Moniliformin is the

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula (M⁺ = K⁺ or Na⁺). Both the sodium and potassium salts are generally hydrated, e.g. . In terms of its structure, it is the alkali metal

salt In common usage, salt is a mineral composed primarily of sodium chloride (NaCl). When used in food, especially in granulated form, it is more formally called table salt. In the form of a natural crystalline mineral, salt is also known as r ...

of the conjugate base of 3-hydroxy-1,2-cyclobutenedione (the

enolate In organic chemistry, enolates are organic anions derived from the deprotonation of carbonyl () compounds. Rarely isolated, they are widely used as reagents in the Organic synthesis, synthesis of organic compounds. Bonding and structure Enolate ...

of 1,2,3-cyclobutanetrione), a planar molecule related to

squaric acid Squaric acid or quadratic acid (so named because its four carbon atoms approximately form a square) is a diprotic organic acid with the chemical formula . The conjugate base of squaric acid is the hydrogensquarate anion ; and the conjugate base ...

. It is an unusual

mycotoxin A mycotoxin (from the Greek μύκης , "fungus" and τοξικός , "poisonous") is a toxic secondary metabolite produced by fungi and is capable of causing disease and death in both humans and other animals. The term 'mycotoxin' is usually rese ...

, a feed contaminant that is lethal to

fowl Fowl are birds belonging to one of two biological orders, namely the gamefowl or landfowl ( Galliformes) and the waterfowl ( Anseriformes). Anatomical and molecular similarities suggest these two groups are close evolutionary relatives; toget ...

, especially

duckling Duck is the common name for numerous species of waterfowl in the family Anatidae. Ducks are generally smaller and shorter-necked than swans and geese, which are members of the same family. Divided among several subfamilies, they are a form ta ...

s. Moniliformin is formed in many

cereals A cereal is a grass cultivated for its edible grain. Cereals are the world's largest crops, and are therefore staple foods. They include rice, wheat, rye, oats, barley, millet, and maize (Corn). Edible grains from other plant families, suc ...

by a number of ''

Fusarium ''Fusarium'' (; ) is a large genus of filamentous fungi, part of a group often referred to as hyphomycetes, widely distributed in soil and associated with plants. Most species are harmless saprobes, and are relatively abundant members of the s ...

'' species that include ''

Fusarium moniliforme ''Fusarium verticillioides'' is the most commonly reported fungal species infecting maize (''Zea mays''). ''Fusarium verticillioides'' is the accepted name of the species, which was also known as ''Fusarium moniliforme''. The species has also bee ...

'', ''

Fusarium avenaceum ''Gibberella avenacea'' is a fungus A fungus (: fungi , , , or ; or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and mold (fungus), molds, as well as the more familiar mushrooms. ...

'', '' Fusarium subglutinans'', '' Fusarium proliferatum'', ''

Fusarium fujikuroi ''Gibberella fujikuroi'' is a fungal plant pathogen. It causes ''bakanae'' disease in rice seedlings. Another name is foolish seedling disease. It gets that name because the seeds can be infected, leading to disparate outcomes for the plant. Th ...

'' and others. It is mainly

cardiotoxic Cardiotoxicity is the occurrence of heart dysfunction as electric or muscle damage, resulting in heart toxicity. This can cause heart failure, arrhythmia, myocarditis, and cardiomyopathy in patients. Some effects are reversible, while in others, p ...

and causes

ventricular hypertrophy Ventricular hypertrophy (VH) is thickening of the walls of a ventricle (lower chamber) of the heart. Although left ventricular hypertrophy (LVH) is more common, right ventricular hypertrophy (RVH), as well as concurrent hypertrophy of both vent ...

Biochemistry

Moniliformin actually causes

competitive inhibition Competitive inhibition is interruption of a chemistry, chemical pathway owing to one chemical substance inhibiting the effect of another by competing with it for molecular binding, binding or chemical bond, bonding. Any metabolism, metabolic or c ...

of the activity of pyruvate dehydrogenase complex of respiratory reaction, which prevents

pyruvic acid Pyruvic acid (CH3COCOOH) is the simplest of the keto acids, alpha-keto acids, with a carboxylic acid and a ketone functional group. Pyruvate, the conjugate acid, conjugate base, CH3COCOO−, is an metabolic intermediate, intermediate in several m ...

, product of

glycolysis Glycolysis is the metabolic pathway that converts glucose () into pyruvic acid, pyruvate and, in most organisms, occurs in the liquid part of cells (the cytosol). The Thermodynamic free energy, free energy released in this process is used to form ...

, to convert to

acetyl-CoA Acetyl-CoA (acetyl coenzyme A) is a molecule that participates in many biochemical reactions in protein, carbohydrate and lipid metabolism. Its main function is to deliver the acetyl group to the citric acid cycle (Krebs cycle) to be oxidation, o ...

. Ultrastructural examination of right ventricular wall of 9 month old female

mink Mink are dark-colored, semiaquatic, carnivorous mammals of the genera ''Neogale'' and '' Mustela'' and part of the family Mustelidae, which also includes weasels, otters, and ferrets. There are two extant species referred to as "mink": the A ...

('' Mustela vison'') fed acute doses of moniliformin (2.2 and 2.8 mg/kg diet) and sub-acute doses (1.5 to 3.2 mg/kg diet) reveals significant damage to myofiber,

mitochondria A mitochondrion () is an organelle found in the cells of most eukaryotes, such as animals, plants and fungi. Mitochondria have a double membrane structure and use aerobic respiration to generate adenosine triphosphate (ATP), which is us ...

, Z and M lines and

sarcoplasmic reticulum The sarcoplasmic reticulum (SR) is a membrane-bound structure found within muscle cells that is similar to the smooth endoplasmic reticulum in other cells. The main function of the SR is to store calcium ions (Ca2+). Calcium ion levels are kep ...

as well as increased

extracellular This glossary of biology terms is a list of definitions of fundamental terms and concepts used in biology, the study of life and of living organisms. It is intended as introductory material for novices; for more specific and technical definitions ...

collagen Collagen () is the main structural protein in the extracellular matrix of the connective tissues of many animals. It is the most abundant protein in mammals, making up 25% to 35% of protein content. Amino acids are bound together to form a trip ...

deposition. Minks are considered most sensitive mammals to the toxicity of moniliformin.Morgan MK, Fitzgerald SD, Rottinghaus GE, Bursian SJ and Aulerich RJ. 1999. Toxic effects to mink of moniliformin extracted from ''Fusarium fujikuroi'' culture material. ''Veterinary and Human Toxicology'' 1(1):pp-1-5 Chemically speaking, it is the

sodium salt Sodium salts are salt (chemistry), salts composed of a sodium cation and any anion. The anion may be the conjugate base of some Inorganic compound, inorganic or organic acids, or any monatomic or polyatomic anion. They can be formed by the Neutra ...

of deoxy

(the other name of that acid is semisquaric acid).

Physicochemical information

Moniliformin is soluble in water and polar solvents, such as

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

. λ_max: 226 nm and 259 nm in methanol.

Sources and references

{{reflist Mycotoxins Organic sodium salts Cyclobutenes Respiratory toxins Enols Ketones Organic acids

Biochemistry

Physicochemical information

See also

Sources and references