In recent years, there has been great interest in understanding the chemistry of natural products from different organisms and their role in ecological processes. Some species of frogs sequester and metabolize dietary alkaloids obtained primarily from mites and ants as chemical defense. Most of these studies have employed gas chromatography techniques coupled with mass spectrometry, which restricts the possibility of observing more polar metabolites. In the case of pumiliotoxin (+)-251D and allopumiliotoxin (+)-267A, the fragmentation mechanisms in electrospray ionization systems with collision-induced fragmentation are undescribed. The present study aims to elucidate the fragmentation pathways of these two toxins. For this purpose, we used direct infusion of toxins in a time-of-flight hyphenated quadrupole electrospray ionization tandem mass spectrometry (ESI-MS/MS) system. Different collision energies were applied, and the data rationalized from the concepts of reaction mechanisms. The joint analysis allowed to present a robust map of fragmentation opening perspectives for their application in studies of the occurrence of new polar analogues.

Caves are ecosystems and natural heritage sites with magnificent biological diversity, from microorganisms to animals, despite their selective environment for development and survival. Until now, studies on cave microbiomes have included taxonomic classification through metagenomics analysis, demonstrating microbiological heterogeneity mainly composed of prokaryotic organisms or bacteria species. The generally oligotrophic environment, with limited energy input and dark zone, is the main feature differentiating the cave microorganisms from the other microbiomes and resulting in a unique habitat, which has unexplored regard to biology and chemical diversity. Multi-omics integration is a key strategy for scanning and integrating the macro and micromolecular universe, providing a better comprehension of processes and answers of the microbiome in natural cavities. Here, we highlight the strategies employed to study the cave microbiome, from the microbial genomes to their ability to secondary metabolites production, and also the multi-omics integration to explore the chemical and biological diversity in caves. animals survival now analysis species zone habitat Multiomics Multi omics universe cavities Here production multiomics multi caves

This is an initial study using infrared (IR) in silico data as a standard database in preliminary method for new synthetic seized drugs. For this purpose, ten of the most common synthetic illicit seized substances on the Brazilian market were compared and computational chemistry was used as a tool for theoretical standard database. Infrared data from standard electronic library, experimental data from seized samples and data simulated by Density Functional Theory (DFT) were evaluated. The feasibility of the method was based on the degree of correlation of evaluated data. The results suggest that the computational methodology can be a viable way to analyze the structures of new synthetic drugs and obtain preliminary infrared profiles. Correlations data indicated a presumptive identification of the analyzed samples and it was also possible to observe a preliminary identification of drugs in five classes. However, it was observed that some synthetic cathinones and phenylethylamines were confused with amphetamines. Therefore, new studies must be developed to optimize the use of these data, because the simulated IR spectra can be advantageous to evaluate the profile of possible substances that may be synthesized in the future. (IR purpose library DFT (DFT profiles classes However amphetamines Therefore future

Various beneficial biological activities have been reported for passion fruit (Passiflora edulis), grown in tropical and subtropical regions. However, no study has yet demonstrated its action against the Zika virus (ZIKV) infection. The present study aimed to investigate the anti-ZIKV of the ethanolic passion fruit seed extract (PFSE), from which, liquid chromatography tandem mass spectrometry (LC-MS/MS) analysis allowed to putatively annotate the occurrence of piceatannol, astringin, scirpusin A, scirpusin B, isookanin-7-O-glucoside and naringenin-7-O-glucoside, two quadranguloside derivatives, tyrosine, and phenylalanine. PFSE is well tolerated by cell lines (Vero E6 and HTR-8/SVneo) and tissue explants from the human placenta. With 1- and 24-h treatments, PFSE consistently reduced the viral load and NS1 protein expression of the two strains of ZIKV (MR766 and PE243) in placental explants and cell lines. Thus, PFSE has a promising potential for developing anti-ZIKV treatments, protecting the placenta against infection caused by ZIKV, along with relevant antioxidant potential, represented by ferric reducing antioxidant power (FRAP) of 390.5 Trolox eq per g dry extract and half maximal inhibitory concentration (IC50) for 2,2-diphenyl-1-picrylhydrazyl radical (DPPH•) of 12.1 µg mL-1, and more than 90% protection from lipid peroxidation. Although further studies need to be conducted, PFSE treatment was safe and effective in trophoblast cells and placental explants, thus representing a promising class of all-accessible products based on the reuse of industrial by-products.

The recent emergence of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) has led society to live with a serious public health problem. In this sense, repositioning of antiretrovirals has captured the attention of the scientific community. Tenofovir disoproxil fumarate (TDF) is an antiretroviral compound that is used to treat acquired immune deficiency syndrome (AIDS) and hepatitis B. In this short report, we present a scale-up investigation of TDF by in situ infrared spectroscopy monitoring and a forced degradation study to describe a new degradation product. Finally, we have evaluated TDF in vitro for SARS-CoV-2 for the first time foreseeing the using of this medicine in pre-clinical and clinical investigations for the COVID-19 (coronavirus disease 2019) treatment.

Metabolomics has played a central role in various areas of plant sciences, offering new perspectives for the advancement of agriculture, drug discovery, chemical ecology and taxonomy. Plant metabolomics (identification and quantification) aims to understand the relationship between biological systems and genetic, pathological and or environmental stimuli in terms of differential expression of the metabolism. Owing to the unique challenges, such studies require multidisciplinary skills involving biology, chemistry, statistics, and computer science for the extraction and complete understanding of information. In this sense, this review summarizes the main procedures that involve the steps of plant metabolomic study (design of experiments, sample preparation, analytical methods and data analysis), providing a comprehensive overview, showing the main challenges and limitations and possible solutions for the different approaches used.

A Streptomyces sp. (BRA-384) was selected among nine strains of bacteria isolated from the zoanthids Palythoa caribaeorum due to the high cytotoxic activity presented by its EtOAc extract (inhibitory concentration mean (IC50) of 2 ng mL-1) against colon cancer cell line. From the EtOAc extract of BRA-384 three new chemical entities (A6, A7 and A8) and one dextrorotatory chromomycin (A5), a promising class of anticancer compounds, were identified. The cytotoxicity of chromomycins A5 to A8 was tested against five tumor cell lines (HCT 116 (human colon adenocarcinoma), MCF-7 (human breast carcinoma), PC-3M (human metastatic prostate cancer), 501-mel (human metastatic melanoma) and MM200 (metastatic melanoma)). All chromomycins were highly potent showing IC50 values from 0.2 to 133 nM. Chromomycin A5 was consistently the most potent over all tested cells (IC50 values from 0.2 in MM200 to 7.9 nM in PC-3M), inclusive when compared to the standard chemotherapeutic agent doxorubicin, that presented IC50 values ranging from 147 to 568 nM against MM200 and MCF-7, respectively.

ABSTRACT Erythraline is the major alkaloid produced by Erythrina verna Vell., Fabaceae, a plant used in folk medicine and phytotherapeutic products to treat anxiety and sleep disorders. This study aimed to investigate the pharmacokinetic parameters of erythraline after intravenous administration in rats. For the analysis of erythraline in rat plasma, a method was developed and validated using UHPLC-MS/MS. Pharmacokinetic parameters were estimated by non-compartmental analysis. The metabolite 8-oxo-erythraline observed in previous biomimetic model studies was monitored during in vivo experiments. The quantification limit was 5 ng/ml within a linear range of 5-2000 ng/ml. After an intravenous dose of 1 mg/kg, the following pharmacokinetic parameters were observed: elimination half-life of 44.2 min; total clearance of 42.1 ml/min/kg and volume of distribution of 2085 ml/kg. In summary, a precise, accurate and selective UHPLC-MS/MS method was developed and successfully applied to investigate the pharmacokinetics of erythraline in rats. The metabolite 8-oxo-erythraline was observed in rat plasma after 20 min of erythraline administration.

Abstract Condensed tannins have been used for many years in folk medicine to treat gastric problems. The mechanism of action that explains why tannins improve gastritis symptoms is based on their ability to chelate metals, antioxidant activity, and their complexation power with other molecules. Even though these uses are well-known, the requirements to become an herbal medicine are much more complex. Herein, we analyzed Stryphnodendron rotundifolium Mart., Fabaceae, extract using MALDI for tannin characterization and carried out a fluorescence-imaging study to prove the gastroprotective effects of tannins as coating agents. Through these methods we show that condensed tannins form a gastroprotective layer. Moreover, we revise and discuss other possible mechanisms of action for phenolic-rich plant extracts and their potential in the development of herbal medicines to treat ulcers and gastritis.

The amorphous, mesoporous SiO2-SO3H catalyst with a surface area of 115 m2 g-1 and 1.32 mmol H+ per g was very efficient for the protonation of ketones on a 10% (m/m) basis, and the catalyst-bound intermediates can be trapped by polyalcohols to produce ketals in high yields or suffer aldol condensations within minutes under low-power microwave irradiation. The same catalyst can easily reverse the ketalization reaction.

Seriniquinone is a natural quinone isolated from a rare marine bacterium of the genus Serinicoccus. This secondary metabolite has been shown to have anticancer properties, which has raised attention of the scientific community. In this short report, we present the first investigation of the gas-phase chemistry fragmentation reactions of seriniquinone in electrospray ionization tandem mass spectrometry (ESI-MS/MS), to be further applied in pharmacokinetics and metabolism studies. All the proposals herein were supported by computational chemistry.

The genus Lychnophora (Asteraceae) is a medicinal plant traditionally used as anti-inflammatory or analgesic agent. Its biological properties have been widely investigated and correlated with its chemical composition, which could be different between the species and even accordingly to the place and season of collection. In this work, it was investigated the spatial and temporal variations in the secondary metabolites from five populations of Lychnophora ericoides. Among them, a more diversified secondary metabolism was observed for the plants collected at Ibiraci-MG (Brazil), a city placed between two biomes, Cerrado and Atlantic Forest. The highest concentrations of chlorogenic acids were found in the Cerrado dry season (winter), while the flavonoids were higher during the rainy season (summer). Significant reduction was observed in the contents of all the secondary metabolites in old leaves, and also in flowery branches. These variations detected in L. ericoides leaves could highly influence the intensity of the biological activities of this plant.

ABSTRACT In general, Passiflora species have been reported for their folk medicinal use as sedative and anti-inflammatory. However, P. caerulea has already been reported to treat pulmonary diseases. Severe pulmonary tuberculosis, generally caused by Mycobacterium tuberculosis strains resistant to multiple drugs, can lead to deleterious inflammation and high mortality, encouraging new approaches in drug discovery. Thus, the aim of this work was to evaluate the Passiflora mucronata Lam., Passifloraceae, potential for tuberculosis treatment. Specifically, related to antimycobacterial activity and anti-inflammatory related effects (based on inhibition of nitric oxide, tumor necrosis factor-alpha production and antioxidant potential), as well as the chemical profile of P. mucronata. High performance liquid chromatography coupled with diode-array ultraviolet and mass spectrometer analyses of crude hydroalcoholic extract and ethyl acetate fraction showed the presence of flavonoids. Ethyl acetate fraction showed to be as antioxidant as Ginkgo biloba standard extract with EC50 of 14.61 ± 1.25 µg/ml. One major flavonoid isolated from ethyl acetate fraction was characterized as isoorientin. The hexane fraction and its main isolated compound, the triterpene β-amyrin, exhibited significant growth inhibitory activity against Mycobacterium bovis BCG (MIC50 1.61 ± 1.43 and 3.93 ± 1.05 µg/ml, respectively). In addition, Passiflora mucronata samples, specially hexane and dichloromethane fractions, as well as pure β-amyrin, showed a dose-related inhibition of lipopolysaccharide (LPS)-induced nitric oxide production. In conclusion, Passiflora mucronata presented relevant biological potential and should be considered for further studies using in vivo pulmonary tuberculosis model.

Copaiba oil, an oleoresin extracted from Copaifera genus, has been widely used in popular medicine for the treatment of several diseases. The aim of this study was to investigate the antifungal activity of the copaiba oil and its isolated compounds caryophyllene oxide, copalic acid and acetoxycopalic acid against Trichophyton rubrum, Trichophyton mentagrophytes and Microsporum gypseum strains, using microdilution method and microscopy techniques. It was found that the copaiba oil and the copalic acid were active against dermatophytes by minimal inhibitory concentration (MIC) and minimal fungicidal concentration (MFC) tests. The MIC and MFC of copaiba oil against T. rubrum, T. mentagrophytes and M. gypseum were 125 µg mL-1 (250 µg mL-1), 500 µg mL-1 (500 µg mL-1) and 250 µg mL-1 (250 µg mL-1), respectively. For copalic acid, the MIC and MFC were 50 µg mL-1 (100 µg mL-1), 100 µg mL-1 (100 µg mL-1) and 50 µg mL-1 (100 µg mL-1), respectively. Fluorescence microscopy and scanning electronic microscopy were used to investigate inhibition on hyphal growth by compounds, copaiba oil and copalic acid, showing a strong inhibition and an irregular growth pattern. Cell wall, cytoplasmic membrane and intracellular contents were also damaged. In conclusion, copaiba oil and copalic acid showed great activity against dermatophytes, being potential compounds for the development of antifungal drugs.

ABSTRACT Phoradendron mucronatum and P. microphyllum are plants that found in tropical and subtropical areas, used in traditional medicine and popularly known as mistle-thrush. The aim of this study was to identify the chemical constituents of different leaf extracts from P. mucronatum and P. microphyllum and assess cytotoxic activity against strains from a human tumour cells. Extracts obtained with hexane, dichloromethane, chloroform and ethyl acetate from the leaves were analysed by gas chromatography coupled with mass spectrometry (GC-MS) and the cytotoxicity was assessed by the MTT method (bromide (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide)). The tested human tumour cells were NCI-H292 (human pulmonar mucoepidermoid carcinoma), MCF-7 (human breast adenocarcinoma) and HEp-2 (epidermoid carcinoma of the larynx). Analysis by GC/MS of the extracts from leaves of P. microphyllum and P. mucronatum detected 51 different compounds, such as alkaloids, diterpenes, triterpenes, sterols, alcohols, aldehydes, fatty acids and hydrocarbons. In the cytotoxic evaluation, hexane and ethyl acetate extracts from the leaves P. microphyllum inhibited cell growth of NCI-H292 strains (72.97%) and HEp-2 (87.53%), respectively. The extracts of P. mucronatum species showed an inhibitory effect towards NCI-H292 (83.19%/hexane), MCF-7 (88.69%/dichloromethane) and HEp-2 (93.40%/hexane). The extracts showed cytotoxic activity against the tested strains, especially the P. mucronatum, which presented the highest percentages of inhibition of cell growth.