Fusaric acid

Fusaric Acid (2). The biosynthetic origin of fusaric acid (2) from two distinct biogenetic units derived from [ l- C]acetate and [2- C]acetate administered in replacement cultures of Fusarium oxysporum was impressively demonstrated by the C-satellite method.  

In fusaric acid labelled by [l- C]acctate, satellite peaks from C-4-H, C-6-H, C-8-H, and C-IO-H were directly determined. After reduction of the 

An interesting feature of this study was the preliminary use of C-labelled acetates and aspartate to determine optimal growth and culture conditions. These conditions were then applied to growth on the more expensive Relabelled substrates, which would result in minimal dilution of isotope. 

The C-satellite enrichment data show the polyketide origin of variotin  

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Fusaric acid (5-n-butylpyridine-2-carboxylic acid) [536-69-6] M 179.2, m 96-98°, 98°, 98-100°, 101-103°, pK] 5.7, pK2 6.16 (80% aq methoxyethanol). Dissolve in CHCI3, dry (Na2S04), filter, evaporate and recrystallise the residue from 50 parts of pet ether (b 40-60°) or EtOAc, then sublime in vacuo. The copper salt forms bluish violet crystals from H2O and has m 258-259°. [Hardegger and Nikles Helv Chim Acta 39 505 1956 Schreiber and Adam Chem Ber 93 1848 1960 NMR and MS Tschesche and Fuhrer Chem Ber 111 3500 1978.]... 

Notz R, M Maurhofer, H Dubach, D Haas, G Defago (2002) Fusaric acid-producing strains of Fusarium oxysporum alter 2,4-diacetylphloroglucinol biosynthetic gene expression in Pseudomonas fluorescens CHAO and in the rhizosphere of wheat. Appl Environ Microbiol 68 2229-2235. 

Tjeerd van Rij E, G Girard, BJJ Lugtenberg, GV Bloemberg (2005) Influence of fusaric acid on phenazine-1-carboxamide synthesis and gene expression of Pseudomonas chlororaphis strain PCL1391. Microbiology (UK) 151 2805-2814. 

Utsumi R et al. (1991) Molecular cloning and characterization of the fusaric acid-resistance gene from Pseudomonas cepacia. Agric Biol Chem 55 1913-1918. 

As the result of a screening program examining microbial fermentation products for pharmacological activity (other than antibiotic activity), fusaric acid (10) was isolated from Fusarium oxysporum following the discovery that extracts were potent inhibitors of dopamine p-hydroxylase, and thus interfered with the biosynthesis in vivo of the pressor neurohormone, norepinephrine. To refine this lead, amidation of 10 via the acid chloride was carried out... 

An enzyme inhibitor of microbial origin with a simple structure, fusaric acid (XXXIV), is a hypotensive agent. This compound has been tested clinically as the free acid (29) and as the calcium salt (30) and is orally effective in man with a low incidence of side-effects. Dopamine-p-hydroxylase inhibitory action of this compound has been demonstrated in man (29). 

Introduction of chlorine or bromine into the 3- and/or 4- positions of the side chain yields more potent compounds in terms of hypotension in rats and dopamine p- hydroxylase inhibition (31. 32). The analog YP-279 (XXXV) is also hypotensive in rats but is said not to affect brain norepinephrine biosynthesis unlike fusaric acid or dibromofusaric acid (33-35). Fusaric acid amide (bupicomide, Sch 10595, XXXVI) is clinically effective at 300 to 1800 mg per day and is said to have hemodynamic effects similar to hydralazine (36. 37). The amide is... 

Butylpicolinic acid (fusaric acid, 4.68) is a major metabolite of 5-bu-tylpicolinamide (SCH 10985, 4.67) in the plasma of rats, dogs, and humans. The biological activity of this compound (an inhibitor of dopamine-/3-hy-droxylase) is mainly due to its metabolite fusaric acid, indicating that, in this example, the hydrolysis of the amide group is bioactivating [41]. 

Fumonisins, beauvericin, moniliformin, naphthoquinone pigments, fusaric acid, fusarin C, gibebyrones see fumonisin producers... 

Fusaric acid (5-w-butylpyridine-2-carboxylic acid) [536-69-6] M 179.2, m 96-98°, 98°, 98-100°, 101-103°. Dissolve in CHCI3, dry (Na2S04), filter, evaporate and recrystallise the residue from 50... 

Irish research (Lawlor and Lynch, 2001) has shown that cereals grown there may be contaminated with vomitoxin, zearalenone, fusaric acid or ochratoxin. The presence of aflatoxins in animal feeds in Ireland is considered likely to be due to the importation of feed ingredients from warmer climates. 

In the presence of alkylchloroformate esters, Ws(tributylstannyl)acetylene has been used in the 2-ethynylation of pyridines <94T(50)13089>. An unexpected regioselectivity has been observed in the rearrangement of 3-pyridyl thiophosphates to 2- and 4-pyridyl thiophosphonates <94ZOK(64)610>. A method for introduction of acyl carbon functional groups using trimethylstannyl pyridine (45) was explored and applied to making fusaric acid (46) (Scheme 34) <95H(41)817>. 

Iwahashi H, Kawamori H, Fukushima K. Quinolinic acid, a-picolinic acid, fusaric acid, and 2,6-pyridinedicarboxylic acid enhance the Fenton reaction in phosphate buffer. Chem-Biol Interact 1999 118 201-215. 

Fusaric acid (= 5-Butyl-2- Fusarium heterosporium (fungal pathogen DBH (Tyr H)... 

FURYL PHENYL KETONE see FQ0050 FUSARENONE X see FQROOO FUSARIC ACID see BSIOOO FUSARINIC ACID see BSIOOO FUSARIOTOXIN T 2 see FQSOOO FUSED BORAX see DXG035... 

Agents that can inhibit dopamine-P-hydroxylase include disulfiram, fusaric acid, phenylpropargylamine, FLA 63, FLA 57, LY 10853 and SKF 102698. These agents are of value in experimental investigations, but none Is used clinically for this purpose (though disulfiram is used to modify ethanol metabolism by a different mechanism see aldehyde DEHYDROGENASE INHIBITORS). 

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