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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 (1–4), along with four known isoindole derivatives (5–8) were isolated. Compounds 1–4 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.
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Details
1 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)
2 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)
3 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)