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Eugenia lisboae M.A.D. Souza (Myrtaceae) is a species found in the Amazon biome, recently described and has not yet been studied regarding its chemical properties. This study aims to identify the main chemical constituents of crude ethyl acetate and ethanolic extracts from E. lisboae leaves. These crude extracts were fractionated using chromatographic methods (LC and HPLC). The identified compounds are a triterpene (1), three organic acids (2 - 4), and two flavonoids (5 and 6). These structures were determined by analyzing the spectroscopic (NMR and MS) data. Compound 6 was named lisboaeflavanonol A {(−)-2R,3R-dihydrokampferol 3-O-β- d -xylopyranosyl-(1”'→2”)-α- l -rhamnopyranoside}, undescribed in the literature. These were the first compounds described in this matrix, and the chemical composition is in line with chemistry of the Eugenia genus. In addition, preliminary molecular docking analysis indicated lisboaeflavanonol A as a potential inhibitor of 3-chymotrypsin-like cysteine protease (3CLpro) and RNA-dependent RNA polymerase (RdRp), which are important SARS-CoV-2 non-structural proteins (NSPs).

The effects of different drying methods (freeze- and spray-drying) and carriers (gum Arabic and inulin) on the powder characterization and stability of the bioactive compounds of Hibiscus acetosella extract (HAE) during storage were evaluated. The 1H NMR spectrum of the HAE revealed characteristic signals of the caffeoyl hydroxycitric acid. The encapsulated extract powder presented different morphology according to the drying processes. The powders produced by the freeze-drying process presented higher retention of bioactive compounds due to the low temperature process. The mixture of gum Arabic and inulin as carrier resulted in the absorption of larger amount of water. The half-life time of the encapsulated extract powders ranged from 31 to 36 h (DPPH) and from 34 to 71 h (phenolic compounds). In general, the powders constituted of gum Arabic and recovered by the freeze-drying process presented better protection and retention of the bioactive compounds from the HAE.

The goal of this paper was to develop a biodegradable system containing the essential oil from Allium sativum bulbs encapsulated in PCL/gelatin-based nanoparticles, as well as evaluate its efficiency to control Aedes aegypti Linn. larvae and Cerataphis lataniae Bois. aphids. The essential oil was analyzed by GC-FID and GC-MS, and six compounds were identified, representing 93.1% of the total oil. The major compounds were diallyl trisulfide (51.8%), diallyl disulfide (23.2%) and allyl methyl trisulfide (13.6%). The PCL/gelatin-based nanoparticles containing this essential oil exhibited encapsulation efficiency higher than 94%, average particle diameter around 200 nm and zeta potential values about −36 mV. The essential oil presented no antioxidant nor enzymatic activities, so its effectiveness might be explained by the presence of sulfur compounds. The release kinetics of the encapsulated essential oil confirmed the release mechanism by the Fick's Law. About 50% of the encapsulated essential oil was released after 1 h, and about 90% was released after 50 h. This behavior is interesting from the technological point of view since the nanoparticles released as much oil as possible in a short period of time and then the lethal dosages were maintained along the time. Nanoparticles containing the encapsulated essential oil was submitted to in vitro bioassays against A. aegypti and C. lataniae and showed 100% of mortality against larvae and aphids up to 24 h. In conclusion, the essential oil from A. sativum presented effectiveness to be applied in sustainable management of pests in greenhouses, as well as for larvicidal control.

The leaves of Eugenia biflora (Myrtaceae) are traditionally used by Amazonian populations for the control of diabetes. However, their chemical composition has not yet been described and pharmacological evidence has not been reported.This study aimed to identify the chemical constituents and evaluate the hypoglycemic and toxic effect of the dry extract of the E. biflora leaves (DEEB).DEEB, obtained by infusion, was analyzed using LC-HRMS and NMR, whose the catechin flavonoid was quantified using NMR. The antidiabetic effect of DEEB was evaluated according to its inhibition of the enzymes α-amylase and α-glucosidase, as well as the content of total phenols, free radical scavengingand antiglycation activities, and its in vitro cell viability. Oral maltose tolerance and chronic multiple dose tests (28 days) in streptozotocin-induced diabetic mice (STZ) were performed. The hypoglycemic effect and toxicity of this extract were evaluated in the multiple dose assay. Biochemical parameters, hemolysis, and levels of the thiobarbituric acid reactive species in the liver were investigated and histopathological analyses of the kidneys and liver were performed.Eight phenolic compounds were identified, with catechin (15.5 ± 1.7 mg g-1) being the majority compound and a possible chemical marker of DEEB. The extract showed inhibition activity of the enzyme α-glucosidase. Chronic administration of DEEB (50 mg/kg of body weight) reduced glucose levels in diabetic animals, similar to acarbose; however, DEEB (100 and 200 mg/kg bw) caused premature death of mice by D22 of the treatment. Our data indicate that one of the mechanisms of toxicity in DEEB may be related to the aggravation of oxidative stress in the liver. This histopathological study indicated that DEEB failed to minimize the progression of the toxicity of diabetes caused by STZ.This study demonstrated the hypoglycemic potential of E. biflora leaves. However, the prolonged use of this tea can be harmful to its users due to its considerable toxicity, which needs to be better investigated.

Myrcia multiflora (Lam.) DC. is often used in Brazilian folk medicine to control diabetes. Analysis using HPLC-HRMS and NMR of the dry extract from the infusion of leaves of this species revealed twelve phenolic compounds. Among these compounds, chlorogenic acid (1), 4-O-caffeoylquinic acid (2), corilagin (3), chebulagic acid (4), pedunculagin (5), quercetin-3-O-β-2″-galloylglucoside (7), and kaempferol-3-O-rhamnoside (12) are described for the first time in this matrix. Furthermore, six compounds were quantified using qNMR. The compounds in the dry extracts are 3, 6 (myricetin-3-O-d-glucoside), 8 (myricitrin), 9 (hyperoside), 10 (guaijaverin) and 11 (quercitrin). These compounds may be considered chemical markers in this matrix. In addition, this extract presents activities of α-glucosidase inhibition (IC50 = 79.9 μg mL-1) and glycation in vitro (IC50 = 10.2 μg mL-1), in addition to antioxidant activity against DPPH and ABTS radicals (1,856.7 and 1,032.0 μmol TEq, respectively). This extract did not show significant cytotoxicity in human fibroblasts. Therefore, the enzymatic inhibition, anti-AGE (advanced glycation end-products) and antioxidant activities of Myrcia multiflora leaves corroborated its antidiabetic therapeutic potential and instigates future preclinical studies aimed at the treatment of diabetes mellitus and its complications.

Growth in the international popularity of Brazil nuts oil (Bertholletia excelsa, Bonpl.) has demanded a closer look at quality aspects of the nuts. In this context, time-domain 1H nuclear magnetic resonance spectroscopy (TD-NMR) can be a useful tool for assessing the lipid portion of such matrices. In this work, a TD-NMR method was developed and validated to assess the oil content directly from Brazil nuts following the ISO 10565:1998 and DOQ-CGCRE-008. Full validation was addressed covering the working range from 0.67 to 25.00 g (coefficient of determination, R2 = 0.9993). Limits of detection (LOD) and quantification (LOQ) were 0.20 and 0.67 g, respectively. The repeatability and intermediate precision assays met the guide requirements. Oil contents obtained in two laboratories (different equipment) were statistically similar (66.93 ± 4.69 and 70.13 ± 4.15%), highlighting the method’s robustness. The developed approach has the potential to be adopted as an industrial reference method for in situ monitoring of Brazil nuts oil contents.

Fermentation is a preservation process responsible for increasing food product shelf life. In this context, alcoholic fermentation can add value to unconventional Amazon fruits, e.g., araçá-boi (Eugenia stipitata). This fruit has various antioxidant phenolic compounds with well-known nutraceutical properties. However, araçá-boi is still underexplored by food industry. This rationale led to investigate the influence of five commercial yeasts (Saccharomyces cerevisiae) and filtration process on chemical composition and antioxidant capacity of araçá-boi beverages. DPPH and Folin Ciocalteu assays were used to determine antioxidant capacity and total phenolic content. Organic compounds’ contents were assessed by NMR-ERETIC2. In all beverages, ten compounds [tyrosol, sucrose, fructose, (α/β)-glucose, ethanol, malic, citric, gallic, and succinic acids] were identified and quantified. The highest phenolic concentrations [gallic acid (390.0 µM) and tyrosol (380.0 µM)] were found in Biolievito Bayanus (BBA) beverage. The new BBA beverage was used for investigating filtration process influence on chemical composition and antioxidant responses. Alcoholic content (unfiltered: 13.9°GL and filtered: 12.7°GL), antioxidant responses, and total phenolic contents were influenced by filtration process. The yeast type and unfiltered process were determinant for chemical content and antioxidant capacity of beverages. These results might be useful to private sector and future production and commercialization of araçá-boi beverages. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s13197-020-04721-x) contains supplementary material, which is available to authorized users.

The present study was carried out to evaluate an alternative controlling agent for greenhouse pests and the yellow fever mosquito larvae. The potential bioactivity of Licaria puchury-major (Mart.) Kosterm. (“puxuri”) was evaluated here against three most common pests in tropical and subtropical countries: Aedes aegypti Linn. Larvae, Tetranychus urticae Koch. mites and Cerataphis lataniae Boisd. aphids. The essential oil from seeds was analyzed by GC-FID and GC-MS. The major compounds were safrole (38.8%) and eucalyptol (21.7%). Phenylpropanes (51.7%) was the main group of compounds and oxygenated monoterpenes represented 28.8% of the total oil. The essential oil has shown no inhibition of acetylcholinesterase (AChE) in the tested concentrations. However, potential antioxidant activities were evaluated by different methods [DPPH: LD50 = (27.8 ± 1.0) µg/.mL; ABTS: (977.3 ± 25.2) µM TEs/g (Trolox Equivalents); FRAP: (548.2 ± 29.0) µM Fe(II)/g]. A significant larvicidal potential for 24 h of exposure was observed with LD50 = 98.9 µg/mL, being an indicative that the larval mortality may occur by ingestion or contact due to the no inhibition against AChE. Volatile phase effects were evaluated against T. urticae Koch. and C. lataniae Boisd. and LD50 were found about 30.8 and 13.5 µg/mL, respectively. These results are consistent with an octopaminergic effect, since some phenylpropanoids (such as Safrole, identified as the major compound in this work) can block octopamine, a multi-functional, naturally occurring biogenic amine. Then, this study clearly illustrated the efficacy of the investigated seeds, which encourages the development of a new potential natural controlling agent against these common pests due to the abundance of these seeds in the Amazon region and to the high essential oil yield. © 2018 ACG Publications. All rights reserved.

The main objective of the present study is to find an alternative controlling agent for some devastating greenhouse pests, and the yellow fever mosquito larvae. More specifically, the potential bioactivity of Lippia origanoides Kunth. (“erva-de-Marajo”) has been evaluated here against three most common pests found in tropical and subtropical countries: Tetranychus urticae Koch. mites, Cerataphis lataniae Boisd. aphids and Aedes aegypti Linn. larvae. The essential oil extracted from leaves of Lippia origanoides Kunth. has been analyzed by GC-FID and GC–MS and 32 compounds have been identified, representing 97.63% of the raw essential oil. The major compounds are carvacrol (48.31%), p-cymene (9.11%) and thymol (8.78%). The essential oil has been tested for AChE inhibition, obtaining IC50 = 16.93 μg/mL, as well as for its potential antioxidant activities by different methods [DPPH: IC50 = 8.4 ± 0.1 μg/mL, ABTS: 691.8 ± 44.3 μM TEs/g (Trolox Equivalents) and FRAP: 933.1 ± 8.1 μM Eq Fe(II)/g]. Our results have shown acaricidal and insecticidal activities of this oil against T. urticae Koch. and C. lataniae Boisd. Volatile phase effects have been evaluated for T. urticae (LD50 = 25.1 ± 1.1 μg/mL for 24 h) and for C. lataniae (LD50 = 6.6 ± 0.5 μg/mL for 24 h, and LD50 = 2.7 ± 0.6 μg/mL for 48 h), whose values are in the same order of magnitude as the enzymatic activity. These results show the susceptibility of T. urticae and C. lataniae species to the AChE inhibitory activity. Thus, the mortality of these species may be due to the neurotoxic mode of action, which affect the transport of ions and AChE. Furthermore, L. origanoides essential oil has shown a moderate larvicidal potential with LD50 = 187.3 ± 0.9 μg/mL after 24 h. The occurrence of the larvicidal activity at very large concentration indicates that the larval mortality may occurs by ingestion or contact. The present study clearly illustrates the efficacy of the investigated essential oil as a natural pest controlling agent.

Hylocereus lemairei (Hook.) is a plant popularly known as pitaya-purple, whose fruits are known as dragon fruit. This paper aimed to carry out the physical-chemical and chemical characterization of fermented beverages based on H. lemairei fruits. Fermented beverages were elaborated using two different commercial yeasts of Saccharomyces cerevisiae [Biolievito Bayanus (BB) and Arom Cuvée (AC)] and were characterized by NMR. In addition, the antioxidant capacity (DPPH and ABTS) and Total Phenolic Content (TPC) based on the Folin Ciocalteu method were determined. According to the legislation, the fermented beverages from BB and AC showed alcoholic levels of 12.9 and 12.5% (v/v) and pH of 3.9 and 3.8, respectively. The chemical compounds of both beverages were similar, whose major organic compounds are glycerol, myo-inositol, tyrosol, and citric and succinic acids. According to the DPPH and TPC evaluation, BB beverage (248.3 µM TE and 117.6 mg GAE L-1) presented higher antioxidant capacity when compared to the BC beverage (219.8 µM TE and 108.4 mg GAE L-1). In the ABTS assay, both beverages were not statistically different (p < 0.05). Tyrosol may be responsible for increasing the antioxidant capacity and phenolic compounds content when compared to the control juice used to prepare fermented beverages. Hylocereus lemairei (Hook.) es una planta conocida popularmente como pitaya-púrpura, cuyos frutos se conocen como fruta del dragón. Este trabajo tuvo como objetivo realizar la caracterización físico-química y química de bebidas fermentadas a base de frutos de H. lemairei. Las bebidas fermentadas fueron elaboradas utilizando dos levaduras comerciales diferentes de Saccharomyces cerevisiae [Biolievito Bayanus (BB) y Arom Cuvée (AC)] y se caracterizaron por RMN. Además, se determinó la capacidad antioxidante (DPPH y ABTS) y el Contenido Fenólico Total (TPC) por el método de Folin Ciocalteu. Según la legislación, las bebidas fermentadas de BB y BC presentaron parámetros físico-químicos con niveles alcohólicos de 12,9 y 12,5% (v/v) y pH de 3,9 y 3,8, respectivamente. Los compuestos químicos de las bebidas elaboradas fueron similares, cuyos principales compuestos orgánicos son glicerol, mioinositol, tirosol, ácidos cítrico y succínico. Según la evaluación de DPPH y TPC, la bebida BB (248,3 µM TE y 117,6 mg GAE L-1) fue más alta en comparación con la bebida BC (219,8 µM TE y 108,4 mg GAE L-1). En el ensayo ABTS, estas bebidas no fueron estadísticamente diferentes (p

Background: The encapsulated essential oils (EOs) of Piper aduncum L. and Piper hispidinervum C. DC. in gelatin nanoparticles were evaluated against Aedes aegypti Linn., Tetranychus urticae Koch and Cerataphis lataniae Boisd.; Results: Encapsulation efficiency of the EOs was measured for absolute concentrations of 500 µg mL-1 (79.2 and 72.7%) and 1000 µg mL-1 (84.5 and 82.2%). The loaded nanoparticles were nearly spherical and well dispersed. The nanoparticles loaded with P. hispidinervum EO had an average size of 100 ± 2 nm, while the nanoparticles containing P. aduncum EO ranged from 175 ± 4 to 220 ± 4 nm. According to zeta potential analysis, the nanoparticles loaded with P. hispidinervum and P. aduncum EOs presented values around -43.5 ± 3 and -37.5 ± 2 mV respectively. The controlled release of EOs was described by the anomalous mechanism of Korsmeyer-Peppas. Both encapsulated EOs reached lethal dosages within 24 h of exposure and total mortality of the tested pests.; Conclusion: The present work successfully developed gelatin-based nanoparticles that served as carriers for the EOs of P. aduncum and P. hispidinervum to be applied as a sustainable control tool of A. aegypti, T. urticae and C. lataniae. The developed loaded nanoparticles presented high encapsulation efficiency and EO concentration release higher than lethal dosages. This indicates that it is feasible to use gelatin-based nanoparticles loaded with P. aduncum and P. hispidinervum EOs to control the tested pests. © 2018 Society of Chemical Industry.; © 2018 Society of Chemical Industry.

The “araca-pera” (Psidium acutangulum DC) is an exotic guava consumed by the Brazilian Amazon population. This paper describes 22 compounds from this fruit by UHPLC–HRMS and NMR methods, being one disaccharide, five monosaccharides, two organic acids, one trihydroxycinnamic acid glucopyranosyl, one tannine digalloyl glucopyranosyl, five triterpenoid acids, and six fatty acids. It also quantifies the level of ascorbic acid (AA) by HPLC–MS (74.32 ± 1.23 mg/100 g of fresh fruit), and defines the chemical antioxidant activities by DPPH and ABTS+ assays (24.96 ± 0.75, 90.57 ± 0.63 mg of vitamin C/100 g fresh fruit, respectively), and a cell-based assays (76–100%). These results have shown that this exotic guava can be consumed as a nutraceutical ingredient, as well as be used in the production of functional foods in the Amazonian diet to prevent chronic and oxidative diseases.

Acai, a native palm fruit, is one of the most popular functional foods in Amazon and it is highly perishable. The alcoholic fermentation is an efficient preservation process and the wine production could be an alternative to add technology to native acai. In this paper, it is reported the chemical and sensorial characterization of a novel alcoholic beverage produced with acai from different regions of the Amazonas state. The physicochemical characterization of wines was determined by basic parameters, color by CIELab model, methanol quantification by headspace GC-FID, antioxidant potential by DPPH and ABTS, total phenol content, chemical profiles by NMR assisted by multivariate methods and sensory evaluation by a scorecard including visual, aromatic and gustative attributes. Among all samples analyzed, the alcoholic beverages produced with acai from Codajas, Carauari and Barcelos regions located in the Amazonas state, stood out in relation to all parameters analyzed.

Essential oils still remain as a source for the identification of promising biologically active molecules. The aim of this study was to determinate the chemical composition of essential oils from Eugenia cuspidifolia (EO1) and Eugenia tapacumensis (EO2), and their antiproliferative effects in human cancer cell lines. The essential oils were analyzed using gas chromatography (GC) and gas chromatography-mass spectrometry (GC–MS). Evaluation of cytotoxic effect was performed against different tumor line cells was performed through alamar blue assay, using different human cell line: malignant melanoma (SK-MEL-19), colorectal carcinoma (HCT116), breast adenocarcinoma (MCF7), gastric adenocarcinoma (ACP02). Subsequently, clonogenic survival, wound-healing assay, activity of metalloproteinases (MMPs), and comet assays were executed using only the more sensibility cell line to oils. A total of 24 different compounds were identified in the essential oils; the major components were caryophyllene oxide (57.46%, 55.95%) and α-copaene (3.75%, 13.67%) were the majority of detected compounds in both oils from EO1 and EO2, respectively. Essential oils reduce viability of tumor cells (MCF-7, HCT116, SK-Mel 19), according with values of IC50 between 12.37–26.17 μg mL−1. Essential oils showed high cytotoxic potential against HCT116 cell line, therefore this cell strain was selected for evaluation of anticancer potential. The EO1 and EO2 showed a reduction in cell colony formation, cell migration, and MMPs (MMP-2 and MMP-9) activities. In the comet assay, a high damage index was identified for EO2. In conclusion, the essential oils from these two Eugenia species analyzed have shown promising antitumoral results, with potential effect in HCT116 cell line.

Biflavones, a chalcone-flavone, and a tetraflavonoid with a new carbon skeleton were isolated from the leaves of Aristolochia ridicula. Their structures were determined by chemical derivatizations and spectrometric analyses.

Made available in DSpace on 2013-08-12T17:55:10Z (GMT). No. of bitstreams: 0 Previous issue date: 2009-01-01 Made available in DSpace on 2013-09-30T19:09:43Z (GMT). No. of bitstreams: 0 Previous issue date: 2009-01-01 Submitted by Vitor Silverio Rodrigues (vitorsrodrigues@reitoria.unesp.br) on 2014-05-20T14:20:06Z No. of bitstreams: 0 Made available in DSpace on 2014-05-20T14:20:06Z (GMT). No. of bitstreams: 0 Previous issue date: 2009-01-01 Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Fourteen compounds were isolated from Aristolochia giberti. These included a new triterperne, (-)-onocera-8,8'-diol. In addition, 3-hydroxypropanoate, acetate, and formate were detected by NMR techniques, which suggests that they are derivatives from 2-butynedioate, which is not detected by (1)H NMR. GC-MS and chemometric analyses of essential oils from stems and leaves showed great similarity between this cultivated species in Brazil and that in Argentina, which allowed us to confirm the species identity and to differentiate the oils according to the plant parts. Univ Estadual Paulista, Inst Quim, BR-14801970 Araraquara, SP, Brazil Univ Estadual Paulista, Inst Quim, BR-14801970 Araraquara, SP, Brazil

Biflavones and a chalcone-flavone tetramer were isolated from the leaves of Aristolochia ridicula, together with proto-quercitol. Their structures were determined by spectroscopic methods.