³C-NMR, direct infusion mass spectrometry (ESI-MS), and MALDI-TOF. The ¹³C-NMR spectrum showed characteristics of flavan-3-ol and oligomeric proanthocyanidins. ESI-MS revealed the presence of procyanidin, caffeic acid and its derivatives. MALDI-TOF analysis detected procyanidins of up to 6 units and profisetinidins of up to 5 units. Whereas CE and EAF showed inhibitory activity against H. pylori, CE, EAF, and AqF presented not high inhibitory activity against urease. The results demonstrate the potential of P. cupana to control and prevent H. pylori infection.
... This is not necessarily true, particularly if taken with prescription drugs, over-the-counter medicines or used in combination with other herbs. Moreover, they may have adverse side (Marx and Maia, 1990;Baumann et al., 1995;Meurer-Grimes et al., 1998;Andrade et al., 1999;Pagliarussi et al., 2002;Weckerle et al., 2003;Ushirobira et al., 2004;Sombra et al., 2005;Pagliarussi et al., 2006;Tfouni et al., 2007;Ushirobira et al., 2007;Yamaguti-Sasaki et al., 2007;Sousa et al., 2010;Klein et al., 2012;Bittencourt et al., 2013;Schimpl et al., 2014) Theobromine (2) (3,7-dimethylxanthine) Theophylline (3) (1,3-dimethylxanthine) ...
Article
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Seeds of guarana (Paullinia cupana Kunth, Sapindaceae) feature diverse pharmacological functions, for example, antimicrobial, antioxidant, anticarcinogenic, stimulating, and cognitive functions, as well as liver protection and weight loss. Many of these actions are probably due to the high content of methylxanthines and tannins in its seeds. In Brazil, the world's largest producer of guarana, the plant material is predominantly used in the soft drinks industry, although it is also used in the cosmetic and pharmaceutical industries. Although the Amazon region has the largest cropping area, the state of Bahia is the main guarana producer in Brazil (71%). This review focuses mainly on the possible pharmacological actions of guarana that have been investigated. Moreover, it discusses less-considered topics, such as the toxicology and quality control of seeds and extractives of guarana that will ultimately influence the safety of its use. In addition, it presents a detailed discussion of the methods used to prepare herbal drugs and their extracts, focusing on the importance of standardization and on the direct impact of preparatory factors, on the pharmacological properties of guarana extracts.
... Paullinia cupana (Sapindaceae), popularly known as Guarana, is a plant native to the Amazon basin. It contains purine alkaloids, such as caffeine, theophylline and theobromine, which are responsible for the stimulating effects of guarana 1 . The caffeine content in samples of guarana extract presents great variability, ranging from 9.52 to 36.71 mg/g of powder, and when compared to the dry extract of coffee, the caffeine concentration is about four times higher 2 . ...
Article
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Previous studies in patients with advanced cancer have reported that Cat’s claw dry extract (Uncaria tomentosa) and Guarana (Paullinia cupana) showed beneficial effects in patients with terminal cancer. Our objective is to investigate the combined action of these extracts in the control of symptoms in these patients. This prospective, uncontrolled pilot study evaluated the use of 100 mg of U. tomentosa dry extract three times daily combined with 50 mg of P. cupana dry extract twice daily in terminal patients with solid tumors who were ineligible for traditional therapeutic approaches. Patients had blood collected and answered questionnaires (EORTC QLQ-C30, FACIT-F, Chalder Fatigue Scale, HADS and PSQI-BR) before and after 3 and 6 weeks of treatment. Twenty-two volunteers were recruited; the mean age of the population was 68.3 years (range, 49-89 years), 86.3% were men, and half had a Karnofsky Index less than or equal to 60%. We observed improvement in fatigue, measured by the Chalder Scale (p = 0.0041), and nausea, measured by the EORTC QLQ-C30 scale (p = 0.0470), without significant weight loss (p = 0.3883) or influence on quality of life as measured by the FACIT-F questionnaire (p = 0.3375). Medications were well tolerated by most participants. No significant reduction in inflammatory parameters was observed during the treatment. The combination of U. tomentosa and P. cupana extracts is safe and has potential benefits for the control of fatigue and nausea in terminal cancer patients.
... Theophylline is abundant in tea species, but is also present in trace amounts in cocoa and coffee beans (Barnes 2013). Paullinia sp., Cola sp. and Citrus sp. also contain methylxanthines (Atawodi et al. 2007;Baumann, Schulthess, and H€ anni 1995;Kretschmar and Baumann 1999;Weckerle, Stutz, and Baumann 2003). Regarding human consumption through dietary products, caffeine and theophylline (typically at much lower amounts) may be ingested in coffee, tea, cola beverages and chocolate (Stavric 1988a), although tea contains less caffeine than coffee (Gilbert et al. 1976). ...
Article
Methylated xanthines (methylxanthines) are available from a significant number of different botanical species. They are ordinarily included in daily diet, in many extremely common beverages and foods. Caffeine, theophylline and theobromine are the main methylxanthines available from natural sources. The supposedly relatively low toxicity of methylxanthines, combined with the many beneficial effects that have been attributed to these compounds through time, generated a justified attention and a very prolific ground for dedicated scientific reports. Methylxanthines have been widely used as therapeutical tools, in an intriguing range of medicinal scopes. In fact, methylxanthines have been/were medically used as Central Nervous System stimulants, bronchodilators, coronary dilators, diuretics and anti-cancer adjuvant treatments. Other than these applications, methylxanthines have also been hinted to hold other beneficial health effects, namely regarding neurodegenerative diseases, cardioprotection, diabetes and fertility. However, it seems now consensual that toxicity concerns related to methylxanthine consumption and/or therapeutic use should not be dismissed. Taking all the knowledge and expectations on the potential of methylxanthines into account, we propose a systematic look at the past and future of methylxanthine pharmacologic applications, discussing all the promise and anticipating possible constraints. Anyways, methylxanthines will still substantiate considerable meaningful research and discussion for years to come.
... This methylxanthine is naturally present in tea leaves and in vestigial amounts in cocoa and coffee beans (Barnes, . For that reason, only few amounts of this methylxanthine are thought to be obtained through diet (Stavric, 1988 (Atawodi et al., 2007;Baumann, Schulthess, & Hänni, 1995;Kretschmar & Baumann, 1999;Weckerle, Stutz, & Baumann, 2003). Methylxanthines have been described to exert multiple physiological effects in the human body, including in the nervous (Fredholm et al., 1999;Nehlig et al., 1992;Roll, 1980), respiratory (Barnes, 2013;Dent et al., 1994) and cardiac systems (Moffat, 1986;Roll, 1980). ...
Article
Obesity is one of the most challenging health issue worldwide that has been steadily increasing in the last decades. Obesity arises from a positive energy balance in result of increased intake and decreased energy expenditure, usually due to inadequate dietary habits and a sedentary lifestyle, which results in the accumulation of excess body fat. There are few pharmacological tools to address obesity, thus calorie restriction and increased physical activity are still the cornerstone of obesity treatment. In recent years, natural products obtained from plants have been thoroughly studied to infer whether these have any potential to target obesity. Methylxanthines comprise one of those classes of compounds that are abundant in common food products consumed on a daily basis worldwide, such as coffee, chocolate, or tea. Despite caffeine is the most popular and well-studied methylxanthine, theobromine and theophylline are also abundant in humans’ diet. Notably, methylxanthines proved to stimulate lipolysis and inhibit adipogenesis, which are interesting properties that could contribute for obesity management. This review aims to discuss the most recent information concerning the promising role of methylxanthines in the modulation of adipose tissue functions, highlighting the potential of these molecules in the development of novel therapeutic approaches for obesity treatment.
... 25 The seeds of this plant have a long history of use by Amazonian tribes as a stimulant, assumed to reflect the presence of caffeine. 26,27 Paullinia cupana also includes other potentially psychoactive components, such as saponins and tannins. 25 It is commonly used as a weight-loss agent and to improve cognitive performance. ...
Article
Objective: The use of dietary supplements has increased and is associated with adverse effects. Indications for use include recreation, body image concerns, mood enhancement, or control of medical conditions. The risk of adverse effects may be enhanced if agents are used improperly. The objective of this study was to determine the frequency of abuse and misuse of 4 dietary substances among adolescents reported nationally to poison centers. Secondary outcomes included an assessment of medical outcomes, clinical effects, location of treatments provided, and treatments administered. Methods: This descriptive retrospective review assessed data concerning the use of garcinia (Garcinia cambogia), guarana (Paullinia cupana), salvia (Salvia divinorum), and St John's wort (Hypericum perforatum) among adolescents reported nationally to poison centers from 2003 to 2014. Adolescents with a singlesubstance exposure to one of the substances of interest coded as intentional abuse or misuse were included. Poison center calls for drug information or those with unrelated clinical effects were excluded. Data were collected from the National Poison Data System. Results: There were 84 cases: 7 cases of Garcinia cambogia, 28 Paullinia cupana, 23 Salvia divinorum, and 26 Hypericum perforatum. Garcinia cambogia was used more frequently by females (100% versus 0%), and Paullinia cupana and Salvia divinorum were used more frequently by males (61% versus 36% and 91% versus 9%, respectively). Abuse, driven by Salvia divinorum, was more common overall than misuse. Abuse was also more common among males than females (p <0.001). Use of these agents fluctuated over time. Overall, use trended down since 2010, except for Garcinia cambogia use. In 62 cases (73.8%), the medical outcome was minor or had no effect or was judged as nontoxic or minimally toxic. Clinical effects were most common with Paullinia cupana and Salvia divinorum. Treatment sites included emergency department (n = 33; 39.3%), non-healthcare facility (n = 24; 28.6%), admission to a health care facility (n = 8; 9.5%), and other/unknown (n = 19; 22.6%). Conclusions: Abuse and misuse of these dietary supplements was uncommon, and outcomes were mild. Further research should be performed to determine use and outcomes of abuse/misuse of other dietary supplements in this population.
... One of the most prominent examples of convergence in plants is that of caffeine biosynthesis, which appears to have evolved at least five times during flowering plant history (11). The phylogenetic distribution of caffeine, or xanthine alkaloids more generally, is highly sporadic and usually restricted to only a few species within a given genus (12,13). Caffeine accumulates in various tissues, where it may deter herbivory (14,15) or enhance pollinator memory (16). ...
Article
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Significance Convergent evolution is responsible for generating similar traits in unrelated organisms, such as wings that allow flight in birds and bats. In plants, one of the most prominent examples of convergence is that of caffeine production, which has independently evolved in numerous species. In this study, we reveal that even though the caffeine molecule is identical in the cacao, citrus, guaraná, coffee, and tea lineages, it is produced by different, previously unknown, biosynthetic pathways. Furthermore, by resurrecting extinct enzymes that ancient plants once possessed, we show that the novel pathways would have evolved rapidly because the ancestral enzymes were co-opted from previous biochemical roles to those of caffeine biosynthesis for which they were already primed.
... (like guarana), Cola sp. and Citrus sp. [33][34][35][36]. No known plant or food contains paraxanthine [32]. ...
Article
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Methylxanthines are a group of phytochemicals derived from the purine base xanthine and obtained from plant secondary metabolism. They are unobtrusively included in daily diet in common products as coffee, tea, energetic drinks, or chocolate. Caffeine is by far the most studied methylxanthine either in animal or epidemiologic studies. Theophylline and theobromine are other relevant methylxanthines also commonly available in the aforementioned sources. There are many disseminated myths about methylxanthines but there is increased scientific knowledge to discuss all the controversy and promise shown by these intriguing phytochemicals. In fact, many beneficial physiologic outcomes have been suggested for methylxanthines in areas as important and diverse as neurodegenerative and respiratory diseases, diabetes or cancer. However, there have always been toxicity concerns with methylxanthine (over)consumption and pharmacologic applications. Herein, we explore the structure-bioactivity relationships to bring light those enumerated effects. The potential shown by methylxanthines in such a wide range of conditions should substantiate many other scientific endeavors that may highlight their adequacy as adjuvant therapy agents and may contribute to the advent of functional foods. Newly designed targeted molecules based on methylxanthine structure may originate more specific and effective outcomes.
... Guaraná seeds contain high amounts of methylxanthines and tannins, as well as saponins, starch, polysaccharides, pigments, fats and choline (Dalonso and Petkowicz, 2012;Sousa et al., 2010;Yamaguti-Sasaki et al., 2007;Ushirobira et al., 2007;Edwards et al., 2005;Sombra et al., 2005;Bruneton et al., 1999;Meurer-Grimes et al., 1998;Seidemann, 1998;Carlson and Thompson, 1998;Mattei et al., 1998;Nazaré 1988;Baumann et al., 1995;Henman, 1982 (Nazaré, 1998;Medical, 2000). 5 times higher than that found in a Coffea arabica bean ( Figure 1) (Weckerle et al., 2003;Pagliarussi et al., 2002;Baumann et al., 1995). Tannins are classified into condensed tannins, based on a flavonoid framework, and hydrolysable tannins, which are essentially galloyl esters of glucose. ...
... In order to identify caffeine-containing ingredients on product labels and product websites, a literature search was conducted, and the National Health and Nutrition Evaluation Survey (NHANES 2001-02) dietary supplement data files [18] were reviewed. Table 1 lists the terms identified from these searches, which are commonly used on labels for caffeine-containing ingredients in dietary supplement products [19,20]. ...
Article
As part of a study initiating the development of an analytically validated Dietary Supplement Ingredient Database (DSID) in the United States (US), a selection of dietary supplement products were analyzed for their caffeine content. Products sold as tablets, caplets, or capsules and listing at least one caffeine-containing ingredient (including botanicals such as guarana, yerba mate, kola nut, and green tea extract) on the label were selected for analysis based on market share information. Two or three lots of each product were purchased and analyzed using high-pressure liquid chromatography (HPLC). Each analytical run included one or two National Institute of Standards and Technology (NIST) Standard Reference Materials (SRMs) and two products in duplicate. Caffeine intake per serving and per day was calculated using the maximum recommendations on each product label. Laboratory analysis for 53 products showed product means ranging from 1 to 829 mg caffeine/day. For products with a label amount for comparison (n=28), 89% (n=25) of the products had analytically based caffeine levels/day of between −16% and +16% of the claimed levels. Lot-to-lot variability (n=2 or 3) for caffeine in most products (72%) was less than 10%.
... The pericarp contains lower levels of purine alkaloids, but theobromine (0.2%) was the main component together with trace amounts of caffeine (0.02%) and theophylline (0.001%). Weckerle et al. (41) screened 34 species of Paullinia and related genera for purine alkaloids; only three species, P. cupana, P. yoco, and P. pachycarpa, were positive. The distribution of purine alkaloids in P. pachycarpa was found to be restricted to theobromine, in the stem, leaves, and flowers. ...
Article
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Methylxanthines and methyluric acids are secondary metabolites derived from purine nucleotides and are known collectively as purine alkaloids. The present review begins by summarizing the distribution of these compounds in the plant kingdom, and then provides an up-to-date account of the biosynthesis of purine alkaloids. The diversity of biosynthesis and accumulation between species and between tissues of different age is considered. We also discuss the physiological function of these purine alkaloids in plants and the biotechnology for creating caffeine-free plants.
... Caffeine consumed in a beverage is absorbed by the small intestine within 45 min of ingestion [28], and previous data show no difference in absorption rates between pure caffeine and caffeine from guaraná [29]. However, guaraná also contains the methylxanthines theophylline and theobromine [30], as well as saponins and polyphenols, including tannins, catechins, and epicatechins [31], and differences in the behavioral effects of caffeine and guaraná have been noted [32]. In addition, a recent meta-analysis reported that although both caffeine and tea catechin-caffeine mixtures increased energy expenditure, increases to fat oxidation only reached significance following the mixture [33]. ...
Article
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Exercise undertaken in a fasted state can lead to higher post-exercise mental fatigue. The administration of a vitamin and mineral complex with guaraná (MVM + G) has been shown to attenuate mental fatigue and improve performance during cognitively demanding tasks. This placebo-controlled, double-blind, randomized, balanced cross-over study examined the effect of MVM + G consumed prior to morning exercise on cognitive performance, affect, exertion, and substrate metabolism. Forty active males (age 21.4 ± 3.0 year; body mass index (BMI) 24.0 ± 2.4 kg/m2; maximal oxygen consumption (V̇O2max) 57.6 ± 7.3 mL/min/kg) completed two main trials, consuming either MVM + G or placebo prior to a 30-min run at 60% V̇O2max. Supplementation prior to exercise led to a small but significant reduction in Rating of Perceived Exertion (RPE) during exercise compared to the placebo. The MVM + G combination also led to significantly increased accuracy of numeric working memory and increased speed of picture recognition, compared to the placebo. There were no significant effects of supplementation on any other cognitive or mood measures or on substrate metabolism during exercise. These findings demonstrate that consuming a vitamin and mineral complex containing guaraná, prior to exercise, can positively impact subsequent memory performance and reduce perceived exertion during a moderate-intensity run in active males.
... TheS apindaceae species have also been intensely studied from ac hemistry perspective.D ifferent metabolites have been investigated, such as alkaloids [ 15], cyanogenicg lycosides [16], and cyanolipids [ 17 -19].T he fatty-acid compositions of different species have also been analyzed [20 -23].F atty acids compose as tructurally diverse group of molecules that biosyntheticallyoriginate from the acetyl CoA pathway [24]. Despite diverse structures,certain fatty acids have alimited distribution in nature, and otherfatty acids presentanuncommonchemical structure.Thus,fatty acids are an important tool for systematic studies,due to their chemotaxonomic potential. ...
Article
Circumscriptions for the Sapindaceae family and its infrafamilial relationships have been widely discussed. Certain groups are highly morphologically similar; thus, it is difficult to identify certain taxa. DNA Analyses have also indicated complex phylogenetic relationships, and it is difficult to relate such analyses to morphological data. Given the above concerns, this study aimed to investigate the fatty-acid profiles of the seed oils of 16 Sapindaceae species belonging to five tribes and to evaluate their potential chemotaxonomic significance. In total, eleven fatty acids were identified, and eicosenoic acid predominated in nine species. Multivariate analyses (principal component and cluster analyses) of the fatty-acid profiles of the seed oils allowed to separate them in two major clusters. The first cluster, characterized by oils with high eicosenoic acid levels, included all species belonging to the Paullinieae tribe (Cardiospermum, Paullinia, and Serjania species). In the second main cluster, the chemical similarity of the oils was lower, and the species belonged to different tribes. Nevertheless, the tree investigated Allophylus species (Thouinieae tribe) constituted a separate subcluster. Thus, the results showed that the fatty-acid composition of the seed oils of Sapindaceae species provide chemotaxonomic support for the separation of the Paullinieae tribe from the other tribes studied. Copyright © 2015 Verlag Helvetica Chimica Acta AG, Zürich.
... While the caffeine in guarana likely works by these mechanisms, other constituents possibly function using different pathways. In addition to caffeine, guarana seeds are known to harbor a number of other possible stimulants such as catachins, tannins and other alkaloids such as theophylline and theobromine [19,22,30,60]. At present, little information is available favoring one of these ingredients over the others. ...
Article
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The stimulant effect of energy drinks is primarily attributed to the caffeine they contain. Many energy drinks also contain other ingredients that might enhance the tonic effects of these caffeinated beverages. One of these additives is guarana. Guarana is a climbing plant native to the Amazon whose seeds contain approximately four times the amount of caffeine found in coffee beans. The mix of other natural chemicals contained in guarana seeds is thought to heighten the stimulant effects of guarana over caffeine alone. Yet, despite the growing use of guarana as an additive in energy drinks, and a burgeoning market for it as a nutritional supplement, the science examining guarana and how it affects other dietary ingredients is lacking. To appreciate the stimulant effects of guarana and other natural products, a straightforward model to investigate their physiological properties is needed. The planarian provides such a system. The locomotor activity and convulsive response of planarians with substance exposure has been shown to provide an excellent system to measure the effects of drug stimulation, addiction and withdrawal. To gauge the stimulant effects of guarana we studied how it altered the locomotor activity of the planarian species Dugesia tigrina. We report evidence that guarana seeds provide additional stimulation over caffeine alone, and document the changes to this stimulation in the context of both caffeine and glucose.
... Once the complete maturity is reached, the "white of the eye", botanically an aril of mealy consistency, is chosen. Then it is rubbed of manually and the seeds are roasted to facility the removal of the glossy, tough and dark brow seed coat (pericarp) and the later grinding of the kernels in a hardwood mortar [10][11][12]. ...
Article
The GC-MS analysis of phenolic compounds present in guarana (Paullinia cupana), an important product of the Amazonian forest consumed in supplements or in soft drinks has been the subject of study. The therapeutic properties and possible protective effects reported for guarana and derivative products could be associated with the antioxidant activity of their phenolics content. The purpose of this study is i) to provide molecular structural information about the composition of guarana in phenolics; ii) to ascertain the effect of solvent type on the extraction procedure; and iii) to determine the antioxidant activity of powders, pericarp, pulp seeds, capsules and bar from Paullinia cupana, as oxygen radical absorbance capacity with fluorescein (ORACFL). Three more phenolic compounds, Quercetin, (+)-Catechin and (- )-Epicatechin have been identified in this report as trimethylsilyl (TMS) derivatives. The amount of total phenolics found in plant materials containing guarana varied from 25.10 to 124.99 mg of gallic acid/g dry sample whereas that the antioxidant activity ranged from 441.5 to 1468.3 μmol TEAC/g dry sample. A high correlation was found between the estimated phenolic contents and the TEAC values (r = 0.937, P< 0.01) for all the types of guarana samples tested.
... Guaraná, a low-growing bush-type plant, is the richest vegetable sours of caffine (Mehr et al., 1996;Weckerle et al., 2003). The seeds of this plant also contain theophylline, theobromine, xanthine derivatives and tannins and also catechin, epicatechin and proanthocyanidins (Majhenic et al., 2007). ...
Article
In the present study, fruits extracts (Paullinia cupana K. & Libidibia ferrea M.-guaraná & jucá, respectively) of the Amazon Region were tested for antifungal and antimycotoxigenic activities against Aspergillus parasiticus using the agar dilution method. The treatments utilized were at three different concentrations (1.08, 1.62 and 3.24%). The effect on both extracts on growth diameter of fungal colony was time and concentration dependent. No treatment completely inhibited fungi growth, however A. parasiticus was significantly reduced by the treatments when compared to the control group. The production of AFB1, AFB2, AFG1 and AFG2 by A. parasiticus grown on guaraná and jucá extracts treatment was significantly smaller when compared to controls. A. parasiticus strain produced aflatoxins in all concentrations when grown on guaraná extracts medium treated and different of that observed when on jucá's treated extracts.
... These effects are derived from chemical compounds present in the guarana seeds, particularly the xanthines, such as caffeine, theophylline and theobromine (Belliardo et al., 1985). The largest fraction of caffeine is located in different parts of the seed: the seed kernel (embryo with bulky cotyledons) and the seed coat (testa), that are high in caffeine content (4.28 and 1.64%, respectively) (Weckerle et al., 2003). ...
... Once the complete maturity is reached, the "white of the eye", botanically an aril of mealy consistency, is chosen. Then it is rubbed of manually and the seeds are roasted to facility the removal of the glossy, tough and dark brow seed coat (pericarp) and the later grinding of the kernels in a hardwood mortar [10][11][12]. ...
Article
Full-text available
The GC-MS analysis of phenolic compounds present in guarana (Paullinia cupana), an important product of the Amazonian forest consumed in supplements or in soft drinks has been the subject of study. The therapeutic properties and possible protective effects reported for guarana and derivative products could be associated with the antioxidant activity of their phenolics content. The purpose of this study is i) to provide molecular structural information about the composition of guarana in phenolics; ii) to ascertain the effect of solvent type on the extraction procedure; and iii) to determine the antioxidant activity of powders, pericarp, pulp seeds, capsules and bar from Paullinia cupana, as oxygen radical absorbance capacity with fluorescein (ORAC FL). Three more phenolic compounds, Quercetin, (+)-Catechin and (-)-Epicatechin have been identified in this report as trimethylsilyl (TMS) derivatives. The amount of total phenolics found in plant materials containing guarana varied from 25.10 to 124.99 mg of gallic acid/g dry sample whereas that the antioxidant activity ranged from 441.5 to 1468.3 μmol TEAC/g dry sample. A high correlation was found between the estimated phenolic contents and the TEAC values (r = 0.937, P< 0.01) for all the types of guarana samples tested.
... Paullinia cupana Kunth stimulant Seeds Indians living in Brazilian Amazon [20] purine alkaloids [577,578,579,580,581] Talisia cerasina (Benth.) Radlk. ...
Article
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Ethnopharmacological research investigates the plants and other medicinal and toxic substances utilized by different traditional populations. One approach in this field is a literature search of the available publications on medicinal plants. The purpose of the current study was to select plants with psychoactive effects described in a Brazilian literary work written by Pio Correa in 1926. Those mentioned plants were classified in accordance with their indications for use as stimulants and depressors of the central nervous system. For the phytochemical study herein, we researched these species via a database search, and all the obtained information was compiled into a new database to analyze possible correlations between the chemical compounds and the psychoactive categories. Of the 813 plants searched in the literary work, 104 presented chemical data in the scientific periodicals consulted. Seventy-five of them belong to the stimulant category, while 31 are depressors and two of them belong to both categories. Phenols and flavonoids were the main compounds observed in plants of both categories, though at different frequencies. Monoterpenes (29.9%) and sesquiterpenes (28.6%) were also observed in plants from the stimulant category, while 25.8% of plants from the depressor category were comprised of carotenoids and 22.6% of steroids. The main specific compounds were identified as ferulic acid, α-pinene, limonene, α-humulene and kaempferol among the stimulant plants. Otherwise, in depressor plants were characterized caffeic acid, kaempferol, quercetin, β-carotene, physalins and withanolides as specific compounds. The association between ethnopharmacological and chemotaxonomic data, as presented in this study, could support plant selection in further investigations by research groups whose studies focus on psychoactive plants as potential therapeutics.
... Beginning 30-minute postdose, assessment on a cognitive demand battery (CDB) comprising repeated assessments of serial subtraction, which require repeated subtraction of three or seven starting from a random three-digit number, and a rapid visual information processing (RVIP) tasks revealed significantly greater accuracy and reduced response time on the RVIP task after treatment with the multivitamin and mineral combination when compared to placebo. 4 As the active treatment in the study by Kennedy et al. 4 also contained guaraná extract, further research is required in order to properly differentiate the potential acute effects of single-dose multivitamin and mineral administration from that of guaraná. Guaraná (Paullinia cupana), found in the central Amazon, contains caffeine and other purine alkaloids, 5 saponins, tannins, and catechins. 6 Given these numerous potentially nootropic constituents, it is perhaps unsurprising that guaraná in isolation has been found to have acute effects on cognition. ...
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Objectives: Relatively few studies have explored the possibility of acute cognitive effects of multivitamin ingestion. This report explores the acute brain electrophysiological changes associated with multivitamin and mineral supplementation, with and without guaraná, using the steady-state visually evoked potential (SSVEP). Methods: Based on the known SSVEP correlates of A-X continuous performance task (CPT) performance, and sensitivity to acute psychopharmacological manipulations, the A-X CPT was adopted as a task paradigm to explore treatment-related neurophysiological changes in attentional processing. Twenty healthy non-smoking adults aged 21-39 years (mean age = 28.35 years, SD = 5.52) took part in this double-blind, placebo-controlled, randomized, balanced crossover design study. Results: The study demonstrated both transient and tonic changes in the SSVEP response during completion of the A-X CPT following multivitamin and mineral treatment both with and without guaraná. Transient changes in SSVEP response in prefrontal regions were observed after a single dose of a multivitamin and mineral preparation indicative of enhanced activity within brain regions engaged by the attentional demands of the task. This pattern of change in frontal regions was correlated with improved behavioural performance after treatment with the multivitamin and mineral combination. Where tonic shifts in SSVEP response were investigated, multivitamin and mineral treatment was associated with a pattern of increased inhibition across posterior regions, with enhanced excitatory processing in prefrontal regions. In contrast, multivitamin and mineral treatment with additional guaraná showed a tonic shift towards greater excitatory processes after a single treatment, consistent with the caffeine content of this treatment. Discussion: While preliminary in nature, these findings suggest a single multivitamin/mineral dose is sufficient to impact on functional brain activity in task-related brain regions.
Article
Extraction of caffeine from guarana seeds was studied, comparing conventional extraction (CE) and ultrasound-assisted extraction (UAE). Preliminary studies permitted the selection of operating conditions for kinetics studies of both processes (water solvent, 10:1 mL/g liquid-solid ratio). UAE enabled strong enhancement of caffeine yields and process kinetics compared to CE at room temperature. At higher temperature (50 and 70 °C), the advantage of UAE over CE was still clear for extraction kinetics, but not for maximal extraction yield. Performing Life Cycle Assessment of both processes permitted to highlight ultrasound assistance ability to reduce extraction duration (up to 4.9 times), energy consumption (up to 6.2 times) and environmental impacts (more than twice for some impact categories) compared to CE at the same studied temperature. Environmental impacts of CE and UAE processes were studied in more detail using three different functional units. It contributed to a better knowledge of extraction process of caffeine from guarana seeds and allowed selecting the operating conditions maximizing benefits provided by ultrasound assistance. The environmental gains of UAE over CE at maximal temperature were relatively small when targeting a caffeine extraction yield close to the maximal attainable (at this temperature), but increased strongly for lower target yields.
Chapter
Alkaloids are characterized by containing a nitrogen atom, usually within a heterocyclic ring. Many are derived from aromatic amino acids, but for some also other amino acids, ornithine, spermidine, xanthosine and the terpenoids are the basic building blocks. Many well-known compounds such as caffeine, nicotine and atropine fall into this group. The major groups are terpenoid indole alkaloids and benzylisoquinoline alkaloids, but also in many other pathways, toxic or psychedelic alkaloids can be synthesized. The biosynthesis pathway is often spread over different cell types and is very compartmentalized within the cells to avoid toxicity for the plant.
Article
Brazil is the major producer of guarana, a stimulant largely consumed worldwide. Interest in health benefits of its consumption has increased the inclusion of guarana extracts in industry applications, providing dietary supplements, medicines, cosmetics, and functional foods. Major bioactive constituents of guarana popularly known are methylxanthines and catechins. Methylxanthines, particularly caffeine, are associated with improvement in cognitive function and energy-expenditure increasing. Catechins are phenolic constituents reported with anticancer and antimicrobial effects. The application of combined processes to enhance the methylxanthines and polyphenols profile and subsequent valorization of guarana waste fraction is an attractive alternative for the obtaining of value-added products. In this context, this review provides a literature survey and perspectives on health aspects and technological potential on the application of methylxanthines and polyphenols from guarana extracts for the development of functional foods with maximized bioactive constituents and subsequently, health benefits.
Article
Theophylline, one of the most commonly used bronchodilators and respiratory stimulators for the treatment of acute and chronic asthmatic conditions, can cause permanent neurological damage through chronic or excessive ingestion. In this work, DFT calculation was performed to identify the metabolic mechanisms of theophylline by cytochrome P450 (CYP450) monooxygenase. Two main metabolic pathways were investigated, namely, N1- (path A) and N3- (path B) demethylations, which proceeded through N-methyl hydroxylation followed by the decomposition of the generated carbinolamine species. N-methyl hydroxylation involved a hydrogen atom transfer (HAT) mechanism, which can be generalized as the N-demethylation mechanism of xanthine derivatives. The energy gap between the low-spin double state (LS) and the high-spin quartet state (HS) was low (<1 kcal mol-1), indicating a two-state reactivity (TSR) mechanism. The generated carbinolamine species preferred to decompose through the adjacent heteroatom (O6 for path A and O2 for path B) mediated mechanism. Path B was kinetically more feasible than path A attributed to its relatively lower activation energy. 1-Methylxanthine therefore was the energetically favorable metabolite of theophylline. The observations obtained in the work were in agreement with the experimental observation, which can offer important implications for further pharmacological and clinic studies.
Chapter
Caffeine is one of the purine alkaloids that are synthesized in larger quantities in a limited number of plant species in the genera Camellia, Coffea, Theobroma, Paullinia, Ilex, and Cola. The main caffeine biosynthetic pathway is as follows: xanthosine → 7-methylxanthosine → 7-methylxanthine → theobromine → caffeine. This pathway appears to be universal in purine alkaloid-containing plants. The identification of caffeine synthase from Camellia sinensis, which catalyzes the last two methylation steps in caffeine biosynthesis, has led to the subsequent isolation of many functionally related N-methyltransferase genes. These N-methyltransferases and the related genes involved in caffeine biosynthesis are described.
Chapter
Caffeine is a xanthine alkaloid found in non-alcoholic beverages such as tea, coffee, and cocoa. It was discovered in tea and coffee in the 1820s, but it was not until 2000 that details of molecular events associated with caffeine biosynthesis began to be unraveled. Reviewed are the occurrence of xanthine alkaloids in the plant kingdom and the elucidation of the caffeine biosynthesis pathway, providing details of the N-methyltransferases, belonging to the motif B′ methyltransferase family, which catalyze three steps in the four-step pathway leading from xanthosine to caffeine. Pathways for the metabolism and degradation of xanthine alkaloids are discussed, although as yet the genes and enzymes involved have not been isolated. This chapter also considers the in planta role of caffeine in chemical defense that has been demonstrated using transgenic caffeine-forming tobacco and chrysanthemum plants, which are resistant to attack by pathogens and herbivores. Finally, future research is considered that might lead to the production of naturally decaffeinated beverages and agricultural crops that contain elevated levels of “natural” pesticides.
Chapter
There is growing evidence that certain plants have evolved to contain bioactive compounds that can modulate behaviour, including cognitive performance. This chapter briefly summarises the evidence pertaining to selected herbal extracts ginseng, Ginkgo biloba, Salvia, L-theanine, green tea catechins, Bacopa and guaraná. The focus is on evidence from well-controlled human trials examining the acute effects of supplementation in healthy adults. Although not discussed here, it should be noted that there is emerging evidence that some herbal extracts may also have chronic cognitive benefits in various clinical and non-clinical populations.
Chapter
This chapter describes four-membered heterocyclic rings of azetidine, azetines, oxetanes, and dithiethanes, and their fused derivatives. It deals with biosynthetic studies conducted on the natural polyoxins A, F, H, I, and K, all bearing the four-membered ring of polyoximic acid (POIA). The nocardicins are a family of monocyclic β-lactam antibiotics (BLAs). The mode of action of nocardicins is the same as that of BLAs: they inhibit the synthesis of the peptidoglycan layer of bacterial cell walls. However, a detailed mode of action of BLAs is treated in the chapter. The chapter provides information limited to the isolation, mode of action, and the biosynthetic route to penicillin G and cephalosporin C and closely related compounds. Finally, it discusses biosynthesis of thiotropocin and tropodithietic acid (TDA). The genetic data on the antibiotic confirmed the biosynthetic pathway proposed through biochemical studies and is outlined.
Article
The chapter summarises the evidence pertaining to the biobehavioural effects of selected herbal extracts, concentrating on evidence from well-controlled human trials. The focus is on cognition enhancement but will include some relevant material on modulation of mood. There is good evidence that certain extracts have cognition-enhancing properties. These include extracts of Ginkgo, Ginseng, Salvia, Guaraná, Lemon balm, Bacopa and others. In the domain of mood Lemon balm has consistently been shown to have a calming effect. Evidence for other herbals is less clear although cocoa polyphenols may have anti-fatigue effects. One constant challenge for the psychopharmacology of herbal extracts is the use of standardised extracts and the use of multiple extracts in some medicinal systems. New technologies used to meet these challenges will be discussed briefly.
Article
Chemical isolation of a semi-purified extract from the seeds of guaraná, Paullinia cupana H.B.K. var. sorbilis (Mart.) Ducke, resulted in the identification of caffeine, catechin, epicatechin, and procyanidins B2, B3 and B4. The antibacterial activity of the extracts and isolated substances was evaluated in vitro against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa. Even in concentrations up to 1000 μg/ml, there was no activity against these microorganisms.
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Fruits of the plant were air dried for several days and cut into small pieces, which were subjected to oven dried for 24 hours at 45-50°C to effect further chopping. Cold methanol extract of fruits were subjected to acid-base treatment to separate the alkaloids. The treated extract was subjected to column chromatography to isolate the pure compound. The xanthine alkaloid, 1, 3, 7-trimethyl-1H-purine-2, 6 (3H, 7H)-dione, caffeine (compound 1) and also p-anisaldehyde (compound 2) were isolated from the column fraction of this 'alkaloid containing residue' by elution with ethyl acetate/10% methanol and ethyl acetate/50-100% methanol, respectively. The isolated pure compounds were identified by extensive spectral (1 H-NMR, 13 C-NMR, DEPT, HMBC, HSQC, Mass) data analysis. Greshoff isolated an alkaloid, pithecolobin from the bark, which is saponin like in its action. Wehmer stated that the seeds also contain pithecolobin. In the Philippines, a decoction of the inner bark (fresh cambium) and the fresh leaves of this tree is used in diarrhea. All these above mentioned study lead us to work on it. INTRODUCTION: Enterolobium saman (Jacq.) Prain (Leguminosae, subfamily Mimosoideae) is a large tree of 20 to 25 meters high with characteristic umbrella-shapped canopy, native to Latin America where is commonly known as "Rain-tree" and also available in Bangladesh with the bengali name of "Koroi" 1 . The fresh leaves of the plants are used in diarrhea 1 .
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The allocation of purine alkaloids within citrus flowers was studied and found to be linked to anthesis, with 99% of the total flower caffeine confined to the androecium. The main alkaloid is caffeine accompanied by considerable (up to 30% of caffeine) concentrations of theophylline. In the anther, these purine alkaloids reach altogether a concentration of 0.9% dry wt which is close to the caffeine content of the Arabica coffee bean. The pollen alkaloid concentration is in the same range. Much lower but still marked concentrations were found in the nectar. A considerable breakdown of alkaloids during honey production is assumed. The biological significance of this particular secondary compound allocation as well as possible effects on the key pollinator, the honey-bee, are discussed.
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Most commercial products for snail and slug control contain either metaldehyde or methiocarb as the active ingredient, the residues of which are not permitted in food crops in the United States. We have discovered that solutions of caffeine are effective in killing or repelling slugs and snails when applied to foliage or the growing medium of plants. Because caffeine is a natural product and is classified by the US Food and Drug Administration as a GRAS (‘generally recognized as safe’) compound, it has potential as an environmentally acceptable alternative toxicant for the control of slugs and snails on food crops. While field-testing caffeine as a toxicant against an introduced frog pest that infests potted plants in Hawaii, we discovered that large slugs were killed by spray applications containing 1–2% caffeine. To test whether caffeine solutions could be used to remove or kill large slugs that attack potted plants, we allowed Veronicella cubensis (Pfeiffer) to bury themselves in the soil in the pots, and then thoroughly wetted the soil with a 2% caffeine solution. After 3.5 h, only 25% of the slugs remained in the soil; after 48 h, all slugs had left the soil and 92% were dead.
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Coffea seeds accumulate purine alkaloids (PuAs) and chlorogenic acids (CGAs) in a correlated manner: a high concentration of PuAs (mostly caffeine) accompanies a considerable accumulation of CGAs (mostly 5-caffeoylquinic acid; 5-CQA) and vice versa. Since caffeine and related PuAs per se freely penetrate cell-, tissue-, and organ-related barriers, we suggested that the physico-chemically well-characterized PuA-CGA complex is the crucial mechanism of PuA sequestration in these plant species and therefore the cause of the above-mentioned correlation. Suspension-cultured coffee (C. arabica) cells produce the complex partners in readily measurable concentrations, and were therefore an ideal system for investigating the in situ significance of complex formation. The partition of caffeine between cells and medium was studied in relation to the concentration of 5-CQA which, like the complex, is confined to the vacuole. Induction of the phenolic pathway was monitored by measuring PAL activity. To create concentration ranges of the complex partners as wide as possible, the cultures were subjected to various conditions such as the addition of a photoperiod or methyljasmonate (both stimulating secondary product formation), 2-aminoindan-2-phosphonic acid (2-AIP) (a most potent inhibitor of PAL), and exogenous caffeine. In all experimental sets, compartmentation of caffeine (and also that of theobromine) was highly correlated to the concentration of 5-CQA. In addition, inhibition of 5-CQA synthesis by 2-AIP consequently led to a reduction of caffeine biosynthesis whereas exogenous caffeine evoked the synthesis of the phenolic counterpart (5-CQA), this indicating a regulatory connection between the complex partners. When the cell cultures were transferred from 25° to 10°, or to 37°, caffeine shifted rapidly, as expected, from the medium into the cells or vice versa. Moreover, a modelling study showed that complex formation almost fully explains the measured degree of compartmentation. Similarly, in tissues and organs of the intact coffee plant the driving force of caffeine compartmentation was also shown to be defined by the physical chemistry of the complex. Finally, all caffeine-containing plants may have evolved basically one common strategy to sequester PuAs, i.e. the vacuolar allocation of high concentrations of one or several complexing phenols.
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The fruit of the Amazonian guaraná liana (Paullinia cupana) looks like a human eye, and undoubtedly shows the ‘bird dispersal syndrome’. The seeds were reported to be ingested by large birds such as toucans and guans. We determined the purine alkaloid content of the various fruit and seed parts. The two aspects of defence and dispersal are reflected in the differential seed alkaloid distribution: the seed kernel (embryo with bulky cotyledons) and the seed coat (testa) accumulate much caffeine, i.e. 4.28 and 1.64%, respectively, whereas the ‘white of the eye’, the aril, is virtually alkaloid-free, but contains glucose, fructose and sucrose up to almost 70% of aril dry weight. Furthermore, the aril is strongly hygroscopic and it is suggested that it extends germination power by preventing seed desiccation. Experiments simulating pH and temperature conditions in the avian stomachs showed rapid desintegration of the aril and no caffeine release by the intact seed at pH 4.5 (crop) during the first 30 min of ‘digestion’. Only a tiny fraction (between 0.025 and 0.07%) of total seed caffeine left the intact seed after 60 min at pH 4.5 or during the incubation at pH 2.3 (gizzard), indicating the presence of a very powerful diffusion barrier in the seed coat which at least theoretically should prevent intoxication of the dispersing bird even after an assumed foraging bout of 50 seeds. The cracked seed, however, releases a considerable fraction of its caffeine, considered harmful to destructive birds, if a few seeds were processed in this way. Absence of caffeine in the aril could well be the result of a ‘secondary’ degradation during maturation, analogous to hypoglycin A in the aril of the closely related sapindaceous Blighia sapida.
Article
The aim of this research was to examine whether the de novo pathway of purine nucleotide biosynthesis directly contributes to the biosynthesis of caffeine in tea leaves. The 15N atom from [15N] glycine was incorporated into theobromine and caffeine, and its incorporation was markedly reduced by azaserine and aminopterin, known inhibitors of purine biosynthesis de novo. The radioactivity from [2-14C] 5-aminoimidazole-4-carboxamide ribonucleoside (AICAR), a precursor of 5-aminoimidazole-4-carboxamide ribonucleotide (ZMP), was also incorporated into theobromine and caffeine. Pulse-chase experiments with [15N]glycine and [2-14C]AICAR suggested that theobromine is the immediate precursor of caffeine. Incorporation of radioactivity from [2-14C]AICAR into purine alkaloids was not influenced by treatment with coformycin, an inhibitor of plant AMP deaminase. The velocity of the incorporation of radioactivity into theobromine from [8-14C]inosine, an immediate precursor ofiMP, was faster than that from [8-14C] adenine, a precursor of AMP. These results suggest that most of the purine alkaloids are produced from newly produced IMP by the de novo pathway for purine nucleotide biosynthesis. Although it is difficult to exclude the participation of caffeine biosynthetic pathways from preformed purines, the contribution of the de novo pathway to caffeine biosynthesis seems to be important, especially in young tea leaves in which a very rapid net accumulation of purine alkaloids is observed.
Article
In buds and emergent leaflets of Coffea arabica formation of the purine alkaloids caffeine and theobromine was studied with the aim of characterizing the chemical defence strategy of a tissue with a high risk of predation. As long as the leaflets are fully covered by a resin layer and by two stipules, their alkaloid content varies between 1 and 3% dry wt. With leaflet emergence, the alkaloid formation increases and the variation decreases. Maximum content of about 4% is reached when the leaflets are fully open. In the subsequent developmental period alkaloid content decreases. A comparison between the investment in alkaloid formation with that in primary metabolic processes demonstrates that chemical defence is costly: influx of carbon atoms into caffeine is 15% of that into respiration. A defence strategy which is based on an antagonism between mechanical and chemical protection is discussed.
Article
The seeds and leaves of nine Herrania and 11 Theobroma species were examined for their purine alkaloid content. Tetramethyl urate was the principal purine alkaloid present. Caffeine and theobromine, when detected, were mainly trace components. Theophylline was not detected in any of the samples.
Article
Leaves from a dark air-cured tobacco variety (Ky 171) were divided into 41 defined leaf segments. All samples were analyzed for nitrate nitrogen, nitrite nitrogen, nicotine, myosmine, nornicotine, anabasine, anatabine, N'-nitrosonornicotine (NNN), N'-nitrosoanatabine (NAT), and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). Nitrite concentration was highest at the base of the leaf and decreased toward the tip of the leaf. Concentration of alkaloids was lowest at the base and tip of the leaf and greatest at the periphery of the leaf and decreased toward the tip of the leaf. Individual nitrosamines were lowest at the tip and the periphery of the leaf. Midvein contained lowest concentrations of NNN, NNK, and NAT at two-thirds length of the leaf and was highest at the base of the leaf. There appeared to be a better relationship between nitrite nitrogen and tobacco-specific nitrosamines than there was with alkaloid content in the leaf.
Article
The content of the total tannins, proanthocyanidins and prototannins in the seeds of guarana, Paullinia cupana var. sorbilis HKB (Sapindaceae) was studied. A total tannin content of 12.1% dry matter was found in air dried samples. Reversed-phase high-performance liquid chromatography (RP-HPLC) analysis resulted in 6.0% (+)-catechin and 3.8% (–)-epicatechin on an average. Hydrolysable tannins were not detectable. The results for one of two analyzed ground samples from the Brazilian market were substantially lowered. It is concluded that this product was adulterated with another no tannin containing material.Der Gehalt an Gesamtgerbstoffen, Proanthocyanidinen und Prototanninen im Samen von Guarana,Paullinia cupana var.sorbilis HKB (Sapindaceae), wurde untersucht. In lufttrockenen Samen wurde ein Gesamttanningehalt von 12,1% i. T. gefunden, die Proanthocyanidin-Bestimmung ergab einen Gehalt von 10,7%; mittels RP-HPLC-Analyse wurden 6,0% an (+)-Catechin und 3,8% (–)-Epicatechin gefunden. Hydrolysierbare Tannine waren nicht nachweisbar. Bei einer von zwei untersuchten gemahlenen Proben des brasilianischen Handels waren alle Analysenwerte erheblich erniedrigt, was auf eine Streckung des Produkts mit nicht gerbstoffhaltigem Material schlieen lt.
Article
Seasonal variations in the metabolic fate of adenine nucleotides prelabelled with [8-14C]adenine were examined in leaf disks prepared at one-month intervals, over the course of one year, from the shoots of tea plants (Camellia sinensis L. cv Yabukita) which were growing under natural field conditions. Incorporation of radioactivity into nucleic acids and catabolites of purine nucleotides was found throughout the experimental period, but incorporation into theobromine and caffeine was found only in the young leaves harvested from April to June. Methylation of xanthosine, 7-methylxanthine and theobromine was catalysed by gel-filtered leaf extracts from young shoots (April to June), but the reactions could not be detected in extracts from leaves in which no synthesis of caffeine was observed in vivo. By contrast, the activity of 5-phosphoribosyl-1-pyrophosphate synthetase was still found in leaves harvested in July and August.
Article
Guaraná is considered an ideal crop for supplementing the incomes of small peasant farmers in the Amazon basin. A fast-growing perennial, guaraná can be planted in the midst of manioc crops, allowing the formation of extensive orchards in the place of regenerating scrub once the manioc has been harvested. Traditional forms of guaraná agriculture practised by the Saterê-Mawé Indians compare favourably with the plantation system favoured by government agronomists. Indigenous techniques of hand-processing guaraná are also shown to produce better quality in the finished product than those practices adopted by industrial concerns. A detailed comparison of two systems of production show the Indians' implicit concern to avoid oxidization of the phenolic compounds in the seed, since this leads to the guaraná becoming dark in colour, bitter in taste, and irritating to the gastrointestinal tract. The short-term medicinal effects of guaraná are commonly thought to result from a high content of caffeine and associated alkaloids, as well as from considerable amounts of tannin. Future research may well show that various saponins also play an important part in the drug's pharmacology, particularly with regard to its long-term influence as a general tonic and prophylactic.
Article
Theacrine (1,3,7,9-tetramethyluric acid) and caffeine were the major purine alkaloids in the leaves of an unusual Chinese tea known as kucha (Camellia assamica var. kucha). Endogenous levels of theacrine and caffeine in expanding buds and young leaves were ca. 2.8 and 0.6-2.7% of the dry wt, respectively, but the concentrations were lower in the mature leaves. Radioactivity from S-adenosyl-L-[methyl-14C]methionine was incorporated into theacrine as well as theobromine and caffeine by leaf disks of kucha, indicating that S-adenosyl-L-methionine acts as the methyl donor not only for caffeine biosynthesis but also for theacrine production. [8-14C]Caffeine was converted to theacrine by kucha leaves with highest incorporation occurring in expanding buds. When [8-14C]adenosine, the most effective purine precursor for caffeine biosynthesis in tea (Camellia sinensis), was incubated with young kucha leaves for 24 h, up to 1% of total radioactivity was recovered in theacrine. However, pulse-chase experiments with [8-14C]adenosine demonstrated much more extensive incorporation of label into caffeine than theacrine, possibly because of dilution of [14C]caffeine produced by the large endogenous caffeine pool. These results indicate that in kucha leaves theacrine is synthesized from caffeine in what is probably a three-step pathway with 1,3,7-methyluric acid acting an intermediate. This is a first demonstration that theacrine is synthesized from adenosine via caffeine.
Sur la liane Yocco et sur la pre´sencepre´sence de Cafeíne dans les Paullinias
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Michiels, L., Denis, P., 1926a. Sur la liane Yocco et sur la pre´sencepre´sence de Cafeíne dans les Paullinias. J. Pharm. Belg. 43, 795-797.
Las Plantas y el Hombre
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The Healing Forest Useful plants of the Siona and Secoya Indians of eastern Ecuador
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Isolation of caffeine from Banisteriopsis ineb-rians (Malpighiaceae) Naturwissenschaften 56, 139 Aspectos ethnobota´ de las lianas utilizadas por los indigenas Siona-Secoya de la Amazonıá del Ecuador
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1. Concentration of caffeine and theobromine [% dry wt.] in bark, cortex and wood of a stem section (radius 20 mm) of Paullinia yoco
  • Fig
Fig. 1. Concentration of caffeine and theobromine [% dry wt.] in bark, cortex and wood of a stem section (radius 20 mm) of Paullinia yoco.
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A survey of the useful species of Paullinia L. (Sapindaceae) Advances Econ
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Classification problems of the stimulant “yoco” (Paullinia yoco Schultes & Killip, Sapindaceae): taxonomic and ethnotaxonomic identification in Ecuador, Colombia and Peru
  • Beck
Beck, H.T., 1991. Classification problems of the stimulant ''yoco'' (Paullinia yoco Schultes & Killip, Sapindaceae): taxonomic and ethnotaxonomic identification in Ecuador, Colombia and Peru. In: Rıós, M., Pederson, H.B. (Eds.), Las Plantas y el Hombre. Herbario QCA-P.U.C.E, Quito, Ecuador, pp. 187-197.
A caffeine drink prepared from bark
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Sur la liane Yocco, drogue à caféine du genre Paullinia
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A survey of the useful species of Paullinia L. (Sapindaceae)
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Sur la liane Yocco et sur la présence de Caféine dans les Paullinias
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