Studies on the Metabolites ofAspergillus versicolor (Vuillemin) Tiraboschi
- 1 January 1967
- journal article
- research article
- Published by Oxford University Press (OUP) in Agricultural and Biological Chemistry
- Vol. 31 (1) , 11-17
- https://doi.org/10.1080/00021369.1967.10858763
Abstract
Three new pigments, named versicolorins A, B and C, metabolites from the mycelium of Aspergillus versicolor, have been isolated. Versicolorin A, C18H10O7, is fine orange yellow needles, m.p. 289[degree]C (decomp.), [[alpha]]D-354[degree]. It is an anthraquinoid pigment having 3 hydroxyl groups and a vinyl ether system contained in a 5-membered ring. Versicolorin A trimethyl ether was hydrogenated to a dihydro-derivatlve, and by oxidation gave 3,5-dimethoxyphthalic acid and a hydroxy acid which may be 1,6,8-trimethoxy-3-hydroxy anthraquinone-2-carboxylic acid. These chemical behavior and NMR data indicate the probable structure of versicolorin. Versicolorin B, C18H12O7, is fine orange yellow needles, m.p., 298[degree]C (decomp.) [[alpha]]D-223[degree]. Its trimethyl ether is identical with that of dihydroversi-colorin A. Versicolorin C, C18H12O7, is orange red needles, m.p.> 310[degree]C, [[alpha]]D 0[degree]. Comparison of optical properties, IR and NMR spectra of versicolorin B and its methyl ether with those of versicolorin C and its methyl ether indicates that versicolorin C is very probably a racemate of versicolorin B.This publication has 0 references indexed in Scilit: