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Essential Oils of Nigeria II: Analysis of the Leaf Oil of Securidaca Longependuculata Fers.

September 19, 2007

By Adebayo, Muritala A Karioti, Anastasia; Skaltsa, Helen; Ogunwande, Isiaka A

Key Word Index Securidaca longepedunculata, Polygalaceae, essential oil composition, methyl salicylate.

Introduction

Nigeria is blessed with a diversity of flora, most of which has remained unexploited for their chemical constituents and biological potentials. Securidaca longepedunculata Fers. (Polygalaceae) is commonly used as a medicine in many parts of Africa. In Nigeria, the plant is commonly employed for the treatment of inflammatory conditions and as purgative. An oral administration of a decoction of the root has been shown to produce a sedative effect, mainly attributed to its content of oleanolic acid glycoside (1). Extracts of the plants from Nigeria has been reported to possess both gastrointestinal and trypanocidal effects (2,3). Elsewhere considerable antimalarial (4), insecticidal (5) and insect repellent activities (6) have been confirmed for extracts from various parts of the plant.

On the chemical point of view, ergonine alkaloids (7) and tannins of the presenegamine skeleton (8) have been characterized from the plant. Two minor bitter principles: beta-D-(3, 4-dismapoyl)- fructofuranosyl-alpha-D-(6-sinapoyl)-glucopyrano-side and beta-D-(3- disinapoyl)-fructofuranosyl-alpha-D-(6-sinapoyl)-glucopyranoside have been described from die bark extracts (9). The seed oils have an abundant of hydroxydienoic fatty acids and acetotriacylglycerols (10). Previous research works on the volatde oils have been focused on the root. Costa et al. (11) identified mediyl 4-hydroxybenzoate (mediyl paraben) as die dominant volatile compound of the ether extract of the root oil of the plant. In addition, nine others compounds of the benzoic acid derivatives were also characterized. Lognay et al. (12) reported the occurrence of methyl salicylate and 2-hydroxy-6-methoxybenzoic acid methyl ester in S. longepedunculata root bark from Senegal. Later Jayasekara et al. also identified mediyl salicylate (2-hydroxy benzoic acid methyl ester) as the principal volatile component in the medianol extract of the root bark of the plant from Ghana (13). Methyl salicylate was also reported by Nebe and co- workers (14), as the dominant compound in die root bark oil of the plant from Burkina Faso. Mediyl salicylate was identified as the compound responsible for the fumigant property of the root of the plant (12).

To the best of our knowledge, there is no report in the literature on the constituents of the volatile fraction of the leaf of the plant from Nigeria and elsewhere. This paper reports on the compounds identified from the oil of the leaf of S. longependuculata grown in Nigeria.

Experimental

Plant material and oil isolation: The leaves of S. longependuculata were coUected from trees growing at a location in Bode-Osi, Headquarters of Ola-Oluwa Local Government, Osun State, Nigeria, in October, 2004.

The plant sample was authenticated by F. Usang of the Herbarium Headquarters, Forestry Besearch Institute of Nigeria (FRIN), Ibadan, Nigeria, where a voucher specimen (FHI 106976) has been deposited for future reference. The essential oil was obtained by hydrodistilltion of the air-dried and pulverized plant materials (500g) using a Clevenger-type apparatus with a water-cooled oil receiver to reduce hydrodistillation over-heating artifacts according to the British Pharmacopoeia (15). The oil, dried over anhydrous sodium sulfate, collected in a screw-capped vial and kept under refrigeration untd needed. The yield of the oil was 0.45% v/ w.

Analysis of volatile compounds: The composition of the volatde constituents was established by GC and GC/MS analyses. GC analysis was carried out on a Perldn Elmer 8500 gas Chromatograph with FID, fitted with a Supelcowax – 10 fused sdica capdlary column (30 m x 0.32 mm; film thickness: 0.25 pm). The column temperature program was from 75[degrees]-250[degrees]C at a rate of 2.5[degrees]C/min. The injector and detector temperatures were programmed at 230[degrees]C and 300[degrees]C, respectively. Relative percentage amounts were calculated from GC (FID) analysis. GC/MS analyses were performed on a Hewlett-Packard 5973-6890 system operating in EI mode (70eV) equipped with a split/splitless injector (220[degrees]C), a split ratio 1/10, using a fused silica HP-5 MS capdlary column (30m x 0.25mm), film thickness: 0.25[mu]m). The temperature program for HP-5 MS column was from 60[degrees]C (5min) to 280[degrees]C at a rate of 4[degrees]C/min. Helium was used as a carrier gas at a flow rate of 1.0 mL/min. Injection volume of each sample was 2 [mu]L. Retention indices for all compounds were determined according to the Van der Dool approach (16), using n-alkanes as standards. The identification of the components was based on comparison of their mass spectra with those of Wiley and NBS Libraries (17) and those described by Adams (18), as well as by comparison of their retention indices with literature data (18, 19). In some cases, the oil was subjected to co-chromatography with authentic compounds (Fluka, Sigma). Optical rotation was measured on a Perkin-Elmer 341 Polarimeter.

Results and Discussion

The identified compounds from the oil of S. hngependuculata are listed in Table I according to their elution order, along with their retention indices and percentage composition. Altogether, 14 compounds were identified amounting to 94. 1% of the oil constituents. Methyl salicylate was the singly most abundant constituent (89.6%), which is consistent with earlier results into the root volatde oils of the plant from various countries (12-14). Methyl salicylate is known to widely occur in many plants of the Polygalaceae famdy (13). The occurrence of the rare ethyl and hexyl esters of salicylic acid found in the present study seems to be a characteristic feature of the plant. Except for its 1,8-cineole content (1. 1%), all other compounds were identified in amounts less than 1%.

Previous workers (12-14) have identified methyl salicylate as the dominant constituent of the oil of the root bark of the plant. Costa et al. (11) described their own oil content to be made up of mediyl 4-hydroxybenzoate (mediyl paraben), contrary to other reports, which Jayasekara et al. (13) had contended to be misidentified and that the compound was actuaUy methyl salicylate. Mediyl paraben was not identified in the present study. However, it is noteworthy that conventional mono- and sesquiterpenoid compounds (such as alpha- pinene, beta-pinene, 1, 8-cineole, alpha-cadinol etc) that were reported in this study were not described before as constituents of the oil of S. longependuculata. Hexadecanoic acid was also being reported for the first time in the oil sample.

Table I. Percentage composition of the volatile oil of Securidaca longependuculata

Acknowledgments

The authors are grateful to Mr. Essien (CL- mistry Department, University of Ibadan, Nigeria) for the isolation of the oil from the plant material.

References

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5. S.R. Belmain, G.E. Neal, D.E. Ray and R Golob, lnsecticidal and vertebrate toxicity associated with ethnobotanicals used as post- harvest protectants in Ghana. Food Chem. Toxicol., 39, 287-291, (2001).

6. S.J. Boeke, I.R. Baumgart, J.J.A. Van Loon, A. Van Huis, M. Dicke and D. K. Kossou, Toxicity and repellence of African plants traditionally used for the protection of stored cowpea against Callosobruchus maculates. J. Stor. Prod. Res., 40, 423-438, (2004).

7. M. Scandola, D.E. Games, C. Costa, G. Allegri, A. Bertazzo, O Curcuruto and RTraldi, Structural study of alkaloids fromSecuridaca longipedunculata roots II. Isolation and characterization by supercritical fluid chromatography/ mass spectrometry. J. Het. Chem., 31, 219-224, (1994).

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12. G. Lognay, M. Marlier, D. Seek and E. Haubruge, The occurrence 12. of 2-hydroxy-6-methoxybenzoic acid methyl ester in Securidaca longependuculata Fresen root bark, Biotechnol. Agron. Soc. Envir., 4, 107-110,(2004). 13. T.K. Jayasekara, RC. Stevenson, S.R. Belmain, D.I. Farman and D.R. Hall, 13. Identification of methyl salicylate as the principal volatile component in the methanol extract of root bark of Securidaca longependuculata Fers. J. Mass Spectr., 37, 577-80, (2002).

14. R.H.C. Nebie, R.T Yameogo, A. Belanger and FS. Sib, Salicylate de 14. methyle, constituent unique de l’huile essentielle de l’ecorce des raciness de Securidaca longependuculata du Burina Fasso., Compt. Rend. Chimie, 7, 1003-1006, (2004).

15. British Pharmacopoeia, Vol. II. Her Majesty’s Stationery Office, Appendix 15. XIE p. A111, University Press, Cambridge (1980).

16. H. Van den Dool and RD. Kratz, A generalization of the retention index system Including linear temperature programmed gas- liquid partition chromatography. J. Chromatogr. A, 11, 463-471, (1963).

17. Y. Massada, Analysis of essential oil by gas chromatography and spectrometry. John Wiley & Sons, New York, NY (1976).

18. R. Adams, Identification of Essential Oil Components by Gas Chromatography/ Mass Spectroscopy. Allured Publishing Co., Carol Stream, IL (2001).

19. N.W. Davies, Gas chromatographic retention indices of monoterpenes and sesquiterpenes on methyl silicon and Carbowax 20M phases. J. Chromatogr. A, 503, 1-24, (1990).

Muritala A. Adebayo,

Department of Pharmacognosy, University of Ibadan, Ibadan, Nigeria

Anastasia Karioti and Helen Skaltsa,*

Department of Pharmacognosy and Chemistry of Natural Products, School of Pharmacy, University of Athens,Panepistimi

oplois, Zografou 157 71 Athens, Greec;

Isiaka A. Ogunwande,

Laboratory of Food Analysis, Institute of Biotechnology ; Division of Bioresources and Bioenvironmental Sciences, Faculty

of Agriculture, Graduate School of Kyushu University 6-10-1- Hakozaki, Higasshi-ku, Fukuoka-shi 812 8581, Japan

* Address for correspondence

Received: March 2006

Revised: May 2006

Accepted: May 2006

1041-2905/07/0005-0452$14.00/0-(c) 2007 Allured Publishing Corp.

Copyright Allured Publishing Corporation Sep/Oct 2007

(c) 2007 Journal of Essential Oil Research : JEOR. Provided by ProQuest Information and Learning. All rights Reserved.