1H NMR-based metabolic profile and chemometric analysis for the discrimination of Passiflora species genotypic variations.

The species of the genus Passiflora (Passifloraceae family) have been used as food, cosmetic and traditional herbal. As a result, the Passiflora species are widely cultivated and has an economic, medicinal and ornamental importance. The popular designation as "passion fruit" and chemical profile of several Passiflora species remains unknown. The lack of chemical information contributes to the erroneous classification and adulteration. In recent years, special attention has been paid to the bioactivity and phytochemical profiles of several Passiflora species extracts. In this research, 1H NMR-based metabolic profiling coupled with chemometric tools was used to characterize and distinguish extracts obtained from different wild Passiflora species (P. alata, P. cincinnata, and P. setacea) and genetic varieties (P. alata var. BRS Pérola do Cerrado, P. cincinnata var. BRS Sertão Forte, and P. setacea var. BRS Pérola do Cerrado). Fourteen metabolites were identified by 1D and 2D NMR experiments, highlighting the presence of fatty acids, carbohydrates, saponins, alkaloids, and mainly C-glycosidic flavones. Principal components analysis (PCA) allowed discrimination of Passiflora extracts, which the quadranguloside, oleanolic acid-3-sophoroside, α-glucose, ß-glucose, and vitexin-2-O"-rhamnoside were relevant in the differentiation of P. alata and P. alata var. BRS Pérola do Cerrado, while the flavones isovitexin and isovitexin-2-O"-xyloside were dominant in the grouping of P. setacea and P. setacea var. BRS Pérola do Cerrado, and finally P. cincinnata and P. cincinnata var. BRS Sertão Forte grouped by the influence of the fatty acids, sucrose, flavones (isoorientin and vitexin-2-O"-xyloside), and trigonelline. The varieties of P. setacea, and P. cincinnata are chemically equivalent to the original Passiflora species. However, the PCA analysis showed that the genetic variety of P. alata occupied a different position in the scores plot provoked mainly by the presence of oleanolic acid-3-sophoroside. The 1H NMR metabolic profile can be efficient for quality control evaluation, and can contribute to the investigation of new alternatives for official Passiflora herbal medicines.

New ent-kaurene-type nor-diterpene and other compounds isolated from Annona vepretorum Mart. (Annonaceae).

A new nor-ent-kaurene diterpene and ten other compounds were isolated from Annona vepretorum stems, including four kaurene diterpenes, three alkamides, one sesquiterpene and two steroids. Their chemical structures were elucidated using spectroscopic methods, including 1D-, 2D-NMR, and HRESIMS. The absolute configuration of compounds 1, 5, 8, 9 and 10 was confirmed by CD experiments. Compounds 1-5 and 8-10 were evaluated for cytotoxic activity using (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) MTT method, against three human carcinoma cell lines: human colon (HCT-116), glioblastoma (SF295) and prostate (PC3). However, all isolated compounds exhibited low cytotoxic activity.

Hypolipidemic potential and safety profile of the ethanolic extract and flour of the peel of Passiflora Cincinnata Mast. (Passifloraceae) in mice.

Passiflora cincinnata Mast. is described as a native Caatinga species, used by nutritional and medicinal purposes, although there are still few studies and pharmacological data related to this species. This paper aims to evaluate the safety profile and hypolipidemic potential of the fruit peel of this species in mice. It was analyzed the chemical composition of ethanolic extract (EtOH-Pc) by HPLC-DAD-MS/MS, and the organic and inorganic composition of flour (MF-Pc). Also were evaluated the acute toxicity, the lipid-lowering potential of these samples, through of a pretreatment (oral: 100 and 200 mg/kg), and a single treatment with the same doses, after hyperlipidemic induction with triton WR-1339, using as animal model Swiss Mus musculus mice, besides histopathological analysis. The presence of flavonoids in the extract was confirmed, mainly C-glycosides, and antioxidant minerals and pectin, in flour. No clinical signs of toxicity or death were reported in the study. In the hyperlipidemia study model used, the analyzed substances, at all doses, notably decreased the lipid levels of TC, TG, LDL-c and VLDL-c and increase the HDL-c levels in the induced hyperlipidemic mice (p < 0.05). The results of the histopathological analysis showed that in the group only induced was identified the discrete presence of hepatic steatosis, in 2 animals at the analysis of 24 h, not being visualized in the groups treated with the substances evaluated. The results obtained in the present study suggest a hypolipidemic potential of the extract and flour, obtained from the fruit peel of Passiflora cincinnata Mast.

Hydroalcoholic Extract of Encholirium spectabile Mart. (Bromeliaceae) in O/W Emulsions as an Additive against the UVB Radiation.

The use of sunscreen is one of the photoprotection measures most used by the population, so these products must offer broad-spectrum protection against UVA and UVB radiation. Encholirium spectabile, popularly known as "macambira-de-flecha," is a species characterized by its rocky outcrops and found in the Caatinga. This biome is known for extreme droughts and dry periods, and for this reason, its vegetation needed to develop resistance mechanisms. The aim of this work was to evaluate the use of E. spectabile incorporated in O/W emulsion as a potential photoprotective agent and their antioxidant activity. Four chemical constituents (ferulic acid, caffeic acid, p-coumaric acid and apigenin) were identified by HPLC-DAD analysis, and emulsions containing different concentrations (1%, 2.5% and 5%) of the extract without and with the addition of chemical filters (octyl methoxycinnamate and benzophenone-3) were prepared and submitted to the test of preliminary stability. The Q formulation demonstrated little variation in the preliminary stability test and was selected for estimated your protection against UVB and determination of in vitro protection factor UVA. The formulations remained stable during the freeze-thaw cycle; the extract despite maintaining the UVA-PF and decreasing the wavelength showed an increase in FPS from 14.4 (control) to 18.8 (control+ Es-HA80).

Phytochemicals and biological properties of Annona coriacea Mart. (Annonaceae): A systematic review from 1971 to 2020.

Annona coriacea Mart., popularly known as "marolo", "araticum" and "araticum-liso" is a species distributed in Paraguay and Brazil, and easily found in Caatinga, Cerrado, and Pantanal biomes. The araticum has been used in folk medicine to treat stomatitis, neuralgia, rheumatism, headaches, furuncle, ulcers, and dermatitis. This systematic review aimed to provide a comprehensive overview of the ethnomedicinal use, phytochemistry, and pharmacological activity of A. coriacea. A search for scientific articles of electronic databases (Science Direct, PubMed, Lilacs, Scopus, Google Scholar, Scielo, and Web of Science) was performed identifying studies published until November 2020. All papers considering traditional medicinal uses, phytochemistry, and pharmacological properties were included. Forty-six articles (n = 212 subjects) met the inclusion criteria set for this review. Of the 46 articles reviewed, 34 were focused on biological activity investigations, while 12 were limited to phytochemical studies. These studies showed the presence of a diversity of secondary metabolites such as acetogenins, sesquiterpenes, alkaloids, flavonoids, and diterpenes. To date, pharmacological tests have demonstrated significant biological activities of this plant, being the most promising anticancer, anti-inflammatory, antiulcer, and insecticide activities. Additionally, the medicinal utilization of A. coriacea appears to be promising, supporting its possible uses for human health with antioxidant, anxiolytic, antiulcer, insecticide, and antiparasitic activities. Ultimately, comprehensive studies involving clinical trials are required to validate the existing traditional practices and their related health benefits scientifically.

Identification of flavonoids in Hymenaea martiana Hayne (Fabaceae) by HPLC-DAD-MSn analysis.

Hymenaea martiana is a native tree known in Brazil as 'jatobá' and used in folk medicine to treat pain and inflammation. The aim of this work was to identify the flavonoids present in the crude ethanolic extract and ethyl acetate fraction using HPLC-DAD and LC-MSn analysis. The ethanolic extract was partitioned to obtain the ethyl acetate fraction. The analysis of astilbin content also was carried out by HPLC analysis. HPLC-DAD-ESI/MSn analysis of the ethanolic extract and ethyl acetate fraction revealed the presence of eleven peaks in the chromatograms, and all these peaks were identified: taxifolin, eucryphin, astilbin and 3 diastereoisomers, engeletin and 2 diastereoisomers, quercitrin and 2,6,3',4'-tetrahydroxy-2-benzylcoumaran-3-one. The ethyl acetate fraction had a higher astilbin concentration (151.87 µg/mL) than the ethanolic extract (40.13 µg/mL). In conclusion, the species could be considered a good source of flavonoids, which can be related to the main chemotaxonomic markers for the genus Hymenaea.

1H HR-MAS NMR and chemometric methods for discrimination and classification of Baccharis (Asteraceae): A proposal for quality control of Baccharis trimera.

Baccharis trimera is a species recognized by health agencies and recommended by the Brazilian Pharmacopoeia by having medicinal properties. In this work, HR-MAS NMR spectroscopy combined with chemometric tools, such as Principal Components Analysis (PCA), Partial Least Squares Discriminant Analysis (PLS-DA) and Soft Independent Modeling by Class Analogy (SIMCA), were used to evaluate the quality control and authenticity of commercial samples of Baccharis, as well as to discriminate B. trimera samples from other species of the Caulopterae section (B. articulata, B. trimera, B. junciformis, B. milleflora, and B. myriocephala). The high morphological similarity of these species makes it difficult for their identifications and discriminations, even by taxonomists. Different PCA pre-processing (autoscaling, Pareto scaling, and mean centering) allowed to discriminate B. trimera and B. myriocephala from the other species, mainly due to the presence of carquejyl acetate, indicated their chemical similarity. The 1H HR-MAS NMR spectral profile offers the possibility of tracking not only the chemical markers, such as the presence of carquejyl acetate, which can also be helpful in the B. trimera authentication/identification. The application of classification methods in standard samples revealed that PLS-DA models showed better performance on the calibration and validation sets than SIMCA model. However, PLS-DA and SIMCA applied to commercial samples showed that none of the commercial samples were classified as B. trimera, which suggested the lack of strict quality control regarding these products. The methodology developed in the present work might contribute to chemotaxonomy of the genus Baccharis.

Products Derived from Buchenavia tetraphylla Leaves Have In Vitro Antioxidant Activity and Protect Tenebrio molitor Larvae against Escherichia coli-Induced Injury.

The relevance of oxidative stress in the pathogenesis of several diseases (including inflammatory disorders) has traditionally led to the search for new sources of antioxidant compounds. In this work, we report the selection of fractions with high antioxidant action from B. tetraphylla (BT) leaf extracts. In vitro methods (DPPH and ABTS assays; determination of phenolic and flavonoid contents) were used to select products derived from B. tetraphylla with high antioxidant action. Then, the samples with the highest potentials were evaluated in a model of injury based on the inoculation of a lethal dose of heat-inactivated Escherichia coli in Tenebrio molitor larvae. Due to its higher antioxidant properties, the methanolic extract (BTME) was chosen to be fractionated using Sephadex LH-20 column-based chromatography. Two fractions from BTME (BTFC and BTFD) were the most active fractions. Pre-treatment with these fractions protected larvae of T. molitor from the stress induced by inoculation of heat-inactivated E. coli. Similarly, BTFC and BTFD increased the lifespan of larvae infected with a lethal dose of enteroaggregative E. coli 042. NMR data indicated the presence of aliphatic compounds (terpenes, fatty acids, carbohydrates) and aromatic compounds (phenolic compounds). These findings suggested that products derived from B. tetraphylla leaves are promising candidates for the development of antioxidant and anti-infective agents able to treat oxidative-related dysfunctions.

1H HR-MAS NMR-based metabolomics study of different persimmon cultivars (Diospyros kaki) during fruit development.

1H HR-MAS NMR spectroscopy was used to track the metabolic changes throughout the whole development of astringent ('Giombo') and non-astringent ('Fuyu') cultivars of persimmon (Diospyros kaki). The NMR data revealed the low concentration of amino acids (threonine, alanine, citrulline and GABA) and organic acids (malic acid). In addition, the signals of carbohydrates (sucrose, glucose and fructose) seemed to play the most important role in the fruit development. In both cultivars, the growth was characterized by fluctuating sucrose concentration along with a constant increase in both glucose and fructose. In the initial growth stage, the polyphenol composition was quite different between the cultivars. Gallic acid was detected throughout the growth of 'Giombo', while for 'Fuyu', signals of polyphenols disappeared over time. Additional multivariate analysis suggested that these cultivars share many metabolic similarities during development. These findings might help the comprehension of fruit development, which in turn, impacts the quality of the fruits.

Chemical composition of the essential oils of Annona pickelii and Annona salzmannii (Annonaceae), and their antitumour and trypanocidal activities.

The essential oils from the leaves of Annona pickelii and Annona salzmannii (Annonaceae) were obtained by hydrodistillation using a Clevenger apparatus, and analysed by GC-MS and GC-FID. A total of 21 compounds were identified in the essential oil of A. pickelii and 23 in that of A. salzmannii; sesquiterpenes predominated in both essential oils. Bicyclogermacrene (38.0%), (E)-caryophyllene (27.8%), α-copaene (6.9%) and α-humulene (4.0%) were the main components of A. pickelii, while δ-cadinene (22.6%), (E)-caryophyllene (21.4%), α-copaene (13.3%), bicyclogermacrene (11.3%) and germacrene D (6.9%) were the main components of A. salzmannii. The biological activities of the essential oils against Trypanosoma cruzi epimastigote forms and cytotoxicity against tumour cell lines (antitumour) were investigated. The essential oils showed potent trypanocidal and antitumour activities with values of IC50 lower than 100 µg mL(-1).

Essential oil from the leaves of Annona vepretorum: chemical composition and bioactivity.

The essential oil from the leaves of Annona vepretorun was obtained by hydrodistillation using a Clevenger-type apparatus and analyzed by GC-MS and GC-FID. Eighteen compounds representing 98.1% of the crude essential oil were identified. The major compounds identified were bicyclogermacrene (43.7%), spathulenol (11.4%), alpha-felandrene (10.0%), alpha-pinene (7.1%), (E)-beta-ocimene (6.8%), germacrene D (5.8%), and p-cymene (4.2%). The trypanocidal activity against Trypanosoma cruzi epimastigote forms, as well as, the antimicrobial and antioxidant proprieties was investigated. The essential oil showed a potent trypanocidal activity with IC50 value of 31.9 +/-1.3 microg x mL(-1). For antimicrobial activity, the best result was observed against Candida tropicalis with a MIC value of 100 microg x mL(-1). For antioxidant capacity the essential oil showed weak activity.

Chemical composition and antioxidant, antimicrobial, and larvicidal activities of the essential oils of Annona salzmannii and A. pickelii (Annonaceae).

The essential oils from the leaves of Annona salzmannii and A. pickelii (Annonaceae) growing in Sergipe, northeastern region of Brazil, were obtained by hydrodistillation using a Clevenger-type apparatus, and analyzed by GC/MS and GC/FID. Thirty-four compounds were identified in the essential oil of A. salzmannii and twenty-seven in that of A. pickelii; sesquiterpenes predominated in both essential oils. Bicyclogermacrene (20.3%), (E)-caryophyllene (19.9%), delta-cadinene (15.3%), alpha-copaene (10.0%), and allo-aromadendrene (5.7%) were the main components of A. salzmannii, and bicyclogermacrene (45.4%), (E)-caryophyllene (14.6%), and alpha-copaene (10.6%) of A. pickelii. The essential oils showed significant antioxidant capacity in the ORAC(FL) and DPPH assays. The antimicrobial activity of these essential oils was also evaluated against bacteria and fungi, as well as the larvicidal activity against Aedes aegypti larvae.