Three new natural cyclopentenedione derivatives from Piper carniconnectivum

Facundo, Valdir Alves; Sá, Amanda L; Silva, Silane A. F; Morais, Selene Maia de; Matos, Carlos Roberto Ribeiro; Braz-Filho, Raimundo

doi:10.1590/s0103-50532004000100022

Cited by 23 publications

(29 citation statements)

References 2 publications

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“…Several plants of this genus are largely used in folk medicine in several parts of the world and have been reported to produce compounds with diverse biological and pharmacological properties. [2][3][4][5][6][7][8] Many Piper species are aromatic and as a consequence the chemical composition of the essential oils of several of them has been the subject of incessant studies, revealing a diverse range of volatile components, including monoterpenes, sesquiterpenes, arylpropanoids, aldehydes, ketones and long chain alcohols. [9][10][11][12][13][14][15][16] Pursuing the determination of the chemical composition of essential oils from aromatic and medicinal plants from Northeast of Brazil flora, especially from the State of Ceará, we are reporting now the results of the investigation of four Piper species: P. dilatatum L.C.…”

Section: Introductionmentioning

confidence: 99%

Leaf essential oils of four Piper species from the State of Ceará - Northeast of Brazil

Cysne

Canuto

Pessoa

et al. 2005

J. Braz. Chem. Soc.

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Os óleos essenciais obtidos por hidrodestilação das folhas de quatro espécies de Piper (P. arboreum, P. crassinervium, P. dilatatum and P. tuberculatum), coletadas no estado do Ceará, foram analisados por CG-EM. Os rendimentos dos óleos, calculados sobre o peso do material fresco, variaram entre 0,03 -0,11% (p/p). Os óleos foram caracterizados pela presença de mono-e sesquiterpenos, exceto o óleo de P. arboreum, no qual foram identificados apenas sesquiterpenos. β-Elemeno (0,58-3,03%), (E)-cariofileno (2,71-37,78%), germacreno D (3,43-11,81%), biciclogermacreno (2,83-25,07%) e δ-cadineno (0,52-2,44%) foram detectados em todas as amostras analisadas. Os monoterpenos majoritários identificados foram α-pineno (11,27%), β-pineno (20,01%), 1,8-cineol (10,81%) e linalol (28,61%) para P. crassinervium, e α-felandreno (22,53%) e ∆-3-careno (10,20%) para P. dilatatum. Biciclogermacreno (25,03 e 25,07%) para P. arboreum e P. dilatatum, (E)-nerolidol (11,12%) para P. arboreum, germacreno D (11,81%) para P. tuberculatum e (E)-cariofileno (10,26 e 37,78%) para P. dilatatum e P. tuberculatum, foram os principais sesquiterpenos. Este trabalho descreve, pela primeira vez, a composição química dos óleos essenciais de P. crassinervium e P. tuberculatum.The essential oils, obtained by hydrodistillation, from leaf samples of four Piper species (P. arboreum, P. crassinervium, P. dilatatum and P. tuberculatum), harvested at the State of Ceará, were analyzed by GC-MS. The oil yields ranged from 0.03 to 0.11% (w/w), on fresh weight basis. The oils were characterized by mono-and sesquiterpenes, except the oil of P. arboreum to which only sesquiterpenes were identified. β-Elemene (0.58-3.03%), (E)-caryophyllene (2.71-37.78%), germacrene D (3.43-11.81%), bicyclogermacrene (2.83 and 25.07%) and δ-cadinene (0.52-2.44%) were detected in all oil samples. The major identified monoterpenes were α-pinene (11.27%), β-pinene (20.01%), 1,8-cineole (10.81%) and linalool (28.61%) for P. crassinervium and, α-phellandrene (22.53%) and ∆-3-carene (10.20%) for P. dilatatum. The major sesquiterpenes were bicyclogermacrene (25.03 and 25.07%) for P. arboreum and P. dilatatum, (E)-nerolidol (11.12%) for P. arboreum, germacrene D (11.81%) for P. tuberculatum and, (E)-caryophylene (10.26 and 37.78%) for P. dilatatum and P. tuberculatum. To the best of our knowledge this is the first report about the chemical composition of the leaf essential oils of P. crassinervium and P. tuberculatum.

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Section: Introductionmentioning

confidence: 99%

Leaf essential oils of four Piper species from the State of Ceará - Northeast of Brazil

Cysne

Canuto

Pessoa

et al. 2005

J. Braz. Chem. Soc.

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“…Vá-rias destas espécies são utilizadas na medicina popular no tratamento de doenças cardiovasculares, tuberculose, malária, para aliviar dor de dente e contra mordida de cobra [6][7][8][9] . O estudo fitoquímico de duas espécies comuns do nordeste do Brasil, Z. syncarpum e Z. rugosum, conduziu ao isolamento dos metabólitos secundários skimianina, cis-N-metilcanadina, isopimpinelina, xantotoxina, lupeol, ácido centipédico, 3β-O-β-D-glucopiranosil-sitosterol, 6-cantinona, 6,7-dimetoxicumarina, 6,7,8-trimetoxicumarina, avicenina, hesperidina, ácido 3-(9H-β-carbolina-1-il)-(Z)-2-propenóico e 2-hidróxi-2-(4-hidroxifenil)etil (trimetil) amônio 10,11 .…”

Section: Introductionunclassified

Constituintes químicos de Zanthoxylum ekmanii (URB.) Alain

Facundo¹,

Silveira²,

Braz-Filho³

et al. 2005

Quím. Nova

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Recebido em 17/2/04; aceito em 9/9/04; publicado na web em 17/2/05 CHEMICAL CONSTITUENTS OF Zanthoxylum ekmanii (URB.) ALAIN. Chemical investigation of Z. ekmanii resulted in the isolation of skimmianine, dictamnine, tembamide, sesamin, lupeol and β-sitosterol. The structures were established by spectroscopic analyses. This is the first report on the phytochemical study of the roots and leaves of Z. ekmanii .

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“…The cyclopentenedione (1a/1b) ( Figure 1) is a new natural cyclopentenedione derivative that was isolated recently by Braz-Filho and coworkers 1 from the roots of a specimen of Piper carniconnectivum, collected in Porto Velho, Rondônia, in the northern part of Brazil. This specimen belongs to the tropical Piperaceae family, that comprises many important plants, very useful in folk medicine as bioproducers of essential oils.…”

Section: Introductionmentioning

confidence: 99%

“…2,3 The structure of cyclopentenedione derivative (1) was established by spectroscopic data, mainly 1D and 2D NMR as well as by Electron Impact Mass Spectrometry (EIMS). 1 According to the authors, 1 the isolated cyclopentenedione derivative may have structure 1a or 1b or even exist as an equilibrium mixture between these two enol forms showing average 1 H and 13 C NMR spectra due to a proposed rapid interconversion between 1a and 1b.…”

Section: Introductionmentioning

confidence: 99%

“…In connection with our interest in the total synthesis of natural products isolated from Brazilian sources, we became interested in the synthesis of the cyclopentenedione derivative (1). An efficient and flexible synthesis of this very interesting natural product is important to provide further material for biological studies, along with access to novel analogues, as well as to prove the assignment given by Braz-Filho and coworkers.…”

Section: Introductionmentioning

confidence: 99%

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Short synthesis of a new cyclopentene-1,3-dione derivative isolated from Piper carniconnectivum

Dias¹,

Shimokomaki²,

Shiota³

2005

J. Braz. Chem. Soc.

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A síntese total da ciclopentenodiona (1), isolada das raízes de Piper carniconnectivum, é descrita em 8 etapas e 11% de rendimento global a partir do 2-acetilfurano, fornecendo uma mistura 57:43 dos dois possíveis isômeros geométricos 1a e 1b.The total synthesis of cyclopentene-1,3-dione (1), a new natural cyclopentenedione derivative isolated from the roots of Piper carniconnectivum, is described in 8 steps and 11% overall yield from 2-acetylfuran, giving a 57:43 mixture of the two possible geometric isomers 1a and1b.

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Three new natural cyclopentenedione derivatives from Piper carniconnectivum

Cited by 23 publications

References 2 publications

Leaf essential oils of four Piper species from the State of Ceará - Northeast of Brazil

Leaf essential oils of four Piper species from the State of Ceará - Northeast of Brazil

Constituintes químicos de Zanthoxylum ekmanii (URB.) Alain

Short synthesis of a new cyclopentene-1,3-dione derivative isolated from Piper carniconnectivum

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