Two New Coumarins from the Roots and Stems of Nicotiana tabacum and their Bioactivity

Zhu, Lijun; Luo, Dian; Lv, Na; Li, Yin-ke; Mi, Qi-Li; Wang, Jin; Kong, Wei-Song; Gao, Qian; Li, Gan‐Peng; Yang, Guangyu; Hu, Qiu‐Fen; Guan, Ying; Ye, Yanqing

doi:10.1007/s10600-020-03157-1

Cited by 11 publications

(2 citation statements)

References 24 publications

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“…In addition, tobacco also has important significance to humans for their ornamental values and medicinal uses [2]. In recent years, many bioactive naturally small molecule metabolites have been reported from this genus, including diterpenoids [3], sesquiterpenoids [4,5], flavonoids [6,7], coumarins [8,9], furans [10,11], alkaloids [12,13], sterols [6], and the like. The biosynthesis and pharmacological properties of some metabolites also have been widely elucidated, such as pyridine alkaloids, including the eponymous nicotine [14], isoprenoids [15], aromatic compounds [16], and polyphenols [17].…”

Section: Introductionmentioning

confidence: 99%

Antivirus isoindolinone alkaloids with rare oxocyclopenta[f]isoindole frameworks isolated from the stems of flue cured tobacco

Liu

et al. 2022

Chem. Biol. Technol. Agric.

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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. Graphical Abstract

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Section: Introductionmentioning

confidence: 99%

Antivirus isoindolinone alkaloids with rare oxocyclopenta[f]isoindole frameworks isolated from the stems of flue cured tobacco

Liu

et al. 2022

Chem. Biol. Technol. Agric.

Self Cite

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“…Additionally, tobacco also has important signi cance to humans for their ornamental values and medicinal uses [2]. In recent years, many bioactive naturally small molecule metabolites have been reported from this genus, including diterpenoids [3], sesquiterpenoids [4,5], avonoids [6,7], coumarins [8,9], furans [10,11], alkaloids [12,13], sterols [6], and the like. The biosynthesis and pharmacological properties of some metabolites also have been widely elucidated, such as pyridine alkaloids, including the eponymous nicotine [14], isoprenoids [15], aromatic compounds [16], and polyphenols [17].…”

Section: Introductionmentioning

confidence: 99%

Anti-Virus Isoindolinone alkaloids with rare oxocyclopenta[f]isoindole frameworks isolated from the stems of flue cured tobacco

Liu

et al. 2022

Preprint

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Background The large scale tobacco planting in Yunnan produces a large amount of waste, including stems, roots, low grade and defective tobacco leaves. Therefore, the multipurpose utilization of the by-product of tobacco is an interesting topic. In order to increase medicinal value of tobacco and the comprehensive utilization of its by-products, our group had investigated the chemical constituents of the stems of Y-202, a cultivar of tobacco with high resistance to tobacco mosaic virus (TMV), which originated from K326 by ethylmethane sulfonate (EMS) mutagenesis. Results As a result, four new isoindolinone-type small molecule alkaloids named nicoisoindoles A–D (1–4), along with four known isoindole derivatives (5–8) were isolated. Nicoisoindoles A–D 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. In order to study whether the oxocyclopenta[f]isoindole-1-ones have more broad antiviral activities, compounds 1–4 were also tested for their anti-rotavirus activities, and they exhibited potential anti-rotavirus activities with therapeutic index (TI) valves in the range of 13.0-18.5. Conclusions The successful isolation and structure identification of oxocyclopenta[f]isoindole-1-ones provide materials for the screening of anti-virus activities inhibitors, and also contribute to the development and utilization of the waste from tobacco cultivation.

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Anti-Tobacco Mosaic Virus Chromone Derivatives from the Stems of Nicotiana tabacum

et al. 2021

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Two New Coumarins from the Roots and Stems of Nicotiana tabacum and their Bioactivity

Cited by 11 publications

References 24 publications

Antivirus isoindolinone alkaloids with rare oxocyclopenta[f]isoindole frameworks isolated from the stems of flue cured tobacco

Antivirus isoindolinone alkaloids with rare oxocyclopenta[f]isoindole frameworks isolated from the stems of flue cured tobacco

Anti-Virus Isoindolinone alkaloids with rare oxocyclopenta[f]isoindole frameworks isolated from the stems of flue cured tobacco

Anti-Tobacco Mosaic Virus Chromone Derivatives from the Stems of Nicotiana tabacum

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