Isolation and characterization of substituted 4-hydroxy-cyclohex-2-enones as metabolites of 3,4-dimethoxybenzyl alcohol and its methyl ether in ligninolytic cultures ofPhanerochaete chrysosporium
✍ Scribed by Urs M. Tuor; Hans E. Schoemaker; Matti S. A. Leisola; Harald W. H. Schmidt
- Publisher
- Springer
- Year
- 1993
- Tongue
- English
- Weight
- 694 KB
- Volume
- 38
- Category
- Article
- ISSN
- 1432-0614
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✦ Synopsis
The metabolism of quinones formed in the enzymatic oxidation of veratryl alcohol (3,4-dimethoxybenzyl alcohol) (Ia) and its methyl ether Ib in ligninolytic cultures of Phanerochaete chrysosporium was studied. A metabolite of 2-hydroxymethyl-5-methoxy-2,5cyclohexadiene-l,4-dione (IIa, formed from Ia by oxidation) was isolated and identified as cis-4-hydroxy-6-hydroxymethyl-3-methoxy-cyclohex-2-en-one (IVa), formally the reduced hydroquinone IIIa. The formation of IYa was also observed when both veratryl alcohol Ia or 2,5-dihydroxy-4-methoxybenzyl alcohol (IIIa), the hydroquinone of IIa, were used as substrates. Analogously, cis-4-hydroxy-3-methoxy-6-methoxymethyl-cyclohex-2-en-one (IYe) was isolated and identified as a metabolite from either 3,4-dimethoxybenzyl methyl ether (Ib) or from its oxidation product 5-methoxy-2-methoxymethyl-2,5-cyclohexadiene-l,4-dione (IIb) as well as from the corresponding hydroquinone 2,5-dihydroxy-4-methoxybenzyl methyl ether (IIIe). The physiological role of these unprecedented conversions is discussed.