Steroid glycosides of the seeds ofNicotiana tabacum. II. The structures of nicotianosides C and F

Shvets, S. A.; Kintya, P. K.; Gutsu, O. N.; Гришковец, В. И.

doi:10.1007/bf01165196

Cited by 4 publications

(5 citation statements)

References 7 publications

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“…tabacum) (Figure ). Another furastane glycoside, rusticoside G ( 418 ), 3- O -α- l -rhamnopyranosyl-(1→4)-α- l -rhamnopyranosyl-(1→4)-β- d -glucopyranoside-(25 R )-5α-furostan, 22-keto, 3β,16β,26-triol-[26- O -β- d -glucopyranoside], was isoated from seeds of N. rustica and showed contraceptive activity .…”

Section: Metabolite Classes: Structures and Functionsmentioning

confidence: 99%

“…444 Subsequently, two other spirostanes, nicotianoside C (414) and nicotianoside D (415), and furostane nicotianoside F (416) and nicotianosides G (417) steroidal glycosides have been isolated from seeds of tobacco (N. tabacum) (Figure 32). 445 Another furastane glycoside, rusticoside G ( 418 447 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.…”

Section: Chemical Reviewsmentioning

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: Chemical Reviewsmentioning

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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“…Phytochemical study of A. austroiranicum, aiming the saponin constituents of the plant, resulted in isolation and identification of steroidal saponin from flowers of the plant, using the comprehensive spectroscopic methods, its chemical structure was finally determined as (25S)-5α-Spirostan-1β,3βdiol The isolated compound is structurally related to the steroidal saponins isolated from Allium tuberosum, Allium ampeloprasum and Nicotiana tabacum, in previous studies (20)(21)(22).…”

Section: Discussionmentioning

confidence: 92%

“…In the ESIMS spectra, compound (1) showed a pseudomolecular ion peak at m/z 909.49 [M+Na] + in the positive-ion mode which together with the C-NMR data, suggested its molecular formula as C 45 H 74 O 17 (Table 1). Using the mass spectrometry (ESIMS) and NMR spectral data and comparing them with those reported in the literature (20,22), the nature of the aglycon part of the compound was determined as smillagenin, which was finally confirmed by HSQC correlations. which were suggested to be attached to C2 I and C4 I of β-D-glucopyranoside, respectively.…”

Section: Characterization Of Compound (1)mentioning

confidence: 88%

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Antileishmanial Activity of New Steroidal Saponin Isolated from the Flowers of Allium Austroiranicum

Delazar¹,

Ashrafi²,

Dinani³

2022

JABS

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Background & Objective: Plants are reservoirs of bioactive compounds, which are known to be chemically balanced, effective and least injurious as compared to synthetic medicines. The current resistance and the toxic effects of the available drugs have brought the trend to assess the antileishmanial effect of various plant extracts and their purified compound/s. Alliums are rich sources of steroidal saponins, flavonoids, and sulphuric compounds of which steroidal saponins have recently received more attention due to their important pharmacological activities. Allium austroiranicum is a common edible vegetable in western regions of Iran, especially in “Chaharmahal and Bakhtiari” province, where it is named “Lopo” and is considerably used as a raw vegetable, flavoring agent, and as a medicinal plant. Materials & Methods: The chloroform-methanolic extract was fractionated using MPLC, and the appropriate fractions were then subjected to isolation and purification of the constituents by HPLC. Structure elucidation was done using comprehensive spectroscopic methods including 1D and 2D NMR. Antileishmanial effects of the isolated compound against the promastigotes of Leishmania major were evaluated using MTT method. Results: Phytochemical investigation of chloroform-methanol extract of the plant resulted in the isolation and identification of a Nicotianoside C related steroidal saponin and its chemical structure was determined as (25S)-5α-Spirostan-1β,3βdiol-3-O-{α-L-rhamnopyranosyl-(1→2)-{α-L-rhamnopyranosyl-(1→4)}-[β-D-glucopyranoside}. Investigation of in vitro antileishmanial activity of the isolated compound, in 10 and 50 and 100 μg/mL concentrations, exhibited significant leishmanicidal effects against the promastigotes of Leishmania major. Conclusion: The results established a valuable basis for further studies about A. austroiranicum and anti-parasitic activity of steroidal saponins.

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Nicotiana tabacum

Medicinal Plants of the World, Volume 3

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Steroid glycosides of the seeds ofNicotiana tabacum. II. The structures of nicotianosides C and F

Cited by 4 publications

References 7 publications

Ecological Roles and Biological Activities of Specialized Metabolites from the GenusNicotiana

Ecological Roles and Biological Activities of Specialized Metabolites from the GenusNicotiana

Antileishmanial Activity of New Steroidal Saponin Isolated from the Flowers of Allium Austroiranicum

Nicotiana tabacum

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