• Title/Summary/Keyword: aglycones

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Characteristics and Antioxidant Effect of Garlic in the Fermentation of Cheonggukjang by Bacillus amyloliquefaciens MJ1-4

  • Kim, Jeong Hwan;Hwang, Chung Eun;Lee, Chang Kwon;Lee, Jin Hwan;Kim, Gyoung Min;Jeong, Seong Hoon;Shin, Jeong Hee;Kim, Jong Sang;Cho, Kye Man
    • Journal of Microbiology and Biotechnology
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    • v.24 no.7
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    • pp.959-968
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    • 2014
  • The changes in the ${\beta}$-glucosidase activity, total phenolic contents, isoflavone contents, and antioxidant activities during the fermentation of cheonggukjang by Bacillus amyloliquefaciens MJ1-4 with and without garlic were investigated. The levels of total phenolic and isoflavone-malonylglycoside, -acetylglycoside, and -aglycone contents increased, whereas the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis (3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical scavenging activities and ferric reducing/antioxidant power (FRAP) assay results increased, but isoflavone-glycoside levels decreased during cheonggukjang fermentation. The levels of total phenolic and total isoflavone contents and the antioxidant activities were higher in cheonggukjang fermented without garlic (CFWOG) than in cheonggukjang fermented with garlic (CFWG) after 24 h of fermentation, but they were lower in CFWOG than in CFWG after 72 h of fermentation. In particular, the highest levels of total phenolic, daidzein, glycitein, and genistein were present at concentrations of 15.18 mg/g, $264.4{\mu}g/g$, $16.4{\mu}g/g$, and $31.1{\mu}g/g$ after 72 h of fermentation in CFWG, showing 82.89% in DPPH radical scavenging activity, 106.32% in ABTS radical scavenging activity, and 1.47 ($OD_{593nm}$) in FRAP assay, respectively. From these results, we suggest that the high antioxidant activity of CFWG might be related to the markedly higher levels of total phenolic contents, isoflavone-malonylglycosides, -acetylglycosides, and -aglycones achieved during fermentation.

Glycosidically Bound Volatile Components in Apricot (Prunus armeniaca var. ansu Max.) (살구에서 배당체의 형태로 존재하는 휘발성 성분)

  • Kim, Young-Hoi;Kim, Kun-Soo;Park, Joon-Young;Kim, Yong-Tae
    • Korean Journal of Food Science and Technology
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    • v.22 no.5
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    • pp.549-554
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    • 1990
  • Glycosidically bound fraction was separated from apricot by Amberlite XAD-2 adsorption and eluted with methanol. Aglycones were liberated from the bound fraction by enzymatic hydrolysis, acid hydrolysis or by means of simultaneous distillation-extraction at pH 3.0. A total of 40 components were identified in three bound volatile fractions. Besides linalool oxide, linalool. ${\alpha}-terpineol$, nerol, geraniol, benzyl alcohol and 2-phenylethyl alcohol, previously reported as glycosidically bound volatiles, the following components were identified for the first time as glycosidically bound volatiles in apricot: 2,6-dimethyl-3,7-octadiene-2,6-diol , 3.7-dimethyl-1,5-octadiene-3,7-diol, (E)- and (Z)-2.6-dimethyl-2,7-octadiene-1,6-diol, $3,4-didehydro-{\beta}-ionol,\;3-oxo-{\alpha}-ionol$, $3-hydroxy-7,8-dihydro-{\beta}-ionol,\;3-oxo-7,8-dihydro-{\alpha}-ionol ,\;3-hydroxy-{\beta}-ionone$, eugenol, 4-hydroxyethylphenyl acetate and 2,3-dihydrobenzofuran.

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Recovery of Isoflavones from Soybean Cooking Water Produced during Soymilk Manufacturing Process (두유 제조 공정에서 생산되는 대두 침지액으로부터 이소플라본의 회수)

  • Choi, Yeon-Bae;Sohn, Heon-Soo
    • Korean Journal of Food Science and Technology
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    • v.29 no.3
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    • pp.522-526
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    • 1997
  • Soy isoflavones could be recovered with adsorption resin column chromatography from soybean cooking water produced during soymilk or tofu manufacturing process. The main isoflavones in the soybean cooking water were genistin and daidzin, and their concentration was $0.083{\pm}0.019$ and $0.11{\pm}0.017\;mM$, respectively. Their aglycones were not detected. pH of soybean cooking water was critical in this chromatographic process and the recovery of isoflavones, both genistin and daidzin, was maximum at pH 4.0. Adsorption of genistin on the resin was stronger than that of daidzin. Elution rate and height/diameter ratio also affected the recovery yield. Under the optimal conditions, about 85% of genistin and 70% of daidzin could be isolated from soybean cooking water. Soy saponins were also recovered with isoflavones.

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Alteration of Panax ginseng saponin composition by overexpression and RNA interference of the protopanaxadiol 6-hydroxylase gene (CYP716A53v2)

  • Park, Seong-Bum;Chun, Ju-Hyeon;Ban, Yong-Wook;Han, Jung Yeon;Choi, Yong Eui
    • Journal of Ginseng Research
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    • v.40 no.1
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    • pp.47-54
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    • 2016
  • Background: The roots of Panax ginseng contain noble tetracyclic triterpenoid saponins derived from dammarenediol-II. Dammarene-type ginsenosides are classified into the protopanaxadiol (PPD) and protopanaxatriol (PPT) groups based on their triterpene aglycone structures. Two cytochrome P450 (CYP) genes (CYP716A47 and CYP716A53v2) are critical for the production of PPD and PPT aglycones, respectively. CYP716A53v2 is a protopanaxadiol 6-hydroxylase that catalyzes PPT production from PPD in P. ginseng. Methods: We constructed transgenic P. ginseng lines overexpressing or silencing (via RNA interference) the CYP716A53v2 gene and analyzed changes in their ginsenoside profiles. Result: Overexpression of CYP716A53v2 led to increased accumulation of CYP716A53v2 mRNA in all transgenic roots compared to nontransgenic roots. Conversely, silencing of CYP716A53v2 mRNA in RNAi transgenic roots resulted in reduced CYP716A53v2 transcription. HPLC analysis revealed that transgenic roots overexpressing CYP716A53v2 contained higher levels of PPT-group ginsenosides ($Rg_1$, Re, and Rf) but lower levels of PPD-group ginsenosides (Rb1, Rc, $Rb_2$, and Rd). By contrast, RNAi transgenic roots contained lower levels of PPT-group compounds and higher levels of PPD-group compounds. Conclusion: The production of PPD- and PPT-group ginsenosides can be altered by changing the expression of CYP716A53v2 in transgenic P. ginseng. The biological activities of PPD-group ginsenosides are known to differ from those of the PPT group. Thus, increasing or decreasing the levels of PPT-group ginsenosides in transgenic P. ginseng may yield new medicinal uses for transgenic P. ginseng.

Bioconversion of Isoflavones and the Probiotic Properties of the Electroporated Parent and Subsequent Three Subcultures of Lactobacillus fermentum BT 8219 in Biotin-Soymilk

  • Ewe, Joo-Ann;Wan-Abdullah, Wan-Nadiah;Alias, Abdul Karim;Liong, Min-Tze
    • Journal of Microbiology and Biotechnology
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    • v.22 no.7
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    • pp.947-959
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    • 2012
  • This study was aimed at an evaluation of the potential inheritance of electroporation effects on Lactobacillus fermentum BT 8219 through to three subsequent subcultures, based on their growth, isoflavone bioconversion activities, and probiotic properties, in biotin-supplemented soymilk. Electroporation was seen to cause cell death immediately after treatment, followed by higher growth than the control during fermentation in biotin-soymilk (P<0.05). This was associated with enhanced intracellular and extracellular ${\beta}$-glucosidase specific activity, leading to increased bioconversion of isoflavone glucosides to aglycones (P<0.05). The growing characteristics, enzyme, and isoflavone bioconversion activities of the first, second, and third subcultures of treated cells in biotin-soymilk were similar to the control (P>0.05). Electroporation affected the probiotic properties of parent L. fermentum BT 8219, by reducing its tolerance towards acid (pH 2) and bile, lowering its inhibitory activities against selected pathogens, and reducing its ability for adhesion, when compared with the control (P<0.05). The first, second, and third subcultures of the treated cells showed comparable traits with that of the control (P>0.05), with the exception of their bile tolerance ability, which was inherited to the treated cells of the first and second subcultures (P<0.05). Our results suggest that electroporation could be used to increase the bioactivity of biotin-soymilk via fermentation with probiotic L. fermentum BT 8219, with a view towards the development of functional foods.

Biotransformation of flavonoid-7-O-glucuronides by $\beta$-glucuronidases

  • Choi, Ran-Joo;Ha, In-Jin;Choi, Jae-Sue;Park, You-Mie;Kim, Yeong-Shik
    • Natural Product Sciences
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    • v.16 no.1
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    • pp.1-5
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    • 2010
  • $\beta$-Glucuronidases (E.C. 3.2.1.31) from Escherichia coli, Helix pomatia, and bovine liver activity have been investigated on 7-O-glucuronides (baicalin, wogonoside, and luteolin-7-O-glucuronide) and 3-O-glucuronides (quercetin-3-O-glucuronide and kaempferol-3-O-glucuronide). Bovine liver enzyme was not active on any of these substrates. E. coli and H. pomatia enzymes were active on 7-O-glucuronides, however, 3-O-glucuronides were resistant to $\beta$-glucuronidase hydrolysis. These results suggest that glucuronic acid at 7-position is more susceptible to E. coli and H. pomatia $\beta$-glucuronidases than that at 3-position. In addition, the subtle difference of aglycone structure on 7-O-glucuronides affected the preference of enzyme. E. coli enzyme was favorable for the hydrolysis of baicalin, however, H. pomatia enzyme was found to be efficient for the hydrolysis of wogonoside. Both enzymes showed the similar hydrolytic activity towards luteolin-7-O-glucuronide. When the Scutellaria baicalensis crude extract was subjected to enzymatic hydrolysis, baicalin and wogonoside were successfully converted to their aglycone counterparts with H. pomatia at 50 mM sodium bicarbonate buffer pH 4.0. Accordingly, the enzymatic transformation of glycosides may be quite useful in preparing aglycones under mild conditions.

Phenolic Acids and Antioxidant Activities of Wild Ginseng (Panax ginseng C. A. Meyer) Leaves

  • Seog, Ho-Moon;Jung, Chang-Hwa;Kim, Yoon-Sook;Park, Hyeon-Suk
    • Food Science and Biotechnology
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    • v.14 no.3
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    • pp.371-374
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    • 2005
  • The compositions and antioxidant activities of tree and hydrolyzed phenolic acids, which are aglycones of esterified phenolic acids, in wild ginseng leaves were investigated. The contents of tree and hydrolyzed phenolic acids in the wild ginseng leaves were $422.4\;{\pm}\;3.5$ and $319.6\;{\pm}\;5.7\;mg/100\;g$, respectively, as gallic acid equivalents. Free phenolic acids were composed of 55.3% benzoic acid derivatives and 44.6% phenylpropanoids. The major constituents of free phenolic acids in the ginseng leaves were syringic (139.4 mg/l00 g) and sinapic (131.2 mg/100 g) acids. On the other hand, hydrolyzed phenolic acids in the ginseng leaves were mainly composed of caffeic (59.4 mg/100 g), ferulic (49.5 mg/100 g), and p-coumaric (33.8 mg/100g) acids. Phenylpropanoid content was higher (82.7%) than benzoic acid derivatives (17.3%). $IC_{50}$ values of DPPH radical scavenging activity were $10.2\;{\mu}g/mL$ for tree phenolic acids and 8.0 mg/mL for hydrolyzed phenolic acids, as gallic acid equivalents. Hydrolyzed phenolic acids also exhibited higher hydroxyl and superoxide radical scavenging activities than free phenolic acids did. These results indicated that the antioxidant activities of the wild ginseng leaves were correlated more closely with phenylpropanoid contents than with total amount of phenolics.

The Action of Triterpenoidal Glycosides of Dammarane Series and Their Aglycones on $K^{+}$ and $H^{-}$ Fluxes in Erythrocytes, Induced by lonophore $A_{23187}$ and Divalent ions ($A_{23187}$과 2가 이온에 의해 일어나는 $K^{+}$ 이온과 $H^{-}$ 이온의 흐름에 미치는 Triterpenoidal Dammarane Serids의 Glycosides와 그 Aglycones의 영향)

  • Kim, Yu.A.;Park, Kyeong-Mee;Kyung, Jong-Su;Hyun, Hak-Chul;Song, Yong-Bum;Shin, Han-Jae;Park, Hwa-Jin
    • Journal of Ginseng Research
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    • v.20 no.2
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    • pp.168-172
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    • 1996
  • Ginsenoside Rb,, at a concentration of 10 $\mu\textrm{g}$/ml and over, initiated the cycle of oscillation of ion flux in erythrocytes after the cells had been treated with a protonophore, carbonyl cyanide p-trifluoro-methoxyphenyl hydrazone (FCCP) and then with a $Ca^{2+}$ ionophore, A23,3,. Its action was similar to the additional portion of $Ca^{2+}$-ionophore or $Ca^{2+}$ ion to the erythrocytes. Effects of $Rg_1$ and Rf were different from that of Rb,. They did not induce the oscillation. They, however, increased the extracellular $K^{+}$ concentration and pH without returning to the initial state in the erythrocytes processed with FCCP and $A_{23187}$. We established that ginsenosides from 20-(5)-panaxatriol family induced the membrane hyperpolarization in erythrocytes, which was attenuated by the pretreatment of $Rb_1$, a major component of 20-(5)-panaxadiol.

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Quantitative aspects of the hydrolysis of ginseng saponins: Application in HPLC-MS analysis of herbal products

  • Abashev, Mikhail;Stekolshchikova, Elena;Stavrianidi, Andrey
    • Journal of Ginseng Research
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    • v.45 no.2
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    • pp.246-253
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    • 2021
  • Background: Ginseng is one of the most valuable herbal supplements. It is challenging to perform quality control of ginseng products due to the diversity of bioactive saponins in their composition. Acid or alkaline hydrolysis is often used for the structural elucidation of these saponins and sugars in their side chains. Complete transformation of the original ginsenosides into their aglycones during the hydrolysis is one of the ways to determine a total saponin group content. The main hurdle of this approach is the formation of various by-products that was reported by many authors. Methods: Separate HPLC assessment of the total protopanaxadiol, protopanaxatriol and ocotillol ginsenoside contents is a viable alternative to the determination of characteristic biomarkers of these saponin groups, such as ginsenoside Rf and pseudoginsenoside F11, which are commonly used for authentication of P. ginseng Meyer and P. quinquefolius L. samples respectively. Moreover, total ginsenoside content is an ideal aggregated parameter for standardization and quality control of ginseng-based medicines, because it can be directly applied for saponin dosage calculation. Results: Different hydrolysis conditions were tested to develop accurate quantification method for the elucidation of total ginsenoside contents in herbal products. Linearity, limits of quantification, limits of detection, accuracy and precision were evaluated for the developed HPLC-MS method. Conclusion: Alkaline hydrolysis results in fewer by-products than sugar elimination in acidic conditions. An equimolar response, as a key parameter for quantification, was established for several major ginsenosides. The developed approach has shown acceptable results in the analysis of several different herbal products.

Changes of Chemical Constituents of Rehmannia Radix during 'Steaming and Drying' Process (증폭(蒸曝)에 의한 지황(地黃)의 성분 변화에 대한 고찰)

  • Jung, Jae woo;Kim, Han young;Lyu, Ji hyo;Kim, Jung-Hoon
    • The Korea Journal of Herbology
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    • v.36 no.6
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    • pp.47-61
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    • 2021
  • Objectives : 'Steaming and drying' is a traditional processing method that has been used to produce Suk-ji-hwang (熟地黃; Rehmanniae Radix Preparata) from Ji-hwang (地黃, the fresh root of Rehmannia glutinosa Liboschitz ex Steudel; Rehmanniae Radix). The steaming and drying process, which is proceeded in heating and moisturizing conditions, plays a crucial role in the change of therapeutic effect of Ji-hwang, presumably due to the modification of its chemical constituents. In this article, the chemical influence of the 'Steaming and drying' process was investigated for understanding the underlying mechanism of chemical modification of Ji-hwang. Methods : The articles regarding the modifications of chemical constituents of Ji-hwang during the 'Steaming and drying' process were collected and analyzed to investigate the influence of the processing to Ji-hwang. Results : The results indicated that iridoid glycosides were degraded to their aglycones and sugars, and such degradations occurred faster at a high pressure than at an atmospheric pressure during the process. The contents of catalpol, ajugol, and acteoside were decreased, while those of rehmannioside A and D were slightly increased during the repeated processing. The contents of oligosaccharides, namely sucrose, maltose, raffinose, and stachyose (except for manninotriose), were decreased, while those of monosaccharides, glucose and fructose, were increased by the repeated processing. Conclusions : These results demonstrate that the 'Steaming and drying' process influenced the chemical constituents of Ji-hwang and provide probable basis for the therapeutic modification of Suk-ji-hwang after the processing of Ji-hwang.