Quantitative determination of anti‐fungal and insecticide amides in adult plants, plantlets and callus from <i>Piper tuberculatum</i> by reverse‐phase high‐performance liquid chromatography

Navickiene, Hosana Maria Debonsi; Bolzani, Vanderlan da Silva; Kato, Massuo Jorge; Pereira, Ana Maria Soares; Bertoni, Bianca Waléria; França, Suzelei de Castro; Furlan, Maysa

doi:10.1002/pca.716

Cited by 45 publications

(32 citation statements)

References 19 publications

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“…In the case of P. aduncum, the major component, the phenylpropanoid dillapiol, was present together with apiol, myristicin, and elemicin in the volatile fractions derived from both seedlings and adult plants. Moreover, the major amides of P. tuberculatum were present in all tissues of the adult plants and in in vitro plantlets [49]. On the other hand, the two well-investigated species, P. regnellii and P. solmsianum, contained dihydrobenzofuran (conocarpan) and tetrahydrofuran neolignans (e.g., grandisin), respectively, as major compounds only in adult tissues [14,50].…”

Section: Dynamics Of Secondary Metabolism During Development and Diffmentioning

confidence: 99%

Chemistry and evolution of the Piperaceae

Kato

Furlan

2007

Pure and Applied Chemistry

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114

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Abstract:The chemistry of members of the family Piperaceae is of great interest owing to the variety of biological properties displayed. A survey of structural diversity and bioactivity reveals that groups of species specialize in the production of amides, phenylpropanoids, lignans and neolignans, benzoic acids and chromenes, alkaloids, polyketides, and a plethora of compounds of mixed biosynthetic origin. Bioassays against Cladosporium cladosporioides and C. sphaerospermun have resulted in the characterization of various amides, prenylated phenolic compounds, and polyketides as potential classes of antifungal agents. Studies on the developmental process in seedlings of Piper solmsianum have shown that phenylpropanoid are produced instead of the tetrahydrofuran lignans found in adult plants. In suspension cultures of P. cernuum and P. crassinervium, phenylethylamines and alkamides predominate, whereas in the adult plants prenylpropanoids and prenylated benzoic acids are the respective major compound classes. Knowledge of the chemistry, bioactivity, and ecology of Piperaceae species provides preliminary clues for an overall interpretation of the possible role and occurrence of major classes of compounds.

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Section: Dynamics Of Secondary Metabolism During Development and Diffmentioning

confidence: 99%

Chemistry and evolution of the Piperaceae

Kato

Furlan

2007

Pure and Applied Chemistry

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114

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“…Besides being of high commercial and economical importance, Piper species are medicinally used in different ways, such as in the Indian Ayurvedic system of medicine and in the folklore medicine of Latin America and the West Indies (Parmar et al 1997). Piper species produce many biologically active compounds, including amides, flavanones, alkaloids, propenylphenols, lignans, neolignans, benzoic acids and chromenes (Parmar et al 1997;Navickiene et al 2003;Silva et al 2002;Danelutte et al 2003;Martins et al 2003;Lago et al 2004).…”

Section: Introductionmentioning

confidence: 99%

In vitro morphogenesis and cell suspension culture establishment in Piper solmsianum C. DC. (Piperaceae)

et al. 2009

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RESUMO -(Morfogênese in vitro e estabelecimento de culturas de suspensão celular em Piper solmsianum C. DC. (Piperaceae)). Piper solmsianum é uma espécie herbácea do sudeste brasileiro onde vários compostos biologicamente ativos já foram identificados. O objetivo deste trabalho foi estabelecer suspensões celulares nesta espécie. Para tanto, foram utilizados explantes de pecíolos e folhas, retirados de plântulas cultivadas in vitro, os quais foram submetidos a diferentes combinações de reguladores de crescimento (AIA, ANA, 2,4-D e BAP). Foi obtida a neo-formação de raízes e brotos, estes últimos através do processo de organogênese indireta evidenciada por estudos histológicos. Para a indução e crescimento dos calos, foram avaliados, além das diferentes combinações de reguladores de crescimento, a suplementação ao meio de cultura de carvão ativado (1,5 mg.l -1 ) e o regime de luz. Culturas mantidas na luz, em meio de cultura suplementado com 0,2 mg.l -1 2,4-D e 2 mg.l -1 BAP e sem carvão ativado, resultaram em maior crescimento (massa fresca) dos calos. A partir destes calos, foram obtidas suspensões celulares, cuja dinâmica de crescimento e acúmulo de metabólitos foi estudado. Os resultados obtidos deverão ser utilizados para a caracterização de rotas biosintéticas em culturas in vitro em P. solmsianum. Palavras-chave: calogênese, morfogênese, pariparoba, reguladores de crescimento, suspensões celulares ABSTRACT -(In vitro morphogenesis and cell suspension culture establishment in Piper solmsianum C. DC. (Piperaceae)).Piper solmsianum is a shrub from Southeast Brazil in which many biologically active compounds were identified. The aim of this work was to establish a cell suspension culture system for this species. With this in mind, petiole and leaf explants obtained from in vitro plantlets were cultured in the presence of different plant growth regulator combinations (IAA, NAA, 2,4-D and BA). Root and indirect shoot adventitious formation, detected by histological analysis, was observed. Besides the different combinations of plant growth regulators, light regime and the supplement of activated charcoal (1.5 mg.l -1 ) were tested for callus induction and growth. Cultures maintained in light, on a 0.2 mg.l -1 2,4-D and 2 mg.l -1 BA supplemented medium, and in the absence of activated charcoal, showed the highest calli fresh matter increment. From a callus culture, cell suspension cultures were established and their growth and metabolite accumulation studied. The achieved results may be useful for further characterization of the activated secondary metabolites pathways in in vitro systems of P. solmsianum.

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“…10,11) With regard to the ethnopharmacological information, while the pungent and aromatic fruits of some species of Piper are used as spices, most of them find wide application in traditional systems of medicine 10,11) as insecticides, 7,[12][13][14] antivirals, 15,16) antimicrobials [17][18][19][20][21] and particularly antifungals. [22][23][24][25][26][27][28] These biological properties have been attributed to the presence of lignans and/or amides, such as alkyl or olefinic isobutylamides, 7,23,29) flavonoids, kawa-lactones, butenolides and cyclohexane epoxides, among others. 10) Among the different species of Piper growing in Brazil, Piper solmsianum (syn.…”

mentioning

confidence: 99%

Evaluation of Antifungal Activity of Piper solmsianum C. DC. var. solmsianum (Piperaceae)

Campos

Filho

Silva

et al. 2005

Biological & Pharmaceutical Bulletin

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The incidence of opportunistic fungal infections in immunocompromised patients, such as those undergoing treatment with immunosuppressive drugs, intensive chemotherapy, AIDS patients and neonates, is increasing at an alarming rate. 1,2) These mycoses are very difficult to eradicate, and present an enormous challenge for healthcare providers. 3,4) The diversity of plant species in Brazil, together with their known ethnopharmacological uses, creates enormous potential for finding new structures with antifungal properties. 5,6) The Piperaceae is a vast family of plants, which has been extensively used for medicinal purposes.7) It comprises about 10 genus and approximately 2000 species, most of them herbaceous, 8) which are found mainly in tropical areas. Piper and Peperomia, the two greatest genera of the family, are well-represented in the Brazilian flora. 9)Within the Piperaceae family, the genus Piper has over 700 species, distributed throughout the tropical and subtropical regions of the world. Its phytochemistry has been object of extensive reviews. 10,11) With regard to the ethnopharmacological information, while the pungent and aromatic fruits of some species of Piper are used as spices, most of them find wide application in traditional systems of medicine 10,11) as insecticides, 7,[12][13][14] antivirals, 15,16) antimicrobials [17][18][19][20][21] and particularly antifungals. [22][23][24][25][26][27][28] These biological properties have been attributed to the presence of lignans and/or amides, such as alkyl or olefinic isobutylamides, 7,23,29) flavonoids, kawa-lactones, butenolides and cyclohexane epoxides, among others. 10)Among the different species of Piper growing in Brazil, Piper solmsianum (syn. P. leucathum or P. santosanum) known popularly as "pariparoba", is a shrub that measures 1-3 m. There are few reports on the chemical or biological studies of this plant. In contrast, phytochemical studies indicated the presence of aliphatic hydrocarbons, monoterpenes, sesquiterpenes, arylpropanoids and neolignans. [30][31][32] Recently, we have demonstrated that the fractions and some pure compounds (lignans) from the leaves of this plant exhibit significant activity against Gram-positive bacteria. 33)The current study extends our previous work on the biological properties of P. solmsianum and describes the in vitro antifungal activity of extracts, fractions and pure compounds against a panel of opportunistic pathogenic fungi using the agar dilution method. MATERIALS AND METHODS Plant MaterialPiper solmsianum C. DC. var. solmsianum (Piperaceae) was collected in May, 2001, in Ponta Grossa, State of Paraná, Brazil, and identified by Dr. Elsie Franklin Guimarães (Rio de Janeiro Botanic Museum Herbarium). A voucher specimen was deposited in the same herbarium under the number RB 368597.Phytochemical Analyses Air-dried leaves (1.36 kg) of P. solmsianum var. solmsianum were cut into small pieces and macerated at room temperature for one week in methanol. After filtration, the solvent was removed by rotary evaporat...

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Quantitative determination of anti‐fungal and insecticide amides in adult plants, plantlets and callus from Piper tuberculatum by reverse‐phase high‐performance liquid chromatography

Cited by 45 publications

References 19 publications

Chemistry and evolution of the Piperaceae

Chemistry and evolution of the Piperaceae

In vitro morphogenesis and cell suspension culture establishment in Piper solmsianum C. DC. (Piperaceae)

Evaluation of Antifungal Activity of Piper solmsianum C. DC. var. solmsianum (Piperaceae)

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