Neohydroxyaspergillic acid

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Neohydroxyaspergillic acid
Category Antibiotics
Catalog number BBF-04494
CAS 72598-34-6
Molecular Weight 240.30
Molecular Formula C12H20N2O3
Purity ≥95%

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Description

Neohydroxyaspergillic acid is an antibiotic produced by Aspergillus sckrotiorum, which is active against some bacteriophages and fungus.

Specification

Synonyms NSC 613947; 2(1H)-Pyrazinone, 1-hydroxy-6-[(1S)-1-hydroxy-2-methylpropyl]-3-(2-methylpropyl)-
Storage Store at -20°C
IUPAC Name 1-hydroxy-6-[(1S)-1-hydroxy-2-methylpropyl]-3-(2-methylpropyl)pyrazin-2-one
Canonical SMILES CC(C)CC1=NC=C(N(C1=O)O)C(C(C)C)O
InChI InChI=1S/C12H20N2O3/c1-7(2)5-9-12(16)14(17)10(6-13-9)11(15)8(3)4/h6-8,11,15,17H,5H2,1-4H3/t11-/m0/s1
InChI Key QTTAJMQGQJRLDK-NSHDSACASA-N

Properties

Appearance Light Yellow Needles
Antibiotic Activity Spectrum Fungi; Bacterial
Boiling Point 391.0±34.0°C (Predicted)
Melting Point 164-166°C
Density 1.19±0.1 g/cm3 (Predicted)
Solubility Soluble in Methanol, Ethanol

Reference Reading

1. Bioactive Metabolites from the Endophytic Fungus Aspergillus sp. SPH2
Elena Trujillo, Viridiana Morales-Sánchez, Carmen E Díaz, Rubén Muñoz, Sonia A Olmeda, María Fe Andrés, Azucena González-Coloma, Felix Valcarcel J Fungi (Basel) . 2021 Feb 2;7(2):109. doi: 10.3390/jof7020109.
In the current study, an ethyl acetate extract from the endophytic fungusAspergillussp. SPH2 isolated from the stem parts of the endemic plantBethencourtia palmensiswas screened for its biocontrol properties against plant pathogens (Fusarium moniliforme,Alternaria alternata,andBotrytis cinerea), insect pests (Spodoptera littoralis,Myzus persicae,Rhopalosiphum padi), plant parasites (Meloidogyne javanica), and ticks (Hyalomma lusitanicum). SPH2 gave extracts with strong fungicidal and ixodicidal effects at different fermentation times. The bioguided isolation of these extracts gave compounds1-3. Mellein (1) showed strong ixodicidal effects and was also fungicidal. This is the first report on the ixodicidal effects of1. Neoaspergillic acid (2) showed potent antifungal effects. Compound2appeared during the exponential phase of the fungal growth while neohydroxyaspergillic acid (3) appeared during the stationary phase, suggesting that2is the biosynthetic precursor of3. The mycotoxin ochratoxin A was not detected under the fermentation conditions used in this work. Therefore, SPH2 could be a potential biotechnological tool for the production of ixodicidal extracts rich in mellein.

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