Production of phenylacetic acid derivatives and 4-epiradicinol in culture by Curvularia lunata

Gouri B. Varma, Majekodunmi O. Fatope, Ruchi G. Marwah, Mike E. Deadman, Fathiya K. Al-Rawahi

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1925-1930
Number of pages6
JournalPhytochemistry
Volume67
Issue number17
DOIs
Publication statusPublished - Sep 2006

Fingerprint

phenylacetic acid
Curvularia
glycols
malt extract
Mycelium
Salmonella enterica
stereochemistry
Bacillus subtilis
Salmonella
protons
mycelium
Staphylococcus aureus
Protons
Antioxidants
antioxidant activity
anti-infective agents
Yeasts
chemical derivatives
Nuclear magnetic resonance
metabolites

ASJC Scopus subject areas

  • Plant Science
  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery

Cite this

Production of phenylacetic acid derivatives and 4-epiradicinol in culture by Curvularia lunata. / Varma, Gouri B.; Fatope, Majekodunmi O.; Marwah, Ruchi G.; Deadman, Mike E.; Al-Rawahi, Fathiya K.

In: Phytochemistry, Vol. 67, No. 17, 09.2006, p. 1925-1930.

Research output: Contribution to journalArticle

Varma, Gouri B. ; Fatope, Majekodunmi O. ; Marwah, Ruchi G. ; Deadman, Mike E. ; Al-Rawahi, Fathiya K. / Production of phenylacetic acid derivatives and 4-epiradicinol in culture by Curvularia lunata. In: Phytochemistry. 2006 ; Vol. 67, No. 17. pp. 1925-1930.
@article{6acd0ffa0a21497aaaf7d1b87db48a1a,
title = "Production of phenylacetic acid derivatives and 4-epiradicinol in culture by Curvularia lunata",
abstract = "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.",
author = "Varma, {Gouri B.} and Fatope, {Majekodunmi O.} and Marwah, {Ruchi G.} and Deadman, {Mike E.} and Al-Rawahi, {Fathiya K.}",
year = "2006",
month = "9",
doi = "10.1016/j.phytochem.2006.05.032",
language = "English",
volume = "67",
pages = "1925--1930",
journal = "Phytochemistry",
issn = "0031-9422",
publisher = "Elsevier Limited",
number = "17",

}

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.

UR - http://www.scopus.com/inward/record.url?scp=33748649682&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33748649682&partnerID=8YFLogxK

U2 - 10.1016/j.phytochem.2006.05.032

DO - 10.1016/j.phytochem.2006.05.032

M3 - Article

VL - 67

SP - 1925

EP - 1930

JO - Phytochemistry

JF - Phytochemistry

SN - 0031-9422

IS - 17

ER -