A New Coumarin from Roots and Stems of Flue-Cured Tobacco and its Anti-Tobacco Mosaic Virus Activity

Liu, Wei; Wu, Jia; Wang, Sujuan; Kong, Wei-Song; Yunhua, Qin; Yang, Guang–Yu; Yongkuan, Chen

doi:10.14233/ajchem.2014.15807

Cited by 5 publications

(2 citation statements)

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“…A new coumarin, 6-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-2 H -chromen-2-one ( 72 ), was isolated from the roots and stem extracts of flue-cured tobacco. It exhibited inhibition rates of 23.6% against TMV …”

Section: Metabolite Classes: Structures and Functionsmentioning

confidence: 99%

“…It exhibited inhibition rates of 23.6% against TMV. 254 Three novel isoprenylated and alkylated isocuomarins, tabaisocoumarins A−C (73−75) and 5-hydroxy-7-methoxy-(1hydroxyethyl) phthalide ( 76), angelicoin A (77), and cichorin A (78) were isolated from roots and stems of N. tabacum. Compounds 73, 74−78 inhibited TMV activity in the range of 18.7−28.5%, while 74 showed the highest activity, 33.8%, even more than that measured for the positive control, ningnamaycin, when they were applied at 20 μM in a half-leaf bioassay.…”

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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Progress in the Chemistry of Naturally Occurring Coumarins

Sarker

Nahar

2017

Progress in the Chemistry of Organic Natural Products

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Coumarins are the largest group of 1-benzopyran derivatives found in plants. The initial member of this group of compounds, coumarin (2H-1-benzopyran-2-one), a fragrant colorless compound, was first isolated from the Tonka bean (Dipteryx odorata, family Fabaceae) in 1820. The name coumarin comes from a French term for the tonka bean, coumarou. Since the discovery of coumarin, several of its derivatives, with umbelliferone (7-hydroxycoumarin) being the most common one, have been reported from various natural sources. The families Apiaceae, Asteraceae, and Rutaceae are the three major plant sources of coumarins.Generally, these plant secondary metabolites may be classified into simple, simple prenylated, simple geranylated, furano, pyrano, sesquiterpenyl and oligomeric coumarins. Using this standard classification, this chapter aims to present an account on the advances of the chemistry of naturally occurring coumarins, as reported in the literature during the period 2013-2015.In Sect. 1, the coumarins are introduced and their generic biosynthetic route discussed briefly. In Sect. 2, the largest of the three sections, various classes of natural coumarins are detailed, with their relevant structures and the citation of appropriate references. In a concluding section, it is highlighted that during the last 3 years, more than 400 coumarins have been reported in the literature. Many of these coumarins have been re-isolations of known compounds from known or new sources, most often associated with various biological activities. However, a substantial number of coumarins bearing new skeletons, especially dimers, prenylated furanocoumarins, sesquiterpenyl, and some unusual coumarins were also reported during the period of 2013-2015.Coumarin chemistry remains one of the major interest areas of phytochemists, especially because of their structural diversity and medicinal properties, along with the wide-ranging bioactivities of these compounds, inclusive of analgesic, anticoagulant anti-HIV, anti-inflammatory, antimicrobial, antineoplastic, antioxidant, and immunomodulatory effects. Despite significant advancements in the extraction, isolation, structure elucidation and bioactivity testing of naturally occurring coumarins, only a marginal advancement has been observed recently in relation to the study of their biosynthesis.

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Design, synthesis and antifungal activities of novel pyrrole- and pyrazole-substituted coumarin derivatives

et al. 2019

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A New Coumarin from Roots and Stems of Flue-Cured Tobacco and its Anti-Tobacco Mosaic Virus Activity

Cited by 5 publications

References 0 publications

Ecological Roles and Biological Activities of Specialized Metabolites from the GenusNicotiana

Ecological Roles and Biological Activities of Specialized Metabolites from the GenusNicotiana

Progress in the Chemistry of Naturally Occurring Coumarins

Design, synthesis and antifungal activities of novel pyrrole- and pyrazole-substituted coumarin derivatives

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