Antifungal flavanones and prenylated hydroquinones from Piper crassinervium Kunth

Danelutte, Ana Paula; Lago, João Henrique G.; Young, Maria Cláudia M.; Kato, Massuo Jorge

doi:10.1016/s0031-9422(03)00299-1

Cited by 105 publications

(55 citation statements)

References 13 publications

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“…Since the 1 H NMR spectrum in CDCl 3 showed several overlapped signals at δ 1.0-2.5, this spectrum was recorded in C 6 D 6 (Table 1). Thus, three methyl groups splitted apart into two quarternary methyl groups at d 0.89 (s, 3H), 0.96 (s, 3H) and a secondary one at δ 1.25 (d, J 6.6 Hz, 3H) were observed.…”

Section: Resultsmentioning

confidence: 99%

“…[1][2][3][4] The genus Peperomia has over 1000 species occurring in the tropics, its leaves have a variety of size and shape and are adapted to moist habitat and dry highlands as well. In despite of the large number of Peperomia species, only a few species have been chemically analyzed and, as a result, amides, chromenes, benzoic acids, lignoids and poliketide derivatives were isolated.…”

Section: Introductionmentioning

confidence: 99%

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3-Ishwarone and 3-Ishwarol, rare sesquiterpenes in essential oil from leaves of Peperomia oreophila Hensch.

Lago¹,

Oliveira

Guimarães³

et al. 2007

J. Braz. Chem. Soc.

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O óleo essencial obtido das folhas de Peperomia oreophila (Piperaceae) foi submetido a fracionamento em gel de sílica. Esse processo de separação resultou em uma fração composta por uma mistura de hidrocarbonetos sesquiterpênicos que foram identificados como β-elemeno, α-ilangeno, α-guaieno e β-selineno. Além desses, também foram identificados o espatulenol e dois sesquiterpenos com raro esqueleto ishwarano: o 3-ishwarol e a 3-ishwarona, sendo esta última, o componente majoritário do óleo bruto (78% em massa). Uma vez que o álcool foi obtido em quantidade insuficiente para caracterização estrutural, maiores quantidades foram obtidas por meio da redução da cetona original. Os dois sesquiterpenos foram purificados e depois caracterizados por meio de técnicas espectrométricas ( 1 H-1 H COSY, HMQC, HMBC e NOESY).The essential oil from Peperomia oreophila leaves (Piperaceae) was submitted to fractionation in silica gel column. This separation procedure yielded a fraction composed of a hydrocarbon sesquiterpene mixture which was identified as β-elemene, α-ylangene, α-guaiene and β-selinene. Besides, spathulenol and two sesquiterpenes with the rare ishwarane skeleton: 3-ishwarol and 3-ishwarone were also identified. 3-ishwarone was the major component of the crude oil (78% weight). Since the alcohol obtained was not sufficient to allow a complete structural determination, the original ketone was reduced to 3-ishwarol in order to give additional quantities. After the two sesquiterpenes purification, they were characterized by spectrometric techniques ( 1 H-1 H COSY, HMQC, HMBC and NOESY).

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

3-Ishwarone and 3-Ishwarol, rare sesquiterpenes in essential oil from leaves of Peperomia oreophila Hensch.

Lago¹,

Oliveira

Guimarães³

et al. 2007

J. Braz. Chem. Soc.

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“…2 Espécies de Piperaceae têm sido utilizadas na alimentação (como condimento -Piper nigrum), 3 como inseticidas 4 e, também, na medicina tradicional devido ao acúmulo de diferentes classes de metabólitos biologicamente ativos, tais como fenilpropanóides, 5 lignanas/neolignanas, 6-10 pironas, 11 amidas alífáticas e aromáticas, [12][13][14] alcalóides, 15 policetídeos 16 e cromenos, [17][18][19][20][21][22] além de outros metabólitos de biossíntese mista. 7,23,24 As espécies de Piperaceae estão sendo subdivididas em quatro gêneros, 25 sendo que os mais abundantes são Peperomia Ruiz e Pavon, com aproximadamente 1700 espécies 26 e Piper L., com cerca de 2000 espécies. 27 Muitos gêneros foram incluídos como sinonímias dentro do gênero Piper, por exemplo, Arctottonia Trel., Macropiper Miq., Pothomorphe Miq., Ottonia Spreng., e Trianaeopiper Trel.…”

Section: Introductionunclassified

Flavonas, lignanas e terpeno de Piper umbellata (Piperaceae)

et al. 2009

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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%

“…and P. crassinervium Kunth. Although the non-volatile constitution of all four species have already been reported, 2,6,[17][18][19] the essential oils of P. tuberculatum and P. crassinervium are being reported for the first time. During referee assessment of this paper a report of the essential oils from eleven different plant species, including P. crassinervium, came out in the literature.…”

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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Antifungal flavanones and prenylated hydroquinones from Piper crassinervium Kunth

Cited by 105 publications

References 13 publications

3-Ishwarone and 3-Ishwarol, rare sesquiterpenes in essential oil from leaves of Peperomia oreophila Hensch.

3-Ishwarone and 3-Ishwarol, rare sesquiterpenes in essential oil from leaves of Peperomia oreophila Hensch.

Flavonas, lignanas e terpeno de Piper umbellata (Piperaceae)

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

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