RESUMO

The context for this review is the rapid increase in the use of non-nutritive sweeteners (NNSs) instead of sugar in foods and beverages, a situation so prevalent in some countries that consumers are finding it increasingly challenging to access foods without NNSs. The benefits of consuming NNSs on obesity and diabetes are now being questioned, and studies have shown that they may exert physiological activities, sometimes independently of sweet taste receptor stimulation. Few studies, limited mainly to North American and European countries, have described the consumption of NNSs by pregnant or lactating women and infants. Most focus on beverages rather than foods, but all agree that consumption levels have increased dramatically. Although some studies report a negative impact of NNSs on the risk of preterm birth, increased birth weight and decreased gestational age, the level of evidence is low. Several studies have also reported increased weight gain in infancy, associated with maternal NNS intake. Interestingly, several NNSs have been detected in amniotic fluid and breast milk, usually (but not always) at concentrations below their established detection limit in humans. Unfortunately, the impact of chronic exposure of the fetus/infant to low levels of multiple NNSs is unknown. In conclusion, there is a stark contrast between the galloping increase in the consumption of NNSs and the small number of studies evaluating their impact in at-risk groups such as pregnant and lactating women and infants. Clearly, more studies are needed, especially in Latin America and Asia, to fill these gaps and update recommendations.

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Isoflavones (IFs) are biocompounds found in considerable amounts in soybean grains. However, to originate soybean-based materials, the grains must be subjected to numerous thermal and mechanical treatments, which can impair the IFs content. The influence of these treatments was investigated and a protocol for IFs extraction and quantification is proposed. Sequential extractions were performed on industrially pretreated soybean samples (broken, flakes, and collets), on okara submitted to different drying methods (freeze-drying, forced convection, and under vacuum), and on soybean oils extracted with hexane and ethanol. ß-glucosides levels were decreased by the thermal processes of lamination, expansion, and drying, while the aglycone forms were not affected. Lyophilization was identified as the most viable drying method for the quantification of IFs in okara. Soybean oils extracted with ethanol presented significant amounts of aglycone. Furthermore, two stages of extraction were sufficient for the recovery of the IFs from different matrices.

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We report here a series of glucosides which are active as inhibitors of the angiotensin converting enzyme (ACE). They are structurally related to the natural compound eugenol and exhibited significant inhibition values. Their syntheses were expeditious and we could obtain informative docking plots of them complexed to this enzyme. A glucoside derived from eugenol, carrying a carboxylic group in the aglycone, was the most active of them (with an IC50 of 0.4 mM) and showed good binding energies in docking studies with ACE. Moreover, computational prediction of toxicity risks, physicochemical properties and drug score show that the glucoside derivative of eugenol is a suitable compound for optimisation studies aimed at finding new drug candidates.

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Vegetable oil-derived biodiesels have a major quality problem due to the presence of precipitates formed by steryl glucosides, which clog filters and injectors of diesel engines. An efficient, scalable, and cost-effective method to hydrolyze steryl glucosides using thermostable enzymes has been developed. Here, methods to discover, express in recombinant microorganisms and manufacture enzymes with SGase activity, as well as methods to treat biodiesel with such enzymes, and to measure the content of steryl glucosides in biodiesel samples are presented.

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The fruit of Vanilla planifolia is broadly preferred by the agroindustry and gourmet markets due to its refined flavor and aroma. Peruvian Vanilla has been proposed as a possible source for genetic improvement of existing Vanilla cultivars, but, little has been done to facilitate comprehensive studies of these and other Vanilla. Here, a nuclear magnetic resonance (NMR) metabolomic platform was developed to profile for the first time the leaves - organ known to accumulate vanillin putative precursors - of V. planifolia and those of Peruvian V. pompona, V. palmarum, and V. ribeiroi, with the aim to determine metabolic differences among them. Analysis of the NMR spectra allowed the identification of thirty-six metabolites, twenty-five of which were quantified. One-way ANOVA and post-hoc Tukey test revealed that these metabolites changed significantly among species, whilst multivariate-analyses allowed the identification of malic and homocitric acids, together with two vanillin precursors, as relevant metabolic markers for species differentiation.

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Manihot esculenta (cassava) is a root crop originating from South America that is a major staple in the tropics, including in marginal environments. This study focused on South American and African germplasm and investigated the genetic architecture of hydrogen cyanide (HCN), a major component of root quality. HCN, representing total cyanogenic glucosides, is a plant defense component against herbivory but is also toxic for human consumption. We genotyped 3354 landraces and modern breeding lines originating from 26 Brazilian states and 1389 individuals were phenotypically characterized across multi-year trials for HCN. All plant material was subjected to high-density genotyping using genotyping by sequencing. We performed genome-wide association mapping to characterize the genetic architecture and gene mapping of HCN. Field experiments revealed strong broad- and narrow-sense trait heritability (0.82 and 0.41, respectively). Two major loci were identified, encoding for an ATPase and a MATE protein, and contributing up to 7 and 30% of the HCN concentration in roots, respectively. We developed diagnostic markers for breeding applications, validated trait architecture consistency in African germplasm and investigated further evidence for the domestication of sweet and bitter cassava. Fine genomic characterization revealed: (i) the major role played by vacuolar transporters in regulating HCN content; (ii) the co-domestication of sweet and bitter cassava major alleles are dependent upon geographical zone; and (iii) the major loci allele for high HCN in M. esculenta Crantz seems to originate from its ancestor, M. esculenta subsp. flabellifolia. Taken together, these findings expand our insights into cyanogenic glucosides in cassava roots and its glycosylated derivatives in plants.

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The aim of this study was to explore the potential of the agroindustrial waste from two Colombian mango cultivars as sources of bioactive phenolic compounds. Phenolic extracts from mango waste (peels, seed coats, and seed kernels) of 'sugar mango' and 'Tommy Atkins' cultivars were obtained. The bioactive properties of the phenolic extracts were accessed by measuring their free radical scavenging activity and antioxidant effects against lipid oxidation in food products; moreover, their antiproliferative effects against some cell lines of human cancer were explored. It is observed that the agroindustrial waste studied provides promising sources of bioactive phenolics. 'Sugar mango' waste provided extracts with the highest antioxidant effect in food products and antiproliferative activity; these extracts reduced lipid oxidation and cell growth by more than 57% and 75%, respectively. The seed kernel from 'sugar mango' supplied the extract with the best bioactive qualities; in addition, some recognized bioactive phenolics (such as mangiferin and several galloyl glucosides) were observed in this extract and related with its properties. The results obtained suggest that 'sugar mango' waste may be considered a source of bioactive phenolics, with promising uses in food and pharmaceutical products. Thus, a suitable alternative for the use and valorization of agroindustrial waste from Colombian mango cultivars is presented.

RESUMO

The surface group characteristics of mango cultivar peels and seeds were evaluated by infrared spectra, PZC, and functional group composition. The adsorption/reduction of chromium (VI) in aqueous solutions was investigated by varying pH, contact time, initial Cr(VI) concentration, and adsorbent amount. The results show that both peel and seed powders of the mango cultivars showed significant adsorption/reduction capacity for Cr(VI) and that the desorption process obeys pseudo-second-order kinetics. Optimal adsorption occurred at pH 1.0, using a Cr(VI) concentration of 100 mg/L. On average, at pH 1.0, and a concentration of 3 g/L, the maximum adsorption/reduction capacity of Cr(VI) was 83% (peels 76%, seeds 90%). Of the mango powders tested, the most efficient were Tommy seed (100%) and Coite peel (98%) followed by Coite seed (96%) and Tommy peel powders (95%). The adsorption/reduction of Cr(VI) was complete (100%) by the mango seed, in comparison to the peel powders (97%) after 180 min. The data indicates that mango waste products, such as seed and peel powders, are both excellent candidates for the remediation of Cr(VI) from aqueous systems and due to the higher concentration of gallates and galloyl glucosides, the mango seed powders should be the powders of choice for future remediation projects.

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Seventeen new synthetic derivatives of eugenol (6, 8-15 and 8'-15') were planned following literature reports on antifungal activities of nitroeugenol and eugenol glucoside. The anti-Candida activity of these compounds was investigated by in vitro assay, and the cytotoxicity evaluation was performed with the most active compounds. The peracetylated glucosides presented better biological results than their hydroxylated analogues. The glucoside 11, a 4-nitrobenzamide, showed the best potency (MIC50 range 11.0-151.84 µm), the wider spectrum of action, and overall the best selectivity indexes, especially against C. tropicalis (~30) and C. krusei (~15). To investigate its possible mechanism of action, glucoside 11 was subjected to molecular docking studies with Candida sp. enzymes involved in ergosterol biosynthesis. Results have shown that the peracetyl glucosyl moiety and the 4-nitrobenzamide group in 11 are effectively involved in its high affinity with the active site of squalene epoxidase.

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A new series of glucosides modified in their saccharide units were synthesized, evaluated against Candida sp., and compared to prototype 1, an eugenol tetracetyl glucoside previously synthesized and shown to be active against Candida glabrata. Among the new glucosides, benzyl derivative 5 was the most promising, showing fungistatic activity at IC50 18.1 µm against Candida glabrata (threefold higher than fluconazole) and fungicidal activity with a low IC90 value of 36.2 µm. Moreover, the cytotoxic activity of compound 5 (CC50 : 580.9 µm), tested in peripheral blood mononuclear cells, suggests its potential as an agent to treat Candida glabrata infections, with a selectivity index of 32. The new eugenol glucoside 5 may be considered as a novel structural pattern in the development of new anti-Candida drugs.

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A new series of 1,2,3-triazole eugenol glucosides were synthesized. The new compound structures were confirmed by MS, (1)H NMR and (13)C NMR. All of the synthesized compounds were screened for antimicrobial and cytotoxic activity. Five compounds exerted significant activity against the Gram-negative bacteria Salmonella typhimurium with low IC50 values (49.73-68.53 µΜ), and seven compounds were active against the Gram-positive bacteria Micrococcus luteus (42.89-210.94 µM). In vitro cytotoxicity on mouse spleen cells was also evaluated. One compound bearing a phenyl substituent at the triazole ring showed good activity against Salmonella typhimurium (49.73 µM) and low toxicity to normal cells (CC50=157.83 µM). Thus, the compounds herein can be considered for further modification for improving their antibacterial activity or obtaining novel antibacterial drug candidates.

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A new iridoid glucoside has been isolated from the Chilean native Alonsoa meridionalis (L.f.) Kuntze. Its structure has been assigned as 6'-O-ß-d-glucopyranosyl-8-O-acetylharpagide (1) by using spectroscopic methods. Harpagoside (2), laterioside (3) and verbascoside (4) were also identified.

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The polyisoprenylated benzophenones machuone and clusiachromene A have been isolated from the fruits of Clusia columnaris. The hexane extract of the young branches with leaves afforded a new euphane derivative, whose structure was elucidated by spectroscopic methods. On the contrary, the most polar EtOAc and ButOH extracts were constituted of flavonoid C-glucosides (isovitexin, vitexin and vitexin-2"-xyloside) and seven biflavonoids of the so-called Garcinia group.

Dos frutos de Clusia columnaris foram isoladas as benzofenonas poliisopreniladas machuona e clusiacromeno A. Do extrato em hexano obtido de galhos e folhas novas, um novo triterpeno do tipo eufano foi isolado. Sua estrutura foi elucidada através de métodos espectroscópicos. Por outro lado, dos extratos mais polares - em acetato de etila e em butanol, foram isolados os flavonóides C-glicosilados isovitexina, vitexina e vitexina-2"-xilosídeo, além de sete bisflavonóides conhecidos como bisflavonóides do grupo da Garcinia.

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To further evaluate previous indirect evidences of a role for the rubber tree cyanogenic glycosides, of which the main component is linamarin, this study evaluated the translocation incompatibility of the clone IPA 1 (Hevea brasiliensis) with budded crowns of clones of other species. Solutions of KCN were first applied, which caused rapid coagulation of the latex in the laticiphers of IPA 1, at very low concentrations, the same effect being observed in Fx 4098 at higher concentrations. The clone Fx 3864 presented no effect, only a slight reduction of the latex flow at the highest concentration. With linamarin solutions the necrosis, again preceded by latex coagulation, spread longer along the stem, indicating a higher mobility of linamarin than KCN. The clone IPA 1 behaved again sensitive to the lower concentrations of linamarin, with the higher concentrations causing the same effects on Fx 4098 and no effect on Fx 3864. With linamarin a build up of free HCN was detected in the bark of IPA 1. The incompatibility with IPA 1 is caused by the translocation of cianogenic glycosides from the budded crowns to the stem which is deprived of sufficient capacity to remove the HCN liberated by the hydrolisis of cyanogenic glicosides, while the Fx 3864 presented a very efficient detoxifying capacity.

Para caracterizar evidências indiretas do envolvimento dos glicosídeos cianogênicos da seringueira, cujo principal componente é a linamarina, no desenvolvimento dos sintomas de incompatibilidade de enxertia por translocação apresentados pelo clone de painel IPA 1 (Hevea brasiliensis) em enxertos de copa com vários clones de outras espécies de Hevea, tentou-se sua reprodução através da aplicação de soluções com concentrações de cianeto de potássio (KCN) e linamarina no caule do clone IPA 1 e dos clones Fx 4098 e Fx 3864, que não apresentam reação de incompatibilidade com os mesmos clones incompatíveis com o IPA 1. A aplicação de soluções de KCN no caule provocaram rápida coagulação do látex nos laticíferos do IPA 1 com concentrações muito baixas de KCN e mais altas no Fx 4098. No Fx 3864, não houve efeito, exceto leve redução de escoamento com a dose mais alta. Os tratamentos com KCN causaram necrose apenas próximo ao local das aplicações. Com soluções de linamarina, a necrose, também precedida pela coagulação do látex, ocorreu em maior extensão do caule, o que indica maior mobilidade de linamarina, que do KCN. O IPA 1 mostrou-se, novamente, mais sensível às concentrações mais baixas de linamarina, com doses mais altas provocando os mesmos efeitos no Fx 4098 e sem ocorrência de efeitos no Fx 3864. Nos tratamentos com linamarina observou-se o acúmulo de HCN livre na casca do caule do clone IPA 1, responsável pelos sintomas observados. A incompatibilidade com o IPA 1 é provocada pela translocação de glicosídios cianogênicos das copas enxertadas no IPA 1, que não é dotado de suficiente capacidade de remoção do HCN liberado na hidrólise desses glicosídios, tendo o Fx 3864 apresentado desintoxicação mais eficiente.

RESUMO

To further evaluate previous indirect evidences of a role for the rubber tree cyanogenic glycosides, of which the main component is linamarin, this study evaluated the translocation incompatibility of the clone IPA 1 (Hevea brasiliensis) with budded crowns of clones of other species. Solutions of KCN were first applied, which caused rapid coagulation of the latex in the laticiphers of IPA 1, at very low concentrations, the same effect being observed in Fx 4098 at higher concentrations. The clone Fx 3864 presented no effect, only a slight reduction of the latex flow at the highest concentration. With linamarin solutions the necrosis, again preceded by latex coagulation, spread longer along the stem, indicating a higher mobility of linamarin than KCN. The clone IPA 1 behaved again sensitive to the lower concentrations of linamarin, with the higher concentrations causing the same effects on Fx 4098 and no effect on Fx 3864. With linamarin a build up of free HCN was detected in the bark of IPA 1. The incompatibility with IPA 1 is caused by the translocation of cianogenic glycosides from the budded crowns to the stem which is deprived of sufficient capacity to remove the HCN liberated by the hydrolisis of cyanogenic glicosides, while the Fx 3864 presented a very efficient detoxifying capacity.

Para caracterizar evidências indiretas do envolvimento dos glicosídeos cianogênicos da seringueira, cujo principal componente é a linamarina, no desenvolvimento dos sintomas de incompatibilidade de enxertia por translocação apresentados pelo clone de painel IPA 1 (Hevea brasiliensis) em enxertos de copa com vários clones de outras espécies de Hevea, tentou-se sua reprodução através da aplicação de soluções com concentrações de cianeto de potássio (KCN) e linamarina no caule do clone IPA 1 e dos clones Fx 4098 e Fx 3864, que não apresentam reação de incompatibilidade com os mesmos clones incompatíveis com o IPA 1. A aplicação de soluções de KCN no caule provocaram rápida coagulação do látex nos laticíferos do IPA 1 com concentrações muito baixas de KCN e mais altas no Fx 4098. No Fx 3864, não houve efeito, exceto leve redução de escoamento com a dose mais alta. Os tratamentos com KCN causaram necrose apenas próximo ao local das aplicações. Com soluções de linamarina, a necrose, também precedida pela coagulação do látex, ocorreu em maior extensão do caule, o que indica maior mobilidade de linamarina, que do KCN. O IPA 1 mostrou-se, novamente, mais sensível às concentrações mais baixas de linamarina, com doses mais altas provocando os mesmos efeitos no Fx 4098 e sem ocorrência de efeitos no Fx 3864. Nos tratamentos com linamarina observou-se o acúmulo de HCN livre na casca do caule do clone IPA 1, responsável pelos sintomas observados. A incompatibilidade com o IPA 1 é provocada pela translocação de glicosídios cianogênicos das copas enxertadas no IPA 1, que não é dotado de suficiente capacidade de remoção do HCN liberado na hidrólise desses glicosídios, tendo o Fx 3864 apresentado desintoxicação mais eficiente.