{"title":"Alkaloids from cigar.","authors":"Qing-Yang Wu, Guang-Hai Zhang, Feng Wei, Yin-Ke Li, Guang-Hui Kong, Xiang-Hai Cai","doi":"10.1080/10286020.2025.2475477","DOIUrl":null,"url":null,"abstract":"<p><p>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.</p>","PeriodicalId":15180,"journal":{"name":"Journal of Asian Natural Products Research","volume":" ","pages":"1-9"},"PeriodicalIF":1.3000,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Asian Natural Products Research","FirstCategoryId":"3","ListUrlMain":"https://doi.org/10.1080/10286020.2025.2475477","RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
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Abstract
Phytochemical investigation on cigar tobacco led to identification of 16 alkaloids including two undescribed nicotine dimeric analogs, cigatobines A-B (1-2), as well as new natural products pyridylnicotine (3), cis-5'-(2-oxopropyl)-nicotine (8) 4-(formamido)-1-(3-pyridyl)-1-butanone (14), 5,6-dihydropyridin-2(1H)-one (15). 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 2, -7.805 of nicotine, -7.804 of 8, -5.788 of 1, -5.707 of 3, -7.452 of epibatidine. This study disclosed the difference in alkaloids between cigar and tobacco.
期刊介绍：
The Journal of Asian Natural Products Research (JANPR) publishes chemical and pharmaceutical studies in the English language in the field of natural product research on Asian ethnic medicine. The journal publishes work from scientists in Asian countries, e.g. China, Japan, Korea and India, including contributions from other countries concerning natural products of Asia. The journal is chemistry-orientated. Major fields covered are: isolation and structural elucidation of natural constituents (including those for non-medical uses), synthesis and transformation (including biosynthesis and biotransformation) of natural products, pharmacognosy, and allied topics. Biological evaluation of crude extracts are acceptable only as supporting data for pure isolates with well-characterized structures.
All published research articles in this journal have undergone rigorous peer review, based on initial editor screening and anonymized refereeing by at least two expert referees.
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