Ustilagic acid is an organic compound with the formula C₃₆H₆₄O₁₈. The acid is a cellobiose

lipid Lipids are a broad group of naturally-occurring molecules which includes fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids includ ...

produced by the corn smut fungus ''

Ustilago maydis Corn smut is a plant disease caused by the pathogenic fungus ''Ustilago maydis'' that causes smut on maize and teosinte. The fungus forms galls on all above-ground parts of corn species. It is edible, and is known in Mexico as the delicacy ' ...

'' under conditions of nitrogen starvation. The acid was discovered in 1950 and was proved to be an amphipathic glycolipid with surface active properties. The name comes from Latin ''ustus'' which means ''burnt'' and refers to the scorched appearance of the smut fungi.

Uses

Cellobiose lipids are known as

biosurfactant Biosurfactant usually refers to surfactants of microbial origin. Most of the biosurfactants produced by microbes are synthesized extracellularly and many microbes are known to produce biosurfactants in large relative quantities. Some are of commerc ...

s and natural detergents. They can be used in pharmaceutical, cosmetic, and food applications and are known for their strong fungicidal activity on many species. The yeast Pseudozyma fusiformata and Pseudozyma graminicola secrete ustilagic acids, 2-O-3-hydroxyhexanoyl-beta-D-glucopyranosyl-(1→4)-6-O-acetyl-beta-D-glucopyranosyl-(1→16)-2,15,16- trihydroxyhexadecanoic acid. Similar compounds are the extracellular cellobiose lipids of the yeasts Cryptococcus humicola and Trichosporon porosum : 2,3,4-O-triacetyl-beta-D-glucopyranosyl-(1→4)-6-O-acetyl-beta-D-glucopyranosyl -(1→16)-2,16-dihydroxyhexadecanoic acid. These compounds inhibit the growth of quite a number of various species of yeast and fungi, including

Candida albicans ''Candida albicans'' is an opportunistic pathogenic yeast that is a common member of the human gut flora. It can also survive outside the human body. It is detected in the gastrointestinal tract and mouth in 40–60% of healthy adults. It is usu ...

and

Cryptococcus ''Cryptococcus'' is a genus of fungi in the family Cryptococcaceae that includes both yeasts and filamentous species. The filamentous, sexual forms or teleomorphs were formerly classified in the genus ''Filobasidiella'', while ''Cryptococcus'' ...

(Filobasidiella) neoformans. The antifungal activity manifested at acidic pH.

References

External links

* {{Fatty acids Fatty acids