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 -