RESUMO
This work covers a systematic review of literature about the genus Cecropia from 1978 to 2020, emphasizing the analysis of 10 of the most relevant species and their associated biological activities. Cecropia is a neotropical genus, which comprises about 61 native species in the American continent where it is known to be part of the traditional medicine of numerous countries. Secondary metabolites described for this genus showed an elevated structural and functional diversity, where polyphenols have been the most abundant. Based on this diversity, Cecropia phytochemicals represent an important source of potential therapeutic agents yet to be exploited. This review also highlights the effectiveness of combining chemometrics and ultra-performance liquid chromatography-tandem mass spectrometry as a novel approach to successfully single out Cecropia species phytochemicals. While the medicinal use of Cecropia species is officially recognized in National Pharmacopoeias and Formularies of several Latin American countries, it is important to recognize that these phytomedicines are complex mixtures requiring a thorough understanding of their chemical composition and their correlation with biological activities to guarantee their quality, safety, and efficacy.
Assuntos
Cecropia , Extratos Vegetais , Medicina Tradicional , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , PolifenóisRESUMO
Context: Since there is still a great need to search for plant species with antinociceptive and anti-inflammatory activities, Diploptropis purpurea (Rich.) Amshoff (Fabaceae) is studied for the first time. Objective: This evaluates the analgesic and anti-inflammatory activities of the stem methanol extract of Diplotropis purpurea (MEDP). Material and methods: The anti-inflammatory and analgesic effects of MEDP of D. purpurea were evaluated in vivo. The antinociceptive activity was assessed in CD1 male mice were treated by oral gavage with 500 mg/kg of MEDP 30 min before submitting to acetic acid-induced abdominal writhing, hot-plate, and formalin tests. Paws oedema induced by carrageenan, histamine or serotonin were performed in male Sprague-Dawley rats to determinate the anti-inflammatory activity. Results: Oral administration of MEDP produced significant antinociceptive effects on the inflammatory phase in the formalin test [12.0 s versus 72.5 s in carboxymethyl cellulose (CMC) control group]. MEDP produced an analgesic effect in the hot-plate model, although the effect was modest compared to tramadol (40 and 60%, respectively). The oral administration of MEDP in a dose of 500 mg/kg showed maximum inhibition (75.1%) after 0.5 h in carrageenan-induced oedema, but it did not modify histamine or serotonin-induced oedemas. Discussion and conclusion: In the peripheral nociception model, acetic acid-induced abdominal writhing, the MEDP did not show a protective effect, but its analgesic effects were evident in the inflammatory phase of the formalin test and in the hot-plate model. These results show that the anti-inflammatory effect was accompanied by a reduction in the perception of painful stimuli.
Assuntos
Analgésicos/farmacologia , Anti-Inflamatórios/farmacologia , Edema/tratamento farmacológico , Fabaceae/química , Dor/tratamento farmacológico , Extratos Vegetais/farmacologia , Animais , Edema/induzido quimicamente , Inflamação/tratamento farmacológico , Masculino , Metanol/química , Camundongos , Dor/induzido quimicamente , Medição da Dor , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Ratos , Ratos Sprague-DawleyRESUMO
ETHNOPHARMACOLOGICAL RELEVANCE: Piperaceae is the fifth largest family of plants in Panama. This review focuses on the ethnomedical uses of the most prevalent Panamanian species and biological activities of their extracts and/or constituents both in Panama and worldwide. Many species have a plethora of ethnomedical uses such as antibacterial, antifungal, anti-inflammatory, anticancer, antidiabetic, anti-Helicobacter pylori, antiulcer, antiprotozoal, estrogenic, insecticidal, local anesthetic, diuretic, and for women's health conditions. AIM OF THE REVIEW: The aim of this review is to compile all ethnomedical uses of most prevalent species of Piper in Panama, and their extracts or phytoconstituents worldwide, through a complete literature search, so that it may allow selection of potential unexplored Piper species for future research and development of phytotherapeuticals for important ailments. METHODOLOGY: This review conducted a thorough search in books and databases such as Google Scholar, PubMed, Sci-Finder, Scopus, ACS publications, Science Direct, and Reaxys (Elsevier), until October of 2017. The information provided in this review is based on peer-reviewed papers only in English. The key words used to search were: "Piper", "Piperaceae", "Panama", "Pharmacological activity", "Chemistry," "Toxicity," and "Clinical studies". Scientific names of the plants were validated through www.tropicos.org. Potential full-texts of eligible papers, irrespective of database, were identified. Study selection and data extraction were conducted by one author (AIS) and confirmed by others (MPG, ADA). The extracted data were summarized in tabular form and a narrative description was used to provide a summary of updated information. RESULTS: The ethnomedical uses of most prevalent 23 Panamanian species of Piper both in Panama as well in the world are provided. Of these species only Piper arboreum, Piper auritum, Piper cordulatum, Piper hispidum, Piper dariense, Piper multiplinervium and Piper umbellatum have ethnomedical uses in Panama. Some of the uses are by native Amerindians of Panama. These include ailments such as liver pains, common colds, skin infections, insecticidal, as a bath to alleviate colds, snakebites, different types of pains, skin ailments, wound healing, rheumatism, women's health, antipyretic, and anti-inflammatory. Other Panamanian species are widely used in many countries of the world. Of all the Piper species, P. aduncum has the most ethnomedical uses. Panamanian uses are different from the ones in other countries. A total of 61 compounds present in Piper species reported in this review have shown a variety of biological activities in vitro. These compounds belong to different chemical types, such as chromenes, amides, alkaloids, benzopyrans, benzoates, essential oils, pyrrolidines, flavokaines, chalcones, methylenedioxy propiophenones, cinnamates, monoterpenes, sesquiterpenes, phenols, among others. From this review it is evident that extracts and pure compounds isolated from Piper species have shown a wide array of mainly in vitro activity and some ethnomedical uses may be correlated with their activities reported. CONCLUSIONS: Plants of this genus have provided bioactive species, both from crude extracts and pure compounds thus substantiating their efficacy in traditional medicine. In vivo and toxicological studies are still limited, but the results of different activities of Piper reported point out the great potential of these species for obtaining bioactive principles that may be useful in treating diseases. However, a thorough investigation of Piper species relating to chemistry, in vivo pharmacological activities, with emphasis on their mechanism of action, safety and efficacy and toxicity is warranted.
Assuntos
Etnofarmacologia , Medicina Tradicional , Piper/química , Extratos Vegetais/uso terapêutico , Animais , Características Culturais , Conhecimentos, Atitudes e Prática em Saúde/etnologia , Humanos , Indígenas Centro-Americanos/psicologia , Panamá , Fitoterapia , Piper/efeitos adversos , Piper/classificação , Extratos Vegetais/efeitos adversos , Extratos Vegetais/isolamento & purificação , Plantas MedicinaisRESUMO
In this work, we discuss the characterization and diversity analysis of 354 natural products (NPs) from Panama, systematically analyzed for the first time. The in-house database was compared to NPs from Brazil, compounds from Traditional Chinese Medicine, natural and semisynthetic collections used in high-throughput screening, and compounds from ChEMBL. An analysis of the "global diversity" was conducted using molecular properties of pharmaceutical interest, three molecular fingerprints of different design, molecular scaffolds, and molecular complexity. The global diversity was visualized using consensus diversity plots that revealed that the secondary metabolites in the Panamanian flora have a large scaffold diversity as compared to other composite databases and also have several unique scaffolds. The large scaffold diversity is in agreement with the broad range of biological activities that this collection of NPs from Panama has shown. This study also provided further quantitative evidence of the large structural complexity of NPs. The results obtained in this study support that NPs from Panama are promising candidates to identify selective molecules and are suitable sources of compounds for virtual screening campaigns.
Assuntos
Produtos Biológicos/química , Descoberta de Drogas , Informática , Biodiversidade , Panamá , Plantas/química , Plantas/classificaçãoRESUMO
The chemical composition of leaf essential oils from 11 species of Piper from Panama was analyzed by a combination GC-FID and GC-MS procedures. Six of them had sesquiterpene hydrocarbons as major constituents, three were characterized by monoterpene hydrocarbons, one by a diterpene, and one by a phenylpropanoid, dillapiole. The main components identified in each species were: cembratrienol (25.4â%) in Piper augustum; ß-pinene (26.6â%) in Piper corrugatum; α-pinene (19.4â%) in Piper curtispicum; trans-ß-farnesene (63.7â%) in Piper darienense; p-cymene (43.9â%) in Piper grande; dillapiole (57.7â%) in Piper hispidum; linalool (14.5â%), α-phellandrene (13.8â%), and limonene (12.2â%) in Piper jacquemontianum; ß-caryophyllene (45.2â%) in Piper longispicum; linalool (16.5â%), α-phellandrene (11.8â%), limonene (11.4â%), and p-cymene (9.0â%) in Piper multiplinervium; ß-selinene (19.0â%), ß-elemene (16.1â%), and α-selinene (15.5â%) in Piper reticulatum; and germacrene D (19.7â%) in Piper trigonum. The essential oils of P. hispidum and P. longispicum at a concentration of 250 µg/mL showed larvicidal activity against Aedes aegypti, while the oils from P. curtispicum, P. multiplinervium, P. reticulatum, and P. trigonum were inactive (LC100 ≥ 500 µg/mL). The essential oils of P. grande, P. jacquemontianum, and P. multiplinervium showed no significant antifungal activity (MIC > 250 µg/mL) against several yeasts and filamentous fungal strains.
Assuntos
Óleos Voláteis/química , Piper/química , Óleos de Plantas/química , Aedes/efeitos dos fármacos , Animais , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Inseticidas/química , Inseticidas/isolamento & purificação , Larva/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Óleos Voláteis/farmacologia , Panamá , Óleos de Plantas/farmacologiaRESUMO
A dichloromethane extract of the roots from the Panamanian plant Swartzia simplex exhibited a strong antifungal activity in a bioautography assay against a genetically modified hypersusceptible strain of Candida albicans. At-line HPLC activity based profiling of the crude extract enabled a precise localization of the antifungal compounds, and dereplication by UHPLC-HRESIMS indicated the presence of potentially new metabolites. Transposition of the HPLC reversed-phase analytical conditions to medium-pressure liquid chromatography (MPLC) allowed an efficient isolation of the major constituents. Minor compounds of interest were isolated from the MPLC fractions using semipreparative HPLC. Using this strategy, 14 diterpenes (1-14) were isolated, with seven (5-10, 14) being new antifungal natural products. The new structures were elucidated using NMR spectroscopy and HRESIMS analysis. The absolute configurations of some of the compounds were elucidated by electronic circular dichroism spectroscopy. The antifungal properties of these compounds were evaluated as their minimum inhibitory concentrations in a dilution assay against both hypersusceptible and wild-type strains of C. albicans and by assessment of their antibiofilm activities. The potential cytological effects on the ultrastructure of C. albicans of the antifungal compounds isolated were evaluated on thin sections by transmission electron microscopy.
Assuntos
Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Produtos Biológicos/isolamento & purificação , Produtos Biológicos/farmacologia , Candida albicans/efeitos dos fármacos , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Fabaceae/química , Antifúngicos/química , Produtos Biológicos/química , Cromatografia Líquida de Alta Pressão , Diterpenos/química , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Panamá , Casca de Planta/químicaRESUMO
BACKGROUND: Plinia cerrocampanensis is an endemic plant of Panama. The leaf essential oil of this plant has shown antibacterial activity. However, anti-malarial activity and chemical profiling by HS-SPME-GC-MS of this essential oil have not been reported before. METHODS: Anti-malarial activity of the essential oil (EO) was evaluated in vitro against chloroquine-sensitive HB3 and chloroquine-resistant W2 strains of Plasmodium falciparum. Synergistic effect of chloroquine and the EO on parasite growth was evaluated by calculating the combination index. A methodology involving headspace solid phase microextraction and gas chromatography-mass spectrometry (HS-SPME-GC-MS) was developed to investigate the composition of Plinia cerrocampanensis EO. RESULTS: Plinia cerrocampanensis EO showed a high anti-malarial activity and a synergistic interaction with chloroquine. The Plinia cerrocampanensis EO inhibited P. falciparum growth in vitro at an IC50 of 7.3 µg/mL. Chloroquine together with the EO decreased the IC50 of chloroquine from 0.1 µg/mL to 0.05 µg/mL, and of the EO from 7.3 µg/mL to 1.1 µg/mL. The measured combination index was 0.58, which clearly indicates that the EO acts synergistically with chloroquine. Since the EO maintained its inhibitory activity on the chloroquine-sensitive strain of the parasite, it could be acting by a different mechanism of action than chloroquine. The best HS-SPME-GC-MS analytical conditions were obtained when the temperature of extraction was 49°C, incubation time 14 min, and the time of extraction 10 min. This method allowed for the identification of 53 volatile constituents in the EO, including new compounds not reported earlier. CONCLUSIONS: The anti-malarial activity exhibited by the Plinia cerrocampanensis EO may lend support for its possible use as an alternative for anti-malarial therapy.
Assuntos
Antimaláricos/farmacologia , Cloroquina/farmacologia , Cromatografia Gasosa-Espectrometria de Massas/métodos , Myrtaceae/química , Óleos Voláteis/farmacologia , Folhas de Planta/química , Plasmodium falciparum/efeitos dos fármacos , Microextração em Fase Sólida/métodos , Antimaláricos/análise , Cloroquina/análise , Óleos Voláteis/química , PanamáRESUMO
From the methanol root extract of Godmania aesculifolia, a species selected in a multinational OAS program aimed at discovering antifungal compounds from Latin American plants, a new chavicol diglycoside (1), the known 3,4-dihydroxy-2-(3-methylbut-2-en-1-yl)-3,4-dihydronaphthalen-1(2H)-one (2), and lapachol (3) were isolated and characterized by 1D and 2D NMR and MS techniques. Only 3 exhibited fairly good activity against a panel of clinical isolates of Cryptococcus neoformans (MIC50 between 7.8 and 31.2 µg/mL) and moderate activities against Candida spp. and non-albicans Candida spp.
Assuntos
Anisóis/isolamento & purificação , Antifúngicos/isolamento & purificação , Bignoniaceae/química , Glicosídeos/isolamento & purificação , Naftoquinonas/isolamento & purificação , Derivados de Alilbenzenos , Anisóis/química , Anisóis/farmacologia , Antifúngicos/química , Antifúngicos/farmacologia , Aspergillus/efeitos dos fármacos , Candida/efeitos dos fármacos , Cryptococcus neoformans/efeitos dos fármacos , Glicosídeos/química , Glicosídeos/farmacologia , Humanos , Testes de Sensibilidade Microbiana , Microsporum/efeitos dos fármacos , Estrutura Molecular , Naftoquinonas/química , Naftoquinonas/farmacologia , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Raízes de Plantas/química , Trichophyton/efeitos dos fármacosRESUMO
Acetylcholinesterase (AChE) inhibitors have been used for the symptomatic treatment of Alzheimer's disease. Eleven whole plants from Panama belonging to the Lycopodiaceae family have been screened for their anticholinesterase inhibitory and antioxidant activities by a thin-layer chromatography (TLC) bioautography method. Of these, only Lycopodium clavatum subsp. clavatum showed strong AChE inhibition. Seven plant extracts showed moderate inhibition, two of them, Huperzia cf chamaeleon and Huperzia reflexa, also possessed an antioxidant activity. This is the first report of anticholinesterase and antioxidant activities in these two native plants. Additionally, alkaloid extracts of the Lycopodiaceae plants were also analysed by TLC and LC-MS to identify the well-known AchE inhibitor, huperzine A. Two plants, H. cf chamaeleon and H. reflexa var. minor, showed the presence of huperzine.
Assuntos
Inibidores da Colinesterase/química , Lycopodiaceae/química , Alcaloides/química , Antioxidantes/química , Cromatografia em Camada Fina , Lycopodium/química , Espectrometria de Massas , Panamá , Extratos Vegetais/química , Sesquiterpenos/químicaRESUMO
Diverse α-naphthylamine derivatives were easily prepared from corresponding aldimines derived from commercially available α-naphthaldehyde and anilines or isomeric pyridinecarboxyaldehydes and α-naphthylamine. The secondary amines obtained were tested as possible antifungal and cytotoxic agents. The diverse N-aryl-N-[1-(1-naphthyl)but-3-enyl]amines obtained were active (IC(50) < 10 µg/mL) against breast (MCF-7), non-small cell lung (H-460), and central nervous system (SF-268) human cancer cell lines, while N-(pyridinylmethyl)-naphthalen-1-amines resulted in activity against (MIC 25-32 µg/mL) some human opportunistic pathogenic fungi including yeasts, hialohyphomycetes, and dermatophytes.