Meroterpenes from Peperomia oreophila Hensch and Peperomia arifolia Miq.

One new meroterpene, 4-[(2'E)-3',7'-dimethylocta-2',6'-dien-1'-yl]-5-methyl-2-(3 ''-methylbut-2 ''-enyl)-benzene-1,3-diol, together with eight known compounds, was isolated from the MeOH extract from the leaves of Peperomia oreophila Hesch. The prenylated phenol was also isolated as main compound from the CH2Cl2:MeOH extract from leaves of Peperomia arifolia Miq. The structures of the substances were established on the basis of the spectral evidences and supported by literature data.Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq)Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq)Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior (CAPES)Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior (CAPES)Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP)Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) [2009/51850-9

Leishmanicidal activity of an alkenylphenol from Piper malacophyllum is related to plasma membrane disruption

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 EC50 of 23 mu g/mL against axenic promastigotes and an EC50 of 22 mu g/mL against intracellular amastigotes. Gibbilimbol B was also tested for anti-trypanosomal activity (Trypanosoma cruzi) and showed an EC50 value of 17 mu g/mL against trypomastigotes. To evaluate the cytotoxic parameters, this alkenylphenol was tested in vitro against NCTC cells, showing a CC50 of 59 mu g/mL and absent hemolytic activity at the highest concentration of 75 mu g/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. (C) 2012 Elsevier Inc. All rights reserved.FAPESPCNP

Prenylated benzoic acid derivatives from Piper aduncum L. and P. hostmannianum C. DC. (Piperaceae)

The bioactivity-guided fractionation of the crude extracts from leaves of Brazilian species Piper aduncum and Piper hostmannianum by means of bioautography using the fungi Cladosporium cladosporioides and C. sphaerospermum afforded prenylated methyl benzoate, chromenes, and dihydrobenzopyran derivatives as antifungal compounds. The isolation and structural elucidation of a new compound methyl 4-hydroxy-3-(2`-hydroperoxy-3`-methyl-3`-butenyl) benzoate were performed by application of chromatographic techniques and spectroscopic analyses. (C) 2009 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.FAPESPFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)CNP

Caldensinic acid, a prenylated benzoic acid from Piper caldense

The CH(2)Cl(2) and MeOH extracts from leaves of Piper caldense were subjected to chromatographic separation procedures to afford the new prenylated benzoic acid, caldensinic acid (3-[(2`E,6`E,10`E)-11`-carboxy-3`,7`,15`-trimethylhexadeca-2`,6`,10`,14`-tetraenyl]-4,5-dihydroxybenzoic acid) whose structure was determined by spectral analysis, mainly NMR ((1)H, (13)C, HSQC, HMBC) and ESI-MS. The natural compound and derivatives displayed antifungal activity against the phytopathogenic fungi Cladosporium cladosporioides and C. sphaerospermum by direct bioautography. (C) 2009 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)FAPESPMackPesquisaMackPesquisaConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)CNP

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

Antioxidant Capacity and Larvicidal and Antifungal Activities of Essential Oils and Extracts from Piper krukoffii

The leaves and twigs of Piper krukoffii, collected in the Carajas 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 EC(50) values varied from the ethyl acetate sub-fraction (73.4 +/- 3.7 mu g/mL) to the methanol extract (24.9 +/- 0.8 mu g/mL), and the ABTS TEAC values ranged in the same order from 265.7 to 349.2 mu Mol 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 (1)H 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 mu g/mL) and fungicide (0.5 and 0.1 mu g/mL) activities.MCT/PPBioMCT/PPBioConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)CNPqFAPESPA/PAFAPESPA/P

Antifungal and Cytotoxic 2-Acylcyclohexane-1,3-diones from Peperomia alata and P. trineura

Bioactivity-guided fractionation of the separate CH2Cl2 extracts from the aerial parts of Peperornia 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'-methylenedioxy-pentadecanoyl)cyclohex-2-en-1-one, 2b], trineurone C [3-hydroxy-2(17'-phenyl-20'-methylen edioxyheptadecanoyl)cyclohex-2-en-1-one, 2c], trineurone D [3-hydroxy-2-(hexadec-10'Z-enoyl)cyclohex-2-en-1one, 3a], and trineurone E [(6R)-(+)-3,6-dihydroxy-2-(hexadec-10'Zenoyl)cyclohex-2-en-l-one, 3b] from P. trineura. the isolated compounds were evaluated for antifimgal activity against Cladosporium cladosporioides and C. sphaeospermum and for cytotoxicity against the 1(562 and Nalm-6 leukemia cell lines.Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Univ São Paulo, Inst Chem, Res Support Ctr Mol Div Nat Prod, BR-05508000 São Paulo, BrazilInst Bot, Secao Fisiol & Bioquim Plantas, BR-04301012 São Paulo, BrazilInst Pesquisa Jardinn Bot Rio de Janeiro, BR-22460030 Rio de Janeiro, RJ, BrazilUniv Estadual Campinas, Ctr Integrado Pesquisas Oncohematol Infancia, BR-13083970 Campinas, SP, BrazilUniversidade Federal de São Paulo, Dept Ciencias Exatas & Terra, Inst Ciencias Ambientais Quim & Farmaceut, BR-09972270 Diadema, SP, BrazilUniversidade Federal de São Paulo, Dept Ciencias Exatas & Terra, Inst Ciencias Ambientais Quim & Farmaceut, BR-09972270 Diadema, SP, BrazilWeb of Scienc

Chemical study and larvicidal activity against Aedes aegypti of essential oil of Piper aduncum L. (Piperaceae)

ABSTRACT 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 24h of treatment with the oil at concentrations of 500 and 1,000 ppm. After 48h 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 48h was 134.1 ppm. The major compound 1,8-cineole showed no larvicidal activity