Steroid glycosides ofNicotiana tabacum seeds I. The structures of nicotianosides A, B, and E

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

doi:10.1007/bf00630603

Cited by 5 publications

(4 citation statements)

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“…tabacum with spirostane, nicotianosides A ( 408 ) and B ( 409 ) and furostane nicotianoside E ( 410 ) aglycones, respectively (Figure ). Progestrone ( 411 ) and androstendione ( 412 ), two mammalian steroids, were quantified in N. tabacum using UPLC-ESI-MS-MS method .…”

Section: Metabolite Classes: Structures and Functionsmentioning

confidence: 99%

“…373 However, some steroidal glycosides have been isolated from N. tabacum with spirostane, nicotianosides A (408) and B (409) and furostane nicotianoside E (410) aglycones, respectively (Figure 31). 441 Progestrone (411) and androstendione (412), two mammalian steroids, were quantified in N. tabacum using UPLC-ESI-MS-MS method. 442 Insects cannot biosynthesize sterols, and they obtain them from their host plants.…”

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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“…Methanol/water (80/20 v/v) extracts of the aerial parts and roots of A. africanus were fractionated and purified by successive chromatographic techniques yielding thirty-three specialized metabolites including ten undescribed compounds (4-13) and twenty-three known compounds (1-3 and 14-33) (Supplemenary data ). The known compounds were identified by comparing their spectral data with literature values as referenced: (Huang et al, 2008) (Shvets et al, 1994) (Terada et al, 1995), asparenydiol ( 14) (Miyakoshi et al, 2000), 5-[5-(4-hydroxyphenoxy)-3penten-1-ynyl]-2-methoxyphenol (15), previously isolated from Asparagus gobicus under the name of 1-methoxy-2-hydroxy-4-[5-(4-hydroxyphenoxy)-3-penten-1-ynyl]-phenol (Yang et al, 2005), nyasol ( 16) (Tsui et al 1996 ;Oketch-Rabah et al, 1997), 3'-methoxynyasol (17), 3′hydroxy-4′-methoxy-4′-dehydroxynyasol (18) (Zhang et al, 2004), iso-agatharesinol (19) (Yang et al, 2004a), 1-O-p-coumaroylglycerol (20) (Luo et al, 2012), syringaresinol (21), syringaresinol-4-O-β-D-glucopyranoside ( 22) (Tong et al, 2005 ;Inui et al, 2010), hordénine (23) (Küçükosmanoǧlu et al, 2005), N-methyltyramine (24) (Nash et al, 1992), apigenin 6-Cβ-D-glucopyranosyl-8-C-β-D-ribopyranoside (25), apigenin 6-C-α-L-arabinopyranosyl-8-C-β-Dglucopyranoside (26), vicenin 3 (27) (Chimichi et al, 1998 ;Chen et al, 2019), quercetin 3- (Adell et al, 1988;Eldahshan, 2011), benzyl-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (30) (De Tommasi et al, 1996), aurantiamide acetate (31) (Zhou et al, 2017), asperphenamate (32) (Catalán et al, 2003) and sesamin (33) that was identified by comparison with spectral data available at our laboratory.…”

Section: Identification Of Compoundsmentioning

confidence: 99%

Chemical constituents and antioxidant capacities of Asparagus africanus Lam.

Akissi

Yao-Kouassi

Magid

et al. 2023

Phytochemistry Letters

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“…These compounds possess antitumor [1], antimierobial [2], fungicidal [3], and antiviral [4] activities, and are capable of decreasing blood cholesterol level [5] and producing antioxidant action [6]. These steroids can be obtained from many species of plants belonging to various genera and families such as Dioscoreaceae, Solanaceae, and Liliaceae.…”

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confidence: 99%

Hypolipidemic properties of atroposides

et al. 1997

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Steroids of the spirostan and furostan series exhibit a broad spectrum of biological effects. These compounds possess antitumor [1], antimierobial [2], fungicidal [3], and antiviral [4] activities, and are capable of decreasing blood cholesterol level [5] and producing antioxidant action [6]. These steroids can be obtained from many species of plants belonging to various genera and families such as Dioscoreaceae, Solanaceae, and Liliaceae. We have found for the first time new steroid glycosides, called atroposides, in the seeds of Atropa belladonna L. from the Solanaceae family. EXPERIMENTAL CHEMICAL PARTWe studied the seeds of A. belladonna obtained at the "Giaginskii" collective farm in Krasnodar Province. To obtain spirostan glycosides, the air-dry seeds were ground, degreased with chloroform, and multiply extracted with 70% aqueous methanol. The methanol extract was evaporated to aqueous residue, which was treated several times with butanol. The butanol extracts were concentrated in a vacuum and dissolved in a small amount of methanol Finally, the total glycosides were precipitated with acetone, filtered, and dried. The presence of steroid glycosides was determined by TLC. The spots were visialized by the Sanyo and Ehrlich reagents. The total antroposide yield was 3.95% of the initial raw material weight.The sum of antroposides was separated into individual fractions by methods of gel-filtration on sephadex and adsorption-partition chromatography on silica gel, using various solvent systems: chloroform-methanol (4: 1), chloroform-methanol-water (65 : 35 : 10).The structure of aglycone and the qualitative composition of monosaccharides in the carbohydrate fraction of glycosides were determined by a method of complete acid hydrolysis. The aglycone structures were identified with those of tigogenin and diosgenin. The oligosaccharide fraction ineluded glucose, rhamnose, and galactose.In order to prove the structure of spirostan glycosides from A. belladonna, we used the methods of partial acid hy-

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Steroid glycosides ofNicotiana tabacum seeds I. The structures of nicotianosides A, B, and E

Cited by 5 publications

References 4 publications

Ecological Roles and Biological Activities of Specialized Metabolites from the GenusNicotiana

Ecological Roles and Biological Activities of Specialized Metabolites from the GenusNicotiana

Chemical constituents and antioxidant capacities of Asparagus africanus Lam.

Hypolipidemic properties of atroposides

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