Structure Elucidation and Quantitation of 11 N'-n-Acylnornicotines in Cherry-Red Tobacco

Eleven consecutive N'-n-acylnornicotines from cherry-red tobacco were structurally elucidated and quantitively analyzed using chromatography and mass spectrometry. All of these N'-n-acylnornicotines are first reported in cherry-red tobacco, whereas N'-propionylnornicotine, N'-n-valerylnornicotine, N'-n-nonanoylnornicotine and N'-n-undecanoylnornicotine are first reported in natural products. The concentration distribution of the identified N'-n-acylnornicotines was studied and it was found that N'-n-octanoylnornicotine and N'-n-hexanoylnornicotine showed the highest concentration, accounting for 94% of the detected N'-n-acylnornicotines. The cherry-red color density of the related tobacco leaves was found to be positively correlated with the concentration of the N'-n-acylnornicotines, whereas the ultraviolet-visible spectra of the N'-n-acylnornicotines showed no absorption larger than 300 nm, indicating the discovered compounds are not responsible for the cherry-red color appearance.