Tropane alkaloids and calystegines as chemotaxonomic markers in the Solanaceae

Abstract

This study assessed the occurrence and distribution of tropane alkaloids and calystegines in genera of the family Solanaceae to identify patterns of distribution and make evolutionary inferences. A database of tropane alkaloids and calystegines occurrences was constructed from the results of a search of scientific websites and a hand search of periodicals. The terms "Solanaceae", "tropane alkaloids", and "calystegines" were used as index terms for a full-text article search unrestricted by date of publications. The number of occurrence and chemical diversity indices were calculated and cluster analysis and principal components analysis were performed. Overall, 996 occurrences were reported, 879 of tropane alkaloids (88.3%) and 117 of calystegines (11.7%). The calystegines were significantly more relevant than tropane alkaloids for characterization of distinct groups of genera on both analyses performed here. This corroborates the trend toward a chemical dichotomy observed on database analysis and somewhat reinforces the correlation between geographic distribution and occurrence of secondary metabolites, as the presence of calystegines alone (without tropane alkaloids) was only reported in genera that have South America as their center of diversity.

A revision of the Old World Black Nightshades (Morelloid clade of Solanum L., Solanaceae)

“…The European members of the group are often confused with the deadly nightshade Atropa bella-donna L., whose berries are similarly black and shiny, but contain highly toxic tropane alkaloids such as atropine and scopolamine (Parr et al 1990; Ashtiana and Sefidkonb 2011). No species of Solanum has been shown to contain tropane alkaloids such as atropine or scopolamine (Tétényi 1987; Pigatto et al 2015), but members of Solanum , including the black nightshades, do contain the nortropane alkaloids known as calystegines (Dräger et al 1994; Pigatto et al 2015). In Solanaceae, these compounds are synthesised along the same pathway as the tropanes, but are not as toxic when tested on laboratory rats (Stegelmeier et al 2008); the finding that they occur in many commonly eaten foods suggests their activity differs from that of the tropanes such as atropine, scopolamine and nicotine (Asano et al 1997; Welch et al 2012).…”

Anticholinergic syndrome induced by toxic plants

“…They typically have anticholinergic and anesthetic properties. [15] Atropine, hyoscyamine and scopolamine are the most important and extensively studied members of tropane alkaloids. All these substances are found in high concentrations in both Datura Stramonium and AtropaBelladona.…”

The genusCapsicum: a phytochemical review of bioactive secondary metabolites

“…44 The absence of studies focused on the chemosystematics of the Capsicum genus is mainly related to the large chemical variability induced by the intraspecic and interspecic hybridization which occurs, not only by natural means as a consequence of the evolution process, but also by the human intervention that has been carried out since the marine exploration periods. 4,44,[98][99][100] In addition to the process of hybridization, the variability in CAPS prole can be attributed not only to the hybridization process but also to other factors, which can be either endogenous (species genetic characters and ripening stage) and exogenous (such as seasoning, climatic conditions and soil fertility). 42,48,77,85 In addition, the mechanisms of CAPS regulation is not consolidated, it had been reported that their biosynthesis and catabolism undergoes very sensitive mechanisms.…”

“…The chemosystematic study of botanic species is a promising tool in the discovery of biodiversity, although few researches focus on this topic even when dealing with botanical families with great economical interest, such as the Solanaceae family. 99,100,106,195 From the 19 th century to the year of 2008the systematics for Solanaceae were rewritten eight times, considering only those with good acceptance among the scientic community. Among these systematic proposals only 2 of them included chemical characters, the rst in 1987 and the second in 2001.…”

“…Among these systematic proposals only 2 of them included chemical characters, the rst in 1987 and the second in 2001. 99 Pigatto et al 99 (2015) performed a chemosystematic study of the Solanaceae family, to determine whether each species can synthesize two distinct classes of metabolites, tropane alkaloids and calysteliges. In this study it was highlighted that the Capsicum genus, four of the genera among the 29 studied, were unable to synthesize tropane alkaloids, presenting only two specic structure types of calysteliges (tetrahydroxynortropanes and pentahydroxynortropanes) and nicotinoids.…”