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Decomposition in Soil of Emodin, Chrysophanic Acid, and a Mixture of Anthraquinones Synthesized by an Aspergillus glaucus Isolate¹

ABSTRACT

A. glaucus synthesized 17 – 22 anthraquinones, and one to four phenolic compounds depending on cultural conditions and incubation time. The anthraquinones extracted from the culture media were equivalent to 10% or more of the total mycelium plus melanin polymers recovered. Based on two-dimensional thin-layer chromatography and cochromatography with reference compounds before and after separation on a silica gel column and on UV spectra, dominant anthraquinones included emodin, catenarin, physcion, erythroglaucin, endocrocin, and probably parietinic acid and questin. One of the phenols was orcinol. The anthraquinone mixtures, synthesized by A. glaucus under different cultural conditions, were only slowly degraded in soil. During a 12-week incubation period the C losses ranged from 11 – 23%, while 69 and 47%, respectively, of emodin and chrysophanic acid C were evolved as CO₂. Emodin when "linked" into peroxidase polymers was relatively stable to biodegradation during the earlier stages of incubation only. When in intimate physical association with a model humic acid-type polymer, little protection was observed. The ¹⁴C-labeled A. glaucus anthraquinone mixture when "linked" to phenolase polymer showed a biodegradability reduction from about 25 – 11% during 12 weeks.

¹ Contribution from Department of Soil and Environmental Sciences, University of California, Riverside, CA 92521 and Instituto de Microbiologia, Universidade Federal do Rio de Janeiro, Brazil.

² Visiting Professor of Microbiology from Univ. of Rio de Janeiro, Brazil, and Professor of Soil Science, Univ. of California, Riverside, respectively.

Received for publication January 22, 1979. Accepted for publication March 26, 1979.