,
Amenan Evelyne Tanoh,
Acafou Thierry Yapi,
Kidjegbo Augustin Toure,
Tomi Felix,
Zanahi Felix Tonzibo
It is well-known that geijerene is mostly associated with pregeijerene. These terpenes are believed to be thermoconvertible by a type of sigmatropic transposition order supra or antarafaciale. Our contribution to the study of the molecular pair consisted on a combination of statistical and analytical approach to the chemical composition of Chromolaena odorata essential oil. A compilation of chemical compositions of the samples obtained by steam distillation and analyzed by GC, presented a variation of this binomial proportions in different countries. For Ivory Coast, the results of analysis of 71 samples showed a dominance of geijerene proportion. We carried out a two-stage sampling by chemical variability factors (effects of site and period). We chose, at random, three different samples we submitted separately to chromatographic analysis (GC) and spectroscopic analysis (13C-NMR). It appears from this study that pregeijerene and geijerene were found in the essential oil with a relationship characterized by a polynomial degree 6 between these both molecules. Then during the chromatographic analysis, thermal conversion of pregeijerene into geijerene with the ratio 85.8% was observed. This result supported the idea of the coexistence of pregeijerene and geijerene in the essential oil of Chromolaena odorata. We intend to help clarify the kinetics and complete thermodynamics of this equilibrium.
| Published in | Science Journal of Chemistry (Volume 12, Issue 6) |
| DOI | 10.11648/j.sjc.20241206.14 |
| Page(s) | 144-152 |
| Creative Commons |
This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited. |
| Copyright |
Copyright © The Author(s), 2024. Published by Science Publishing Group |
Chromolaena Odorata, Essential Oil Composition, Statistical Approach, Thermal Conversion, Geijerene, Pregeijerene
| [1] | F. Avlessi, G. A. Alitonou, T. S. Djenontin, F. Tchobo, Yèhouénou., C. Menut and D. Sohounhloué. Chemical composition and biological activities of essential oil extracted from the fresh leaves of Chromolaena odorata (L. Robinson) growing in Benin. Journal of Biological Sciences. 2012, Vol. 1, pp. 7-13. |
| [2] | M. S. Owolabi, O. Akintayo, O. Y. Kamil, L. Labunmi, E. V. Heather, A. T. Jessika and N. S. William. Chemical composition and bioactivity of the essential oil of Chromolaena odorata from Nigeria. Rec. Nat. Prod. 2010, Vol. 4, pp. 72-78. |
| [3] | R. K. Joshi. Chemical composition of the essential oils of aerial parts and flowers of Chromolaena odorata (L.) R. M. King & H. Rob. from Western Ghats Region of North West Karnartha, India. Journal of Essential Oil Bearing Plants. 2013, Vol, pp. 71 - 75. |
| [4] | P. J. Teisseire (1991). Chimie des substances odorantes. s.l.: Technique et documentation-Lavoisier. |
| [5] | M. M. F. Bissangou and J. Ouamba. Valorisation chimique de quelques espèces aromatiques et médicinales du Congo (Ageratum conyzoïdes L, Chromolaena odorata King et Robinson, Hyptis suaveolens Poit et Lippia multitlora Moldenke). Pharma. méd. Trad. Afr. 1997, Vol. 9. pp. 70-84. |
| [6] | H. K. Kossi, D. Kokouvi, F. Bettini and J-C. Bayle. Composition chimique de l’huile essentielle de Chromolaena odorata (L) King et Robinson (Asteraceae) du Togo: Effets de séchage et du site de récolte. J. Soc. Ouest-Afr. Chim. 2009, 028. pp. 11-16. |
| [7] | R. V. Sutherland and J. Jones. 1, 5-dimethylcyclodeca-1, 5, 7-triene, the precursor of geijerene in Geijera parviflora (Lindley). Aust. J. Chem. 1968, Vol. 21, 2255-2264. |
| [8] | K. Kubeczka and I. Ullmann. Occurrence of 1, 5-dimethylcyclodeca-1, 5, 7-triene (pregeijerene) in Pimpinella species and chemosystematic implications. Biochem Syst Ecol. 1980, 8: 39-41. |
| [9] | Kuzovkina and S. H. É. Szarka. Composition of essential oil in genetically transformed roots of Ruta graveolens. Russ J Plant Physl. 2009, 56, 846-851. |
| [10] | J. G. Ali, H. T. Alborn, R. Campos-Herrera, F. Kaplan and L. W. Duncan. Subterranean, Herbivore-Induced Plant Volatile Increases Biological Control Activity of Multiple Beneficial Nematode Species in Distinct Habitats. PLoS ONE. 2012, 7(6), e38146. |
| [11] | G. A. Jared. Subterranean chemical ecology of tritrophic interactions: citrus roots, roots weevils and entomopathogenic nematodes, a dissertation presented to the graduate school of the University of Florida in partial fulfilment, PhD, University of Florida, 2011. |
| [12] | M. Adio. Germacrenes A-E and related compounds: thermal, photochemical and acid induced transannular cyclizations. Tetrahedron. 2009, 65, 1533-1552. |
| [13] | P. Coggon, A. T. McPhail and G. A. Sim. Sesquiterpenoids. Part X. Stereochemistry of pregeijerene: crystal structure of the pregeijerene–silver nitrate adduct. J. Chem. Soc. 1970, B, 1024-1028. |
| [14] | Z. F. Tonzibo, E. Wognin, J. C. Chalchat and Y. T. N’Guessan. Chemical Investigation of Chromolaena odorata L. King Robinson from Ivory Coast. Jeobp. 2007, 10(2), pp. 94-100. |
| [15] | E. L. Wognin, A. F. Brou, T. A. Yapi, K. A. Touré, T. Félix and Z. F. Tonzibo. Multifactorial discriminant analysis of leaf oil of C. odorata L. King and Robinson from Côte d'Ivoire. Afr. J. Pure Appl. Chem. 2015, Vol. 9(2), pp. 18-26. |
| [16] | E. E. Stashenko, R. Acosta and J. R. Martinez. High-resolution gas-chromatographic analysis of the secondary metabolites by subcritical-fluid extraction from Colombian rue (Ruta graveolens L.). J. Biochem. Biophys. Methods. 2000, 43, 379-390. |
| [17] |
Getamap. net. Carte de la Côte d’Ivoire. Available from:
https://fr.getamap.net/cartes/cote_d_ivoire/ (accessed 26 October 2024). |
| [18] | Adams RP. Identification of Essential Oils Components by Gas Chromatography/Quadrupole Mass Spectroscopy. 2007, Carol Stream. USA. |
| [19] |
Wikipedia l’encyclopédie libre. Réaction quantitative. Available from:
https://fr.wikipedia.org/wiki/R%C3%A9action_quantitative# (accessed 25 November 2024) |
| [20] |
Unisciel les sciences l’essentiel. La reaction chimique. Available from:
https://uel.unisciel.fr/chimie/chimther/chimther_ch01/co/apprendre_ch1_07.html (accessed 25 November 2024) |
APA Style
Wognin, E. L., Tanoh, A. E., Yapi, A. T., Toure, K. A., Felix, T., et al. (2024). Thermal Conversion of Pregeijerene into Geijerene in Essential Oil of Chromolaena Odorata L. King & Robinson (Asteraceae). Science Journal of Chemistry, 12(6), 144-152. https://doi.org/10.11648/j.sjc.20241206.14
ACS Style
Wognin, E. L.; Tanoh, A. E.; Yapi, A. T.; Toure, K. A.; Felix, T., et al. Thermal Conversion of Pregeijerene into Geijerene in Essential Oil of Chromolaena Odorata L. King & Robinson (Asteraceae). Sci. J. Chem. 2024, 12(6), 144-152. doi: 10.11648/j.sjc.20241206.14
AMA Style
Wognin EL, Tanoh AE, Yapi AT, Toure KA, Felix T, et al. Thermal Conversion of Pregeijerene into Geijerene in Essential Oil of Chromolaena Odorata L. King & Robinson (Asteraceae). Sci J Chem. 2024;12(6):144-152. doi: 10.11648/j.sjc.20241206.14
Share This Article
Twitter
Linked In
Facebook
Copy
Download@article{10.11648/j.sjc.20241206.14,
author = {Esse Leon Wognin and Amenan Evelyne Tanoh and Acafou Thierry Yapi and Kidjegbo Augustin Toure and Tomi Felix and Zanahi Felix Tonzibo},
title = {Thermal Conversion of Pregeijerene into Geijerene in Essential Oil of Chromolaena Odorata L. King & Robinson (Asteraceae)
},
journal = {Science Journal of Chemistry},
volume = {12},
number = {6},
pages = {144-152},
doi = {10.11648/j.sjc.20241206.14},
url = {https://doi.org/10.11648/j.sjc.20241206.14},
eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20241206.14},
abstract = {It is well-known that geijerene is mostly associated with pregeijerene. These terpenes are believed to be thermoconvertible by a type of sigmatropic transposition order supra or antarafaciale. Our contribution to the study of the molecular pair consisted on a combination of statistical and analytical approach to the chemical composition of Chromolaena odorata essential oil. A compilation of chemical compositions of the samples obtained by steam distillation and analyzed by GC, presented a variation of this binomial proportions in different countries. For Ivory Coast, the results of analysis of 71 samples showed a dominance of geijerene proportion. We carried out a two-stage sampling by chemical variability factors (effects of site and period). We chose, at random, three different samples we submitted separately to chromatographic analysis (GC) and spectroscopic analysis (13C-NMR). It appears from this study that pregeijerene and geijerene were found in the essential oil with a relationship characterized by a polynomial degree 6 between these both molecules. Then during the chromatographic analysis, thermal conversion of pregeijerene into geijerene with the ratio 85.8% was observed. This result supported the idea of the coexistence of pregeijerene and geijerene in the essential oil of Chromolaena odorata. We intend to help clarify the kinetics and complete thermodynamics of this equilibrium.
},
year = {2024}
}
TY - JOUR T1 - Thermal Conversion of Pregeijerene into Geijerene in Essential Oil of Chromolaena Odorata L. King & Robinson (Asteraceae) AU - Esse Leon Wognin AU - Amenan Evelyne Tanoh AU - Acafou Thierry Yapi AU - Kidjegbo Augustin Toure AU - Tomi Felix AU - Zanahi Felix Tonzibo Y1 - 2024/12/30 PY - 2024 N1 - https://doi.org/10.11648/j.sjc.20241206.14 DO - 10.11648/j.sjc.20241206.14 T2 - Science Journal of Chemistry JF - Science Journal of Chemistry JO - Science Journal of Chemistry SP - 144 EP - 152 PB - Science Publishing Group SN - 2330-099X UR - https://doi.org/10.11648/j.sjc.20241206.14 AB - It is well-known that geijerene is mostly associated with pregeijerene. These terpenes are believed to be thermoconvertible by a type of sigmatropic transposition order supra or antarafaciale. Our contribution to the study of the molecular pair consisted on a combination of statistical and analytical approach to the chemical composition of Chromolaena odorata essential oil. A compilation of chemical compositions of the samples obtained by steam distillation and analyzed by GC, presented a variation of this binomial proportions in different countries. For Ivory Coast, the results of analysis of 71 samples showed a dominance of geijerene proportion. We carried out a two-stage sampling by chemical variability factors (effects of site and period). We chose, at random, three different samples we submitted separately to chromatographic analysis (GC) and spectroscopic analysis (13C-NMR). It appears from this study that pregeijerene and geijerene were found in the essential oil with a relationship characterized by a polynomial degree 6 between these both molecules. Then during the chromatographic analysis, thermal conversion of pregeijerene into geijerene with the ratio 85.8% was observed. This result supported the idea of the coexistence of pregeijerene and geijerene in the essential oil of Chromolaena odorata. We intend to help clarify the kinetics and complete thermodynamics of this equilibrium. VL - 12 IS - 6 ER -
Preparatory School for the High Schools, Felix Houphouet Boigny National Polytechnic Institute, Yamoussoukro, Ivory Coast
Training and Research Unit-Sciences of the Structures of Matter and Technology, Felix Houphouet Boigny University, Abidjan, Ivory Coast
Training and Research Unit-Sciences of the Structures of Matter and Technology, Felix Houphouet Boigny University, Abidjan, Ivory Coast
Preparatory School for the High Schools, Felix Houphouet Boigny National Polytechnic Institute, Yamoussoukro, Ivory Coast
Chemistry and Biomass Team, University of Corsica, Ajaccio, France
Training and Research Unit-Sciences of the Structures of Matter and Technology, Felix Houphouet Boigny University, Abidjan, Ivory Coast
Information