Isolation of 2,4,4′-Trihydroxydeoxybenzoin and 3′-Hydroxydaidzein from Soybean Miso (original) (raw)
DPPH Radical-Scavenging Compounds from Dou-Chi, a Soybean Fermented Food
Bioscience, Biotechnology, and Biochemistry, 2005
Dou-chi, a traditional soybean food fermented with Aspergillus sp., is usually used as a seasoning in Chinese food, and has also been used as a folk medicine in China and Taiwan. As 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavengers, four phenol compounds, one isoflavanone, eight isoflavones and one 4-pyrone have been isolated from dou-chi. Among these fourteen compounds, 3 0 -hydroxydaidzein, dihydrodaidzein and a 4pyrone compound have not yet been isolated from soybean miso. The structure of the novel 4-pyrone compound, 3-((E)-2-carboxyethenyl)-5-(4-hydroxyphenyl)-4-pyrone-2-carboxylic acid was elucidated by using the same compound as that obtained from the biotransformation of daidzein. 3 0 -Hydroxydaidzein showed as high DPPH radical-scavenging activity as that oftocopherol, and 6-hydroxydaidzein had mushroom tyrosinase inhibitory activity with an IC 50 value of 10 M. The order of estrogenic activity is as follows: genistein > daidzein 3 0 -hydroxydaidzein > 8-hydroxygenistein, using a green fluorescent protein expression system. Furthermore, the contents of isoflavones in the fermentation process of dou-chi were measured.
Isolation, Bioactivity, and Production of ortho-Hydroxydaidzein and ortho-Hydroxygenistein
Daidzein and genistein are two major components of soy isoflavones. They exist abundantly in plants and possess multiple bioactivities. In contrast, ortho-hydroxydaidzein (OHD) and ortho-hydroxygenistein (OHG), including 6-hydroxydaidzein (6-OHD), 8-hydroxydaidzein (8-OHD), 3'-hydroxydaidzein (3'-OHD), 6-hydroxygenistein (6-OHG), 8-hydroxygenistein (8-OHG), and 3'-hydroxygenistein (3'-OHG), are rarely found in plants. Instead, they are usually isolated from fermented soybean foods or microbial fermentation broth feeding with soybean meal. Accordingly, the bioactivity of OHD and OHG has been investigated less compared to that of soy isoflavones. Recently, OHD and OHG were produced by genetically engineering microorganisms through gene cloning of cytochrome P450 (CYP) enzyme systems. This success opens up bioactivity investigation and industrial applications of OHD and OHG in the future. This article reviews isolation of OHD and OHG from non-synthetic sources and production of the compounds by genetically modified microorganisms. Several bioactivities, such as anticancer and antimelanogenesis-related activities, of OHD and OHG, are also discussed.
Monatshefte für Chemie - Chemical Monthly, 2009
Matrix solid-phase dispersion (MSPD) extraction and HPLC have been used for determination of daidzein and genistein in Iranian soybean and its waste. For extraction of these compounds, the type of sorbent, the ratio of sorbent to sample, and the type and volume of elution solvent and its pH were studied. The best recoveries were obtained with a ratio 2:1 of silica gel to sample and 12 cm 3 methanol at pH 3. Optimized mobile phase composition for HPLC analysis of these compounds was u(H 2 O) = 0.45, u(MeOH) = 0.54, u(THF) = 0.01 adjusted to pH 4 by use of phosphate buffer. Limit of detection and linear dynamic range for daidzein and genistein were 0.016, 0.052, 0.016-132, and 0.052-146 lg/g. Recoveries of daidzein and genistein from soybean and its waste were 84-95%. Concentrations of daidzein in soybean and its waste were 39.1 and 22.2 lg/g, respectively; respective concentrations of genistein were 103.3 and 19.7 lg/g.
Efficient protocol for isolation and purification of different soyasaponins from soy hypocotyls
Journal of Separation Science, 2012
Soyasaponins are naturally occurring triterpenoid glycosides associated with many biological activities. The aim of the present study was to develop an effective method for isolation and purification of differently glycosylated, acetylated, and 2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP)-conjugated soyasaponins from soy hypocotyls. Both gel filtration using Sephadex LH-20 chromatography (Amersham Pharmacia Biotech AB; elution phase: methanol, flow rate: 3.0 mL/min, sample loading: 60 mg) and high-speed countercurrent chromatography (stationary phase: n-butanol-acetic acid (5.0%, v/v), mobile phase: water flow rate: 3.0 mL/min, sample loading: 100 mg) could effectively fractionate isoflavones and soyasaponins from the crude extract with yield of soyasaponin complexes 20.5 mg and 22.3 mg, respectively. After fractionation, the soyasaponin complexes could be purified further using preparative HPLC to separate individuals. A total of nine soyasaponins, triacetyl soyasaponin Ab (yield 1.55%, HPLC purity >98%), Aa (2.68%, >99%), Ab (18.53%, >98%), Ae (0.85%, >98%), Ba (0.63%, >91%), Af (1.12%, >85%), Bb (3.45%, >98%) and Be (0.59%, >76.8%) were obtained. DDMP-conjugated groups, ␣g (2.06%, >85%), g (7.59%, >85%), and ␥g (0.29%, >85%) that were very labile even in mild conditions, were also collected. The method described here can be used as an effective protocol to separate different soyasaponins occurring in the original sample.
Potential of local black soybean as a source of the isoflavones daidzein and genistein
2017
Daidzein and genistein are isoflavone compounds produced by soybean plants and have an important role in medical therapy. For the soybean crop itself, daidzein and genistein contribute as a defence mechanism against pathogen attack, and also as chemoattractants for Rhizobium bacteria. The development of black soybean varieties that have high levels of daidzein and genistein is required for functional food and industrial raw materials. The objective of this study was to identify the content of daidzein and genistein in local black soybean genotypes. Thirty-four black soybean genotypes were planted in a randomised block design. Daidzein and genistein content were measured in black soybean seeds using high-performance liquid chromatography. In the 34 black soybean genotypes, daidzein contents (0.01–0.21 mg g-1) were more variable than genistein (0.02–0.03 mg g-1). Compared to genistein, daidzein content was higher in 31 genotypes (0.03–0.21 mg g-1) and the other in three genotypes (0.0...
Majalah Kedokteran Bandung
Free radicals are known as a leading factor in aging. Nitric oxide (NO) and O 2 •-have been shown to inhibit the synthesis of matrix components and stimulate prolidase activities involved in collagen degradation. Hydroxyl (• OH) radical is a precursor of hyaluronic acid degradation. Antioxidants act as a scavenger for free radicals, creating a possibility to use them to prevent the aging process. Black soybeans (Glycine max (L.) Merr.) contain bioactive compounds that have the ability to scavenge free radicals, including daidzein. Daidzein belongs to the isoflavones group which is the most active compound in black soybean. This study aimed to understand the antioxidant activities of the black soybean extract (BSE) and daidzein compound in the scavenging of • OH and NO radicals and was performed at the Aretha Medika Utama-Biomolecular and Biomedical Research Center (BBRC), Bandung, Indonesia, from September to November 2018. The scavenging activity of • OH was assessed using the deoxyribose method, while the assessment of the scavenging of NO radicals was carried out using the sodium nitroprusside method. BSE and daidzein had an • OH scavenging activity with an IC50 value of 71.07 μg/mL, followed by daidzein with 24.57 μg/mL. A higher NO scavenging activity was seen in BSE with an IC50 of 71.60 μg/mL followed by daidzein with 35.68 μg/mL. Daidzein has a higher antioxidant activity through hydroxyl and nitric oxide scavenging compared to Glycine max (L.) Merr. extract. Hence, daidzein has a higher potential as an anti-aging agent based on the free-radical theory of aging.
BACKGROUND: The Maillard reaction indicators furosine, hydroxymethylfurfural (HMF), acrylamide and color were determined to evaluate heat effects induced during extrusion, infrared and microwave heating of soybean. In addition, the present paper aimed to study changes in the phenolic compounds, as well as in the overall antioxidant properties of different soybean products in relation to heating at 45-140 • C during the processes. RESULTS: Soybean proteins were highly sensible to Maillard reaction and furosine was rapidly formed under slight heating conditions during extrusion and infrared heating. Microwave heating at lower temperatures for a longer time yielded lower acrylamide levels in the final soybean products, as a result of its partial degradation. However, during infrared heating, acrylamide formation greatly increased with decreasing moisture content. After a short time of extrusion and infrared heating at 140 • C and microwave heating at 135 • C for 5 min, concentrations of HMF increased to 11.34, 26.21 and 34.97 µg g −1 , respectively.
Bulletin of University of Agricultural Sciences and Veterinary Medicine Cluj-Napoca. Agriculture, 1970
As research studies on lipoxygenase inhibition indicate quercetin as a one of the most potent inhibitors of this enzyme, this work presents our results concerning the inhibition of soybean lipoxygease-1 by pure quercetin. The spectra of the mixture lipoxygenase-1 and quercetin were performed by UV-Vis spectoscopy at the time t=0 min when the two components were mixed and after 60 min of incubation of those. For the experiments were used three quercetin concentrations, 10μM, 50μM and 100μM. The spectra show the formation of a new peak at λ~322 and a decrease in absorbance for peaks 1, λ~273, and 3, λ~395. This fact indicates the formation of a new compound as a result of this reaction. The formation of this new compound increases with the increase of the concentration of the inhibitor showing that that a greater concentration of quercetin determines a more intense interaction between lipoxygenase and inhibitor.
Powerful Antioxidants and Cytotoxic Activities of the Methanol Extracts from Eight Soybean Cultivars
Molecules
In the present study, the chemical composition and total phenolic (TPC) and total flavonoid contents (TFC) of eight soybean cultivars (Giza 21, Giza 22, Giza 35, Giza 111, Giza 82, Giza 83, Crawford, and Holliday) were estimated. Moreover, antioxidant activity and in vitro cytotoxic activities against HepG-2 and MCF-7 were evaluated. Giza 21, Giza 111, and Crawford cultivars recorded higher than 40% crude protein. The analysis revealed that TPC values in seed extracts ranged from 10.5 mg GAE/g extract in Giza 35 to 6.4 mg GAE/g extract in Giza 22. TFC varied from 1.20 mg QE/g extract in Giza 111 to 0.55 mg QE/g extract in Crawford. Giza 35 exhibited the highest content of genistein and daidzein and the highest free radical scavenging activity (61.833%). The results of the MTT assay demonstrated that the soybean methanolic extracts inhibited the proliferation of HepG-2 and MCF-7 cells in a dose-dependent manner. Giza 35 exhibited the highest cytotoxic activity. In conclusion, Giza 35...
Antioxidative Capacity of Soyfoods and Soy Active Compounds
Polish Journal of Food and Nutrition Sciences, 2022
Soyfood isoflavones and soyasaponins are effective compounds in terms of their health-promoting properties. Their chemical structure plays an important role in their antioxidative activity. Thus, six isoflavones and four soyasaponins that are targeted in soyfood were evaluated for their peroxyl radical scavenging capacities by the hydrophilic-oxygen radical absorbance capacity (H-ORAC) method. The antioxidant capacity of non-fermented and fermented soyfoods was also determined by the same method. The results revealed that isoflavones showed higher peroxyl radical scavenging capacities than soyasaponin, with their activities found to depend on their chemical structure. The aglycone isoflavones promoted higher H-ORAC values than glycoside and malonyl glycoside isoflavones, respectively. On the other hand, DDMP saponin promoted a higher H-ORAC value than its derived compound, group B saponin, and the aglycone soyasaponin. In the case of soyfoods, fermented soyfoods had higher antioxidative capacity that the non-fermented ones, especially the long-term fermented products. Soybean-koji miso presented the highest H-ORAC value, followed by natto, soy sauce, and tempeh. Moreover, lightness (L*) of miso and soy sauce showed a negative correlation with H-ORAC value probably due to browning substances which might derive from the amino-carbonyl reaction. Considering the high antioxidant capacity of fermented soyfoods, it might relate to aglycone isoflavones which promote strong radical scavenging capacity. Thus, fermented soyfoods, especially miso and natto, could be considered as health-promoting foods.