• 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.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.55 no.2
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• pp.165-176
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• 2010

Soybean seeds contain many biologically active secondary metabolites, such as proteins, saponins, isoflavones, phytic acids, trypsin inhibitors and phytosterols. Among them, saponins in soybeans have attracted considerable interest because of their health benefits. Soyasaponin A and B are the most abundant types of saponins found in soybeans along with soyasapogenol (aglycone), which is a precursor of soyasaponin. The main purpose of this experiment was to determine the concentration of soyasapogenol in soybean seeds and sprouts as a function of seed size, usage, seed coat color and seed cotyledon color. The 79 Korean soybean varieties were cultivated at Yesan of Chungnam in 2006 for the analysis of soyasapogenol using HPLC with Evaporative Light Scattering Detection (ELSD). The total average concentration of soyasapogenol was $1313.52{\mu}g\;g^{-1}$ in soybean seeds and $1377.22{\mu}g\;g^{-1}$ in soybean sprouts. Soybean sprouts were about 5% higher than soybean seeds in average total soyasapogenol concentration. In the process of sprouting, the average soyasapogenol A content decreased by approximately 1.6%, but soyasapogenol B and total soyasapogenol increased by 8.31% and 4.88%, based on the content of soybean seeds. When classified according to the size of seeds, the total soyasapogenol concentration of soybean seeds were not significantly different (p<0.05) On average, small soybean seeds were increased by as much as $103.14{\mu}g\;g^{-1}$ in sprouting process. As a function of the use of the seeds, The total soyasapogenol in soybean seeds were significantly different (p<0.05). While, the soybean sprouts were not significant different (p<0.05). Altogether, sprout soybean seeds show the greatest change in content during the germination process. When seeds with different coat colors were compared, the total soyasapogenol concentration of soybean with yellow seed coats ($1357.30\mu g\;g^{1}$) was slightly higher than that of soybean with black ($1260.30{\mu}g\;g^{-1}$) or brown ($1263.62{\mu}g\;g^{-1}$) seed coats. For the color of the cotyledon, the total soyasapogenol concentration was significantly increased in green cotyledon during the germination and seedling process. The results of this study suggest the functional characteristics of soybeans through quantitative analysis of soyasapogenol. In addition, the concentration of soyasapogenol exhibited a change during the germination process, which was evaluated by the nutritional value of the soybean sprouts.

• Archives of Pharmacal Research
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• v.10 no.1
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• pp.9-13
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• 1987

From the aerial parts of Melilotus officinalis (Leguminosae) soyasapogenols B, mp 259-260.deg., and E, mp 246-247, were isolated along with coumarin and kaempferol. This is the first report of the isolation of soyasapogenols from the genus Meliotus.

• Analytical Science and Technology
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• v.34 no.4
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• pp.172-179
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• 2021

Oleanane-type triterpenoids exist as secondary metabolites in various plants. In particular, soyasaponin, an oleanane-type triterpenoid, is abundant in the hypocotyl of soybean, one of the most widely cultivated crops in the world. Depending on their chemical structure, soyasaponins are categorized as group A saponins or group DDMP (2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one) saponins. The different soyasaponin chemical structures present different health functionalities and taste characteristics. However, conventional phenotype screening of soybean requires a substantial amount of time for functionality of soyasaponins. Therefore, we attempted to use liquid chromatography with a photodiode array detector and tandem mass spectrometry (LC-PDA/MS/MS) for accurately predicting the phenotype and chemical structure of soyasaponins in the hypocotyl of five common soybean natural mutants. In this method, the aglycones (soyasapogenol A [SS-A] and soyasapogenol B [SS-B]) were detected after acid hydrolysis. These results indicated that the base peak and fragmentation differ depending on the chemical structure of soyasaponin with aglycone. Thus, a fragmentation database can help predict the chemical structure of soyasaponins in soyfoods and plants.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.65 no.4
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• pp.457-467
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• 2020

Legumes are one of the largest families of crop plants and are widely consumed and produced for their nutritional and commercial benefits. Mung bean (Vigna radiata L.) is a legume crop that contains various functional compounds ; moreover, it has strong antioxidant properties and is becoming an increasingly important food crop. However, most previous studies on mung beans have focused on their primary metabolites. In this study, we investigated the composition and contents of phenolic compounds, fatty acids, soyasapogenol and tocopherol in mung beans cultivated in different regions and cultivated at different seeding dates. Material analysis was conducted using the following methods: LC-MS/MS, GC-FID and HPLC-ELSD. In total, 57 different samples were analyzed. Thirteen phenolic compounds were detected in mung beans. Of these, vitexin and isovitexin were the most abundant compounds, accounting for approximately 99% of phenolic compounds. The difference in phenol compounds according to the seeding dates of mung bean was not statistically significant. The total fatty acid content in beans was the highest in Pyeongchang. Significant differences in total fatty acid content were found according to the cultivation regions. Crops grown in Sohyeon and Dahyeon showed the highest soyasapogenol B content in the Suwon region, and these were the lowest in Jeonju. The total tocopherol content of beans cultivated in Dahyeon and Sohyeon was the lowest and highest in Pyeongchang. Soyasapogenol B and total tocopherol content were not significantly different according to seeding dates. This study was conducted to obtain basic data for the cultivation of mung beans with a high content of various functional materials in terms of regional specialization and optimal seeding time.

• Korean Journal of Pharmacognosy
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• v.18 no.2
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• pp.89-93
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• 1987

Chemical investigation of the inhibitory compound on leucocyte migration from Melilotus officinalis has led to the isolation and characterization of azukisaponin V $(3-O-[{\alpha}-L-rhamonopyranosyl(1{\rightarrow}2)-{\beta}-D-glucopyransosyl(1{\rightarrow}2)-{\beta}-D-glucuronopyranosyl]-soyasapogenol B)$ as the carboxylate form, which exhibits potent leucocyte migration inhibitory activity at a dose of 6mg/rat.

• Archives of Pharmacal Research
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• v.11 no.3
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• pp.197-202
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• 1988

A new saponin, 3-O-[${\alpha}$-L-rhamnopyranosyl$(1{\rightarrow}2)$-${\beta}$-D-glucopyranosyl$(1{\rightarrow}2)$-${\beta}$-D-glucuronopyranosyl]soyasapogenol B carboxylate (6) has been isolated from the medicinal plant yellow sweetclover together with azukisaponin II(7), robinin(8), and clovin(9). 7,8, and 9 are reported for the first time from this plant. The new saponin(6) exhibited inhibitory action on leucocyte migration in inflammation.

• Proceedings of the Korean Society of Applied Pharmacology
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• 1994.04a
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• pp.226-226
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• 1994

천연의 Triterpene이나 Steroid의 01igo당 배당체는 항균작용, 소염작용, 항암작용등의 유용한 생리활성을 가지는것이 많다. 따라서 이들 화합물군으로 부터 신의약품이 개발될 가능성이 매우크다 하겠다. 그러나 천연물은 그 작용이 약하거나 순수하게 다량 분리하기가 쉽지않다. 생리활성이 강하고, 부작용이 적은 배당체를 이용가능한 양만큼 다량을 순수하게 얻기 위하여는 합성의 기법이 절대적으로 필요하다. 이를 위하여 연구자는 천연의 총배당체 (배당체혼합물)로부터 aglycone을 얻고 여기에 g1ycosidation 반응으로 당을 결합시킴으로써 천연 또는 비 천연성 배당체를 합성하고 생리활성을 검토, 신물질을 창출하고자 한다. Aglycone으로는 Ginsenosides의 aglycone인 20(s)-protopanaxadiol 및 20(S)-protopanaxatriol, Soyasapogenol B, Oleanlic acid를 사용하고, 목표로하는 생리활성은 항암작용, 항군작용, alcohol 흡수 저해작용을 지향한다.

• Natural Product Sciences
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• v.6 no.1
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• pp.11-15
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• 2000

Two soyasaponins were isolated from the aerial parts of Astragalus tribuloides Del. Their structures were established on the basis of spectroscopic and chemical methods. In addition, ursolic acid, ${\beta}-sitosterol\;{\beta}-D-glucoside$ and isorhamnetin 3-O-glucoside were isolated and identified by comparing their mp, spectral and chromatographic data with those of authentic samples. This is the first report of screening and isolation of the chemical constituents of this species of genus Astragalus.

• Natural Product Sciences
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• v.14 no.4
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• pp.281-288
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• 2008

From the MeOH extract of the whole plants of Lathyrus davidii (Fabaceae), thirteen constituents were isolated and identified as the flavonoids astragalin, isoquercitrin, nicotiflorin, and rutin, as the saponins soyasapogenol B 3-O-${\beta}$-D-glucuronopyranoside, azukisaponins II and V, soyasaponins II and V and as 4-O-${\beta}$-Dglucopyranosyl syringic acid, uracil and n-hexacosanol. Five saponins and 4-O-${\beta}$-D-glucopyranosyl syringic acid were isolated from the BuOH fraction as their methyl esters. Ombuoside (rutin 7,4'-di-O-methyl ether) was also isolated from the methylated BuOH-soluble fraction. However, no ombuoside was detected in the HPLC analysis of the nonmethylated BuOH fraction. Therefore, ombuoside is an artifact derived from methylation of rutin. All of these compounds were isolated for the first time from this plant.