Novel benzotropolone and 2H-furo[3,2-b]benzopyran-2-one pigments from Tricholoma aurantium (Agaricales)

European Journal of Organic Chemistry

Volumn , Issue 4, 2000, Pages 603-609

  Klostermeyer, Dörte ^a   Knops, Liliana ^a   Sindlinger, Tilman ^a   Polborn, Kurt ^a   Steglich, Wolfgang ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

(E) 2 Nonenal; 2,3 Benzotropolone; 2H Furo 3,2 b benzopyran 2 ones; Toadstools; Tricholoma

Indexed keywords

AURANTRICHOLIDE A; AURANTRICHOLIDS B; AURANTRICHOLONE; PIGMENT; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; AUTOFLUORESCENCE; CHEMICAL STRUCTURE; CONTROLLED STUDY; EXTRACTION; MUSHROOM; NONHUMAN; PHYTOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0034005721     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(200002)2000:4<603::AID-EJOC603>3.0.CO;2-5     Document Type: Article

References (21)

1. L. Knops, M. Nieger, B. Steffan, B. W. Steglich, Liebigs Ann. 1995, 77-80.
2. A. Gamba Invernizzi, G. Vidari, P. Vita-Finzi, Tetrahedron Lett. 1995, 36, 1905-1908.
3. F. Benevelli, O. Carugo, A. Gamba Invernizzi, G. Vidari, Tetrahedron Lett. 1995, 36, 3035-3083.
4. D. Klostermeyer, Dissertation, Universität München, 1996.
5. P. D. Collier, T. Bryce, R. Mallows, P. E. Thomas, D. J. Frost, O. Korver, C. K. Wilkins, Tetrahedron 1973, 29, 125-142.
6. G.-I. Nonaka, F. Hashimoto, I. Nishioka, Chem. Pharm. Bull. 1986, 34, 61-65.
7. A. L. Davis, Y. Cai, A. P. Davies, Magn. Reson. Chem. 1995, 33, 549-552.
8. A. C. Campbell, M. S. Maidment, J. H. Pick, D. F. M. Stevenson, J. Chem. Soc., Perkin Trans. 1, 1985, 1567-1576.
9. G. Kollenz, A. Biedermann, K. Peters, E. M. Peters, H. G. von Schnering, J. Chem. Res. 1985, 2976-2994.
10. M. Gill, M. J. Kiefel, D. A. Lally, A. Ten, Aust. J. Chem. 1990, 43, 1497-1518.
11. a of 8.7: S. V. Jovanovic, Y. Hara, S. Steenken, M. G. Simic, J. Am. Chem. Soc. 1977, 119, 5337-5343.
12. a of 8.7: S. V. Jovanovic, Y. Hara, S. Steenken, M. G. Simic, J. Am. Chem. Soc. 1977, 119, 5337-5343.
13. A compound with the structure of aurantricholide B has been isolated along with 3′,4′,4-trihydroxypulvinone from Suillus grevillei: M. Gill, Ph.D. Thesis, University of Bradford, 1973. Cited in M. Gill, Nat. Prod Rep. 1999, 16, 301-317 (ref.[7]).
14. A compound with the structure of aurantricholide B has been isolated along with 3′,4′,4-trihydroxypulvinone from Suillus grevillei: M. Gill, Ph.D. Thesis, University of Bradford, 1973. Cited in M. Gill, Nat. Prod Rep. 1999, 16, 301-317 (ref.[7]).
15. 3. Crystallographic data (excluding the structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-114025. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12, Union Road, Cambridge CB2 1EZ, U.K. [Fax: (internat.) +44 (0)1223/336033; E-mail: deposit@chemcrys.cam.ac.uk].
16. L. Horner, W. Dürckheimer, K.-H. Weber, K. Dölling, Chem. Ber. 1964, 97, 312-324 and literature cited therein.
17. Y. Takino, A. Ferretti, V. Flanagan, M. A. Gianturco, M. Vogel, Can. J. Chem. 1967, 45, 1949-1956.
18. The possibility that the oxidative ring-closure and the benzotropolone condensation depicted in Scheme 2 also occur with the corresponding dihydropulvinones may also be considered.
19. Y. Takino, H. Imagawa, H. Horikawa, A. Tanaka, Agr. Biol. Chem. 1964, 28, 64-71.
20. [18a] W. Steglich, L. Zechlin, Chem. Ber. 1978, 111, 3939-3948.
21. [18b] N. Arpin, J. Favre-Bonvin, W. Steglich, Phytochemistry 1974, 13, 1949-1952.