Anthraquinone as emerging contaminant: technological, toxicological, regulatory and analytical aspects.

Anthraquinone (anthracene-9,10-dione) is a multifaceted chemical used in the paper industry, in the production of synthetic dyes, in crop protection against birds and is released from fossil fuels. Additionally, the anthraquinone scaffold, when substituted with sugars and hydroxyl groups is found in plants as metabolites. Because of these multiple applications, it is produced on a large scale worldwide. However, its toxicological aspects have gained interest, due to the low limits in the foods defined by legislation. Worrying levels of anthracene-9,10-dione have been detected in wastewater, atmospheric air, soil, food packaging and more recently, in actual foodstuffs. Recent investigations aiming to identify the anthracene-9,10-dione contamination sources in teas highlighted the packaging, leaves processing, anthracene metabolism, reactions between tea constituents and deposition from the environment. In this context, this review seeks to highlight the uses, sources, biological effects, analytical and regulatory aspects of anthracene-9,10-dione.

Chemical Constituents and Biological Activities of Croton heliotropiifolius Kunth.

Croton heliotropiifolius Kunth (Euphorbiaceae), whose occurrence has already been registered in the most varied Brazilian biomes, is commonly found in the Chapada do Araripe, Ceará. The species is traditionally used to treat fungal, parasitic, and degenerative diseases. This study investigated the chemical composition and pharmacological potential (antioxidant, antifungal, antiparasitic, and cytotoxic) of an aqueous extract obtained from the roots of C. heliotropiifolius. Following a qualitative phytochemical screening, the chemical constituents were identified by ultra-efficiency liquid chromatography coupled witha quadrupole/time-of-flight system (UPLC-QTOF). The antioxidant potential was verified by thin-layer chromatography (TLC). The direct and combined antifungal activity of the extract against opportunistic Candida strains was investigated using the microdilution method. The minimal fungicidal concentration (MFC) was determined by subculture, while the modulation of the morphological transition (fungal virulence) was evaluated by light microscopy. The in vitro antiparasitic activity was analyzed using epimastigotes of Trypanosoma cruzi and promastigotes of Leishmania braziliensis and Leishmania infantum, while cytotoxicity was determined in cultures of mouse fibroblasts. The phytochemical analysis identified the presence of acids, terpenes, flavonoids, lignans, and alkaloids. Among these constituents, the presence of polar and non-polar phenolic compounds with known antioxidant action was highlighted. While the extract showed clinically ineffective antifungal effects, it could enhance the effectiveness of fluconazole, in addition to inhibiting the morphological transition associated with increased virulence in Candida strains. Although the extract showed low cytotoxicity against fibroblasts, it also had weak antiparasitic effects. In conclusion, Croton heliotropiifolius is a source of natural products with antifungal and antioxidant potential.

Atmospheric cold plasma frequency imparts changes on cashew apple juice composition and improves vitamin C bioaccessibility.

This study evaluated the atmospheric cold plasma (ACP) effect on cashew apple juice composition at different frequencies (200 and 700 Hz). The impact of this non-thermal technology on the organic juice compounds after the processing and along with the in vitro digestion carried out in a simulated digestion system at 37 °C/6 h was evaluated. The changes in the juice composition were determined by NMR spectroscopy and chemometric analyses. Vitamin C and total phenolic compounds were also quantified in processed and non-processed (control) juices and after each digestion phase. The results showed decreased glucose and fructose in samples treated by ACP and an increment in malic acid concentration for ACP700. ACP increased the amount of vitamin C in the juices and did not affect the total phenolic content. The gastric digestion highlighted the pronounced effect of plasma on the juice composition, increasing all of the components detected by NMR. Cashew apple juice processed by ACP700 presented a higher concentration of malic acid and phenylalanine. An increased bioaccessibility of vitamin C was also found for ACP700. Although ACP processing has decreased some compounds' concentration, this technology improved the bioaccessibility of vitamin C - the main bioactive compound of cashew apple juice.

UPLC-MS-ESI-QTOF Analysis and Antifungal Activity of the Spondias tuberosa Arruda Leaf and Root Hydroalcoholic Extracts.

The aim of this study was to identify and evaluate the chemical compositions and effects of the S. tuberosa leaf and root hydroalcoholic extracts (HELST and HERST) against different strains of Candida. Chemical analysis was performed by Ultra-Performance Liquid Chromatography Coupled to Quadrupole/Time of Flight System (UPLC-MS-ESI-QTOF). The Inhibitory Concentration of 50% of the growth (IC50) as well as the intrinsic and combined action of the extracts with the antifungal fluconazole (FCZ) were determined by the microdilution method while the minimum fungicidal concentrations (MFCs) and the effect on fungal morphological transitions were analyzed by subculture and in humid chambers, respectively. From the preliminary phytochemical analysis, the phenols and flavonoids were the most abundant. The intrinsic IC50 values for HELST ranged from 5716.3 to 7805.8 µg/mL and from 6175.4 to 51070.9 µg/mL for the HERST, whereas the combination of the extracts with fluconazole presented IC50 values from 2.65 to 278.41 µg/mL. The MFC of the extracts, individually, for all the tested strains was ≥16384 µg/mL. When fluconazole was combined with each extract, the MFC against CA URM 5974 was reduced (HELST: 2048 and HERST: 4096 µg/mL). Synergism was observed against standard C. albicans (CA) and C. tropicalis (CT) strains and with the root extract against the CT isolate. The leaf extract inhibited the morphological transition of all strains while the root extract inhibited only CT strains.

Development of a UPLC-ESI-MS method for simultaneous determination of flavonoids and diterpenes in Egletes viscosa (L.) Less herbal products.

Egletes viscosa (L.) Less (Asteraceae) is a tropical aromatic herb whose flower buds are used for gastrointestinal disorders. Its gastroprotective properties have been attributed to the flavonoid ternatin and the furan diterpenes tanabalin and centipedic acid. The aim of this study was to develop a method of ultra-performance liquid chromatography coupled to electrospray ionization and mass spectrometry (UPLC-ESI-MS) for identifying the constituents from E. viscosa flower buds as well as quantifying its bioactive compounds in herbal products. Infusions and tincture from wild and commercial E. viscosa materials were directly injected on a UPLC-quadrupole-time-of-flight system (UPLC-q-TOF). Afterwards, reference standards were used to quantify ternatin, tanabalin and centipedic acid in these samples, employing a UPLC-single quadrupole system set up for positive mode and Selected Ion Monitoring (SIM). Seventeen compounds were identified, including caffeic acid derivatives, flavonoids and diterpenes, from which seven have been reported for the first time in this specie. The quantification method showed good linearity (R > 0.99), accuracy, precision and sensitivity. The intra-day and inter-day precisions presented relative standard deviations inferior to 6.04 and 8.78%, respectively. The recoveries of all the analytes varied 82.25-117.87%. The limits of detection and quantification ranged between 10-25 µg/L and 25-75 µg/L, respectively. For the samples, the contents of ternatin, tanabalin and centipedic acid ranged from 0.89 to 8.03 mg/L, 0.84-16.8 mg/L and 3.21-16.8 mg/L, respectively. The method demonstrated to be rapid, sensitive and reliable for the quality control of E. viscosa-based products, besides being applicable to other plant extracts containing flavonoids and diterpenes.

Effects of industrial cashew nut processing on anacardic acid content and allergen recognition by IgE.

Cashew nuts are important both nutritionally and industrially, but can also cause food allergies in some individuals. The present study aimed to assess the effect(s) of industrial processing on anacardic acids and allergens present in cashew nuts. Sample analyses were performed using liquid chromatography coupled with mass spectrometry, SDS-PAGE and immunoassay. The anacardic acid concentration ranged from 6.2 to 82.6mg/g during processing, and this variation was attributed to cashew nut shell liquid incorporation during storage and humidification. Dehydrated and selected samples did not significantly differ in anacardic acid content, having values similar to the raw sample. SDS-PAGE and immunoassay analysis with rabbit polyclonal sera and human IgE indicated only minor differences in protein solubility and antibody binding following processing steps. The findings indicate that appreciable amounts of anacardic acid remain in processed nuts, and that changes to cashew allergens during industrial processing may only mildly affect antibody recognition.