Occurrence, biological activities and 13C NMR data of amides from Piper (Piperaceae)

Abstract

Recebido em 30/3/12; aceito em 24/7/12; publicado na web em 26/10/12 This manuscript describes an update review with up to 285 references concerning the occurrence of amides from a variety of species of the genus Piper (Piperaceae). Besides addressing occurrence, this review also describes the biological activities attributed to extracts and pure compounds, a compiled 13 C NMR data set, the main correlations between structural and NMR spectroscopic data of these compounds, and employment of hyphened techniques such as LC-MS, GC-MS and NMR for analysis of amides from biological samples and crude Piper extracts. Keywords: Piper;13 C NMR compilation; amides. INTRODUCTIONPiperaceae is one of the largest families among the basal Angiosperms, with approximately 3,000 species described to date. 1The family is currently divided into five genera: Macropiper, Zippelia, Piper, Peperomia and Manekia, 2 consisting of a wide variety of species found commonly around the world. Piper, Peperomia and Manekia occur in Brazil, mainly in the Amazonian and Atlantic forests. 3 Piper is the largest genus of this family, including more than 1,000 species, and can also be considered the largest genus of the basal angiosperms. 4 Amides are the major constituents of several species of Piper. Currently, they can be considered alkaloids in accordance with the modern definition by Pelletier.5 Natural amides can be classified as open-chain alkamides, aristolactams, 4,5-dioxoaporphines, ceramides, amides with pyrrolidine, piperidone and piperidine groups, cyclobutanamides and cyclohexanamides. The term piperamide is restricted to describe all compounds carrying an aromatic group and an amide group.In 1997, a review of this genus was published 6 dealing with chemical distribution and biological activities of amides. In the present review, an update with new chemical constituents of this genus is described and a compilation of 13 C NMR data and biological activities of these compounds are provided. Piper SPECIES, TRADITIONAL USES AND BIOLOGICAL ACTIVITIESDespite the large number of species of Piper, the use of these plants in folk medicine remains limited. One of the most well-known Piper Brazilian medicinal plants is P. corcovadensis, commonly found in North and Northeast regions, and popularly known as "João-brandinho". The leaves of this plant are used for the treatment of rheumatism in the form of poultice and infusions as well for flu and cough. In the Southeast region, the roots and branches of this specie are chewed to relieve toothache due to its anesthetic action on the mucous membrane. 7 In China, the use of leaves of P. futokasura is recommended in the treatment of cardiac arrhythmias and asthma. In Jamaica, stomach pains are treated with an infusion of leaves from P. aduncum and P. hispidum. Leaves from P. amalago are also employed in Mexico and Brazil for stomach pains and for the treatment of various infections. 8 Leaves and stems of P. marginatum and P. tuberculatum are used in Brazil, especially in Paraíba State (Brazil) agains...

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

“…Many derivatives of the first group were isolated from Piper species (for ref. : Parmar et al 1997;Do Nascimento et al 2012) (Table 4). Similar patterns of unsaturation suggest close biosynthetic connections with the elongated amides mentioned above, but also with those of the C 16 series.…”

“…As derivatives of the straight-chain fatty acid synthesis the acid parts differ biosynthetically from structurally similar but branched carbon chains from amides of the genera Capsicum of the Solanaceae (Curry et al 1999;Aza-González et al 2011;Kehie et al 2015) or Ipomoea and Merremia of the Convolvulaceae family (Tofern et al 1999). In Piperaceae the alkamides are only known from the genus Piper, where they are frequently accompanied by so-called piperamides, another class of amides, differing by an aromatic ring in the acid moiety (Parmar et al 1997;Do Nascimento et al 2012;Dawid et al 2012). From the various amides of the Rutaceae fatty acid derived alkamides were mostly found in the genus Zanthoxylum, but were also reported for Tetradium daniellii (Reisch et al 1985) and Pilocarpus trachylophus (Andrade-Neto et al 1996).…”

Biological Properties of Essential Oils from the Piper Species of Brazil: A Review

“…Many Piper species are biologically active and have shown antitumor [21], antimicrobial [22], antioxidant, insecticide, larvicide [5], anti-inlammatory, antinociceptive, enzyme inhibitor, trypanocidal, antiplatelet, piscicide, allelopathic, antiophidic, anti-malaria, antileishmania, ansiliotico/antidepressant, antituberculosis, antidiabetic, nematocide, herbicide, hepatoprotective, anti-Helicobacter pylori [23], amebicide [24] and diuretic [25] potential.…”

“…Chemistry studies of Piper species have led to the identiication of a variety of new chemical compounds belonging to diferent classes, including alkaloids [26], amides [27], chromenes [28], derivatives of benzoic acids [29], lignans, neolignans, propenyl phenols, terpenes, steroids, chalcones, diidrochalcones, lavones, lavanones, kavalactones, piperolides, ceramides, faty acids [5,10] and lavonoids [23,26].…”

The occurrence of phenylpropanoids in the saps of six Piper species (Piperaceae) from Brazil

“…The Piperaceae family is currently divided into five genera: Macropiper, Zippelia, Piper, Peperomia and Manekia. The Piper genus is considered the most expressive of this family, with more than 1,000 species identified (Nascimento et al 2012). The Piper species have been extensively studied and documented due to their medicinal and pesticide proprieties attributed to the presence of diverse secondary metabolites found in their tissues (Scott et al 2007).…”