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- 주제어 : Dimethoxycurcumin (검색결과 5 건)
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Curcumin 유도체 및 대사체가 산화스트레스에 의한 HepG2 세포 독성에 미치는 영향
김기병 ( Ki Byoung Kim ),이수경 ( Su Kyung Lee ),권영달 ( Young Dal Kwon ),염승룡 ( Seung Ryong Yeom ),송용선 ( Yung Sun Song ) 한방재활의학과학회 2010 한방재활의학과학회지 Vol.20 No.2
Objectives: The purpose of this study was to investigate antioxidant effects of curcumin from Curcumae Longae Radix. Methods :Using HepG2 liver-like cells, the antioxidant effects of curcumin, one of main components from Curcumae Longae Radix, and its analogues have been evaluated by measuring their effects on cytotoxicity induced by H2O2. Results :The pre-incubation for 6 hours with curcumin, bis-demethoxycurcumin, or dimethoxycurcumin protected HepG2 cells from H2O2-induced toxicity in a dose-dependent manner. However, tetrahydrocurcumin, one of curcumin metabolites, did not protect HepG2 cells from H2O2-induced toxicity. Interestingly, curcumin, bis-demethoxycurcumin, and dimethoxycurcumin were increased in the protein levels of heme oxygenase-1(HO-1) at concentrations that were also effective in cellular protection. In contrast, tetrahydrocurcumin did not induce HO-1 expression. Tin protoporphyrin-IX, an inhibitor of HO-1 activity, significantly abolished cytoprotection afforded by curcumin, bis-demethoxycurcumin and dimethoxycurcumin. Conclusions :These results demonstrate that curcumin, bis-demethoxycurcumin, and dimethoxycurcumin with two conjugated doble bonds on their structures may reduce H2O2-induced oxidative stress through HO-1 expression. HO-1 induction may be one of antioxidant pathways by which curcumin protects from oxidative stress-induced cytotoxicity.
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Jeong, Sun-Oh,Oh, Gi-Su,Ha, Hun-Yong,Soon Koo, Bon,Sung Kim, Hak,Kim, Youn-Chul,Kim, Eun-Cheol,Lee, Kang-Min,Chung, Hun-Taeg,Pae, Hyun-Ock the Society for Free Radical Research Japan 2009 Journal of clinical biochemistry and nutrition Vol.44 No.1
<P>Curcumin [1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione] induces heme oxygenase-1 (HO-1) expression via activation of the nuclear factor-erythroid-2-related factor 2 (Nrf2), whereas tetrahydrocurcumin [1,7-bis(4-hydroxy-3-methoxyphenyl)-3,5-heptanedione], one of curcumin <I>in vivo</I> metabolites, has no effect on HO-1 expression and Nrf2 activation. The aim of this study was to investigate whether dimethoxycurcumin [1,7-bis(4,3-dimethoxyphenyl)-1,6-heptadiene-3,5-dione], a synthetic curcumin analogue with higher metabolic stability over curcumin, could induce HO-1 expression to the same extent as curcumin in RAW264.7 macrophages. Dimethoxycurcumin and curcumin, but not tetrahydrocurcumin, induced HO-1 expression and Nrf2 nuclear translocation, suggesting that the unsaturated nature of the diarylheptanoid chain of the compounds are crucial for HO-1 expression and Nrf2 activation. Blockage of Nrf2 synthesis by small interfering RNA abolished HO-1 expression by dimethoxycurcumin, indicating that dimethoxycurcumin may induce HO-1 expression via Nrf2 activation. In comparison, dimethoxycurcumin and curcumin had about the same effect on HO-1 expression, suggesting that dimethoxycurcumin retains the HO-1-inducing activity of its parent compound curcumin in RAW264.7 macrophages.</P>
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이재환,홍혜민,권동득,배현옥,정희종 대한비뇨의학회 2010 Investigative and Clinical Urology Vol.51 No.12
Purpose: Curcumin (Cur) has been reported to induce apoptosis in human renal carcinoma Caki cells. Dimethoxycurcumin (DMC), one of several synthetic Cur analogues, has been reported to have increased metabolic stability over Cur. We determined whether DMC, like Cur, induces apoptosis in Caki cells and also compared the apoptosis-inducing activity of DMC with that of Cur. Materials and Methods: Caki cells were treated with DMC possessing four methoxy groups, Cur possessing two methoxy groups, or bis-demethoxycurcumin (BMC), which lacks a methoxy group. Cell viability was measured by using a methyltetrazolium assay. Flow cytometry and the caspase-3 activity assay were used to detect apoptosis. The release of cytochrome-c (Cyt c) was detected by Western blot analysis. The production of reactive oxygen species (ROS) was measured by flow cytometry. Results: DMC, Cur, and BMC reduced cell viability and induced apoptosis, but the potency varied; DMC was the most potent compound, followed by Cur and BMC. ROS production, Cyt c release, and caspase-3 activity were increased, again in the order DMC>Cur>BMC. N-Acetylcysteine, a potent antioxidant, inhibited ROS production, Cyt c release, caspase-3 activation, and apoptosis induction in DMC-treated cells. Conclusions: These results indicate that DMC, like the original form of Cur, may induce apoptosis in human renal carcinoma Caki cells through the production of ROS, the release of mitochondrial Cyt c, and the subsequent activation of caspase-3. In addition, DMC is more potent than Cur in the ability to induce apoptosis.
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Dimethoxycurcumin 및 curcumin 합성유도체가 RAW264.7 대식세포의 nitric oxide 생성에 미치는 효과
박성혁 ( Seong Heak Park ),신병철 ( Byung Cheul Shin ),권영달 ( Young Dal Kwon ),송용선 ( Yung Sun Song ) 한방재활의학과학회 2008 한방재활의학과학회지 Vol.18 No.1
목 적 : 급성 및 만성 염증 질환은 iNOS에 의해서 생성된 과량의 NO와 관련이 있다. 따라서 이러한 질병 치료를 목적으로 NO 생성 억제물질 또는 iNOS 발현 차단물질을 개발할 가치가 있다. 본 연구는 대사 안정성을 개선시킨 dimethoxycurcumin (DiMC)이 활성화된 대식세포에서 NO 생성 및 iNOS 발현을 제어할 수 있는지 조사하였다. 방 법 : RAW264.7 세포를 DiMC (양쪽 방향성 고리에 각각 2개의 methoxy group을 가짐), curcumin (양쪽 방향성 고리에 각각 1개의 methoxy group을 가짐), bis-demethoxycurcumin (양쪽 방향성 고리에 methoxy group이 없음; BDMC) 및 tetrahydrocurcumin (양쪽 방향성 고리에 각각 1개의 methoxy group을 가지고 있지만 중앙 7개 탄소 사슬에 이중결합이 없음; THC)로 각각 전처리한 후에 LPS로 자극하였다. 이들 전처리 물질의 효과를 비교하기 위하여, NO 생성, iNOS 발현, NF-kB p65 인산화 및 p65 DNA-binding 활성을 조사하였다. 결 과 : DiMC, curcumin 및 BDMC는 NO 생성, iNOS 발현 및 NF-kB 활성을 억제하였으며, 그 세기에 있어서 DiMC가 가장 크게 관찰되었고 그 다음 curcumin 그리고 BDMC 순으로 관찰되었다. THC는 어떠한 활성도 보이지 못했다. 결 론 : DiMC는 NO 생성 억제, iNOS 발현 차단 및 NF-kB 비활성을 유도할 수 있음을 알 수 있었다. 이러한 효과는 연속된 이중결합 및 methoxy group의 증가와 관련이 있는 것으로 판단된다.
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Jeong, Seon-Choong,Chong, Myong-Soo,Koo, Bon-Soon,Pae, Hyun-Ock,Chung, Hun-Taeg,Lee, Ki-Nam Society of Preventive Korean Medicine 2007 대한예방한의학회지 Vol.11 No.1
Curcumin and its analogues(Tetrahydrocurcumin THC, demethoxycurcumin ; BDMC and dimethoxycurcumin DiMC) were compared for their ability to inhibit the growth of human leukemia HL-60 cells. The growth of HL-60 cells was inhibited by curcumin, DeMC and DiMC, but not by THC lacking ${\alpha},{\beta}-unsaturated$ carbonyl groups thus suggesting that ${\alpha},{\beta}-unsaturated$ carbonyl groups are crucial for antiproliferative activity. The order of antiproliferative activity was DiMC, curcumin and BDMC indicating that the number of methoxy groups on the aromatic rings of the active compounds plays an important role in enhancing anti-proliferating activity. In comparison with cellular uptake of the active compounds, uptake capacity was found to be highest with DiMC, followed by curcumin and BDMC. Therefore, it is most likely that the differential antiproliferative activities of DiMC, curcumin and BDMC are associated with their capacities of cellular uptake resulting in building up of enough concentration inside the cells.
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