Ustilagic acid

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Ustilagic acid is an organic compound with the formula C36H64O18. [1] The acid is a cellobiose lipid produced by the corn smut fungus Ustilago maydis under conditions of nitrogen starvation. [2] The acid was discovered in 1950 and was proved to be an amphipathic glycolipid with surface active properties. [3] [4] The name comes from Latin ustus which means burnt and refers to the scorched appearance of the smut fungi.

Contents

Uses

Cellobiose lipids are known as biosurfactants 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 and Cryptococcus (Filobasidiella) neoformans. The antifungal activity manifested at acidic pH. [5]

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Basidiomycota is one of two large divisions that, together with the Ascomycota, constitute the subkingdom Dikarya within the kingdom Fungi. Members are known as basidiomycetes. More specifically, Basidiomycota includes these groups: agarics, puffballs, stinkhorns, bracket fungi, other polypores, jelly fungi, boletes, chanterelles, earth stars, smuts, bunts, rusts, mirror yeasts, and Cryptococcus, the human pathogenic yeast. Basidiomycota are filamentous fungi composed of hyphae and reproduce sexually via the formation of specialized club-shaped end cells called basidia that normally bear external meiospores. These specialized spores are called basidiospores. However, some Basidiomycota are obligate asexual reproducers. Basidiomycota that reproduce asexually can typically be recognized as members of this division by gross similarity to others, by the formation of a distinctive anatomical feature, cell wall components, and definitively by phylogenetic molecular analysis of DNA sequence data.

<span class="mw-page-title-main">Corn smut</span> Fungal plant disease on maize and teosint

Corn smut is a plant disease caused by the pathogenic fungus Ustilago maydis. One of several cereal crop pathogens called smut, the fungus forms galls on all above-ground parts of corn species such as maize and teosinte. The infected corn is edible: in Mexico, it is considered a delicacy called huitlacoche, often eaten as a filling in quesadillas and other tortilla-based foods, as well as in soups.

<i>Cryptococcus</i> Genus of fungi

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<span class="mw-page-title-main">Glycolipid</span> Class of chemical compounds

Glycolipids are lipids with a carbohydrate attached by a glycosidic (covalent) bond. Their role is to maintain the stability of the cell membrane and to facilitate cellular recognition, which is crucial to the immune response and in the connections that allow cells to connect to one another to form tissues. Glycolipids are found on the surface of all eukaryotic cell membranes, where they extend from the phospholipid bilayer into the extracellular environment.

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The smuts are multicellular fungi characterized by their large numbers of teliospores. The smuts get their name from a Germanic word for dirt because of their dark, thick-walled, and dust-like teliospores. They are mostly Ustilaginomycetes and comprise seven of the 15 orders of the subphylum. Most described smuts belong to two orders, Ustilaginales and Tilletiales. The smuts are normally grouped with the other basidiomycetes because of their commonalities concerning sexual reproduction.

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<span class="mw-page-title-main">Ustilaginomycotina</span> Subdivision of fungi

The Ustilaginomycotina is a subdivision within the division Basidiomycota of the kingdom Fungi. It consists of the classes Ustilaginomycetes and Exobasidiomycetes, and in 2014 the subdivision was reclassified and the two additional classes Malasseziomycetes and Monilielliomycetes added. The name was first published by Doweld in 2001; Bauer and colleagues later published it in 2006 as an isonym. Ustilagomycotina and Agaricomycotina are considered to be sister groups, and they are in turn sister groups to the subdivision Pucciniomycotina.

Sporisorium reilianum Langdon & Full., (1978), previously known as Sphacelotheca reiliana, and Sporisorium reilianum, is a species of biotrophic fungus in the family Ustilaginaceae. It is a plant pathogen that infects maize and sorghum.

<span class="mw-page-title-main">Dimorphic fungus</span>

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<span class="mw-page-title-main">Fungus</span> Biological kingdom, separate from plants and animals

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<span class="mw-page-title-main">Ustilaginaceae</span> Family of fungi

The Ustilaginaceae are a family of smut fungi in the order Ustilaginomycetes. Collectively, the family contains 17 genera and 607 species.

<span class="mw-page-title-main">Killer toxin Kp4 family</span>

In molecular biology, the killer toxin Kp4 family is a family of killer toxins, which includes the Kp4 killer toxin from the smut fungus Ustilago maydis.

<i>Ustilago esculenta</i> Species of fungus

Ustilago esculenta is a species of fungus in the Ustilaginaceae, a family of smut fungi. It is in the same genus as the fungi that cause corn smut, loose smut of barley, false loose smut, covered smut of barley, loose smut of oats, and other grass diseases. This species is pathogenic as well, attacking Manchurian wild rice, also known as Manchurian ricegrass, Asian wild rice, and wateroat. This grass is its only known host.

<span class="mw-page-title-main">Ferrichrome A</span> Chemical compound

Ferrichrome A is a siderophore in the ferrichrome family. Iron is an essential element for the survival and proliferation of organisms. Microorganisms produce and secrete potent iron chelators, also known as siderophores, to aid in the sequestration and increase bioavailability of iron. Since the discovery of ferrichrome in 1952, the ferrichrome family of siderophores contains at least 20 structurally distinct members of cyclic hexapeptides that chelate ferric iron via an octahedral coordination geometry through the oxygen atoms of the hydroxyl and the acyl groups of the three ornithine residues. Ferrichrome A was found as one of the two siderophores produced by the biotrophic basidiomycete Ustilago maydis during its saprotrophic growth phase. U. maydis is the causative agent of corn smut.

Regine Kahmann is a German microbiologist and was Director at the Max Planck Institute for Terrestrial Microbiology in Marburg from 2000 to 2019. She was made a Foreign Member of the Royal Society (ForMRS) in 2020.

<span class="mw-page-title-main">Reginald Haskins</span> Canadian biologist (1916–1999)

Reginald H. Haskins was a Canadian mycologist. Born in North Bay, Ontario, Haskins trained as a botanist, specializing in mycology, receiving his master's degree from the University of Western Ontario and his doctorate degree from Harvard University in 1949. He lived with his wife and three children in Saskatoon, Canada.

<i>Moesziomyces</i> Genus of fungi

Moesziomyces is a fungal genus in the family Ustilaginaceae.

References

  1. Senning, Alexander (2006). Elsevier's Dictionary of Chemoetymology: The Whys and Whences of Chemical Nomenclature and Terminology. Elsevier. p. 410. ISBN   9780080488813 . Retrieved 31 October 2016.
  2. Juárez-Montiel M, Ruiloba de León S, Chávez-Camarillo G, Hernández-Rodríguez C, Villa-Tanaca L (2011). "Huitlacoche (corn smut), caused by the phytopathogenic fungus Ustilago maydis, as a functional food". Rev Iberoam Micol. 28 (2): 69–73. doi:10.1016/j.riam.2011.01.001. PMID   21352944.
  3. "Glycosides of fatty acids with a O-glycosyl link and an ester link". cyberlipid.org. Retrieved 28 November 2016.
  4. "Induced production of the novel glycolipid ustilagic acid C in the plant pathogen Ustilago maydis". July 2013. Retrieved 28 November 2016.
  5. Kulakovskaya, TV; Shashkov, AS; Kulakovskaya, EV; Golubev, WI (2005). "Ustilagic acid secretion by Pseudozyma fusiformata strains". FEMS Yeast Res. 5 (10): 919–23. doi: 10.1016/j.femsyr.2005.04.006 . PMID   15972266.