• YAKHAK HOEJI
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• v.34 no.5
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• pp.348-364
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• 1990

The activities of twenty-one flavonoids and their related compounds on the hypersensitivity reaction against various antigens were studied in vitro and in vivo. 1. Generally flavonoids inhibited significantly the homologous passive cutaneous anaphylaxis (PCA) induced by reaginic antibody as compared as anaphylaxis by compound 48/80-induced mast cell degranulation, and so more strongly active in the IgE-mediated anaphylaxis than non-IgE-mediated anaphylaxis. 2. Flavonids inhibited remarkably Arths reaction, hemolysin titer, delayed hypersensitivity, haemagglutinin titer, rosette forming cells and plague forming cells against sheep red blood cells, and so it exhibited that flavonoids inhibited type 2, 3 and 4 hypersensitivity. 3. Quercetin, kaempferol, hesperetin, disodium cromoglycate, malvin and baicalein were active dose-dependently in the all types of hypersensitivity. Fisetin, daidzein, morin, narigin, flavone, catechin, rutin, hesperidin, neophsperidin, apigenin and chrysin were significantly active in the various types of hypersensitivity, but apigenin, rutin and catechin were less active in the delayed hypersensitivity. Taxifolin was significantly active in PCA and histamine-induced anaphylaxis except other types of hypersensitivity. Rotenone and cyanin also inhibited all types of hypersensitivity, but they are toxic. 4. Based on these results from hypersensitivity, the following flavonoid structure-activity relationships became apparent. 1) Flavonoids with $C_{2-3}$ double bond in C-ring were more active than that of $C_{2-3}$ saturation. 2) Flavonoids with $C_4$ ketone group in C-ring were more active than abscence of them except catechin and malvin. 3) Flavonoids with benzene ring at positions 2 or 3 in C-ring exhibited same activities. 4) Flavonoids with opening of the C-ring does not abolish their activities. 5) The glycosylated flavonoids in position 3 or 7 was less active than their aglycone. 6) Flavonoids with the more hydroxy group in A and B-ring were more active. 7) Flavonoids with or without $C_3-OH$ did not change their activities.

• Archives of Pharmacal Research
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• v.26 no.10
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• pp.809-815
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• 2003

Since reactive oxygen species (ROS) and hydroxyl radicals ($^-OH$) play an important role in the pathogenesis of many human degenerative diseases, much attention has focused on the development of safe and effective antioxidants. Preliminary experiments have revealed that the methanol (MeOH) extract of the stem of Prunus davidiana exerts inhibitory/scavenging activities on 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radicals, total ROS and peroxynitrites ($ONOO^-$). In the present study, the antioxidant activities of this MeOH extract and the organic solvent-soluble fractions, dichloromethane (CH$_2$Cl$_2$), ethyl acetate (EtOAc), and n-butanol (n-BuOH), and the water layer of P. davidiana stem were evaluated for the potential to inhibit $^-OH$ and total ROS generation in kidney homogenates using 2',7'-dichlorodihydrofluorescein diacetate (DCHF-DA), and for the potential to scavenge authentic $ONOO^-$. We also evaluated the inhibitory activity of seven flavonoids isolated from P. davidiana stem, kaempferol, kaempferol 7-Ο-$\beta$-D-glucoside, (+)-catechin, dihydrokaempferol, hesperetin 5-Ο-$\beta$-D-glucoside, naringenin and its 7-Ο-$\beta$-D-glucoside, on the total ROS, $^-OH$ and $ONOO^-$ systems. For the further elucidation of the structure-inhibitory activity relationship of flavonoids on total ROS and 'OH generation, we measured the antioxidant activity of sixteen flavonoids available, including three active flavonoids isolated from P. davidiana, on the total ROS and 'OH systems. We found that the inhibitory activity on total ROS generation increases in strength with more numerous hydroxyl groups on their structures. Also, the presence of an ortho-hydroxyl group, whether on the Aring or S-ring, and a 3-hydroxyl group on the C-ring increased the inhibitory activity on both total ROS and $^-OH$ generation.

• Korean Journal of Food Science and Technology
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• v.46 no.4
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• pp.465-469
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• 2014

The extraction of flavanones such as naringin, narirutin, naringenin, hesperidin, and hesperetin from grapefruit peels was performed using subcritical water extraction (SWE), hot water extraction, and conventional methods such as methanol and ethanol extraction. We analyzed the total flavanone content using high-performance liquid chromatography (HPLC) for each extracting method. Among the three methods, SWE was the optimal method with optimal operating conditions of $170^{\circ}C$ temperature and 10 min operating time. The maximum total flavanone extracted was $86.539{\pm}3.52mg/g$ grapefruit peels. Moreover, we treated the extracts with 60% ${\beta}$-cyclodextrin and then analyzed the surface structure of the encapsulated compounds by field emission-scanning electron microscopy (FE-SEM). The results indicated that the encapsulation in ${\beta}$-cyclodextrin improved solubilization, and the inclusion complex could serve as food supplements.

• Korean Journal of Medicinal Crop Science
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• v.23 no.2
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• pp.132-137
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• 2015

This study was conducted to find out the variation in agronomic trait and chemical composition in the collected Perilla frutescens from China and Japan. From the results of growth investigation, the maximum number if branches was 26.7ea in Japan 134 line, followed by 25 nodes number in China 119 line. Among the different lines investigated, maximum number of panicle number (108.8) were observed in China 114 line. 1000 seed weight was maximum (4.12 g) in China 118 line. Flowering time of different collected lines varied significantly with average value of 175.5 days and the average line required for maturation of seedlings was 205.1 days. Plant height was the highest (248.9 cm) in China 107 line. Highest number of total picking leaves was 965ea, and the average picked period was 54 days. The major phenol compounds contained in Perilla frutescens showed wide variation for Syringic acid, Benzoic acid, Naringin, o-Coumaric acid, Myricetin, Naringenin and Hesperetin. Japan 139 line showed the highest level of total phenol contents ($8254.0{\mu}g/g$, dry weight).

• Journal of the Korean Society of Food Science and Nutrition
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• v.43 no.11
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• pp.1688-1694
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• 2014

Jeju Hallabong Tangor (Citrus kiyomi${\times}$ponkan) is a Citrus species with a variety of physiological properties such as anti-oxidant, anti-inflammation, anti-cancer, and anti-obesity. We investigated the anti-obesity effects of Hallabong Tangor peel extracts before (HLB) and after (HLB-C) bioconversion with cytolase based on modulation of adipocyte differentiation and lipid metabolism in 3T3-L1 adipocytes. Treatment with cytolase decreased flavanone rutinoside forms (narirutin and hesperidin) and increased flavanone aglycone forms (naringenin and hesperetin). During adipocyte differentiation, 3T3-L1 cells were treated with 0.5 mg/mL of Sinetrol (a positive control), HLB or HLB-C. Adipocyte differentiation was inhibited in both citrus groups, but not in control and Sinetriol groups. HLB and HLB-C tended to reduce insulin-induced mRNA levels of CCAAT/enhancer-binding protein ${\alpha}$ ($C/EBP{\alpha}$) and sterol regulatory element-binding protein 1c (SREBP1c). Compared to the control and Sinetrol groups, HLB and HLB-C markedly suppressed insulin-induced protein expression of $C/EBP{\alpha}$ and peroxisome proliferator-activated receptor gamma ($PPAR{\gamma}$). The HLB and Sinetrol groups, but not HLB-C group, significantly increased adipolytic activity with higher release of free glycerol compared to the control group in differentiated 3T3-L1 adipocytes. These results suggest that bio-conversion of Hallabong Tangor peel extracts with cytolase increases aglycone flavonoids. Irrespective of bioconversion, both Hallabong Tangor peel extracts exert anti-obesity effects that may contribute to prevention of obesity through inhibition of adipocyte differentiation or induction of adipolytic activity.

• Food Science and Preservation
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• v.15 no.1
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• pp.94-98
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• 2008

To search functional biomaterials of citrus pressed cake, the chemical constituents were analyzed Moisture content of citrus pressed cake varied slightly with sampling time. Moisture, non-nitrogen compounds, crude protein, crude fat, and ash of citrus pressed cake were 82.23% 16.94% 1.27% 2.5%, 0.58% (all w/w) on average, respectively. The chemical composition of citrus pressed cake was more similar to the peel than to the flesh of Citrus unshiu var: miyakawa. The pH, acid content, and pectin content were 3.57, 0.43% (w/w) and 1.49% (w/w), respectively. The vitamin C content of peel of Citrus unshiu var. miyakawa was 87.1mg/100g, and was higher than the 46.4mg/100g of citrus pressed cake. Total carotenoids of citrus pressed cake, and the peel and flesh of Citrus unshiu var. miyakawa, were 512.2mg/kg, 2,649.5mg/kg, and 199.4mg/kg, respectively. Therefore, citrus pressed cake may be utilized as a natural source of pectin, flavonoids and carotenoids. The major inorganic elements of citrus pressed cake were 201.3mg/100g of K, 47.9mg/100g of Ca, 19.4/100g of P, and 17.8/100g of Mg. The major free sugar contents of citrus pressed cake were 3.05% (w/w) fructose, 2.91% (w/w) glucose, and 4.94%(w/w) sucrose. Total free sugar was 9.91% (w/w), corresponding to 58.5% of 1be non-nitrogen compounds. The main flavonoids of Citrus unshiuwere narirutin, hesperidin, and rutin. Neohesperidin and hesperetin were also detected in trace amounts. Themajor flavonoids of citrus pressed cake were hesperidin and narirutin, and the content of hesperidin was 194.6mg/100g.

• Journal of Animal Science and Technology
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• v.55 no.4
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• pp.281-288
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• 2013

This experiment was conducted to determine the effects of extracts from fruit by-products on the blood characteristics, antioxidant activities, and immune response to Escherichia coli lipopolysaccharide (LPS) in growing pigs. A total of 96 pigs [(Landrace ${\times}$ Yorkshire) ${\times}$ Duroc] with an initial BW of $27.94{\pm}0.92kg$ were used in a 6-week feeding trial. The pigs were randomly placed into one of four treatment groups with six replications (four pigs per replication) per treatment according to their initial BW. Treatments were: 1) CON (basal diet), 2) PRO (CON + 0.5% procyanidin), 3) HES (CON + 0.5% hesperetin), 4) TAN (CON + 0.5% tannin). At the end of the sixth week, five pigs (total 20 pigs, $BW=27.94{\pm}0.92kg$) were selected from each treatment and injected with LPS ($100{\mu}g/kg$ of BW). Blood samples were collected 3 h after LPS injection to assess anti-oxidative and inflammatory responses. After the LPS challenge, the concentration of serum cholesterol decreased with fruit by-product treatment compared with CON (p<0.05). The administration of TAN increased the concentration of blood total protein compared with the CON group 3 h after LPS challenge (p<0.05). The albumin concentration was also higher with PRO treatment compared to HES treatment (p<0.05). The concentration of IgM was increased by fruit by-product supplementation at 0 and 3 h (p<0.05). In addition, IgG concentration was higher in PRO, HES, and TAN treatments compared to CON treatment at 0 h, and IgG concentrations were also higher in the HES group compared to the CON group at 3 h (p<0.05). The concentration of IgA also increased with fruit by-product treatments at 3 h (p<0.05). In conclusion, dietary supplementation with fruit by-products may moderate the immune response after a LPS challenge in growing pigs.

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

• Nutrition Research and Practice
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• v.10 no.2
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• pp.131-138
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• 2016

BACKGROUND/OBJECTIVES: Citrus and its peels have been used in Asian folk medicine due to abundant flavonoids and usage of citrus peels, which are byproducts from juice and/or jam processing, may be a good strategy. Therefore, the aim of this study was to examine antioxidant and anti-inflammatory effects of bioconversion of Jeju Hallabong tangor (Citrus kiyomi ${\times}$ ponkan; CKP) peels with cytolase (CKP-C) in RAW 264.7 cells. MATERIALS/METHODS: Glycosides of CKP were converted into aglycosides with cytolase treatment. RAW 264.7 cells were pre-treated with 0, 100, or $200{\mu}g/ml$ of citrus peel extracts for 4 h, followed by stimulation with $1{\mu}g/ml$ lipopolysaccharide (LPS) for 8 h. Cell viability, DPPH radical scavenging activity, nitric oxide (NO), and prostagladin $E_2$ ($PGE_2$) production were examined. Real time-PCR and western immunoblotting assay were performed for detection of mRNA and/or protein expression of pro-inflammatory mediators and cytokines, respectively. RESULTS: HPLC analysis showed that treatment of CKP with cytolase resulted in decreased flavanone rutinoside forms (narirutin and hesperidin) and increased flavanone aglycoside forms (naringenin and hesperetin). DPPH scavenging activities were observed in a dose-dependent manner for all of the citrus peel extracts and CKP-C was more potent than intact CKP. All of the citrus peel extracts decreased NO production by inducible nitric oxide synthase (iNOS) activity and $PGE_2$ production by COX-2. Higher dose of CKP and all CKP-C groups significantly decreased mRNA and protein expression of LPS-stimulated iNOS. Only $200{\mu}g/ml$ of CKP-C markedly decreased mRNA and protein expression of cyclooxygenase-2 in LPS-stimulated RAW 264.7 cells. Both 100 and $200{\mu}g/ml$ of CKP-C notably inhibited mRNA levels of $interleukin-1{\beta}$ ($IL-1{\beta}$) and IL-6, whereas $200{\mu}g/ml$ CKP-C significantly inhibited mRNA levels of $TNF-{\alpha}$. CONCLUSIONS: This result suggests that bioconversion of citrus peels with cytolase may enrich aglycoside flavanones of citrus peels and provide more potent functional food materials for prevention of chronic diseases attributable to oxidation and inflammation by increasing radical scavenging activity and suppressing pro-inflammatory mediators and cytokines.

• Korean Journal of Pharmacognosy
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• v.40 no.4
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• pp.370-375
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• 2009

Overproduction of peroxynitrite ($ONOO^-$) causes a variety of disease such as atherosclerosis, hypercholesterolemia, diabetes mellitus or obesity. Peroxynitrite scavenging activities and HPLC analysis on the five Oriental medicinal drugs belonging to the genus Citrus, Aurantium or Poncirus (Rutaceae family) and HPLC analysis were taken to evaluate flavanone glycosides with peroxynitrite scavenging activity. The $IC_{50}s$ of the five crude drugs were shown as follows: Aurantii nobilis Pericarpium (Jinpi, 18.3 ${\mu}g$/ml), Citrii unshiu Pericarpium (Chungpi, 7.50${\mu}g$/ml), Citrii unshiu Semen (Gyulhaek, >50.0${\mu}g$/ml), Aurantii Fructus (Jigak, 18.3${\mu}g$/ml), and Poncirii Fructus (Jisil, >50.0${\mu}g$/ml) where Korean crude drug's names are noted in the parenthesis. Peroxynitrite scavenging effect of flavanones or their glycosides usually contained in Citrus species were observed as follows: hesperetin (1.89 ${\mu}g$/ml), naringenin (7.77 ${\mu}g$/ml), hesperidin (8.44 ${\mu}g$/ml), poncirin (>50.0 ${\mu}g$/ml)and ponciretin(>50.0 ${\mu}g$/ml). The activities of naringin and poncirin with ${\alpha}$-L-rhamnopyranosyl($1{\rightarrow}2$)-${\beta}$-D-glucopyranosyl moiety were weak. HPLC analytical data revealed that Jinpi (the peels of mature fruits of Citrus unshiu) and Chungpi (the peels of immature fruits of C. unshiu) had high quantities of hesperidin as the value of 142.1${\pm}$0.21 and 104.51${\pm}$1.10 mg/g dried weight, respectively. Poncirin was clearly detected in only Jisil and naringenin and naringin were not observed on the HPLC chromatogram of the five crude drugs.