• Journal of Microbiology and Biotechnology
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• 제22권12호
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• pp.1698-1704
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• 2012

Resveratrol, or its glycoside form piceid, is a dietary antioxidant polyphenolic compound, found in grapes and red wine that has been shown to have protective effects against cardiovascular disease. However, very low water solubility of the compound may limit its application in the food and pharmaceutical industries. The amylosucrase (AMAS) of Alteromonas macleodii Deep ecotype was expressed in Escherichia coli and showed high glycosyltransferase activity to produce the glucosyl piceid when piceid was used as an acceptor. The conversion yield of piceid glucoside was 35.2%. Biotransformation using culture of the E. coli harboring the amas gene increased the yield up to 70.8%. The transfer product was purified by reverse phase chromatography and recycling preparative HPLC, and the molecular structure of the piceid glucoside was determined using NMR spectroscopy. The piceid glucoside was identified as glucosyl-${\alpha}$-($1{\rightarrow}4$)-piceid. The solubility of glucosyl piceid was 5.26 and 1.14 times higher than those of resveratrol and piceid, respectively. It is anticipated that dietary intake of this compound is more effective by enhancing the bioavailability of resveratrol in the human body because of its hydrophilic properties in the intestinal fluid.

• Journal of Microbiology and Biotechnology
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• 제31권12호
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• pp.1692-1700
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• 2021

Glycosylation of resveratrol was carried out by using the amylosucrase of Deinococcus geothermalis, and the glycosylated products were tested for their solubility, chemical stability, and biological activities. We synthesized and identified these two major glycosylated products as resveratrol-4'-O-α-glucoside and resveratrol-3-O-α-glucoside by nuclear magnetic resonance analysis with a ratio of 5:1. The water solubilities of the two resveratrol-α-glucoside isomers (α-piceid isomers) were approximately 3.6 and 13.5 times higher than that of β-piceid and resveratrol, respectively, and they were also highly stable in buffered solutions. The antioxidant activity of the α-piceid isomers, examined by radical scavenging capability, showed it to be initially lower than that of resveratrol, but as time passed, the α-piceid isomers' activity reached a level similar to that of resveratrol. The α-piceid isomers also showed better inhibitory activity against tyrosinase and melanin synthesis in B16F10 melanoma cells than β-piceid. The cellular uptake of the α-piceid isomers, which was assessed by ultra-performance liquid chromatography (UPLC) analysis of the cell-free extracts of B16F10 melanoma cells, demonstrated that the glycosylated form of resveratrol was gradually converted to resveratrol inside the cells. These results indicate that the enzymatic glycosylation of resveratrol could be a useful method for enhancing the bioavailability of resveratrol.

• 원예과학기술지
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• 제30권5호
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• pp.493-500
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• 2012

포도 잎에서 병 발생을 경감하기 위한 수단으로 자외선의 활용 가능성을 확인하기 위하여, 자외선을 조사한 포도 잎에서 stilbene 화합물의 함량 변화와 Botrytis cinerea 생장의 차이를 조사하였다. 자외선의 조사는 포도 잎에서 resveratrol, piceatannol, piceid의 함량을 크게 증가시켰으며, 특히 resveratrol과 piceid는 B. cinerea의 포자 발아와 균사 생장을 억제하는 효과를 보였다. 자외선 조사에 의해 포도 잎에 축적되는 resveratrol과 piceid의 농도는 B. cinerea의 생장을 억제하기에 충분할 것으로 생각되며 자외선을 조사한 포도 잎에 B. cinerea의 포자를 접종하였을 때 괴사 반점의 형성이 억제되는 것으로 나타났다. 그러나 stilbene 화합물은 체내 이동성이 거의 없고 자외선에 직접 노출된 잎에서만 함량이 증가하므로 병 발생 경감의 수단으로 자외선을 활용하기 위해서는 수관 전체에 자외선을 균일하게 조사하는 방법의 도입이 필요해 보인다.

• Food Science and Biotechnology
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• 제17권3호
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• pp.675-678
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• 2008

Permeability of resveratrol, piceid, rhapontigenin, and rhaponticin in Caco-2 cell assays using high-performance liquid chromatography were compared. Caco-2 cell monolayers were used to evaluate the transport rates of stilbene analogues from the apical to the basolateral sides. All stilbenes experimented in this study were transported to the basolateral side by times. For comparing the permeability of 4 stilbenes, we calculated the slope of the cumulative concentration of each stilbene in basolateral sides over time, resulting in those values of resveratrol, piceid, rhapontigenin, and rhaponticin with $3.766{\times}10^{-5}$, $4.330{\times}10^{-6}$, $5.430{\times}10^{-5}$, and $2.458{\times}10^{-5}\;{\mu}M/sec$, respectively. Apparent permeability coefficient of resveratrol and rhapontigenin were calculated to $9.994{\times}10^{-6}$ and $1.441{\times}10^{-6}\;cm/sec$, respectively, while those of piceid and rhaponticin were to $1.149{\times}10^{-7}$ and $6.523{\times}10^{-7}\;cm/sec$, respectively. These results suggest that aglycones would be absorbed more effectively than glycosides in stilbenoids.

• 식물병연구
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• 제19권3호
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• pp.177-182
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• 2013

Resvestrol has been known to inhibit bacterial and fungal growth in vitro, and can be accumulated in plant to concentrations necessary to inhibit microbial pathogens. Hence, stilbene synthase gene has been used to transform to synthesize resveratrol in heterologous plant species to enhance resistance against pathogens. In the present study, we investigated the antimicrobial activities of resveratrol and piceid to bacterial and fungal pathogens, which causing severe damages to rice plants. In addition, disease resistance was compared between transgenic rice varieties, Iksan 515 and Iksan 526 transformed with stlibene synthase gene and non-transgenic rice varieties, Dongjin and Nampyeong. Minimum inhibitory concentration of resveratrol for Burkolderia glumae was 437.5 ${\mu}M$, and the mycelial growth of Biplaris oryzae was slightly inhibited at concentration of 10 ${\mu}M$. However, other bacterial and fungal pathogens are not inhibited by resveratrol and piceid. The expression of the stilbene synthase gene in Iksan 515 and Iksan 526 did not significantly enhanced resistance against bacterial grain rot, bacterial leaf blight, sheath blight, and leaf blight. This study is the first report on the effect of resveratrol and piceid against pathogens of rice plant, and changes of disease resistance of transgenic rice plants transformed with stilbene synthase gene.

• 한국식품영양과학회지
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• 제37권1호
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• pp.124-128
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• 2008

본 연구는 DAD/UV HPLC를 이용하여 뽕잎과 오디(Morus alba L.)에 함유되어 있는 stilbenoids의 조성과 함량을 분석하고자 수행되었다. 뽕잎과 오디추출물을 DAD를 이용하여 최대흡광파장을 탐색한 결과 308 nm로 나타났으며, stilbenoids 조성이 오디에는 resveratrol, piceatannol, rhapontigenin, astringin, pterostilbene, piceid, rhaponticin, 뽕잎에는 resveratrol, rhapontigenin, pterostilbene, piceid이 함유된 것으로 나타났다. 오디와 뽕잎의 총 stilbenoids 함량은 $609.15{\pm}7.24$ mg/100 g d.w.와 $188.57{\pm}1.70$ mg/100 g d.w.였으며, rhaponticin은 오디($389.26{\pm}5.22$ mg/100 g d.w.)와 뽕잎($99.17{\pm}2.79$ mg/100 g d.w.) 모두 가장 많은 함량이 함유되어 있었다. Astringin과 piceatannol은 오디에서만 검출되었으며 vitisin A는 모두 검출되지 않았다. Piceid와 rhaponticin은 이의 비배당체인 resveratrol과 rhapontigenin보다 과량 함유되어 있어 비배당체보다는 배당체의 함량이 높은 것으로 나타났다.

• Archives of Pharmacal Research
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• 제17권1호
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• pp.42-44
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• 1994

The activity-guided fractionation of some medicinal plants led to yield five kinds of natural stilbene compounds namely 3, 5-dihydroxy-4'-methoxystillbene(I), rhapontigenin(II), reveratrol(III), rhaponticin(IV) and piceid(V) and two common flavonoids, apigenin(VI) and luteolin(VII) as active principles of the antitumor property, in vitro, against five kinds of human tumor cell lines, A-549, SK-OV-3, SK-MEL-2, XF-498 and HCT15.

• Bulletin of the Korean Chemical Society
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• 제24권11호
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• pp.1680-1682
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• 2003

• 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.

• Archives of Pharmacal Research
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• 제21권6호
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• pp.703-706
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• 1998

The anticomplementary activity of stilbenes from medicinal plants in Korea was investigated in vitro. 3,5-Dihydroxy-4'-methoxystilbene (3) was most potent with $IC_{50}$ value of $1.5{\times}10^{-4}M$ followed by rhapontigenin (4), oxyresverastrol (2), 2,3,4',5-tetrahydroxystilbene-2-O-beta-glucoside (9), rhaponticin (8), resverastrol (1), and piceid (7). The activity was found to be increased by a methylation on a hydroxy group of C-4' of 1, but decreased by further methylation on hydroxy groups of C-3 and C-5 and glucosylation on any hydroxy group of 1. Addition of hydroxy group on C-2' of 1 or C-3' of 3 was little affected on the anticomplementary activity but the activity was increased by O-glucosylation on C-2 of 1.