NCBI Taxonomy: 5269

Ustilago (ncbi_taxid: 5269)

found 36 associated metabolites at genus taxonomy rank level.

Ancestor: Ustilaginaceae

Child Taxonomies: Ustilago maydis, Ustilago nuda, Ustilago levis, Ustilago jagei, Ustilago curta, Ustilago milii, Ustilago cynodontis, Ustilago coicis, Ustilago sparti, Ustilago vinosa, Ustilago avenae, Ustilago sparsa, Ustilago brizae, Ustilago porosa, Ustilago hordei, Ustilago scaura, Ustilago sphaerogena, Ustilago affinis, Ustilago grandis, Ustilago tragana, Ustilago bromina, Ustilago altilis, Ustilago davisii, Ustilago lituana, Ustilago crameri, Ustilago bullata, Ustilago tritici, Ustilago salveii, Ustilago cruenta, Ustilago kummeri, Ustilago serpens, Ustilago ixophori, Ustilago alcornii, Ustilago phrygica, Ustilago echinata, Ustilago pamirica, Ustilago esculenta, Ustilago bromivora, Ustilago siamensis, Ustilago quitensis, Ustilago comburens, Ustilago chloridis, Ustilago shiraiana, Ustilago loliicola, Ustilago inaltilis, Ustilago perennans, Ustilago filiformis, Ustilago nunavutica, Ustilago bouriqueti, Ustilago phragmitis, Ustilago planetella, Ustilago vetiveriae, Ustilago xerochloae, Ustilago longissima, Ustilago neyraudiae, Ustilago corcontica, Ustilago schmidtiae, Ustilago spinificis, Ustilago trichophora, Ustilago turcomanica, Ustilago striiformis, Ustilago abaconensis, Ustilago shanxiensis, Ustilago sieglingiae, Ustilago neocopinata, Ustilago aeluropodis, Ustilago aff. sorghi, Ustilago denotarisii, Ustilago syntherismae, Ustilago kamerunensis, unclassified Ustilago, Ustilago scrobiculata, Ustilago schroeteriana, Ustilago alopecurivora, Ustilago aff. bromivora, Ustilago austro-africana, Ustilago calamagrostidis, Ustilago drakensbergiana, Ustilago panici-gracilis, Ustilago aff. filiformis, Ustilago sporoboli-indici, Ustilago aff. vanderystii, Ustilago aff. andropogonis, Ustilago aff. syntherismae, Ustilago airae-caespitosae, Ustilago aff. schroeteriana, Ustilago aff. dactyloctaenii, Ustilago agrostidis-palustris, Ustilago bromivora x Ustilago hordei

Obtusifoliol

(3S,4S,5S,10S,13R,14R,17R)-4,10,13,14-Tetramethyl-17-((R)-6-methyl-5-methyleneheptan-2-yl)-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

C30H50O (426.3861)


Obtusifoliol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, obtusifoliol is considered to be a sterol lipid molecule. Obtusifoliol is found, on average, in the highest concentration within evening primroses. Obtusifoliol has also been detected, but not quantified in, several different foods, such as common chokecherries, jicama, pepper (C. frutescens), avocado, and pecan nuts. This could make obtusifoliol a potential biomarker for the consumption of these foods. Obtusifoliol is an intermediate in the biosynthesis of cholesterol: in a reaction catalyzed by the enzyme CYP51A1 (EC 1.14.13.70, sterol 14-demethylase) (PMID: 9559662). CYP51A1 is a housekeeping enzyme essential for the viability of mammals, an essential step in cholesterol biosynthesis. Sterol 14-demethylation occurs in all organisms exhibiting de novo sterol biosynthesis and CYP51A1 has been conserved throughout evolution (PMID: 8797093). Obtusifoliol is an intermediate in the biosynthesis of cholesterol, in a reaction catalyzed by the enzyme CYP51A1 (EC 1.14.13.70, sterol 14-demethylase). (PMID: 9559662); CYP51A1 is a housekeeping enzyme essential for viability of mammals, essential step in cholesterol biosynthesis; sterol 14-demethylation occurs in all organism exhibiting de novo sterol biosynthesis, and CYP51A1 has been conserved throughout evolution. (PMID: 8797093). Obtusifoliol is found in many foods, some of which are jews ear, mamey sapote, star fruit, and tinda. Obtusifoliol is a natural product found in Euphorbia chamaesyce, Euphorbia nicaeensis, and other organisms with data available. Obtusifoliol is a specific CYP51 inhibitor, Obtusifoliol shows the affinity with Kd values of 1.2 μM and 1.4 μM for Trypanosoma brucei (TB) and human CYP51, respectively[1]. Obtusifoliol is a specific CYP51 inhibitor, Obtusifoliol shows the affinity with Kd values of 1.2 μM and 1.4 μM for Trypanosoma brucei (TB) and human CYP51, respectively[1].

   

Itaconic acid

2-Hydroxy-3-naphthoyl-2-naphthylamine

C5H6O4 (130.0266)


Itaconic acid is a dicarboxylic acid that is methacrylic acid in which one of the methyl hydrogens is substituted by a carboxylic acid group. It has a role as a fungal metabolite and a human metabolite. It is a dicarboxylic acid and an olefinic compound. It derives from a succinic acid. It is a conjugate acid of an itaconate(2-). This dicarboxylic acid is a white solid that is soluble in water, ethanol, and acetone. Historically, itaconic acid was obtained by the distillation of citric acid, but currently it is produced by fermentation. The name itaconic acid was devised as an anagram of aconitic acid, another derivative of citric acid. Itaconic acid, also known as itaconate, belongs to the class of organic compounds known as branched fatty acids. These are fatty acids containing a branched chain. Itaconic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Since the 1960s, it is produced industrially by the fermentation of carbohydrates such as glucose or molasses using fungi such as Aspergillus itaconicus or Aspergillus terreus. For A. terreus the itaconate pathway is mostly elucidated. The generally accepted route for itaconate is via glycolysis, tricarboxylic acid cycle, and a decarboxylation of cis-aconitate to itaconate via cis-aconitate-decarboxylase. The smut fungus Ustilago maydis uses an alternative route. Cis-aconitate is converted to the thermodynamically favoured trans-aconitate via aconitate-Δ-isomerase (Adi1). trans-Aconitate is further decarboxylated to itaconate by trans-aconitate-decarboxylase (Tad1). Itaconic acid is also produced in cells of macrophage lineage. It was shown that itaconate is a covalent inhibitor of the enzyme isocitrate lyase in vitro. As such, itaconate may possess antibacterial activities against bacteria expressing isocitrate lyase (such as Salmonella enterica and Mycobacterium tuberculosis). It is also sythesized in the laboratory, where dry distillation of citric acid affords itaconic anhydride, which undergoes hydrolysis to itaconic acid. Itaconic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=97-65-4 (retrieved 2024-07-01) (CAS RN: 97-65-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Itaconic acid, a precursor of polymers, chemicals, and fuels, can be synthesized by many fungi. Itaconic acid also is a macrophage-specific metabolite. Itaconic acid mediates crosstalk between macrophage metabolism and peritoneal tumors[1][2].

   

2-Hydroxyparaconate

2-Hydroxyparaconate

C5H6O5 (146.0215)


   

6-Methoxy-2(3H)-benzoxazolone

6-methoxy-2,3-dihydro-1,3-benzoxazol-2-one

C8H7NO3 (165.0426)


6-methoxy-2-benzoxazolinone is a 2-benzoxazolinone that is substituted by a methoxy group at position 6. It has a role as a plant metabolite, a muscle relaxant, an anticonvulsant, an antibacterial agent and an antifungal agent. It is a benzoxazole and an aromatic ether. It is functionally related to a 2-benzoxazolinone. Coixol is a natural product found in Scoparia dulcis, Oceanapia, and other organisms with data available. Isolated from roots of Coix lacryma jobi (Jobs tears) and from seedlings of wheat, corn and rye. 6-Methoxy-2(3H)-benzoxazolone is found in many foods, some of which are cereals and cereal products, corn, alcoholic beverages, and coffee and coffee products. 6-Methoxy-2(3H)-benzoxazolone is found in alcoholic beverages. 6-Methoxy-2(3H)-benzoxazolone is isolated from roots of Coix lacryma jobi (Jobs tears) and from seedlings of wheat, corn and rye. Coixol (6-Methoxy-2-benzoxazolinone;6-MBOA) is a polyphenol extracted from coix (Coix lachryma-jobi?L.var.ma-yuen?Stapf) with antimicrobial and antitumor activities[1]. Coixol (6-Methoxy-2-benzoxazolinone;6-MBOA) is a polyphenol extracted from coix (Coix lachryma-jobi?L.var.ma-yuen?Stapf) with antimicrobial and antitumor activities[1].

   
   

2-Hydroxy-2-(hydroxymethyl)butanedioic acid

2-Hydroxy-2-(hydroxymethyl)butanedioic acid

C5H8O6 (164.0321)


   

Itaconic acid

2-methylidenebutanedioic acid;2-methylenesuccinic acid

C5H6O4 (130.0266)


A dicarboxylic acid that is methacrylic acid in which one of the methyl hydrogens is substituted by a carboxylic acid group. Itaconic acid, a precursor of polymers, chemicals, and fuels, can be synthesized by many fungi. Itaconic acid also is a macrophage-specific metabolite. Itaconic acid mediates crosstalk between macrophage metabolism and peritoneal tumors[1][2].

   

Coixol

2(3H)-Benzoxazolone, 6-methoxy- (9CI)

C8H7NO3 (165.0426)


Coixol (6-Methoxy-2-benzoxazolinone;6-MBOA) is a polyphenol extracted from coix (Coix lachryma-jobi?L.var.ma-yuen?Stapf) with antimicrobial and antitumor activities[1]. Coixol (6-Methoxy-2-benzoxazolinone;6-MBOA) is a polyphenol extracted from coix (Coix lachryma-jobi?L.var.ma-yuen?Stapf) with antimicrobial and antitumor activities[1].

   

3-(acetyloxy)-2-(hydroxymethyl)-5-[(2-methylpropanoyl)oxy]-6-(2,3,4-trihydroxybutoxy)oxan-4-yl hexadecanoate

3-(acetyloxy)-2-(hydroxymethyl)-5-[(2-methylpropanoyl)oxy]-6-(2,3,4-trihydroxybutoxy)oxan-4-yl hexadecanoate

C32H58O12 (634.3928)


   

(2r)-2-hydroxy-2-(hydroxymethyl)butanedioic acid

(2r)-2-hydroxy-2-(hydroxymethyl)butanedioic acid

C5H8O6 (164.0321)


   

(1r,3ar,5as,7s,9as,11ar)-3a,9a,11a-trimethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol

(1r,3ar,5as,7s,9as,11ar)-3a,9a,11a-trimethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol

C29H48O (412.3705)


   

(2s,3s,4s)-3,6-dihydroxy-8-methoxy-2-methyl-5,10-dioxo-2h,3h,4h-naphtho[2,3-b]pyran-4-yl acetate

(2s,3s,4s)-3,6-dihydroxy-8-methoxy-2-methyl-5,10-dioxo-2h,3h,4h-naphtho[2,3-b]pyran-4-yl acetate

C17H16O8 (348.0845)


   

(3r)-3-hydroxy-5-oxooxolane-3-carboxylic acid

(3r)-3-hydroxy-5-oxooxolane-3-carboxylic acid

C5H6O5 (146.0215)


   

(2r,3r,4s,5s,6r)-3-(acetyloxy)-2-(hydroxymethyl)-5-[(2-methylpropanoyl)oxy]-6-[(2r,3s)-2,3,4-trihydroxybutoxy]oxan-4-yl hexadecanoate

(2r,3r,4s,5s,6r)-3-(acetyloxy)-2-(hydroxymethyl)-5-[(2-methylpropanoyl)oxy]-6-[(2r,3s)-2,3,4-trihydroxybutoxy]oxan-4-yl hexadecanoate

C32H58O12 (634.3928)


   

(1r,3as,3bs,5as,9ar,9bs,11ar)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-7,7-dimethoxy-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthren-5-one

(1r,3as,3bs,5as,9ar,9bs,11ar)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-7,7-dimethoxy-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthren-5-one

C30H52O3 (460.3916)


   

(2r,3r,4s,5s,6r)-3,5-bis(acetyloxy)-2-[(acetyloxy)methyl]-6-[(2r,3s)-2,3,4-trihydroxybutoxy]oxan-4-yl hexadecanoate

(2r,3r,4s,5s,6r)-3,5-bis(acetyloxy)-2-[(acetyloxy)methyl]-6-[(2r,3s)-2,3,4-trihydroxybutoxy]oxan-4-yl hexadecanoate

C32H56O13 (648.3721)


   

3-(acetyloxy)-2-[(acetyloxy)methyl]-5-(butanoyloxy)-6-(2,3,4-trihydroxybutoxy)oxan-4-yl hexadecanoate

3-(acetyloxy)-2-[(acetyloxy)methyl]-5-(butanoyloxy)-6-(2,3,4-trihydroxybutoxy)oxan-4-yl hexadecanoate

C34H60O13 (676.4034)


   

2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(1h-indol-3-yl)ethoxy]oxane-3,4,5-triol

2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(1h-indol-3-yl)ethoxy]oxane-3,4,5-triol

C21H29NO10 (455.1791)


   

(2r,3r,4s,5s,6r)-3-(acetyloxy)-2-[(acetyloxy)methyl]-5-(hexanoyloxy)-6-[(2r,3s)-2,3,4-trihydroxybutoxy]oxan-4-yl hexadecanoate

(2r,3r,4s,5s,6r)-3-(acetyloxy)-2-[(acetyloxy)methyl]-5-(hexanoyloxy)-6-[(2r,3s)-2,3,4-trihydroxybutoxy]oxan-4-yl hexadecanoate

C36H64O13 (704.4347)


   

methyl 2-[2-formyl-5-(hydroxymethyl)pyrrol-1-yl]propanoate

methyl 2-[2-formyl-5-(hydroxymethyl)pyrrol-1-yl]propanoate

C10H13NO4 (211.0845)


   

(2r,3r,4s,5s,6r)-3-(acetyloxy)-2-[(acetyloxy)methyl]-5-(butanoyloxy)-6-[(2r,3s)-2,3,4-trihydroxybutoxy]oxan-4-yl hexadecanoate

(2r,3r,4s,5s,6r)-3-(acetyloxy)-2-[(acetyloxy)methyl]-5-(butanoyloxy)-6-[(2r,3s)-2,3,4-trihydroxybutoxy]oxan-4-yl hexadecanoate

C34H60O13 (676.4034)


   

3-(acetyloxy)-2-[(acetyloxy)methyl]-5-(hexanoyloxy)-6-(2,3,4-trihydroxybutoxy)oxan-4-yl hexadecanoate

3-(acetyloxy)-2-[(acetyloxy)methyl]-5-(hexanoyloxy)-6-(2,3,4-trihydroxybutoxy)oxan-4-yl hexadecanoate

C36H64O13 (704.4347)


   

6-methoxy-1,3-benzoxazol-2-ol

6-methoxy-1,3-benzoxazol-2-ol

C8H7NO3 (165.0426)


   

1-(5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-5,7-dione

1-(5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-5,7-dione

C28H46O2 (414.3498)


   

3a,9a,11a-trimethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol

3a,9a,11a-trimethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol

C29H48O (412.3705)


   

(1r,3as,3bs,5as,9ar,9bs,11ar)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-5,7-dione

(1r,3as,3bs,5as,9ar,9bs,11ar)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-5,7-dione

C28H46O2 (414.3498)


   

(2r,3s,4s,5r,6s)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(4-ethenyl-2-methoxyphenoxy)oxane-3,4,5-triol

(2r,3s,4s,5r,6s)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(4-ethenyl-2-methoxyphenoxy)oxane-3,4,5-triol

C20H28O11 (444.1632)


   

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 9-hydroxy-3-methyldec-2-enoate

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 9-hydroxy-3-methyldec-2-enoate

C17H30O8 (362.1941)


   

1-(5,6-dimethylheptan-2-yl)-7,7-dimethoxy-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthren-5-one

1-(5,6-dimethylheptan-2-yl)-7,7-dimethoxy-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthren-5-one

C30H52O3 (460.3916)


   

3,5-bis(acetyloxy)-2-[(acetyloxy)methyl]-6-(2,3,4-trihydroxybutoxy)oxan-4-yl hexadecanoate

3,5-bis(acetyloxy)-2-[(acetyloxy)methyl]-6-(2,3,4-trihydroxybutoxy)oxan-4-yl hexadecanoate

C32H56O13 (648.3721)


   

16-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-2,15-dihydroxyhexadecanoic acid

16-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-2,15-dihydroxyhexadecanoic acid

C24H44O11 (508.2883)


   

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2z)-9-hydroxy-3-methyldec-2-enoate

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2z)-9-hydroxy-3-methyldec-2-enoate

C17H30O8 (362.1941)


   

16-({6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-2,15-dihydroxyhexadecanoic acid

16-({6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-2,15-dihydroxyhexadecanoic acid

C24H44O11 (508.2883)


   

(2r,3s,4s,5r,6r)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(1h-indol-3-yl)ethoxy]oxane-3,4,5-triol

(2r,3s,4s,5r,6r)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(1h-indol-3-yl)ethoxy]oxane-3,4,5-triol

C21H29NO10 (455.1791)


   

2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(4-ethenyl-2-methoxyphenoxy)oxane-3,4,5-triol

2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(4-ethenyl-2-methoxyphenoxy)oxane-3,4,5-triol

C20H28O11 (444.1632)


   

3-hydroxy-5-oxooxolane-3-carboxylic acid

3-hydroxy-5-oxooxolane-3-carboxylic acid

C5H6O5 (146.0215)