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Molecules 2014, 19(9), 15042-15057; doi:10.3390/molecules190915042

Rapid Identification of Coumarins from Micromelum falcatum by UPLC-HRMS/MS and Targeted Isolation of Three New Derivatives

1
Laboratory of Pharmacognosy & Natural Products Chemistry, Faculty of Pharmacy, University of Athens, Panepistimioupoli, Zografou, 15771 Athens, Greece
2
Joint Laboratory of Phytochemistry, University of Health Sciences, 73 Bd Monivong, Phnom Penh 12203, Cambodia
3
School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, Quai Ernest-Ansermet 30, CH-1211 Geneva 4, Switzerland
*
Author to whom correspondence should be addressed.
Received: 13 July 2014 / Revised: 8 September 2014 / Accepted: 9 September 2014 / Published: 19 September 2014
(This article belongs to the Section Natural Products)
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Abstract

Micromelum falcatum, a medicinal plant of the Rutaceae family, has been used in the Traditional Chinese Medicine (TCM) mainly against colds and rheumatoid arthritis. Despite its traditional use the association of its constituents with possible anti-inflammatory activity has not been explored. During this study, a rapid UPLC-ESI(+)-HRMS method was developed for the profiling of M. falcatum leave extracts and the targeted isolation of coumarin constituents. Based on chromatographic, spectroscopic and spectrometric features several 7-oxygenated coumarin derivatives were detected. After targeted isolation, eight coumarins, among them three new natural products, namely microfalcrin, microcoumaririn and micromelosidester, were purified using semi-preparative HPLC and unambiguously identified by 1 and 2D NMR. Furthermore, important spectrometric characteristics were revealed based on the HRMS and HRMS/MS spectra of the isolated 7-oxygenated coumarins facilitating their identification in complex mixtures. Finally, the anti-inflammatory properties of the extracts and representative compounds were evaluated by measuring the inhibition of the pro-inflammatory mediator NF-κB induction and nitric oxide (NO) production. View Full-Text
Keywords: Micromelum falcatum; Rutaceae; 7-oxygenated coumarins; LC-MS; LTQ-Orbitrap; microfalcrin; microcoumaririn; micromelosidester; anti-inflammatory activity; NF-κB; NO production Micromelum falcatum; Rutaceae; 7-oxygenated coumarins; LC-MS; LTQ-Orbitrap; microfalcrin; microcoumaririn; micromelosidester; anti-inflammatory activity; NF-κB; NO production
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MDPI and ACS Style

Kouloura, E.; Danika, E.; Kim, S.; Hoerlé, M.; Cuendet, M.; Halabalaki, M.; Skaltsounis, L.A. Rapid Identification of Coumarins from Micromelum falcatum by UPLC-HRMS/MS and Targeted Isolation of Three New Derivatives. Molecules 2014, 19, 15042-15057.

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