Natural stilbenoids: distribution in the plant kingdom and chemotaxonomic interest in Vitaceae

Abstract

Stilbenoids, a family of polyphenols known for the complexity of their structure and for their diverse biological activities, occur with a limited but heterogeneous distribution in the plant kingdom. The most prominent stilbene containing plant family, the Vitaceae, represented by the famous wine producing grape vines Vitis vinifera L., is one of the richest sources of novel stilbenes currently known, together with other families, such as Dipterocarpaceae, Gnetaceae and Fabaceae. This review focuses on the distribution of stilbenes and 2-arylbenzofuran derivatives in the plant kingdom, the chemical structure of stilbenes in the Vitaceae family and their taxonomic implication.

Regulation of stilbene biosynthesis in plants

“…Current literature shows that stilbenes, stilbene hydrids, and 2-arylbenzofuran derivatives are produced by a limited heterogeneous group of plant species from about 50 plant families including dicotyledons, monocotyledons, conifers, liverworts, and ferns (Shen et al 2009;Riviere et al 2012). There were also studies reporting on stilbene (t-resveratrol, resveratrodehydes, and some other stilbenoids) detection and identification in plant endophytic fungi (Alternaria sp.…”

“…Multiple investigations reported on stilbene identification and stilbene structural analysis in various plant species (Shen et al 2009;Riviere et al 2012), while there were a considerably lower number of studies analyzing both stilbene contents and repertoire in plants. Table 1 compiles most detailed studies that report on both stilbene content and repertoire in different plant families.…”

“…Stilbenoids, including basic stilbenes, bibenzyls, or dihydrostilbenes, bis(bibenzyls), phenantrenes, 9,10-dihydrophenanthrenes, and related compounds, are the organic phenolic compounds derived from the general phenylpropanoid pathway and are structurally characterized by the presence of a 1,2-diphenylethylene nucleus (Riviere et al 2012). Biosynthesis of stilbenes and other phenylpropanoids begins from the synthesis of trans-cynnamic acid or its derivative p-coumaric acid from the aromatic amino acids phenylalanine or tyrosine, respectively (Fig.…”

“…1 and 2). The trans isomer (T) or (E) is the most common configuration of plant-derived monomeric stilbenes (Table 1; Riviere et al 2012). Oligomeric stilbenes are produced by oxidative coupling between homogenous or heterogeneous monomeric stilbenes and are characterized by complex structural configurations (Shen et al 2009).…”

In vitro antileishmanial activity of trans-stilbene and terphenyl compounds

“…In this context, in the last years several natural compounds and their synthetic analogues have been tested against Leishmania, and many of them have demonstrated potential as leishmanicidal agents (Changtam et al, 2010;Tipparaju et al, 2008;Marin et al, 2009;Mishra et al 2009a,b;Hussain et al, 2014;Singh et al, 2014). Stilbenes-based compounds are widely represented in nature (Shen et al, 2009;Riviere et al, 2012) and have become of particular interest to chemists and biologists because of their wide range of biological effects including chemopreventive, antitumor, antioxidant, antimicrobial, anti-inflammatory and antihistaminic activities (Hart, 1981;Fremont, 2000;Young and Chaplin, 2004). Recently, several natural and synthetic stilbenoids have been studied for their leishmanicidal properties (del Rey et al, 1999;del Olmo et al, 2001;Getti et al, 2006;Fuchino et al, 2013;de Almeida Machado et al, 2015) and some of them, including resveratrol (trans-3,4 0 ,5-trihydroxystilbene, Fig.…”