Planta Med 2016; 82(S 01): S1-S381
DOI: 10.1055/s-0036-1596660
Abstracts
Georg Thieme Verlag KG Stuttgart · New York

Investigation of optimal methods including pH-zone-refining centrifugal partition chromatography for the isolation of communesins from cultures of a marine-derived Penicillium expansum

TTP Hoang
1   University of Nantes, EA 2160 – Mer Molécules Santé, 9 rue Bias BP 53508, 44035 Nantes-cedex 1 France
,
N Borie
3   UMR CNRS 7312, Université de Reims Champagne-Ardenne, Bât. 18, Moulin de la Housse, BP 1039, 51687 Reims, Cedex 2, France
,
A Gratia
3   UMR CNRS 7312, Université de Reims Champagne-Ardenne, Bât. 18, Moulin de la Housse, BP 1039, 51687 Reims, Cedex 2, France
,
YF Pouchus
1   University of Nantes, EA 2160 – Mer Molécules Santé, 9 rue Bias BP 53508, 44035 Nantes-cedex 1 France
,
C Roullier
1   University of Nantes, EA 2160 – Mer Molécules Santé, 9 rue Bias BP 53508, 44035 Nantes-cedex 1 France
2   Corsaire-ThalassOMICS Metabolomics Facility, Biogenouest, University of Nantes, France
,
JH Renault
3   UMR CNRS 7312, Université de Reims Champagne-Ardenne, Bât. 18, Moulin de la Housse, BP 1039, 51687 Reims, Cedex 2, France
,
O Grovel
1   University of Nantes, EA 2160 – Mer Molécules Santé, 9 rue Bias BP 53508, 44035 Nantes-cedex 1 France
2   Corsaire-ThalassOMICS Metabolomics Facility, Biogenouest, University of Nantes, France
› Author Affiliations
Further Information

Publication History

Publication Date:
14 December 2016 (online)

 
 

    Communesins are a rare family of indole alkaloids isolated from marine or terrestrial fungal strains [1]. To date, eleven communesins (A-K) have been described, which share a common and unique heptacyclic core with the presence of two vicinal quaternary centres [2]. Recently, 10 new analogs have been detected by HPLC-HRMS/MS as trace-amounts in cultures of a P. expansum marine-derived strain [3]. Very few biological data have been described for this class of compounds, but an interesting activity on the cellular cytoskeleton has been once described, making them a putative new class of microfilament disrupting drugs [4]. In this context, our laboratory has engaged a program for the investigation of communesin chemodiversity and structure-activity relationships. The aim of this study was: 1- to obtain the major compounds communesin A and B in sufficient quantities for their pharmacological evaluation, and 2- to investigate the use of pH-zone-refining Centrifugal Partition Chromatography (CPC) for the isolation of minor communesin analogs. Different methods of extraction and purification were then tested and the composition of the fractions obtained was established by UHPLC-ESI-MS/MS. This led to the development of an optimized protocol including a solvent culture extraction followed by an indole alkaloid concentration at pH 1, allowing the selective recovery of communesins with a yield of 98%. 70 mg and 52 mg of communesin A and B respectively were then obtained as pure compounds. The alkaloidic fraction was subsequently fractionated by pH-zone-refining CPC in ascending mode using a biphasic solvent system composed of methyl tert-butyl ether/acetonitrile/water (4/1/5, v/v/v). The separation of more than ten communesins was then performed, which were further purified. Then, pH-zone refining CPC was shown to be an efficient separation tool for fungal alkaloids isolation, which will allow to reveal the structural diversity of this unique class of complex natural products.

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    Acknowledgements: Authors acknowledge the Vietnam International Education Development program for a PhD grant for Thuy T.P. Hoang.

    Keywords: Communesin, Penicillium expansum, centrifugal partition chromatography (CPC).

    References:

    [1] Zuo Z, Ma D. Synthetic studies toward communesins. Isr J Chem 2011; 51: 434 – 441

    [2] Seo JH, Artman GD, Weinreb SM. Synthetic studies on perphoramidine and the communesins: Construction of the Vicinal Quaternary Stereocenters. J Org Chem 2006; 71: 8891 – 8900

    [3] Kerzaon I, Pouchus YF, Monteau F, Le Bizec B, Nourrisson MR, Biard JF and Grovel O. Structural investigation and elucidation of new communesins from a marine-derived Penicillium expansum Link by liquid chromatography/electrospray ionization mass spectrometry. Rapid Commun Mass Spectrom 2009; 23: 3928 – 3938

    [4] Ratnayake AS, Yoshida WY, Moobery SL, Hemscheidt TK. J Org Chem 2001, 66, 8717 (b) Retraction of this article: Ratnayake AS, Yoshida WY, Mooberry SL, Hemscheidt TK. J Org Chem 2003; 68: 1640


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    No conflict of interest has been declared by the author(s).

     
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