• Archives of Pharmacal Research
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• 제27권5호
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• pp.518-523
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• 2004

An allergic reaction ensues after antigen binds to mast cell or basophil high affinity IgE receptor, Fc$\varepsilon$RI, resulting in degranulation of various inflammatory mediators that produce various allergic symptoms. In this study, i) we isolated the active component for the inhibition of mast cell degranulation from the extract of leaves of Castanea crenata and identified it as quercetin; ii) we established the total synthesis procedure of quercetin; iii) using quercetin as positive control, we excavated some lead compounds that possess inhibitory activities for mast cell degranulation by screening the chemical libraries of 1,3-oxazolidine derivatives prepared by solid phase combinatorial chemistry. Some of 1,3-oxazolidine compounds possessing acetyl and 3',4'-dichlorophenyl group displayed strong inhibitory activities on Fc$\varepsilon$RI-mediated mast cell degranulation, suggesting that they can be used as lead compounds for the development of anti-allergic agents.

• Archives of Pharmacal Research
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• 제16권1호
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• pp.25-28
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• 1993

Our previous report demonstrated that certain flavonoid aglycones such as apigenin (flavone), quercetin, morin (flavonols), and biochanin A (isoflavone) showed in vivo antiinflammatory activity via topical and oral routes of adminstation. As a continual study, the various flavonoid glycosides have been evaluated in mouse ear edema assay using archidonic acid or croton-oil as a inflammagen. Flavonoids were orally administered (2 mg/mouse) and ear edema inhibition was measured. Significant antiinflammatory activities were found esepcially in flavone and flavonol glycosides (15-29% inhibition) although the flavonoid derivatives tested showed less antiinflammatory activity than hydrocortisone or indomethacin. Chalcone and flavanone derivatives were not significantly active. And in general, flavonol glycosides of kaempferol-type were found to have a higher oral antiinflammatory activity than that of flavonol glycosides of quercetin-type in mice.

• 식물분류학회지
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• 제41권1호
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• pp.10-15
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• 2011

본 연구에서는 한국산 닭의덩굴속 호장근절 분류군들을 대상으로 개체군 수준에서 flavonoid 분석을 수행하여, 본 절 분류군에서 나타나는 형태변이 양상을 화학적 측면에서 파악하고, 이를 토대로 한반도에 분포하는 본 절 분류군들의 실체 및 한계를 정확히 파악하고자 하였다. 그 결과, 한국산 본 절 3분류군 15개체군의 잎으로부터 19종류의 서로 다른 flavonoid compound가 분리, 동정되었으며, 이들은 flavonol인 quercetin 및 kaempferol 3-O-glycoside들과 flavone인 apigenin및 luteolin C-glycoside들이었다. 이들 compound들 중 한국산 본 절 식물에 분포하는 주요 flavonoid compound는 quercetin 3-O-galactoside 와 quercetin 3-O-glucoside이었다. 본 절 한국산 분류군들은 그 flavonoid 조성에 의해 뚜렷이 구분되는 것으로 밝혀졌으며, 이러한 결과는 기존의 외부 형태학적 연구 결과와 전반적으로 일치하였다. 한편, 잡종으로 추정되는 논산 개체군의 flavonoid 조성은 F. japonica var. japonica, F. forbesii 및 F. sachalinensis와 일부 compound를 공유하는 것으로 나타났다. Fallopia japonica var. japonica의 경우, 염색체수 배수화에 따른 flavonoid 조성의 정성적 차이는 발견할 수 없었으나, 지리적 변이가 일부 나타나는 것으로 밝혀졌다.

• Archives of Pharmacal Research
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• 제16권1호
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• pp.18-24
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• 1993

In this inverstigation, the various flavonoid aglycones were evaluated for their inhibitory activities against croton-oil or arachidonic acid induced mouse ear edema by oral or topical administration. The compounds tested were thirteen derivatives of flavan-3-ol(catechin and epicatechin), flavanone (flavanone and naringenin), flavone (flavone, chrysin and apigenin), flavonol(favonol, galangin, quercetin and morin) and isoflavone (biochanin A and 2-carbethoxy-5,7-dihydroxy-4'-methoxyisoflavone), along with hydrocortisone, indomethacin, 4-bormophenacyl bromide, nordihydroguaiaretic acid and phenidone as positive controls. A(isoflavone) were found to show broad inhibitoty activities (14-52%) against croton-oil or arachidonic acid induced ear edema by oral or topical application at the dose of 2 mg/mouse, although they showed less activity than hydrocortisone (26-88%) or indomethacin (36-80%). Flavonoid agtlycones tested showed higher activity when aplied topically than by the oral administration. It was also found that they inhibited arachidonic acid induced edema more profoundly than croton-oil induced edema by topical application. In arachidonic acid induced edema when applied topically, flavone derivatives such as flavone, chrysin and apigenin were revealed to be the good inhibitory agents in addition to flavonols and isoflavones. When quercetin and biochanin. A were selected for evaluating in carrageenan induced rat pleurisy and biochanin both flavonoids showed antiinflammatory activity at the dose of 70 mg/kg by the oral adminis-tration. All of these results revealed that flavonoid aglycones, especially 5,7-dihydroxy-flavonols having hydroxyl group(s) in B-ring and biochanin A (isoflavone) possessed in vivo antiinflammatory activity.

• 한국환경생태학회지
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• 제29권2호
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• pp.145-161
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• 2015

This research was conducted in order to understand the hybridization between Quercus aliena Blume and Q. serrata Murray in Korea which show wide range of morphological variations within species and interspecific variations of diverse overlapping characteristics caused by hybridization. Morphological analysis (principal components analysis; PCA) of 116 individuals representing two species and their intermediates were performed. As a result, two species were clearly distinguished in terms of morphology, and intermediate morpho-types assumed to be hybrids between the two species were mostly located in the middle of each parent species in the plot of the principal components analysis. There was a clear distinction between two species in trichome distribution pattern which is an important diagnostic character in taxonomy of genus Quercus, whereas intermediate morpho-types showed intermediate state between two species' trichome distributions. Forty-two individuals representing two species and their intermediates were examined for leaf flavonoid constituents. Twenty-three flavonoid compounds were isolated and identified: They were glycosylated derivatives of flavonols, kaempferol, quercetin, isorhamnetin and myricetin. The flavonoid constituents of Q. aliena were five glycosylated derivatives: kaempferol 3-O-galactoside, kaempferol 3-O-glucoside, quercetin 3-O-galactoside, quercetin 3-O-glucoside, and Isorhamnetin 3-O-glucoside. The flavonoid constituents of Q. serrata had 20 diverse flavonol compounds including five flavonoid compounds found in Q. aliena. It was found that there is a clear difference in flavonoid constituents of Q. aliena and Q. serrata. Flavonoid chemistry is very useful in recognizing each species and putative hybrids. The flavonoid constituents of intermediates were a mixture of the two species' constituents and they generally showed similar characteristics to morpho-types. The hybrids between Q. aliena and Q. serrata showed morphologically and chemically diverse characteristics and it is assumed that there are frequent interspecific hybridization and introgression.

• 한국식품저장유통학회지
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• 제18권3호
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• pp.328-334
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• 2011

폴리페놀화합물인 안토시아닌, 레스베라트롤, 쿼세틴, 카테킨, 에피카테킨류는 항암작용과 항산화작용을 하는 것으로 보고되고 있다. 본 연구에서는 다양한 국내 육성 포도 품종과 외국 도입 품종에 대하여 포도내 대표적인 폴리페놀계 화합물인 안토시아닌, 레스베라트롤, 쿼세틴, 카테킨, 에피카테킨류의 함량을 분석하였다. 전체적으로 카테킨 및 에피카테킨의 함량은 레스베라트롤과 쿼세틴보다 훨씬 높게 검출되었다. 폴리페놀계의 화합물은 과피색 간에 큰 차이는 보이지 않았으나, 동일 과피색내의 품종간에는 유의적인 차이를 나타냈다. 각 과피색 그룹에서 흑색 포도에서는 캠벨얼리, 청색 그룹에서는 세네카, 그리고 적색그룹에서는 베니가드 품종이 가장 높은 수치를 보였다. 성분별로 적게 함유하거나 전혀 검출되지 않는 품종도 일부 존재하였다. 이러한 결과는 향후 포도 육종개발 및 가공 분야에 응용되는 유용한 정보가 될 것으로 기대된다.

• Journal of Applied Biological Chemistry
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• 제66권
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• pp.266-271
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• 2023

본 실험에서는 에탄올로 추출한 Psidium guajava 잎과 컬럼크로마토그래피를 이용한 메탄올 분획물의 항산화 능력을 측정하기 위해 DPPH, ABTS 라디컬소거능법, 총 페놀, 플라보노이드법, SOD assay법을 활용하였다. 항산화 활성 결과에서 40, 60% 메탄올 분획물이 의미있는 측정값을 나타냈고, 두 분획물을 선정하여 HPLC와 핵자기공명(NMR)을 활용한 화학적 분석을 통해 주요 성분의 분리 및 물질탐색을 진행하였다. HPLC 정제를 통해 quercitrin (1)와 isoquercetin (2) 두 종류의 quercetin 유도체를 분리 및 구조 동정하였다. SOD assay 결과에서 컬럼크로마토그래피법을 활용하여 얻은 몇몇의 분획물과 단일물질로 분리한 화합물들은 추출물보다 향상된 항산화 활성을 보였다.

• Journal of Photoscience
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• 제9권2호
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• pp.424-426
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• 2002

Recently, much attention has been paid to the physiological functions of flavonoids associated with their antioxidant properties. However, there was a lack of information on the molecular mechanism at which flavonoids play the antioxidative role. We have already studied on the oxidation of quercetin with hydrogen peroxide and sodium hypochlorite in alcoholic aqueous solution and determined the oxidation products. Through the structural analysis of the oxidation products, it was clarified that the hydroxyl group at C-3 in the C ring plays the important role in the antioxidative action of quercetin. Successively, rutin and (+)-catechin were oxidized with sodium hypochlorite and their mono- and di-chlorinated derivatives were obtained. These facts indicate that these flavonoids can directly scavenge hypochlorous acid and the active site in this scavenging reaction is not the hydroxyl group at C-3.

• Journal of Applied Biological Chemistry
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• 제51권2호
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• pp.57-60
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• 2008

Eight compounds, including 2 flavones, luteolin (1) and apigenin (2), 2 flavonols, kaempferol (3) and quercetin (4), and 4 flavonoid glucosides, luteolin-7-O-${\beta}$-D-glucoside (5), apigetrin (6), astragalin (7), and isoquercitrin (8), isolated from the whole herb of Sonchus oleraceus L. were analyzed on the basis of chemical and spectroscopic evidence. This was the first time to report compounds 3, 4, 6, 7 and 8 from the Sonchus oleraceus L. The antioxidant activities of the isolated flavonoids and their glucoside derivatives were evaluated by DPPH free radical-scavenging assay, showing that compounds 1, 3, 4 and 8 exhibited stronger antioxidant activities compared with ${\alpha}$, tocopherol and curcumin. Flavonoids containing more hydroxyl groups exhibited better antioxidant activities. The antioxidant activity of flavonols was superior to their corresponding flavones, and that of aglycone are more potent than their glucoside derivatives.

• 한국식품영양과학회지
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• 제40권4호
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• pp.517-524
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• 2011

뽕나무(Morus alba L.) 열매 오디로부터 오디주스 및 오디와인 제조 중 부산물로 얻어지는 오디씨를 기능성식품 및 화장품의 신소재로 사용하기 위한 연구의 일환으로 먼저 오디씨로부터 11가지 폴리페놀화합물을 분리 및 동정하였으며, 아울러 그들의 항산화활성과 품종별 함량을 측정하였다. 먼저 탈지오디씨박의 메탄올추출물을 노르말-헥산으로 탈지한 후 디클로로메탄, 에틸아세테이트 및 노르말-부탄올로 용매분획하고, 이중 항산화활성이 강한 에틸아세테이트 분획물을 silica-gel, Sephadex LH-20 및 ODS-A column chromatography를 순차적으로 실시하여 11가지 폴리페놀 화합물을 각각 순수하게 분리 및 정제하였으며, 그들의 화학 구조를 NMR을 이용하여 동정하였다. 오디씨로부터 분리한 11가지 폴리페놀화합물의 항산화활성을 DPPH radical을 이용하여 측정한 결과, rutin($IC_{50}=20.2\;{\mu}M$)이 가장 강한 항산화활성을 나타내었으며, 그 다음으로 isoquercitrin ($IC_{50}=22.5\;{\mu}M$)> quercitrin($IC_{50}=24.6\;{\mu}M$)> quercetin($IC_{50}=27.8\;{\mu}M$)> (+)-dihydroquercetin($IC_{50}=28.9\;{\mu}M$)> chlorogenic acid($IC_{50}=30.6\;{\mu}M$) 순으로 나타내었다. 반면, (+)-dihydrokaempferol($IC_{50}=33.8\;{\mu}M$), trans-resveratrol($IC_{50}=36.2\;{\mu}M$), moracin($IC_{50}=47.6\;{\mu}M$) 및 4-prenylmoracin($IC_{50}=48.2\;{\mu}M$)은 위의 폴리페놀화합물보다 낮은 항산화활성을 나타내었으며, procatechuic acid($IC_{50}=68.2\;{\mu}M$)는 가장 낮은 항산화활성을 나타내었다. 한편, 3가지 뽕나무 품종별 오디씨의 11가지 폴리페놀화합물의 함량을 측정한 결과, rutin이 31.1~60.0 mg/100 g으로 가장 높았으며, 그 다음으로 quercitrin(7.2~34.2 mg/100 g)> dihydroquercetin(13.2~33.1 mg/100 g)> quercetin(15.8~19.5 mg/100 g)> 4-prenylmor acin(10.5~43.3 mg/100 g)> isoquercitrin(5.8~15.4 mg/100g)> chlorogenic acid(0.0~15.3 mg/100 g)> moracin(4.7~7.2 mg/100 g)> procatechuic acid(0.0~11.6 mg/100 g) 순으로 낮게 나타났으며, (+)-dihydrokaempferol 및 transresveratrol의 함량은 미량(< 0.1 mg/100 g)으로 나타났다. 또한, 3가지 품종 중 대성뽕 오디씨는 폴리페놀화합물 중 rutin 및 quercetin 유도체의 함량이 높았으며, 반면 익수뽕 오디씨는 procatechuic 및 chlorogenic acid의 함량이 높았고, 특히 moracin 및 4-prenylmoracin의 함량이 다른 오디품종에 비해 높았으나, 반면 청일뽕은 3가지 품종 중 폴리페놀화합물의 함량이 가장 낮았다. 따라서 오디씨는 항산화성 폴리페놀화합물을 많이 함유하고 있기 때문에 암, 고혈압, 당뇨 및 노화를 예방하는 기능성식품 및 화장품의 신소재로 널리 활용할 수 있을 것으로 예상된다.