The composition of root bark oil from Cleistopholis glauca Pierre ex Engler & Diels growing wild in Ivory Coast was investigated by GC (in combination with retention indices) and 13C NMR spectroscopy after partition of hydrocarbons and oxygenated compounds on silica gel. Thirty-one compounds have been identified. C. glauca produces a sesquiterpene-rich oil, patchoulenone (33.5%), cyperene (9.5%) and germacrene D (6.6%) being the main components. Special attention was paid to the identification and quantification of germacrene C (a heat-sensitive compound) and δ-elemene, which were achieved by a combination of GC(FID) and 13C NMR spectroscopy. The composition of C. glauca root bark and leaf oils differed drastically.
Le ThomasA. (1969) Flore du Gabon, volume 16. Annonacées, Muséum National d'Histoire Naturelle, Paris.
2.
Ake AssiL., AbeyeJ., GuinkoS., GiguetR., BangavouY. (1981) Contribution à l'identification et au recensement des plantes utilisées dans la médecine traditionnelle et la pharmacopée en République Centrafricaine.Agence de Coopération Culturelle et Technique, Paris.
3.
TaneP., AyaforJ.F., SondengamB.L. (1988) Partially-acetylated dodecanyl tri- and tetra-rhamnoside derivatives from Cleistopholis glauca (Annonaceae). Tetrahedron Letters, 29, 1837–1840.
4.
SeidelV., BailleulF., WatermanP.G. (2000) Novel oligorhamnosides from the stem bark of Cleistopholis glauca. Journal of Natural Products, 63, 6–11.
5.
NgiefuK., PaquotC., VieuxA. (1976) Les plantes à huile du Zaïre II. Oleagineux, 31, 545–547.
6.
EtseJ.T., GrayA.I., WatermanP.G. (1988) Chemistry in the Annonaceae XXV: Sesquiterpenes from the stem bark of Cleistopholis glauca. Journal of Natural Products, 51, 314–318.
7.
OuattaraZ.A., BotiJ.B., AhiboC.A., TomiF., CasanovaJ., BighelliA. (2012) Chemical composition of the leaf oil of Cleistopholis glauca Pierre ex Engler & Diels from Côte d'Ivoire. Journal of Essential Oil Research, 24, 471–474.
8.
TomiF., BradesiP., BighelliA., CasanovaJ. (1995) Computer-aided identification on individual components of essential oils using carbon-13 NMR spectroscopy. Journal of Magnetic Resonance Analysis, 1, 25–34.
9.
TomiF., CasanovaJ. (2006) 13C-NMR as a tool for identification of individual components of essential oils from Labiatae. A review. Acta Horticulturae, 723, 185–192.
OuattaraZ.A., BotiJ.B., AhiboA.C., CasanovaJ., TomiF., BighelliA. (2013) Analysis of Cleistopholis patens leaf and trunk bark oils using combined GC-flame ionisation detection, GC-retention index, GC-MS and 13C-NMR. Phytochemical Analysis, in press. DOI: 10.1002/pca.2435
12.
TrivediB., MotlO., HeroutV., SormF. (1964) On terpenes CLXIV. Composition of the oil from Cyperus rotundus L. Structure of patchoulenone. Collection of Czechoslovak Chemical Communications, 29, 1675–1688
13.
HishamA., WrayV., PietersL., ClaeysM., DommisseR., VlietinckA. (1992) Complete 1H and 13C NMR spectral assignment of patchoulenone, a tricyclic sesquiterpene ketone. Magnetic Resonance in Chemistry, 30, 295–297.
14.
SeidelV., BailleulF., WatermanP.G. (1999) Partially acetylated tri- and tetrarhamnoside dodecanyl ether derivatives from Cleistopholis patens. Phytochemistry, 52, 465–472.
15.
MoriK., MoriH. (1987) Synthesis of both enantiomers of juvenile hormone III. Tetrahedron, 43, 4097–4106
16.
BlayG., GarciaB., MolinaE., PedroJ.R. (2007) Synthesis of (+)-pechueloic acid and (+)-aciphyllene. Revision of the structure of (+)-aciphyllene. Tetrahedron, 63, 9621–9626.
17.
YapiT.A., BotiJ.B., AhiboA.C., BighelliA., CasanovaJ., TomiF. (2013) Combined analysis of Xylopia rubescens Oliv. leaf oil by GC-FID, GC-MS and 13C NMR: Structure elucidation of new compounds. Flavour Fragrance Journal, 28, 373–379.
18.
JoulainD., KönigW.A. (1998) The Atlas of Spectral Data of Sesquiterpene Hydrocarbons.E.B.-Verlag, Hamburg.
19.
ColbyS.M., CrockJ., Dowdle-RizzoB., LemauxP.G., CroteauR. (1998) Germacrene C synthase from Lycopersicon esculentum cv. VFNT Cherry tomato: cDNA isolation, characterization, and bacterial expression of the multiple product sesquiterpene cyclase. Biochemistry Proceedings of National Academy of Sciences USA, 95, 2216–2221.
20.
AdioA.M. (2009) Germacrenes A-E and related compounds: thermal, photochemical and acid induced transannular cyclizations. Tetrahedron, 65, 1533–1552.
