Chemical Composition of Essential Oil of Hyptis Suaveolensis(L) Poit. from Côte d Ivoire

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1 European Journal of Scientific Research ISSN X Vol.38 No.4 (2009), pp EuroJournals Publishing, Inc Chemical Composition of Essential Oil of Hyptis Suaveolensis(L) Poit. from Côte d Ivoire Z. F. Tonzibo Laboratoire de Chimie Organique Biologique UFR Sciences des Structures de la Matière et de la Technologie Université de Cocody, 22 BP 582 Abidjan 22, Côte d Ivoire. tonzibz@yahoo.fr Affia Brou Florence Laboratoire de Chimie Organique Biologique UFR Sciences des Structures de la Matière et de la, Technologie, Université de Cocody 22 BP 582 Abidjan 22, Côte d Ivoire G. Bédi Laboratoire de Chimie Organique Biologique UFR Sciences des Structures de la Matière et de la Technologie Université de Cocody, 22 BP 582 Abidjan 22, Côte d Ivoire J. C. Chalchat Laboratoire de Chimie des Huiles essentielles Université Blaise Pascal de Clermont-Ferrand Abstract Essential oils of aerial parts of Hyptis suaveolens (L) Poit. collected in different locations on Côte d Ivoire were obtained by hydrodistillation and analyzed by GC and GC/MS. The oil of leaves from M batto (east) was predominated by sabinene (8-20,8%), β- caryophyllene (13,1-30,2%), benzyl benzoate (13,6-30,2%) and a diterpene hydrocarbon II (7,9-16,8%), when oil of stems in the same locality was rich in sabinene (1,4-9,4%), β- caryophyllene (16,3-31%), dierpene hydrocarbon II (11,1-15,1%) and palustrol (8-16,7%). The chemotype of leaves from Jacqueville (South-east) was constitued by 1,8-cineole (11,9%) and β-caryophyllene (32,5%). The oil of leaves from Bouafle (West) was constitued mainly by β-caryophyllene (33,9%) and germacrene D (25,4%). Keywords: Hyptis suaveolens (L), Lamiaceae, essential oil composition, Côte d Ivoire, Sabinene, β-caryophyllene, Benzyl benzoate, Germacrene D, Palustrol, chemotypes. 1. Introduction Hyptis suaveolens (L.) Poit. (Lamiaceae) is fast-growing perennial herb found in dense clumps along roadsides, in over-grazed pastures and around stockyards in the tropics. Its branched, semi-woody

2 Chemical Composition of Essential Oil of Hyptis Suaveolensis(L) Poit. from Côte d Ivoire 566 stems can reach a height of 2m, and the plant gives off a characteristic minty smell when crushed. Originally native to tropical America, it is now considered a weed worldwide. H. suaveolens is used traditionnaly for the treatment of respiratory track infections, colds, pain fever, cramps and skin diseases (Iwu M. M., 1993; Mabberley D. J. 1990). The leaves are used as an anticancer (Olivier-Bever B., 1986) and antifertility agent (Daziel J. M., 1937). Essential oils isolated from aerial parts of this plant have showed, antifungal (Pandey D. K. et al, 1982 ; Singh G. et al, 1992; Zollo Amvam PH et al, 1998),antibacterial (Iwu M. M., et al 1990; Askun O.T., 1990) and anticonvulsant (Akah P. A. et al 1990) activities. Recently Chukwujekwu et al (2005) reported significant antiplasmoidal activity in a petroleum ether extract of H. suaveolens. From chemical point of view H. suaveolens had reported to contain non-volatile coumpounds(.aspinall G.O et al 1984; Aguirre C., et al 2004) the wide variety of essential oil. The chemical composition of essential oils of Hyptis suaveolens (L) from various origins have been the suject of many studies. The litterature reveals the occurence of several chemotypes, β-caryophyllene was major component of oil from Malaysia (Din L. B., et al 1988) and Nigeria (Iwu M. M., et al 1990). 1,8-cineole and sabinene-type of oil was described from USA (Ahmed M., et al 1994), Indian (Mallavarapu G.R. et al, 1993) and Aruba (Fun C. E.; et al 1990). When 1,8-cineole was identified as mainly component of oil from Brazilian Northeast (Craveiro A. A., at al 1981; Luz A. I. R. et al, 1984), it reported by Gottlied et al (1981) that 1,8- cineole and β-pinene were the major components of the oil from Brazilian Amazonian. The oils from Brazilian Cerrado (Azevdo N. R., et al 2002; Marcio J., et al 2005) were rich in sabinene, limonene, 1,8-cineole, β-caryophyllene and spathulenol. In vietnam, Le Van Hac et al (1996) have reported eugenol and germacrene-d as main components. The predominance of limonene and fenchone in oil of H. suaveolence from Venezuela was noted by Flores S. E., et al (1970). Malele R. S. and al (2003) have described the oil of leaves from Tanzania predominated by α-elemene and β-caryophyllene. Sabinene/β-caryophyllene-type was identified in oil from Cameroon (Zollo Amvam PH et al, 1998). Sidibe L. et al (2001) have described β-caryophyllene and trans-α bergamotene as major components of oil from H. suaveolens from Mali. The present article reports for the first time, the comparative analyses of the essential oils obtained from H. suaveolens collected in Côte d Ivoire. 2. Experimental 2.1. Plant Material and Extraction Leaves of wild plants of H. suaveolens were collected between May and December 2007 from different locations of Ivory coast: M batto (East), Jacqueville (South- east) and Bouaflé (West). Fractions of 500g of fresh leaves were submitted to hydrodistillation for 3h using a Clevengertype apparatus. The oils obtained by decantation were dried over anhydrous sodium sulphate Identification of Oil Composition GC analyses were performed on a DELSI 121C gas chromatograph (FID) with a fused silica WCOT capillary column (25x 0.3mm, 0.15µm film thickness) and CP WAX 52 CB stationary phase. The temperature was programmed from 50 C with 5min initial hold and then to 210 C at 2 C/min, using N 2 as the carrier gas. GC/MS analyses were performed on a Hewlett-Packard instrument with a fused silica WCOT capillary colomn (50 m x 0.3 mm, 0.25 µm film thikness) CP WAX 51, temperature programmed from C at 3 C/min using He as the carrier gas. Compounds were identified by their retention indices to known compounds and comparison on their mass spectra either with known compounds for published listed spectra (Adams R. P. 1989; Swigar A. A. et R. M. Silvestein 1981).

3 567 Z. F. Tonzibo, Affia Brou Florence, G. Bédi and J. C. Chalchat 3. Results and Discussion Pale yellow oils were obtained by hydrodistillation of fresh aerial parts of H. suaveolens. The yields were % and % respectively for leaves and stems from M batto, 0.08% and 0.1% for leaves respectively from Jacqueville and Bouaflé. The result of the analysis displayed in Table 1 shows different compositions. Oxygenated compounds have presented relatively small proportions, particularly monoterpenes and oxygenated diterpenes with every total percentage was lower to 19%. On the other hand, sesquiterpene hydrocarbons showed the most important amount reaching 86.1%, marked by β-caryophyllene and germacrene D in agreement whith litterature. But the important proportions of diterpenes, benzyl benzoate and palustrol in oils of leaves and stems from M batto have never been reported. Besides in this paper, we present the main peaks of the results of mass spectrometer of the three diterpene hydrocarbons obtained by GC/SM. The differences between chemical compositions of H. suaveolens oils, could be distinguished as follows: 1. H. suaveolens harvested from M batto showed an oil of leaves predominated by sabinene (8-20.8%), β-caryophyllene ( %), benzyl benzoate ( %) and diterpene hydrocarbon II ( %). When β-caryophyllene ( %), diterpene hydrocarbon II ( %) and palustrol (8-16.7%) were the main components of essential oil of stems. 2. H. suaveolens harvested from Jacqueville gave an essential oil of leaves rich in 1,8-cineole (11.9%) and β-caryophyllene (32.5%), with sabinene (9.2%) and benzyl benzoate (7%) were noted as minor constituents. 3. H. suaveolens harvested from Bouaflé gave an oil predominated by sesquiterpene hydrocarbons, marked by β-caryophyllene (33.9%) and germacrene D (25.4%) as major components, while germacrene B (8.2%) and α-humulene (8.3%) had low amounts. Finally the essential oils composition of H. suaveolens growing on the Côte d Ivoire showed important difference of those reported in literature, marked by new chemotypes. We propose further study of isolation and establishment of chemical structure of the diterpen hydrocarbons (I,II,III) using RMN 1D and 2D. Nevertheless, the predominance of β-caryophyllene, in oils composition from Africa (Nigeria, Cameroon, Tanzania, Mali) in comparison with ours samples, seems to characterize the species of H. suaveolens, in its chemical aspect.

4 Chemical Composition of Essential Oil of Hyptis Suaveolensis(L) Poit. from Côte d Ivoire 568 Table 1: Pencentage composition of essential oils of Hyptis suaveolens from Côte d Ivoire KI Compounds Localities M batto Jacqueville Bouaflé (August-December2007) (August 2007) (May 2007) leaves stems leaves leaves 924 Tricyclene - t- 0,4 926 α-thujene 0,1-0,3 t- 0,2 934 α-pinene 0,5-1,5 t- 0,5 950 Camphene t- 0,1 975 Sabinene 8-20,8 1,4-9,4 9,2 979 β-pinene 2,2-4,6 0,3-1,8 3 0,4 981 oct-1-en-3-ol 0,1-1,6 t- 0,3 989 Myrcene 0,2-0,3 997 Octan-3-ol t- 0, α-phellandrene t- 0, Δ 3 -Carene 0,2-0, α-terpinene 0,1-1,3 t- 0, p-cymene 0,1-0,5 t- 0, Limonene 1,5-3,1 0,6-1,3 3,4 0, β-phellandrene 0,1-0,4 t- 0, ,8-Cineole 0,1-5 11, (Z)-β-Ocimene t- 0, γ-terpinene 0,3-2,1 0,3-0, Cis-Sabinène hydrate 0,2-0, Terpinolene 4,5-7,2 1,8-4,2 4, p-cymenene 0,1-0,4 t- 0, Linalool t- 0, Trans-Sabinene hyrdrate 0,1-0, exo Fenchol 0,1-0,4 t- 0, cis Menth-2-en-1-ol t-0, trans Menth-2-en-ol t- 0, Borneol t- 0, Terpinen-4-ol 0,2-3,8 0,5-2 2, p-cymene-8-ol 0,2-0, α-terpineol t- 0, Thymol methyl ether t- 0, Carvacrol methyl ether t- 0, Bornyl acetate t- 0, Thymol t- 0,1 t- 0,2 4 0, δ-elemene 0, α-copaene t- 0,1 2, β-bourbonene 0, β-elemene 0,1-0,5 0,2-0,4 2, γ- Caryophyllene t- 0,1 0, p-cymene <2,5- dimethoxy> t- 2, β-caryophyllene 13,1-30,2 16, ,5 33, β-copaene 0, trans α-bergamotene 2,2-4,2 2,6-4,8 3,9 0, (E)- β Farnesene 0,2-0,3 0,2-0, α-humulene 0,8-1,8 1,2-1,9 8, allo Aromadendrene 0,1-0,9 t- 0, β-chamigrene t- 0,1 2, γ-muurolene t- 0,1 t- 0,3 2, Germacrene D 25, α-selinene 0,1-1,6 1,2-1,8 0, Viridiflorene 0,9-1,4 t- 0,3 3, Bicyclogermacrene 2-4,6 2,4-5,1 4,2 0, Germacrene- A t- 0,2 t- 0,3

5 569 Z. F. Tonzibo, Affia Brou Florence, G. Bédi and J. C. Chalchat 1515 γ-cadinene t- 0, δ-cadinene t- 0,1 1, Elemol 0,1-03 t- 0, Elemicine t- 0, Germacrene B 8, Spathulenol 0,2-0,8 0,5-1,1 0, Globulol 0,4-1,5 0,9-1,7 2,9 1, Humulene <1,2-epoxide> t- 0,1 0, γ-eudesmol<10-epi> 0,5 t- 0, Caryophylla-4(14),8(15)-dien-5- β-ol t- 0, epi-α-muurolol 0,1-0,8 t- 0, α-cadinol 0,1-0,3 0,3-0, neo Intermedeol t- 0,4 t- 0, hydroxy-9-épi-(E)- Caryophyllène 0,2-0,5 t- 0, Intermedeol t- 0, α-asarone t- 0, (Z)-trans-α-Bergamotol 1,6-3,9 3,1-6, Benzyl benzoate 13,6-21,5 0,9-1, Diterpene hydrocarbon I 0,2-0,9 4, Diterpene hydrocarbon II 7,9-16,8 11,1-15,1 4, Abieta-8,12-diene 0,1-0,3 t- 0, Abietatriene 1,3-5 t- 3, Diterpene hydrocarbon III 1-1,2 t- 1, Abetadiene 0,9-2,6 1,6-2, Phytol 4, Abieta-8(14),13(15)-diene 0,1-0,2 t- 0, Palustrol 0,7-4,6 8-16, Dehydroabietol 0,1-0,7 t- 1,8 Monoterpène hydrocarbons 19,9 0,6 Oxygen-containing monoterpènes 18,4 0,5 Sesquiterpène hydrocarbons 46,8 86,1 Oxygen-containing sesquiterpènes 9,9 1,8 Diterpene hydrocarbons 4,8 Oxygen-containing diterpenes 4,3 Total (%) 99,8 96,2 KI= Koväts Indice on CP WAX 52 CB capillary colunm t: trace C 20 H 32 (I), MS (EI): 40(100%); 55(35%); 69(29%); 69(29%); 79(41%); 91(35%); 105(42%); 119(35%); 131(24%); 161(29%); 187(24%); 257(95%); 272(29%). C 20 H 32 (II), MS (EI): 40(60%); 55(18%); 69(62%); 81(18%); 91(100%); 106((56%), 125(51%); 137(14%); 147(37%); 159(12%); 192(12%); 215(13%); 257(13%); 272(18%). C 20 H 32 (III), MS (EI): 43(20%); 55(11%); 69(34%); 117(20%); 129(26%); 143(20%); 150(20%); 159(62%); 173(60%); 185(37%); 199(11%); 255(100%); 270(37%), 272(11%).

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