Rhodotorulic acid

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Rhodotorulic acid
Rhodotorulic acid.svg
Names
IUPAC name
N-[3-[5-[3-[Acetyl(hydroxy)amino]propyl]-3,6-dioxopiperazin-2-yl]propyl]-N-hydroxyacetamide
Identifiers
3D model (JSmol)
ChEBI
ECHA InfoCard 100.038.786 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • CC(=O)N(CCCC1C(=O)NC(C(=O)N1)CCCN(C(=O)C)O)O
Properties
C14H24N4O6
Molar mass 344.368 g·mol−1
Density 1.277 g/cm3
0.96 g/cm3 (25 °C) @ pH 7 (water)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Rhodotorulic acid is the smallest of the 2,5-diketopiperazine family [1] of hydroxamate siderophores which are high-affinity chelating agents for ferric iron, produced by bacterial and fungal phytopathogens for scavenging iron from the environment. [2] It is a tetradentate ligand, meaning it binds one iron atom in four locations (two hydroxamate and two lactam moieties), and forms Fe2(siderophore)3 complexes to fulfill an octahedral coordination for iron. [3]

Rhodotorulic acid occurs in basidiomycetous yeasts [4] and was found to retard the spore germination of the fungus Botrytis cinerea . In combination with yeast Rhodotorula glutinis it was found to be effective in the biocontrol [5] of iprodione-resistant B. cinerea of apple wounds caused by the disease.

Related Research Articles

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<span class="mw-page-title-main">Ethylenediaminetetraacetic acid</span> Chemical compound

Ethylenediaminetetraacetic acid (EDTA), also called EDTA acid after its own abbreviation, is an aminopolycarboxylic acid with the formula [CH2N(CH2CO2H)2]2. This white, water-insoluble solid is widely used to bind to iron (Fe2+/Fe3+) and calcium ions (Ca2+), forming water-soluble complexes even at neutral pH. It is thus used to dissolve Fe- and Ca-containing scale as well as to deliver iron ions under conditions where its oxides are insoluble. EDTA is available as several salts, notably disodium EDTA, sodium calcium edetate, and tetrasodium EDTA, but these all function similarly.

<i>Botrytis cinerea</i> Species of fungus

Botrytis cinerea is a necrotrophic fungus that affects many plant species, although its most notable hosts may be wine grapes. In viticulture, it is commonly known as "botrytis bunch rot"; in horticulture, it is usually called "grey mould" or "gray mold".

<span class="mw-page-title-main">Siderophore</span> Iron compounds secreted by microorganisms

Siderophores (Greek: "iron carrier") are small, high-affinity iron-chelating compounds that are secreted by microorganisms such as bacteria and fungi. They help the organism accumulate iron. Although a widening range of siderophore functions is now being appreciated, siderophores are among the strongest (highest affinity) Fe3+ binding agents known. Phytosiderophores are siderophores produced by plants.

<span class="mw-page-title-main">Cytochrome b</span> Membrane protein involved in the electron transport chain

Cytochrome b within both molecular and cell biology, is a protein found in the membranes of aerobic cells. In eukaryotic mitochondria and in aerobic prokaryotes, cytochrome b is a component of respiratory chain complex III — also known as the bc1 complex or ubiquinol-cytochrome c reductase. In plant chloroplasts and cyanobacteria, there is an homologous protein, cytochrome b6, a component of the plastoquinone-plastocyanin reductase, also known as the b6f complex. These complexes are involved in electron transport, the pumping of protons to create a proton-motive force (PMF). This proton gradient is used for the generation of ATP. These complexes play a vital role in cells.

<span class="mw-page-title-main">Hydroxamic acid</span> Organic compounds of the form –C(=O)N(OH)–

In organic chemistry, hydroxamic acids are a class of organic compounds having a general formula R−C(=O)−N(−OH)−R' bearing the functional group −C(=O)−N(−OH)−, where R and R' are typically organyl groups or hydrogen. They are amides wherein the nitrogen atom has a hydroxyl substituent. They are often used as metal chelators.

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

Enterobactin is a high affinity siderophore that acquires iron for microbial systems. It is primarily found in Gram-negative bacteria, such as Escherichia coli and Salmonella typhimurium.

<i>Aureobasidium pullulans</i> Species of fungus

Aureobasidium pullulans is a ubiquitous and generalistic black, yeast-like fungus that can be found in different environments. It is well known as a naturally occurring epiphyte or endophyte of a wide range of plant species without causing any symptoms of disease. A. pullulans has a high importance in biotechnology for the production of different enzymes, siderophores and pullulan. Furthermore, A. pullulans is used in biological control of plant diseases, especially storage diseases.

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

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<span class="mw-page-title-main">Ascorbate ferrireductase (transmembrane)</span> Class of enzymes

Ascorbate ferrireductase (transmembrane) (EC 1.16.5.1, cytochrome b561) is an enzyme with systematic name Fe(III):ascorbate oxidorectuctase (electron-translocating). This enzyme catalyses the following chemical reaction

2,5-Diketopiperazine is an organic compound with the formula (NHCH2C(O))2. The compound features a six-membered ring containing two amide groups at opposite positions in the ring. It was first compound containing a peptide bond to be characterized by X-ray crystallography in 1938. It is the parent of a large class of 2,5-Diketopiperazines (2,5-DKPs) with the formula (NHCH2(R)C(O))2 (R = H, CH3, etc.). They are ubiquitous peptide in nature. They are often found in fermentation broths and yeast cultures as well as embedded in larger more complex architectures in a variety of natural products as well as several drugs. In addition, they are often produced as degradation products of polypeptides, especially in processed foods and beverages. They have also been identified in the contents of comets.

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

A diketopiperazine (DKP), also known as a dioxopiperazine or piperazinedione, is a class of organic compounds related to piperazine but containing two amide linkages. DKP's are the smallest known class of cyclic peptide. Despite their name, they are not ketones, but amides. Three regioisomers are possible, differing in the locations of the carbonyl groups.

Previously classified under the species complex Aureobasidium pullulans, Aureobasidium subglaciale is a black yeast-like, extremophile, ascomycete fungus that is found in extreme cold habitats. The species was originally isolated from subglacial ice of arctic glaciers. The first isolate of this species was obtained from subglacial ice of the Norwegian island Spitsbergen, one of the coldest places inhabited by humans. of Genomic data collected from specimens in the Aureobasidium pullulans complex justified distinction of four different species

Siderocalin(Scn), lipocalin-2, NGAL, 24p3 is a mammalian lipocalin-type protein that can prevent iron acquisition by pathogenic bacteria by binding siderophores, which are iron-binding chelators made by microorganisms. Iron serves as a key nutrient in host-pathogen interactions, and pathogens can acquire iron from the host organism via synthesis and release siderophores such as enterobactin. Siderocalin is a part of the mammalian defence mechanism and acts as an antibacterial agent. Crystallographic studies of Scn demonstrated that it includes a calyx, a ligand-binding domain that is lined with polar cationic groups. Central to the siderophore/siderocalin recognition mechanism are hybrid electrostatic/cation-pi interactions. To evade the host defences, pathogens evolved to produce structurally varied siderophores that would not be recognized by siderocalin, allowing the bacteria to acquire iron.

<span class="mw-page-title-main">Beer chemistry</span> Brewery science and beer chemical composition

The chemical compounds in beer give it a distinctive taste, smell and appearance. The majority of compounds in beer come from the metabolic activities of plants and yeast and so are covered by the fields of biochemistry and organic chemistry. The main exception is that beer contains over 90% water and the mineral ions in the water (hardness) can have a significant effect upon the taste.

<span class="mw-page-title-main">Brevianamide F</span> Chemical compound

Brevianamide F , also known as cyclo-(L-Trp-L-Pro), belongs to a class of naturally occurring 2,5-diketopiperazines. It is the simplest member and the biosynthetic precursor of a large family of biologically active prenylated tryptophan-proline 2,5-diketopiperazines that are produced by the fungi A. fumigatus and Aspergillus sp. It has been isolated from the bacterium Streptomyces sp. strain TN58 and shown to possess activity against the Gram-positive bacteria S. aureus and Micrococcus luteus. It has also been isolated from Bacillus cereus associated with the entomopathogenic nematode Rhabditis (Oscheius) sp. and shown to have antifungal activity against T. rubrum, C. neoformans, and C. albicans, better than amphotericin B. Although the proline 2,5-diketopiperazines are the most abundant and structurally diverse 2,5-diketopiperazines found in food, cyclo(L-Trp-L-Pro) has only been found as a minor 2,5-diketopiperazine (8.2 ppm) in autolyzed yeast extract. Initially, cyclo(L-Trp-L-Pro) and its DL, LD, and DD isomers showed potential for use in the treatment of cardiovascular dysfunction, but they were later shown to be hepatotoxic.

<i>Rhodotorula glutinis</i> Species of fungus

Rhodotorula glutinis is the type species of the genus Rhodotorula, a basidiomycetous genus of pink yeasts which contains 370 species. Heterogeneity of the genus has made its classification difficult with five varieties having been recognized; however, as of 2011, all are considered to represent a single taxon. The fungus is a common colonist of animals, foods and environmental materials. It can cause opportunistic infections, notably blood infection in the setting of significant underlying disease. It has been used industrially in the production of carotenoid pigments and as a biocontrol agent for post-harvest spoilage diseases of fruits.

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

Folpet is the tradename for the organic compound with the formula C6H4(CO)2NSCCl3. It is a fungicide derived from phthalimide (C6H4(CO)2N-) and trichloromethylsulfenyl chloride. The compound is white although commercial samples can appear brownish. It is structurally related to Captan, which is also a trichloromethylsulfenyl-containing fungicide.

<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.

References

  1. Borthwick AD, Da Costa NC (2017). "2,5-Diketopiperazines in Food and Beverages: Taste and Bioactivity". Critical Reviews in Food Science and Nutrition. 57 (4): 718–742. doi:10.1080/10408398.2014.911142. PMID   25629623. S2CID   1334464.
  2. Hider RC, Kong X (May 2010). "Chemistry and biology of siderophores". Natural Product Reports. 27 (5): 637–657. doi:10.1039/B906679A. PMID   20376388.
  3. Butler, Alison (2007). Biological Inorganic Chemistry: Structure & Reactivity. pp. 151–156. ISBN   978-1891389436.
  4. Van der Helm D, Winkelmann G (February 1994). "Hydroxamates and Polycarboxylates as Ion Transport Agents (Siderophores)". In Winkelmann, G., Winge, D. (eds.). Metal ions in fungi. Vol. 11. New York: Marcel Dekker Inc. pp. 39–98. ISBN   0-8247-9172-X.
  5. Sansone G, Rezza I, Calvente V, Benuzzi D, de Tosetti MI (March 2005). "Control of Botrytis cinerea strains resistant to iprodione in apple with rhodotorulic acid and yeasts". Postharvest Biology and Technology. 35 (3): 245–251. doi:10.1016/j.postharvbio.2004.09.005.