Spectroscopic characterization of N-isobutyl-6-(p-methoxyphenyl) 2E,4E-hexadieneamide extracted from Ottonia propinqua

Antunes, Pedro; Chierice, Gilberto Orivaldo; Constantino, Carlos J. L.; Aroca, Ricardo F.

doi:10.1016/s0924-2031(01)00132-1

Cited by 11 publications

(8 citation statements)

References 18 publications

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“…Essas plantas são popularmente utilizadas no país como diuréticas, salivantes e anestésicas, sendo muitas vezes conhecidas como "anestesia" e "falso jaborandi" (Lopes, 1989;Cunico, 2001;Cunico et al, 2004;Agra et al, 2007 and. A espécie Ottonia anisum é uma fonte promissora de metabolitos secundários dentre os quais as amidas são de grande interesse medicinal (Antunes et al, 2001). …”

Section: Introductionunclassified

Caracterização de derivado arilbutanoídico em folhas e raízes de Ottonia anisum Sprengel

Marques¹,

Velozo²,

Guimarães

et al. 2008

Rev. bras. farmacogn.

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RESUMO:A família Piperaceae é formada por 5 gêneros, Piper, Peperomia, Pothomorphe, Ottonia e Sarcorhachis, com cerca de 2000 espécies de ampla distribuição nas regiões tropicais e subtropicais do mundo. Das 23 espécies descritas para o gênero Ottonia, a maioria é nativa do Brasil. Essas plantas são popularmente utilizadas no país como diuréticas, salivantes e anestésicas. O estudo químico dos extratos apolares de folhas e de raízes de Ottonia anisum Sprengel levou ao isolamento de um componente majoritário identifi cado como o derivado arilbutanoídico: 1-butil-3,4-metilenodioxibeneno.Unitermos: Piperaceae, Ottonia anisum, 1-butil-3,4-metilenodioxibeneno.ABSTRACT: "Characterization of an arylbutanoic derivative from leaves and roots of Ottonia anisum Sprengel". The family Piperaceae encompasses 5 genera, Piper, Peperomia, Pothomorphe, Ottonia and Sarcorhachis, and approximately 2,000 species widely distributed in the tropical and subtropical regions of the world. Most of the Ottonia species are native to Brazil and they are used in folk medicine as diuretic, salivating, and anaesthetic. Chemical studies of non-polar fractions from leaves and roots of Ottonia anisum Sprengel lead to the isolation of an arylbutanoic metabolite, the 1-butyl-3,4-methylenedioxybezene.

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Section: Introductionunclassified

Caracterização de derivado arilbutanoídico em folhas e raízes de Ottonia anisum Sprengel

Marques¹,

Velozo²,

Guimarães

et al. 2008

Rev. bras. farmacogn.

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“…Similar to established local anesthetics, piperovatine produces tongue-numbing because it is a potent stimulator of neuronal intracellular calcium increase, similar in duration and character to other voltage-gated sodium channel agonists. These alkamides have been isolated from Ottonia propinqua [231,232], O. frutescens [233], and Matricaria pubescens [234]. The predominant mode of local anesthetic action is the blockage Chapter 3 Natural and Synthetic Alkamides of voltage-gated sodium channel which increases sodium conductance across the neuronal membrane [229].…”

Section: Piperine and Piperovatinmentioning

confidence: 99%

Natural and Synthetic Alkamides

Rios

Olivo

2014

Studies in Natural Products Chemistry

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“…129 corcovadensis. Alkamides isolated from the Ottonia genus contain 1-oxo-5-(3',4'methylenedioxyphenyl)-2E,4E-pentadien-1-yl and 1-oxo-6-(p-methoxyphenyl)-2E,4Ehexadien-1-yl residues as acidic fragments with N-isobutyl or N-3-acetoxy-isobutyl fragments as the amide residues (Antunes et al, 2001;Costa & Mors, 1981, table 6). The Piper species have been used in traditional medicine for thousands of years in China, India and Mexico, among other countries, for the treatment of several diseases and ailments.…”

Section: The Piperaceae Family Piperine and Its Analogsmentioning

confidence: 99%

Natural Alkamides: Pharmacology, Chemistry and Distribution

Rios¹

2012

Drug Discovery Research in Pharmacognosy

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Alkamides are a broad and expanding group of bioactive natural compounds found in at least 33 plant families. Despite the relatively simple molecular architecture of alkamides (fig. 1), these natural products show broad structural variability and an important range of biological activities, such as immunomodulatory, antimicrobial, antiviral, larvicidal, insecticidal, diuretic, pungent, analgesic, cannabimimetic and antioxidant activities. Additionally, alkamides are involved in the potentiation of antibiotics and the inhibition of prostaglandin biosynthesis, RNA synthesis and the arachidonic acid metabolism, among others. Many plant species containing alkamides have been used in traditional medicine by different civilizations around the world. Many of the plants containing these natural products have been used in the treatment of toothaches and sore throats (Rios-Chavez et al., 2003). These compounds are present in different organs of the plant, such as roots (Heliopsis longipes, Echinaceae purpurea, Achillea wilhelmsii, Acmella oppositifolia, Asiasarum heterotropoide, Cissampelos glaberrima, etc.), leaves and stems (Aristolochia gehrtii, Phyllanthus fraternus, Amaranthus hypochondriacus, Achyranthes ferruginea, etc.), the pericarpium (Zanthoxylum piperitum and Piper spp.), the placenta of Capsicum spp., the fruits of Piper longum, the flowers of Spilanthes acmella, the seeds of the Piper species and tubers of Lepidium meyenii. It is believed that alkamides act as plant growth regulators, promoting or inhibiting the growth and formation of roots in a dose-dependent manner and showing a positive effect in plant biomass production (Campos-Cuevas, et al., 2008). Structurally, natural alkamides commonly have an aliphatic, cyclic or aromatic amine residue, and a C8 to C18 saturated or unsaturated chain (including double or triple bonds, or both) acid, which can also be aromatic. The nature of the acid (carbon chain lengths, unsaturation level, stereochemistry, etc.) and the amine residues are characteristic of each family and genus of plants such that these characteristics serve as chemotaxonomic criteria (fig. 1). Because the nitrogen atom of alkamides is not part of a heterocyclic ring, these compounds are classified as protoalkaloids or pseudoalkaloids.

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Spectroscopic characterization of N-isobutyl-6-(p-methoxyphenyl) 2E,4E-hexadieneamide extracted from Ottonia propinqua

Cited by 11 publications

References 18 publications

Caracterização de derivado arilbutanoídico em folhas e raízes de Ottonia anisum Sprengel

Caracterização de derivado arilbutanoídico em folhas e raízes de Ottonia anisum Sprengel

Natural and Synthetic Alkamides

Natural Alkamides: Pharmacology, Chemistry and Distribution

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