• KOREAN JOURNAL OF CROP SCIENCE
• /
• v.61 no.1
• /
• pp.57-63
• /
• 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
• /
• v.17 no.4
• /
• pp.430-437
• /
• 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.

• KOREAN JOURNAL OF CROP SCIENCE
• /
• v.56 no.3
• /
• pp.244-249
• /
• 2011

A sensitive and rapid high-performance liquid chromatographic-tandem mass spectrometric (HPLC/MS/MS) assay was developed for the determination of soyasaponins in soybean. Among soyasaponins, soyasaponin I was isolated and characterized from methanol extracts of soybean as analytical standards and the development of a new analytical procedure for quantification of its content in various cultivars. The structures of these compound was elucidated by $^1H$, $^{13}C$ NMR experiments and by mass spectrometric analysis. Aqueous ethanol extracts of soybean samples were injected on an Agilent XDB-C18 column ($4.6mm{\times}50mm$, $1.8{\mu}m$) with a mobile phase consisting of 10 mM ammonium acetate-acetonitrile, a flow rate of 0.3 mL/min and a total run time of 8 min. Detection was performed by mass spectrometer bin the multiple reaction monitoring (MRM) mode with negative electrospray ionization (ESI) m/z at 941 ${\rightarrow}$ 615 for soyasaponin I. In the 9 soybean samples, contents of soyasaponin I ranged from 205 to 726 mg/kg, and correlated negatively with seed size.

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

• KOREAN JOURNAL OF CROP SCIENCE
• /
• v.51 no.4
• /
• pp.340-347
• /
• 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
• /
• v.36 no.5
• /
• pp.584-588
• /
• 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.

• KOREAN JOURNAL OF CROP SCIENCE
• /
• v.51 no.spc1
• /
• pp.166-173
• /
• 2006

Soyasaponins are phytochemicals of major interest fur their health benefits. Chemical investigation of a soybean phytochemical concentrate resulted in the isolation and identification of triterpenoid saponins. The MeOH extraction of defatted hypocotyl separated from soybeans was peformed by the automated solvent extractor (ASE). Fractionation was performed on a flash column ($150mm{\times}40mm$ i.d.) packed with a preparative $C_{18}$ reverse phase bulk packing material $(125\AA,\;55-105{\mu}m)$ and monitored at 210 nm, and collected 14 fractions. Consequent Fsat preparative column liquid chromatography (Fast PCLC) was performed for the purification of Fraction-I (Fr-I) collected from the fraction 8 and 9 of flash chromatography. Fsat PCLC was performed on a Luna $C_{18}\;10{\mu}m,\;100{\AA}$, semipreparative reverse phase column ($250cm{\times}50mm$ i.d.) for the purification of isolated unknown compound (Fr-I-2). Chemical structure of acetyl soyasaponin $A_1\;(MW:1436.6,\;C_{67}H_{104}O_{33})$ was identified and determined by a combination of extensive NMR ($^1H-NMR$, 400 MHz; $^{13}C-NMR$, 100 MHz; DEPT), IR, UV, and ESI-MS analysis.

• Korean Journal of Food Science and Technology
• /
• v.35 no.6
• /
• pp.1039-1044
• /
• 2003

We investigated the changes in saponins during the cultivation of soybean sprout. Crude saponin content was 4.15mg/g in germinated soybean and reached its peark (5.33mg/g) in soybean sprout cultivated for six days. Saponin content in the cotyledon, stem, and root of the soybean sprout cultivated for six days were 4.17, 7.46, and 7.45mg/g, respectively. Soyasaponins extracted from the soybean sprout were analyzed with LC-electrospray ionization (ESI)-mass spectrometry, in which a reverse phase $C_18$ column was used for separation of saponins. In the soybeen sprout, group B saponin, I, II, III, IV, and V increased 7, 2, 1.4, 8.7, and 3.3 fold, respectively, compared to those in the soybean seed. Group B saponin I, II, III, IV, and V in the stem of the soybean sprout were 10.53, 1.45, 10.49, 5.72 and 8.14 fold the level of those in the cotyldon, respectively. In the root, the contents of group B saponin I, III, IV, and V were 5.54, 2.77, 4.86 and 9.73 fold, respectively, higher than those in cotyledon, but the content of group B saponin 2 was 2.96 fold less than that in cotyledon. These results indicate that the biosyntheses of group B saponins are differentially regulated in growing soybean sprout.

• Journal of Microbiology and Biotechnology
• /
• v.30 no.11
• /
• pp.1697-1705
• /
• 2020

Meju, a type of fermented soybean paste, is used as a starter in the preparation of various Korean traditional soybean-based foods. In this study, we performed Illumina-MiSeq paired-end sequencing for microbial communities and mass spectrometry analysis for metabolite profiling to investigate the differences between 11 traditional meju products from different regions across Korea. Even though the bacterial and fungal communities showed remarkable variety, major genera including Bacillus, Enterococcus, Variovorax, Pediococcus, Weissella, and Aspergillus were detected in every sample of meju. The metabolite profile patterns of the 11 samples were clustered into two main groups: group I (M1-5) and group II (M6-11). The metabolite analysis indicated a relatively higher amino acid content in group I, while group II exhibited higher isoflavone, soyasaponin, and lysophospholipid contents. The bioactivity analysis proved that the ABTS (2,2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid)) radical-scavenging activity was higher in group II and the FRAP (ferric reducing antioxidant power) activity was higher in group I. The correlation analysis revealed that the ABTS activity was isoflavonoid, lipid, and soyasaponin related, whereas the FRAP activity was amino acid and flavonoid related. These results suggest that the antioxidant activities of meju are critically influenced by the microbiome and metabolite dynamics.