Isolation and Structural Elucidation of the Major Genuine Soybean Saponin

Kudou, Shigemitsu; Tonomura, Masahide; Tsukamoto, Chigen; Shimoyamada, Makoto; Uchida, Teiji; Okubo, Kimihiro

doi:10.1271/bbb.56.142

Cited by 105 publications

(57 citation statements)

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“…The results on the stability of DDMP-conjugated soyasaponins were not consistent in the literature. Kudou (15) observed that soyasaponins Rg and g converted into soyasaponins V and I, respectively, when the alcoholic extract of soy hypocotyls was heated at 80°C for 5 h. Massiot (18) reported that soyasaponin g converted into soyasaponin I in acidic or basic solutions or standing in alcoholic solution at ambient temperature. Okubo (19) found that the isolated soyasaponin g was stable at acidic pH but rapidly degraded into soyasaponin I at basic pH solution or in the presence of FeCl 3 .…”

Section: Resultsmentioning

confidence: 99%

Quantification of the Group B Soyasaponins by High-Performance Liquid Chromatography

Lee

Hendrich

et al. 2002

J. Agric. Food Chem.

122

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High-performance liquid chromatographic methods were developed for the isolation and quantitative determination of the group B soyasaponins, including 2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP)-conjugated soyasaponins Rg, f3g, and f3a, and their non-DDMP counterparts, soyasaponins V, I, and II, respectively, with formononetin used as the internal standard. The limits of quantification for soy products were 0.11-4.86 µmol/g. The within-day and between-days assay coefficients of variation were <9.8 and < 14.3%, respectively. The group B soyasaponin concentrations in 46 soybean varieties ranged from 2.50 to 5.85 µmol/g. Soy ingredients (soybean flour, toasted soy hypocotyls, soy protein isolates, textured vegetable protein, soy protein concentrates, and Novasoy) and soy foods (commercial soy milk, tofu, and tempeh) contained the group B soyasaponins from 0.20 to 114.02 µmol/g. There was no apparent correlation between isoflavone and soyasaponin concentrations in the soy products examined. High-performance liquid chromatographic methods were developed for the isolation and quantitative determination of the group B soyasaponins, including 2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP)-conjugated soyasaponins Rg, g, and a, and their non-DDMP counterparts, soyasaponins V, I, and II, respectively, with formononetin used as the internal standard. The limits of quantification for soy products were 0.11-4.86 µmol/g. The within-day and between-days assay coefficients of variation were <9.8 and < 14.3%, respectively. The group B soyasaponin concentrations in 46 soybean varieties ranged from 2.50 to 5.85 µmol/g. Soy ingredients (soybean flour, toasted soy hypocotyls, soy protein isolates, textured vegetable protein, soy protein concentrates, and Novasoy) and soy foods (commercial soy milk, tofu, and tempeh) contained the group B soyasaponins from 0.20 to 114.02 µmol/g. There was no apparent correlation between isoflavone and soyasaponin concentrations in the soy products examined.

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Section: Resultsmentioning

confidence: 99%

Quantification of the Group B Soyasaponins by High-Performance Liquid Chromatography

Lee

Hendrich

et al. 2002

J. Agric. Food Chem.

122

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“…The n-butanol fraction was subjected to chromatography on a MPLC [column, Silica gel 100 C18-reverse phase (Fluka Co., USA); elution solvent, a linear-gradient applied by 10% CH 3 CN in H 2 O to 70% CH3CN in H2O; a flow rate, 4 ml/min over 4 h], to isolate soyasponogenol B (12 mg; purity, ＞95%). The isolated sayasaponin I and soyasapogenol B were identified by comparison to authentic standards by instrumental (FAB-MS, 1 H-NMR, 13 C-NMR) analysis with that of the previously reported literatures (Kitagawa et al, 1988;Kudou et al, 1992Kudou et al, , 1993.…”

Section: Isolation Of Soyasaponin I and Its Metabolite Soyasapogenol mentioning

confidence: 99%

Metabolism of Soyasaponin I by Human Intestinal Microflora and Its Estrogenic and Cytotoxic Effects

Chang¹,

Han²,

Han³

et al. 2009

Biomolecules and Therapeutics

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-Metabolites of Soyasaponin I, a major constituent of soybean, by human intestinal microflora were investigated by LC-MS/MS analysis. We found four peaks, one parental constituent and three metabolites:which was an unknown metabolite, soyasapogenol B 3-β-D-glucuronide. When soyasaponin I was incubated with the human fecal microbial fraction from ten individuals for 48 h, soyasaponin I was metabolized to soyasapogenol B via soyasaponin III and soyasapogenol B 3-β-D-glucuronide or via soyasaponin III alone. Both soyasaponin I and its metabolite soyasapgenol B exhibited estrogenic activity. Soyasaponin I increased the proliferation, mRNA expression of c-fos and pS2, in MCF7 cells more potently than soyasapogenol B. However, soyasapogenol B showed potent cytotoxicity against A549, MCF7, HeLa and HepG2 cells, while soyasaponin I did not. The cytotoxicity of soyasapogenol B may prevent its estrogenic effect from increasing dose-dependently. These findings suggest that orally administered soyasaponin I may be metabolized to soyasapogenol B by intestinal microflora and that soyasapogenol B may express a cytotoxic effect rather than an estrogenic effect.

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“…We recently reported that chromosaponin I (CSI), a ␥-pyronyl-triterpenoid saponin isolated from pea (Pisum sativum) and other leguminous plants (Tsurumi et al, 1991(Tsurumi et al, , 1992Kudou et al, 1992Kudou et al, , 1993Massiot et al, 1992), specifically interacts with auxin influx carrier AUX1 (Bennett et al, 1996) and changes the response of Arabidopsis roots toward auxin and ethylene by controlling auxin uptake (Rahman et al, 2001a). Application of 60 m CSI inhibited the auxin uptake in the roots of Arabidopsis expressing the wild-type AUX1 protein and slowed down the gravitropic response of roots.…”

mentioning

confidence: 99%

Auxin and Ethylene Response Interactions during Arabidopsis Root Hair Development Dissected by Auxin Influx Modulators

Rahman

Hosokawa²,

Oono³

et al. 2002

Plant Physiology

219

164

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The plant hormones auxin and ethylene have been shown to play important roles during root hair development. However, cross talk between auxin and ethylene makes it difficult to understand the independent role of either hormone. To dissect their respective roles, we examined the effects of two compounds, chromosaponin I (CSI) and 1-naphthoxyacetic acid (1-NOA), on the root hair developmental process in wild-type Arabidopsis, ethylene-insensitive mutant ein2-1, and auxin influx mutants aux1-7, aux1-22, and double mutant aux1-7 ein2. ␤-Glucuronidase (GUS) expression analysis in the BA-GUS transgenic line, consisting of auxin-responsive domains of PS-IAA4/5 promoter and GUS reporter, revealed that 1-NOA and CSI act as auxin uptake inhibitors in Arabidopsis roots. The frequency of root hairs in ein2-1 roots was greatly reduced in the presence of CSI or 1-NOA, suggesting that endogenous auxin plays a critical role for the root hair initiation in the absence of an ethylene response. All of these mutants showed a reduction in root hair length, however, the root hair length could be restored with a variable concentration of 1-naphthaleneacetic acid (NAA). NAA (10 nm) restored the root hair length of aux1 mutants to wild-type level, whereas 100 nm NAA was needed for ein2-1 and aux1-7 ein2 mutants. Our results suggest that insensitivity in ethylene response affects the auxin-driven root hair elongation. CSI exhibited a similar effect to 1-NOA, reducing root hair growth and the number of root hair-bearing cells in wild-type and ein2-1 roots, while stimulating these traits in aux1-7and aux1-7ein2 roots, confirming that CSI is a unique modulator of AUX1.Root hairs are tip-growing, tubular-shaped outgrowths that help to anchor roots, interact with soil microorganisms, and assist in the uptake of water and nutrients (Cutter, 1978). The relatively simple and invariant cellular organization of the primary roots of Arabidopsis and the ease of isolation and characterization of mutants make it a very attractive material for studying the root hair developmental process. The first committed step for root hair development is epidermal cell specification. In many species, including Arabidopsis, the root epidermis consists of two epidermal cell types, root hair-forming trichoblast cells and hairless atrichoblast cells (Cormack, 1947(Cormack, , 1949Bunning, 1951;Cutter, 1978). Within the Arabidopsis root epidermis, cells adopt distinct fates in a position-dependent manner. Epidermal cells that overlay the junction between two cortical cell files adopt a root hair cell fate, whereas the epidermal cells that contact only one cortical cell file become hairless cells (Dolan et al., 1994;Galway et al., 1994; Berger et al., 1998).Once the immature epidermal cell adopts a root hair cell fate, it goes through characteristic changes in its shape and size (Schiefelbein, 2000). Genetic analysis revealed that the root hair initiation mutations axr2 ), axr3 (Leyser et al., 1996, and ctr1 (Kieber et al., 1993) exhibit changes in their response to two i...

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Isolation and Structural Elucidation of the Major Genuine Soybean Saponin

Cited by 105 publications

References 0 publications

Quantification of the Group B Soyasaponins by High-Performance Liquid Chromatography

Quantification of the Group B Soyasaponins by High-Performance Liquid Chromatography

Metabolism of Soyasaponin I by Human Intestinal Microflora and Its Estrogenic and Cytotoxic Effects

Auxin and Ethylene Response Interactions during Arabidopsis Root Hair Development Dissected by Auxin Influx Modulators

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