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Volumn 13, Issue 5, 2000, Pages 363-372

Electrophilic properties of patulin. Adduct structures and reaction pathways with 4-bromothiophenol and other model nucleophiles

Author keywords

[No Author keywords available]

Indexed keywords

PATULIN; THIOPHENOL DERIVATIVE;

EID: 0034039154     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9901478     Document Type: Article
Times cited : (50)

References (31)
  • 1
    • 0002013764 scopus 로고
    • Patulin
    • (Sharma, R. P., and Salunkhe, D. K., Eds.) CRC Press, Boca Raton, FL
    • McKinley, E. R., and Carlton, W. W. (1991) Patulin. In Mycotoxins and phytoalexins (Sharma, R. P., and Salunkhe, D. K., Eds.) pp 191-236, CRC Press, Boca Raton, FL.
    • (1991) Mycotoxins and Phytoalexins , pp. 191-236
    • McKinley, E.R.1    Carlton, W.W.2
  • 2
    • 0000846994 scopus 로고
    • Patulin
    • (Purchase, J. F. H., Ed.) Elsevier, Amsterdam
    • Scott, P. M. (1974) Patulin. In Mycotoxins (Purchase, J. F. H., Ed.) pp 383-403, Elsevier, Amsterdam.
    • (1974) Mycotoxins , pp. 383-403
    • Scott, P.M.1
  • 3
    • 0001812188 scopus 로고
    • Patulin, penicillic acid, and other carcinogenic lactones
    • (Ciegler, A., Kadis, S., and Ajil, S. J., Eds.) Academic Press, New York
    • Ciegler, A., Detroy, R. W., and Lillehoj, E. B. (1971) Patulin, penicillic acid, and other carcinogenic lactones. In Microbial Toxins (Ciegler, A., Kadis, S., and Ajil, S. J., Eds.) Vol. VI, pp 409-434, Academic Press, New York.
    • (1971) Microbial Toxins , vol.6 , pp. 409-434
    • Ciegler, A.1    Detroy, R.W.2    Lillehoj, E.B.3
  • 4
    • 0020067317 scopus 로고
    • Patulin, a further clastogenic mycotoxin, is negative in the SCE assay in Chinese hamster V79-E cells in vitro
    • Thust, R., Kneist, S., and Mendel, J. (1982) Patulin, a further clastogenic mycotoxin, is negative in the SCE assay in Chinese hamster V79-E cells in vitro. Mutat. Res. 10, 91-97.
    • (1982) Mutat. Res. , vol.10 , pp. 91-97
    • Thust, R.1    Kneist, S.2    Mendel, J.3
  • 5
    • 0018903064 scopus 로고
    • Chromosomal analysis in bone-marrow cells of Chinese hamsters after treatment with mycotoxins
    • Korte, A. (1980) Chromosomal analysis in bone-marrow cells of Chinese hamsters after treatment with mycotoxins. Mutat. Res. 78, 41-49.
    • (1980) Mutat. Res. , vol.78 , pp. 41-49
    • Korte, A.1
  • 7
    • 0031927107 scopus 로고    scopus 로고
    • Aneuploidogenic and clastogenic potential of the mycotoxins citrinin and patulin
    • Pfeiffer, E., Gross, K., and Metzler, M. (1998) Aneuploidogenic and clastogenic potential of the mycotoxins citrinin and patulin. Carcinogenesis 19, 1313-1318.
    • (1998) Carcinogenesis , vol.19 , pp. 1313-1318
    • Pfeiffer, E.1    Gross, K.2    Metzler, M.3
  • 8
    • 0002879643 scopus 로고
    • Carcinogenic activity of a series of reactive lactones and related substances
    • Dickens, F., and Jones, H. K. (1961) Carcinogenic activity of a series of reactive lactones and related substances. Br. J. Cancer 15, 85-100.
    • (1961) Br. J. Cancer , vol.15 , pp. 85-100
    • Dickens, F.1    Jones, H.K.2
  • 10
    • 0007969155 scopus 로고
    • The mechanism of the antibiotic action of clavacin and penicillic acid
    • Geiger, W. B., and Conn, J. E. (1945) The mechanism of the antibiotic action of clavacin and penicillic acid. J. Am. Chem. Soc. 67, 112-116.
    • (1945) J. Am. Chem. Soc. , vol.67 , pp. 112-116
    • Geiger, W.B.1    Conn, J.E.2
  • 11
    • 0343146229 scopus 로고
    • Untersuchungen über die inaktivierung des mykotoxins patulin durch sulfhydrylgruppen
    • Hofmann, K., Mintzlaff, H.-J., Alperden, I., and Leistner, L. (1971) Untersuchungen über die Inaktivierung des Mykotoxins Patulin durch Sulfhydrylgruppen. Die Fleischwirtschaft 51, 1534-1537.
    • (1971) Die Fleischwirtschaft , vol.51 , pp. 1534-1537
    • Hofmann, K.1    Mintzlaff, H.-J.2    Alperden, I.3    Leistner, L.4
  • 12
    • 0025639873 scopus 로고
    • Detoxification of patulin by adduct formation with cysteine
    • Lindroth, S., and Wright, A. v. (1990) Detoxification of patulin by adduct formation with cysteine. J. Environ. Pathol. Toxicol. Oncol. 10, 254-259.
    • (1990) J. Environ. Pathol. Toxicol. Oncol. , vol.10 , pp. 254-259
    • Lindroth, S.1    Wright, A.V.2
  • 13
    • 0242309857 scopus 로고
    • Binding of patulin and penicillic acid to glutathione and cysteine and toxicity of the resulting adducts
    • Lieu, F. Y., and Bullerman, L. B. (1978) Binding of patulin and penicillic acid to glutathione and cysteine and toxicity of the resulting adducts. Milchwissenschaft 33, 16-20.
    • (1978) Milchwissenschaft , vol.33 , pp. 16-20
    • Lieu, F.Y.1    Bullerman, L.B.2
  • 14
    • 26844473978 scopus 로고    scopus 로고
    • Kinetic analysis of the chronology of patulin- and gossypol-induced cytotoxicity in vitro
    • Barhoumi, R., and Burghardt, R. C. (1996) Kinetic analysis of the chronology of patulin- and gossypol-induced cytotoxicity in vitro. Fundam. Appl. Toxicol. 30, 290-297.
    • (1996) Fundam. Appl. Toxicol. , vol.30 , pp. 290-297
    • Barhoumi, R.1    Burghardt, R.C.2
  • 15
    • 0025736665 scopus 로고
    • The mechanism of patulin's cytotoxicity and the antioxidant activity of indole tetramic acids
    • Riley, R. T., and Showker, J. L. (1991) The mechanism of patulin's cytotoxicity and the antioxidant activity of indole tetramic acids. Toxicol. Appl. Pharmacol. 109, 108-126.
    • (1991) Toxicol. Appl. Pharmacol. , vol.109 , pp. 108-126
    • Riley, R.T.1    Showker, J.L.2
  • 17
    • 0015890502 scopus 로고
    • Inhibition of alcohol and lactic dehydrogenases by patulin and penicillic acid in vitro
    • Ashoor, S. H., and Chu, F. S. (1973) Inhibition of alcohol and lactic dehydrogenases by patulin and penicillic acid in vitro. Food Cosmet. Toxicol. 11, 617-624.
    • (1973) Food Cosmet. Toxicol. , vol.11 , pp. 617-624
    • Ashoor, S.H.1    Chu, F.S.2
  • 18
    • 0029550426 scopus 로고
    • Evaluation of certain food additives and contaminants
    • 44th Report of the Joint WHO/FAO Expert Committee on Food Additives
    • World Health Organization (1995) Evaluation of certain food additives and contaminants. WHO Technical Report Series, Vol. 859, pp 36-38, 44th Report of the Joint WHO/FAO Expert Committee on Food Additives.
    • (1995) WHO Technical Report Series , vol.859 , pp. 36-38
  • 19
    • 0015713401 scopus 로고
    • Inhibition of muscle aldolase by penicillic acid and patulin in vitro
    • Ashoor, S. H., and Chu, F. S. (1973) Inhibition of muscle aldolase by penicillic acid and patulin in vitro. Food Cosmet. Toxicol. 11, 995-1000.
    • (1973) Food Cosmet. Toxicol. , vol.11 , pp. 995-1000
    • Ashoor, S.H.1    Chu, F.S.2
  • 20
    • 0343581802 scopus 로고
    • Cytotoxicity of patulin and its effect on lambda DNA cleavage by restriction endonuclease
    • Lee, K. S. (1991) Cytotoxicity of patulin and its effect on lambda DNA cleavage by restriction endonuclease. Korean J. Toxicol. 7, 157-163.
    • (1991) Korean J. Toxicol. , vol.7 , pp. 157-163
    • Lee, K.S.1
  • 21
    • 0023214930 scopus 로고
    • Strand scissions of DNA by patulin in the presence of reducing agents and cupric ions
    • Lee, K. S., and Röschenthaler, R. (1987) Strand scissions of DNA by patulin in the presence of reducing agents and cupric ions. J. Antibiot. 40, 692-696.
    • (1987) J. Antibiot. , vol.40 , pp. 692-696
    • Lee, K.S.1    Röschenthaler, R.2
  • 22
    • 0006339848 scopus 로고
    • Patulin
    • (Rodricks, J. V., Ed.) Pathotox Publishers Inc., Park Forest South, IL
    • Ciegler, A. (1977) Patulin. In Mycotoxins in Human and Animal Health (Rodricks, J. V., Ed.) pp 609-624, Pathotox Publishers Inc., Park Forest South, IL.
    • (1977) Mycotoxins in Human and Animal Health , pp. 609-624
    • Ciegler, A.1
  • 24
    • 0017143224 scopus 로고
    • Teratogenicity of patulin and patulin adducts formed with cysteine
    • Ciegler, A., Beckwith, A. C., and Jackson, L. K. (1976) Teratogenicity of patulin and patulin adducts formed with cysteine. Appl. Environ. Microbiol. 31, 664-667.
    • (1976) Appl. Environ. Microbiol. , vol.31 , pp. 664-667
    • Ciegler, A.1    Beckwith, A.C.2    Jackson, L.K.3
  • 25
    • 0000555868 scopus 로고
    • Stability of patulin and penicillic acid in fruit juices and flour
    • Scott, P. M., and Somers, E. (1968) Stability of patulin and penicillic acid in fruit juices and flour. J. Agric. Food Chem. 16, 483-485.
    • (1968) J. Agric. Food Chem. , vol.16 , pp. 483-485
    • Scott, P.M.1    Somers, E.2
  • 26
    • 84987317174 scopus 로고
    • Effect of water activity on disappearance of patulin and citrinin from grains
    • Harwig, J., Blanchfield, B. J., and Jarvis, G. (1977) Effect of water activity on disappearance of patulin and citrinin from grains. J. Food Sci. 42, 1225-1228.
    • (1977) J. Food Sci. , vol.42 , pp. 1225-1228
    • Harwig, J.1    Blanchfield, B.J.2    Jarvis, G.3
  • 27
    • 0032703307 scopus 로고    scopus 로고
    • The mycotoxin patulin induces intra- and intermolecular protein crosslinks in vitro involving cysteine, lysine, and histidine side chains, and α-amino groups
    • Fliege, R., and Metzler, M. (1999) The mycotoxin patulin induces intra- and intermolecular protein crosslinks in vitro involving cysteine, lysine, and histidine side chains, and α-amino groups. Chem.-Biol. Interact. 123, 85-103.
    • (1999) Chem.-biol. Interact. , vol.123 , pp. 85-103
    • Fliege, R.1    Metzler, M.2
  • 28
    • 0000057208 scopus 로고
    • Patulin in the common cold. II. Biochemistry and chemistry
    • Birkinshaw, J. H., Michael, S. E., Bracken, A., and Raistrick, H. (1943) Patulin in the common cold. II. Biochemistry and chemistry. Lancet 245, 625-630.
    • (1943) Lancet , vol.245 , pp. 625-630
    • Birkinshaw, J.H.1    Michael, S.E.2    Bracken, A.3    Raistrick, H.4
  • 29
    • 0020553758 scopus 로고
    • Patulin biosynthesis: Enzymatic and nonenzymatic transformation of the mycotoxin (E)-ascladiol
    • Sekiguchi, J., Shimamoto, T., Yamada, Y., and Gaucher, G. M. (1983) Patulin biosynthesis: enzymatic and nonenzymatic transformation of the mycotoxin (E)-ascladiol. Appl. Environ. Microbiol. 45, 1939-1942.
    • (1983) Appl. Environ. Microbiol. , vol.45 , pp. 1939-1942
    • Sekiguchi, J.1    Shimamoto, T.2    Yamada, Y.3    Gaucher, G.M.4
  • 31
    • 0034128518 scopus 로고    scopus 로고
    • Electrophilic properties of patulin. N-acetylcysteine and glutathione adducts
    • Fliege, R., and Metzler, M. (1999) Electrophilic properties of patulin. N-Acetylcysteine and glutathione adducts. Chem. Res. Toxicol. 13, 373-381.
    • (1999) Chem. Res. Toxicol. , vol.13 , pp. 373-381
    • Fliege, R.1    Metzler, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.