The
species are a recognized botanical source of a broad structural diversity of lignans and its derivatives. For the first time,
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
of 9.8 ± 1.22 μM and around 80% relaxation at 30 μM. These results suggest that
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.
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•Mono and sesquiterpenes are the main components of Piperaceae essential oils.•Chemotaxonomy of the family is influenced by the compound chosen.•P. cernuum is characterized by ...agarofuran sesquiterpenes.•E. coli inhibition is associated to bicyclogermacrene and γ-muurolene.•Staphylococci inhibition is associated to limonene and cis-β-ocimene.
Piper is a large and highly diverse genus of plants with medicinal and aromatic use. It is widely distributed in tropical forests occupying distinct environments. We have determined the chemical composition of the essential oils from 11 species of Piper from seven locations of Atlantic rainforest in Brazil. The essential oils were isolated by hydrodistillation and their composition, determined by GC–MS. The chemical composition of the oils exhibits qualitative and quantitative differences among the species and intraspecifically for distinct locations. Mono and sesquiterpenes were the most abundant compounds, although P. aduncum also contained phenylpropanoids. The oils of P. xylosteoides, P. umbellatum and P. leptorum from coastal and inland regions consisted exclusively of oxygenated sesquiterpenes. In contrast, monoterpene was the sole chemical class in the oils extracted from P. rivinoides and P. solmsianum. Hierarchical clustering analyses demonstrated the chemical phenotype is associated to species-specific and environmental factors. The essential oils from the majority of the investigated Piper species exhibit inhibitory activity against pathogenic bacteria in vitro, reaching up to 30% of the inhibition levels of commercial antibiotics. The contents of bicyclogermacre and γ-muurolene were positively associated to E. coli inhibition, whereas, levels of germacrene D and trans-caryophyllene were associated to the inhibitory activity against all tested bacteria. Limonene and cis-β-ocymene were associated with Staphylococci inhibition. Higher contents of β‐phellandrene were positively correlated to wide spectrum antibacterial activity. Taken together, our results demonstrate the chemical diversity of Piper essential oils and their potential as novel antibacterial agents for several industrial applications.
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.
•Our group is promoting the inventory of the aromatic plants of the Brazilian Amazon.•The essential oils of Piper species are highlighted with regard to their possible economic uses.•The biological ...active compounds from Piper oils could be used on new drugs of the pharmaceutical industry.•New agricultural prospects can help the Brazilian society in the mitigation of deforestation of the Amazon region.
The hydrodistilled oils of Piper hispidum, Piper aleyreanum, and Piper anonifolium, collected in the Carajás National Forest, Pará state, Brazil, were analyzed by GC and GC–MS and then, evaluated their antioxidant, antifungal, anticholinesterase and cytotoxic activities. In total, 87 constituents were identified in the Piper oils. The sesquiterpenes were the most highly represented classes and the main compounds found in the Piper oils were selin-11-en-4-α-ol, β-elemene, β-selinene, α-selinene, bicyclogermacrene, β-caryophyllene, α-humulene, and δ-elemene. All analyzed oils showed powerful antifungal activity, with the detection limit (DL) from 0.1 to 1.0μg against the Cladosporium cladosporioides and Cladosporium sphareospermum fungi, as well they have no lytic effect against the mice erythrocytes. In the anticholinesterase evaluation, the oils of P. anonifolium (DL=0.01ng) and P. hispidum (DL=0.01ng) were hundred times more potent than the standard physostigmine (DL=1.0ng). Moreover, the oil of P. aleyreanum showed high in vitro cytotoxic activity against the human melanoma cell line SKMEL-19 (IC50=7.4μg/mL) and significant antioxidant activity (DPPH=412.2mg TE/mL). The higher cell growth inhibition induced by the oil of P. aleyreanum is probably due to elemene (β-, δ-, and γ-elemene), as well as other structurally related compounds, which were previously reported in the proliferation inhibition, stimulation of apoptosis and induction of cell cycle arrest in malignant cells.
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.
Volatiles released by damaged plants are used as cues by predators and parasitoids to find their herbivorous prey. Here, we assessed whether odor cues released by simulated herbivore-damaged leaves ...in
Piper mollicomum
attract predaceous wasps. We applied plasticine dummy caterpillars as an herbivore model to evaluate predation risk on undamaged and artificially damaged leaves by the mandible marks left by foraging wasps. Despite observing a tendency of a visual component in the wasp attraction (more marks on dummies under old naturally damaged leaves), we observed that chemical cues play a crucial role, with recent artificial damage and leaves baited with volatile essential oils of
P. mollicomum
attracting more wasps for the dummies than those untreated. Headspace analysis by GC–MS showed that undamaged leaves released small amounts of compounds, while damaged ones released 63 times more volatiles, which consisted of a blend containing mostly mono- and sesquiterpenoids. Histochemical tests revealed that terpenoids are located in oil cells spread among the leaf tissue, and may be released by the disruption of such cells when herbivores are feeding on leaves. We suggest that signals of disrupted plants differ from the mosaic of odor blends emitted by the background environment and may provide a detectable, although not necessarily specific, cue for prey presence. Such detectable cues are important for generalist foraging predaceous wasps, since they spend time searching for prey in different host plants.
Twelve samples of air-dried aerial parts of Piper dilatatum L. C. Rich yielded essential oils and their volatile constituents were analyzed by GC and GC–MS. Sesquiterpenes, both hydrocarbons and ...oxygenated, were the most highly represented classes, the former ranging from 31.5% to 87.7% and the latter varying from 1.8% to 49.4%. Using hierarchical cluster analysis, the oils were divided into seven groups, whose main constituents were: (E)-caryophyllene, α-cadinol and germacrene D (group A); spathulenol, bicyclogermacrene and (Z)-β-ocimene, (group B); spathulenol, germacrene D and (E)-nerolidol, (group C); germacrene D, limonene, α-phellandrene and bicyclogermacrene (group D); β-elemene, germacrene D and β-pinene (group E); curzerene, p-cymene and α-eudesmol (group F); and (Z)-α-bisabolene, curzerene and germacrene D (group G). We have seen that Piper oils from the Amazon present as major constituents terpenoids and phenylpropanoids, always with the predominance of one over another. The essential oils of P. dilatatum presented in this paper, containing only mono- and sesquiterpenes as its major components, is further chemotaxonomic evidence of this dichotomy in the Piper genus.
► The essential oils of twelve specimens of Piper dilatatum occurring in the Amazon were analyzed. ► The oils were grouped into seven groups based on hierarchical analysis. ► The sesquiterpenes hydrocarbons and oxygenated sesquiterpenes predominate in these oils, with very different structural types. ► This is a chemotaxonomic contribution to better understanding of Piper species.
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.
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► Alkenylphenol gibbilimbol B was isolated from Piper malacophyllum. ► Gibbilimbol B was evaluated in vitro against Leishmania spp. and Trypanosoma cruzi. ► L. (L.) infantum chagasi ...and T. trypomastigotes were susceptible to gibbilimbol B. ► The alkenylphenol suggested the disruption of the Leishmania plasma membrane at initial incubation time.
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)-decenylphenol (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 EC50 of 23μg/mL against axenic promastigotes and an EC50 of 22μg/mL against intracellular amastigotes. Gibbilimbol B was also tested for anti-trypanosomal activity (Trypanosoma cruzi) and showed an EC50 value of 17μg/mL against trypomastigotes. To evaluate the cytotoxic parameters, this alkenylphenol was tested in vitro against NCTC cells, showing a CC50 of 59μg/mL and absent hemolytic activity at the highest concentration of 75μg/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.
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