• Title/Summary/Keyword: endoperoxide

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A New Endoperoxide from Artemisia selengensis (물쑥의 Peroxide 성분)

  • Jang, Woo-Young;Lee, Kang-Ro
    • Korean Journal of Pharmacognosy
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    • v.24 no.2
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    • pp.107-110
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    • 1993
  • From the ethanol extract of the leaves of Artemisia selengensis a new sesquiterpene endoperoxide, bisabolene-2,5-endoperoxide, has been isolated. The structure of the peroxide was established on the basis of spectroscopic evidence.

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Peroxide Constituents in the Natural Product Research (천연물 연구에서의 Peroxide 성분)

  • Lee, Kang-Ro
    • Korean Journal of Pharmacognosy
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    • v.22 no.3
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    • pp.145-155
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    • 1991
  • Peroxides in natural products have been recently received a considerable attention due to their various biological and pharmacological properties. Nearly 300 peroxides have been isolated and structually characterized from natural sources, mainly as constituents of Compositae and marine sponge, and occur randomly in about 10 other plant families. Among peroxides studied, sesquiterpene endoperoxide, quinghaosu, has been already clinically applied as a new antimalarial drug. Based on the peroxides reported, structural classification, natural distribution and biological and pharmacological activities are reviewed. Color reagent and spectroscopic identification of peroxide are also described.

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1, 5 - bis (4 - methoxyphenyls) - 6, 7 - Dioxa-bicyclo [3.2.2] nonane's Anti-toxoplasmosis Effect that was Separated in Artemisin annula (개똥쑥에서 분리 확인된 endoperoxide ring 구조를 갖는 1,5-bis(4-methoxyphenyl)-6,7-dioxa-bicyclo[3.2.2]nonane의 항톡소포자충 효과)

  • Jiang, Jing-Hua;Kim, Hwa-Kyoung;Kim, Hye-Sook;Kamata, Masaki;Wataya, Yusuke;Park, Hyun
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.21 no.1
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    • pp.82-85
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    • 2007
  • The Chinese medicinal plant Artemisia annua is the source of the antimalarial compound artemisinin. By the way, Artemisin annula was known have endoperoxide ring structure is included and has anti-malarial effect. Malaria and Toxoplasma gondii (T. gondii) is belong to Apicomplexa genera. So, confirmed whether we go compound 1,5-bis(4-methoxyphenyl)-6,7-dioxa-bicyclo[3.2.2]nonane that have endoperoxide ring structure and there is anti-toxoplasmosis effect. The efficacy of 1,5-bis(4-methoxyphenyl)-6,7-dioxa-bicyclo[3.2.2] nonane alone was examined in vitro and in a murine model of acute toxoplasmosis. In vitro studies were peformed with HeLa cell cultures, with quantification of Toxoplasma growth by a cell proliferation assay. Selectivity of 1,5-bis(4-methoxyphenyl)-6,7-dioxa-bicyclo[3.2.2]nonane was 4.9 in vitro cell proliferation assay, this is higher than sulfadiazine (selectivity was 1.63). For in vivo studies, mice were acutely infected intraperitoneally with 10$^5$ tachyzoites of the virulent RH strain and then treated perorally for 4 days from 6 hours postinfection. Efficacy was assessed by sequential determination of parasite burdens in peritoneal cavity. in vitro, 1,5-bis(4-methoxyphenyl)-6,7-dioxa-bicyclo[3.2.2]nonane inhibited Toxoplasma growth at a concentration of 150mg/kg of body weight per day, the inhibition ratio was estimated to be 85.72%.

Effects of Oxygen on the Photochemical Behaviors of Methacrylic Homopolymer Containing Anthracene Groups

  • Kim, Yong-Woon;Chae, Kyu-Ho
    • Journal of Photoscience
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    • v.9 no.3
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    • pp.57-63
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    • 2002
  • A homopolymer containing anthracene groups, poly[6-(9-anthryloxy)hexyl methacrylate] (PAn) was prepared and the effect of oxygen on its photochemical reaction was studied by UV and IR absorption spectroscopy in order to understand its photochemical behavior. Photochemical reaction of the PAn in THF solution under an atmosphere of air resulted in the formation of endoperoxide at the beginning stage of reaction followed by photodimerization reaction after all the oxygen was consumed, whereas photodimerization and endoperoxide formation took place concomitantly in the film state. The photoreversible reaction of the anthracene photodimer groups in the polymer by photolysis with 254 nm UV light was not efficient. The IR absorption spectral changes of the PAn film upon irradiation indicate that various photooxidation products were produced in the atmosphere of air.

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Preferential Peroxidase Activity of Prostaglandin Endoperoxide H Synthase for Lipid Peroxides

  • Yun, Seol-Ryung;Han, Su-Kyong;Song, In-Seok
    • Proceedings of the Korean Society of Applied Pharmacology
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    • 2001.11a
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    • pp.94-94
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    • 2001
  • Prostaglandin endoperoxide H synthase (PGHS) catalyzes the committed step in prostaglandins and thromboxane A$_2$-- oxygenation of arachidonic acid to the hydroperoxy endoperoxide PGG$_2$, followed by reduction PGG$_2$to the alcohol PGH$_2$. The two reactions by PGHS -- cyclooxygenase and peroxidase -- occur at distinct but structurally and functionally interconnected sites. The peroxidase reaction occurs at a heme-containing active site located near the protein surface. The cyclooxygenase reaction occurs in a hydrophobic channel in the core of the enzyme. Initially a peroxide reacts with the heme group, yielding Compound I and an alcohol derived from the oxidizing peroxide. Compound I next undergoes an intramolecular reduction by a single electron traveling from Tyr385 along the peptide chain to the proximal heme ligand, His388, and finally to the heme group. Following the binding of arachidonic acid, Tyr385 tyrosyl radical initiates the cyclooxygenase reaction by abstracting the 13-pro(5) hydrogen atom to give an arachidonyl radical, which sequentially reacts with two molecules of oxygen to yield PGG$_2$. In order to characterize PGHS peroxidase active site, we examined various lipid peroxides with purified recombinant ovine PGHS proteins and determined the rate constants. The results have shown that twenty-carbon unsaturated fatty acid hydroperoxides have similar efficiency in peroxidation by PGHS, irrespective of either the location of hydroperoxy group or the number of double bonds. It was also confirmed by the subsequent study with PGHS peroxidase active site mutants.

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Association of Polymorphisms in Epidermal Growth Factor, Prostaglandin-endoperoxide Synthase 2 and Prolactin Receptor Genes with Semen Quality in Duroc Boars

  • Huang, S.Y.;Song, H.L.;Lin, E.-C.;Lee, W.C.;Chiang, J.C.;Tsou, H.L.
    • Asian-Australasian Journal of Animal Sciences
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    • v.19 no.6
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    • pp.793-798
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    • 2006
  • The quality characteristics of semen are important indicators of the fertility of a boar. Development of genetic markers for the semen quality in boars will be beneficial to the improvement of porcine fertility. We investigated the relationship between the polymorphisms of epidermal growth factor (EGF), prostaglandin-endoperoxide synthase 2 (PTGS2) and prolactin receptor (PRLR) genes, and semen quality traits in boars. The genomic DNA of 233 boars (157 Duroc and 86 Landrace) from a central testing station was subjected to genotyping for surveying gene frequency. The EGF, PTGS2 and PRLR genotypes were determined using the restriction fragment length polymorphism method. Thirty-seven normal, mature Duroc boars from an AI center were also genotyped and their semen quality traits were collected. The effect of genotype on semen quality traits was analyzed by the least-squares means method using data corrected for season. The frequencies of the AA genotype of EGF, PTGS2 and PRLR in Duroc boars were 0.14, 0.01 and 0.66, respectively. In Landrace, the frequencies of the AA genotype were 0.03, 0.09 and 0.62, respectively. Boars with the BB genotype in EGF, with the AB genotype in PTGS2 and with the AA genotype in PRLR had significantly better semen quality with a higher percentage of normal sperm and a lower percentage of immature sperm than those with other genotypes. These findings imply that polymorphisms of EGF, PTGS2 and PRLR genes might be used as markers for improving the semen quality of boars.

Ginsenosides Inhibit Endothelium - dependent Contraction in the Spontaneously Hypertensive Rat Aorta isn vitro (선천성 고혈압 랫드에서 ginsenosides에 의한 내피의존성수축의 억제작용)

  • 김낙두;최원선
    • Journal of Ginseng Research
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    • v.21 no.2
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    • pp.125-132
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    • 1997
  • Our previous study showed that in vivo treatment of spontaneously hypertensive rats (SHR) with protopanaxatriol ginsenosides (PPT) reduces the blood pressure and inhibits the con- tractions induced by endothelium-derived contracting factor (prostaglandin endoperoxide ($PGH_2$) and superoxide anion) in aorta isolated from SHR. The aim of the present study is to examine whether PPT improves endothelial functions in the isolated thoracic aorta of SHR in vitro. Treatments of aortic rings with PPT, purified ginsenoside $Rg_1$ ($Rg_1$) or indomethacin normalized endotheliuln-dependent relaxation to acetylcholine, but not with protopanaxadiol ginsenosides (PPD) and purified ginsenoside Rb1 (Rb1). The effects of PPT were dose-dependent. PGH,- and oxygen free radical-inducted contractions in rat aorta without endothelium were inhibited by PPT or $Rg_1$, but not by PPD or $Rb_1$. Contractions induced by PGF2$\alpha$, U-46619, a stable thromboxane A2 agonist or KCI (60 mM) were not inhibited by PPT, $Rg_1$ or $Rb_1$. These findings demonstrate that PPT but not PPD scavenges the oxygen-derived free radicals and/or antagonize the effects of $PGH_2$ in the vascular smooth muscle and may explain the hypotensive effect of ginseng in the SHR.

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Anti-tumor effect of new compound, 127, through the induction of apoptosis (새로운 화합물 c-127의 세포고사 유도에 의한 항암효과)

  • Baek, Ki Hwan;Han, A Lum;Shin, Sae Ron;Jin, Chun Mae;Yoon, Young Wook;Yu, Seung Taek;Kim, Jong Duk;Choi, Du Young
    • Clinical and Experimental Pediatrics
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    • v.52 no.6
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    • pp.696-700
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    • 2009
  • Purpose : We screened more than 350 compounds with an endoperoxide ring structure in search of an anti-leukemic drug and found that compound 127 (c-127) could induce significant cytotoxicity in HL-60 cells. In this study, we investigated the molecular mechanisms of compound 127-induced antitumor activity on HL-60 cells. Methods : HL-60 cells were cultured in Rosewell Park Memorial Institute 1640 and cell viability was measured by MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide], a tetrazole assay. Apoptosis was assessed by a DNA fragmentation test. Apoptotic machineries were determined by Western blot analysis. Results : C-127 could induce a cytotoxic effect at 24 h and apoptosis at 6 h, which was demonstrated with MTT assay and DNA fragmentation test, respectively. The apoptotic effect of this drug was caused by the activation of the intracellular caspase-8,3 activation, the cleavage of pro-apoptotic Bid, and the increase of c-Jun expression accompanied with JNK (Jun N-terminal kinases) phosphorylation. On the contrary, it increased the expression of anti-apoptotic Bcl-2 levels, leading to the induction of the induction of anti-apoptotic effect. Taken together, the present study demonstrated that c-127 was a potent inducer of cytotoxicity on HL-60 cells through apoptotic mechanisms, which included the activation of caspase family, the regulation of Bcl-2 family, and the activation of JNK signaling pathway. Conclusion : Our results suggest that c-127 has a strong antitumor activity through the regulation of various apoptotic machineries on HL-60 cells. The compound may be utilized as an effective and potentially therapeutic drug in leukemia.