• Analytical Science and Technology
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• v.24 no.2
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• pp.135-141
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• 2011

MMPs (Matrix metalloproteinases) are enzymes playing an important role to turnover and remodel main protein compositions of extracellular matrix. MMP-2 and MMP-9 of MMPs having a catalytic domain which is apart from a hemopexin-like domain part, are different from the other MMPs pertaining fibronectinlike domain close to hemopexin-like domain. It was reported that the development of MMP-9 restrainer can prevent the transfer of liver cancer. In this study, MMP-9 restrainers were extracted and purified from Hovenia dulcis Thunberg. The each fractionary part was examined to investigate the inhibitory effect on MMPs. Three compounds, compound A and B eluted with ethyl acetate (EA) and compound C with methanol, were identified by $^1H$ and $^{13}C$ NMR, GC/MS, and FT-IR. Compound A is considered as a kind of catechine type compound having a benzene ring substituted by hydroxyl and methoxyl groups. Compound B and C are nobiletin type compound pertaining a carbonyl group. Compound A, B and C showed 76%, 66% and 71% of inhibition effect on MMP-9 at 1.0% concentration, respectively. Compound A showed the best inhibition effect on MMP-9.

• Journal of Applied Biological Chemistry
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• v.44 no.3
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• pp.143-146
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• 2001

Eight flavonoids, including rutin, naringin, hesperidin, quercetin, hesperetin, nobiletin, 3,5,6,7,8,3',4'-methoxylated flavone, and tangeretin, in the peels of satsuma mandarin (Citrus unshiu) species of Halla, Gungcheon, Hungjin, Namgam-20, Illnam-1, and Chungdo harvested between August and December were analyzed through HPLC. Hesperidin content of Halla harvested during early maturation was 28.70 mg/g, and was the highest among the tested citrus fruits. Rutin content of Hungjin harvested during early maturation was 2.66 mg/g. Naringin in all citrus species and hesperetin in Halla, Gungchun, Namgam-20, and Chungdo were only detected in the peel of fruits harvested during early maturation. Hesperidin and rutin were detected mainly in all citrus species, and other flavonoids in trace. Flavonoid content in the peel of fruits was high during early maturation. Flavonoid contents in the peels of all fruit samples were generally high in the early stage of maturation, which then decreased rapidly.

• International Journal of Oral Biology
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• v.45 no.2
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• pp.33-41
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• 2020

Neuroinflammation is known as the main mechanism implicated in the advancement of neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease. The main feature of neuroinflammation is associated with the activation of microglia. The activated microglia increase proinflammatory cytokine production and induce progressive neuronal cell death. Citrus flavonoids show neuroprotective effects that are associated with the anti-inflammatory action of flavonoids in neurodegenerative diseases. Among these citrus flavonoids, kaempferol, naringin, and nobiletin show inhibitory effects on nuclear factor-κB and mitogen-activated protein kinase signaling pathways that can modulate inflammatory conditions in microglial cells. In the present review, we present the anti-inflammatory activities of citrus flavonoids and therapeutic potential of flavonoids as neuroprotective agents.

• Journal of the Korean Chemical Society
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• v.65 no.5
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• pp.327-332
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• 2021

Shiranuhi is a fruit of Citrus species widely cultivated in Jeju Island, Korea. From an extract of Shiranuhi tree branches were identified five polymethoxyflavones possessing anti-inflammatory effects; nobiletin (1), sinensetin (2), tetramethylscutellarein (3), 6-hydroxy-5,7,3',4'-tetramethoxyflavone (4) and 5-desmethylsinensetin (5). Evaluation of the activities was conducted by monitoring the production of nitric oxide (NO), prostaglandin E₂ and pro-inflammatory cytokines (TNF-α, IL-1β, IL-6) as well as the levels of iNOS and COX-2 protein expression in LPS-induced RAW264.7 cells. Among the isolates, the compound 4 exhibited the most significant NO inhibition, and suppressed the levels of iNOS and related cytokines. Therefore, it was suggested that the extract and constituents from Shiranuhi tree branches could be useful as anti-inflammatory ingredient.

• Proceedings of the Plant Resources Society of Korea Conference
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• 2022.09a
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• pp.105-105
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• 2022

Unripen mandarin in Jeju Island is known to contain functional ingredients including various flavonoids. This Study was carried out to identify the components of Unripen mandarin extracts and Secondary metabolism by enzyme treatment on Unripen mandarin. We extracted Unripen mandarin using optimal extraction method and selected the most optimal enzyme among commercial enzymes for a Secondary metabolism. As a result, flavonoid components such as Hesperidine and Narirutin, which are known to be contained a lot in unripen mandarin, could be analyzed. However In this extraction method there were no other flavonoid components such as Nobiletin, Tangeretin known to contain in unripen mandarin. However as a result of secondary metabolism a new functional component called Prunin which was not known to be contained in unripen mandarin, was detected as a secondary metabolic product due to enzyme treatment. Through this, it can be confirmed that it would be possible to develop high-value-added products by enzyme treatment on unripen mandarin.

• Journal of Nutrition and Health
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• v.42 no.3
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• pp.278-290
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• 2009

This study aims to evaluate the changes of flavonoid contents and antioxidants activity of Jeju native citrus fruits juice according to the harvest date. Flavonoids such as quercatagetin, narirutin, hesperidin and neohesperidin were contained most plentifully in the juice of Jigak (Citrus aur-antium) by 573.73 mg/100 mL, Sadoogam (C. pseudogulgul) by 393.99 mg /100 mL, Soyooja by 29.63 mg/100 mL and Jigak (C. aurantium) by 201.23 mg/100 mL in the late August, respectively. The highest contents of nob-iletin, sinensetin and tangeretin among polymethoxyflavones were found in the juice of Hongkyool (C. tachibana) by 7.39 mg/100 mL, 2.24 mg/100 mL, 0.63 mg/100 mL in the late August, respectively. 3,5,6,7,8,3',4'- Heptamet- hoxyflavone recorded the highest amount in Punkyool (C. tangerina) by 0.27 mg/100 mL in the late August, but the other polymethoxyflavones including 3',4',7,8-tetramethoxyflavone, 3',4'-dimethoxyflavone, 4'-methoxyflavone, 5,6,7,3',4',5'-hexamethoxyflavone, scutellarein tetramethylether were observed only trace amount in all the citrus fruits. Flavonoid contents in the citrus fruit juices were the highest during early maturation and decreased rapidly while ripening. Total polyphenol contents were the highest in the late August and decreased with ripening. However from the late December, the contents were increased again. Antioxidant activities of the fruits were evaluated as electron donating ability and were the lowest in the late September and increased with the fruit ripening. These results suggest that quercetagetin among all the flavonoids was most plentiful in Jigak and Dangyooja (C. grandis), so that the fruits could be used for industrial material of flavonoids and antioxidant agents.

• Applied Biological Chemistry
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• v.50 no.3
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• pp.154-159
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• 2007

In order to prepare liqueur of Citrus platymamma, 500 g dried peel was soaked in 10 l (5%, w/v) of $30{\sim}95%$ ethanol concentration for 70 days. Changes in pH was $5.19{\sim}4.80$ with 30% ethanol concentration, and the pH was decreased as ethanol concentration decreases for 10 days after soaking. Color a-value was decreased and color b-value was increased according to higher ethanol concentration. Extract was $2.00{\sim}2.19%$ (w/v) with $30{\sim}70%$ ethanol concentration. Acid content was $0.18{\sim}0.21%$ (v/v) with $30{\sim}70%$ ethanol concentration, while $0.13{\sim}0.15%$ (v/v) with 95% ethanol concentration. The contents of fructose and glucose was increased with lower ethanol concentration, and sucrose content was decreased with longer soaking time. Main flavonoids were narirutin, hesperidin, nobiletin, 3,5,6,7,8,3'4'-methoxylated flavone, and tangeretin. Most flavonoids were extracted more than 80% of ethanol for $3{\sim}5$ days soaking. Total polyphenol was $628.8{\sim}711.2$ ${\mu}g/ml$ with $30{\sim}70%$ ethanol concentration for 20 days soaking. Therefore, to prepare Citrus platymamma peel liqueur, it is necessary to soak the material in $50{\sim}70%$ ethanol concentration for 20 days.

• Food Science and Preservation
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• v.23 no.7
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• pp.1012-1017
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• 2016

This study was conducted to investigate total flavonoid content, flavonoid composition, and free radical scavenging effects of by-products from five orange cultivars during the period September 2015 to February 2016. Total flavonoid content was highest in peel extracts from immature fruit harvested in September. Total flavonoid contents of all cultivars mostly decreased while ripening. Among the five cultivars, total flavonoid content was highest in Hamlin sweet orange (21.66 mg/g), followed by Sanguinello blood orange (20.39 mg/g), Shamouti orange (18.49 mg/g), Tarocco blood orange (18.46 mg/g), and Olinda Valencia orange (17.07 mg/g). With regard to flavonoid composition, all cultivar materials had high levels of narirutin and hesperidin, but naringin and neohesperidin were not detected in any of the materials. Nobiletin, as polymethoxyflavone, was detected within a$23{\sim}40{\mu}g/mL$ range in the immature fruit of all cultivars. Among all cultivars, antioxidant activities were higher in peel extracts than in pulp extracts. DPPH radical scavenging activities of peel extracts ranged from 40% to 58% while the ABTS radical scavenging activity range was 90~94%. The results indicate that orange, by-products, especially peel of immature orange fruit, could have application as natural materials with antioxidative effects.

• Food Science and Preservation
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• v.23 no.7
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• pp.1026-1032
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• 2016

Citrus platymamma hort. ex Tanaka is widely used in traditional Korean medicine because of its medicinal benefits including an anti-inflammatory effect. This study aimed to evaluate changes in the flavonoid content and anti-inflammatory activities of C. platymamma during its harvest period. Fruit peel samples were obtained between September 2015 and February 2016. The results indicate that C. platymamma peel extract (CPE) was an effective inhibitor of lipopolysaccharide (LPS)-induced NO production in RAW264.7 cells. The inhibitory effects of CPE at $100{\mu}g/mL$ concentration included dose-dependent decreases in the expression of iNOS and COX-2 proteins. In addition, CPE decreased the expression of pro-inflammatory cytokines TNF-${\alpha}$, IL-$1{\beta}$, and IL-6. The highest anti-inflammatory activity and flavonoid content were observed in CPE of C. platymamma peel harvested during the immature fruit period in September. Further, to assess the suitability of CPE for cosmetic use, we performed MTT assays using HaCaT keratinocytes and observed that CPE did not exhibit any cytotoxicity. To test the potential application of CPE as a cosmetic material, we also performed primary skin irritation tests on normal skin of 30 volunteers and no adverse reactions were observed. The results of this study indicate that CPE may be considered as an anti-inflammatory candidate for inclusion in cosmetic materials.

• Journal of the Korean Society of Food Science and Nutrition
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• v.42 no.9
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• pp.1345-1350
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• 2013

The objective of this study was to evaluate the effect of extraction methods on the antioxidant activity of Citrus unshiu pomace. For this purpose, two kinds of citrus pomace (CP)s, whole fruit CP and pulp CP, were used for preparing the extracts with hot water or 70% ethanol. It is well-known fact that whole fruit CP has more calories and carbohydrates, although moisture content is higher in pulp CP. Further, whole fruit CP extracts have higher levels of total phenolic contents compared to CP extracts. In addition, DPPH and alkyl radical scavenging activities were also higher in whole fruit CP, especially in ethanolic extracts. Our results based on liquid chromatography-mass spectrometer showed that 70% ethanolic extract of whole fruit CP has the maximum levels of nobiletin and tangeretin contents. The levels of naringin, which is known as an antioxidant flavonoid, was determined only in the 70% ethanolic extract of whole fruit CP. This result, however, is consistent with the observed DPPH and alkyl radical scavenging activities. We had also performed a gas chromatography analysis that showed all the four extracts contained the compound hydroxymethyl furfural. Significantly, this compound has been reported to have antioxidant activity. Taken together, findings of this study indicate that ethanolic extraction of whole fruit CP is a good source of antioxidant compounds and hence the same could be utilized as an important method to obtain such beneficial compounds on an industrial scale.