메뉴 건너뛰기




Volumn 47, Issue 1, 2015, Pages 12-20

A decades-long investigation of acute metabolism-based hepatotoxicity by herbal constituents: A case study of pennyroyal oil

Author keywords

Bioactivation; in vivo models; Mechanistic studies; Metabolites; P450; Reactive metabolites

Indexed keywords

CYTOCHROME P450; GLUCURONIDE; MENTHOFURAN; PENNYROYAL OIL; PULEGONE; UNCLASSIFIED DRUG; VEGETABLE OIL; CYCLOHEXANONE DERIVATIVE; ESSENTIAL OIL; PLANT MEDICINAL PRODUCT;

EID: 84929457538     PISSN: 03602532     EISSN: 10979883     Source Type: Journal    
DOI: 10.3109/03602532.2014.990032     Document Type: Review
Times cited : (32)

References (31)
  • 1
    • 0029887823 scopus 로고    scopus 로고
    • Pennyroyal toxicity: Measurement of toxic metabolite levels in two cases and review of the literature
    • Anderson IB, Mullen WH, Meeker JE, et al. (1996). Pennyroyal toxicity: Measurement of toxic metabolite levels in two cases and review of the literature. Ann Intern Med 124:726-734.
    • (1996) Ann Intern Med , vol.124 , pp. 726-734
    • Anderson, I.B.1    Mullen, W.H.2    Meeker, J.E.3
  • 2
    • 0029859836 scopus 로고    scopus 로고
    • Multiple organ failure after ingestion of pennyroyal oil from herbal tea in two infants
    • Bakerink JA, Gospe Jr SM, Dimand RJ, Eldridge MW. (1996). Multiple organ failure after ingestion of pennyroyal oil from herbal tea in two infants. Pediatrics 98:944-947.
    • (1996) Pediatrics , vol.98 , pp. 944-947
    • Bakerink, J.A.1    Gospe, S.M.2    Dimand, R.J.3    Eldridge, M.W.4
  • 3
    • 84870576402 scopus 로고    scopus 로고
    • Review article: Herbal and dietary supplement hepatotoxicity
    • Bunchorntavakul C, Reddy KR. (2013). Review article: Herbal and dietary supplement hepatotoxicity. Aliment Pharmacol Ther 37:3-17.
    • (2013) Aliment Pharmacol Ther , vol.37 , pp. 3-17
    • Bunchorntavakul, C.1    Reddy, K.R.2
  • 5
    • 0038650990 scopus 로고    scopus 로고
    • Comparative disposition of (R)-(+)-pulegone in B6C3F1 mice and F344 rats
    • Chen LJ, Lebetkin EH, Burka LT. (2003a ). Comparative disposition of (R)-(+)-pulegone in B6C3F1 mice and F344 rats. Drug Metab Dispos 31:892-899.
    • (2003) Drug Metab Dispos , vol.31 , pp. 892-899
    • Chen, L.J.1    Lebetkin, E.H.2    Burka, L.T.3
  • 6
    • 0141569644 scopus 로고    scopus 로고
    • Metabolism of (R)-(+)-menthofuran in Fischer-344 rats: Identification of sulfonic acid metabolites
    • Chen LJ Lebetkin EH Burka LT.(2003b ). Metabolism of (R)-(+)-menthofuran in Fischer-344 rats: Identification of sulfonic acid metabolites. Drug Metab Dispos 31 1208-1213.
    • (2003) Drug Metab Dispos , vol.31 , pp. 1208-1213
    • Chen, L.J.1    Lebetkin, E.H.2    Burka, L.T.3
  • 7
    • 0035806988 scopus 로고    scopus 로고
    • Perceptions about complementary therapies relative to conventional therapies among adults who use both: Results from a national survey
    • Chen LJ, Lebetkin EH, Burka LT. (2003b ). Metabolism of (R)-(+)-menthofuran in Fischer-344 rats: Identification of sulfonic acid metabolites. Drug Metab Dispos 31:1208-1213.
    • (2001) Ann Intern Med , vol.135 , pp. 344-351
    • Eisenberg, D.M.1    Kessler, R.C.2    Van Rompay, M.I.3
  • 8
    • 0035806988 scopus 로고    scopus 로고
    • Perceptions about complementary therapies relative to conventional therapies among adults who use both: Results from a national survey
    • Eisenberg DM, Kessler RC, Van Rompay MI, et al. (2001). Perceptions about complementary therapies relative to conventional therapies among adults who use both: Results from a national survey. Ann Intern Med 135:344-351.
    • (2001) Ann Intern Med , vol.135 , pp. 344-351
    • Eisenberg, D.M.1    Kessler, R.C.2    Van Rompay, M.I.3
  • 9
    • 0019316329 scopus 로고
    • Herbal abortifacients
    • Gold J, Cates Jr W. (1980). Herbal abortifacients. JAMA 243: 1365-1366.
    • (1980) JAMA , vol.243 , pp. 1365-1366
    • Gold, J.1    Cates, W.2
  • 10
    • 0020428204 scopus 로고
    • Hepatotoxicity and pulmonary toxicity of pennyroyal oil and its constituent terpenes in the mouse
    • Gordon WP, Forte AJ, McMurtry RJ, et al. (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
  • 11
    • 0023506150 scopus 로고
    • The metabolism of the abortifacient terpene, (R)-(+)-pulegone, to a proximate toxin, menthofuran
    • Gordon WP, Huitric AC, Seth CL, et al. (1987). The metabolism of the abortifacient 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
  • 12
    • 0018800944 scopus 로고
    • Plant known for centuries still causes problems today
    • Gunby P. (1979). Plant known for centuries still causes problems today. JAMA 241:2246-2247.
    • (1979) JAMA , vol.241 , pp. 2246-2247
    • Gunby, P.1
  • 13
    • 84869390142 scopus 로고    scopus 로고
    • Characterization of rat liver proteins adducted by reactive metabolites of menthofuran
    • Khojasteh SC, Hartl ey DP, Ford KA, et al. (2012). Characterization of rat liver proteins adducted by reactive metabolites of menthofuran. Chem Res Toxicol 25:2301-2309.
    • (2012) Chem Res Toxicol , vol.25 , pp. 2301-2309
    • Khojasteh, S.C.1    Hartley, D.P.2    Ford, K.A.3
  • 14
    • 78649251903 scopus 로고    scopus 로고
    • Metabolism and toxicity of menthofuran in rat liver slices and in rats
    • Khojasteh SC, Oishi S, Nelson SD. (2010). Metabolism and toxicity of menthofuran in rat liver slices and in rats. Chem Res Toxicol 23: 1824 -1832.
    • (2010) Chem Res Toxicol , vol.23 , pp. 1824-1832
    • Khojasteh, S.C.1    Oishi, S.2    Nelson, S.D.3
  • 15
    • 0032960136 scopus 로고    scopus 로고
    • Metabolism of (R)-(+)-pulegone and (R)-(+)-menthofuran by human liver cytochrome P-450s: Evidence for formation of a furan epoxide
    • Khojasteh-Bakht SC, Chen W, Koenigs LL, et al. (1999a ). Metabolism of (R)-(+)-pulegone and (R)-(+)-menthofuran by human liver cytochrome P-450s: Evidence for formation of a furan epoxide. Drug Metab Dispos 27:574-580.
    • (1999) Drug Metab Dispos , vol.27 , pp. 574-580
    • Khojasteh-Bakht, S.C.1    Chen, W.2    Koenigs, L.L.3
  • 16
    • 0031848620 scopus 로고    scopus 로고
    • (R)-(+)-menthofuran is a potent, mecha nism-based inactivator of human liver cytochrome P450 2A6
    • Khojasteh-Bakht SC, Koenigs LL, Peter RM, et al. (1998). (R)-(+)-menthofuran is a potent, mecha nism-based inactivator of human liver cytochrome P450 2A6. Drug Metab Dispos 26:701-704.
    • (1998) Drug Metab Dispos , vol.26 , pp. 701-704
    • Khojasteh-Bakht, S.C.1    Koenigs, L.L.2    Peter, R.M.3
  • 17
    • 0033215126 scopus 로고    scopus 로고
    • Glutathione Stransferase catalyzes the isomerization of (R)-2-hydroxymenthofuran to mintlactones
    • Khojasteh-Bakht SC, Nelson SD, Atkins WM. (1999b ). Glutathione Stransferase catalyzes the isomerization of (R)-2-hydroxymenthofuran to mintlactones. Arch Biochem Biophys 370:59-65.
    • (1999) Arch Biochem Biophys , vol.370 , pp. 59-65
    • Khojasteh-Bakht, S.C.1    Nelson, S.D.2    Atkins, W.M.3
  • 18
    • 0032970002 scopus 로고    scopus 로고
    • Metabolic disposition of a monoterpene ketone, piperitenone, in rats: Evidence for the formation of a known toxi n, p-cresol
    • Madyastha KM, Gaikwad NW. (1999). Metabolic disposition of a monoterpene ketone, piperitenone, in rats: Evidence for the formation of a known toxi n, 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
  • 19
    • 0027247503 scopus 로고
    • Studies on the metabolism of a monoterpene ketone, R-(+)-pulegone-A hepatotoxin in rat: Isolation and characterization of new metabolites
    • Madyastha KM, Raj CP. (1993). Studies on the metabolism of a monoterpene ketone, R-(+)-pulegone-A hepatotoxin in rat: Isolation and characterization of new metabolites. Xenobiotica 23: 509-518.
    • (1993) Xenobiotica , vol.23 , pp. 509-518
    • Madyastha, K.M.1    Raj, C.P.2
  • 20
    • 0036398961 scopus 로고    scopus 로고
    • Stereoselective hydroxylation of 4-methyl-2-cyclohexenone in rats: Its relevance to R-(+)-pulegonemediated hepatotoxicity
    • Madyastha KM, Raj CP. (2002). Stereoselective hydroxylation of 4-methyl-2-cyclohexenone in rats: Its relevance to R-(+)-pulegonemediated hepatotoxicity. Biochem Biophys Res Commun 297: 202-205.
    • (2002) Biochem Biophys Res Commun , vol.297 , pp. 202-205
    • Madyastha, K.M.1    Raj, C.P.2
  • 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, 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
  • 23
    • 0024555267 scopus 로고
    • Hepatotoxicity of pulegone in rats: Its effects on microsomal enzymes, in vivo
    • Moorthy B, M adyastha P, Madyastha KM. (1989a ). 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
    • 0024595657 scopus 로고
    • Metabolism of a monoterpene ketone, R-(+)-pulegone-A hepatotoxin in rat
    • Moorthy B, Madyastha P, Madyastha KM. (1989b ). Metabolism of a 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
  • 25
    • 0026672930 scopus 로고
    • Investigations of mechanisms of reactive metabolite formation from (R)-(+)-pulegone
    • Nelson SD, McClanahan RH, Thomassen D, et al. (1992). Investigations of mechanisms of reactive metabolite formation from (R)-(+)-pulegone. Xenobiotica 22:1157-1164.
    • (1992) Xenobiotica , vol.22 , pp. 1157-1164
    • Nelson, S.D.1    McClanahan, R.H.2    Thomassen, D.3
  • 26
    • 0036257022 scopus 로고    scopus 로고
    • Herbal hepatotoxicity
    • Stedman C. (2002). Herbal hepatotoxicity. Semin Liver Dis 22:195-206.
    • (2002) Semin Liver Dis , vol.22 , pp. 195-206
    • Stedman, C.1
  • 27
    • 84943673897 scopus 로고
    • Pennyroyal oil poisoning and hepatotoxicity
    • Sullivan Jr JB, Rumack BH, Thomas Jr H, et al. (1979). Pennyroyal oil poisoning and hepatotoxicity. JAMA 242:2873-2874.
    • (1979) JAMA , vol.242 , pp. 2873-2874
    • Sullivan, J.B.1    Rumack, B.H.2    Thomas, H.3
  • 28
    • 0141445989 scopus 로고    scopus 로고
    • Mitigation of pennyroyal oil hepatotoxicity in the mouse
    • Sztajnkrycer MD, Otten EJ, Bond GR, et al. (2003). Mitigation of pennyroyal oil hepatotoxicity in the mouse. Acad Emerg Med 10: 1024-1028.
    • (2003) Acad Emerg Med , vol.10 , pp. 1024-1028
    • Sztajnkrycer, M.D.1    Otten, E.J.2    Bond, G.R.3
  • 29
    • 0026077167 scopus 로고
    • Partial characterization of biliary metabolites of pulegone by tandem mass spectrometry. Detection of glucuronide, glut athione, and glutathionyl glucuronide conjugates
    • Thomassen D, Pearson PG, Slattery JT, Nelson SD.(1991). Partial characterization of biliary metabolites of pulegone by tandem mass spectrometry. Detection of glucuronide, glut athione, and glutathionyl glucuronide conjugates. Drug Metab Dispos 19 997-1003.
    • (1991) Drug Metab Dispos , vol.19 , pp. 997-1003
    • Thomassen, D.1    Pearson, P.G.2    Slattery, J.T.3    Nelson, S.D.4
  • 30
    • 0023836650 scopus 로고
    • Contribution of menthofuran to the hepatotoxicity of pulegone: Assessment based on m atched area under the curve and on matched time course
    • Thomassen D, Slattery JT, Nelson SD. (1988). Contribution of menthofuran to the hepatotoxicity of pulegone: Assessment based on m atched 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
  • 31
    • 0007722217 scopus 로고
    • Pennyroyal poisoning: A fatal case
    • Vallance WB. (1955). Pennyroyal poisoning: A fatal case. Lancet 269: 850-851.
    • (1955) Lancet , vol.269 , pp. 850-851
    • Vallance, W.B.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.