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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.

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Piper aduncum L., a Brazilian medicinal plant, is known for its bioactive properties, including repellent and insecticidal effects. This study investigated the insecticidal potential of essential oils (EOs) from P. aduncum, collected during the dry and rainy seasons, against fleas (Ctenocephalides felis felis Bouché, 1835) in egg and adult stages. The EOs were obtained by hydrodistillation using a modified Clevenger apparatus for 2 h. Qualitative and quantitative analysis were performed via gas chromatography. The findings revealed that dillapiole was the predominant substance in both EOs, accounting for 77.6% (rainy) and 85.5% (dry) of the EOs. These EOs exhibited high efficacy against the parasite C. felis felis, resulting in 100% egg mortality at a concentration of 100 µg/mL and 100% mortality for adult fleas starting from 1,000 µg/mL. Dillapiole standard was also effective but at a relatively high concentration. This finding suggested that EOs from P. aduncum exhibit cytotoxicity against these pests and might hold potential for commercial production, offering practical applications for such bioprospecting. This study uniquely revealed that the EOs from P. aduncum, which is rich in dillapiole, demonstrated pulicidal activity against the parasite C. felis felis, particularly in inhibiting the hatching of the eggs of these parasites.

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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.

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The Palmares Environmental Protection Area covers almost 90% of Paty do Alferes Atlantic Forest with great biodiversity. This work aimed to research about the knowledge local specialists have about medicinal plants in order to describe the relationship between home gardens and the conservation of biodiversity and local knowledge. 107 ethnospecies were reported belonging to 37 botanical families, Asteraceae the most abundant and a majority of native species. The highest RCF species were Plectranthus barbatus and the highest RI was obtained for Plantago australis/P. guilleminiana. Plants were cited mainly for the treatment of illness related to digestive system and the highest FIC was about the use of plants related to eye diseases. Local experts mainly cited plants for low complexity health problems. Home gardens, as the main collection site, contribute to minimizing anthropic pressure and extractivism, which favours a sustainable relationship within the APA, at least regarding to medicinal plants.

El Área de Protección Ambiental de Palmares cubre casi el 90% de la Mata Atlántica de Paty do Alferes con una gran biodiversidad. Este trabajo tuvo como objetivo investigar el conocimiento que los especialistas locales tienen sobre las plantas medicinales con el fin de describir la relación entre los huertos familiares y la conservación de la biodiversidad y el conocimiento local. Se reportaron 107 etnoespecies pertenecientes a 37 familias botánicas, Asteraceae la más abundante y la mayoría de las especies nativas. Las especies de RCF más altas fueron Plectranthus barbatus y la IR más alta se obtuvo para Plantago australis/P. guilleminiana. Las plantas se citaron principalmente para el tratamiento de enfermedades relacionadas con el sistema digestivo y el FIC más alto fue sobre el uso de plantas relacionadas con enfermedades oculares. Los expertos locales citaron principalmente las plantas por problemas de salud de baja complejidad. Los huertos familiares, como principal sitio de acopio, contribuyen a minimizar la presión antrópica y el extractivismo, lo que favorece una relación sustentable dentro de la APA, al menos en lo que respecta a las plantas medicinales.

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Introduction: Cannabis sativa L. medicinal oils are good therapeutic options due to their wide spectrum of pharmacological applications and the easy adjustment of individual doses. The lack of standardization of methodology in the preparation of medicinal oil using the Cannabis crude extract results in elevated variability of cannabinoid concentration in the final product. The elevated variability impairs the understanding of beneficial and adverse effects related to dose-response pharmacological activities. Objective: This study aimed to conduct a review on the current methods of Cannabis oil preparation present in the literature, to demonstrate the most appropriate methodologies to ensure a product with high content of cannabinoids and terpenes. Results: The decarboxylation stage is essential for the conversion of acid cannabinoids into neutral cannabinoids, which are substances with the highest bioavailability. Lower temperatures for longer periods of time instead of high temperatures in less time are highly recommended to ensure that all the acidic cannabinoids have passed through decarboxylation. For the guarantee of a high terpene content, the separate addition of essential oil to the fixed oil prepared from the crude extract should be considered. Ultrasound-assisted extraction is one of the best performing methodologies because it is cheaper than other techniques, such as supercritical fluid extraction, besides that, ultrasound extraction is effective in short extraction times and uses small amounts of solvent when compared with other techniques. Conclusion: Although the literature about the methods of preparation of Cannabis medicinal oil is scarce, it is possible to standardize an optimized, low-cost, and effective Cannabis extractive methodology from the results found in the literature; however, this will depend on new research for methodological validation.

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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.

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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.

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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, (-)-ß-pinene and limonene. EOs showed an IC50 lower than all isolated compounds, except for (-)-ß-pinene in OSCC cells. The (-)-ß-pinene induced cell death with apoptotic characteristics. Commercial standards showed greater selectivity than EOs, and (-)-ß-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.

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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' (SRO), to enable a value for mixtures of metabolites to be generated, the 'general mixture redox index' (GMOR). 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 SRO and GMRO 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.

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Current treatment guidelines for leishmaniasis is based on chemotherapy with drugs that show a set of limitations such as high cost, toxicity, difficult route of administration, and lack of efficacy in endemic areas. In this context, phytopharmaceutical products and herbal medicines emerge as promising alternatives for developing new treatment against leishmaniasis. This review discusses the perspectives of leishmaniasis treatment based on natural products and phytotherapy highlighting the Piper genus, especially P. aduncun and P. mollicomum Kunth covering the period of 1998 to 2020. Leishmanicidal activity of pure compounds of Piper spp. [3-(3,4,5-trimethoxyphenyl) propanoic acid, 3-chlorosintenpyridone, 2'-hydroxy-3',4',6'-trimethoxy-chalcone, cardamonin, conocarpan, cubebin, eupomatenoid, flavokavain B, ( +)-(7R,8S)-epoxy-5,6-didehydrokavain, N-[7-(3',4'-methylenedioxypheny l-2(E),4(E)-heptadienoyl-pyrrolidine, N-[7-(3',4'-methylenedioxyphenyl)-2(Z),4(Z)-heptadienoyl-pyrrolidine, piperovatine, pellitorine, and piplartine (piperlongumine)] were proved against the promastigote and amastigote forms of parasite related with cutaneous (L. (L.) amazonensis, L. (V.) braziliensis, and L. (V.) guyanensis) and visceral (L. (L.) donovani, L. (L.) chagasi, and L. (L.) infantum). We also discussed the perspective of leishmaniasis treatment, considering the potential synergism between different promising species of Piper, presenting some interesting interaction possibilities for future studies between plants. Finally, the necessary steps for technological development of phytomedicines and herbal medicines with the desirable quality requirements for medicines are highlighted. The data presented here highlight the use of Piper spp. as source of pharmacological compounds that can lead to effective, safe, and inexpensive treatments for leishmaniasis.

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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 ß-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.

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Arrabidaea chica Verlot (crajiru) is a plant used in folk medicine as an astringent, anti-inflammatory, wound healing and to treat fungal and viral diseases such as measles chickenpox and herpes. Arrabidaea chica has several morphotypes recognized but little is known about its chemical variability. In the present study the anthocyanidin profile of A. chica morphotypes collected in two seasons (summer and winter) have been examined and their activity against Leishmania infection compared. High-performance liquid chromatography coupled to a diode-array detector (HPLC-DAD-UV) and by tandem mass spectrometry with electrospray ionization (ESI-MS/MS) were used for anthocyanidin separation and identification. Antileishmanial activity was measured against promastigote forms of Leishmania amazonensis. Multivariate analysis, principal component analysis (PCA) and Pearson's correlation were performed to classify morphotypes accordingly to their anthocyanidin profile. The presence of 6,7,3',4'-tetrahydroxy-5-methoxyflavylium (3'-hydroxy-carajurone) (1), carajurone (2), 6,7,3'-trihydroxy-5,4'-dimethoxy-flavylium (3'-hydroxy-carajurin) (3) and carajurin (4), and three unidentified anthocyanidins were detected. Two different groups were recognized: group I containing 3'-hydroxy-carajurone; and group II with high content of carajurin. Among anthocyanidins identified in the extracts, only carajurin showed significant statistical correlation (p = 0.030) with activity against L. amazonensis. Carajurin could thus be considered as a pharmacological marker for the antileishmanial potential of the species.

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