Antioxidant activity of prenylated hydroquinone and benzoic acid derivatives from Piper crassinervium Kunth

Yamaguchi, Lydia F.; Lago, João Henrique G.; Tanizaki, Tatiane M.; Mascio, Paolo Di; Kato, Massuo Jorge

doi:10.1016/j.phytochem.2006.03.001

Cited by 61 publications

(33 citation statements)

References 18 publications

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“…The significant antioxidant activity of prenylated hydroquinones, in comparison with hydroquinone itself, to inhibit lipoperoxidation is likely due to the presence of the lipophilic prenyl group that facilitates insertion of the molecule into the liposome in the model assay. Prenylated hydroquinones with a 2E-configuration exhibited higher activities than their corresponding 2Z-isomers, probably owing to better insertion into the liposome [40]. The presence of alkylated phenolic compounds in a number of Piper species suggests that this genus might represent a promising target in further searches for compounds with important antioxidant properties.…”

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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confidence: 99%

Chemistry and evolution of the Piperaceae

Kato

Furlan

2007

Pure and Applied Chemistry

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114

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“…The geranylmethoxyphenol 6 (isolated from Piper crassinervium Kunth) showed antioxidant activity [16], whereas the linear geranylmethoxyphenol/ acetates 7-9 (see figure 1), isolated from Phacelia ixodes [5], showed a biological activity which allows to repel and in some cases, to kill phytophagous insects and plant pathogens [17].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and NMR Structure Determination of New Linear Geranylphenols by Direct Geranylation of Activated Phenols

Taborga

Vergara

Osorio

et al. 2013

J. Chil. Chem. Soc.

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The known geranylhydroquinone 2, geranylorcinol 4 and the derivative (E)-4-(3,7-dimethylocta-2,6-dienyl)-5-methylbenzene-1,3-diol 5, were prepared by Electrophilic Aromatic Substitution (EAS) reactions between the corresponding phenol derivatives containing electron-donor subtituents and geraniol using BF 3 ×OEt 2 as a catalyst. In addition, spectroscopic NMR information for 4 and 5 is complemented. Furthermore, the new (E)-2-(3,7-dimethylocta-2,6-dienyl) benzene-1,3,5-triol (geranylphloroglucinol) 13, (E)-2-(3,7-dimethylocta-2,6-dienyl)-1,3,5-trimethoxybenzene 14, (E)-2-(3,7-dimethylocta-2,6-dienyl)-6-methoxyphenol 15, (E)-3-(3,7-dimethylocta-2,6-dienyl)-2-methoxyphenol 16, (E)-5-(3,7-dimethylocta-2,6-dienyl)-2-methoxyphenol 17, (E)-4-(3,7-dimethylocta-2,6-dienyl)benzene-1,3-diol 18, (E)-3-(3,7-dimethylocta-2,6-dienyl)benzene-1,2-diol 19, (E)-4-(3,7-dimethylocta-2,6-dienyl)-5-isopropyl-2-methylphenol 20, (E)-2-(3,7-dimethylocta-2,6-dienyl)-4-isopropyl-3-methylphenol 21, (E)-2-(3,7-dimethylocta-2,6-dienyl)-4-isopropyl-5-methylphenol 22, and(E)-2-tert-butyl-4-(3,7-dimethylocta-2,6-dienyl)-5-methylphenol 23 were also prepared with this synthesis strategy. All the synthesized compounds were fully characterized and their structures were established by IR, MS and mainly NMR spectroscopic dates.

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“…Plants from the genus Piper are widely distributed throughout tropical and subtropical regions. Brazil has several species and promising studies on biological properties of plants of the Piperaceae family have been published (Navickiene et al, 2000;Danelutte et al, 2003Danelutte et al, , 2005Cysne et al, 2005;Yamaguchi et al, 2006).…”

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confidence: 99%

Molluscicidal and ovicidal activities of plant extracts of the Piperaceae on Biomphalaria glabrata (Say, 1818)

et al. 2010

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Schistosomiasis is a tropical disease caused by Schistosoma and occurs in 54 countries, mainly in South America, the Caribbean region, Africa and the eastern Mediterranean. Currently, 5 to 6 million Brazilian people are infected and 30,000 are under infection risk. Typical of poor regions, this disease is associated with the lack of basic sanitation and very frequently to the use of contaminated water in agriculture, housework and leisure. One of the most efficient methods of controlling the disease is application of molluscicides to eliminate or to reduce the population of the intermediate host snail Biomphalaria glabrata. Studies on molluscicidal activity of plant extracts have been stimulated by issues such as environmental preservation, high cost and recurrent resistance of snails to synthetic molluscicides. The aim of this study was to determine the molluscicide action of extracts from Piperaceae species on adult and embryonic stages of B. glabrata. Fifteen extracts from 13 Piperaceae species were obtained from stems, leaves and roots. Toxicity of extracts was evaluated against snails at two different concentrations (500 and 100 ppm) and those causing 100% mortality at 100 ppm concentration were selected to obtain the LC 90 (lethal concentration of 90% mortality). Piper aduncum, P. crassinervium, P. cuyabanum, P. diospyrifolium and P. hostmannianum gave 100% mortality of adult snails at concentrations ranging from 10 to 60 ppm. These extracts were also assayed on embryonic stages of B. glabrata and those from P. cuyabanum and P. hostmannianum showed 100% ovicidal action at 20 ppm.

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Antioxidant activity of prenylated hydroquinone and benzoic acid derivatives from Piper crassinervium Kunth

Cited by 61 publications

References 18 publications

Chemistry and evolution of the Piperaceae

Chemistry and evolution of the Piperaceae

Synthesis and NMR Structure Determination of New Linear Geranylphenols by Direct Geranylation of Activated Phenols

Molluscicidal and ovicidal activities of plant extracts of the Piperaceae on Biomphalaria glabrata (Say, 1818)

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