Alkaloids from cigar

IF 1.3 3区医学 Q3 CHEMISTRY, APPLIED

Journal of Asian Natural Products Research Pub Date : 2025-03-19 DOI:10.1080/10286020.2025.2475477

Qing-Yang Wu , Guang-Hai Zhang , Feng Wei , Yin-Ke Li , Guang-Hui Kong , Xiang-Hai Cai

引用次数: 0

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.

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雪茄里的生物碱。

对雪茄烟草进行植物化学研究，鉴定出16种生物碱，包括两种未描述的尼古丁二聚体类似物cigatobines A-B(1-2)，以及新的天然产物pyridylnicotine(3)，顺式-5'-（2-氧丙基）-nicotine(8) 4-（甲酰胺）-1-（3-吡啶基）-1-丁酮（14），5,6-二氢吡啶-2(1H)-one（15）。二聚体烟碱及其衍生物的形成涉及Minisci反应和亲核加成反应等化学机制。与α7-nAChR受体分子对接发现5种活性化合物，结合亲和力评分分别为-8.077(2)、-7.805（尼古丁）、-7.804(8)、-5.788(1)、-5.707(3)、-7.452（依比替丁）。这项研究揭示了雪茄和烟草中生物碱的差异。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Asian Natural Products Research 医学-药学

CiteScore

3.20

自引率

5.90%

发文量

审稿时长

2.3 months

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.