Lantana caatingensis Moldenke (Verbenaceae) is an endemic plant from northeastern Brazil. However, its chemical composition is almost unknown. This study aimed to characterize the chemical compounds found in L. caatingensis and investigate the antileishmanial potential of its hydroalcoholic extract and polar fractions. Compounds present in the hydroalcoholic extract obtained from L. caatingensis leaves and its polar fractions (ethyl acetate and methanolic) were analyzed by liquid chromatography with a photodiode-array detector coupled to electrospray ionization quadrupole time-of-flight mass spectrometry. An antileishmanial assay was performed in a 96-well plate against Leishmania major promastigotes using resazurin on a plate spectrophotometer and the results were expressed as percentage of growth inhibition. Nine compounds were determined in the investigated extract and fractions, classified as flavonoids, flavonoid C-glycosides and phenylethanoid glycosides. The antileishmanial activity revealed that the hydroalcoholic extract and the ethyl acetate fraction were active against L. major promastigotes with inhibitory concentration of 71.78 and 26.86 µg mL-1, respectively, while the methanolic fraction was inactive (478.40 µg mL-1). This is the first report on the chemical composition and antileishmanial activity of L. caatingensis extracts. These results contribute to further knowledge of species belonging to the Lantana genus. Verbenaceae (Verbenaceae Brazil However unknown L photodiodearray photodiode array timeofflight time flight spectrometry 96well well 96 inhibition flavonoids Cglycosides C glycosides 7178 71 78 71.7 2686 26 86 26.8 mL1, mL1 mL 1, 1 mL-1 respectively 478.40 47840 478 40 (478.4 mL1. . mL-1) extracts genus 9 717 7 71. 268 2 8 26. mL- 478.4 4784 47 4 (478. 478. (478 (47 (4 (

Parthenolide (PTN) is a secondary metabolite of the plant Tanacetum parthenium (L.) Schulz Bip. and is considered the chemical marker of this species. This sesquiterpene lactone (germacrene skeleton) has been described as responsible for the biological activity of the leaf extract. In addition, several studies in the literature have demonstrated its antiparasitic and antineoplastic activity. However, there is a need for knowledge of other safety parameters, such as pharmacokinetic, pharmacodynamic and toxicity evaluations. Therefore, in this investigation, the in vitro metabolism of parthenolide was performed with rat liver microsomes and biomimetic metabolism (such as cytochrome P-450 system) using organometallic catalysts. The biomimetic procedure was validated since the major compound of biomimetic oxidative reaction with meta-chloroperbenzoic acid catalyzed by metalloporphyrin 5,10,15,20-tetrakis(pentafluorophenyl)-porphyrin iron(III) chloride was also observed with rat liver microsomes. Previous chemoenzymatic synthesis studies of PTN afforded the same epoxide formation, this major oxidative compound was isolated and fully characterized as (1 R,10R)-epoxyparthenolide based on experimental and theoretical calculations of infrared (IR) and vibrational circular dichroism (VCD) data at the B3PW91/6-311G. Furthermore, for the first time, this metabolite was evaluated for trypanocidal and leishmanicidal activity. The mean inhibitory concentration (IC50) values were lower for PTN than its metabolite and showed significant cytotoxic effects for both parasites. This finding holds promise for addressing neglected diseases. (PTN L. L (L. Bip species germacrene skeleton extract addition However parameters pharmacokinetic evaluations Therefore investigation P450 P 450 P-45 system catalysts metachloroperbenzoic meta chloroperbenzoic 5,10,15,20tetrakispentafluorophenylporphyrin 5101520tetrakispentafluorophenylporphyrin tetrakispentafluorophenylporphyrin 5,10,15,20 tetrakis pentafluorophenyl porphyrin 5 10 15 20 ironIII iron III iron(III formation 1 ( R,10Repoxyparthenolide R10Repoxyparthenolide RRepoxyparthenolide R,10R epoxyparthenolide R 10R IR (IR VCD (VCD B3PW91/6311G. B3PW916311G BPWG B3PW91/6 311G. B3PW91 6 311G B PW G B3PW91/6-311G Furthermore time IC50 IC (IC50 parasites diseases (L P45 45 P-4 20tetrakispentafluorophenylporphyrin 5101520 5,10,15,2 2 10Repoxyparthenolide Repoxyparthenolide R10R RR 6311G B3PW91/6311G B3PW916 BPW B3PW91/ B3PW9 IC5 (IC5 P4 4 P- 510152 5,10,15, B3PW (IC 51015 5,10,15 5101 5,10,1 510 5,10, 51 5,10 5,1 5,

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

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. years processes defense metabolites +251D 251D D + +267A, 267A A 267A, (+)-267A collisioninduced induced undescribed purpose timeofflight time flight ESIMS/MS ESIMSMS ESI MS/MS MS (ESI-MS/MS system applied analogues +267A ESIMS MSMS

Plectranthus amboinicus is an aromatic herb often used in traditional medicine due to its antimicrobial properties. Based on it, the present study aimed to assess the toxic, antioxidant and, antibacterial properties of P. amboinicus essential oil (EO) either separated or mixed into fish feed. The chemical composition of the EO was also investigated. All samples were prepared with over 50% of carvacrol. The results revealed that the EO is a weak antioxidant and highly toxic against Artemia salina, showing greater antibacterial activity than positive control of chloramphenicol and synergistic effects. The EO also presented high antimicrobial activity against Aeromonas hydrophila strains when free or feed-incorporated, thus being a promising product for the treatment of opportunistic infections in fish. it P (EO feed investigated 50 carvacrol salina effects feedincorporated, feedincorporated incorporated, incorporated feed-incorporated 5

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.

MOLECULAR NETWORKS: AN ANALYSIS ON ANNOTATIONS AND DISCOVERY OF NEW ASSETS. To speed up the discovery of bioactive natural products (NP), chemists have sought advanced approaches in analytical and computational chemistry in attempt to organize and extract information from large data sets. In this sense, the molecular networks (MN) successfully organized enormous sets of mass spectrometry (MS) data together with samples metadata information in an intuitive visualization in the spectral similarity networks format. GNPS (Global Natural Products Social Molecular Networking), a free online platform for storing and processing MSn data, is a leading application of spectral matching with public databases aimed at the dereplication and discovery of new bioactive products through molecular networks. In this review, we address the concept of GNPS spectral similarity networks, as well as their complementary computational tools, benefits and limitations applied in NP studies associated with dereplication, chemical ecology, functional genetics and determination of biosynthetic pathways.

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.

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.

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.

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.