TY - JOUR
T1 - Production of phenylacetic acid derivatives and 4-epiradicinol in culture by Curvularia lunata
AU - Varma, Gouri B.
AU - Fatope, Majekodunmi O.
AU - Marwah, Ruchi G.
AU - Deadman, Mike E.
AU - Al-Rawahi, Fathiya K.
PY - 2006/9
Y1 - 2006/9
N2 - 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.
AB - 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.
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U2 - 10.1016/j.phytochem.2006.05.032
DO - 10.1016/j.phytochem.2006.05.032
M3 - Article
C2 - 16884750
AN - SCOPUS:33748649682
SN - 0031-9422
VL - 67
SP - 1925
EP - 1930
JO - Phytochemistry
JF - Phytochemistry
IS - 17
ER -