Alkaloids from cigar

Phytochemical investigation on cigar tobacco led to identification of 16 alkaloids including two undescribed nicotine dimeric analogs, cigatobines A-B (<b>1-2</b>), as well as new natural products pyridylnicotine (<b>3</b>), cis-5'-(2-oxopropyl)-nicotine (<b>8</b>) 4-(formamido)-1-(3-pyridyl)-1-butanone (<b>14</b>), 5,6-dihydropyridin-2(1H)-one (<b>15</b>). Some chemical mechanisms including Minisci reaction and nucleophilic addition reaction were involved in formation of dimeric nicotine and its derivatives. Molecular docking on this type alkaloids with the α7-nAChR receptor disclosed five active compounds with binding affinity scores of -8.077 of <b>2</b>, -7.805 of nicotine, -7.804 of <b>8</b>, -5.788 of <b>1</b>, -5.707 of <b>3</b>, -7.452 of epibatidine. This study disclosed the difference in alkaloids between cigar and tobacco.