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Background: The Atlantic Forest is one of the most diverse and threatened phytogeographical domains in the world. Despite that, it includes regions with poor floristic knowledge, even in protected areas. Although the importance of protected areas in conserving the Atlantic Forest hotspot is undisputed, it is necessary to recognise the floristic richness of these areas to propose effective conservation actions. In this sense, online databases have proved to be a promising tool for compiling species lists with relevant biodiversity information. This study is based on the list of vascular plants of the "Parque Estadual da Pedra Selada", published in the "Catálogo de Plantas das Unidades de Conservação do Brasil". It summarises the species richness, endemism and conservation status of this protected area., New Information: The published list of vascular plants was based on data obtained from herbarium collections available in online databases. A total of 303 species have been recorded for the "Parque Estadual da Pedra Selada," of which 297 are native to Brazil, 78 are endemic to the Brazilian Atlantic Forest, and seven are endemic to the State of Rio de Janeiro. More than 60% of the species are woody, and more than 40% are trees. Eight threatened species (Endangered - EN and Vulnerable - VU), of which five are endemic to the State of Rio de Janeiro, are housed in this protected area. One species was classified as Data Deficient (DD). Our results increase the knowledge of the Atlantic Forest flora in the State of Rio de Janeiro and support effective conservation planning for this protected area., (Isabela Maciel Waga, Andrea Ferreira da Costa, Claudine Massi Mynssen, Eduardo Pinheiro Fernandez, Elsie Franklin Guimarães, Fernanda Saleme, George Azevedo de Queiroz, Guilherme Medeiros Antar, Haroldo Cavalcante de Lima, Hemily Oliveira Marques, Lara Serpa Jaegge Deccache, Leandro Jorge Telles Cardoso, Leandro Lacerda Giacomin, Maria Regina de V. de Vasconcellos Barbosa, Mario Gomes, Marli Pires Morim, Otávio Luis Marques da Silva, Pedro Fiaschi, Pedro Luís Rodrigues de Moraes, Rafaela Campostrini Forzza, Renon Santos Andrade, Thaís Andrade Ferreira Dória, Thiago Serrano de Almeida Penedo, Thuane Bochorny, Marcio Verdi.)

Background: The "Serra da Concórdia" is part of the Atlantic Forest phytogeographical domain in the Brazilian state of Rio de Janeiro and it has a predominant phytophysiognomy of Semideciduous Seasonal Forest. This region underwent intense habitat loss and fragmentation during the 19 th century, due to coffee plantations and later pastures. With the decline of these activities, the areas were abandoned, triggering secondary succession. In 2002, the "Parque Estadual da Serra da Concórdia" was established in this region to preserve the remaining forest fragments. The updated list of vascular plants recorded in this protected area, published in the "Catálogo de Plantas das Unidades de Conservação do Brasil", is presented here, along with information on richness, endemism, and conservation status., New Information: The "Parque Estadual da Serra da Concórdia" houses 231 vascular plant species, of which 90% are angiosperms, 10% ferns and lycophytes, and 27% endemic to the Atlantic Forest. Ten species are threatened with extinction, three are categorized as Endangered, and seven as Vulnerable. Although there have been expeditions in the "Parque Estadual da Serra da Concórdia", they have been limited, resulting in a low number of records and the species richness for a protected area. This is notable considering the 2,130 Brazilian native vascular plant species recorded in the semideciduous seasonal forest of Rio de Janeiro. Our data indicates that floristic inventories of Brazilian protected areas could help highlight gaps in flora knowledge and support the proposal of effective conservation actions., (Lara Serpa Jaegge Deccache, Claudine Massi Mynssen, Claudio Nicoletti de Fraga, Eduardo Pinheiro Fernandez, Elsie Franklin Guimarães, Elton John de Lírio, Fabiana Luiza Ranzato Filardi, Fernanda Ribeiro de Mello Fraga, Fernanda Saleme, Gustavo Hiroaki Shimizu, Haroldo Cavalcante de Lima, Helen Ayumi Ogasawara, Hemily Oliveira Marques, Isabela Maciel Waga, Isabella Cristina de Castro Silva, Jenifer de Carvalho Lopes, Leonardo Biral, Lucas Vieira Lima, Maria Liris Barbosa, Mario Gomes, Massimo Giuseppe Bovini, Miriam Kaehler, Nádia Roque, Otávio Luis Marques da Silva, Pedro Luís Rodrigues de Moraes, Rodrigo Lopes Borges, Ronaldo Marquete, Thuane Bochorny, Thiago Fernandes, Marcio Verdi.)

This study evaluates the essential oil (EO) composition of Piper rivinoides Kunth, a shrub native to the Brazilian tropical rainforest, across different plant parts and developmental phases. The aim was to explore the chemical diversity of EO and its reflection in the plant's ecological interactions and adaptations. Plant organs (roots, stems, branches, and leaves) at different developmental phases were subjected to hydrodistillation followed by chemical analysis using Gas Chromatography-Mass Spectrometry (GC-MS) and Gas Chromatography-Flame Ionization Detector (GC-FID). The results revealed a relevant variation in EO yield and composition among different plant parts and developmental phases. Leaves showed the highest yield and chemical diversity, with α-pinene and β-pinene as major constituents, while roots and stems were characterized by a predominance of arylpropanoids, particularly apiol. The chemical diversity in leaves increased with plant maturity, indicating a dynamic adaptation to environmental interactions. The study underscores the importance of considering the ontogeny of plant parts in understanding the ecological roles and potential applications of P. rivinoides in medicine and agriculture. The findings contribute to the overall knowledge of Piperaceae chemodiversity and ecological adaptations, offering insights into the plant's interaction with its environment and its potential uses based on chemical composition.

Piper mollicomum Kunth (Piperaceae) plays a vital role in the preservation of the Brazilian Atlantic Forest by contributing to the regeneration of deforested areas. Recent scientific investigations have analyzed the chemical constituents and seasonal dynamics of essential oils (EO) from various Piper L. species, highlighting the need to elucidate their chemical-ecological interactions. This study aims to expand the chemical-ecological knowledge of this important taxon in neotropical forests, using P. mollicomum as a model. The methodologies employed include the collection of plant material, EO extraction by hydrodistillation, analysis of EO by gas chromatography-mass spectrometry (GC-MS) and gas chromatography-flame ionization detector (GC-FID), recording the frequency of visits by potential pollinators and microclimatic variables, and by conducting calculations of chemodiversity and chemophenetic indices. Chemical analyses indicated that the diversity of EO and environmental factors are linked to the activities of potential pollinators. In the Tijuca Forest, P. mollicomum revealed significant interactions between its volatile constituents and microclimatic variables, showing that the chemodiversity of the leaves and reproductive organs correlates with pollinator visitation. Additionally, a notable difference in chemical evenness was observed between these vegetative structures. The chemophenetic indices by Ramos and Moreira also revealed correlations with chemical diversity.

Piper aduncum L. is widely distributed in tropical regions and the ethnobotanical uses of this species encompass medicinal applications for the treatment of respiratory, antimicrobial, and gynecological diseases. Chemical studies reveal a diverse array of secondary metabolites, including terpenes, flavonoids, and prenylated compounds. Extracts from P. aduncum have shown antibacterial, antifungal, and larvicidal activities. Our study explores the activity of extracts and partitions against Mycobacterium tuberculosis H37Rv, as well as the chemical diversity of the bioactive partition. This marks the first investigation of the bioactive partition of P. aduncum from agroecological cultivation. The ethyl acetate partition from the ethanolic leaf extract (PAEPL) was found to be the most active. PAEPL was subjected to column chromatography using Sephadex LH-20 and the obtained fractions were analyzed using UHPLC-HRMS/MS. The MS/MS data from the fractions were submitted to the online GNPS platform for the generation of the molecular network, which displayed 1714 nodes and 167 clusters. Compounds were identified via manual inspection and different libraries, allowing the annotation of 83 compounds, including flavonoids, benzoic acid derivatives, glycosides, free fatty acids, and glycerol-esterified fatty acids. This study provides the first chemical fingerprint of an antimycobacterial sample from P. aduncum cultivated in an agroecological system.

Microbial resistance, caused by the overuse or inadequate application of antibiotics, is a worldwide crisis, increasing the risk of treatment failure and healthcare costs. Plant essential oils (EOs) consist of hydrophobic metabolites with antimicrobial activity. The antimicrobial potential of the chemical diversity of plants from the Atlantic Rainforest remains scarcely characterized. In the current work, we determined the metabolite profile of the EOs from aromatic plants from nine locations and accessed their antimicrobial and biocidal activity by agar diffusion assays, minimum inhibitory concentration, time-kill and cell-component leakage assays. The pharmacokinetic properties of the EO compounds were investigated by in silico tools. More than a hundred metabolites were identified, mainly consisting of sesqui and monoterpenes. Individual plants and botanical families exhibited extensive chemical variations in their EO composition. Probabilistic models demonstrated that qualitative and quantitative differences contribute to chemical diversity, depending on the botanical family. The EOs exhibited antimicrobial biocidal activity against pathogenic bacteria, fungi and multiple predicted pharmacological targets. Our results demonstrate the antimicrobial potential of EOs from rainforest plants, indicate novel macromolecular targets, and contribute to highlighting the chemical diversity of native species.

The aim of this study was to monitor the volatile chemical composition from leaves and reproductive organs of Piper mollicomum Kunth (PM), in its reproduction period, as well as register inflorescence visitors, microclimate and phenological information. The essential oils (EOs) obtained from the different fresh organs by hydrodistillation were identified and quantified by Gas Chromatography/Mass Spectrometry (GC/MS) and by GC coupled to a Flame Ionization Detector (GC/FID), respectively. The cercentage content of some volatiles present in reproductive organs, such as limonene, 1,8-cineole, linalool and eupatoriochromene, increased during the maturation period of the inflorescences, and decreased during the fruiting period, suggesting a defense/attraction activities. Furtermore, a biosynthetic dichotomy between 1,8-cineole (leaves) and linalool (reproductive organs) was recorded. A high frequency of bee visits was registered weekly, and some correlations showed a positive relationship between this variable and terpenes. Microclimate has an impact on this species' phenological cycles and insect visiting behavior. All correlations between volatiles, insects, phenology and microclimate allowed us to present important data about the complex information network in PM. These results are extremely relevant for the understanding of the mechanisms of chemical-ecological plant-insect interactions in Piperaceae, a basal angiosperm.

This study tested the hypothesis that "clonal chemical heritability is a crucial factor for the conservation of chemical uniformity of Piper essential oils in controlled monoclonal cultivation". We asexually propagated first and second-generation clones of two medicinal and aromatic species, Piper gaudichaudianum Kunth and Piper mollicomum Kunth (Piperaceae), for use as experimental models since they show high chemical plasticity in the wild. Leaves from wild specimens of both species, and their respective cultivated specimens, were hydrodistilled in a Clevenger-type apparatus to produce essential oils (EOs). EOs were chemically characterised by GC-MS and GC-FID. The analysis identified 63 compounds in EO of P. mollicomum , which were predominantly monoterpenes, and 59 in EO of P. gaudichaudianum , which were predominantly sesquiterpenes. Evaluation of chemical diversity and oxi-reduction indices showed a loss of chemical homology across the intergenerational cline. Chemometric analysis indicated higher chemical plasticity between wild and intergenerational specimens of P. mollicomum , than for P. gaudichaudianum . EO compounds were significantly less oxidized throughout the generations in both species. Therefore, while clonal heritability is crucial to chemical homology, significant chemical plasticity is likely to occur when cultivated from wild specimens.

Oral squamous cell carcinoma (OSCC) is the most common type of head and neck malignancy. Research on essential oils (EOs) has shown important cytotoxic and anti-tumor properties, among others. Piperaceae species are rich in EOs and here we highlight Piper rivinoides Kunth. We investigated the crude EOs from P. rivinoides , their pure major constituents and an enriched fraction with the main EO compounds (EF) as cytotoxic and selective OSCC agents. EOs presented as main compounds (-)-α-pinene, (-)-β-pinene and limonene. EOs showed an IC 50 lower than all isolated compounds, except for (-)-β-pinene in OSCC cells. The (-)-β-pinene induced cell death with apoptotic characteristics. Commercial standards showed greater selectivity than EOs, and (-)-β-pinene was the most selective among them. EF showed higher selectivity compared to crude EOs and carboplatin, turning it into a good candidate as an anticancer fraction. These results are important for the possible development of new treatments for OSCC.

The Piper species are a recognized botanical source of a broad structural diversity of lignans and its derivatives. For the first time, Piper tectoniifolium Kunth is presented as a promising natural source of the bioactive (-)-grandisin. Phytochemical analyses of extracts from its leaves, branches and inflorescences showed the presence of the target compound in large amounts, with leaf extracts found to contain up to 52.78% in its composition. A new HPLC-DAD-UV method was developed and validated to be selective for the identification of (-)-grandisin being sensitive, linear, precise, exact, robust and with a recovery above 90%. The absolute configuration of the molecule was determined by X-ray diffraction. Despite the identification of several enantiomers in plant extracts, the major isolated substance was characterized to be the (-)-grandisin enantiomer. In vascular reactivity tests, it was shown that the grandisin purified from botanical extracts presented an endothelium-dependent vasorelaxant effect with an IC 50 of 9.8 ± 1.22 μM and around 80% relaxation at 30 μM. These results suggest that P. tectoniifolium has the potential to serve as a renewable source of grandisin on a large scale and the potential to serve as template for development of new drugs for vascular diseases with emphasis on disorders related to endothelial disfunction.

The aromatic species Piper gaudichaudianum Kunth (Piperaceae) is widely used in Brazil for medicinal and ritualistic applications. In the current study, chemophenetic patterns were realized across season and circadian rhythm based on the chemical profile of essential oils (EOs) from leaves. Hydrodistilled essential oils were analyzed by GC-MS and GC-FID, and a new calculation of metabolite oxidation level, averaged for each individual molecule component of the EO, was used to explore the patterns of metabolism/biosynthesis. This new index used an intermediate calculation, the 'weighted average redox standard' (S RO ), to enable a value for mixtures of metabolites to be generated, the 'general mixture redox index' (GM OR ). The indices were subjected to a proof-of-concept approach by making comparison to outcomes from multivariate analyses, i.e., PCA and HCA. Chemical analysis demonstrated that the essential oils were dominated by sesquiterpenes, constructed of 15 classes of compound (C-skeletons), and 4 C-skeletons were recognized in the monoterpene group, giving a total of 19. The variation of chemical profiles was distinct at different phenological stages, but stronger chemical variation was evident between day and night as compared to season. Furthermore, due to comprehensive sampling across different regions, nine chemotypes were recognized, including those previously reported. The S RO and GM RO indices demonstrate that phenological variation of chemistry is mainly an outcome of redox fluctuations in terpene biosynthesis, changing from day to night. These indices also corroborate that chemical diversity is increased with oxidative metabolism. Lastly, the current study demonstrates pronounced phenotypic plasticity in P. gaudichaudianum , which makes it a suitable candidate to help further our understanding of chemophenetics and chemical ecology.

This work aimed to evaluate the impact of different storage conditions and light and temperature exposures on the visual aspect and chemical composition of the essential oil (EO) of Piper lhotzkyanum Kunth, obtained from leaves by hydrodistillation from a region of high altitude. For this purpose, aliquots of the EO were stored for up to 90 days (a) under a refrigerator condition of 5 ± 3°C, (b) under a long-term (LT) condition of 30 ± 2°C and 75 ± 5% relative humidity (RH) and an accelerated condition (AS) of 40 ± 2°C and 75 ± 5% RH, and (c) in a photostability test achieved in amber and colorless glass vials. The changes were monitored on days 0 (control), 60, and 90 for the refrigerator, LT, and AS conditions. All EO chemical analyses were assessed by GC-FID and GC-MS for quantification and identification, respectively. It is reported, for the first time, that the EO of P. lhotzkyanum is rich in the sesquiterpenes β-elemene and α-zingiberene. No significant changes in the EO was observed, revealing a minimal impact of temperature on the sample at the different storage conditions. However, there was a change in the content of α-zingiberene to bicyclogermacrene after exposure to light. The visual appearance of the samples was altered for all test conditions except the refrigerator condition. These results can potentially contribute to the product development of a bioactive EO from leaves of P. lhotzkyanum, a sesquiterpene rich natural material.

Comparability of measurement results and their metrological traceability to the International System of Units (SI) are fundamental tools to ensure reliable decisions in the social sphere, commerce, and science. The use of appropriate references in analytical chemistry, such as certified reference materials (CRMs) of high purity substances, is one of the required procedures to obtain traceable measurements. When commercial standards with non-certified purity values are used, traceability must be achieved by determining the purity of the standard using a potential primary reference measurement procedure or other appropriate methods. Quantitative nuclear magnetic resonance (qNMR) is a technique with the potential to be used in primary measurement procedures. This work presents the determination of purity by 1 H qNMR for nitrofuran metabolites 3-amino-2-oxazolidinone (AOZ), 3-amino-5-morpholinomethyl-2-oxazolidinone (AMOZ), and 1-aminohydantoin (AHD). Furthermore, a recent qNMR method developed by our group to improve the quantitative performance of measurements using 13 C nucleus was used to determine the purity of semicarbazide (SEM) nitrofuran metabolite. Purity values obtained by qNMR for AOZ, AMOZ, and AHD standards were compared to values obtained by the mass balance approach using a suite of analytical methods: Karl Fischer (KF) coulometric titration and thermogravimetry (TG) for the determination of water and residual solvents, gas and liquid chromatography for the determination of impurities structurally related to the metabolites. The results obtained by qNMR and mass balance were consistent.Graphical abstract.

Background: Brazil is one of the most biodiverse countries in the world, with about 37,000 species of land plants. Part of this biodiversity is within protected areas. The development of online databases in the last years greatly improved the available biodiversity data. However, the existing databases do not provide information about the protected areas in which individual plant species occur. The lack of such information is a crucial gap for conservation actions. This study aimed to show how the information captured from online databases, cleaned by a protocol and verified by taxonomists allowed us to obtain a comprehensive list of the vascular plant species from the "Parque Nacional do Itatiaia", the first national park founded in Brazil. All existing records in the online database JABOT (15,100 vouchers) were downloaded, resulting in 11,783 vouchers identified at the species level. Overall, we documented 2,316 species belonging to 176 families and 837 genera of vascular plants in the "Parque Nacional do Itatiaia". Considering the whole vascular flora, 2,238 species are native and 78 are non-native., New Information: The "Parque Nacional do Itatiaia" houses 13% of the angiosperm and 37% of the fern species known from the Brazilian Atlantic Forest. Amongst these species, 82 have been cited as threatened, following IUCN categories (CR, EN or VU), seven are data deficient (DD) and 15 have been classified as a conservation priority, because they are only known from a single specimen collected before 1969., (Marina M Moreira, Tatiana T Carrijo, Anderson Alves-Araújo, André M A Amorim, Alessandro Rapini, Andrews V S da Silva, Braz A P Cosenza, Claudia R Lopes, Camila N Delgado, Cíntia Kameyama, Dayvid R Couto, Daniel E F Barbosa, Daniele Monteiro, Diego R Gonzaga, Eduardo C Dalcin, Elsie F Guimarães, Elton John de Lírio, Fernando B Matos, Fátima R G Salimena, Felipe A Oliveira, Gustavo Heiden, João M Lanna, José Fernando Baumgratz, José F B Pastore, Juliana R P M Oliveira, Laísa B Barcelos, Lana S Sylvestre, Leandro Freitas, Leandro L Giacomin, Leandro Pederneiras, Leonardo D Meireles, Lúcia G Lohmann, Luciana C Pereira, Luis Alexandre E Silva, Luiz M Neto, Marcelo C Souza, Marcelo Trovó, Marcos E G Sobral, Mário Luís Garbin, Mario Gomes, Marli P Morim, Michelle Christine A Mota, Paulo H Labiak, Pedro L Viana, Pedro Luís R de Moraes, Renato Goldenberg, Rubens Luiz G Coelho, Samyra G Furtado, Sebastião José da Silva-Neto, Thiago B Flores, Valquíria F Dutra, Vinícius R Bueno, Rafaela C Forzza.)

Piperaceae species can be found worldwide in tropical and subtropical areas and many of them have been used for centuries in traditional folk medicine and in culinary. In Brazil, species of Piperaceae are commonly used in some communities as local anesthetic and analgesic. Countrified communities have known some species of the genus Ottonia as "anestesia" and it is a common habit of chewing leaves and roots of Ottonia species to relief toothache. The purpose of this study is to report our findings on new molecules entities obtained from the roots of Ottonia anisum Spreng, in which local anesthetic activity (sensory blockage) is demonstrated for the first time in vivo guinea pig model. Phytochemical investigation led to the isolation of three amides (pipercallosidine, piperine and valeramide) and in an enriched mixture of seven amides (valeramide, 4,5-dihydropiperlonguminine, N-isobutil-6-piperonil-2-hexenamide, piperovatine, dihydropipercallosidine, pipercallosidine and pipercallpsine). Our findings demonstrated the anesthetic potential for the methanolic extract from roots, its n-hexane partition and amides from O. anisum and it is in agreement with ethnobotanical survey.

Crude CH2Cl2 extract from leaves of Piper laevicarpu (Piperaceae) displayed antitrypanosomal activity against trypomastigote forms of Trypanosoma cruzi (Y strain) and antimicrobial potential against Cryptococcus gattii (strain-type WM 178). Bioactivity-guided fractionation of crude extract afforded one new natural bioactive lactam derivative, named laevicarpin. The structure of isolated compound, which displayed a very rare ring system, was elucidated based on NMR, IR and MS spectral analysis. Using MTT assay, the trypomastigotes of T. cruzi demonstrated susceptibility to laevicarpin displaying IC50 value of 14.7μg/mL (49.6μM), about 10-fold more potent than the standard drug benznidazole. The mammalian cytotoxicity of laevicarpin was verified against murine fibroblasts (NCTC cells) and demonstrated a CC50 value of 100.3μg/mL (337.7μM-SI=7). When tested against Cryptococcus gattii, laevicarpin showed an IC50 value of 2.3μg/mL (7.9μM) and a MIC value of 7.4μg/mL (25μM). Based in the obtained results, laevicarpin could be used as a scaffold for future drug design studies against the Chagas disease and anti-cryptococosis agents., (Copyright © 2016 Elsevier B.V. All rights reserved.)

Knowledge of the geographic distribution of plants is essential to underpin the understanding of global biodiversity patterns. Vascular epiphytes are important components of diversity and functionality of Neotropical forests but, unlike their terrestrial counterparts, they are under-represented in large-scale diversity and biogeographic analyses. This is the case for the Atlantic Forest - one of the most diverse and threatened biomes worldwide. We provide the first comprehensive species list of Atlantic Forest vascular epiphytes; their endemism patterns and threatened species occurrence have also been analyzed. A list with 2,256 species of (hemi-)epiphytes - distributed in 240 genera and 33 families - is presented based on the updated Brazilian Flora Checklist. This represents more than 15% of the total vascular plant richness in the Atlantic Forest. Moreover, 256 species are included on the Brazilian Red List. More than 93% of the overall richness is concentrated in ten families, with 73% represented by Orchidaceae and Bromeliaceae species alone. A total of 78% of epiphytic species are endemic to the Atlantic Forest, in contrast to overall vascular plant endemism in this biome estimated at 57%. Among the non-endemics, 13% of epiphytic species also occur either in the Amazon or in the Cerrado - the other two largest biomes of Brazil - and only 8% are found in two or more Brazilian biomes. This pattern of endemism, in addition to available dated phylogenies of some genera, indicate the dominance of recent radiations of epiphytic groups in the Atlantic Forest, showing that the majority of divergences dating from the Pliocene onwards are similar to those that were recently reported for other Neotropical plants.

Objectives: Fibromyalgia (FM) is a complex syndrome that is characterized by lasting and diffuse chronic musculoskeletal pain, derived from non-inflammatory causes and classically associated with the presence of specific tender points. However, studies have highlighted other important symptoms associated with a lower quality of life (QOL) in FM, such as sleep disturbances and alexithymia. This study aimed to investigate the pain, sleep and alexithymia patterns of FM patients treated in a Brazilian tertiary center., Methods: 20 patients with FM who were followed-up in the Rheumatology outpatient clinic of a Brazilian tertiary center (Faculdade de Medicina de São José do Rio Preto - FAMERP, São Paulo, Brazil) and 20 patients without FM from other outpatient services of the FAMERP completed a clinical and socio-demographic questionnaire, the Fibromyalgia Impact Questionnaire (FIQ), the Pittsburgh Sleep Quality Index (PSQI), the Toronto Alexithymia Scale (TAS-20) and the SF-36 (WHOQOL)., Results: The patients with FM presented worse performances in all QOL dimensions of the SF-36 and higher scores on the PSQI (p=0.01), and the TAS-20 (p=0.02). Patients with FM also scored significantly higher in all specific domains of PSQI and TAS-20., Discussion: The present data were in accordance with literature, disclosing a worse performance of patients with FM on pain impact, sleep complains and more presence of alexithymia., Conclusion: Studies have disclosed the presence of important and frequently underdiagnosed symptoms beyond pain complaints in FM, such as sleep complaints and alexithymia, and a better knowledge of such disturbances might improve FM patients' approach and treatment., (Copyright © 2014 Elsevier Editora Ltda. All rights reserved.)

Bioactivity-guided fractionation of the separate CH2Cl2 extracts from the aerial parts of Peperomia alata and P. trineura yielded seven polyketides: alatanone A [3-hydroxy-2-(5'-phenylpent-4'E-enoyl)cyclohex-2-en-1-one, 1a] and alatanone B [3-hydroxy-2-(3'-phenyl-6'-methylenedioxypropanoyl)cyclohex-2-en-1-one, 2a] from P. alata and trineurone A [3-hydroxy-2-(11'-phenylundec-10'E-enoyl)cyclohex-2-en-1-one, 1b], trineurone B [3-hydroxy-2-(15'-phenyl-18'-methylenedioxypentadecanoyl)cyclohex-2-en-1-one, 2b], trineurone C [3-hydroxy-2-(17'-phenyl-20'-methylenedioxyheptadecanoyl)cyclohex-2-en-1-one, 2c], trineurone D [3-hydroxy-2-(hexadec-10'Z-enoyl)cyclohex-2-en-1-one, 3a], and trineurone E [(6R)-(+)-3,6-dihydroxy-2-(hexadec-10'Z-enoyl)cyclohex-2-en-1-one, 3b] from P. trineura. The isolated compounds were evaluated for antifungal activity against Cladosporium cladosporioides and C. sphaeospermum and for cytotoxicity against the K562 and Nalm-6 leukemia cell lines.

The EtOAc extract from the leaves of Piper carniconnectivum C. DC. was subjected to chromatographic separation to afford two non-aromatic B-ring flavanone compounds: 5-hydroxy-2-(1'-hydroxy-4'-oxo-cyclohex-2'-en-1'-yl)-6,7-dimethoxy-2,3-dihydro-4H-chromen-4-one (1) and 5-hydroxy-2-(1',2'-dihydroxy-4'-oxo-cyclohexyl)-6,7-dimethoxy-2,3-dihydro-4H-chromen-4-one (2). The absolute configuration of (+)-1 was unambiguously determined as 2S,1'R by electronic circular dichroism (ECD) spectroscopy and comparison to simulated spectra that were calculated using time-dependent density functional theory (TDDFT). This methodology allowed the assignment of the absolute configuration of (+)-2 also as 2S,1'R, except for the stereogenic center at C-2', which was assigned as R because of the evidence drawn from high resolution NMR experiments. The cytotoxic activity of both compounds and 3 (hydrogenated B-ring derivative of 1) was evaluated on twelve human leukemia cell lines, and the IC50 values (<10 μM) indicated the activity of 1 against seven cell lines., (Copyright © 2013 Elsevier Ltd. All rights reserved.)

Background: Volatile oils from fresh roots, stems, leaves and seeds of Piper klotzschianum (Piperaceae) were obtained by hydrodistillation and analysed by GC-FID and GC-MS. In total, 25 components, representing more than 95% of the examined oils, were identified. The essential oils were evaluated against Artemia salina Leach nauplii and fourth-instar Aedes aegypti larvae., Results: The major chemical constituents that were identified from various parts of this plant were 1-butyl-3,4-methylenedioxybenzene and 2,4,5-trimethoxy-1-propenylbenzene in the root, 1-butyl-3,4-methylenedioxybenzene in the stems and leaves and 1-butyl-3,4-methylenedioxybenzene, limonene and α-phellandrene in the seeds. The biological activities of these essential oils generally exhibited high toxicity against A. salina, with LC50 values that ranged from 7.06 to 15.43 µg mL(-1), and significant larvicidal activity against fourth-instar A. aegypti larvae was observed in the essential oils from the seeds (LC50 of 13.27 µg mL(-1)) and roots (LC50 of 10.0 µg mL(-1)) of the plant., Conclusion: The present study indicates that both essential oil of P. klotzsdhianum and the isolate 1-butyl-3,4-methylenedioxybenzene are potential resources for A. aegypti larva control. This is the first report of the biological activities of the oil and isolated compound., (© 2013 Society of Chemical Industry.)

Piper aduncum L. is used in folk medicine to treat respiratory and inflammatory diseases. The aim of this study was to analyze the essential oil from leaves of P. aduncum collected in the Brazilian Cerrado, North of Minas Gerais, as well as to evaluate the larvicidal activity of this oil and of its major constituent. The essential oil was analyzed by gas chromatography coupled to flame ionization detector and gas chromatography coupled to mass spectrometry that allowed characterizing 23 compounds (monoterpenes: 90.4%; sesquiterpenes: 7.0%). The major component was 1,8-cineole (53.9%). This oil showed to be very different from those obtained from the same species. Larvae of A. aegypti were exposed to different concentrations of the essential oil and 1,8-cineole. The mortality rate of 100% was obtained after 24 h of treatment with the oil at concentrations of 500 and 1,000 ppm. After 48 h of treatment, the mortality rate was 80% and 50% for concentrations of 250 and 100 ppm, respectively. The LC₅₀ obtained after 24h was estimated in 289.9 ppm and after 48 h was 134.1 ppm. The major compound 1,8-cineole showed no larvicidal activity.

Leishmaniasis and Chagas disease are parasitic protozoan infections that affect the poorest population in the world, causing high mortality and morbidity. As a result of highly toxic and long-duration treatments, novel, safe and more efficacious drugs are essential. In this work, the methanol (MeOH) extract from the leaves of Piper malacophyllum (Piperaceae) was fractioned to afford one alkenylphenol, which was characterized as 4-[(3'E)-decenyl]phenol (gibbilimbol B) by spectroscopic methods. Anti-protozoan in vitro assays demonstrated for the first time that Leishmania (L.) infantum chagasi was susceptible to gibbilimbol B, with an in vitro EC(50) of 23 μg/mL against axenic promastigotes and an EC(50) of 22 μg/mL against intracellular amastigotes. Gibbilimbol B was also tested for anti-trypanosomal activity (Trypanosoma cruzi) and showed an EC(50) value of 17 μg/mL against trypomastigotes. To evaluate the cytotoxic parameters, this alkenylphenol was tested in vitro against NCTC cells, showing a CC(50) of 59 μg/mL and absent hemolytic activity at the highest concentration of 75 μg/mL. Using the fluorescent probe SYTOX Green suggested that the alkenylphenol disrupted the Leishmania plasma membrane upon initial incubation. Further drug design studies aiming at derivatives could be a promising tool for the development of new therapeutic agents for leishmaniasis and Chagas disease., (Copyright © 2012 Elsevier Inc. All rights reserved.)

The leaves and twigs of Piper krukoffii, collected in the Carajás National Forest, north Brazil, yielded essential oils (2.0% and 0.8%), the main constituents of which were myristicin (40.3% and 26.7%), apiole (25.4% and 34.1%) and elemicin (2.8% and 3.0%). The antioxidant activities of the oils, methanol extract and its sub-fractions were evaluated. The DPPH EC50 values varied from the ethyl acetate sub-fraction (73.4 +/- 3.7 microg/mL) to the methanol extract (24.9 +/- 0.8 microg/mL), and the ABTS TEAC values ranged in the same order from 265.7 to 349.2 microMol TE/g. These results indicated a significant antioxidant activity for the plant. The lignans (-)-kusunokin, yatein, (-)-hinokin and cubebin were identified in the methanol extract. The hydro-methanolic sub-fraction showed a high value for total phenol content (106.5 +/- 0.7 mg GAE/g), as well as 1H NMR signals for sugar moieties. Crude extracts and sub-fractions were also able to inhibit beta-carotene bleaching, varying from 22.4 to 47.1%. The oils from the leaves and twigs showed strong larvicidal (21.4 and 3.6 microg/mL) and fungicide (0.5 and 0.1 microg/mL) activities.

The Piperaceae species are known worldwide for its medicinal properties and its chemical compounds. In Brazil, many species of this family are distributed mainly in Amazon Region and in the Atlantic Forest. The genus Ottonia is known as source of amides, flavonoids, arilpropanoids and terpenes with record biological activities. Six aristolactams, including, aristolactam BII, piperolactam C, goniothalactam, stigmalactam, aristolactam AII and aristolactam BIII were isolated from roots of this species. GC-MS, 1H NMR and NOESY techniques were used to characterize these compounds. This is the first report about the occurrence of aristolactams in the Ottonia anisum Sprengel.

Analyses of essential oils obtained from fresh and dried leaves and inflorescences of Piper clausenianum were performed using GC-FID, GC-MS and NMR techniques. Forty compounds were detected for these four oils with the total of identified constituents ranging from 88.7% for the dried inflorescences to 97.7% for the dried leaves. Sesquiterpenes were the main constituents in the volatile fraction from leaves with a high percentage of (E)-nerolidol (up to 83%). However, monoterpenes were identified in greater amount in the inflorescences, with linalool percentages from 50% up. The essential oils from fresh leaves and inflorescences were submitted to anti-parasitic activity against a strain of Leishmania amazonensis. Both samples showed biological activity, but the essential oil from P. claussenianum fresh leaves, which was rich in (E)-nerolidol, showed effective growth inhibition of L. amazonensis due to the high percentage of this metabolite in the mixture.

The major components of the essential oil of Piper divaricatum from Marajó Island, PA, Brazil, were methyleugenol (63.8%) and eugenol (23.6%), which were identified by GC and GC-MS. Essential oils of Piper species from the Brazilian Amazon are rich in either mono- and sesquiterpenes or phenylpropanoids, as seen in this study. The oil was able to scavenging the DPPH radical, displaying an inhibition varying from 19% to 74%, with an EC50 value of 16.2 +/- 1.9 microg mL(-1). In the bleaching of beta-carotene, the inhibition of the oil oxidation was 60.0 +/- 2.7%. The oil gave minimum inhibitory concentrations for the fungi Cladosporium cladosporioides and C. sphareospermum of 0.5 microg and 5.0 microg, respectively. The oil also showed significant brine shrimp larvicidal activity (LC50, 38.8 +/- 0.8 microg mL(-1)).

The methanol extract from aerial parts of the Peperomia blanda (Piperaceae) yielded two C-glycosyl-flavones. Their structures were elucidated on the basis of extensive spectroscopic analysis, including 1D and 2D NMR, chemical transformation and comparison with the related known compounds. The structure of the new flavonoids were established as 4'-methoxy-vitexin 7-O-beta-D-xylopyranoside (1) (7-O-beta-D-xylopyranosyl-8-C-beta-D-glucopyranosyl-4'-methoxy-apigenin) and vicenin-2 (2). The antioxidant activity of both compounds was investigated using the DPPH assay. Both compounds showed only modest activity, with IC50 values of 357.2 microM for 1, and 90.5 microM for 2.

Five tetrahydrofuran lignans and two known flavones were isolated from the aerial parts of Peperomia blanda. The structures of the isolated lignans were elucidated by interpretation of their spectroscopic data, including by gHMQC and gHMBC. The relative and absolute configurations of the isolates were determined from NOESY interactions and optical properties, respectively. Four of the lignans were diastereomeric whilst one was of mixed biosynthetic origin. All but one of the lignans exhibited high in vitro trypanocidal activity when assayed against epimastigotes of Trypanosoma cruzi strain Y.

This paper contains data on the chemical composition of the essential oils of 22 leaf samples of Piper marginatum Jacq. collected in different areas and ecosystems of the brazilian Amazon, as well as an overview of the available literature. The species presents a large synonymy based on their different leaf characteristics and distinct scents where some of them smell like anise or very close compounds. By GC, GC/MS, and cluster analysis, we identified seven chemotypes for the leaf oils. The main components found in chemotype I were safrole (1) and 3,4-(methylenedioxy)propiophenone (2). The chemotype II was dominated by 3,4-(methylenedioxy)propiophenone (2) and p-mentha-1(7),8-diene (10). The major compounds identified in chemotype III were 3,4-(methylenedioxy)propiophenone (2), myristicin (3), (E)-beta-ocimene (11), and gamma-terpinene (12). In the chemotype IV, the principal constituents were beta-caryophyllene (13), alpha-copaene (14), and 3,4-(methylenedioxy)propiophenone (2). The chemotype V was dominated by (E)-isoosmorhizole (6), (E)-anethole (8), and isoosmorhizole (7). The main compounds found in the chemotype VI were 2-methoxy-4,5-(methylenedioxy)propiophenone (4), methoxy-4,5-(methylenedioxy)propiophenone isomer 5, and (E)-isoosmorhizole (6). The major constituents in chemotype VII were beta-caryophyllene (13), bicyclogermacrene (15), and (E)-asarone (9).

Chromatographic fractionation of a dichloromethane extract from the leaves of Piper scutifolium yielded two new isobutyl amides, scutifoliamide A ( 1) and scutifoliamide B ( 2), together with the known compounds piperolactam C ( 3), piperovatine ( 4), piperlonguminine ( 5), corcovadine ( 6), isopiperlonguminine ( 7), and isocorcovadine ( 8). From the dichloromethane extract from the leaves of P. hoffmannseggianum two new isobutyl amides, hoffmannseggiamide A ( 9) and hoffmannseggiamide B ( 10), were obtained together with the known compounds isopiperlonguminine ( 7) and isocorcovadine ( 8), sitosterol, and stigmasterol. The structures of the new compounds were established on the basis of spectroscopic data analysis. The inhibitory activity of compounds 1-10 against the growth of the fungi Cladosporium sphaerospermum and C. cladosporioides was determined by bioautography.

Piper crassinervium, P. aduncum, P. hostmannianum, and P. gaudichaudianum contain the new benzoic acid derivatives crassinervic acid (1), aduncumene (8), hostmaniane (18), and gaudichaudianic acid (20), respectively, as major secondary metabolites. Additionally, 19 known compounds such as benzoic acids, chromenes, and flavonoids were isolated and identified. The antifungal activity of these compounds was evaluated by bioautographic TLC assay against Cladosporium cladosporioides and C. sphaerospermum.

The volatile composition of ten Piperaceae species, comprising three genera (Ottonia, Piper and Peperomia) has been studied. The species were collected in a typical fragment of the Brazilian Atlantic forest, constantly being damaged by human action. The essential oils were obtained by hydrodistillation in a modified Clevenger-type apparatus and their analyses were performed by GC and GC/MS. Identification of the substances was made by comparison of mass spectra and retention indices with literature records. A great number of non-oxygenated monoterpenes and sesquiterpenes were identified. Most of these sesquiterpenes are derived from E,E-farnesyl-PP, suggesting a preference of these species to synthesize metabolites from this pathway. Arylpropanoids, although being common compounds produced by Piperaceae species, were not found in these oils.

The essential oil from Piper solmsianum leaves and its major compound (sarisan) were tested to verify their influences upon mice behaviour. The essential oil was obtained by hydrodistillation in a modified Clevenger extractor and analysed by GC/ MS. This analysis revealed in the oil the presence of monoterpenes, sesquiterpenes and of arylpropanoids. The compound sarisan, a myristicin analogue, was isolated from the oil to perform the pharmacological tests. Emulsions of the oil and of sarisan (5.0 and 10.0% v/v) were used in the tests. Pentobarbital (30 mg/ kg s.c.) or diazepam (2.5 mg/ kg s.c.) were tested as standard drugs to verify depressant or anxiolytic effects, respectively. Both essential oil and sarisan showed to have exciting and depressant effects in the tested animals.

The dichloromethane fraction obtained from the methanolic extract of leaves of P. lhotzkyanum afforded a C-glucosylflavone (kaplanin) together with sakuranetin, methyl 4-methoxydihydroferulate and a mixture of methyl ferulate and dihydroferulate derivatives. Spectrometric methods were used to elucidate the structures of these compounds.