Isolation and structural elucidation of a new cyclohexenone compound from Lasiodiplodia theobromae

A new cyclohexenone compound was isolated as a mixture of enantiomers from a culture filtrate of Lasiodiplodia theobromae. The relative structure was determined to be 4,5-dihydroxy-3-methyl-cyclohex-2-enone on the basis of MS, 1 H-NMR, and 13 C-NMR spectroscopic analyses, including 2D-NMR experiment...

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Bibliographic Details
Published in:Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2009-08, Vol.73 (8), p.1890-1892
Main Authors: Kitaoka, N.(Hokkaido Univ., Sapporo (Japan)), Nabeta, K, Matsuura, H
Format: Article
Language:English
Subjects:
ACIDE JASMONIQUE
ACIDO JASMONICO
ALMACENAMIENTO DE ALIMENTOS
Ascomycota - chemistry
Biological and medical sciences
BIOLOGICAL CONTAMINATION
BOTRYODIPLODIA THEOBROMAE
Chromatography, High Pressure Liquid
CONTAMINACION BIOLOGICA
CONTAMINATION BIOLOGIQUE
CULTURE MEDIA
Cyclohexanones - chemistry
Cyclohexanones - isolation & purification
Cyclohexanones - pharmacology
ESPECTROSCOPIA RMN
FOOD STORAGE
Fundamental and applied biological sciences. Psychology
JASMONIC ACID
Lasiodiplodia theobromae
Magnetic Resonance Spectroscopy
Mass Spectrometry
MEDIO DE CULTIVO
MILIEU DE CULTURE
Nicotiana - drug effects
Nicotiana - growth & development
NICOTIANA TABACUM
NMR SPECTROSCOPY
Seedlings - drug effects
Seedlings - growth & development
SPECTROSCOPIE RMN
Stereoisomerism
STOCKAGE DES ALIMENTS
theobroxide
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Summary:A new cyclohexenone compound was isolated as a mixture of enantiomers from a culture filtrate of Lasiodiplodia theobromae. The relative structure was determined to be 4,5-dihydroxy-3-methyl-cyclohex-2-enone on the basis of MS, 1 H-NMR, and 13 C-NMR spectroscopic analyses, including 2D-NMR experiments. Resolution of the enantiomers was conducted by a coupling reaction with (S)-MTPA-Cl followed by HPLC separation.
ISSN:0916-8451
1347-6947
DOI:10.1271/bbb.90218