Ustilagic acid

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Ustilagic acid

From Wikipedia, the free encyclopedia

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.

Uses

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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]

References

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^ 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.
^ 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.
^ "Glycosides of fatty acids with a O-glycosyl link and an ester link". cyberlipid.org. Retrieved 28 November 2016.
^ "Induced production of the novel glycolipid ustilagic acid C in the plant pathogen Ustilago maydis". July 2013. Retrieved 28 November 2016.
^ 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.

External links

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EVELEIGH, DOUGLAS E. (March 1964). "Fungal Metabolism of Complex Glycosides: Ustilagic Acid" (PDF). The Journal of Biological Chemistry. 239 (3): 839–44. doi:10.1016/S0021-9258(18)51666-5. PMID 14154463. Retrieved 28 November 2016.

v t e Lipids: fatty acids
Saturated	Propionic (C3) Butyric (C4) Valeric (C5) Caproic (C6) Enanthic (C7) Caprylic (C8) Pelargonic (C9) Capric (C10) Undecylic (C11) Lauric (C12) Tridecylic (C13) Myristic (C14) Pentadecylic (C15) Palmitic (C16) Margaric (C17) Stearic (C18) Nonadecylic (C19) Arachidic (C20) Heneicosylic (C21) Behenic (C22) Tricosylic (C23) Lignoceric (C24) Pentacosylic (C25) Cerotic (C26) Carboceric (C27) Montanic (C28) Nonacosylic (C29) Melissic (C30) Hentriacontylic (C31) Lacceroic (C32) Psyllic (C33) Geddic (C34) Ceroplastic (C35) Hexatriacontylic (C36) Heptatriacontanoic (C37) Octatriacontanoic (C38) Nonatriacontanoic (C39) Tetracontanoic (C40)
ω−3 Unsaturated	Octenoic (8:1) Decenoic (10:1) Decadienoic (10:2) Lauroleic (12:1) Laurolinoleic (12:2) Myristovaccenic (14:1) Myristolinoleic (14:2) Myristolinolenic (14:3) Palmitolinolenic (16:3) Palmitidonic (16:4) α-Linolenic (18:3) Stearidonic (18:4) α-Parinaric (18:4) Dihomo-α-linolenic (20:3) Eicosatetraenoic (20:4) Eicosapentaenoic (20:5) Clupanodonic (22:5) Docosahexaenoic (22:6) 9,12,15,18,21-Tetracosapentaenoic (24:5) 6,9,12,15,18,21-Tetracosahexaenoic (24:6)
ω−5 Unsaturated	Myristoleic (14:1) Palmitovaccenic (16:1) α-Eleostearic (18:3) β-Eleostearic (trans-18:3) Punicic (18:3) 7,10,13-Octadecatrienoic (18:3) 9,12,15-Eicosatrienoic (20:3) β-Eicosatetraenoic (20:4)
ω−6 Unsaturated	8-Tetradecenoic (14:1) 12-Octadecenoic (18:1) Linoleic (18:2) Linolelaidic (trans-18:2) γ-Linolenic (18:3) Calendic (18:3) Pinolenic (18:3) Dihomo-linoleic (20:2) Dihomo-γ-linolenic (20:3) Sciadonic (20:3) Arachidonic (20:4) Adrenic (22:4) Osbond (22:5)
ω−7 Unsaturated	Palmitoleic (16:1) Vaccenic (18:1) Rumenic (18:2) Paullinic (20:1) 7,10,13-Eicosatrienoic (20:3)
ω−9 Unsaturated	Oleic (18:1) Elaidic (trans-18:1) Gondoic (20:1) Erucic (22:1) Nervonic (24:1) 8,11-Eicosadienoic (20:2) Mead (20:3)
ω−10 Unsaturated	Sapienic (16:1)
ω−11 Unsaturated	Gadoleic (20:1)
ω−12 Unsaturated	4-Hexadecenoic (16:1) Petroselinic (18:1) 8-Eicosenoic (20:1)

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Category:

Fatty acids