Application of the Crystalline Sponge Method to Revise the Structure of the Phenalenone Fuliginone.
The structure of fuliginone was revised from a phenyl substituted phenalenone to a hydroxyl substituted phenalenone as a result of its re-purification via HPLC with subsequent NMR analysis together with an independent synthesis and analysis of the crystal structure, which was secured via the crystalline sponge method. On-flow High Performance Liquid Chromatography coupled to Nuclear Magnetic Resonance spectroscopy (HPLC-NMR) was employed to confirm the presence of the natural product in the plant extract and to monitor for any possible degradation or conversion of the compound.
School of Science (Applied Chemistry and Environmental Science), RMIT University, GPO Box 2476, Melbourne, Victoria 3001, Australia. robert.brkljaca@rmit.edu.au.
Robert
R
Brkljača
Max-Planck-Institute for Chemical Ecology, Beutenberg Campus, Hans-Knöll-Str. 8, D-07745 Jena, Germany. schneider@ice.mpg.de.
Bernd
B
Schneider
Max-Planck-Institute for Chemical Ecology, Beutenberg Campus, Hans-Knöll-Str. 8, D-07745 Jena, Germany. williamhidalgob@hotmail.com.
William
W
Hidalgo
Instituto de Química, Síntesis y Biosíntesis de Metabolitos Naturales, Universidad de Antioquia, AA 1226, Medellín, Colombia. arafron@hotmail.com.
Felipe
F
Otálvaro
Instituto de Química, Síntesis y Biosíntesis de Metabolitos Naturales, Universidad de Antioquia, AA 1226, Medellín, Colombia. arafron@hotmail.com.
Felipe
F
Ospina
Department of Applied Chemistry, School of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan.
Shoukou
S
Lee
Department of Applied Chemistry, School of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan.
Manabu
M
Hoshino
Department of Applied Chemistry, School of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan.
Makoto
M
Fujita
School of Science (Applied Chemistry and Environmental Science), RMIT University, GPO Box 2476, Melbourne, Victoria 3001, Australia. sylvia.urban@rmit.edu.au.
Sylvia
S
Urban
D001688:Biological Products / Q000737:chemistry / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D043803:Phenalenes / Q000737:chemistry* / Q000302:isolation & purification*; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification
D001688:Biological Products; D043803:Phenalenes; D010936:Plant Extracts; C038036:phenalen-1-one
fuliginone;  HPLC‐NMR;  crystalline sponge method;  phenylphenalenone;  synthesis