Ecological Roles and Biological Activities of Specialized Metabolites from the GenusNicotiana

Abstract

Species of Nicotiana grow naturally in different parts of the world and have long been used both medicinally and recreationally by human societies. More recently in our history, Nicotiana tabacum has attracted interest as one of the most economically important industrial crops. Nicotiana species are frequently investigated for their bioactive natural products, and the ecological role of their specialized metabolites in responses to abiotic stress or biotic stress factors like pathogens and herbivores. The interest of tobacco companies in genetic information as well as the success of a few wild tobacco species as experimental model organisms have resulted in growing knowledge about the molecular biology and ecology of these plants and functional studies of the plant's natural products. Although a large number of reviews and books on biologically active natural products already exists, mostly from N. tabacum, we focus our attention on the ecological roles and biological activity of natural products, versus products from cured and processed material, in this Review. The studied compounds include alkaloids, aromatic compounds, flavonoids, volatiles, sesquiterpenoids, diterpenes alcohols, and sugar esters from trichomes of the plants, and recently characterized acyclic hydroxygeranyllinalool diterpene glycosides (HGL-DTGs). In this Review (1800s-2017), we describe the above-mentioned classes of natural products, emphasizing their biological activities and functions as they have been determined either in bioassay-guided purification approaches or in bioassays with plants in which the expression of specific biosynthetic genes has been genetically manipulated. Additionally, a review on the history, taxonomy, ecology, and medicinal application of different Nicotiana species growing around the globe presented in this Review may be of interest for pharmacognosists, natural products, and ecological chemists.

Glucosylation of the phytoalexin N‐feruloyl tyramine modulates the levels of pathogen‐responsive metabolites in Nicotiana benthamiana

“…Nicotiana species are indigenous plants of America, but at this time they occur naturally in large parts of the world (Jassbi et al, 2017). The genus Nicotiana also includes some important crop and medicinal plants that produce natural products with psychoactive, medicinal, and toxic activities (Goodin et al, 2008).…”

“…The genus Nicotiana also includes some important crop and medicinal plants that produce natural products with psychoactive, medicinal, and toxic activities (Goodin et al, 2008). These specialized metabolites serve different ecological roles for the plants including protection against biotic and abiotic stresses such as pathogens, herbivores, drought and salinity as well as promoting outcrossing and dispersal (Jassbi et al, 2017). As Nicotiana species are a rich source for bioactive plant secondary metabolites their production and biological activities have been extensively studied including pyridine alkaloids, isoprenoids, aromatic compounds, and volatiles (Nugroho and Verpoorte, 2002).…”

“…The wild tobacco N. benthamiana is heavily utilized as the host for agroinfiltration experiments for the functional analysis of foreign and endogenous genes (Goodin et al, 2008). It is also an important model in intraspecies and interplant interaction research and plant molecular biology (Jassbi et al, 2017). The wild coyote tobacco, N. attenuata, is a model organism in molecular chemical ecology.…”

Terpenoids in the Essential Oil and Concentrated Aromatic Products Obtained from Nicotiana glutinosa L. Leaves

“…Sclareol was highly effective against a set of medicinally important yeasts; Candida albicans AТCC 10231, C. glabrata ATCC 90030, C. parapsilosis clinical isolate, and C. tropicalis NBIMCC 23, while being less effective against the studied Gram-positive and Gram-negative bacteria. Data from the study on N. glutinosa aromatic products composition may be of interest to the aroma industries for their possible use in perfumery and cosmetics.Molecules 2020, 25, 30 2 of 16 N. glutinosa is native to Northern and Central Peru and Southern Ecuador, where it has adapted well to semi-arid areas, rocky slopes and ditch banks [1,5]. Plants are more fragile and with tender stem than common tobacco (N. tabacum), rarely branching [6].…”

Quantitative analysis of cembranoids in tobacco leaf by using heart‐cutting two‐dimensional liquid chromatography

“…Sea coral reef), where they are thought to play an important role in biological metabolism . By activation of pancreatic beta‐cell regeneration, cembranoids were thought to be useful for the development of a new class of antidiabetic agents .Therefore synthesis and analysis of the cembranoids were investigated extensively .…”