• KOREAN JOURNAL OF CROP SCIENCE
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• v.61 no.1
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• pp.57-63
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• 2016

Soyasaponin I, II, III and V contents were investigated in seed, cotyledons and sprouts of soybean (Glycine max (L.) Merill) subjected to germination over five days. High-performance liquid chromatography coupled with tandem mass spectrometric (HPLC-MS/MS) method was used to evaluate the content of soyasaponins. Soyasaponins contents were different according to the varieties. Germination of soybeans dramatically increased soyasaponin contents in soybean sprouts in a time-dependent manner. Cotyledons had a higher contents of soyasaponins compared to dried seed (p<0.05). After five days of germination, Soyasaponin I and II increased 10 times higher after germination. Soyasaponin I and II are major metabolites in cotyledons and hypocotyls. Soyasaponin III and V were also detected in seed and increased depended on the germination stage. Soyasaponin V was at its highest levels in the hypocotyl, almost 7 times higher than the initial content in soybean seeds. Therefore, the germination of soybean sprouts significantly increased soyasaponin content.

• Biomolecules & Therapeutics
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• v.17 no.4
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• pp.430-437
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• 2009

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: m/z 941 [M-H]$^-$, m/z 795 [M-rha-H]$^-$, m/z 441 [aglycone-$H_2O$+H]$^+$, and m/z 633 [M-rha-gal-H]$^-$, which was an unknown metabolite, soyasapogenol B 3-$\beta$-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-$\beta$-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.

• Journal of Plant Biotechnology
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• v.50
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• pp.70-75
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• 2023

In legumes, soyasaponins, one of triterpenoid saponins, are major components of secondary metabolites with a more diverse array of bioactive chemicals. Although the biosynthetic pathway of soyasaponins has been largely studied in soybean, the study on the soyasaponin contents and biosynthesis-related gene expression in pea (Pisum sativum L.) is poorly understood. Here, we found the accumulation of only soyasaponin Bb component in the sprouts of two Korean domestic pea cultivars (Dachung and Sachul). This pattern was consistent with our observation that increased expression of PsUGT73P2 and PsUGT91H4 genes, but not PsCYP72A69, could be responsible for biosynthesis of only soyasaponin Bb in pea by examining their gene expression. However, gradual accumulation of soyasaponin Bb at developmental stages was not consistent with the expression of PsUGT73P2 and PsUGT91H4, suggesting that the changes of their protein activities may affect the accumulation patterns of soyasaponin Bb. We also revealed that the increased expression levels of PsUGT73P2 and PsUGT91H4 during light to dark transition led to increase of soyasaponin Bb contents. Collectively, our results provided a molecular basis of metabolic engineering for enhancing useful soyasaponin Bb metabolites in Korean domestic pea cultivars.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.51 no.4
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• pp.340-347
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• 2006

Soyasaponins $A_1$, DDMP-conjugated group B soyasaponins ${\alpha}g\;and\;{\beta}g$, non-DDMP counterpart soyasaponin I, II+III, and DDMP moiety were quantified in the large-, midium-, and small-seed soybean varieties. Protein contents were ranged from 38.1% to 41.8%, and oil contents were ranged from 15.5% to 18.9%, respectively. Oil contents in the large-seed varieties were significantly higher than those of medium- and small-seed varieties. Among detected soyasaponin peaks, ${\beta}g$ was a major soyasaponin in DDMP-conjugated group B soyasaponins followed by soyasaponin I, DDMP moiety and $A_1$. Soyasaponin concentration among different seed size soybean varieties. The soyasaponin concentration of mediumseed ($4014.5{\mu}g/g$) was slightly higher than those of largeseed ($3755.0{\mu}g/g$) and small-seed varieties ($3620.3{\mu}g/g$), however, the differences was statistically not significant. The composition rates of soyasaponins in the large-size seeds were 9.4% of soyasaponin $A_1$, 26.5% of DDMP-conjugated soyasaponins, 49.9% of non-DDMP counterpart soyasaponins, and 14.2% of DDMP moiety, respectively. Similar results were observed in the composition ratios of middle- and small-size seeds. Oil content and C:N ratio showed the significant positive correlations with total soyasaponin concentration, while the 100-seed weight, fiber, and ash contents showed the negative correlations with total soyasaponin but statistically not significant. It was noted that protein contents didn't have any relationship with group A, group B, DDMP moiety, and total soyasaponin. This fact suggested that protein contents are not affects the variation of soyasaponin concentration.

• Journal of the Korean Society of Food Science and Nutrition
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• v.36 no.5
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• pp.584-588
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• 2007

Elicitors are defined as substances that induce defense responses in plants, which include an increased synthesis of secondary metabolites. Saponin, one of the secondary metabolites, has various physiological effects such as anticancer, antioxidant, cholesterol-lowering activities, etc, in human. This study was carried out to find whether a treatment of soybean sprouts with chitosan as an elicitor, increases saponin contents. Saponin contents in soybean sprouts increased by the chitosan treatment during cultivation, reached the peak on the sixth day, and then decreased. A biosynthesis of group B soyasaponin appeared to be regulated differently. The content of soyasaponin I, a member of group B saponin, was the highest in 250 ppm chitosan-treated soybean sprouts, while the contents of soyasaponin II, III and IV were the highest in 1,000 ppm chitosan-treated soybean sprouts. The content of soyasaponin V changed little in soybean sprouts that had been treated with various concentration of chitosan.

• Journal of the Korean Society of Food Science and Nutrition
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• v.22 no.3
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• pp.323-327
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• 1993

The effect of soyasaponin on the liposomal phospholipid membrane was investigated by differential scanning calorimetry (DSC). Soyasaponins were obtained and the enthalpy changes and the sizes of cooperative unit of the transition were calculated. The thermograms of L-$\alpha$-dimyristoyl phosphatidylcholine (DMPC) incorporated with soyasaponin showed that the phase transition temperature was significantly lowered and the peak was broadened. This was attributed to the possibility that incorporation of soyasaponin into the lipid bilayers reduced the cooperative unit of phospholipid bilayers. These results indicate soyasaponin might have significant effect on the fluidity of biological membrane.

• Journal of the Korean Society of Food Science and Nutrition
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• v.21 no.4
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• pp.381-385
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• 1992

The effect of antioxidant activity of soyasaponin on the liposomal phospholipid membrane were investigated by spectrophotometry. The oxidation index and oxidation rate of ${\alpha}-tocopherol$ containing egg phosphatidylcholine (EPC) liposomes were markedly decreased in the presence of soyasaponin relative to those of purephospholipid liposmes. ${\alpha}-tocopherol$ containing liposomes delayed the oxidation of liposomes. Especially soyasaponin stimulated the antioxidant activity of ${\alpha}-tocopheroal$ in liposomes. These results indicates that soyasaponin in liposomes had some additive effect on antioxidant of ${\alpha}-tocopherol$ toward liposomes.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.58 no.2
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• pp.149-160
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• 2013

The objective of present study was to simultaneously isolate of isoflavone and soyasaponin compounds from the germ of soybean seeds. Soy germ flours were defatted with hexane for 48h at room temperature, and methanolic extracts were prepared using reflux apparatus at $90^{\circ}C$ for 6h, two times. After extraction, extracts were separated with preparative RP-$C_{18}$ packing column ($125{\AA}$, $55-105{\mu}m$, $40{\times}150mm$), and collected 52 fractions were identified with TLC plate (Kieselgel 60 F-254) and HPLC, respectively. Among the identified isoflavone and soyasaponin fractions, isoflavone fractions were re-separated using a recycling HPLC with gel permeation column (Jaigel-W252, $20{\times}500mm$). Final fractions were air-dried, and the purified compounds of two isoflavones (ISF-1-1, ISF-1-2) and four soyasaponins (SAP-1, SAP-2, SAP-3, SAP-4) were obtained. Two isoflavone compounds (ISF-1-1, ISF-1-2) were acid-hydrolyzed for the identification of their aglycones, and confirmed by comparing with 12 types of isoflavone isomers. While the four kinds of soyasaponins were identified by using a micro Q-TOF mass spectrometer in the ESI positive mode with capillary voltage of 4.5kV, and dry temperature of $200^{\circ}C$. Base on the obtained results, it was conclude that ISF-1-1 is the mixture isomers of daidzin (43.4%), glycitin (47.0%), and genistin (9.6%), but ISF-1-2 is the single compound of genistin (99.8% <). On the other hand, soyasaponin SAP-1 is the mixture compounds of soyasaponin A-group (Aa, Ab, Ac, Ae, Af); SAP-2 is soyasaponin B-group (Ba, Bb, Bc) and E-group (Bd, Be); SAP-3 is soyasaponin B-group (Ba, Bb, Bc), E-group (Bd, Be), and DDMP-group (${\beta}g$); SAP-4 is soyasaponin B-group (Ba, Bb, Bc), E-group (Bd, Be), and DDMP-group (${\beta}g$, ${\beta}a$), respectively.

• Korean Journal of Plant Resources
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• v.25 no.4
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• pp.394-400
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• 2012

Contents of soyasaponin group B were compared according to two regions and ten varieties by HPLC. Those compounds were known to be beneficial for health. After soyasaponins were isolated and identified, those isolated compounds were used for HPLC analysis. The contents of soyasaponin were very different by regions but highest in the soybean with black seed coat. It was appeared that environmental difference for soybean growth could strongly change of soyasaponin contents.

• Bulletin of the Korean Chemical Society
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• v.32 no.10
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• pp.3650-3654
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• 2011

Two new unusual soyasaponins named 6"-O-methyldehydrosoyasaponin I(7) and desglucosylsoyasaponin $A_1$ (10) along with eight known saponins, dehydrosoyasaponin IV (1), dehydrosoyasaponin III (= impatienoside A) (2), soyasaponin III (3), dehydrosoyasaponin II (= soyasaponin Bg) (4), soyasaponin II (5), dehydrosoyasaponin I (= soyasaponin Be) (6), soyasaponin I (8), and kudzusaponin $SA_3$ (9), were isolated as their methyl esters and identified from the liquid culture of G. applanatum. Their structures were determined by chemical and spectroscopic analyses including 1D- and 2D-NMR as well as by comparison of their spectroscopic data with those of the reported in literatures. Although dehydrosoyasaponin IV was identified by LC-MS/MS method from soy protein isolate, this is the first report of the isolation of this compound. Dehydrosoyasaponin III (2) and kudzusaponin $SA_3$ (9) were also isolated for the first time from soybean. The presence of soyasaponins in Ganoderma species seems to be unusual feature. Thus, we presumed that compounds 1-10 might all be derived from the defatted soybean flour which was added to the culture medium as a nitrogen source.