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Volumn 40, Issue 9, 2001, Pages 1704-1705

Stephanosporin, a "traceless" precursor of 2-chloro-4-nitrophenol in the gasteromycete Stephanospora caroticolor

Author keywords

Fungi; Natural products; Nitro compounds; Organochloro compounds; Phenols

Indexed keywords

PHENOLS; POTASSIUM COMPOUNDS; TOXIC MATERIALS;

EID: 0035805276     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (41)

References (29)
  • 1
    • 85007627993 scopus 로고    scopus 로고
    • note
    • Some extracts, especially from dried or aged mushrooms, contained only pigment 2.
  • 2
    • 85007650801 scopus 로고
    • PhD Thesis, Universität Bonn
    • J. Klein, PhD Thesis, Universität Bonn, 1989.
    • (1989)
    • Klein, J.1
  • 4
    • 0014165524 scopus 로고
    • a) M. Polster, Arch. Exp. Veterinaermed. 1967, 21, 299-305 [Chem. Abst. 1968, 68, 19912z];
    • (1968) Chem. Abst. , vol.68 , pp. 19912z
  • 5
    • 4243508806 scopus 로고
    • (ICI), GB 568949, 1945
    • b) W. A. Sexton, F. L. Sharp (ICI), GB 568949, 1945 [Chem. Abstr. 1947, 41, 4272a];
    • (1947) Chem. Abstr. , vol.41 , pp. 4272a
    • Sexton, W.A.1    Sharp, F.L.2
  • 7
    • 4243715369 scopus 로고
    • c) S. Dahl, A. M. Kaplan, J. Am. Leather Chem. Assoc. 1958, 53, 103-118 [Chem. Abstr. 1958, 52, 19206e].
    • (1958) Chem. Abstr. , vol.52 , pp. 19206e
  • 8
    • 85007642728 scopus 로고    scopus 로고
    • note
    • We are grateful to Prof. M. Spiteller, Dortmund, for the ESI-MS measurements.
  • 9
    • 4243730369 scopus 로고
    • (Bayer-AG), DE, 2614825, 1976
    • a) 2-Amino-6-chloro-4-nitrophenol: K. Linhart, A. Friedrich (Bayer-AG), DE, 2614825, 1976 [Chem. Abstr. 1978, 88, 22374u]; 3: W. Ried, M. Butz. Justus Liebigs. Ann. Chem. 1968, 716, 190-197;
    • (1978) Chem. Abstr. , vol.88 , pp. 22374u
    • Linhart, K.1    Friedrich, A.2
  • 10
    • 84982075404 scopus 로고
    • a) 2-Amino-6-chloro-4-nitrophenol: K. Linhart, A. Friedrich (Bayer-AG), DE, 2614825, 1976 [Chem. Abstr. 1978, 88, 22374u]; 3: W. Ried, M. Butz. Justus Liebigs. Ann. Chem. 1968, 716, 190-197;
    • (1968) Justus Liebigs. Ann. Chem. , vol.716 , pp. 190-197
    • Ried, W.1    Butz, M.2
  • 12
    • 0009522775 scopus 로고
    • For acyl diazenes as activated carboxylic acid derivatives, see R. B. Kelly, G. R. Umbreit, W. F. Liggett, J. Org. Chem. 1964, 29, 1273-1275; H. B. Milne, C. F. Most, Jr., J. Org. Chem. 1968, 33, 169-175.
    • (1964) J. Org. Chem. , vol.29 , pp. 1273-1275
    • Kelly, R.B.1    Umbreit, G.R.2    Liggett, W.F.3
  • 13
    • 0014240848 scopus 로고
    • For acyl diazenes as activated carboxylic acid derivatives, see R. B. Kelly, G. R. Umbreit, W. F. Liggett, J. Org. Chem. 1964, 29, 1273-1275; H. B. Milne, C. F. Most, Jr., J. Org. Chem. 1968, 33, 169-175.
    • (1968) J. Org. Chem. , vol.33 , pp. 169-175
    • Milne, H.B.1    Most, C.F.2
  • 14
    • 0015303862 scopus 로고
    • a) For an analogous decomposition of the antibiotic spinamycin, see E. M. Kosower, T. Miyadera, J. Med. Chem. 1972, 15, 307-312
    • (1972) J. Med. Chem. , vol.15 , pp. 307-312
    • Kosower, E.M.1    Miyadera, T.2
  • 15
    • 0013945586 scopus 로고
    • b) for the isolation and structure of spinamycin, see E. L. Wang, M. Hamada, Y. Okami, H. Umezawa, J. Antibiot. Ser. A 1966, 19, 216-221; H. Naganawa, T. Takita, K. Maeda, H. Umezawa, J. Antibiot. 1968, 21, 241-242.
    • (1966) J. Antibiot. Ser. A , vol.19 , pp. 216-221
    • Wang, E.L.1    Hamada, M.2    Okami, Y.3    Umezawa, H.4
  • 16
    • 0014265018 scopus 로고
    • b) for the isolation and structure of spinamycin, see E. L. Wang, M. Hamada, Y. Okami, H. Umezawa, J. Antibiot. Ser. A 1966, 19, 216-221; H. Naganawa, T. Takita, K. Maeda, H. Umezawa, J. Antibiot. 1968, 21, 241-242.
    • (1968) J. Antibiot. , vol.21 , pp. 241-242
    • Naganawa, H.1    Takita, T.2    Maeda, K.3    Umezawa, H.4
  • 17
    • 0002840808 scopus 로고
    • For the properties of phenyldiimine and its decomposition by a radical mechanism, see J. Nicholson, S. G. Cohen, J. Am. Chem. Soc. 1966, 88, 2247-2252; P. C. Huang, E. M. Kosower, J. Am. Chem. Soc. 1968, 90, 2367-2376; A. Heesing, B.-U. Kaiser, Tetrahedron Lett. 1970, 32, 2845-2848; E. M. Kosower, Acc. Chem. Res. 1971, 4, 193-198.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 2247-2252
    • Nicholson, J.1    Cohen, S.G.2
  • 18
    • 0001741848 scopus 로고
    • For the properties of phenyldiimine and its decomposition by a radical mechanism, see J. Nicholson, S. G. Cohen, J. Am. Chem. Soc. 1966, 88, 2247-2252; P. C. Huang, E. M. Kosower, J. Am. Chem. Soc. 1968, 90, 2367-2376; A. Heesing, B.-U. Kaiser, Tetrahedron Lett. 1970, 32, 2845-2848; E. M. Kosower, Acc. Chem. Res. 1971, 4, 193-198.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 2367-2376
    • Huang, P.C.1    Kosower, E.M.2
  • 19
    • 0343699943 scopus 로고
    • For the properties of phenyldiimine and its decomposition by a radical mechanism, see J. Nicholson, S. G. Cohen, J. Am. Chem. Soc. 1966, 88, 2247-2252; P. C. Huang, E. M. Kosower, J. Am. Chem. Soc. 1968, 90, 2367-2376; A. Heesing, B.-U. Kaiser, Tetrahedron Lett. 1970, 32, 2845-2848; E. M. Kosower, Acc. Chem. Res. 1971, 4, 193-198.
    • (1970) Tetrahedron Lett. , vol.32 , pp. 2845-2848
    • Heesing, A.1    Kaiser, B.-U.2
  • 20
    • 33947292961 scopus 로고
    • For the properties of phenyldiimine and its decomposition by a radical mechanism, see J. Nicholson, S. G. Cohen, J. Am. Chem. Soc. 1966, 88, 2247-2252; P. C. Huang, E. M. Kosower, J. Am. Chem. Soc. 1968, 90, 2367-2376; A. Heesing, B.-U. Kaiser, Tetrahedron Lett. 1970, 32, 2845-2848; E. M. Kosower, Acc. Chem. Res. 1971, 4, 193-198.
    • (1971) Acc. Chem. Res. , vol.4 , pp. 193-198
    • Kosower, E.M.1
  • 21
    • 85007637240 scopus 로고    scopus 로고
    • note
    • 6-chloro-4-nitro-1,2-quinone-2-diazide (3) is obtained when stephanosporin is oxidized with iodine in methanol.
  • 22
    • 0032563916 scopus 로고    scopus 로고
    • C. R. Millington, R. Quarrell, G. Lowe. Tetrahedron Lett. 1998, 39, 7201-7204; F. Stieber, U. Grether, H., Waldmann. Angew. Chem. 1999, 111, 1142-1145; Angew. Chem. Int. Ed. 1999, 38, 1073-1077; review: S. Bräse, S. Dahmen. Chem. Eur. J. 2000, 6, 1899-1905.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7201-7204
    • Millington, C.R.1    Quarrell, R.2    Lowe, G.3
  • 23
    • 0032563916 scopus 로고    scopus 로고
    • C. R. Millington, R. Quarrell, G. Lowe. Tetrahedron Lett. 1998, 39, 7201-7204; F. Stieber, U. Grether, H., Waldmann. Angew. Chem. 1999, 111, 1142-1145; Angew. Chem. Int. Ed. 1999, 38, 1073-1077; review: S. Bräse, S. Dahmen. Chem. Eur. J. 2000, 6, 1899-1905.
    • (1999) Angew. Chem. , vol.111 , pp. 1142-1145
    • Stieber, F.1    Grether, U.2    Waldmann, H.3
  • 24
    • 0033583545 scopus 로고    scopus 로고
    • C. R. Millington, R. Quarrell, G. Lowe. Tetrahedron Lett. 1998, 39, 7201-7204; F. Stieber, U. Grether, H., Waldmann. Angew. Chem. 1999, 111, 1142-1145; Angew. Chem. Int. Ed. 1999, 38, 1073-1077; review: S. Bräse, S. Dahmen. Chem. Eur. J. 2000, 6, 1899-1905.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1073-1077
  • 25
    • 0041054503 scopus 로고    scopus 로고
    • C. R. Millington, R. Quarrell, G. Lowe. Tetrahedron Lett. 1998, 39, 7201-7204; F. Stieber, U. Grether, H., Waldmann. Angew. Chem. 1999, 111, 1142-1145; Angew. Chem. Int. Ed. 1999, 38, 1073-1077; review: S. Bräse, S. Dahmen. Chem. Eur. J. 2000, 6, 1899-1905.
    • (2000) Chem. Eur. J. , vol.6 , pp. 1899-1905
    • Bräse, S.1    Dahmen, S.2
  • 27
    • 85007634032 scopus 로고    scopus 로고
    • note
    • 1 is only weakly active against bacteria and fungi. We are grateful to Prof. T. Anke, Kaiserslautern, for this information.
  • 28
    • 85007634039 scopus 로고    scopus 로고
    • note
    • We thank Dipl.-Biol. Christoph Hahn and Dr. Norbert Arnold for kindly supplying L. trachyspora that was collected in October 1998 on driftwood at the Rissbach (Karwendel Mountains, Bavaria).
  • 29
    • 0001400072 scopus 로고
    • F. Oberwinkler, E. Horak. Plant Syst. Evol. 1979, 131, 157-164. We thank Prof. F. Oberwinkler. Tübingen, for suggesting this investigation.
    • (1979) Plant Syst. Evol. , vol.131 , pp. 157-164
    • Oberwinkler, F.1    Horak, E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.