PMID- 23592386 OWN - NLM STAT- MEDLINE DCOM- 20140529 LR - 20131024 IS - 1099-1565 (Electronic) IS - 0958-0344 (Linking) VI - 24 IP - 6 DP - 2013 Nov-Dec TI - Analysis of Cleistopholis patens leaf and trunk bark oils using combined GC- flame ionisation detection, GC-retention index, GC-MS and (13) C-NMR. PG - 574-80 LID - 10.1002/pca.2435 [doi] AB - INTRODUCTION: Germacrenes A-C are secondary metabolites produced by various plants. They are sesquiterpene hydrocarbons bearing the (E,E)-1,5-cyclodecadiene structure known to undergo thermal rearrangement through a [3.3]-sigmatropic reaction. Such a rearrangement was evidenced by comparing the contents of a given germacrene and the corresponding elemene calculated by GC-flame ionisation detection (FID) with the relative intensities of the signals of both molecules in the (13) C-NMR spectrum of the mixture, recorded at room temperature. OBJECTIVE: To develop a protocol to identify and quantify germacrenes A, B and C and in parallel the corresponding elemenes, using a combination of GC-FID and (13) C-NMR and then provide a correct analysis of Cleistopholis patens essential oils. METHODS: The essential oil was submitted to GC-FID, GC-retention index, GC-MS and (13) C-NMR analyses. The relative percentages of every couple of germacrene and elemene measured by GC-FID were summed. Then, the relative ratio of the mean intensities of the signals of the protonated carbons of a given germacrene and the corresponding elemene was calculated. The contents of both compounds were obtained by combining GC-FID and (13) C-NMR data. RESULTS: The true content of germacrene A/beta-elemene, germacrene B/gamma-elemene and germacrene C/delta-elemene in leaf and root oils from C. patens was evaluated by combination of GC-FID and (13) C-NMR data. Correct analysis of the essential oils was provided. CONCLUSION: Combined analysis of essential oil including (13) C-NMR without isolation of the components, appeared really efficient to identify and quantify germacrene isomers and in parallel elemene isomers in essential oils. CI - Copyright (c) 2013 John Wiley & Sons, Ltd. FAU - Ouattara, Zana A AU - Ouattara ZA AD - Universite de Corse-CNRS, UMR 6134 SPE, Equipe Chimie et Biomasse, Route des Sanguinaires, 20000, Ajaccio, France; Laboratoire de Chimie Organique Biologique, UFR-SSMT, Universite Felix Houphouet-Boigny, BPV 34, Abidjan, Cote d'Ivoire. FAU - Boti, Jean Brice AU - Boti JB FAU - Ahibo, Antoine Coffy AU - Ahibo AC FAU - Casanova, Joseph AU - Casanova J FAU - Tomi, Felix AU - Tomi F FAU - Bighelli, Ange AU - Bighelli A LA - eng PT - Journal Article PT - Research Support, Non-U.S. Gov't DEP - 20130417 PL - England TA - Phytochem Anal JT - Phytochemical analysis : PCA JID - 9200492 RN - 0 (Plant Oils) RN - 0 (Sesquiterpenes, Germacrane) SB - IM MH - Annonaceae/*chemistry MH - Cote d'Ivoire MH - Gas Chromatography-Mass Spectrometry MH - Nuclear Magnetic Resonance, Biomolecular MH - Plant Bark/chemistry MH - Plant Leaves/chemistry MH - Plant Oils/*analysis MH - Sesquiterpenes, Germacrane/*analysis/chemistry OTO - NOTNLM OT - 13C-NMR OT - Cleistopholis patens OT - elemene OT - essential oil composition OT - germacrene EDAT- 2013/04/18 06:00 MHDA- 2014/05/30 06:00 CRDT- 2013/04/18 06:00 PHST- 2012/10/31 00:00 [received] PHST- 2013/02/13 00:00 [revised] PHST- 2013/02/19 00:00 [accepted] PHST- 2013/04/18 06:00 [entrez] PHST- 2013/04/18 06:00 [pubmed] PHST- 2014/05/30 06:00 [medline] AID - 10.1002/pca.2435 [doi] PST - ppublish SO - Phytochem Anal. 2013 Nov-Dec;24(6):574-80. doi: 10.1002/pca.2435. Epub 2013 Apr 17.