Abstract

Background

Since Nicotiana tabacum (tobacco) has important significance to humans for their medicinal uses, to find antivirus activities inhibitors from tobacco, increase its medicinal value, and comprehensive utilization of its by-products, our group had investigated the chemical constituents of the stems of Y-202, a cultivar of tobacco which high resistance to tobacco mosaic virus (TMV).

Results

Four new isoindolinone-type alkaloids, nicoisoindoles A–D (14), along with four known isoindole derivatives (58) were isolated. Compounds 14 represent a new subclass of isoindolinone alkaloids with rare cyclopenta[f]isoindole-1-one frameworks. Among them, nicoisoindole C (3) possesses an unusual N-2-(5-methoxy-6-methylpyridin-2-yl) ethyl moiety, while nicoisoindole D (4) has a novel a N-(3-methyl-6-oxo-1,6-dihydropyridin-2-yl)methyl substituent. Interestingly, compounds 1, 3, and 4 showed high anti-TMV activities with inhibition rates of 43.8%, 58.8%, and 67.8% at the concentration of 20 μM, and IC50 values of 23.6, 19.5 and 15.4 μM, respectively, even more potent than that of positive control.

Conclusions

The successful isolation and structure identification of new oxocyclopenta[f]isoindole-1-ones provide materials for the screening of antivirus activities inhibitors, and contribute to the development and utilization of the waste from tobacco cultivation.

Details

Title
Antivirus isoindolinone alkaloids with rare oxocyclopenta[f]isoindole frameworks isolated from the stems of flue cured tobacco
Author
Hu, Qiu-Fen 1 ; Ma, Yue-Yu 2 ; Liu, Hua-Yin 1 ; Dai, Jia-Meng 3 ; Yang, Feng-Xian 3 ; Zhang, Jian-Duo 3 ; Wang, Jin 3 ; Li, Xue-Mei 3 ; Liu, Xin 3 ; Li, Jing 3 ; Li, Yin-Ke 1 ; Wang, Wei-Guang 2 ; Zhou, Min 2 ; Yang, Guang-Yu 3 

 State Ethnic Affairs Commission, Yunnan Minzu University, Key Laboratory of Natural Products Synthetic Biology of Ethnic Medicinal Endophytes, Kunming, People’s Republic of China (GRID:grid.413059.a) (ISNI:0000 0000 9952 9510); China Tobacco Yunnan Industrial Co., Ltd, Yunnan Key Laboratory of Tobacco Chemistry, Kunming, People’s Republic of China (GRID:grid.452261.6) (ISNI:0000 0004 0386 2036) 
 State Ethnic Affairs Commission, Yunnan Minzu University, Key Laboratory of Natural Products Synthetic Biology of Ethnic Medicinal Endophytes, Kunming, People’s Republic of China (GRID:grid.413059.a) (ISNI:0000 0000 9952 9510) 
 China Tobacco Yunnan Industrial Co., Ltd, Yunnan Key Laboratory of Tobacco Chemistry, Kunming, People’s Republic of China (GRID:grid.452261.6) (ISNI:0000 0004 0386 2036) 
Publication year
2022
Publication date
Dec 2022
Publisher
Springer Nature B.V.
e-ISSN
21965641
Source type
Scholarly Journal
Language of publication
English
ProQuest document ID
2736938255
Copyright
© The Author(s) 2022. This work is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.