Steroidal Glycosides from Nicotiana Tabacum L. Seeds and their Biological Activity

Shvets, S. A.; Gutsu, O. N.; Кинтя, П. К.

doi:10.1007/978-1-4613-0413-5_22

Cited by 7 publications

(5 citation statements)

References 6 publications

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“…The plants from steroidal glycoside-treated seeds were exposed to viral infection by TMV, tomato bronzetop virus (TBV), and potato Y-virus (TYV). The treated plants were less infected in comparison to the control plants . The immunity of the plants grown from steroidal glycoside treated seeds was between 3 and 20 times greater than that of nontreated plants to infection by the above-mentioned viral disease expressed as viability percentage.…”

Section: Metabolite Classes: Structures and Functionsmentioning

confidence: 99%

“…The immunity of the plants grown from steroidal glycoside treated seeds was between 3 and 20 times greater than that of nontreated plants to infection by the above-mentioned viral disease expressed as viability percentage. Therefore, the compounds showed both phytostimulating and immunoprotective activity . Cholesterol ( 419 ), campesterol ( 420 ), stigmasterol ( 421 ), and β-sitosterol ( 422 ) were identified by GC in the stem and leaf tissues of N.…”

Section: Metabolite Classes: Structures and Functionsmentioning

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: Metabolite Classes: Structures and Functionsmentioning

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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show abstract

“…By comparing the NMR data with the reported values, the known compounds 11-18, 20, 21, and 27 were firstly identified as trigofoenoside B (11) [18], trigoneoside Xa (12) [19], trigoneoside Xb (13) [19], nicotianoside F (14) [20], tuberoside A (15) [11], tuberoside B (16) [21], shatavarin I (18) [22], protoneodioscin (20) [23], pseudoprotodioscin (21) [24], tuberoside L (27) [13], respectively. The structure of 19 had been already registered in CAS with the numbers of 1493828-40-2 and also reported as 3 26-triol in the literature [25], but no full NMR data are available for them.…”

Section: Resultsmentioning

confidence: 99%

“…20 and C-22 positions. The characteristic carbon signals of δ 103.6 and 152.4 indicate the existence of the ∆ 20(22) -ene substructures in the molecule.…”

mentioning

confidence: 98%

Steroidal Glycosides from Allium tuberosum Seeds and Their Roles in Promoting Testosterone Production of Rat Leydig Cells

Zhang

Wei

2020

Molecules

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A systematic phytochemical study on the components in the seeds of Allium tuberosum was performed, leading to the isolation of 27 steroidal glycosides (SGs 1–27). The structures of SGs were identified mainly by nuclear magnetic resonance and mass spectrometries as well as the necessary chemical evidence. In the SGs, 1–10 and 22–26 are new steroidal saponin analogues. An in vitro bioassay indicates that 1, 2, 7, 8, 10, 13–15, 20, 23, and 26 display promotional roles in testosterone production of rat Leydig cells with the EC50 values of 1.0 to 4.5 μM, respectively.

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“…Among them, spirostanes share similarities in their physiological activity with BRs and have the potential to act as natural plant growth promoters. Steroidal glycosides of the spirostane series extracted from Nicotiana tabacum L. seeds presented growth-stimulating activities [ 10 ]. In general, low doses of exogenous auxin can promote plant growth.…”

Section: Introductionmentioning

confidence: 99%

Metabolomics Mechanism and Lignin Response to Laxogenin C, a Natural Regulator of Plants Growth

Deng

Wang

Zhang

et al. 2022

IJMS

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Laxogenin C (LGC) is a natural spirostanol deriving from plant hormone which has shown growing regulation similar to those of brassinosteroids. In the present study, LGC showed a promoting effect on tomato seed germination and seedling growth in a dose-dependent manner. We applied LC-MS/MS to investigate metabolome variations in the tomato treated with LGC, which revealed 10 differential metabolites (DMs) related to KEGG metabolites, associated with low and high doses of LGC. Enrichment and pathway mapping based on the KEGG database indicated that LGC regulated expressions of 2-hydroxycinnamic acid and l-phenylalanine to interfere with phenylalanine metabolism and phenylpropanoids biosynthesis. The two pathways are closely related to plant growth and lignin formation. In our further phenotypic verification, LGC was confirmed to affect seedling lignification and related phenylpropanoids, trans-ferulic acid and l-phenylalanine levels. These findings provided a metabolomic aspect on the plant hormone derivates and revealed the affected metabolites. Elucidating their regulation mechanisms can contribute to the development of sustainable agriculture. Further studies on agrichemical development would provide eco-friendly and efficient regulators for plant growth control and quality improvement.

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Steroidal Glycosides from Nicotiana Tabacum L. Seeds and their Biological Activity

Cited by 7 publications

References 6 publications

Ecological Roles and Biological Activities of Specialized Metabolites from the GenusNicotiana

Ecological Roles and Biological Activities of Specialized Metabolites from the GenusNicotiana

Steroidal Glycosides from Allium tuberosum Seeds and Their Roles in Promoting Testosterone Production of Rat Leydig Cells

Metabolomics Mechanism and Lignin Response to Laxogenin C, a Natural Regulator of Plants Growth

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