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Identification of Phenanthrene Derivatives in Aerides rosea (Orchidaceae) Using the Combined Systems HPLC–ESI–HRMS/MS and HPLC–DAD–MS–SPE–UV–NMR
Author(s) -
Cakova Veronika,
Urbain Aurélie,
Antheaume Cyril,
Rimlinger Nicole,
Wehrung Patrick,
Bonté Frédéric,
Lobstein Annelise
Publication year - 2014
Publication title -
phytochemical analysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.574
H-Index - 72
eISSN - 1099-1565
pISSN - 0958-0344
DOI - 10.1002/pca.2533
Subject(s) - chemistry , high performance liquid chromatography , chromatography , phenanthrene , tandem mass spectrometry , orchidaceae , mass spectrometry , organic chemistry , botany , biology
In our continued efforts to contribute to the general knowledge on the chemical diversity of orchids, we have decided to focus our investigations on the Aeridinae subtribe. Following our previous phytochemical study of Vanda coerulea , which has led to the identification of phenanthrene derivatives, a closely related species, Aerides rosea Lodd. ex Lindl. & Paxton, was chosen for investigation. Objective To identify new secondary metabolites, and to avoid isolation of those already known, by means of the combined systems HPLC–DAD(diode‐array detector) with high‐resolution tandem mass spectrometry (HRMS/MS) and HPLC–DAD–MS–SPE(solid‐phase extraction)–UV–NMR. Methods A dereplication strategy was developed using a HPLC–DAD–HRMS/MS targeted method and applied to fractions from A. rosea stem extract. Characterisation of unknown minor compounds was then performed using the combined HPLC–DAD–MS–SPE–UV–NMR system. Results The dereplication method allowed the characterisation of four compounds (gigantol, imbricatin, methoxycoelonin and coelonin), previously isolated from Vanda coerulea stem extract. The analyses of two fractions permitted the identification of five additional minor constituents including one phenanthropyran, two phenanthrene and two dihydrophenanthrene derivatives. The full set of NMR data of each compound was obtained from microgram quantities. Conclusion Nine secondary metabolites were characterised in A. rosea stems, utilising HPLC systems combined with high‐resolution analytical systems. Two of them are newly described phenanthrene derivatives: aerosanthrene (5‐methoxyphenanthrene‐2,3,7‐triol) and aerosin (3‐methoxy‐9,10‐dihydro‐2,5,7‐phenanthrenetriol). Copyright © 2014 John Wiley & Sons, Ltd.