메뉴 건너뛰기




Volumn 28, Issue 7, 2000, Pages 833-844

Role of C-5 chiral center in R-(+)-pulegone-mediated hepatotoxicity: Metabolic disposition and toxicity of 5,5-dimethyl-2-(1-methylethylidene)- cyclohexanone in rats

Author keywords

[No Author keywords available]

Indexed keywords

3 METHYLCHOLANTHRENE; ALANINE AMINOTRANSFERASE; BENZOFURAN DERIVATIVE; CARBON MONOXIDE; CARBON TETRACHLORIDE; CYCLOHEXANONE DERIVATIVE; CYTOCHROME C OXIDASE; CYTOCHROME P450; DRUG METABOLITE; FURANONE DERIVATIVE; GLUCOSE 6 PHOSPHATASE; METYRAPONE; PHENOBARBITAL; PROADIFEN; PULEGONE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; TERPENE DERIVATIVE;

EID: 0033941437     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (6)

References (37)
  • 2
    • 0141478781 scopus 로고
    • Occurrence of menthofuran in oil of peppermint (Mentha piperita vulgaris S.)
    • Bedoukian PZ (1948) Occurrence of menthofuran in oil of peppermint (Mentha piperita vulgaris S.). J Am Chem Soc 70:621-622.
    • (1948) J Am Chem Soc , vol.70 , pp. 621-622
    • Bedoukian, P.Z.1
  • 3
    • 0019743792 scopus 로고
    • Toxicity mediated by reactive metabolites of furans
    • Snyder R, Parke DV, Kocsis JJ, Jollow DJ, Gibson CG and Werner CM eds, Plenum Press, New York
    • Boyd MR (1982) Toxicity mediated by reactive metabolites of furans, in Biological Reactive Intermediates (Snyder R, Parke DV, Kocsis JJ, Jollow DJ, Gibson CG and Werner CM eds) pp 865-879, Plenum Press, New York.
    • (1982) Biological Reactive Intermediates , pp. 865-879
    • Boyd, M.R.1
  • 4
    • 0018824250 scopus 로고
    • The pulmonary clara cell as a target for toxic chemicals requiring metabolic activation; studies with carbon tetrachloride
    • Boyd MR, Statham CN and Longo NS (1980) The pulmonary clara cell as a target for toxic chemicals requiring metabolic activation; Studies with carbon tetrachloride. J Pharmacol Exp Ther 212:109-114.
    • (1980) J Pharmacol Exp Ther , vol.212 , pp. 109-114
    • Boyd, M.R.1    Statham, C.N.2    Longo, N.S.3
  • 5
    • 0010973989 scopus 로고
    • Phenols, and phenolic compounds
    • Patty FA ed, Interscience Publishers, New York
    • Deichmann WB and Keplinger MI (1958) Phenols, and phenolic compounds, in Industrial Hygiene and Toxicology (Patty FA ed) vol II, pp 1363-1408, Interscience Publishers, New York.
    • (1958) Industrial Hygiene and Toxicology , vol.2 , pp. 1363-1408
    • Deichmann, W.B.1    Keplinger, M.I.2
  • 6
    • 0020428204 scopus 로고
    • Hepatotoxicity and pulmonary toxicity of pennyroyal oil and its constituent terpenes in the mouse
    • Gordon WP, Forte AJ, McMurtry RJ, Gal J and Nelson SD (1982) Hepatotoxicity and pulmonary toxicity of pennyroyal oil and its constituent terpenes in the mouse. Toxicol Appl Pharmacol 65:413-424.
    • (1982) Toxicol Appl Pharmacol , vol.65 , pp. 413-424
    • Gordon, W.P.1    Forte, A.J.2    McMurtry, R.J.3    Gal, J.4    Nelson, S.D.5
  • 7
    • 0023506150 scopus 로고
    • The metabolism of the abortificient terpene, R-(+)-pulegone to a proximate toxin, menthofuran
    • Gordon WP, Huitric AC, Seth CL, McClanahan RH and Nelson SD (1987) The metabolism of the abortificient terpene, R-(+)-pulegone to a proximate toxin, menthofuran. Drug Metab Dispos 15:589-594.
    • (1987) Drug Metab Dispos , vol.15 , pp. 589-594
    • Gordon, W.P.1    Huitric, A.C.2    Seth, C.L.3    McClanahan, R.H.4    Nelson, S.D.5
  • 8
    • 0343123211 scopus 로고
    • The chemistry of carbanions. 29. The nature of the enolate formed by addition of lithium dimethyl cuprate to enones
    • House HO and Wilkins JM (1976) The chemistry of carbanions. 29. The nature of the enolate formed by addition of lithium dimethyl cuprate to enones. J Org Chem 41:4031-4033.
    • (1976) J Org Chem , vol.41 , pp. 4031-4033
    • House, H.O.1    Wilkins, J.M.2
  • 11
    • 0015512089 scopus 로고
    • Partial purification of cytochrome P-450 and P-448 from rat liver microsomes
    • Lu AYH and Levin W (1972) Partial purification of cytochrome P-450 and P-448 from rat liver microsomes. Biochem Biophys Res Commun 46:1334-1339.
    • (1972) Biochem Biophys Res Commun , vol.46 , pp. 1334-1339
    • Lu, A.Y.H.1    Levin, W.2
  • 12
    • 0031657351 scopus 로고    scopus 로고
    • Metabolic fate of S-(-)-pulegone in rat
    • Madyastha KM and Gaikwad NW (1998) Metabolic fate of S-(-)-pulegone in rat. Xenobiotica 28:723-734.
    • (1998) Xenobiotica , vol.28 , pp. 723-734
    • Madyastha, K.M.1    Gaikwad, N.W.2
  • 13
    • 0032970002 scopus 로고    scopus 로고
    • Metabolic disposition of a monoterpene ketone, piperitenone, in rats: Evidence for the formation of known toxin, p-cresol
    • Madyastha KM and Gaikwad NW (1999) Metabolic disposition of a monoterpene ketone, piperitenone, in rats: Evidence for the formation of known toxin, p-cresol. Drug Metab Dispos 27:74-80.
    • (1999) Drug Metab Dispos , vol.27 , pp. 74-80
    • Madyastha, K.M.1    Gaikwad, N.W.2
  • 15
    • 0025565951 scopus 로고
    • Biotransformations of R-(+)-pulegone and menthofuran in vitro. Chemical basis for toxicity
    • Madyastha KM and Raj CP (1990) Biotransformations of R-(+)-pulegone and menthofuran in vitro. Chemical basis for toxicity. Biochem Biophys Res Commun 173:1086-1092.
    • (1990) Biochem Biophys Res Commun , vol.173 , pp. 1086-1092
    • Madyastha, K.M.1    Raj, C.P.2
  • 16
    • 0025879249 scopus 로고
    • Evidence for the formation of a known toxin, p-cresol from menthofuran
    • Madyastha KM and Raj CP (1991) Evidence for the formation of a known toxin, p-cresol from menthofuran. Biochem Biophys Res Commun 177:440-446.
    • (1991) Biochem Biophys Res Commun , vol.177 , pp. 440-446
    • Madyastha, K.M.1    Raj, C.P.2
  • 17
    • 0026509626 scopus 로고
    • Metabolic fate of menthofuran in rats. Novel oxidative pathways
    • Madyastha KM and Raj CP (1992) Metabolic fate of menthofuran in rats. Novel oxidative pathways. Drug Metab Dispos 20:295-301.
    • (1992) Drug Metab Dispos , vol.20 , pp. 295-301
    • Madyastha, K.M.1    Raj, C.P.2
  • 18
    • 0027247503 scopus 로고
    • Studies on the metabolism of a monoterpene ketone R-(+)-pulegone-a hepatotoxin, in rat: Isolation and characterisation of new metabolites
    • Madyastha KM and Raj CP (1993) Studies on the metabolism of a monoterpene ketone R-(+)-pulegone-a hepatotoxin, in rat: Isolation and characterisation of new metabolites. Xenobiotica 23:509-518.
    • (1993) Xenobiotica , vol.23 , pp. 509-518
    • Madyastha, K.M.1    Raj, C.P.2
  • 19
    • 0028319138 scopus 로고
    • Effects of menthofuran, a monoterpene furan on rat liver microsomal enzymes, in vivo
    • Madyastha KM and Raj CP (1994) Effects of menthofuran, a monoterpene furan on rat liver microsomal enzymes, in vivo. Toxicology 89:119-125.
    • (1994) Toxicology , vol.89 , pp. 119-125
    • Madyastha, K.M.1    Raj, C.P.2
  • 20
    • 0342688935 scopus 로고
    • 2 or polyiroinosinic acid. Polyribocytidylic acid to mice
    • Gut I, Cikrt M and Plaa GL eds, Springer-Verlag, New York
    • 2 or polyiroinosinic acid. Polyribocytidylic acid to mice, in Industrial and Environmental Xenobiotics (Gut I, Cikrt M and Plaa GL eds) pp 133-146, Springer-Verlag, New York.
    • (1981) Industrial and Environmental Xenobiotics , pp. 133-146
    • Mannering, G.J.1    Deloria, L.B.2    Abbott, V.S.3
  • 21
    • 0024453882 scopus 로고
    • Metabolic activation of R-(+)-pulegone to a reactive enonal that covalently binds to mouse liver proteins
    • McClanahan RH, Thomassen D, Slattery JT and Nelson SD (1989) Metabolic activation of R-(+)-pulegone to a reactive enonal that covalently binds to mouse liver proteins. Chem Res Toxicol 2:349-355.
    • (1989) Chem Res Toxicol , vol.2 , pp. 349-355
    • McClanahan, R.H.1    Thomassen, D.2    Slattery, J.T.3    Nelson, S.D.4
  • 22
    • 0024595657 scopus 로고
    • Metabolism of monoterpene ketone R-(+)-pulegone-a hepatotoxin in rat
    • Moorthy B, Madyastha P and Madyastha KM (1989a) Metabolism of monoterpene ketone R-(+)-pulegone-a hepatotoxin in rat. Xenobiotica 19:217-224.
    • (1989) Xenobiotica , vol.19 , pp. 217-224
    • Moorthy, B.1    Madyastha, P.2    Madyastha, K.M.3
  • 23
    • 0024555267 scopus 로고
    • Hepatotoxicity of pulegone in rats: Its effects on microsomal enzymes in vivo
    • Moorthy B, Madyastha P and Madyastha KM (1989b) Hepatotoxicity of pulegone in rats: its effects on microsomal enzymes in vivo. Toxicology 55:327-337.
    • (1989) Toxicology , vol.55 , pp. 327-337
    • Moorthy, B.1    Madyastha, P.2    Madyastha, K.M.3
  • 24
    • 0011035073 scopus 로고
    • Biochemical, histopathological and ultra structural changes in rat liver induced by R-(+)-pulegone, a monoterpene ketone
    • Moorthy B, Vijayasarathi SK, Basu A and Madyastha KM (1991) Biochemical, histopathological and ultra structural changes in rat liver induced by R-(+)-pulegone, a monoterpene ketone. Toxicol Environ Chem 33:121-131.
    • (1991) Toxicol Environ Chem , vol.33 , pp. 121-131
    • Moorthy, B.1    Vijayasarathi, S.K.2    Basu, A.3    Madyastha, K.M.4
  • 25
    • 0343123207 scopus 로고
    • An improved process for the synthesis of piperitenone from mesityloxide and methyl vinyl ketone
    • Nakanishi O, Fujitani M, Ichimoto I and Veda H (1980) An improved process for the synthesis of piperitenone from mesityloxide and methyl vinyl ketone. Agric Biol Chem 44:1667-1668.
    • (1980) Agric Biol Chem , vol.44 , pp. 1667-1668
    • Nakanishi, O.1    Fujitani, M.2    Ichimoto, I.3    Veda, H.4
  • 27
    • 78651165715 scopus 로고
    • The carbon monoxide binding pigment of liver microsomes. I. Evidence for its hemoprotein nature
    • Omura T and Sato R (1964) The carbon monoxide binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J Biol Chem 239:2370-2378.
    • (1964) J Biol Chem , vol.239 , pp. 2370-2378
    • Omura, T.1    Sato, R.2
  • 28
    • 0343123208 scopus 로고
    • The chemistry of the eremophilane and related sesquiterpenes
    • Pinder AR (1977) The chemistry of the eremophilane and related sesquiterpenes. Prog Chem Org Nat Prod 34:81-186.
    • (1977) Prog Chem Org Nat Prod , vol.34 , pp. 81-186
    • Pinder, A.R.1
  • 29
    • 0343995315 scopus 로고
    • Potentiation of haloalkane-induced hepatotoxicity and nephrototoxicity: Role of biotransformation
    • Gut I, Cikrt M and Plaa GL eds, Springer-Verlag, New York
    • Plaa GL (1981) Potentiation of haloalkane-induced hepatotoxicity and nephrototoxicity: Role of biotransformation, in Industrial and Environmental Xenobiotics (Gut I, Cikrt M and Plaa GL eds) pp 96-110, Springer-Verlag, New York.
    • (1981) Industrial and Environmental Xenobiotics , pp. 96-110
    • Plaa, G.L.1
  • 30
    • 66349129125 scopus 로고
    • A colorimetric method for the determination of serum oxaloacetic and glutamic pyruvic transaminases
    • Reitman S and Frankel S (1957) A colorimetric method for the determination of serum oxaloacetic and glutamic pyruvic transaminases. Am J Clin Pathol 28:56-63.
    • (1957) Am J Clin Pathol , vol.28 , pp. 56-63
    • Reitman, S.1    Frankel, S.2
  • 32
    • 0023836650 scopus 로고
    • Contribution of menthofuran to the hepatotoxicity of pulegone, assessment based on matched area under the curve, and on matched time course
    • Thomassen D, Slattery JT and Nelson SD (1988) Contribution of menthofuran to the hepatotoxicity of pulegone, assessment based on matched area under the curve, and on matched time course. J Pharmacol Exp Ther 244:825-829.
    • (1988) J Pharmacol Exp Ther , vol.244 , pp. 825-829
    • Thomassen, D.1    Slattery, J.T.2    Nelson, S.D.3
  • 33
    • 0025292086 scopus 로고
    • Menthofuran dependent and independent aspects of pulegone hepatotoxicity: Role of glutathione
    • Thomassen D, Slattery JT and Nelson SD (1990) Menthofuran dependent and independent aspects of pulegone hepatotoxicity: Role of glutathione. J Pharmacol Exp Ther 253:567-572.
    • (1990) J Pharmacol Exp Ther , vol.253 , pp. 567-572
    • Thomassen, D.1    Slattery, J.T.2    Nelson, S.D.3
  • 35
    • 0021018027 scopus 로고
    • Short-term toxicity study in rats dosed with pulegone and menthol
    • Thorup I, Wurtzen G, Carstenson J and Olsen P (1983) Short-term toxicity study in rats dosed with pulegone and menthol. Toxicol Lett 19:207-210.
    • (1983) Toxicol Lett , vol.19 , pp. 207-210
    • Thorup, I.1    Wurtzen, G.2    Carstenson, J.3    Olsen, P.4
  • 36
    • 0015127009 scopus 로고
    • Differences in the potentiation of carbon tetrachloride in rats by ethanol and isopropanol pretreatment
    • Traiger GJ and Plaa GL (1971) Differences in the potentiation of carbon tetrachloride in rats by ethanol and isopropanol pretreatment. Toxicol Appl Pharmacol 20:105-112.
    • (1971) Toxicol Appl Pharmacol , vol.20 , pp. 105-112
    • Traiger, G.J.1    Plaa, G.L.2
  • 37
    • 0017794681 scopus 로고
    • Assay of formaldehyde generated during microsomal oxidation reactions
    • Fleicher S and Packer L eds, Academic Press, New York
    • Werringloer J (1978) Assay of formaldehyde generated during microsomal oxidation reactions, in Methods in Enzymology, Biomembranes, Part C (Fleicher S and Packer L eds) vol 52, pp 297-302, Academic Press, New York.
    • (1978) Methods in Enzymology, Biomembranes, Part C , vol.52 , pp. 297-302
    • Werringloer, J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.