Production of phenylacetic acid derivatives and 4-epiradicinol in culture by Curvularia lunata.
Phenylacetic acid derivatives, methyl 2-acetyl-3,5-dihydroxyphenylacetate (1) and methyl 2-acetyl-5-hydroxy-3-methoxyphenylacetate (3); curvulin or ethyl 2-acetyl-3,5-dihydroxyphenylacetate (4), a known metabolite of Curvularia siddiqui, and 4-epiradicinol (5) have been isolated from the culture mycelia of Curvularia lunata grown on YMG, a medium consisting of yeast, malt extract and glucose. Compounds 1, 3 and 4 lack antimicrobial and antioxidant activity, but 4-epiradicinol (5) inhibited the growth of Escherichia coli, Staphylococcus aureus, Salmonella choleraesuis and Bacillus subtilis. The structures of compounds 1, 3-5 were determined by analyses of IR, MS, 1D and 2D NMR data, assisted by chemical shift comparison to related and model compounds. The relative stereochemistry of the vicinal diol in 5 was determined from the 1H NMR signals for the methyl protons of the resulting cyclic acetonide prepared from 5.
Varma
Gouri B
GB
Department of Chemistry, College of Science, Sultan Qaboos University, Al-Khod, Muscat, Oman.
Fatope
Majekodunmi O
MO
Marwah
Ruchi G
RG
Deadman
Mike E
ME
Al-Rawahi
Fathiya K
FK
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D001203:Ascomycota / Q000254:growth & development / Q000378:metabolism*; D001412:Bacillus subtilis / Q000187:drug effects; D017077:Culture Media, Conditioned / Q000737:chemistry / Q000494:pharmacology; D004926:Escherichia coli / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008826:Microbial Sensitivity Tests / Q000379:methods; D015394:Molecular Structure; D010648:Phenylacetates / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects
D000900:Anti-Bacterial Agents; D017077:Culture Media, Conditioned; D010648:Phenylacetates; C515896:methyl 2-acetyl-3,5-dihydroxyphenylacetate; C515895:methyl 2-acetyl-5-hydroxy-3-methoxyphenylacetate; C025136:phenylacetic acid