Rhodotorulic acid

Last updated
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
ChEMBL
ChemSpider
ECHA InfoCard 100.038.786 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 242-681-9
PubChem CID
UNII
  • InChI=1S/C14H24N4O6/c1-9(19)17(23)7-3-5-11-13(21)16-12(14(22)15-11)6-4-8-18(24)10(2)20/h11-12,23-24H,3-8H2,1-2H3,(H,15,22)(H,16,21)
    Key: PUWVNTVQJFSBDH-UHFFFAOYSA-N
  • 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.

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.
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