• Title/Summary/Keyword: stilbene 화합물

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The Identification of Stilbene Compounds and the Change of Their Contents in UV-irradiated Grapevine Leaves (자외선 조사 포도 잎에서 Stilbene 화합물의 동정과 함량의 변화)

  • Choi, Seong-Jin
    • Horticultural Science & Technology
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    • v.29 no.4
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    • pp.374-381
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    • 2011
  • Stilbenes are polyphenolic natural products, which have antioxidative and antifungal activities. In some plants, including grapevine, the stilbene compounds, as resveratrol derivatives, exist in very diverse forms. Experiments to identify the individual stilbene compounds were carried out first to quantify them in UV-irradiated grapevine leaves. For this, stilbene glycosides were extracted from grapevine leaves which irradiated intensively with UV light. The glycoside samples were hydrolyzed by ${\beta}$-glucosidase, before analyzed by HPLC-mass spectrometer at each m/z corresponding to the mass of specific stilbenes. As results, in chromatograms, the enzymatic hydrolysis resulted in decrease and increase of the peaks expected for glycosides and aglycones, respectively. The samples were also exposed to sunlight in order to photo-isomerize the stilbene compounds. The light exposure resulted in disappearance and appearance of peaks expected for trans- and cis-isomers of stilbenes, respectively. Such a change of the peaks in chromatograms provided information needed for the inference to peak components. In this way, it was possible to identify 16 kinds of stilbene compounds from grapevine leaves. The identified stilbenes were quantified from grapevine leaves irradiated mildly by UV light. The UV-irradiation increased markedly in the content of stilbene compounds, especially trans-resveratrol by several hundredfold. In addition, piceatannol, which is a mere minor component of stilbenes in control leaves and a more active radical scavenger than resveratrol, was also increased by several tenfold by the treatment. The increase in stilbene contents as influenced by UV irradiation seems to be one of the stress coping responses of grapevine as a hormesis phenomenon.

Isolation and Identification of Stilbene glycosides from the Bark of Pinus koraiensis (잣나무 수피의 Stilbene glycosides의 분리 및 동정)

  • Song, Hong-Keun
    • Journal of the Korean Wood Science and Technology
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    • v.29 no.4
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    • pp.97-102
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    • 2001
  • EtOAc extract from the bark of Pinus koraiensis Sieb. et Zucc was isolated by column chromatography which was packed with Sephadex LH-20 or TSK-gel HW-40F. Several stilbene glycosides were identified by $^1H{\cdot}^{13}C$-NMR, HMQC, HMBC and $FAB^+$ MS. Three stilbene glycosides, Z-pinostilbenoside, E-desoxyrhaponticin, and E-resveratroloside, were identified.

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The Influence of UV Irradiation on Stilbene Contents and Gray Mold Incidence in Grapevine Leaves (자외선 조사가 포도잎의 Stilbene 함량 및 잿빛곰팡이병 발생에 미치는 영향)

  • Choi, Seong-Jin
    • Horticultural Science & Technology
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    • v.30 no.5
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    • pp.493-500
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    • 2012
  • In order to confirm the possibility of UV utilization as a means for disease protection in grapevine the stilbene contents and the disease incidence in UV irradiated leaves were investigated. UV irradiation significantly increased the contents of resveratrol, piceatannol and piceid, in them, resveratrol and piceid showed in vitro inhibition of spore germination and mycelium growth of Botrytis cinerea. The accumulation of both the stilbenes in UV irradiated leaves seems to be enough to inhibit the B. cinerea growth, since the formation of necrotic spot on the leaves was considerably inhibited when they were inoculated with the conidial spores of B. cinerea. However the stilbenes were accumulated only in the leaves exposed directly to UV showing a limited translocation ability of the compounds. Thus it would be necessary to develop a method to evenly irradiate the entire crown of plant with UV in order to expect to protect them from disease by UV irradiation.

Characteristics of Cold Hardiness and Growth of Grapevines Grown under Rain Shelter Type Cultivation System in the Vineyard (간이비가림시설에서의 포도 내한성 발현 및 생육 특성)

  • Ahn, Soon Young;Kim, Seung Hui;Choi, Sung Jin;Yun, Hae Keun
    • Horticultural Science & Technology
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    • v.30 no.6
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    • pp.626-634
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    • 2012
  • There are variations among grapevine genotypes in the levels of tolerance to cold, and cold-hardiness of grapevine has been affected by the change of short-term environment during over-wintering. In this study, the responses of vines to cold in open field and rain-shelter system were investigated to obtain useful information in increasing the tolerance to cold in grape cultivation. Total carbohydrate content of bearing mother branches was higher in the rain-shelter system than in the open field, and lower in the branches of 'Muscat Bailey A' than in 'Campbell Early' and 'Kyoho'. Bud-burst and shoot growth were better in the rain-shelter system than in open field, whereas there is no significant difference among the treatments of net beside vines. There was also low incidence of gray mold in rain shelter system. Stilbene compounds such as t-piceid, resveratrol, piceatannol, c-piceid were accumulated in the cold-treated shoot from vine cuts harvested in rain shelter system. Genes of chalcone isomerase, manganese superoxide dismutase, proline rich protein 2, and temperature induced lipocalin were highly expressed in the cold-treated shoot from vine cuts harvested in rain shelter system. While there was not change of air temperature, but high reduction of wind speed in the rain shelter system compared to open field, and increase in the reduction of wind speed by net treatment. The damage of grapevines by cold in the extreme low temperature could be reduced by keeping them in the rain shelter system with net during winter season.

Antilipoperoxidant Activity of Antraquinone and Stilbene from Polygonum cuspidatum (호장으로부터 분리한 안트라퀴논 및 스틸벤 화합물의 지질과산화 저해활성)

  • Joo, Si-Mong;Lee, Min-Won;Yang, Ki-Sook
    • YAKHAK HOEJI
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    • v.51 no.2
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    • pp.140-144
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    • 2007
  • Polygonum cuspidatum has been used as treatments of dermatitis, gonorrhea, inflammation, and hyperlipidaemia in traditional medicine. We examined liver protective effect on CCl$_4$ inducing hepatotoxicity and anti-oxidative activity by TBA method. Phytochemical examination of Polygonum cuspidatum led to the isolation and characterization of emodin 8-O-${\beta}$-D-glucopyranoside (compound 1), and trans-resveratrol 3-O-${\beta}$-D-glucopyranoside (compound 2). Compounds 1 and 2 enhanced the inhibition of anti-lipid peroxidative effects in liver homogenate. In chemical parameters obtained from serum analysis, compounds 1 and 2 also revealed significant decrease in hepatotoxicity. These results suggested that the antraquinone and stilbene which were isolated from Polygonum cuspidatum might be used as therapeutic agent of hepatitis.

Studies on the Antibacterial Activity and Active Constituents of Sonbanghwalmyoungum (선방활명음(仙方活命飮)의 항균효능(抗菌效能) 및 성분(成分)에 관(關)한 연구(硏究))

  • Lee, Beom-Yong;Ahn, Duk-Kyun;Woo, Eun-Rhan;Park, Ho-Koon
    • The Journal of Korean Medicine
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    • v.19 no.1
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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.

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Inhibition of Aromatic L-Amino Acid Decarboxylase (AADC) by Some Phenolic Compounds from Medicinal Plants (천연 페놀성 화합물들의 방향족 아미노산 탈탄산효소 저해작용)

  • Ryu, Shi-Yong;Han, Yong-Nam;Han, Byung-Hoon
    • YAKHAK HOEJI
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    • v.38 no.6
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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.

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Photochemical Reduction of trans-1,2-Bispyrazylethylene (트란스-1,2-비스피라질에틸렌의 광화학적 환원)

  • Sang Chul Shim;Jeong Seok Chae
    • Journal of the Korean Chemical Society
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    • v.21 no.2
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    • pp.102-107
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    • 1977
  • Photochemical reduction of 1,2-bispyrazylethylene,a stilbene like heterocompound, was studied in hydrogen donating solvents and reduction product, 1, 2-bispyrazylethane, was identified. Salt and solvent effects on the quantum yields of the reduction, sensitization and quenching studies showed that the reactive state for the photochemical reduction of the compound is $(n,{\pi}^*)^1$ state rather than $({\pi},{\pi}^*)^1$ state.

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Preparation of Liquefied Cellulose and Analysis of Its Components by GC-MS Spectrometry (액화셀룰로오스의 제조 및 GC-MS에 의한 그 성분 분석)

  • 조국란;황병호;공영토;도금현
    • Journal of Korea Foresty Energy
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    • v.19 no.2
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    • pp.86-92
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    • 2000
  • The liquefactions of $\alpha$-cellulose(Sigma Chemical, C-8002, 47H0383) was prepared in the presence of phenol using sulfuric acid as a catalyst under $N_2$ gas protection at $180^{\circ}C$ for 60minutes to examine its components. The ratio of $\alpha$-cellulose to phenol was 1: 6.2(w/w), and that to sulfuric acid was 1: 0.05(g/$m\ell$). The yields of liquefaction were calculated after the liquefied mixtures were passed through 1G4 glass filter. The luquefied product of $\alpha$-cellulose was analyzed using GC-MS Spectormeter. The 12 compounds identified by GC-MS Spectrometer, of which peak area covers 54% as 2,4-dimethyl phenol, p-isopropyl phenol, 1-ethyl-3,5-dimethyl benzene, o-isopropyl phenol, (E)-2,4\` dihydroxy-stilbene, 2,2\`-methylene-bisphenol, 4,4\`-methylenebisphenol, 3-methyl-2-hydroxyphenyl-(E)-2-hydroxyl-4\`-methoxy-stilbene, 1-phyenyl-1-(4\`hydroxyphenyl)methanol phenol derivatives. From this results, the reaction pathways of the liquefaction of cellulose were proposed through electrophilic substitution reaction. Phenol as a solvent might react with the reaction intermediates as well in the cellulose liquefaction.

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Anti-obesity effect of Ramulus mori extracts and stilbenes in high fat dietfed C57BL/6J mouse (고지방식이를 급여한 C57BL/6J 마우스에서 상지추출물과 스틸벤 화합물의 항비만 효능 연구)

  • Park, Jeong-Eun;Lee, Geon-Hee;Kim, Juhee;Choi, Sang-Won;Kim, Eunjung
    • Journal of Nutrition and Health
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    • v.53 no.6
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    • pp.570-582
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    • 2020
  • Purpose: Obesity is a risk factor for various adult diseases such as type 2 diabetes, cardio-cerebrovascular disease, and cancer. With an increasing obesity population worldwide, the prevention of obesity with natural components has emerged as an alternative health care strategy. Ramulus mori (Sangzhi, RM) is widely used as a traditional herbal medicine in East Asia. It contains various phytochemicals, including stilbenes and 2-arylbenzofurans. In this study, we compared the anti-obesity effects of RM extracts and its major stilbene components (mulberroside A [MSA] and oxyresveratrol [ORT]) in high fat diet (HFD)-fed obese mice. Methods: Five week-old, male C57BL/6J mice were grouped into 7 experimental groups: normal diet (ND), HFD, HFD + 1% RM water extracts (MW), HFD + 0.1% MSA, HFD + 1% RM ethanol extracts (ME), HFD + 0.1% ORT, and HFD + 1% Garcinia cambogia extracts (GC) as a positive control. All mice were fed experimental diet for 13 weeks. Results: Compared to the HFD group, total body weight and weekly body weight gain were significantly decreased in the ME, ORT, and GC groups. Glucose tolerance level was significantly decreased in all experimental groups, whereas plasma insulin level was decreased in MSA, ME, ORT and GC groups. Plasma glucose, triglyceride (TG), and total cholesterol levels were significantly decreased, whereas high-density lipoprotein cholesterol levels were increased in the MSA, ORT, and GC groups. Hepatic TG accumulation was also significantly decreased in the MSA, ME, ORT, and GC groups. Adipose tissue weight and size of adipocytes were significantly decreased in the MSA, ME and ORT groups, and were comparable to values obtained in the GC group. The levels of adiponectin and SREBP1c mRNA expressions were increased in the ORT and GC groups. Conclusion: These results indicate that ME, ORT and MSA exert significant anti-obesity effect, and have the potential to be developed as a weight control ingredient of functional foods.