Planta Med 2016; 82(11/12): 1051-1057
DOI: 10.1055/s-0042-108207
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Preparative Scale MS-Guided Isolation of Bioactive Compounds Using High-Resolution Flash Chromatography: Antifungals from Chiloscyphus polyanthos as a Case Study[*]

Antonio Azzollini**
1  School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, Geneva, Switzerland
,
Quentin Favre-Godal**
1  School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, Geneva, Switzerland
,
Jiaozhen Zhang
2  Department of Natural Products Chemistry, Key Lab of Chemical Biology of the Ministry of Education, School of Pharmaceutical Sciences, Shandong University, Jinan, Peopleʼs Republic of China
,
Laurence Marcourt
1  School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, Geneva, Switzerland
,
Samad Nejad Ebrahimi
3  Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, Tehran, Iran
,
Shuqi Wang
2  Department of Natural Products Chemistry, Key Lab of Chemical Biology of the Ministry of Education, School of Pharmaceutical Sciences, Shandong University, Jinan, Peopleʼs Republic of China
,
Peihong Fan
2  Department of Natural Products Chemistry, Key Lab of Chemical Biology of the Ministry of Education, School of Pharmaceutical Sciences, Shandong University, Jinan, Peopleʼs Republic of China
,
Hongxiang Lou
2  Department of Natural Products Chemistry, Key Lab of Chemical Biology of the Ministry of Education, School of Pharmaceutical Sciences, Shandong University, Jinan, Peopleʼs Republic of China
,
Davy Guillarme
1  School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, Geneva, Switzerland
,
Emerson Ferreira Queiroz
1  School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, Geneva, Switzerland
,
Jean-Luc Wolfender
1  School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, Geneva, Switzerland
› Author Affiliations
Further Information

Publication History

received 10 March 2016
revised 23 April 2016

accepted 28 April 2016

Publication Date:
23 June 2016 (eFirst)

Abstract

In natural product research, the efficient purification of molecules from large amounts of complex extracts is a key element. In this regard, an integrative strategy for efficient MS-guided isolation of antifungal compounds has been developed. First, off-line HPLC antifungal activity-based profiling and HPLC-PDA-MS profiling were used to localize the compounds of interest on the analytical scale. Then, the analytical gradient was geometrically transferred to the flash chromatographic level. Finally, an MS-triggered isolation of the localized bioactive molecules was realized using high-resolution flash chromatographic columns (15 µm spherical particles) coupled to a single quadrupole mass spectrometer via a splitter system. This isolation strategy was applied for the MS-targeted purification of antifungal principles from the liverwort Chiloscyphus polyanthos. This rational methodology has high potential for the targeted large-scale purification of bioactive compounds, avoiding the need to repeat a given bioassay at each isolation step. Seven sesquiterpene lactones were isolated, of which five were found to be bioactive and one was reported as a new compound. The absolute configuration of some compounds was established for the first time by electronic circular dichroism spectroscopy.

* Dedicated to Professor Kurt Hostettmann in recognition of his outstanding contribution to natural product research.


** Equally contributing first authors.


Supporting Information