• Food Science of Animal Resources
• /
• v.27 no.3
• /
• pp.329-336
• /
• 2007

This study was designed to find the optimum conditions for converting isoflavone glycoside to aglycone by ${\beta}-galactosidase$. Three different forms of the enzyme were tested and the optimum enzyme concentration, incubation temperature, pH, and incubation time were determined. Before treatment with enzyme, isoflavone contained 89.4% glycoside including daidzin, glycitin and genistin, and only 10.6% aglycone including daidzein, glycitein and genistein. Among the enzymes tested, the highest rate of isoflavone hydrolysis to aglycone, 35%, was observed when 3 unit/g Fungal Lactase (Amano Enzyme) was used. Higher incubation temperatures resulted in a higher rate of hydrolysis along with a greater loss of isoflavone mass. Therefore, body temperature $(37^{\circ}C)$ may be adequate for isoflavone conversion, with 44.9% hydrolysis and less than 10% loss of mass. As expected, a higher amount of aglycone was produced at pH 7 compared with other pH values. During 5hr of incubation, the conversion of glycoside to aglycone increased dramatically from 0 to 1hr, and plateaued thereafter. In addition, commercial soy-based milk was hydrolyzed more effectively with ${\beta}-galactosidase$ when incubated for 5hr. Based on the above results, the optimum conditions for isoflavone hydrolysis by ${\beta}-galactosidase$ were for 3 hr at $37^{\circ}C$, pH 7 with 3 unit/g Fungal Lactase (Amano Lactase), yielding an average total amount of aglycone ranging from 40 to 47%.

• Journal of the Korean Chemical Society
• /
• v.34 no.5
• /
• pp.465-468
• /
• 1990

7-Deoxy-9-methyl aklavinones, the derivatives of aklavinone (the aglycone of extensive family of glycosidically derived from anthracycline antibiotics possessing significant activity), were synthesized by the simple and efficient reaction procedure.

• Environmental Mutagens and Carcinogens
• /
• v.19 no.2
• /
• pp.116-121
• /
• 1999

Quercetin and its glycosides showed a strong free radical scavenging effect to DPPH radical generation. However, there were not big differences between quercetin aglycone and glycosides under experimental condition of this study. On the other hand, quercetin had pro-oxidant effect in bleomycin-dependent DNA assay. Quercetin aglycone and its glycosides, quercitrin inhibited $H_2$$O_2$- induced DNA damage in CHL cells. They also have an anticlastogenicity toward DNA breakage agent by radical generation like bleomycin. These results indicate that quercetin aglycone and its glycosides are capable of protecting the free radical generation induced by reactive oxygen species like $H_2$$O_2$. The mechanism of inhibition in hydrogen peroxide-induced genotoxicity may be due to their free radical scavenging properties. Therefore, quercetin aglycone and its glycosides may be useful chemopreventive agents by protecting of free radical generation which are involved in carcinogenesis and aging. However, quercetin and its glycosides must also carefully examined for pro-oxidant properties before being proposed for use in vivo.

• Journal of the Society of Cosmetic Scientists of Korea
• /
• v.34 no.4
• /
• pp.259-268
• /
• 2008

In this study, the antioxidative effects, inhibitory effects on tyrosinase and elastase and components of Castanea crenata leaf were investigated. The free radical (1,1-diphenyl-2-picrylhydrazyl radical, DPPH) scavenging activity ($FSC_{50}$) of extract / fractions of Castanea crenata left was in the order: 50% ethanol extract ($13.6{\mu}g/mL$) < ethyl acetate fraction (6.2) < aglycone fraction (2.1). Reactive oxygen species (ROS) scavenging activities ($OSC_{50}$ of extract / fractions from Castanea crenata leaf extract / fractions on ROS generated in $Fe^{3+}$-EDTA/$H_2O_2$ system were investigated using the luminol-dependent chemiluminescence assay. The order of ROS scavenging activity was in the order: aglycone fraction (0.8) < 50% ethanol extract (0.5) < ethyl acetate fraction (0.3). The scavenging activity ($IC_{50}$ for ${O_2}^{{\cdot}\;-}$ (superoxide anion radical) generated by NBT method was in the order: ethyl acetate fraction (145.5) < aglycone fraction (65.5). The protective effects on the rose-bengal sensitized photohemolysis of human erythrocytes were investigated. The ethyl acetate fraction exhibited the most prominent cellular protective effect (${\tau}_{50}$, $191.9{\pm}12.2\;min$ at $10{\mu}g/mL$). The inhibitory effect of aglycone fraction ($9.1{\mu}g/mL$) on elastase was higher than oleanolic and ($13.7{\mu}g/mL$). And the inhibitory effect of aglycone fraction ($21.6{\mu}g/mL$) on tyrosinase was higher than arbutin ($226.2{\mu}g/mL$). But 50% ethanol extract rarely exhibited the inhibitory activity on tryosinase and elastase. Flavonoids were contained in Castanea crenata left (96.3 mg / 100 g dried Castanea crenata leaf). And flavonoids contained in ethyl acetate fraction were kaempferol, quercetin, quercitrin, and so on. Quercitrin is the most abundant component. These results indicate that extract / fractions of Castanea crenata can function as antioxidants in biological systems, particularly skin exposed to UV radiation by scavenging free radical and ROS, Castanea crenata leaf extract/ fractions could be used as new cosmeceutical for whitening and anti-wrinkle products.

• Journal of the Society of Cosmetic Scientists of Korea
• /
• v.37 no.2
• /
• pp.143-152
• /
• 2011

In this study, the antioxidative activity, inhibitory effects on tyrosinase and elastase, and active components of Quercus salicina Blume extracts were investigated. Q. salicina Blume was extracted using 50 % ethanol, from which ethyl acetate and aglycone fractions were prepared. The DPPH (1,1-diphenyl-2-picrylhydrazyl) scavenging activity ($FSC_{50}$) of Q. salicina Blume aglycone fraction was the highest ($8.25\;{\mu}g$/mL). The luminol-dependent chemiluminescence assay showed that reactive oxygen species (ROS) scavenging activities ($OSC_{50}$) of Q. salicina Blume aglycone fraction on ROS generated in $Fe^{3+}-EDTA/H_2O_2$ system was the most prominent at $0.039\;{\mu}g$/mL. The protective effects of extract/fractions of Q. salicina Blume against the rose-bengal sensitized photohemolysis of human erythrocytes were increased in a concentration dependent manner ($1{\sim} 25\;{\mu}g$/mL). Especially, ${\tau}_{50}$ of aglycone fraction in $10 \;{\mu}g$/mL concentration showed the most protective effect at 259.9 min. The inhibitory effects ($IC_{50}$) on tyrosinase and elastase of Q. salicina Blume extracts were higher at aglycone fraction (respectively, $21.82 \;{\mu}g$/mL, $41.18\;{\mu}g$/mL). Active component analysis by TLC and HPLC showed quercetin, keampferol, catechin, quercitrin, isoquercitrin, hyperoside, and etc. These results indicate that Q. salicina Blume extract has strong antioxidative activity and can be used as antioxidant. Particularly, aglycone fraction of Q. salicina Blume showed superior antioxdative activity and high inhibitory effect on tyrosinase and elastase. Therefore, aglycone fraction of Q. salicina Blume could be applicable to new functional cosmetics.

• Proceedings of the Korean Society for Food Science of Animal Resources Conference
• /
• 2004.10a
• /
• pp.371-374
• /
• 2004

본 연구는 식물성 에스트로겐인 isoflavone 배당체의 ${\beta}-1,4\;glycoside$ 결합을 ${\beta}-galactosidase$로 분해하여 그 생리적 작용이 더욱 효과적인 aglycone화 하기 위한 조건을 연구하여 기능성식품개발에 응용토록 하는데 목적이 있다. 실험 결과, 모든 ${\beta}-galactosidase$가 ${\beta}-1,4\;glycoside$ 결합의 분해력이 인정되지는 않았으며, 분해 가능성이 인정된 효소를 선택하여 실험한 결과 효소의 함량이 증가함에 따라 aglycone의 성분비율이 증대된 반면, 그 손실률 또한 증대되었고 배양시간이 길수록 aglycone의 성분비율이 증가하였으나 배양초기에 급격한 증가율을 보였으며, pH6과 7, 8에서 유사한 정도의 증가율을 보였고, 온도가 증가함에 따라 aglycone 성분비율이 증가되었지만 $40^{\circ}C$이상에서는 그 손실률이 크게 증가하였다. 결과적으로 판단해 볼 때, isoflavone을 aglycone화 하는데 있어 인체 내 유사조건에서 aglycone의 증가율이 높았으며 최적의 조건과 많은 차이를 나타내지 않았고 그 손실률 또한 최소화된 결과를 나타내어 isofalvone을 적용한 기능성 유제품을 연구하는데 있어 긍정적인 가능성을 보였다.

• Journal of Nutrition and Health
• /
• v.36 no.1
• /
• pp.32-39
• /
• 2003

Phytoestrogens, especially soy-derived isoflavones, are receiving great scrutiny as a food supplement for preventing hormone dependent disease such as postmenopausal osteoporosis. Their beneficial effects are derived from aglycone form of isoflavones, such as daidzein, genistein or glycitein. In contrast to the common usage of soybean, black bean (Rhynchosia Molubilis : Yak-kong) has been used as a supplement for preventing postmenopausal osteoporosis in oriental medicine. To investigate the effects of the saliva, artificial stomach fluid, and digestive enzymes on the conversion of glycosidic isoflavone to aglycone form, soybean and black bean were extracted with 70% methanol and freeze-dried. The recovery yield of methanol extracts of black bean was 14.1% which was higher than that of soybean, 13.5%. In terms of total isoflavones, we routinely obtained larger amount of isoflavones from black bean than those from soybean. By incubating methanol extracts of soybean and black bean with IN HCI for 180 min, the proportions of aglycones relative to the total isoflavone were significantly increased (32.4% and 52.4%, respectively). In vitro conversion, digestive enzymes ($\beta$-glucosidase and $\alpha$-glucosidase) may hydrolyze glycosidic bond of isoflavone more effectively than saliva or artificial stomach fluid did. It seems to say that the activity of $\beta$-glucosidase was higher than those of $\alpha$-glucosidase. The rate of conversion of glucoside form to aglycone form in black bean and soybean was low in physiological condition (pH) tested, although the enzymatic hydrolysis of glucoside was active. These results demonstrated that the composition of aglycone in food may be the important factors in terms of the bioavailability of isoflavones. (Korean J Nutrition 36(1): 32-39, 2003)

• Applied Biological Chemistry
• /
• v.40 no.6
• /
• pp.577-582
• /
• 1997

Effects of four citrus flavonoids, hesperidin, naringin and their aglycones on phosphatidate phosphohydrolase(PAP, EC 3.1.3.3) activity were examined using isolated rat microsomes as an enzyme source. In addition, these flavonoids were tested to see whether they exert any influence on the proliferation and growth in cultured human hepatocytes HepG2 cells. Flavonoids at concentration up to $10{-4}M$ had no significant effect on the number of cells and cell proliferation by MTT cell growth assay method, whereas aglycone flavonoids, hesperetin and narigenin, at concentration of $10{-3}M$ significantly inhibited cell proliferation. Hesperetin inhibited PAP activity in a dose-dependent manner starting at concentration of $10{-5}M$. Narigenin at concentration of $10{-2}M$ inhibited PAP activity markedly, while the other flavonoids did not show any significant effect. The present study, therefore, demonstrated that aglycone flavonoids exerted portent effects on PAP activity and on cell proliferation.

• Journal of the Society of Cosmetic Scientists of Korea
• /
• v.33 no.3
• /
• pp.145-152
• /
• 2007

In this study, the antioxidative effects of Sueada asparagoides and Salicornia herbacea extracts were investigated. The free radical(1,1-diphenyl-2-picrylhydrazyl, DPPH) scavenging activity($FSC_{50}$) of extract/fractions of Sueada asparagoides was in the order: 100 % ethanol extract(329.33 ${\mu}g/mL$) < 50 % ethanol extract(40.73) < ethylacetate fraction(13.87) < deglycosylated aglycone fraction (7.80). In case of Salicornia herbacea, the free radical scavenging activities of ethylacetate fraction and aglycone fraction were 13.87 and 7.80 ${\mu}g/mL$, respectively. Reactive oxygen species(ROS) scavenging activities($OSC_{50}$) of Sueada asparagoides and Solicornia herbacea extracts on ROS generated in $Fe^{3+}-EDTA/H_2O_2$ system were investigated using the luminol-dependent chemiluminescence assay. The order of ROS scavenging activity of Sueada asparagoides extracts was 50 % ethanol extract($OSC_{50}$, $0.99{\mu}g/mL$) < ethylacetate fraction (0.05) < aglycone fraction (0.03). Aglycone fraction showed the most prominent scavenging activity. In case of Salicornia herbacea, the ROS scavenging activities of ethylacetate fraction and aglycone fraction were 0.10 and 0.20 ${\mu}g/mL$, respectively. The protective effects of extract/fractions of Sueada asparagoides and Salicornia herbacea on the rose-bengal sensitized photohemolysis of human erythrocytes were investigated. The ethanol extract(100%) of Sueada asparagoides diminished photohemolysis in a concentration dependent manner($1{\sim}100{\mu}g/mL$). Particularly deglycosylated aglycone fraction exhibited the most prominent celluar protective effect($\tau_{50}$, 310 min at 50 ${\mu}g/mL$). In case of Salicornia herbacea, ethylacetate fraction exhibited more potent protective effect. These results indicate that extract/fractions of Sueada asparagoides can function as antioxidants in biological systems, particularly skin exposed to UV radiation by scavenging $^1O_2$ and other ROS, and protect cellular membranes against ROS.

• Journal of the Society of Cosmetic Scientists of Korea
• /
• v.34 no.4
• /
• pp.275-286
• /
• 2008

In this study, we investigated the anti-oxidative, anti-wrinkle and whitening effects of Platycarya strobilacea bark extracts. The free radical (1,1-diphenyl-2-picrylhydrazyl, DPPH) scavenging activity ($FSC_{50}$) of extract / fractions of Platycarya strobilacea was in the order: 50% ethanol extract ($6.75{\mu}g/mL$) < deglycosylated aglycone fraction ($6.62{\mu}g/mL$) < ethyl acetate fraction ($4.15{\mu}g/mL$). Reactive oxygen species (ROS) scavenging activities ($OSC_{50}$) of some Platycarya strobilacea extracts on ROS generated in $Fe^{3+}$-EDTA/$H_2O_2$ system were investigated using the luminol-dependent chemiluminescence assay. The order of ROS scavenging activity was ethyl acetate fraction (OSC50, $0.56{\mu}g/mL$) < 50% ethanol extract ($0.02{\mu}g/mL$) < deglycosylated aglycone fraction ($0.01{\mu}g/mL$). The deglycosylated aglycone fraction showed the most prominent scavenging activity. The protective effects of extract / fractions of Platycarya strobilacea on the rose-bengal sensitized photohemolysis of human erythrocytes were investigated. The ethanol extract (50%) suppressed photohemolysis in a concentration dependent manner, particularly ethyl acetate fraction exhibited the most prominent cellular protective effect (${\tau}_{50}$, 717.27 min at $10{\mu}g/mL$). The inhibitory effect of Platycarya strobilacea extracts on tyrosinase were investigated to assess their whitening efficacy. Finally, their anti-elastase activities were measured to predict the anti-wrinkle efficacy in the human skin. The inhibitory effect ($IC_{50}$) on tyrosinase of some Platycarya strobilacea extracts was 50% ethanol extract ($243.98{\mu}g/mL$) < ethyl acetate fraction ($153.87{\mu}g/mL$) < deglycosylated aglycone fraction ($137.53{\mu}g/mL$). Also, The inhibitory effect of elastase ($IC_{50}$) of some Platycarya strobilacea extracts was 50% ethanol extract ($31.01{\mu}g/mL$) < ethyl acetate fraction ($14.42{\mu}g/mL$) < deglycosylated aglycone fraction ($1.48{\mu}g/mL$). The cream containing the ethyl acetate fraction of Platycarya strobilacea extracts was formulated. The skin hydration, transepidermal water loss, and the whitening effects were investigated after topical application of the cream. The skin hydration of cream containing extract was increased by $2{\sim}8%$ than the placebo cream, transepidermal water loss was decreased. The cream containing extract suppressed the melanogenesis of skin by 9.55% than the placebo cream. These results indicate that extract / fractions of Platycarya strobilacea can function as antioxidants in biological systems, particularly skin exposed to UV radiation by anti-oxidative activity and protect cellular membranes against ROS. The inhibitory effect on elastase and tyrosinase, and the increase of skin hydration and the whitening effect of the cream containing extract could be applicable to new functional cosmetics for antiaging.