Details
| Original language | English |
|---|---|
| Pages (from-to) | 305-314 |
| Number of pages | 10 |
| Journal | Journal of biotechnology |
| Volume | 85 |
| Issue number | 3 |
| Publication status | Published - 9 Feb 2001 |
Abstract
The white-rot fungus Pycnoporous cinnabarinus (DMS-1184) was submerged cultured for 22 days under controlled conditions in a bioreactor. After 6, 9, and 15 days of culture the growth medium was supplemented with [5-2H]-labelled ferulic acid (I). The major phenolic compounds identified labelled were four lignans, the methyl esters of ferulic (I) and vanillic acid (VIII), (E)-coniferyl aldehyde (II), (E)-coniferyl alcohol (III), vanillic acid (VIII), vanillin (IX) and vanillyl alcohol (X). The detection of considerable amounts of labelled 4-hydroxy-3-methoxyacetophenone (VII) in the late growth phase suggested the increasing formation and decarboxylation of free 4-hydroxy-3-methoxybenzoylacetic acid (VI) and, thus, a β-oxidation-like degradation of ferulic acid (I) or its methyl ester to vanillic acid (VIII). 4-Hydroxy-3-methoxybenzoylacetic acid methyl ester (VI) and 3-hydroxy-(4-hydroxy-3-methoxyphenyl)-propanoic acid methyl ester (V) were synthesised and then identified as metabolites in the culture medium. The fungal degradation of the phenyl propenoic side chain of ferulic acid (I), a principal key step of lignin decomposition, appeared to proceed analogous to fatty acids.
Keywords
- β-Oxidation, 3-Hydroxy-(4-hydroxy-3-methoxyphenyl)-propanoic acid methyl ester, 4-Hydroxy-3-methoxy-benzoylacetic acid methyl ester, Lignans, Pycnoporous cinnabarinus
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biotechnology
- Chemical Engineering(all)
- Bioengineering
- Immunology and Microbiology(all)
- Applied Microbiology and Biotechnology
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In: Journal of biotechnology, Vol. 85, No. 3, 09.02.2001, p. 305-314.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Phenyl propenoic side chain degradation of ferulic acid by Pycnoporus cinnabarinus
T2 - Elucidation of metabolic pathways using [5-2H]-ferulic acid
AU - Krings, U.
AU - Pilawa, S.
AU - Theobald, C.
AU - Berger, R. G.
N1 - Funding information: The authors are grateful to the Fonds der Chemischen Industrie, Frankfurt for financial support and to M. Schinner, Institute of Organic Chemistry, Hannover University, for 13 C-NMR measurements.
PY - 2001/2/9
Y1 - 2001/2/9
N2 - The white-rot fungus Pycnoporous cinnabarinus (DMS-1184) was submerged cultured for 22 days under controlled conditions in a bioreactor. After 6, 9, and 15 days of culture the growth medium was supplemented with [5-2H]-labelled ferulic acid (I). The major phenolic compounds identified labelled were four lignans, the methyl esters of ferulic (I) and vanillic acid (VIII), (E)-coniferyl aldehyde (II), (E)-coniferyl alcohol (III), vanillic acid (VIII), vanillin (IX) and vanillyl alcohol (X). The detection of considerable amounts of labelled 4-hydroxy-3-methoxyacetophenone (VII) in the late growth phase suggested the increasing formation and decarboxylation of free 4-hydroxy-3-methoxybenzoylacetic acid (VI) and, thus, a β-oxidation-like degradation of ferulic acid (I) or its methyl ester to vanillic acid (VIII). 4-Hydroxy-3-methoxybenzoylacetic acid methyl ester (VI) and 3-hydroxy-(4-hydroxy-3-methoxyphenyl)-propanoic acid methyl ester (V) were synthesised and then identified as metabolites in the culture medium. The fungal degradation of the phenyl propenoic side chain of ferulic acid (I), a principal key step of lignin decomposition, appeared to proceed analogous to fatty acids.
AB - The white-rot fungus Pycnoporous cinnabarinus (DMS-1184) was submerged cultured for 22 days under controlled conditions in a bioreactor. After 6, 9, and 15 days of culture the growth medium was supplemented with [5-2H]-labelled ferulic acid (I). The major phenolic compounds identified labelled were four lignans, the methyl esters of ferulic (I) and vanillic acid (VIII), (E)-coniferyl aldehyde (II), (E)-coniferyl alcohol (III), vanillic acid (VIII), vanillin (IX) and vanillyl alcohol (X). The detection of considerable amounts of labelled 4-hydroxy-3-methoxyacetophenone (VII) in the late growth phase suggested the increasing formation and decarboxylation of free 4-hydroxy-3-methoxybenzoylacetic acid (VI) and, thus, a β-oxidation-like degradation of ferulic acid (I) or its methyl ester to vanillic acid (VIII). 4-Hydroxy-3-methoxybenzoylacetic acid methyl ester (VI) and 3-hydroxy-(4-hydroxy-3-methoxyphenyl)-propanoic acid methyl ester (V) were synthesised and then identified as metabolites in the culture medium. The fungal degradation of the phenyl propenoic side chain of ferulic acid (I), a principal key step of lignin decomposition, appeared to proceed analogous to fatty acids.
KW - β-Oxidation
KW - 3-Hydroxy-(4-hydroxy-3-methoxyphenyl)-propanoic acid methyl ester
KW - 4-Hydroxy-3-methoxy-benzoylacetic acid methyl ester
KW - Lignans
KW - Pycnoporous cinnabarinus
UR - http://www.scopus.com/inward/record.url?scp=0035936935&partnerID=8YFLogxK
U2 - 10.1016/S0168-1656(00)00396-5
DO - 10.1016/S0168-1656(00)00396-5
M3 - Article
C2 - 11173097
AN - SCOPUS:0035936935
VL - 85
SP - 305
EP - 314
JO - Journal of biotechnology
JF - Journal of biotechnology
SN - 0168-1656
IS - 3
ER -