Terreinol - A novel metabolite from Aspergillus terreus: Structure and 13C labeling

Tetrahedron Letters

Volumn 45, Issue 1, 2004, Pages 53-55

  Macedo Jr , Fernando C ^a   Porto, André L M ^a   Marsaioli, Anita J ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

Aspergillus terreus; Isotopic labeling; Novel metabolite; Terreinol

Indexed keywords

ALCOHOL DERIVATIVE; POLYKETIDE; TERREIN; TERREINOL; UNCLASSIFIED DRUG;

ARTICLE; ASPERGILLUS TERREUS; BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITE; NUCLEAR OVERHAUSER EFFECT; ULTRAVIOLET SPECTROSCOPY;

ASPERGILLUS; ASPERGILLUS TERREUS;

EID: 0742269840     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.128     Document Type: Article

References (17)

1. Simpson T.J. Top. Curr. Chem. 195:1998;1.
2. Alberts A.W., Chen J., Kuron G., Hunt V., Huff J., Hoffman C., Rothrock J., Lopez M., Joshua H., Harris E., Patchett A., Monaghan R., Currie S., Stapley E., Albers-Schonberg G., Hensens O., Hirshfield J., Hoogsteen K., Liesch J., Springer J. Proc. Natl. Acad. Sci. U.S.A. 77:1980;3957.
3. Raistrick H., Smith G. Biochem. J. 29:1935;606.
4. Kolb H.C., Hoffmann M.R. Tetrahedron: Asymmetry. 1:1990;237.
5. Sheeran J.C., Lawson W.B., Gaul R.J. J. Am. Chem. Soc. 80:1958;5536.
6. Sheeran J.C., Lo Y.S. J. Med. Chem. 17:1974;371.
7. Kiriyama N., Higuchi Y., Yamamoto Y. Chem. Pharm. Bull. 25:1977;1265.
8. Strain CCT3320 isolated from the Brazilian Atlantic Rain Forest by Fundação Tropical André Tosello.
9. 13C]-D-glucose was added to 100 mL of this medium. In all experiments, the cultures were maintained at 28°C with stirring at 170 rpm in a rotatory shaker.
10. 1a was readily obtained treating 1 with an excess of freshly distilled diazomethane.
11. max MeOH: 222, 282, and 336 nm.
12. Szilágyi L., Fehér K. J. Mol. Struct. 471:1998;195.
13. For a review on spiroketals, see: Perron F., Albizati K.F. Chem. Rev. 89:1989;1617.
14. 3OH).
15. Relaxation delay=20 s; acquisition time=1 s.
16. Freeman R., Hill H.D.W., Kaptein R. J. Magn. Reson. 7:1972;327.
17. Thomas R. ChemBioChem. 2:2001;612.