Degradation of the Isoflavone Biochanin A by Fusarium javanicum
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چکیده
Isoflavone, Biochanin A, Dihydrobiochanin A, Phenylacetic acids, Fusarium javanicum After a lag-phase of 1 h a mycelial suspension of Fusarium javanicum completely degraded 5,7-dihydroxy-4'-methoxyisoflavone (biochanin A) to a series of transiently accumulating catabolites. The compounds were elucidated by spectroscopic techniques and are arranged in the first known degradative pathway for an isoflavone: biochanin A -* dihydrobiochanin A -* 3-(/?-methoxyphenyl)-4,6-diketo-5,6-dihydro-4H-pyran -* />-methoxyphenylacetic acid -*■ p-hydroxyphenylacetic acid -*■ 3,4-dihydroxyphenylacetic acid -*■ C 0 2. The carbon atoms of bio chanin A not accounted for by this sequence are discussed in relation to microbial flavonoid pathways.
منابع مشابه
Demethylation, Methylation and 3'-Hydroxylation of Isoflavones bv Fusarium Fungi
Isoflavones, Fusarium, Methylation, Demethylation, 3'-Hydroxylation, Metabolism Several introductionary reactions of isoflavone metabolism by Fusarium fungi are reported. Fu sarium avenaceum hydroxylates formononetin in the 3'-position yielding 3',7-dihydroxy-4'-methoxyisoflavone (calycosin). 3'-Hydroxylation of biochanin A to 3/,5,7-trihydroxy-4/-methoxyisoflavone (pratensein) has been observ...
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Strains of Ascochyta rabiei which are pathogenic to chickpea (Cicer arietinum L.) readily catabolized the main chickpea isoflavone biochanin A (5,7-dihydroxy-4'-methoxyisoflavone). 3'-Hydroxylation and O-demethylation reactions led to the isoflavones pratensein, genistein, and orobol, which were rapidly further degraded. Dihydrogenistein and p-hydroxyphenylacetic acid were also identified as ca...
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