Isolation and Structural Elucidation of DDMP-Conjugated Soyasaponins as Genuine Saponins from Soybean Seeds

Kudou, Shigemitsu; Tonomura, Masahide; Tsukamoto, Chigen; Uchida, Teiji; Sakabe, Terumi; Tamura, Nobuhiro; Okubo, Kimihiro

doi:10.1271/bbb.57.546

Cited by 148 publications

(113 citation statements)

References 3 publications

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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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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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“…Several structurally diverse groups of soyasaponins have been identified from the seeds of the subgenus Soja which includes the cultivated and wild soybean. [3][4][5][6][7][8][9][10][11][12] Based on the aglycone structure, soyasaponins have been classified into group A, DDMP (2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one), group H, group I, and group J saponins (Fig. 1).…”

mentioning

confidence: 99%

“…DDMP saponins are degraded during most extraction procedures to form group B saponins having SS-B and group E saponins having soyasapogenol E (SS-E). 7) Sg-6 saponins are monodesmosides with one sugar chain at the C-3 hydroxyl position of their respective soyasapogenols (SS-H, SS-I, and SS-J). 6) The nomenclature of all soyasaponins was derived from these six aglycones and their sugar moiety composition (Fig.…”

mentioning

confidence: 99%

Comparison of saponin composition and content in wild soybean (Glycine soja Sieb. and Zucc.) before and after germination

Krishnamurthy

Tsukamoto

Takahashi

et al. 2014

Bioscience, Biotechnology, and Biochemistry

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Eight wild soybean accessions with different saponin phenotypes were used to examine saponin composition and relative saponin quantity in various tissues of mature seeds and two-week-old seedlings by LC–PDA/MS/MS. Saponin composition and content were varied according to tissues and accessions. The average total saponin concentration in 1 g mature dry seeds of wild soybean was 16.08 ± 3.13 μmol. In two-week-old seedlings, produced from 1 g mature seeds, it was 27.94 ± 6.52 μmol. Group A saponins were highly concentrated in seed hypocotyl (4.04 ± 0.71 μmol). High concentration of DDMP saponins (7.37 ± 5.22 μmol) and Sg-6 saponins (2.19 ± 0.59 μmol) was found in cotyledonary leaf. In seedlings, the amounts of group A and Sg-6 saponins reduced 2.3- and 1.3-folds, respectively, while DDMP + B + E saponins increased 2.5-fold than those of mature seeds. Our findings show that the group A and Sg-6 saponins in mature seeds were degraded and/or translocated by germination whereas DDMP saponins were newly synthesized.

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“…DDMP soyasaponins and the acetylated soyasaponins of group A are sometimes considered as the genuine forms of groups A and B in soybeans. Group E soyasaponins are also considered to be phyto-oxidation products of group B soyasaponins (62,67,68). All four groups of soysaponins are glycosides of oleanan triterpene aglycones known as soyasapongenols.…”

Section: Chemical Characteristics Of Soyasaponins and Soyasapogenolsmentioning

confidence: 99%

“…DDMP soyasaponins are categorized under B type soyasaponins by some researchers (27). Their structures were characterized as having DDMP group conjugated to group B at C-22 (67,68,73,74) NO. name C-3 sugar chain C-22 sugar chain molecular formula (Figure 4).…”

Section: Chemical Characteristics Of Soyasaponins and Soyasapogenolsmentioning

confidence: 99%

Phytochemicals in Soy and Their Health Effects

Wu¹,

Kang²

2011

Phytochemicals - Bioactivities and Impact on Health

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Isolation and Structural Elucidation of DDMP-Conjugated Soyasaponins as Genuine Saponins from Soybean Seeds

Cited by 148 publications

References 3 publications

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

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

Comparison of saponin composition and content in wild soybean (Glycine soja Sieb. and Zucc.) before and after germination

Phytochemicals in Soy and Their Health Effects

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