BIOCHEMISTRY OF THE USTILAGINALES: XI. METABOLIC PRODUCTS OF <i>USTILAGO ZEAE</i> IN SUBMERGED CULTURE

Haskins, R. H.; Thorn, J. A.; Boothroyd, B.

doi:10.1139/m55-089

Cited by 84 publications

(42 citation statements)

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“…produced (3S)-hexylitaconic acid (5). 4,12) Itaconic acid has been found as a metabolite of filamentous fungi such as Aspergillus itaconicus, 13) Helicobasidium mompa, 14) Ustilago zeae, 15) and U. maydis 16) and some yeast belonging to the genus Candida. 17) Whilst alkylated derivatives (alkylitaconic acids) have been isolated from lichens and several fungi.…”

Section: Resultsmentioning

confidence: 99%

Oxygenated Hexylitaconates from a Marine Sponge-Derived Fungus Penicillium sp.

Zhang

Lee

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Although dicarboxylic acids do not occur in appreciable amount as components of animal or vegetal lipids, generally they are important metabolic products of fatty acids. Especially the a,b-dicarboxylic acid and its derivatives, such as itaconic acid 1,2) and citraconic acid derivatives, 3) have been of much interest for their biosynthesis, stereochemistry, and chemical relationship. Furthermore, some of them were reported to exhibit various interesting bioactivities, such as plant growth-stimulation, 4) production of a cellulolytic active oxygen species, inhibition of the iron redox reaction, 5) inhibition of p53-HDM2 interaction which can induce apoptosis in human cancer cells, 6) and anti-trypanosomal activity. 7)In the course of search for bioactive metabolites from marine organisms, five hexylitaconic acid derivatives including four new ones (1-4) were isolated from a sponge-derived fungus Penicillium sp. Herein we describe the structure elucidation and the biological evaluation of the compounds. Results and DiscussionAccurate mass measurement (high resolution (HR)-FAB-MS) of compound 1 (m/z 259.1549 [MϩH] ϩ , Dϩ0.4 mmu) revealed the molecular formula to be C 13 H 22 O 5 with three degrees of unsaturation. Thirteen carbon signals were evident in the 13 C-NMR spectrum (Table 1) and deduced to be three methyl, five methylene, two methine, and three quaternary carbons from the distortionless enhancement by polarization transfer (DEPT)135 spectrum. According to 1 H-and In the course of our search for bioactive metabolites from marine organisms, new hexylitaconic acid derivatives (1-4), along with (3S)-hexylitaconic acid (5), were isolated from a sponge-derived fungus Penicillium sp. Based on the NMR and MS data, the structures of compounds 1-4 were defined as a a,b b-dicarboxylic acid derivatives, such as hexylitaconic acid and tensyuic acids which were previously reported as metabolite of Aspergillus niger, Penicillium striatisporum, or Apiospora montagnei. The isolated compounds were evaluated for cytotoxicity against a panel of five human solid tumor cell lines, and for anti-inflammatory activity gauged by their inhibitory effects on the production of major pro-inflammatory mediators (nitric oxide (NO), interleukin (IL)-6, tumor necrosis factor (TNF)-a a, and IL-1b b) in murine macrophage cells. Compounds 1 and 4 showed weak inhibition of IL-1b b production at the concentration of 200 m mM.

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Section: Resultsmentioning

confidence: 99%

Oxygenated Hexylitaconates from a Marine Sponge-Derived Fungus Penicillium sp.

Zhang

Lee

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…In principle these alterations could occur at the level of GDPmannose; however, MEL-producing U. maydis cells contain significant amounts of water-soluble mannose erythritol (19). Thus, we assume that Emt1 directly transfers mannose to the C-4 atom of meso-erythritol.…”

Section: Discussionmentioning

confidence: 99%

“…Sophorose lipids are secreted by Candida bombicola (21), mannosylerythritol lipids (MEL) were first isolated in the dimorphic fungus Ustilago maydis as extracellular oil with a higher density than water (19) and were later detected also in Candida antarctica, Schizonella melanogramma, and Geotrichum candidum (11,24,27). The primary structure of these glycolipids has been determined (6,13,16,27).…”

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confidence: 99%

Genetic Analysis of Biosurfactant Production inUstilago maydis

Hewald

Josephs

Bölker

2005

Appl Environ Microbiol

133

124

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The dimorphic basidiomycete Ustilago maydis produces large amounts of surface-active compounds under conditions of nitrogen starvation. These biosurfactants consist of derivatives of two classes of amphipathic glycolipids. Ustilagic acids are cellobiose lipids in which the disaccharide is O-glycosidically linked to 15,16-dihydroxyhexadecanoic acid. Ustilipids are mannosylerythritol lipids derived from acylated ␤-D-mannopyranosyl-D-erythritol. Whereas the chemical structure of these biosurfactants has been determined, the genetic basis for their biosynthesis and regulation is largely unknown. Here we report the first identification of two genes, emt1 and cyp1, that are essential for the production of fungal extracellular glycolipids. emt1 is required for mannosylerythritol lipid production and codes for a protein with similarity to prokaryotic glycosyltransferases involved in the biosynthesis of macrolide antibiotics. We suggest that Emt1 catalyzes the synthesis of mannosyl-D-erythritol by transfer of GDP-mannose. Deletion of the gene cyp1 resulted in complete loss of ustilagic acid production. Cyp1 encodes a cytochrome P450 monooxygenase which is highly related to a family of plant fatty acid hydroxylases. Therefore we assume that Cyp1 is directly involved in the biosynthesis of the unusual 15,16-dihydroxyhexadecanoic acid. We could show that mannosylerythritol lipid production is responsible for hemolytic activity on blood agar, whereas ustilagic acid secretion is required for long-range pheromone recognition. The mutants described here allow for the first time a genetic analysis of glycolipid production in fungi.

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“…To date, several other natural producers of itaconic acid were identified, such as Aspergillus terreus (12), Ustilago zeae (38), and Ustilago maydis and the yeast Candida sp. (93).…”

Section: The Beginning Of Itaconic Acid Productionmentioning

confidence: 99%

Itaconic Acid: The Surprising Role of an Industrial Compound as a Mammalian Antimicrobial Metabolite

2015

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Itaconic acid is well known as a precursor for polymer synthesis and has been involved in industrial processes for decades. In a recent surprising discovery, itaconic acid was found to play a role as an immune-supportive metabolite in mammalian immune cells, where it is synthesized as an antimicrobial compound from the citric acid cycle intermediate cis-aconitic acid. Although the immune-responsive gene 1 protein (IRG1) has been associated to immune response without a mechanistic function, the critical link to itaconic acid production through an enzymatic function of this protein was only recently revealed. In this review, we highlight the history of itaconic acid as an industrial and antimicrobial compound, starting with its biotechnological synthesis and ending with its antimicrobial function in mammalian immune cells. 12.1

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BIOCHEMISTRY OF THE USTILAGINALES: XI. METABOLIC PRODUCTS OF USTILAGO ZEAE IN SUBMERGED CULTURE

Cited by 84 publications

References 0 publications

Oxygenated Hexylitaconates from a Marine Sponge-Derived Fungus Penicillium sp.

Oxygenated Hexylitaconates from a Marine Sponge-Derived Fungus Penicillium sp.

Genetic Analysis of Biosurfactant Production inUstilago maydis

Itaconic Acid: The Surprising Role of an Industrial Compound as a Mammalian Antimicrobial Metabolite

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