• 생명과학회지
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• 제15권2호
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• pp.231-235
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• 2005

기질 금속단백분해효소(MMP)는 기저막이나 간질성 조직 등에 있는 세포외기질 성분을 분해하여 상처 치유, 태아의 발생, 종양세포의 침윤과 전이 등을 포함하여 조직이 재구성되는 과정에서 생리학적 및 병리학적인 과정 양쪽 모두에 매우 중요한 역할을 한다. 본 연구에서는 MMP-9 유전자의 발현을 억제하는 물질을 천연물에서 탐색하였고, 탐색된 시료 중에서 높은 역가를 가진 낙우송과의 Metasequoia glyptostroboides가 선택되었다. 여러 가지 flavonoid 성분을 가지고 있는 Metasequoia glyptostroboides를 이용하여 4개의 biflavonoid와 2개의 monoflavonoid 구조의 물질을 분리하였고, 이 flavonoid들은 sciadopitysin, isoginkgetin, bilobetin, 2, 3-dihydrohino-kiflavone, luteolin, apigenin으로 정제하여 구조를 밝히고 zymography, WST-1을 이용한 세포독성시험, northern blot 등의 실험을 통하여 각 화합물의 구조적인 특성과 함께 MMP-9 유전자 발현을 억제하는 효과가 있는 것을 확인하였다.

• Food Science and Biotechnology
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• 제18권2호
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• pp.463-470
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• 2009

Sixteen antioxidative active compounds isolated from the EtOAc layer of MeOH extracts of kochujang, Korean fermented red pepper paste, were structurally elucidated as fumaric acid, methyl succinate, succinic acid furan-2-yl ester methyl ester (gochujangate, a novel compound), 2-hydroxy-3-phenylpropanoic acid, 3,4-dihydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 6,7-dihydroxy-2H-chromen-2-one (esculetin), caffeic acid, cis-p-coumaric acid, trans-p-coumaric acid, daidzin, genistin, apigenin 7-O-$\beta$-D-apiofuranosyl($1{\rightarrow}2$)-$\beta$-D-glucopyranoside, apigenin 7-O-$\beta$-Dglucopyranoside, and quercetin 3-O-$\alpha$-L-rhamnopyranoside by mass spectrometry (MS) and nuclear magnetic resonance (NMR) experiments. These compounds were analyzed for the first time as antioxidants from kochujang.

• Bulletin of the Korean Chemical Society
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• 제28권8호
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• pp.1335-1340
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• 2007

β-Ketoacyl acyl carrier protein synthase (KAS) III is a particularly attractive target in the type II fatty acid synthetic pathway, since it is central to the initiation of fatty acid synthesis. Enterococcus faecalis, a Grampositive bacterium, is one of the major causes of hospital acquired infections. The rise of multidrug-resistant of most bacteria requires the development of new antibiotics, such as inhibition of the KAS III. In order to block the fatty acid synthesis by inhibition of KAS III, at first, three dimensional structure of Enterococcus faecalis KAS III (efKAS III) was determined by comparative homology modeling using MODELLER based on x-ray structure of Staphylococcus aureus KAS III (saKAS III) which is a gram-positive bacteria and is 36.1% identical in amino acid sequences with efKAS III. Since His-Asn-Cys catalytic triad is conserved in efKAS III and saKAS III, substrate specificity of efKAS III and saKAS III and the size of primer binding pocket of these two proteins are expected to be similar. Ligand docking study of efKAS III with naringenin and apigenin showed that naringenin docked more strongly with efKAS III than apigenin, resulting in the intensive hydrogen bond network between naringenin and efKAS III. Also, only naringenin showed antibacterial activity against E. faecalis at 256 μg/mL. This study may give practical implications of flavonoids for antimicrobial effects against E. faecalis.

• 통합자연과학논문집
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• 제5권2호
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• pp.107-119
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• 2012

Polymerization of monomeric amyloid-${\beta}$ peptides ($A{\beta}$) into soluble oligomers and insoluble fibrils is one of the major pathways triggering the pathogenesis of Alzheimer's disease (AD). Using small molecules to prevent the polymerization of $A{\beta}$ peptides can, therefore, be an effective therapeutic strategy for AD. In this study, we investigated the effects of mono- and bi-flavonoids on $A{\beta}42$ toxicity and fibrillogenesis and found that the bi-flavonoid, taiwaniaflavone (TF) effectively and specifically inhibits $A{\beta}$ toxicity and fibrillogenesis. Compared to TF, the mono-flavonoid apigenin (AP) is less effective and less specific. Our data showed that differential effects of the mono- and bi-flavonoids on $A{\beta}$ fibrillogenesis correlate with their varying cytoprotective efficacies. We also found that other bi-flavonoids, namely 2',8"-biapigenin, amentoflavone, and sumaflavone, can also effectively inhibit $A{\beta}$ toxicity and fibrillogenesis, implying that the participation of two mono-flavonoids in a single bi-flavonoid molecule enhanced their activity. Bi-flavonoids, while strongly inhibited $A{\beta}$ fibrillogenesis, accumulated nontoxic $A{\beta}$ oligomeric structures, suggesting that these are off-pathway-oligomers. Moreover, TF abrogated the toxicity of preformed $A{\beta}$ oligomers and fibrils, indicating that TF and other bi-flavonoids may also reduce the toxicity of toxic $A{\beta}$ species. Altogether, our data clearly show that bi-flavonoids, possibly due to the possession of two $A{\beta}$ binders separated by an appropriate size linker, are likely to be promising therapeutics to suppress $A{\beta}$ toxicity.

• Archives of Pharmacal Research
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• 제27권2호
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• pp.177-183
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• 2004

In order to develop new anti-photoaging agents, we examined the antioxidative activity and the inhibition effect of matrix metalloproteinase-1 (MMP-1) on the extracts of a marine product, Zostera marina L., which is known for its potent activity. Three compounds (compounds 1, 2, and 3) were isolated from an ethyl acetate (EtOAc) soluble fraction of the product; they were identified as apigenin-7 -O-$\beta$-D-glucoside (1), chrysoeriol (2), and luteolin (3). These compounds were found to scavenge radicals and reactive oxygen species (ROS) and were measured to have $SC_{50}$/ values of 0.18 mM, 0.68 mM, and 0.01 mM against the 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical and 0.04 mM, 0.03 mM, and 0.01 mM against the superoxide radical in the xanthine/xanthine oxidase system, respectively. Compound 3 suppressed the expression of MMP-1 by up to 44％ at 4.0 $\mu$M and inhibited the production of interleukin 6 (IL-6), which is known as a cytokine that induces MMP-1 expression. From these results, compound 3 and the other compounds were determined to have antioxidative activity and to inhibit MMP-1 expression. Thus, the three compounds are expected to be useful for preventing the photoaging of skin.

• 한국식품조리과학회지
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• 제25권4호
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• pp.406-414
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• 2009

This study was conducted to investigate the functional composition and antioxidant activity of Cirsium and Carduus genera based on different parts. Leaves of Cirsium setidens Nakai contained 23.66% protein and seeds of Carduus crispus L contained 25.30% lipid. Extraction yields of Cirsium and Carduus genera were higher in leaves than in any other parts of the plants. Total phenolics and total flavonoid content were abundant in extracts of leaves, steam and root of C. japonicum var. ussuriense, and the flower extract of C. setidens Nakai. Silymarin was not found in extracts of Cirsium and Carduus genera. Acacetin was identified in leaf or flower extracts of C. setidens Nakai, or in leaf and steam extracts of C. pendulum Fisch ex DC. Apigenin was identified in the flower extracts of Cirsium and Carduus genera and constituted 7.16 mg/g in C. japonicum var. ussuriense. Cynarin was present at 5.55 mg/g in the seed extract of C. setidens Nakai, and narirutin represented 19.56 mg/g and, 4.18 mg/g of the seed extracts of C. pendulum Fisch ex DC and, Carduus crispus L, respectively. 2,2-Diphenyl-1-2-picrylhydrazyl (DPPH) radical scavenger activity was higher in flower extracts of C. setidens Nakai than in the other genera. Photochemiluminescence activity was 2.3 nmol in leaves and flower extracts of C. setidens Nakai and flower extract of Carduus crispus L. Flowers and seeds of C. setidens Nakai shoe potential as new functional materials.

• Journal of Nutrition and Health
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• 제35권10호
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• pp.1081-1088
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• 2002

Flavonoids are phytochemicals that occur ubiquitously in plant foods that have been reported to have potential roles in the prevention of cancer, inhibition of platelet aggregation or inflammation. However, there was no accurate data reported on the intake of middle-aged Korean population. The present study was designed to assess dietary intake of flavonoids (including isoflavones) of 304 adults (20-59 yr, male 115, famale 189) living in Daejeon area using semi-quantitative food frequency questionnaire. The questionnaire consisted of 50 food items, including vegetables, soy products, seaweeds, nuts and beans, fruits and beverages. Our self-administered questionnaire contained questions regarding subject's habitual diet and alcohol intake over the previous 3 months. Average daily intake of individual flavonols such as quercetin, kaempferol, myricetin, and flavones such as luteolin, apigenin was 15.7, 8.7, 0.21, 2.07, 0.03 mg/day, respectively. Daily intake of daidzein and genistein, which are the commonly found isoflavones in soy products, were 16.6 and 21.4 mg/day, respectively. Combined intake of flavonoids was 64.3 mg/day. No effect of smoking, drinking and exercise was observed on flavonoids consumption. Food items that has the highest daily intake of each compounds were; quercetin (onion, 9.49 mg/day), kaempferol (strawberry, 1.18 mg/day), myricetin (green tea, 0.81 mg/day), apigenin (lettuce, 0.03 mg/day), luteolin (onion, 0.05 mg/day), daidzein (soybean sprout, 5.99 mg/day), genistein (soybean sprout, 7.02 mg/day). These findings provide valuable information on understanding the dietary flavonoids intake from a typical Korean daily diet, which might help to identify the risks for developing various diseases.

• Annals of dermatology
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• 제30권6호
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• pp.694-700
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• 2018

Background: Kaempferol (3,4',5,7-tetrahydroxyflavone) is a flavonoid known to have a wide range of pharmacological activities. The 3-OH group in flavonoids has been reported to determine antioxidant activities. Objective: We tested whether kaempferol can affect the expression of integrins and the stem cell fate of interfollicular epidermal stem cells. Methods: Skin equivalent (SE) models were constructed, and the expression levels of stem cell markers and basement membrane-related antigens were tested. The immunohistochemical staining patterns of integrins, p63, and proliferating cell nuclear antigen (PCNA) were compared between kaempferol- and apigenin-treated SE models. Reverse transcription-polymerase chain reaction (RT-PCR) was used to evaluate the mRNA expression of integrins. Results: Kaempferol increased the thickness of the epidermis when added to prepare SEs. In addition, the basal cells of kaempferol-treated SEs appeared more columnar. In the immunohistological study, the expression of integrins ${\alpha}6$ and ${\beta}1$ and the numbers of p63- and PCNA-positive cells were markedly higher in the kaempferol-treated model. However, apigenin showed no effects on the formation of three-dimensional skin models. RT-PCR analysis also confirmed that kaempferol increased the expression of integrin ${\alpha}6$ and integrin ${\beta}1$. Conclusion: Our findings indicated that kaempferol can increase the proliferative potential of basal epidermal cells by modulating the basement membrane. In other words, kaempferol can affect the fate of interfollicular epidermal stem cells by increasing the expression of both integrins ${\alpha}6$ and ${\beta}1$. These effects, in particular, might be ascribed to the 3-OH group of kaempferol.

• 공업화학
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• 제28권4호
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• pp.479-484
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• 2017

본 연구에서는 라벤더 70% 에탄올 추출물 및 분획물의 항산화 활성과 세포보호효과를 조사하였다. 자유라디칼(1,1-phenyl-2-picrylhydrazyl, DPPH) 소거 활성($FSC_{50}$)은 라벤더 추출물, 에틸아세테이트 및 아글리콘 분획에서 각각 46.6, 45.5 및 $477.5{\mu}g/mL$를 나타냈다. $Fe^{3+}-EDTA/H_2O_2$계에서의 총항산화능($OSC_{50}$)은 라벤더 추출물, 에틸아세테이트 및 아글리콘분획에서 각각 8.1, 3.3 및 $17.6{\mu}g/mL$이었으며, L-ascorbic acid의 $OSC_{50}$ ($1.5{\mu}g/mL$)보다 낮은 활성을 나타냈다. $^1O_2$으로 유도된 적혈구 광용혈 실험에서 아글리콘 분획은 매우 큰 세포보호활성을 나타냈다. $50{\mu}M$ 농도에서 라벤더 추출물, 에틸아세테이트 및 아글리콘 분획의 세포보호효과(${\tau}_{50}$)가 70.6, 87.2 및 165.2 min으로 나타났다. 특히, 라벤더 아글리콘 분획은(+)-${\alpha}$-tocopherol 보다 3.8배 높은 세포보호효과를 나타냈다. TLC 및 LC-MS를 이용하여 라벤더 분획의 성분(luteolin 7-O-glucuronide, vitextin, rosmarinic acid, luteolin, apigenin)을 확인하였으며, 아글리콘 분획은 에틸아세테이트 분획에 비해 주요 플라보노이드(luteolin, apigenin)는 크게 증가하지 않았다. 결론적으로 라벤더가 화장품의 항산화 소재로써 응용 가능함을 시사한다.

• 대한화장품학회지
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• 제43권2호
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• pp.175-187
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• 2017

본 연구에서는 풍선덩굴 잎 추출물 및 그 분획물에 대하여 항산화 활성 평가와 성분 분석을 수행하였다. 본 실험에는 풍선덩굴 건조 잎의 50% 에탄올 추출물, 에틸아세테이트 분획 및 아글리콘 분획을 사용하였으며, 각각의 수율은 16.4, 0.9 및 0.3%로 나타났다. 자유라디칼 소거활성(1,1-diphenyl-2-picrylhydrazyl, DPPH, $FSC_{50}$)은 에틸아세테이트 분획($92.5{\mu}g/mL$)이 가장 큰 것으로 나타났으며, 이때 대조군인 (+)-${\alpha}$-tocopherol의 $FSC_5$은 $8.9{\mu}g/mL$이었다. $Fe^{3+}-EDTA/H_2O_2$계를 이용한 활성산소 소거활성(총항산화능, $OSC_{50}$)은 아글리콘 분획($4.2{\mu}g/mL$)에서 가장 크게 나타났으며, 대조군인 L-ascorbic acid ($1.5{\mu}g/mL$)와 유사한 효과를 나타내었다. $^1O_2$로 유도된 사람 세포 손상에 대한 보호효과 측정에서 풍선덩굴 잎 추출물 및 분획은 모두 농도 의존적($5.0-25.0{\mu}g/mL$)으로 세포보호효과를 나타냈다. 추출물/분획물 중에서 아글리콘 분획(${\tau}_{50}$, 76.4 min)이 가장 큰 세포보호효과를 나타내었다. TLC, HPLC, LC/ESI-MS를 이용하여 풍선덩굴 잎 추출물 중 에틸아세테이트 분획물에 대하여 성분 분석을 실시하였다. 그 결과, apigenin-7-O-glucuronide, apigenin-7-glucosdie 및 quercitrin hydrate 등의 플라보노이드가 함유되어 있음을 확인하였다. 이상의 결과들은 풍선덩굴 잎 추출물 또는 분획이 항산화 기능성 화장품 원료로서 응용 가능성이 있음을 시사한다.