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Article

Application of the Crystalline Sponge Method to Revise the Structure of the Phenalenone Fuliginone

by
Robert Brkljača
1,
Bernd Schneider
2,
William Hidalgo
2,
Felipe Otálvaro
3,
Felipe Ospina
3,
Shoukou Lee
4,
Manabu Hoshino
4,
Makoto Fujita
4 and
Sylvia Urban
1,*
1
School of Science (Applied Chemistry and Environmental Science), RMIT University, GPO Box 2476, Melbourne, Victoria 3001, Australia
2
Max‐Planck‐Institute for Chemical Ecology, Beutenberg Campus, Hans‐Knöll‐Str. 8, D‐07745 Jena, Germany
3
Instituto de Química, Síntesis y Biosíntesis de Metabolitos Naturales, Universidad de Antioquia, AA 1226, Medellín, Colombia
4
Department of Applied Chemistry, School of Engineering, The University of Tokyo, Hongo, Bunkyo‐ku, Tokyo, 113‐8656, Japan
*
Author to whom correspondence should be addressed.
Molecules 2017, 22(2), 211; https://doi.org/10.3390/molecules22020211
Submission received: 13 December 2016 / Accepted: 25 January 2017 / Published: 30 January 2017
(This article belongs to the Special Issue New Methodologies in Natural Product Analytics and Structure Elucidation)
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Abstract

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.
Keywords: fuliginone; phenylphenalenone; synthesis; crystalline sponge method; HPLC‐NMR fuliginone; phenylphenalenone; synthesis; crystalline sponge method; HPLC‐NMR
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MDPI and ACS Style

Brkljača, R.; Schneider, B.; Hidalgo, W.; Otálvaro, F.; Ospina, F.; Lee, S.; Hoshino, M.; Fujita, M.; Urban, S. Application of the Crystalline Sponge Method to Revise the Structure of the Phenalenone Fuliginone. Molecules 2017, 22, 211. https://doi.org/10.3390/molecules22020211

AMA Style

Brkljača R, Schneider B, Hidalgo W, Otálvaro F, Ospina F, Lee S, Hoshino M, Fujita M, Urban S. Application of the Crystalline Sponge Method to Revise the Structure of the Phenalenone Fuliginone. Molecules. 2017; 22(2):211. https://doi.org/10.3390/molecules22020211

Chicago/Turabian Style

Brkljača, Robert, Bernd Schneider, William Hidalgo, Felipe Otálvaro, Felipe Ospina, Shoukou Lee, Manabu Hoshino, Makoto Fujita, and Sylvia Urban. 2017. "Application of the Crystalline Sponge Method to Revise the Structure of the Phenalenone Fuliginone" Molecules 22, no. 2: 211. https://doi.org/10.3390/molecules22020211

APA Style

Brkljača, R., Schneider, B., Hidalgo, W., Otálvaro, F., Ospina, F., Lee, S., Hoshino, M., Fujita, M., & Urban, S. (2017). Application of the Crystalline Sponge Method to Revise the Structure of the Phenalenone Fuliginone. Molecules, 22(2), 211. https://doi.org/10.3390/molecules22020211

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