Phenolic amides from the leaves of Nicotiana tabacum and their anti-tobacco mosaic virus activities

Shang, Shan‐Zhai; Yuanxing, Duan; Zhang, Xia; Pu, Jian‐Xin; Sun, Han‐Dong; Chen, Zhangyu; Ming-ming, Miao; Yang, Guangyu; Yongkuan, Chen

doi:10.1016/j.phytol.2014.06.012

Cited by 19 publications

(10 citation statements)

References 12 publications

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“…All compounds were tested for their anti-TMV activity, and 49 exhibited higher anti-TMV activity than that of the positive control (38.6% versus ningnamycin IR = 31.2%). The other compounds showed lower anti-TMV activity with inhibition rates of 15.3–26.5% …”

Section: Metabolite Classes: Structures and Functionsmentioning

confidence: 99%

“…The other compounds showed lower anti-TMV activity with inhibition rates of 15.3−26.5%. 249 A new phenolic compound (a sesquiterpene phenol), (6S)-6-(4-(hydroxymethyl)-2-methoxyphenyl)-6-methoxy-2-methylheptan-1-ol (55), was isolated from the root extracts of fluecured tobacco. It showed anti-TMV activity with inhibition rates of 16.4%, 250 in a half-leaf assay.…”

Section: Relationship Between General and Specialized Metabolism In P...mentioning

confidence: 99%

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Ecological Roles and Biological Activities of Specialized Metabolites from the GenusNicotiana

Jassbi¹,

Zare²,

Asadollahi³

et al. 2017

Chem. Rev.

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Species of Nicotiana grow naturally in different parts of the world and have long been used both medicinally and recreationally by human societies. More recently in our history, Nicotiana tabacum has attracted interest as one of the most economically important industrial crops. Nicotiana species are frequently investigated for their bioactive natural products, and the ecological role of their specialized metabolites in responses to abiotic stress or biotic stress factors like pathogens and herbivores. The interest of tobacco companies in genetic information as well as the success of a few wild tobacco species as experimental model organisms have resulted in growing knowledge about the molecular biology and ecology of these plants and functional studies of the plant's natural products. Although a large number of reviews and books on biologically active natural products already exists, mostly from N. tabacum, we focus our attention on the ecological roles and biological activity of natural products, versus products from cured and processed material, in this Review. The studied compounds include alkaloids, aromatic compounds, flavonoids, volatiles, sesquiterpenoids, diterpenes alcohols, and sugar esters from trichomes of the plants, and recently characterized acyclic hydroxygeranyllinalool diterpene glycosides (HGL-DTGs). In this Review (1800s-2017), we describe the above-mentioned classes of natural products, emphasizing their biological activities and functions as they have been determined either in bioassay-guided purification approaches or in bioassays with plants in which the expression of specific biosynthetic genes has been genetically manipulated. Additionally, a review on the history, taxonomy, ecology, and medicinal application of different Nicotiana species growing around the globe presented in this Review may be of interest for pharmacognosists, natural products, and ecological chemists.

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Section: Metabolite Classes: Structures and Functionsmentioning

confidence: 99%

Section: Relationship Between General and Specialized Metabolism In P...mentioning

confidence: 99%

Ecological Roles and Biological Activities of Specialized Metabolites from the GenusNicotiana

Jassbi¹,

Zare²,

Asadollahi³

et al. 2017

Chem. Rev.

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“…Several natural products extracted from N. tabacum exhibited anti-TMV activity, such as flavonoids from the roots and stems of Yunyan-202[6], biphenyls from the leaves of Honghuadajinyuan [7], sesquiterpenes and benzolactones from the leaves of Yunyan-201[8]. Here, we found that α(β)-CBD from Yunyan 100 leaves exhibited higher protection effects than the curative and inactive activities in N. tabacum L. cv.…”

Section: Discussionmentioning

confidence: 85%

“…Tobacco mosaic virus (TMV) is the most ancient virus that causes massive economic losses to tobacco, pepper, cucumber and ornamental crops globally. Several findings suggested that acetone ethanol extracts from N. tabacum leaves have antiviral activity against TMV[5–8], but the antiviral effects of their specialized metabolites have not been systematically studied yet, especially the underlying mechanism is still unexplored.…”

Section: Introductionmentioning

confidence: 99%

Extraction, purification and anti-TMV effects of α (β)-2,7,11-cembratriene-4,6-diol from tobacco leaves

Feng

Jia

Guan

et al. 2021

Preprint

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Background Acetone ethanol extracts from tobacco leaves have antiviral activity against TMV, but the antiviral effects of their specialized metabolites have not been systematically studied yet, especially the underlying mechanism is still unexplored. Results The tobacco cembranoids α(β)-2,7,11-cembratriene-4,6-diol (α(β)-CBD) were extracted and purified with an effective and green protocol including innovatively added 5% phosphoric acid for elution, one time silica gel chromatographic column separation and impurity removal and further HPLC purification. The results of antiviral activities against tobacco mosaic virus (TMV) with the local lesion counting method showed that α(β)-CBD have in vivo higher protective effects of 73.2% and 71.6%, at 75.0 μM, respectively, than control agent Ningnanmycin (53.1%). Notably, The results of ELISA and and TMV-GFP fluorescent optical imaging assay indicated a obviously reduced viral protein and weaker GFP fluorescence signal and smaller infection area, which confirmed their anti-TMV activities at protein level. Furthermore, the enhanced production of SA and JA and the significantly increased transcription of of JA signaling pathway (COI1 and PDF1.2) and SA signaling pathway genes (PR1, NPR1 and EDS1) in treated plants further conformed that exogenously applied α(β)-CBD can effectively elicit the tobacco plant immunity against TMV. Conclusions The α(β)-CBD mainly stimulates disease resistance of tobacco plants to resist TMV and it can be used as bioagents to control TMV in the future.

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“…In addition, N. tabacum is also used as insecticides, anesthetics, diaphoretics, sedatives, and emetic agents in Chinese folklore medicines because of its useful chemical compounds (Kuang and Lu, 2005;Rodgman and Perfetti, 2008). Previous phytochemical studies of tobacco have shown the presence of sesquiterpenes Yang et al, 2013), alkaloids (Braumann et al, 1990;Wei et al, 2005), lignans Gao et al, 2012a), flavonoids (Chen et al, , 2012bYe et al, 2012), phenylpropanoids (Leng et al, 2014;Tan et al, 2011), chromanones (Mou et al, 2012;Yang et al, 2014), Biphenyls (Shang et al, 2014a), phenolic amides (Shang et al, 2014b), isocoumarins (Shang et al, 2015), and the homologous. However, the previous reports on occurance of isoflavones in the Solanaceae family are still rather unusual (Arthan et al, 2002;Chen et al, 2012b;Sini and Devi., 2004;Ye et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

Isoflavones from the leaves of Nicotiana tabacum and their anti-tobacco mosaic virus activities

Shen

Liu

et al. 2015

Phytochemistry Letters

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Phenolic amides from the leaves of Nicotiana tabacum and their anti-tobacco mosaic virus activities

Cited by 19 publications

References 12 publications

Ecological Roles and Biological Activities of Specialized Metabolites from the GenusNicotiana

Ecological Roles and Biological Activities of Specialized Metabolites from the GenusNicotiana

Extraction, purification and anti-TMV effects of α (β)-2,7,11-cembratriene-4,6-diol from tobacco leaves

Isoflavones from the leaves of Nicotiana tabacum and their anti-tobacco mosaic virus activities

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