Unusual chromenes from Peperomia blanda. Phytochemistry 2006, 67, 492–496. © 2015 by the authors; licensee MDPI

Abstract From the methanol extract of the aerial parts of Peperomia blanda (Piperaceae), two chromenes were isolated and characterized mainly through application of 2D-NMR spectroscopy. The structures were 2S-(4-methyl-3-pentenyl)-6-formyl-8-hydroxy-2,7-dimethyl-2H-chromene and 2S-(4-methyl-3-pentenyl)-5-hydroxy-6-formyl-2,7-dimethyl-2H-chromene named as blandachromenes I and II, respectively

Larvicidal activity of Ottonia anisum metabolites against Aedes aegypti: A potential natural alternative source for mosquito vector control in Brazil

Submitted by Sandra Infurna ([email protected]) on 2017-04-25T15:17:22Z No. of bitstreams: 1 nildimar_honorio_etal_IOC_2017.pdf: 285283 bytes, checksum: 258d00de4d51d5f0c1878a247188f7b5 (MD5)Approved for entry into archive by Sandra Infurna ([email protected]) on 2017-04-25T15:43:34Z (GMT) No. of bitstreams: 1 nildimar_honorio_etal_IOC_2017.pdf: 285283 bytes, checksum: 258d00de4d51d5f0c1878a247188f7b5 (MD5)Made available in DSpace on 2017-04-25T15:43:34Z (GMT). No. of bitstreams: 1 nildimar_honorio_etal_IOC_2017.pdf: 285283 bytes, checksum: 258d00de4d51d5f0c1878a247188f7b5 (MD5) Previous issue date: 2017Universidade Federal do Rio de Janeiro. Centro de Ciências da Saúde. Instituto Walter Mors de Pesquisa em Produtos Naturais. Rio de Janeiro, RJ, Brasil.Universidade Federal do Rio de Janeiro. Centro de Ciências da Saúde. Instituto Walter Mors de Pesquisa em Produtos Naturais. Rio de Janeiro, RJ, Brasil.Universidade Severino Sombra. Laboratório de Insetos Vetores. Vassouras, RJ, Brasil.Universidade Severino Sombra. Laboratório de Insetos Vetores. Vassouras, RJ, Brasil / Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório Interdisciplinar de Vigilância Entomológica em Diptera e Hemiptera. Rio de Janeiro, RJ. BrasilFundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Mosquitos Transmissores de Hematozoários. Rio e Janeiro, RJ, Brasil / Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Núcleo Operacional Sentinela de Mosquitos Vetores. Rio de Janeiro, RJ, Brasil.Universidade Federal do Rio de Janeiro. Centro de Ciências da Saúde. Instituto Walter Mors de Pesquisa em Produtos Naturais. Rio de Janeiro, RJ, Brasil.Universidade Severino Sombra. Laboratório de Insetos Vetores. Vassouras, RJ, Brasil / Universidade Severino Sombra. Curso de Mestrado Profissional em Ciências Ambientais. Curso de Mestrado Profissional em Ciências da Saúde. Vassouras, RJ, Brasil / Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Entomologia Médica e Forense. Rio de Janeiro, RJ, Brasil.Background & objectives: Aedes aegypti mosquito is the principal vector of the viruses responsible for urban yellow fever, dengue, dengue haemorrhagic fever, as well as Zika and chikungunya in Brazil. The present study was aimed to investigate the insecticidal potential of the extract and fractions of Ottonia anisum, along with special metabolites isolated from it, as natural alternatives against larvae (L3) of Ae. aegypti, vector of potentially deadly tropical infections in Brazil. Methods: The plant species O. anisum was collected in March 2015, at Xerém area, in Rio de Janeiro City, Brazil. Crude extracts and the isolated pure compounds were screened for toxicity against Ae. aegypti larvae (L3). Bioassays were performed on 20 larvae (L3) of Ae. aegypti in triplicate. The samples were dissolved in a mixture of acetone and DMSO at final concentrations of 1–200 μg/ml. The toxicity of the solutions was evaluated towards the growth and development of Ae. aegypti larvae till emergence of adults. Results: The crude hexane extract showed 100% larval mortality 24 h after treatment at a concentration of 200 μg/ ml. The bioassays using 1-butyl-3,4-methylenedioxybenzene revealed 100% mortality among L3 larvae, 24 h after the treatment at a concentration of 30 μg/ml, the LC50 recorded was 1.6 μg/ml. At concentration of 10 μg/ml, the L3 larval mortality recorded was 92%. Interpretation & conclusion: The metabolite 1-butyl-3,4-methylenedioxybenzene showed potent toxicity against Ae. aegypti larvae. This arylbutanoid agent could be used as a natural alternative adjuvant pesticide, in new compositions that would be environmentally safer

Larvicidal activity of Ottonia anisum metabolites against Aedes aegypti: A potential natural alternative source for mosquito vector control in Brazil

Background & objectives: Aedes aegypti mosquito is the principal vector of the viruses responsible for urban yellow fever, dengue, dengue haemorrhagic fever, as well as Zika and chikungunya in Brazil. The present study was aimed to investigate the insecticidal potential of the extract and fractions of Ottonia anisum, along with special metabolites isolated from it, as natural alternatives against larvae (L3) of Ae. aegypti, vector of potentially deadly tropical infections in Brazil. Methods: The plant species O. anisum was collected in March 2015, at Xerém area, in Rio de Janeiro City, Brazil. Crude extracts and the isolated pure compounds were screened for toxicity against Ae. aegypti larvae (L3). Bioassays were performed on 20 larvae (L3) of Ae. aegypti in triplicate. The samples were dissolved in a mixture of acetone and DMSO at final concentrations of 1-200 μg/ml. The toxicity of the solutions was evaluated towards the growth and development of Ae. aegypti larvae till emergence of adults. Results: The crude hexane extract showed 100% larval mortality 24 h after treatment at a concentration of 200 μg/ ml. The bioassays using 1-butyl-3,4-methylenedioxybenzene revealed 100% mortality among L3 larvae, 24 h after the treatment at a concentration of 30 μg/ml, the LC50 recorded was 1.6 μg/ml. At concentration of 10 μg/ml, the L3 larval mortality recorded was 92%. Interpretation & conclusion: The metabolite 1-butyl-3,4-methylenedioxybenzene showed potent toxicity against Ae. aegypti larvae. This arylbutanoid agent could be used as a natural alternative adjuvant pesticide, in new compositions that would be environmentally safer

C-glycosyl flavones from Peperomia blanda

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 mu M for 1, and 90.5 mu M for 2. (C) 2008 Elsevier B.V. All rights reserved.CNPqConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)FAPERJFAPERJFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)FAPES

Atividade antinociceptiva do óleo essencial de Echinodorus macrophyllus(Kunth.) Micheli (Alismataceae)

Made available in DSpace on 2017-06-01T19:19:18Z (GMT). No. of bitstreams: 2 license.txt: 1748 bytes, checksum: 8a4605be74aa9ea9d79846c1fba20a33 (MD5) 4.pdf: 152195 bytes, checksum: 105e8d57d343b1ee75b29a96531ee987 (MD5) Previous issue date: 29Universidade do Estado do Rio de Janeiro. Departamento de Bioquímica do Instituto de Biologia Roberto Alcantara Gomes. Centro Biomédico. Laboratório de Imunologia Aplicada e Bioquímica de Proteínas e Produtos Naturais. Rio de Janeiro, RJ, Brasil.Universidade do Estado do Rio de Janeiro. Departamento de Bioquímica do Instituto de Biologia Roberto Alcantara Gomes. Centro Biomédico. Laboratório de Imunologia Aplicada e Bioquímica de Proteínas e Produtos Naturais. Rio de Janeiro, RJ, Brasil.Universidade do Estado do Rio de Janeiro. Departamento de Bioquímica do Instituto de Biologia Roberto Alcantara Gomes. Centro Biomédico. Laboratório de Imunologia Aplicada e Bioquímica de Proteínas e Produtos Naturais. Rio de Janeiro, RJ, Brasil.Universidade do Estado do Rio de Janeiro. Departamento de Bioquímica do Instituto de Biologia Roberto Alcantara Gomes. Centro Biomédico. Laboratório de Imunologia Aplicada e Bioquímica de Proteínas e Produtos Naturais. Rio de Janeiro, RJ, Brasil.Universidade do Estado do Rio de Janeiro. Departamento de Bioquímica do Instituto de Biologia Roberto Alcantara Gomes. Centro Biomédico. Laboratório de Imunologia Aplicada e Bioquímica de Proteínas e Produtos Naturais. Rio de Janeiro, RJ, Brasil.Universidade do Estado do Rio de Janeiro. Departamento de Bioquímica do Instituto de Biologia Roberto Alcantara Gomes. Centro Biomédico. Laboratório de Imunologia Aplicada e Bioquímica de Proteínas e Produtos Naturais. Rio de Janeiro, RJ, Brasil.Universidade do Estado do Rio de Janeiro. Departamento de Bioquímica do Instituto de Biologia Roberto Alcantara Gomes. Centro Biomédico. Laboratório de Imunologia Aplicada e Bioquímica de Proteínas e Produtos Naturais. Rio de Janeiro, RJ, Brasil.Universidade do Estado do Rio de Janeiro. Departamento de Bioquímica do Instituto de Biologia Roberto Alcantara Gomes. Centro Biomédico. Laboratório de Imunologia Aplicada e Bioquímica de Proteínas e Produtos Naturais. Rio de Janeiro, RJ, Brasil.A Echinodorus macrophyllus (Kunth.) Mich., é uma planta de hábitos aquáticos, popularmente conhecido no Brasil como “chapéu de couro”, sendo utilizada no tratamento do reumatismo e outras afecções, comodiurético e antissifilítico.O objetivo do presente trabalho foi avaliar o efeito antinociceptivo do óleo essencial de Echinodorus macrophyllus (OEEm), obtido através da hidrodestilação em aparelho de Clevenger modificado. A análise de seu perfil cromatográfico por cromatografia com fase gasosa acoplada à espectrometria de massas (CG-EM) possibilitou a identificação de 21 componentes, sendo três majoritários (dilapiol, 2-tridecanona e óxido de cariofileno). Para a avaliação da atividade antinociceptiva do OEEm foi empregado o modelo de hiperalgesia induzido por injeção intraperitoneal (i.p.) de ácido acético. Camundongos Swiss Webster (SW) machos, que foram tratados com OEEm, por via oral (v.o.) nas doses de 50 e 100 mg/kg apresentaram inibição significativa das contorçõesinduzidas por ácido acético de 65% e 59%, respectivamente, em relação ao grupo controle. Esta atividade possivelmente está relacionada à inibição de receptores específicos da nocicepção, promovendo assim, a analgesia.Echinodorus macrophyllus (Kunth.) Mich. is a plant of aquatic habits popularly known in Brazil as “chapéu de couro”, being used for the treatment of rheumatism and other inflammatory diseases, as a diuretic and antisyphilitic. The aim of this study was to evaluate the antinociceptive effects of essential oil of Echinodorus macrophyllus (EOEm), obtained through hydrodistillation for two hours, in Clevenger-type modified apparatus. The EOEm chromatographic profile analyses on gas chromatography coupled to mass spectrometry (GC-MS) allowed the identification of 21 components which three are majority (dillapiole, 2-tridecanone and caryophyllene oxide). The evaluation of the antinociceptive activity of EOEm, was done using the hyperalgesia model induced by intraperitoneal (i.p.) injection of acetic acid. Swiss Webster (SW) male mice were orally (p.o.) treated with EOEm with 50 and 100 mg/kg EOEm doses (p.o.), showed significant inhibition of acetic acid-induced contortions by 65% and 59% respectively, compared with the control group. This activity possibly is related to the inhibition of nociception-specific receptors, thereby, analgesia

Local Anesthetic Activity from Extracts, Fractions and Pure Compounds from the Roots of Ottonia anisum Spreng. (Piperaceae)

ABSTRACT 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

3-Ishwarone, a Rare Ishwarane Sesquiterpene from Peperomia scandens Ruiz & Pavon: Structural Elucidation through a Joint Experimental and Theoretical Study

3-Ishwarone, (1), a sesquiterpene with a rare ishwarane skeleton, was isolated from Peperomia scandens Ruiz & Pavon (Piperaceae). Its structure was unambiguously determined by 1D- and 2D-NMR and infrared analyses, as well as by comparative theoretical studies which involved calculations of 13C-NMR chemical shifts, using the Density Functional Theory (DFT) with the mPW1PW91 hybrid functional and Pople’s 6-31G(d) basis set, and of vibrational frequencies, using the B3LYP hybrid functional and triple ζ Dunning’s correlation consistent basis set (cc-pVTZ), of (1) and three of its possible diastereomers, compounds 2–4

Non-Clinical Studies for Evaluation of 8-C-Rhamnosyl Apigenin Purified from Peperomia obtusifolia against Acute Edema

Compound 8-C-rhamnosyl apigenin (8CR) induced a moderate reduction in the enzymatic activity of secretory phospholipase A2 (sPLA2) from Crotalus durissus terrificus and cytosolic phospholipase A2 (cPLA2), but the compound also significantly inhibited the enzymatic activity of the enzyme cyclooxygenase. In vitro assays showed that the compound induced a slight change in the secondary structure of sPLA2 from Crotalus durissus terrificus snake venom. In vivo assays were divided into two steps. In the first step, the 8CR compound was administered by intraperitoneal injections 30 min prior to administration of sPLA2. In this condition, 8CR inhibited edema and myonecrosis induced by the sPLA2 activity of Crotalus durissus terrificus in a dose-dependent manner by decreasing interleukin-1β (IL-1β), tumor necrosis factor α (TNF-α), prostaglandin E2 (PGE2), and lipid peroxidation. This has been demonstrated by monitoring the levels of malondialdehyde (MDA) in rat paws after the course of edema induced by sPLA2. These results, for the first time, show that sPLA2 of Crotalus durissus terrificus venom induces massive muscle damage, as well as significant edema by mobilization of cyclooxygenase enzymes. Additionally, its pharmacological activity involves increased lipid peroxidation as well as TNF-α and IL-1β production. Previous administration by the peritoneal route has shown that dose-dependent 8CR significantly decreases the enzymatic activity of cyclooxygenase enzymes. This resulted in a decrease of the amount of bioactive lipids involved in inflammation; it also promoted a significant cellular protection against lipid peroxidation. In vivo experiments performed with 8CR at a concentration adjusted to 200 μg (8 mg/kg) of intraperitoneal injection 15 min after sPLA2 injection significantly reduced sPLA2 edema and the myotoxic effect induced by sPLA2 through the decrease in the enzymatic activity of cPLA2, cyclooxygenase, and a massive reduction of lipid peroxidation. These results clearly show that 8CR is a potent anti-inflammatory that inhibits cyclooxygenase-2 (COX-2), and it may modulate the enzymatic activity of sPLA2 and cPLA2. In addition, it was shown that Crotalus durissus terrificus sPLA2 increases cell oxidative stress during edema and myonecrosis, and the antioxidant properties of the polyphenolic compound may be significant in mitigating the pharmacological effect induced by sPLA2 and other snake venom toxins