Nicotiana rustica L. (Aztec tobacco) is the only Nicotiana species, except common tobacco (N. tabacum L.), which is cultivated for tabacco products. The leaves of N. rustica, however, accumulate various specialized metabolites of potential interest. Therefore, the objective of this study was to evaluate certain classes of metabolites (by HPLC and GC-MS) in the leaves, the essential oil (EO), concrete and resinoid of N. rustica. Three pentacyclic triterpenes were identified in the leaves (by HPLC): betulin (252.78 µg g-1), betulinic (182.53 µg g-1) and oleanolic  (69.44 µg g-1) acids. The dominant free phenolic acids in the leaves (by HPLC) were rosmarinic (4257.38 µg g-1) and chlorogenic (1714.40 µg g-1), and conjugated forms of vanillic (3445.71 µg g-1), sinapic (1963.11 µg g-1), and syringic (1784.96 µg g-1). The major flavonoids in the leaves were luteolin (960.44 µg g-1), apigenin (880.66 µg g-1) and hyperosid (780.72 µg g-1). The GS-MS profiling of the EO identified 19 components and the major ones were phytol (43.68 %), solanone (5.54 %), cis-5-butyl-4-methyldihydrofuran-2(3H)-one (5.23 %), dihydro-β-ionone (4.25 %), α-ionene (3.54 %),and β-damascenone (3.03 %). The major volatiles in the concrete were  isoamyl alcohol (28.82 %), oxynicotine (9.02 %), phytol (7.80 %), 4-mеthyl-1-penthanol (6.33 %), cotinine (5.55 %) and 3-metyl-3-penthanol (4.09 %). Resinoid composition was dominant by nicotine (39.75 %), phytol (11.23 %), eicosane (4.88 %), diethyl phthalate (4.19 %), dibutyl phthalate (3.48 %) and solanone (3.27 %). Concrete and resinoid showed weak antibacterial activity . These results create grounds for considering N. rustica as a source to obtain aroma or other bioproducts.

The flavonoid-rich natural products exert a wide range of pharmacological properties. This investigation aimed at obtaining extracts from tobacco cultivars and waste enriched with flavonoids and purified from nicotine and phenolic acids, and evaluating their radical scavenging potential. Extraction with a mixture of ethyl acetate-methanol (1:1, v/v) was employed resulting in 100% yield for flavonoids and 36% yield for phenolic acids. The crude extracts were purified using preparative column chromatography on silica gel. The content of flavonoids in the purified extracts varied from 8.8 ± 1.1% to 14.3 ± 1.8%. Nicotine was not detected in amounts higher than 0.3 μg mL(-1). The content of phenolic acids was lower than 1.0%. The radical scavenging potential of extracts from tobacco cultivars exhibited values from IC50 = 35.0 ± 3.1 to 64.6 ± 7.5 μg mL(-1). The extracts obtained by the proposed procedure are enriched with flavonoids with high radical scavenging potential and are purified from nicotine and phenolic acids. They can be regarded as potential biopharmaceuticals.

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New quercetin-based derivatives are synthesized in an easily accessible one-pot manner. The method is based on the reaction of quercetin with in situ formed electrophilic N-alkoxycarbonylazolium ions. The position of the newly formed C-C bond and structure were spectrally characterized by 1D, 2D 1H, 13C-NMR, IR, and MS analysis. Thus, in all cases, good regioselectivity in the C-8 position for the obtained products was demonstrated. The obtained compounds were evaluated for their DPPH and ABTS free radical scavenging activity and compared to natural compounds—quercetin and rutin.

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