• 한국환경성돌연변이발암원학회지
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• 제19권1호
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• pp.56-62
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• 1999

Resveratrol (3,5,4'-trihydroxy-trans-stilbene) has been considered to be as one of major antioxidants present in grapes responsible for beneficial effects of red wine consumption on coronary heart disease. This triphenolic stilbene has been suggested as a potential cancer chemopreventive agent based on its striking inhiitory effects on diverse cellular events associated with tumor initiation, promotion, and progression. The compound has strong antioxidative and anti-inflammatory activities which amy contribute to its chemopreventive/chemoprotective properties. In the present work, we have found that resveratrol reduces viability and DNA synthesis capability of cultured human promyelocytic leukemia (HL-60) cells. Likewise, the viability of human breast cancer cell line, MCF-7 was reduced by resveratrol treatment. The growth inhibitory and antiproliferative properties of resveratrol appear to be associated with its induction of apoptotic cell death as determined by morphological and ultrastructural changes, agarose gel electrphoretic analysis of internucleosomal DNA fragmentation, and in situ terminal end-labeling of fragmented DNA (TUNEL). This compound also inhibited the phorbol ester-induced expression of cyclooxygenase-2 (COX-2) protein in immortalized human mammary epithelial MCF-10A cells. These results suggest that resveratrol has the promising cancer therapeutic/chemopreventive potential.

• 원예과학기술지
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• 제30권6호
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• pp.626-634
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• 2012

본 연구에서는 노지재배 포도의 내한성을 증대시킬 수 있는 방법을 모색하고자 간이비가림시설 설치에 따른 식물체의 반응을 조사하였다. 간이비가림시설에서 월동한 식물체의 탄수화물 함량은 노지 처리구에 비해 높았으며, 'Muscat Bailey A'의 줄기보다 '거봉'과 '캠벨얼리' 품종에서 탄수화물의 함량이 높게 나타났다. 노지에 비해 간이비가림시설에서 발아율과 신초의 생장도 양호하였으나 방충망, 차광막을 처리한 구에서는 유의차가 나타나지 않았다. 포도 잿빛곰팡이병의 발생은 간이비가림시설에서 발생이 적었다. Stilbene 화합물 함량은 노지보다 간이비가림 처리구에서 함량이 약간 더 높게 나타났으며 가장 많이 함유된 stilbene은 배당체 형태인 t-piceid였으며, resveratrol, piceatannol, c-piceid에 비해 상당히 고함량을 나타내었다. Chalcone isomerase, manganese superoxide dismutase, proline rich protein 2, temperature induced lipocalin의 transcripts는 시간이 지날수록 유전자의 발현량이 더 많이 축적되었고, 대체적으로 간이비가림시설의 삽수에서 저온 스트레스에 더 강하게 발현되었다. 처리구별 온도차이는 없었으나 노지에 비해 간이비가림시설에서 풍속이 크게 감소하였으며, 간이비가림시설 내에서 차광막을 설치한 경우 풍속의 감소효과가 현저하게 나타났다. 겨울철의 간이비가림시설과 방충망을 설치함으로써 극저온에 의한 포도나무의 저온피해를 줄일 수 있을 것이다.

• Journal of Microbiology and Biotechnology
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• 제28권7호
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• pp.1105-1111
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• 2018

The flavin-dependent monooxygenase Sam5 was previously reported to be a bifunctional hydroxylase with coumarate 3-hydroxylase and resveratrol 3'-hydroxylase activities. In this article, we showed the Sam5 enzyme has 3'-hydroxylation activities for methylated resveratrols (pinostilbene and pterostilbene), hydroxylated resveratrol (oxyresveratrol), and glycosylated resveratrol (piceid) as substrates. However, piceid, a glycone-type stilbene used as a substrate for bioconversion experiments with the Sam5 enzyme expressed in Escherichia coli, did not convert to the hydroxylated compound astringin, but it was converted by in vitro enzyme reactions. Finally, we report a novel catalytic activity of Sam5 monooxygenase for the synthesis of piceatannol derivatives, 3'-hydroxylated stilbene compounds. Development of this bioproduction method for the hydroxylation of stilbenes is challenging because of the difficulty in expressing P450-type hydroxylase in E. coli and regiospecific chemical synthesis.

• Archives of Pharmacal Research
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• 제19권4호
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• pp.286-291
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• 1996

Phenolic compounds are prevalent as toxins or environmental pollutants, but they are also widely used as drugs for various purpose including anticancer agent. A novel biphenolic compound, bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane (GERI-BPO02-A) was isolated from the fermentation broth of Aspergillus fumigatus F93 previously, and it has revealed cytotoxicity against human solid tumor cells. Its effective doses that cause 50% inhibition of cell growth in vitro against non-small cell lung cancer cell A549, ovarian cancer cell SK-OV-3, skin cancer cell SK-MEL-2 and central nerve system cancer cell XF498 were 8.24, 10.60, 8.83, $9.85\mug/ml$ respectively. GERI-BPO02-A has also revealed cytotoxicity against P-glycoproteinexpressed human colon cancer cell HCT15 and its multidrug-resistant subline HCT15/CL02, and its cytotoxicity was not affected by P-glycoprotein. We have also tested cytotoxicities of structurally related compounds of GERI-BPO02-A such as diphenylmethane, 1,1-bis(3,4dimethylphenyl)ethane, 2,2-diphenylpropane, 2-benzylpyridine, 3-benzylpyridine, $4,4^I-di-tert-butylphenyl$, bibenzyl, $2,2^I-dimethylbibenzyl$, cis-stilbene, trans-stilbene, 3-tert-butyl-4-hydroxy-5-methylphenyisulfide, sulfadiazine and sulfisomidine for studying of structure and activity relationship, and from these data we could suppose that hydroxyl group of GERI-BPO02A conducted important role in its cytotoxicity.

• Natural Product Sciences
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• 제10권6호
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• pp.315-320
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• 2004

Alpha-viniferin was previously isolated as a cyclooxygenase (COX)-2 inhibitor from Carex humilis (Cyperaceae) and is an oligomeric stilbene compound with benzofuran (BF) moieties in its chemical structure. In the present study, a chemically synthetic BF compound, named as 3,3-dimethyl-2,3,4,6,7,8,9,10,11,12,13,14,15,16,17,18-hexadecahydro-1H-benzo[b] cyclopentadeca[d]furan-1-one, was discovered to inhibit bacterial lipo polysaccharide (LPS)-induced prostaglandin $E_2$ $(PGE_2)$ production in macrophages RAW 264.7. The BF compound exhibited a selectively preferred inhibitory effect on COX-2 activity over COX-1 activity. Furthermore, BF compound inhibited LPS-induced COX-2 expression at transcription level. As a down-regulatory mechanism of COX-2 expression shown by BF compound, suppression of nuclear factor $(NF)-{\kappa}B$ activation has been demonstrated. BF compound inhibited LPS-induced $NF-{\kappa}B$ transcriptional activity and nuclear translocation of $NF-{\kappa}B$ p65, in parallel, but did not affect LPS-induced degradation of inhibitory ${\kappa}B{\alpha}$ protein $(I{\kappa}B{\alpha})$. Taken together, anti-inflammatory effect of BF compound on $PGE_2$ production was ascribed by its down-regulatory action on LPS-induced COX-2 synthesis in addition to inhibitory action on enzyme activity of COX-2.

• 대한한의학회지
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• 제19권1호
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• pp.89-99
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• 1998

약효(藥效) 및 안정성(安定性)이 입증(立證)된 한약(韓藥)으로부터 새로운 항균제(抗菌劑)를 도출(導出)하고자, 임상(臨床)에서 청열작용(淸熱作用)이 있거나 염증성(炎症性) 질환(疾患)과 박테리아의 감염(感染)으로 비롯된 질환(疾患)에 자주 쓰이는 22개(個)의 처방(處方)에 대(對)해 paper disk 법(法)을 사용(使用)하여 항균(抗菌) 효능(效能)을 검색(檢索)하였다. 시료(試料)는 한약(韓藥)의 고용(股用) 방법(方法)을 고려(考慮)하여 물로 추출(抽出)하였으며, 사용(使用) 균주(菌柱)로는 그람 양성균(陽性菌)인 포도상구균(葡萄狀球菌)과 고초균(枯草菌) 그리고 그람 음성균(陰性菌)인 대장균(大腸菌)과 녹농균(綠膿菌)을 사용(使用)하였고, 대조물질(對照物質)로는 tetracycline을 사용(使用)하여 상법(常法)에 의(依)해 실험(實驗)하였다. 22개(個)의 처방(處方) 가운데 백두옹탕(白頭翁湯), 황연해독탕(黃連解毒湯), 증황연황연해독탕(增黃連黃連解毒湯), 사심탕(瀉心湯), 용담사간탕(龍膽瀉肝湯), 선방활명음(仙方活命飮) 등(等)의 처방(處方)이 탁월(卓越)한 항균(抗菌) 활성(活性)을 보였다. 이 가운데 본(本) 연구(硏究)에서는 탕제(湯劑)의 구성(構成) 약재(藥材)가 다른 처방(處方)들에 비(比)해 비교적(比較的) 다양(多樣)한 선방활명음(仙方活命飮)에 대(對)해 활성(活性) 성분(成分)의 규명(糾明) 및 구성(構成) 약재간(藥材間)의 상화작용(相互作用)을 밝히고자 하였다. 선방활명음(仙方活命飮) 5 kg을 메탄올 (MeOH)로 추출(抽出)한 뒤 우수(優秀)한 항균(抗菌) 활성(活性)을 보인 에칠아세테이트 (EtOAc) 분획(分劃)에 대(對)하여 silica gel 및 Sephadex LH-20 column chromatography를 반복(反復)하여 stilbene 계열(系列)의 화합물(化合物)인 Rhapontigenin (Compound 1)과 Rhaponticin (Compound 2)을 얻었다. S. aureus SG 511에 대(對)해 Rhapontigenin은 50 mg/ml 이상(以上) 농도(濃度)에서 항균(抗菌) 효과(效果)를 나타내었고, Rhaponticin은 $200\;mg/m{\ell}$ 농도(濃度)에서 미약(微弱)하게 유효(有效)한 항균(抗菌) 효과(效果)를 나타내었으며, B. subtilis ATCC 6633에 대(對)해 Rhapontigenin은 50 mg/ml 이상(以上) 농도(濃度)에서 항균(抗菌) 효과(效果)를 나타내었고, Rhaponticin은 200 mg/ml 농도(濃度)에서 우수(優秀)한 항균(抗菌) 효과(效果)를 나타내었으며, 100 mg/ml 농도(濃度)에서 미약(微弱)하게 유효(有效)한 항균(抗菌) 효과(效果)를 나타내었다. 또한 E. coli 055에 대(對)해서는 Rhapontigenin과 Rhaponticin 모두 200 mg/ml 농도(濃度)에서 미약(微弱)하게 유효(有效)한 항균(抗菌) 효과(效果)를 나타내었다. 이상(以上)의 결과(結果)로 보아 선방활명음(仙方活命飮)의 항균(抗菌) 효능(效能)은 군약(君藥)인 대황(大黃)의 성분(成分) 중(中)의 하나인 stilbene 계열(系列)의 화합물(化合物)인 Rhapontigenin과 Rhaponticin의 작용(作用)에 의(依)한 것이며, 이는 한의학(韓醫學) 방제(方劑) 원리(原理)인 군신좌사(君臣佐使) 이론(理論)에서 군약(君藥)이 주증(主症)에 주(主)로 작용(作用)하는 약물(藥物)이라는 것을 밝혀주는 것이라고 사료(思料)된다.

• 대한화학회지
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• 제22권4호
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• pp.239-244
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• 1978

Stilbene 유도체인 trans-1,2-bispyrazylethylene에 대한 분광학적 연구를 행하였다. 보통의 자외선 흡수스펙트럼에서는 $n{\rightarrow}{\pi}^*$ 흡수밴드는 에너지가 비슷한 ${\pi}{\rightarrow}{\pi}^*$ 흡수밴드에 가려져서 나타나지 않는데 2차 미분 스펙트럼과 저온(77˚K)에서의 스펙트럼으로 부터 $n{\rightarrow}{\pi}^*$ 흡수 밴드를 확인할 수가 있었다. 또한 ${\pi}{\rightarrow}{\pi}^*$ 흡수밴드들의 전이에너지를 PPP-SCF-CI MO 방법으로 계산한 결과 스펙트럼에서 얻은 값과 잘 일치했다. 형광스펙트럼, 형광편광스펙트럼, 그리고 PPP-SCF-CI MO 방법에 의한 계산으로부터 형광을 내는 상태는 $^1({\pi},\;{\pi}^*)$ 상태임을 알 수가 있었으며 이것은 형광에 대한 alkaline salt effect의 결과와 일치한다.

• 약학회지
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• 제38권6호
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• pp.791-794
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• 1994

Sixteen kinds of naturally occurring phenolic compounds including 5 stilbenes, 7 flavonoids and 4 anthraquinones were examined in the inhibitory activity against rat liver AADC(aromatic L-amino acid decarboxylase) in vitro, using 5-hydroxytryptophan as a substrate. Three hydroxystilbenes, resveratrol 1, rhapontigenin 3 and piceatanol 5, which were known to be monoamine oxidase A inhibitors, exhibited a significant inhibition against AADC($IC_{50}$=20, 8 and $5\;{\mu}M$, respectively). By the comparison of the activity of each phenolic compound, it was suggested that the 3',4'-dihydroxyphenyl group of stilbenes or flavones was the best pharmacophore for the AADC inhibitory activity.

• Natural Product Sciences
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• 제20권2호
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• pp.91-94
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• 2014

Column chromatographic separation of the MeOH extract from the tubers of Bletilla striata yielded seven phenolic components including four phenanthrenes, 3,7-dihydroxy-2,4-dimethoxyphenanthrene (1), 3,7-dihydroxy-2,4,8-trimethoxyphenanthrene (2), 9,10-dihydro-4,7-dimethoxyphenanthrene-2,8-diol (3), and 9,10-dihydro-1-(4'-hydroxybenzyl)-4,7-dimethoxyphenanthrene-2,8-diol (4) and three stilbenes, gigantol (5), 3',4"-dihydroxy-5',3",5"-trimethoxybibenzyl (6), and batatasin III (7). Their structures were determined on the basis of NMR spectroscopic data. Among them, compound 2, 3, and 6 were reported for the first time from this plant. The isolated compounds (1-7) were tested for cytotoxicity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay.

• 대한화학회지
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• 제21권2호
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• pp.102-107
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• 1977

질소를 방향족고리에 포함하고 있는 헤테로 화합물인 트란스-1,2-비스피라질 에틸렌을 쿠멘, 이소프로판올, 시멘용매등에 녹여 빛을 쪼여준 결과 광화학적 환원이 일어나 1,2-비스피라질 에탄이 됨을 알았다. 알칼리 금속염이 이 환원반응에 미치는 영향, 용매효과, 증감제와 아줄렌등의 영향으로 부터 이 환원 반응은 $(n,{\pi}^*)^1$상태로부터 일어남을 알았다.