Detection of Proto-type Compounds of Diosgenin-and Other Spirostanol-Glycosides

Kiyosawa, Shu; Hutoh, Masakazu; Komori, Tetsuya; Nohara, Toshihiro; Hosokawa, Ichiro; Kawasaki, Toshio

doi:10.1248/cpb.16.1162

Cited by 166 publications

(43 citation statements)

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“…L'éluant B = chloroforme -méthanol -ammoniaque à 1% (2-2-1; V/V) est aussi utilisé pour séparer les hétérosides de la solasodine (Verbist, 1971 (1984,1985 (Brunel, 1949 (Oakenfull, 1981;Price 1987 (Kiyosawa & Hutoh, 1968). Les SNA type spirostanol n'apparaîtraient que secondairement dans la plante.…”

Section: Introductionunclassified

Saponosides stéroïdiques de l'aubergine (Solanum melongena L.) I. Intérêt alimentaire, méthodologie d'analyse, localisation dans le fruit

Aubert¹,

Daunay²,

Pochard³

1989

Agronomie

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Relationships between the content of these substances and the typical bitterness of these fruits are investigated. With the exception at the saponins which have a oxygenated heterocyclic structure, the glycoalkaloids are close to the structure of the potato solanins. Organoleptic acceptability threshold, dietetic and culinary aspects of these substances are discussed.solanaceae -saponins -alcaloids -sensory quality INTRODUCTION

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Section: Introductionunclassified

Saponosides stéroïdiques de l'aubergine (Solanum melongena L.) I. Intérêt alimentaire, méthodologie d'analyse, localisation dans le fruit

Aubert¹,

Daunay²,

Pochard³

1989

Agronomie

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“…Furthermore, NMR data clearly revealed the presence of hexoses (glucose), deoxyhexose (rhamnose), and pentose (xylose) in the ratio of 3 : 1 : 1, respectively. The b-configuration of the d-glucopyranosyl and d-xylopyranosyl units was established by the homonuclear coupling constants (6.1, 7.6, 8.1, and 7.6 Hz) of the anomeric protons [13], whereas the aconfiguration of the l-rhamnopyranosyl unit was deduced from the chemical shift of C(5) (d 69.5) [16] ( Table 2) Compounds 4 and 5, also obtained as a mixture, showed an absorption in their IR spectrum characteristic for compounds of the spirostanol type. Detailed analysis of 1D-and 2D-NMR spectra suggested a mixture of tetraglycosidic spirostenes with different configurations at C(25).…”

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New Steroidal Glycosides from Balanites aegyptiaca

Farid

Haslinger

Kunert

et al. 2002

HCA

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“…Spots of both glycosides were colored yellowish-green on spraying chromatograms with Sannie reagent [3]; rosy red, with Erlich reagent [4]. The IR spectrum of the mixture exhibited a weak broad band at 895 cm -1 [5] and lacked bands for the spiro-ketal group characteristic of spirostane-type glycosides [6].…”

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Furostane-Type Steroidal Saponin from Digitalis ciliata

Gvazava

Kikoladze²

2010

Chem Nat Compd

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A new furostane-type steroidal glycoside and derivative of tigogenin (1) was isolated from aqueous wastes from production of the cardiac drug acetyldigitoxin from leaves of Digitalis ciliata Trautv. (Scrophulariaceae) and characterized. The structure of the glycoside was established using physical constants, chemical transformations, and spectral data Ciliate foxglove (Digitalis ciliata Trautv.) (Scrophulariaceae) is widely distributed in alpine meadows of Georgia and is endemic to both the Republic and the whole Caucases region.We reported previously on three new glycosides isolated from aqueous wastes from production of the drug acetyldigitoxin [1, 2] from leaves of ciliate foxglove. Herein we present results from a study of the chemical structure of a new furostane-type tigogenin glycoside, pentaoside 1.The water-soluble total steroidal glycosides were chromatographed repeatedly over a column of silica gel to isolate a mixture of two compounds with similar R f values (1a and 1b). Spots of both glycosides were colored yellowish-green on spraying chromatograms with Sannie reagent [3]; rosy red, with Erlich reagent [4]. The IR spectrum of the mixture exhibited a weak broad band at 895 cm -1 [5] and lacked bands for the spiro-ketal group characteristic of spirostane-type glycosides [6].The PMR spectrum of glycoside 1b showed a strong 3H singlet for methoxyl at G 3.14 whereas it was missing in the spectrum of 1a. The data were typical of furostane-type compounds. The 22-OH group is readily alkylated by lower alcohols (MeOH, EtOH) in the presence of silica gel due to its high reactivity. Therefore, the native 22-OH-furostane is practically always accompanied by its slightly less polar 22-O-methyl/ethyl ether.Heating the mixture of glycosides in water for 2 h produced 1, total acid hydrolysis of which isolated the aglycon tigogenin and a mixture of monosaccharides. TLC and GC detected D-glucose, D-galactose, and D-fucose in a 3:1:1 ratio.

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Detection of Proto-type Compounds of Diosgenin-and Other Spirostanol-Glycosides

Cited by 166 publications

References 0 publications

Saponosides stéroïdiques de l'aubergine (Solanum melongena L.) I. Intérêt alimentaire, méthodologie d'analyse, localisation dans le fruit

Saponosides stéroïdiques de l'aubergine (Solanum melongena L.) I. Intérêt alimentaire, méthodologie d'analyse, localisation dans le fruit

New Steroidal Glycosides from Balanites aegyptiaca

Furostane-Type Steroidal Saponin from Digitalis ciliata

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