• Journal of Applied Biological Chemistry
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• 제52권1호
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• pp.15-20
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• 2009

포플러는 naringenin, kaempferol, myricetin, apigenin, luteolin, rhamnetin, quercetin과 같은 플라보노이드를 가지고 있다. 이러한 플라보노이드들은 여러 가지 효소에 의해 naringenin으로부터 합성된다. 그러나, 포플러에서는 플라보노이드 합성에 관여하는 효소들의 연구가 거의 이루어지지 않았다. 포플러에서 flavone synthase I 유전자를 RT-PCR방법을 이용하여 클로닝하였다. PFNS I-1 유전자의 기질 특성을 알아보기 위하여 대장균에 과발현하여 glutathione S-transferase 친화 크로마토그래피를 이용하여 정제하였다. 정제한 PFNS I-1 재조합 단백질은 flavanone인 2S-naringenin기질을 이용하여 flavone인 apigenin을 생성함을 알 수 있었다. 또한 cofactor인 oxoglutarate, $FeSO_4$, ascorbate, catalase가 PFNS I-1의 반응성에 중대한 영향을 미치는 것을 알 수 있었다. 이상의 결과를 종합해 볼 때 PFNS I-1 유전자는 flavone synthase I을 암호화하는 유전자임을 확인하였다.

• Biomolecules & Therapeutics
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• 제7권4호
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• pp.362-370
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• 1999

Propolis, a natural resinous compound collected from honey bees, contains many biochemical constituents(wax, flavonoids, phenolic compounds, etc.) and has been used in traditional medicines as early as 300 B.C. It was been demonstrated that ethanol, acetylsalicylic acid, ischemia reperfusion, non-steroidal antiin-flammatory drugs and stress induce gastric lesions by promoting the generation of reactive oxygen metabolites. Therefore, some drugs that are capable of scavenging or inhibiting the generation of reactive oxygen radicals might be expected to prevent the gastric mucosal injury. The aim of this study was 1) to examine the antiulcer effect of propolis, 2) to investigate the mechanism of action by determining gastric acid secretion, lipid per-oxidation, mucus content and proton pump ($H^+$/$K^+$-ATPase) activity on gastric mucus in varios experimental models, and finally, 3) to isolate and identify the pure compounds that exert antiulcer activity. Step 2-1 and 2-3 sub-sub fraction shoed a significant reduction of severity of gastirc damage at the dose of 25 mg/kg in various experimental models. We isolated 4 sub-sub-sub fractions by flash column chromatography of Step 2-1 sub-sub fraction and one sub-sub-sub fraction by recrystalization of Step 2-3 sub-sub fraction. The protective effects of propolis sub-sub-sub fraction manifested sifnificant effects in HCl-ethanol induced gastric erosion model and aspirin induced gastric ulcer model. These results showed that the gastric mucosal protective effect of propolis might result from the increase of mucus secretion, free radical scavenging effect as well as the reduction of acid secretion in accordance with the reduction of $H^+$/$K^+$-ATPase activitv. Three compounds were isolated and identified from sub-sub fraction of propolis which showed antiulcer effects. Subsequently, these compounds were identified as a flavonoid, namely, 2-acetoxy-5,7,-dihydroxy-flavanone, galangin and chrysin.

• Archives of Pharmacal Research
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• 제28권5호
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• pp.534-540
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• 2005

Activity-guided fractionation of the CH$_2Cl_2$-soluble fraction of the roots of Sophora flavescens furnished five 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scaveng ers: trans-hexadecyl ferulic acid (1) cis-octadecyl ferulic acid (2), trans-hexadecyl sinapic acid (3), (-)-4-hydroxy-3-methoxy-(6aR,11aR)-8, 9-methylenedioxypterocarpan (4) and desmethylanhydroicaritin (8), along with nine known inactive compounds: (-)-maackiain (5), xanthohumol (6), formononetin (7), (2S)-2'-methoxykurarinone (9), (2S)-3${\beta}$,7,4'-trihydroxy-5-methoxy-8-(${\gamma},{\gamma}$- imethylallyl )-flavanone (10), (2S)-7,4'-dihydroxy-5-methoxy-8- (${\gamma},{\gamma}$-dimethylallyl ) -flavanone (11), umbelliferone (12), kuraridin (13), and trifolirhizin (14). Compounds 1-4 and 8 exhibited DPPH free radical scavenging effects at IC$_{50}$ values of 33.01 ${\pm}$ 0.20, 57.06 ${\pm}$ 0.16, 39.84 ${\pm}$ 0.36, 35.83 ${\pm}$ 0.47, and 18.11 ${\pm}$ 0.04${\mu}$M, respectively. L-Ascorbic acid, when used as a positive control, exhibited an IC$_{50}$ value of 7.39 ${\pm}$ 0.01 ${\mu}$M. Compounds 1-4 and 8 also appeared to exert significant scavenging effects on authentic ONOO-, with IC$_{50}$ values of 5.76 ${\pm}$ 1.19, 15.06 ${\pm}$ 1.64, 8.17 ${\pm}$ 4.97, 1.95 ${\pm}$ 0.29 and 4.06 ${\pm}$ 2.41 ${\mu}$M, respectively. Penicillamine (IC$_{50}$= 2.36 ${\pm}$ 0.79${\mu}$M) was used as a positive control. In addition, compounds 2,4,6,8, and 10 were isolated from this plant for the first time.

• 한국식품과학회지
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• 제30권3호
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• pp.672-679
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• 1998

고삼 75% 에탄올 추출물과 클로로포름 분획물을 첨가하여 몇가지 식중독 미생물의 증식억제 양상과 분리된 유효 물질의 구조를 확인하였다. 이 분획물의 항균 효과를 시험한 결과 Listeria monocytogenes (ATCC 19111, 19112, 19113, 19114 및 15313)에 대한 최소 증식억제 농도가 각각 $50{\sim}500\;ppm$과 50 ppm 이하로 확인되었다. 항균 활성을 보인 클로로포름 분획물을 silica gel column chromatography로 연속 2회 정제하여 얻은 황색 분말의 항균 활성 소획분 S-10-6은 L. monocytogenes 5 균주, Bacillus subtilis 및 Staphylococcus aureus에 대해서는 10 ppm 농도에서 뚜렷한 증식억제 효과를 보였으며 특히 L. monocytogenes 5균주에 대해서는 $30{\sim}50\;ppm$ 수준에서 살균 효과가 인정되었으나 E. coli 경우 100 ppm 농도에서도 증식억제 효과가 없었다. 항균 활성을 보인 소획분(S-10-6)을 IR, $^1H-NMR$ 및 $^{13}C-NMR$로 구조를 동정한 결과 flavanone 화합물의 하나인 kushenol F로 확인되었다.

• 한국식품과학회지
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• 제30권3호
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• pp.680-687
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• 1998

감초(Glycyrrhiza uralensis FISCH) 75% 에탄올 추출물이 L. monocytogenes 5 균주에 대하여 뚜렷한 항균 활성이 인정되어 용매 분획한 후 활성이 높은 에틸아세테이트 분획물을 얻었고 이를 silica gel column chromatography로 연속으로 2회 정제하여 황색 분말의 항균 활성 소획분을 분리하였다. 활성 소획분은 L. monocytogenes에 대해서는 $10{\sim}50\;ppm$ 수준에서 증식억제 효과를 보였고 50 및 100 ppm 농도에서는 살균 효과가 인정되었으며 S. aureus에 대해서는 $30{\sim}50\;ppm$ 수준에서 증식억제 효과를 보였으며 E. coli에 대해서는 100 ppm 농도에서도 증식억제 효과가 전혀 나타나지 않았다. IR, $^1H-NMR$ 및 $^{13}C-NMR$로 기기분석하여 활성 획분의 구조를 분석한 결과 감초에 함유된 flavanone 화합물의 하나인 liquiritigenin으로 동정되었다.

• 한국식품과학회지
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• 제46권4호
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• pp.465-469
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• 2014

버려지는 자몽 껍질에 다량 함유되어있는 플라바논을 추출하여 기능성 성분을 재이용하였다. 친환경용매인 아임계수 추출기술을 이용하여 $170^{\circ}C$, 10 min의 최적 조건에서 추출함으로써 무독성 용매로 빠르고 경제적으로 추출할 수 있었다. 자몽껍질 추출물을 ${\beta}$-cyclodextrin을 이용하여 처리함으로써 플라바논과 같은 비극성 물질을 캡슐화하여 소재의 가용화를 용이하게 하였다. 이것은 항산화 기능이 향상된 대체 소재의 개발 및 건강지향식품에 이용할 수 있으며, 이를 통하여 세계 기능성 식품 시장으로의 진출을 위한 발판으로도 삼을 수 있을 것으로 기대된다.

• 약학회지
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• 제36권6호
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• pp.548-555
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• 1992

The biological activities of fruits of Poncirus trifoliata have been studied. 70% Ethanol extract of Ponciri Fructus was fractionated with ether, ethyl acetate and n-butanol by turns. The ether fraction showed antibacterial activity on Staphylococcus aureus and inhibited the contractability of the isolated mice ileum. The ethyl acetate and n-butanol fractions showed the anti-edematous effect on the carrageenin-induced edema of rat hindpaw. From the n-butanol fraction, one of the flavonoid glycoside was isolated and identified as poncirin. Ponciri Fructus contained about 6% poncirin which was 5,7-dihydroxy-4´-methoxy flavanone rhamnoglucoside and poncirin showed antiinflammatory activities. Poncirin was considered as the major effective component of Ponciri Fructus.

• Journal of Microbiology and Biotechnology
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• 제20권9호
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• pp.1295-1299
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• 2010

Recently, recombinant Streptomyces venezuelae has been established as a heterologous host for microbial production of flavanones and stilbenes, a class of plant-specific polyketides. In the present work, we expanded the applicability of the S. venezuelae system to the production of more diverse plant polyketides including flavones and flavonols. A plasmid with the synthetic codon-optimized flavone synthase I gene from Petroselium crispum was introduced to S. venezuelae DHS2001 bearing a deletion of the native pikromycin polyketide synthase gene, and the resulting strain generated flavones from exogenously fed flavanones. In addition, a recombinant S. venezuelae mutant expressing a codon-optimized flavanone $3{\beta}$-hydroxylase gene from Citrus siensis and a flavonol synthase gene from Citrus unshius also successfully produced flavonols.

• Archives of Pharmacal Research
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• 제20권4호
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• pp.368-371
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• 1997

In an effort to increase of the antitumor activity of 2(S)-$2^{I}$,$5^{I}$-trihydroxy-7, 8-dimethoxyflavanone isolated from Scutellaria indica, we synthesized its analogues, II, III and IV. They showed potent cytotoxicity in vitro against cancer cell lines, L1210, K562 and A549. On the basis of $ED_50$ values against the cancer cell lines, III exhibited about 2-7 times stronger activity than I against various cell lines. We tested the antitumor activity of the analogues against Sarcoma 180 cells in vivo and evaluated the structure-activity relationship. The antitumor activity appeared to be related to the hydrogen bond between carbonyl group at C-4 and hydroxyl group at C-5, in contrast to cytotoxic action.

• 약학회지
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• 제52권4호
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• pp.274-278
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• 2008

Two known lavandulylated flavanones, leachianone A (1) and sophoroaflavanone G (2), were isolated from the roots of S. flavascens Ait. The structures of these compounds were determined on the basis of IR, 1D and 2D NMR in addition to direct comparison with authentic compounds. However, leachianone A (1) and sophoroflavanone G (2) did not have growth inhibition activity against any microorganisms (MIC, >200 ${\mu}g/ml$).