• 제목/요약/키워드: Stilbene glycosides

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

  • 송홍근
    • Journal of the Korean Wood Science and Technology
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    • 제29권4호
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    • pp.97-102
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    • 2001
  • 약 25년 생 잣나무 수피 추출물중 EtOAc용해분에 함유된 화합물을 단리 동정하였다. 화합물의 단리는 Sephadex-LH20과 TSK-gel HW-40F를 충전제로 한 Column chromatography로 하였다. 단리된 화합물의 구조동정은 $^1H{\cdot}^{13}C$-NMR, HMQC, HMBC등과 $FAB^+$ MS 등을 이용하여 결정하였다. 새로이 동정된 화합물은 Z-pinostilbenoside, E-desoxyrhaponticin, 그리고 E-resveratroloside 등이었다.

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

  • 최성진
    • 원예과학기술지
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    • 제29권4호
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    • pp.374-381
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    • 2011
  • Stilbene 화합물은 항산화 및 항균 활성을 가지는 폴리페놀계의 천연물이다. 포도를 포함하는 몇몇 종류의 식물에서 stilbene 화합물은 resveratrol의 유도체로서 매우 다양한 형태로 존재한다. 자외선 조사 포도 잎에서 stibene 화합물을 정량 분석하기에 앞서, 먼저 각 stilbene 화합물을 동정하기 위한 실험을 수행하였다. 이를 위하여, 자외선을 심하게 조사한 잎에서 stilbene 배당체를 추출하였다. 추출한 배당체 시료는 ${\beta}$-glucosidase를 이용하여 가수분해한 후, 특정 stilbene 화합물의 질량에 해당하는 m/z에서 HPLC-mass spectrometer를 이용하여 분석하였다. 효소적 가수분해에 의해 chromatogram상에는 glycoside에 해당할 것으로 예상되는 peak의 감소와 aglycone에 해당할 것으로 예상되는 peak 증가가 나타났다. 또한 stilbene 화합물의 광 이성질화를 유도하기 위하여 시료를 일광에 노출하였으며, 광 노출에 의해 trans-isomer에 해당할 것으로 예상되는 peak의 소멸과 cis-isomer에 해당할 것으로 예상되는 peak의 생성이 나타났다. Chromatogram상의 peak의 이러한 증감으로부터 각 peak의 성분을 유추하였다. 이러한 방법으로 포도 잎에서 16종의 stilbene 화합물을 동정할 수 있었으며 자외선을 조사한 포도 잎에서 동정된 화합물에 대한 정량적 분석을 수행하였다. 자외선 조사는 포도 잎에서 총 stilbene 함량의 상당한 증가를 가져왔는데 특히 trans-resveratrol은 수백 배 증가하였다. 또한, resveratrol보다 더 강한 radical 소거 활성을 가지지만 무처리 잎에서는 단지 미량으로만 존재하는 piceatannol의 함량 역시 수십배 증가하였다. 자외선 조사에 의한 이러한 stilbene 함량의 증가는 hormesis 현상으로서 포도의 스트레스 대응 반응의 하나로 생각된다.

$5{\alpha}-Reductase$ 활성에 미치는 종대황 스틸벤 유도체의 영향 (Effects of Stilbene Derivatives from Rheum undulatum on $5{\alpha}-Reductase$ Activity)

  • 고성권
    • 생약학회지
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    • 제31권2호
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    • pp.245-248
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    • 2000
  • As a series of the studies on cultivated Korean rhubarb rhizomes (Rheum undulatum), five stilbene derivatives were screened for inhibitory activity against $5{\alpha}-reductase$. Of these, desoxyrhapontigenin, rhapontigenin, and piceatannol exhibited inhibition, whereas, two other stilbene glycosides, rhaponticin and $piceatannol-3'-O-{\beta}-D-glucopyranoside$ did not show the inhibition.

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Carrageenan 유발 족부종에 미치는 종대황 스틸벤 유도체의 효과 (Effect of Stilbene Derivatives from Rheum undulatum on Carrageenan-Induced Acute Edema in Rats)

  • 고성권;신차균;이학성;한성태;양병욱;임병옥;정성현
    • 생약학회지
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    • 제35권2호통권137호
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    • pp.171-174
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    • 2004
  • In order to examine the anti-ohyul (anti-inflammatory) activity of rhubarb, we investigated the effects of stilbene derivatives obtained from rhizomes of Rheum undulatum on the carrageenan-induced hind paw edema in rats. Administration of stilbene aglycon (rhapontigenin) at doses of 50 and 100 mg/kg exhibited the anti- edema effect in dose dependent manner and stilbene glycosides $(rhaponticin,\;piceatannol-3'-O-{\beta}-D-glucopyranoside)$ at a dose of 100 mg/kg also showed inhibitory effect on the carrageenan-induced edema. These inhibitory effects may ascribed, at least in part, to the anti-ohyul activity of rhubarb.

Natural Compounds with Antioxidant Activity: Recent Findings from Studies on Medicinal Plants

  • Na, Min-Kyun;Thuong, Phuong Thien;Bae, Ki-Hwan
    • Natural Product Sciences
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    • 제17권2호
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    • pp.65-79
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    • 2011
  • Reactive oxygen species potentially cause damage to cellular components including lipids, protein and DNA; this oxidative damage plays a key role in the pathogenesis of neurodegenerative disease, cardiovascular disease, metabolic disease and cancer. On the basis of the oxidative stress hypothesis, a number of studies have been performed to search for an efficient and safe antioxidant. Although in vitro studies have provided promising results, only a limited number of natural and synthetic antioxidants have been developed for clinical application due to their low efficacy and side-effects. Thus, the discovery of new antioxidants with marked efficacy and safety has attracted worldwide attention in recent decades. Since plants are recognized as important sources of natural antioxidants, our research has focused on the discovery of new naturally occurring antioxidants from medicinal plants. The purpose of this review is to open a new prospect in the field of search for natural antioxidants from medicinal plants by summarizing our recent findings. Using in vitro bioassay systems such as 2,2-diphenyl-1-picrylhydrazyl, superoxide radical scavenging tests and lipid peroxidation models, we have tested over than 350 species of medicinal plants for their antioxidant activity and selected several of them for further investigation. During the research on the discovery of effective natural antioxidants from the medicinal plants selected, we have isolated several new and known antioxidant compounds that include stilbene glycosides, phenolic glycosides, flavonoids, oligostilbenes, and coumarins. Our results suggest that the presence of antioxidant compounds in the medicinal plants might be associated with the traditional use to treat inflammation, cardiovascular disease and various chronic diseases.

Comparison of the Permeability of Stilbene Analogues in Caco-2 Cells

  • Kim, Su-Na;Ahn, Ji-Yun;Shon, Dong-Wha;Kim, Ji-Sun;Kim, Mi-Hye;Ha, Tye-Youl
    • 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.