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

Molecules

Eirini Kouloura²  Eirini Danika²  Sothea Kim³  Mélanie Hoerlé¹  Muriel Cuendet¹  Maria Halabalaki² 

[1] School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, Quai Ernest-Ansermet 30, CH-1211 Geneva 4, Switzerland; E-Mails:;Laboratory of Pharmacognosy & Natural Products Chemistry, Faculty of Pharmacy, University of Athens, Panepistimioupoli, Zografou, 15771 Athens, Greece; E-Mails:;Joint Laboratory of Phytochemistry, University of Health Sciences, 73 Bd Monivong, Phnom Penh 12203, Cambodia; E-Mail:

关键词: Micromelum falcatum;    Rutaceae;    7-oxygenated coumarins;    LC-MS;    LTQ-Orbitrap;    microfalcrin;    microcoumaririn;    micromelosidester;    anti-inflammatory activity;    NF-κB;    NO production;   

DOI  :  10.3390/molecules190915042

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.