• Title/Summary/Keyword: Bioactivation

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Mechanistic Investigation in the Oxidation of ${\underline{O}},{\underline{O}}-Diethyl-{\underline{S}}-Phenyl\;Phosphorothiolate-^{18}O$ (O,O-Diethyl-S-Phenyl $Phosphorothiolate-^{18}O$의 산화반응기작)

  • Kim, Jeong-Han
    • Applied Biological Chemistry
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    • v.37 no.3
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    • pp.210-215
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    • 1994
  • ${\underline{O}},{\underline{O}}-Diethyl-{\underline{S}}-phenyl\;phosphorothiolate-^{18}O$ and other related compounds were prepared and oxidized with m-chloroperbenzoic acid (MCPBA). Each reaction was followed by $^{31}P$ NMR and the products were analyzed by GC-MS. ${\underline{O}},{\underline{O}}-Diethyl-{\underline{S}}-phenyl\;phosphorothiolate-^{18}O$ was converted to diethyl methyl phosphate in methanol by MCPBA and it was confirmed to contain $^{18}O$, which proved that the originally proposed mechanism of Segall and Casida operates in the oxidative reaction.

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Modulation of Anticarcinogenic Enzyme and Plasma Testosterone Level in Male Mouse Fed Leek-Supplemented Diet (부추 첨가 식이가 수컷 생쥐의 암예방 효소계 및 혈중 웅성호르몬 농도에 미치는 영향)

  • 김정상;곽연주;전희정;이민자;권태완
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.27 no.5
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    • pp.968-972
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    • 1998
  • Allium tuberosum Rotter(Liliaceae) is a perennial herb of which leaves are used for food. Leek has been reported to have pharmacological effects including alleviations of abdominal pain, diarrhea, hematemesis, snakebite, and asthma. To investigate the effect of dietary leek supplementation on the drug-metaboizing enzymes, quinone reductase(QR) and arylhydrocarbon hydroxylase(AHH) activities in the liver, stomach, small intestine and lung, and on the plasma testosterone and dihydrosterone hormone levels, mice were fed 2% and 5% leek diets for 8 weeks. Quinone reductase, an anticarcinogenic enzyme, was significantly induced in stomach, small intestine, and lung but slightly lowered in hepatic tissue in the experimental groups compared to control group. Arylhydrocarbon hydroxylase activity, involved in bioactivation of procarcinogens, was significantly decreased in liver and lung. Leek feeding led to the reduction in the plasma level of dihydrotestosterone which is associated with the incidence of prostate cancer. These findings support the potential chemopreventive activity of leek supplementation.

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Hepatoprotective Effect of Forest frog's oviduct oil on Acetaminophen-induced Liver Injury in Mice. (Acetaminophen에 의해 손상된 마우스 간세포에서 합마유의 간세포보호 효과)

  • Lee, Jang-Cheon
    • The Korea Journal of Herbology
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    • v.22 no.1
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    • pp.1-6
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    • 2007
  • Objectives : The purpose of this study is that the protective effects of habmayou on acetaminophen (AP)-induced hepatotoxicity were investigated in mice. Methods : Before administering AP mice supplied with only water were left alone for 18 hours. after concentration and dissolution in poly ethylglycol AP 400mg per 1kg of mouse weight, we injected AP titrated density with a physiological saline solution into the abdominal cavity of mouse to induce hepatotoxicity. we researched mortality rate and the shape of liver tissue of mouse. Results : Treatment with habmayou (250 mg/kg, p.o.) 0.5 h after AP administration significantly prevented an increase in plasma alanine aminotransferase and aspartate aminotransferase activities and AP-induced hepatic necrosis, and also reduced AP-induced mortality from 46% to 0%. In addition, oral treatment with habmayou significantly prevented AP-induced depletion of glutathione (GSH) contents. However, habmayou treatment, by itself, did not affect hepatic GSH contents. Conclusion : These results show that the hepatoprotective effects of habmayou against AP overdose may be due to its ability to block the bioactivation of AP by regeneration of hepatonecrotic cells.

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A Study on the Affinity of Some Medicinal Herbs to Two Cytochrome P450 Subfamilies, CYP3A4 and CYP2D6 (한약재의 Cytochrome P450 결합관련 안전성에 관한 연구)

  • Yoo, Da-Young;Woo, Hong-Jung;Kim, Young-Chul
    • The Journal of Internal Korean Medicine
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    • v.34 no.4
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    • pp.375-383
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    • 2013
  • Objectives : This study was performed to investigate the metabolic site of some medicinal herbs in the liver associated with CYP (Cytochrome P450). Methods : Cytochrome P450 is the major enzymes involved in drug metabolism and bioactivation. CYP3A4 and CYP2D6, the major CYP isoforms in humans, catalyse the major proportion of drugs available on the market. Scintillation proximity assay (SPA) is often used in studies to identify compounds that inhibit CYP3A4 and CYP2D6. 28 herbal extracts and radioisotopes were attached competitively to SPA beads, and followed by measuring the remaining radioisotopes in the medium. Erythromycin and dexamethasone, inhibitors of CYP3A4 and CYP2D6, were used as controls respectively. Results : Most of the 28 herbal extracts showed dose-dependent affinity to the CYP3A4 while some of the herbs showed affinity to the CYP2D6. Conclusions : These results suggest that most of the 28 herbal extracts are metabolized safely in the liver, combined with CYP3A4 and CYP2D6.

Taraxacum Mongolicum H. Suppress Hepatoprotective Activity by Increasing Liver Antioxidant Enzyme in Carbon Tetrachloride($CCl_4$)-induced Hepatotoxicity in Rats (흰쥐에서 민들레 추출물이 사염화탄소에 의한 산화적 스트레스의 경감기전)

  • Kim, Sung-Hoon;Choi, Jong-Won
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.24 no.3
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    • pp.439-445
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    • 2010
  • Pretreatment with Taraxacum Mongolicum H(TMH) prior to the administration of on $CCl_4$ significantly prevented the increased serum enzymatic activity of aminotransferase(ALT, AST), gamma-glutamyl transpeptidase(GGT) and bilirubin concentration in dose-dependent manner. In addition, pretreatment with TMH also significantly restored the elevation of hepatic malondialdehyde formation and the depletion of reduced glutathione content in the liver $CCl_4$-intoxicated rats. The restoration of microsomal aniline hydroxylase and aminopyrine N-demethylase activities indicated the improvement in functional status of endoplasmic reticulum. $CCl_4$-induced hepatotoxicity was also essentially prevented, as indicated by a liver histopathologic study. TMH showed antioxidant effects in $FeCl_2$-ascorbate-induced lipid peroxidation in rat liver homogenate and in superoxide radical scavenging activity. Our results suggest that the protective effect of TMH against $CCl_4$-induced hepatotoxicity possibly involve mechanisms related to its ability to block p450-mediated $CCl_4$ bioactivation and free radical scavenging effects.

Water Extract of Ash Tree (Fraxinus rhynchophylla) Leaves Protects against Paracetamol-Induced Oxidative Damages in Mice

  • Jeon, Jeong-Ryae
    • Food Science and Biotechnology
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    • v.15 no.4
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    • pp.612-616
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    • 2006
  • The protective effect of water extract of ash tree leaves (ALE) against oxidative damages was investigated in paracetamol-induced BALB/c mice. Biochemical analysis of anti-oxidative enzymes, immunoblot analyses of hepatic cytochrome P450 2El (CYP2E1), and the gene expression of tumor necrosis factor (TNF-${\alpha}$) were examined to determine the extract's protective effect and its possible mechanisms. BALB/c mice were divided into three groups: normal, paracetamol-administered, and ALE-pretreated groups. A single dose of paracetamol led to a marked increase in lipid peroxidation as measured by malondialdehyde (MDA). This was associated with a significant reduction in the hepatic antioxidant system, e.g., glutathione (GSH). Paracetamol administration also significantly elevated the expression of CYP2E1, according to immunoblot analysis, and of TNF-${\alpha}$ mRNA in liver. However, ALE pretreatment prior to the administration of paracetamol significantly decreased hepatic MDA levels. ALE restored hepatic glutathione and catalase levels and suppressed the expression of CYP2E1 and TNF-${\alpha}$ observed in inflammatory tissues. Moreover, ALE restored mitochondrial ATP content depleted by the drug administration. These results show that the extract of ash tree leaves protects against paracetamol-induced oxidative damages by blocking oxidative stress and CYP2E1-mediated paracetamol bioactivation.

Associations of CYP1A1, GSTM1 and GSTT1 Polymorphisms with Lung Cancer Susceptibility in a Northern Indian Population

  • Shukla, R.K.;Tilak, A.R.;Kumar, C.;Kant, S.;Kumar, A.;Mittal, B.;Bhattacharya, S.
    • Asian Pacific Journal of Cancer Prevention
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    • v.14 no.5
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    • pp.3345-3349
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    • 2013
  • Background: Susceptibility to lung cancer has been shown to be modulated by inheritance of polymorphic genes encoding cytochrome P450 1A1 (CYP1A1) and glutathione S transferases (GSTM1 and GSTT1), which are involved in the bioactivation and detoxification of environmental toxins. This might be a factor in the variation in lung cancer incidence with ethnicity. Materials and Methods: We conducted a case-control study of 218 northern Indian lung cancer patients along with 238 healthy controls, to assess any association between CYP1A1, GSTM1 and GSTT1 polymorphisms, either separately or in combination, with the likelihood of development of Lung cancer in our population. Results: We observed a significant difference in the GSTT1 null deletion frequency in this population when compared with other populations (OR=1.87, 95%CI: 1.25-2.80-0.73, P=0.002). However, GSTM1 null genotype was found associated with lung cancer in the non-smoking subgroup. (P=0.170). Conclusions: Our study showed the GSTT1 null polymorphism to be associated with smoking-induced lung cancer and the GSTM1 null polymorphism to have a link with non-smoking related lung cancer.

Inhibition of Carcinogen-Activating Cytochrome P450 Enzymes by Xenobiotic Chemicals in Relation to Antimutagenicity and Anticarcinogenicity

  • Shimada, Tsutomu
    • Toxicological Research
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    • v.33 no.2
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    • pp.79-96
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    • 2017
  • A variety of xenobiotic chemicals, such as polycyclic aromatic hydrocarbons (PAHs), aryl- and heterocyclic amines and tobacco related nitrosamines, are ubiquitous environmental carcinogens and are required to be activated to chemically reactive metabolites by xenobiotic-metabolizing enzymes, including cytochrome P450 (P450 or CYP), in order to initiate cell transformation. Of various human P450 enzymes determined to date, CYP1A1, 1A2, 1B1, 2A13, 2A6, 2E1, and 3A4 are reported to play critical roles in the bioactivation of these carcinogenic chemicals. In vivo studies have shown that disruption of Cyp1b1 and Cyp2a5 genes in mice resulted in suppression of tumor formation caused by 7,12-dimethylbenz[a]anthracene and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, respectively. In addition, specific inhibitors for CYP1 and 2A enzymes are able to suppress tumor formation caused by several carcinogens in experimental animals in vivo, when these inhibitors are applied before or just after the administration of carcinogens. In this review, we describe recent progress, including our own studies done during past decade, on the nature of inhibitors of human CYP1 and CYP2A enzymes that have been shown to activate carcinogenic PAHs and tobacco-related nitrosamines, respectively, in humans. The inhibitors considered here include a variety of carcinogenic and/or non-carcinogenic PAHs and acethylenic PAHs, many flavonoid derivatives, derivatives of naphthalene, phenanthrene, biphenyl, and pyrene and chemopreventive organoselenium compounds, such as benzyl selenocyanate and benzyl selenocyanate; o-XSC, 1,2-, 1,3-, and 1,4-phenylenebis(methylene)selenocyanate.

Effect of Soybean Supplementation on Murine Drug-metabolizing Enzymes and Benzo(a)pyrene-induced Lung Cancer Develpoment (콩보충식이가 생쥐의 해독효소계 및 Benzo(a)pyrene에 의해서 유도된 폐암발생에 미치는 영향)

  • Kwon, Chong-Suk;Kim, Jong-Sang
    • Korean Journal of Food Science and Technology
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    • v.31 no.2
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    • pp.535-539
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    • 1999
  • Soybean has drawn much attention mainly due to its chemopreventive action as well as antiestrogenic effect. Although suppression of breast and prostate cancers were believed to be exerted via antiestrogenic or antiandrogenic activity of genistein, its mechanism of prevention against other cancers has not been clearly demonstrated. We proposed that prevention by soybean from other cancers than sex hormone -related cancers was achieved via modulation of drug-metabolizing enzymes. Addition of acid hydrolysate of 80% methanol extract of soyflour to diet caused a significant induction of quinone reductase, an anticarcinogenic marker enzyme and one of drug-metabolizing enzymes, in mouse lung while it suppressed arylhydrocarbon hydroxylase, involved in bioactivation of procarcinogens, in kidney and small intestine. It is likely that active components exist in a conjugated form and released by acid hydrolysis to be able to affect drug-metabolizing enzyme and exert chemopreventive activity. Benzo(a)pyrene-induced tumor development in mouse lung was greatly reduced by soybean extract supplementation, which is consistent with the extract's capability to modulate favorably arylhydrocarbon hydroxylase and quinone reductase towards chemoprevention.

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Differential Metabolism of the Pyrrolizidine Alkaloid, Senecionine, in Fischer 344 and Sprague-Dawley Rats

  • Chung, Woon-Gye;Donald R. Buhler
    • Archives of Pharmacal Research
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    • v.27 no.5
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    • pp.547-553
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    • 2004
  • The pyrrolizidine alkaloids (PAs), contained in a number of traditional remedies in Africa and Asia, show wide variations in metabolism between animal species but little work has been done to investigate differences between animal strains. The metabolism of the PA senecionine (SN) in Fischer 344 (F344) rats has been studied in order to compare to that found in the previously investigated Sprague-Dawley (SO) rats (Drug Metab. Dispos. 17: 387, 1989). There was no difference in the formation of ($\pm$) 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine (DHP, bioactivation) by hepatic microsomes from either sex of SO and F344 rats. However, hepatic microsomes from male and female F344 rats had greater activity in the Noxidation (detoxication) of SN by 88% and 180%, respectively, when compared to that of male and female SD rats. Experiments conducted at various pH showed an optimum pH of 8.5, the optimal pH for flavin-containing monooxygenase (FMO), for SN N-oxidation by hepatic microsomes from F344 females. In F344 males, however, a bimodal pattern was obtained with activity peaks at pH 7.6 and 8.5 reflecting the possible involvement of both cytochrome P450 (CYP) and FMO. Use of specific inhibitors (SKF525A, 1-benzylimidazole and methimazole) showed that the N-oxide of SN was primarily produced by FMO in both sexes of F344 rats. In contrast, SN N-oxide formation is known to be catalyzed mainly by CYP2C11 rather than FMO in SD rats. This study, therefore, demonstrated that there were substantial differences in the formation of SN N-oxide by hepatic microsomes from F344 and SD rats and that this detoxification is catalyzed primarily by two different enzymes in the two rat strains. These findings suggest that significant variations in PA biotransformation can exist between different animal strains.