A proposed mechanism for the conversion of o-coumaric acid to 4-hydroxy-coumarin in Aspergillus fumigatus fresenius

Bye, Ann; Ashton, W. M.; King, Hugh K.

doi:10.1016/0006-291x(68)90431-2

Cited by 4 publications

(3 citation statements)

References 3 publications

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“…Some isolates of A fumigatus produce a steroid like antibiotic, helvolic acid (Wakeman et al 1943). Aspergillus fumigatus has also been reported as being able to synthesise dicoumarol and 4-hydroxy coumarin in cultures containing o-coumaric acid (Bye et al 1968 ;Bye and King 1970). 3,3@-Methylenebis(4-hydroxycoumarin) has anti-coagulant properties and has been identiÐed as the cause of fatal haemorrhagic disease of cattle and could also be implicated in the sporadic outbreaks of haemorrhagic disease in the UK although there is no direct evidence to support this (see haemorrhagic disease in cattle).…”

Section: Storage Derived Mycotoxinsmentioning

confidence: 99%

Occurrence and significance of mycotoxins in forage crops and silage: a review

Scudamore¹,

Livesey

1998

J. Sci. Food Agric.

175

127

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Study of mycotoxins in animal feeding stuffs has concentrated on the occurrence of aflatoxins and, to a lesser extent, other mycotoxins in cereals, raw materials and concentrate feeds. However, ruminant diets contain a high proportion of forage crops such as grass or maize silage, hay and straw. Under adverse growing, production or storage conditions, fungal spoilage is likely to occur with some degree of mycotoxin contamination. The mould flora of forage crops is likely to differ significantly from that of cereals and mycotoxin contamination, should it occur, could differ qualitatively and quantitatively. Information relating to forage crops as a potential source of mycotoxins is reviewed. Some field incidents and animal disease which may be mycotoxin related are discussed and analytical methods are reviewed. Information on dose and effect of candidate mycotoxins is given where available. The review suggests areas which the authors consider merit further study. Crown Copyright 1998.

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Section: Storage Derived Mycotoxinsmentioning

confidence: 99%

Occurrence and significance of mycotoxins in forage crops and silage: a review

Scudamore¹,

Livesey

1998

J. Sci. Food Agric.

175

127

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“…Although the conversion ofo-coumaric acid into 4-hydroxycoumarin has been observed several times (Bocks, 1967;Bellis, Spring & Stoker, 1967;Shieh & Blackwood, 1967) little work has been carried out on the mechanism. It seemed possible that a fl-oxidation mechanism was involved (Bye et al 1968; Spring & Stoker, 1969) and this paper describes a search for intermediates.…”

mentioning

confidence: 94%

“…The temperature may rise to 60°C with production of the haemorrhagic agent dicoumarol (VII) (Stahman, Heubner & Link, 1941). Melilotic acid (o-hydroxyphenylpropionic acid) (I) and o-coumaric acid (IV) both present in A. odoratum, can serve as precursors for dicoumarol production (Bye, Ashton & King, 1968). 4-Hydroxycoumarin (VI) can react nonenzymically with formaldehyde to form dicoumarol * Present address: Weilcome Research Laboratories, Beckenham, Kent, U.K. (Spring & Stoker, 1968).…”

mentioning

confidence: 99%

The biosynthesis of 4-hydroxycoumarin and dicoumarol by Aspergillus fumigatus Fresenius

Bye

King

1970

Biochemical Journal

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A strain of Aspergillus fumigatus Fresenius, isolated from spoiled hay, converts melilotic acid (o-hydroxyphenylpropionic acid) and o-coumaric acid into 4-hydroxycoumarin and dicoumarol. The sequence is shown to be melilotic acid (I) [Formula: see text] coumaric acid (IV) [Formula: see text] beta-hydroxymelilotic acid (II) [Formula: see text] beta-oxomelilotic acid (III) [Formula: see text] 4-hydroxycoumarin (VI), on the basis of (1) studies on the formation of postulated intermediates, (2) experiments with isotopically labelled materials and (3) sequential enzyme induction. In the presence of semicarbazide, o-coumaraldehyde is formed from o-coumaric acid: there is no evidence, however, that this lies on the normal metabolic pathway.

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The Isolation and Identification of Toxic Coumarins

Richards¹

1972

Fungal Toxins

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A proposed mechanism for the conversion of o-coumaric acid to 4-hydroxy-coumarin in Aspergillus fumigatus fresenius

Cited by 4 publications

References 3 publications

Occurrence and significance of mycotoxins in forage crops and silage: a review

Occurrence and significance of mycotoxins in forage crops and silage: a review

The biosynthesis of 4-hydroxycoumarin and dicoumarol by Aspergillus fumigatus Fresenius

The Isolation and Identification of Toxic Coumarins

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