• Journal of Life Science
• /
• v.22 no.6
• /
• pp.760-771
• /
• 2012

Marine triterpene glycosides are physiologically active natural compounds isolated from sea cucumbers(holothurians). It was demonstrated that they have a wide range of biological activities, including antifungal, cytotoxic, and antitumor effects. A previous study showed that stichoposide C (STC) isolated from Thelenota anax induces apoptosis through generation of ceramide by activation of acid sphingomyelinase (SMase) and neutral SMase in human leukemia cells. In this study, we investigated whether STD, a structural analog of STC, can induce apoptosis and examined the molecular mechanisms for its activity. It was found that STC and STD induce apoptosis in a dose- and time-dependent manner and lead to the activation of caspase-8, mitochondrial damage, activation of caspase-9, and activation of caspase-3 in K562 and HL-60 cells. STC activates acid SMase and neutral SMase, which results in the generation of ceramide. Specific inhibition of acid SMase or neutral SMase partially blocked STC-induced apoptosis, but not STD-induced apoptosis. In contrast, STD generates ceramide through the activation of ceramide synthase. Specific inhibition of ceramide synthase partially blocked STD-induced apoptosis, but not STC-induced apoptosis. Moreover, STC and STD markedly reduced tumor growth of HL-60 xenograft tumors and increased ceramide generation in vivo. These results indicate that STC and STD can induce apoptosis and have antitumor activity through the different molecular mechanisms, because they have a different sugar residue attached to aglycones. Thus, these results suggest that their actions are affected by a sugar residue attached to aglycones and they can be used as anticancer agents in the treatment of leukemia.

• Food Science and Preservation
• /
• v.30 no.6
• /
• pp.1012-1028
• /
• 2023

The findings of this study confirmed the alteration of β-glucosidase activity, nutritional constituents, isoflavones, antioxidant activities, and digestive enzyme inhibition activities in soybeans during solid-state fermentation times with mycelia of Tricholoma matsutake. After nine days, the highest activity level was observed for β-glucosidase (3.90 to 38.89 unit/g) and aglycones (163.03 to 1,074.28 ㎍/g). The sum of isoflavones showed a significant decrease (3,489.41 to 1,325.66 ㎍/g) along with glycosides (2,753.87 to 212.43 ㎍/g) for fermentation, while fatty acids showed a slight increase and amino acids showed a marked increase. Total phenolic and flavonoid contents showed a corresponding increase according to fermentation times (5.58 to 15.09 GAE mg/g; 0.36 to 1.58 RE mg/g). Antioxidant and enzyme inhibition activities also increased; in particular, the highest level of scavenging activities was observed for ABTS (up 60.13 to 82.08%), followed by DPPH (up 63.92% to 71.98%) and hydroxyl (up 36.01 to 52.02%) radicals. Of particular interest, α-glucosidase (6.69 to 83.49%) and pancreatic lipase inhibition (1.22 to 77.43%) showed a marked increase. These results demonstrated that fermentation of soybeans with the mycelia of T. matsutake enhanced the nutritional and functional constituents, and the biological activities of soybeans. Thus, this fermentation technology can be used to produce a novel functional materials from soybeans.

• Journal of the Society of Cosmetic Scientists of Korea
• /
• v.37 no.4
• /
• pp.351-356
• /
• 2011

Citrus unshiu (C. unshiu) Markovich were dried peel of mandarin orange, of which fresh fruit was one of the famous foods in Korea and Eastern Asia. In the oriental medicine, C. unshiu peel was known to have a diuretic effect and to strengthen spleen function. Recently, natural flavonoids of C. unshiu peel have been investigated. In this study, C. unshiu peel extract containing flavonoid-glycosides was cultured with Schizophyllum commune (S. commune) mycelia producing ${\beta}$-glu- cosidase and its biological activities were investigated. ${\beta}$-glucosidase of S. commune mycelia converted the flavonoid-glycosides (rutin and hesperidin) into aglycones (naringenin and hesperetin). Fermented C. unshiu peel extract compounds were analyzed by HPLC system. The photoprotective potential of fermented C. unshiu peel extract was tested in human dermal fibroblasts (HDFs) exposed to UVA. Fermented C. unshiu peel extract extract also showed notable in vitro anti-inflammatory effect on cellular systems generating cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) metabolites. Also, UVB-induced production of interleukin-$1{\alpha}$ in human HaCaT cells was reduced in a dose-dependent manner by treatment with fermented C. unshiu peel extract. These results suggest that fermented C. unshiu peel extract may mitigate the effects of photoaging in skin by reducing UV-induced adverse skin reaction.

• Korean Journal of Microbiology
• /
• v.49 no.4
• /
• pp.391-397
• /
• 2013

Changes in ${\beta}$-glycosidase activity, total phenolic and isoflavone contents, and antioxidant activities during the fermentation of Korean black soybeans (Seoritae and Seomoktae) fermented food cheonggukjang by the potential probiotic Bacillus subtilis CSY191 were investigated. The levels of total phenolic and isoflavone-malonylglycoside and -aglycone contents increased, while 2,2-azinobis (3-ethyl-benzothiazoline-6-sulfonic acid) diammonium salt (ABTS) radical scavenging activity and ferric reducing/antioxidant power (FRAP) increased, but the isoflavone-glycoside contents decreased after cheonggukjang fermentation. The content of antioxidant compounds, including isoflavone-aglycones and -malonylglycosides, was increased by fermenting-processing, whereas the content of isoflavone-glycosides was decreased in the fermented soybeans. In particular, the Seoritae soybean fermented at 3 $7^{\circ}C$ for 48 h displayed the highest antioxidant activities, compared to those of the Seomoktae soybean and the fermented. The highest levels of daidzein, glycitein, and genistein were present at concentrations of 253.0 ${\mu}g/g$, 72.5 ${\mu}g/g$, and 114.1 ${\mu}g/g$ after 48 h of Seoritae soybean fermentation. From those results, we suggest that the high antioxidant activity of cheonggukjang of black soybeans might be related to the markedly higher levels of total phenolic and isoflavone-aglycone and -malonylglycoside contents achieved during fermentation.

• Korean Journal of Food Science and Technology
• /
• v.50 no.4
• /
• pp.391-399
• /
• 2018

Bioconversion and fermentation of onion extract by lactic acid bacteria were carried out to enhance the bioavailability of quercetin through the increase of quercetin recovery and aglycone formation. Lactobacillus casei, L. plantarum, and Kluyveromyces lactis were selected as the optimum strains for bioconversion. The environmental conditions to maximize the conversion ratio between glycoconjugate and quercetin aglycone have been evaluated. The concentrations of quercetin after fermentation of onion slurry by K. lactis and L. casei increased to 260% and 318%, respectively; however, the quercetin concentrations decreased after 48 hours of fermentation. Additionally, the quercetin hexose concentration increased to almost 141%. Controlling the initial pH of the onion juice increased the lactic acid production by L. casei and L. plantarum by more than two-fold. Meanwhile, the concentration of quercetin hexose decreased rapidly with the increased production of aglycones. The scale-up experiments showed the same fermentation efficiency; however, thermal sterilization reduced the quercetin glycone concentrations drastically.

• Horticultural Science & Technology
• /
• v.29 no.4
• /
• pp.374-381
• /
• 2011

Stilbenes are polyphenolic natural products, which have antioxidative and antifungal activities. In some plants, including grapevine, the stilbene compounds, as resveratrol derivatives, exist in very diverse forms. Experiments to identify the individual stilbene compounds were carried out first to quantify them in UV-irradiated grapevine leaves. For this, stilbene glycosides were extracted from grapevine leaves which irradiated intensively with UV light. The glycoside samples were hydrolyzed by ${\beta}$-glucosidase, before analyzed by HPLC-mass spectrometer at each m/z corresponding to the mass of specific stilbenes. As results, in chromatograms, the enzymatic hydrolysis resulted in decrease and increase of the peaks expected for glycosides and aglycones, respectively. The samples were also exposed to sunlight in order to photo-isomerize the stilbene compounds. The light exposure resulted in disappearance and appearance of peaks expected for trans- and cis-isomers of stilbenes, respectively. Such a change of the peaks in chromatograms provided information needed for the inference to peak components. In this way, it was possible to identify 16 kinds of stilbene compounds from grapevine leaves. The identified stilbenes were quantified from grapevine leaves irradiated mildly by UV light. The UV-irradiation increased markedly in the content of stilbene compounds, especially trans-resveratrol by several hundredfold. In addition, piceatannol, which is a mere minor component of stilbenes in control leaves and a more active radical scavenger than resveratrol, was also increased by several tenfold by the treatment. The increase in stilbene contents as influenced by UV irradiation seems to be one of the stress coping responses of grapevine as a hormesis phenomenon.

• Korean Journal of Food Science and Technology
• /
• v.31 no.1
• /
• pp.189-195
• /
• 1999

Isoflavones of soy milk were mainly present as sugar conjugates such as genistin and daidzin which a glucosyl residue was attached to their aglycones, genistein and daidzein through ${\beta}-glycosidic$ bond, respectively. When soy milk containing sucrose as a sugar source was fermented with lactic acid bacteria, small amount of lactic acid $(0.16{\sim}0.29%)$ was produced but isoflavone conjugates were fully hydrolyzed. Supplementation of glucose or lactose was required for normal lactic acid production and affected the hydrolysis of isoflavone conjugates in some lactic acid bacteria. In the case of Lactobacillus delbrueckii subsp. delbrueckii KCTC 1047, glycosidic bond of isoflavone was fully hydrolyzed regardless of glucose supplementation. But only $25{\sim}40%$ of daidzin and $65{\sim}80%$ of genistin was hydrolyzed when glucose was added into soy milk in the other lactic acid bacteria, Lactobacillus bulgaricus KCTC 3188, Lactobacillus casei KCTC 3109, Lactobacillus delbrueckii subsp lactis KCTC 1058, Lactobacillus lactis KCTC 2181. The hydrolyzing enzyme, ${\beta}-glucosidase$ produced by lactic acid bacteria except Lactobacillus delbrueckii subsp. delbrueckii KCTC 1047 could be considered as inducible in the fermentation of soy milk and its production was decreased when glucose was added.

• KOREAN JOURNAL OF CROP SCIENCE
• /
• v.50 no.4
• /
• pp.291-300
• /
• 2005

This study was focuses on the variation of isoflavone contents during seed development and their interaction with major chemical components such as protein, amino acids, saccaharides, lipid and fatty acids. During maturing, lipid, protein, and amino acid contents in soybean seeds showed the highest values at R7 stages, but isoflavone contents were increased until R8 stage. It was noted that malonyl glucosides $(64.2\%)$ are predominant forms among conjugated isoflavones followed by glucosides $(30.7\%)$, acetyl glucosides $(4.1\%)$ and aglycones $(0.9\%)$. Sucrose and stachyose were presented as a major saccharide in soybean seeds. As maturing days progressed, they were constantly increased and the highest contents were observed at R8 stage. While small quantities of raffinose, fructose, glucose, maltose, DP3 (DP: degree of polymerization), DP6, and DP7 were detected. These results showed that saccharide composition at the beginning of seed development is primarily monosaccharides with little sucrose and oligosaccharides, but as maturing days proceeds, sucrose and starch increase with concomitant decrease in monosaccharides. Sucrose and stachyose were positively correlated with isoflavone (r=0.780, 0.764 at p<0.01, respectively), while fructose, glucose, maltose, and DP7 were negatively correlated (r=-0.651, -0.653, -0.602, and -0.586 at p<0.05, respectively). Soybeans at R8 stage were high in protein and amino acid, but low in free amino acid contents. Protein and amino acid contents showed positively significant correlations with isoflavone (r=0.571 and 0.599 at p<0.05, respectively), but free amino acid content were negatively correlation with isoflavone (r=-0.673, p<0.01). The lipid content reaches its final content relatively early stage of seed development and remains constant as compared with other chemical components. Among the fatty acids, although varietal difference was presented, stearic acid and linolenic acid were gradually decreased, while oleic and linoleic acid were increased as seed maturing progressed. Lipid was significantly correlated (r=0.754, p<0.01) with isoflavones. However, neither saturated fatty acid nor unsaturated fatty acids significantly affected the isoflavone contents of maturing soybean seeds.

• KOREAN JOURNAL OF CROP SCIENCE
• /
• v.65 no.2
• /
• pp.84-92
• /
• 2020

For humans, soybean and soybean products are the main dietary sources of isoflvones, which are polyphenolic compounds that represent one of the most common categories of phytoestrogens. The objective of this study was to determine isoflavone concentrations in soybean cultivars during germination when treated with some biotic substances. Three soybean cultivars were germinated in replicated trials in 2018/2019 and their individual and total isoflavone concentrations were determined using HPLC (High-Performance Liquid Chromatography). Significant differences were observed in total isoflavone content were observed among cultivars regardless of years and treatments. 'Daepung2-ho' and 'Uram' had significantly higher total isoflavones than 'Pungsannaul-kong'. Differences among treatments were also significant for total isoflavone content. In 2018, with chitosan treatment, total isoflavone concentration ranged from 551.15 to 7584.07 ㎍ g^-1, with an average of 2972.64 ㎍ g^-1 across cultivars. In 2019, there was no significant difference among treatments in total isoflavone content. Regarding individual isoflavone concentrations, the malonyl-glucoside groups accounted for over 85% of the total isoflavone content, which is indicated that these groups play an important role with regard to isoflavone components in soybean seeds. The individual proportions in the total concentrations of isoflavones varied according to germination period and seed tissues. Glucosides and malonyl-glucosides showed differences in concentrations among seed tissues, aglycones were further accumulated as germination period was progressed. This study suggests that biotic substances have an impact on seed isoflavone content during germination. However, cultivars with consistently high or low isoflavone concentrations across biotic substance treatments were identified desspite differences in germination period and seed tissues, demonstrating that the genetic factor plays the most important role in isoflavone accumulation.

• Microbiology and Biotechnology Letters
• /
• v.44 no.3
• /
• pp.317-323
• /
• 2016

An isoflavone glucosidase that catalyzes the hydrolysis of isoflavone glucosides into glucose and corresponding aglycones was purified from Candida fermentati SI. The N-terminal sequence was determined to be GLNCDYCN. We designed degenerate primers on the basis of these amino acid sequences and successfully cloned the full structural gene sequence of the isoflavone glucosidase using inverse PCR. The exo-β-(1,3)-glucanase gene consists of 1227 base-pair nucleotides, encoding a 408-amino-acid sequence that shares 41–96% amino acid homology with other yeast exo-β-(1,3)-glucanases belonging to glycoside hydrolase family 5. The recombinant exo-β-(1,3)-glucanase was expressed in Pichia pastoris X-33, using a pPICZA vector system, and further characterized. The molecular mass of the purified exo-β-(1,3)-glucanase was estimated by SDS-PAGE to be 47 kDa. The optimal pH and temperature were pH 4.5 and 40℃, respectively. The K_m values of the purified exo-β-(1,3)-glucanase for daidzin and genistin were 0.12 mM and 0.14 mM, respectively. The V_max values of the purified isoflavone glucosidase were 945.03 U/mg for daidzin and 835.92 U/mg and for genistin.