American Journal of BioScience
Volume 3, Issue 4, July 2015, Pages: 117-120

Determination of Volatile Compounds from Commiphora myrrha (Nees) Engl. Resin Marketed in Central Sudan by GC/MS

Hatil Hashim EL-Kamali1, *, Badr Omer Burham2, Awatif Abdel Bagi EL-Egami3

1Department of Botany, Faculty of Science and Technology, Omdurman Islamic University, Omdurman, Sudan

2Department of Chemistry, Faculty of Science, AL-Baha University, AL-Baha, Saudi Arabia

3Department of Phytochemistry, Medicinal and Aromatic Plants Research Institute, National Centre for Research, Ministry of Science and Technology, Khartoum, Sudan

Email address:

(H. H. EL-Kamali)
(B. O. Burham)
(A. A. B. EL-Egami)

To cite this article:

Hatil Hashim EL-Kamali, Badr Omer Burham, Awatif Abdel Bagi EL-Egami. Determination of Volatile Compounds from Commiphora myrrha (Nees) Engl. Resin Marketed in Central Sudan by GC/MS. American Journal of BioScience. Vol. 3, No. 4, 2015, pp. 117-120. doi: 10.11648/j.ajbio.20150304.11


Abstract: The medicinal properties attributed to resins of this plant in Sudanese traditional medicine prompted us to study the chemical composition of the oil. The GC/MS chromatogram of the oil revealed the presence of 58.86% monoterpenes and 23.28% sesquiterpenes. Predominant monoterpenoids were; m-cymene (21.56%), linalool (7.21%) and p-mentha-1-en-8-ol (5.28%) while the predominant sesquiterpenoids were; alpha-guaiene (3.55%) and C15H24 (3.23%).

Keywords: Commiphora myrrha, Essential Oil Composition, Resins, Sudan


1. Introduction

Continuing our investigations on chemistry of essential oils from aromatic plants used in Sudanese Traditional Medicine [1] – [5], we have analyzed the essential oil of Commiphoramyrrha. The resin is used by the Sudanese local people to treat various ailments.It was masticated as antiseptic. A paint was prepared for skin diseases and pustule complaints. Resins obtained from various other species of Commiphora were used as substitute of C. myrrha. This complicates the characterization of myrrh, because most previous chemical studies reported on the resin were based on commercial material, and not on a product obtained from properly identified trees [6].

The aim of this paper is to present qualitative and quantitative analysis of the oil of this plants species marketed in the central Sudan.

2. Materials and Methods

2.1. Plant Material

The plant material (resin) used in this study was purchased in April, 2010 from Bahry Market, Khartoum State, Sudan. Based on the available specimen, the plant material was identified as C. myrrha by one of the author, Prof. H.H EL-Kamali.

2.2. Preparation and Isolation of Volatile Component

The resin sample of C. myrrha was subjected to hydrodistillation for 4 h using a Clevenger – type apparatus. The oil was dried over anhydrous sodium sulfate and stored at 5 C until analysis [7].

2.3. Gas Chromatographic–Mass Spectrometry (GC/MS)

GC-MS analyses were performed on a QP-2010 Shimadzu spectrometer instrument. Fused silica capillary column with stationary phase was used: (50% phenyl and dimethylpolysiloxane) and (50% dimethylpolysiloxane), 30 m, 0.25 mm diameter. The analytical conditions were as follows: carrier gas , helium ; injector temperature , 250 C; temperature program, 1 min at 70C rising to 220 C at a rate of 3 C/min. Individual components were identified by comparison of the retention times and mass spectra provided by Wiley Library in the data system and literature [8].

3. Results and Discussion

Light yellow volatile oil was obtained by hydrodistillation of dried resin of C. myrrha in 2.1 % yield. Table 1 shows the relative percentages, formula, class type, retention time, mass peaks, base peaks and main fragment ions of the constituents of the C. myrrha resin oil.

Table 1. chemical composition of Commiphora myrrha resin.

NO Compound % Formula Class Type Retention Time (RT) Mass peaks Base peaks Main fragment ions (m/z)
1 Delta-3-carene 0.07 C10H16 MH 6.700 300 93.05 53,67,79,93,105,121,163
2 alpha-terpinene 0.05 C10H16 MH 17.687 293 121.10 55,65,79,93,105,121,136,
3 Gamma-elemene 0.68 C15H24 SH 17.862 145 121.10 55,67,77,93,105,121,136,148,161
4 (-)-alpha-muurolene 0.03 C15H24 SH 18.357 315 105.05 55,67,91,105,119,129,149,161,176,189,204
5 Copaene 0.1 C15H24 SH 19.560 299 105.05 55,69,81,93,105,119,133,147,161,169,189,204
6 Unidentified 0.42 C15H24 SH 19.883 195 81.10 53,67,81,91,105,123,133,147,161
7 8,8-Dimethyl-9-methylene-1,5-cycloundecadiene 3.81 C14H22 - 20.174 109 93.05 55,67,81,93,107,121,133,147,161,175,189,204
8 1H-cycloprop[e]azulene,1a,2,3,4,4a,5,6,7b-octahydro-1,1,4,7-tetrameth 0.06 C15H24 SH 20.686 313 204.20 55,65,79,91,105,119,133,147,161,175,189,204
9 Beta-caryophellene 0.63 C15H24 SH 21.389 267 93.10 55,69,79,93,105,120,133,147,161,175,189,204
10 Germacrene B 0.60 C15H24 SH 21.850 227 121.10 55,67,97,93,107,121,133,147,161,175,189,204
11 Unidentified 0.03 C29H42O - 22.034 311 119.05 55,69,79,93,107,119,131,147,161,175,189,204
12 Unidentified 0.07 C15H24 SH 22.431 300 161.05 55,67,81,91,105,119,133,147,161,177,204
13 Humulene 0.22 C15H24 SH 22.889 267 93.10 55,67,80,93,107,121,133,147,161,175,189,204
14 Caryophyllene 0.12 C15H24 SH 23.067 324 91.05 55,67,79,91,105,119,133,147,161,175,189,204
15 Nopol 0.03 C11H18O - 23.503 338 105.05 55,67,79,93,105,119,133,147,161,176,189,204
16 Cyclosativene 0.14 C15H24 SH 23.736 286 161.15 55,67,79,93,105,119,133,146,161,176,189,204
17 E-germacrene D 1.17 C15H24 SH 23.970 132 161.10 55,67,81,91,105,119,133,147,161,176,189,204
18 Unidentified 0.65 C15H24 SH 24.290 286 93.05 55,67,79,93,105,121,147,161,175,189,204
19 Iso-furano-germacrene 21.02 C15H20O OS 24.574 140 108.05 53,65,79,91,108,119,133,148
20 (+)-alpha-muurolene 0.07 C15H24 SH 24.740 284 105.05 55,65,81,91,105,119,133,147,161,175,189,204
21 1H-Benzocycloheptene, 2,4a,5,6,7,8,9,9a- octahydro-3,5,5-trimethyl-9-methylene 0.18 C15H24 SH 24.904 316 93.05 55,67,81,93,105,119,134,147,161,176,189,204
22 Bicyclo[5.2.0]nonane4-ethenyl-4,8,8-trimethyl-2-methylene 0.31 C15H24 SH 25.054 299 93.05 53,67,79,93,107,119,133,147,161,175,189,204
23 Alpha-cubebene 0.47 C15H24 SH 25.315 226 161.10 55,67,79,91,105,119,133,148,161,176,189,204
24 Alpha-elemene 0.28 C15H24 SH 25.545 268 161.10 55,67,81,91,105,119,134,147,161,176,189,204
25 Guaiene 0.11 C15H24 SH 26.262 307 105.05 55,67,81,91,105,119,133,147,161,176,189,204
26 Beta-patchoulene 0.12 C15H24 SH 26.441 315 161.10 55,67,81,91,107,122,133,142,161,175,189,204
27 Gamma-caryophyllene 0.08 C15H24 SH 26.781 327 93.05 55,59,81,93,107,119,135,148,161,175,189,204
28 Gamma-elemene 3.34 C15H24 SH 27.121 123 121.10 53,67,81,93,105,121,133,147,161,175,189,204
29 p-cresyl-n-butyrate 0.70 C11H14O2 - 27.860 117 108.05 53,65,79,91,108,115,128,141,155,165,183,199,214
30 Cyclopropancarboxylic acid,2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-,2-methyl-4-oxo-3-(1,3-pentadien-1-yl)-2-cyclopenten-1-yl ester 0.07 C21H28O3 - 28.507 279 123.10 53,81,93,105,123,134,153,159,169,183,197,212,229
31 Unidentified 0.05 C14H18 - 28.637 330 118.00 53,67,77,91,108,118,128,141,157,171,186,199,214
32 Unidentified 0.03 C11H14O2 - 28.868 319 122.00 53,65,77,94,108,122,131,149,162,174,187,202,215,230
33 Cubenol 0.12 C15H26O OS 29.432 315 119.10 55,67,81,95,105,119,133,147,161,179,187,204
34 Unidentified 48.68 C16H18O2 - 29.856 146 108.05 51,65,79,91,108,118,128,143,159,181,185,199,214
35 Unidentified 13.59 C14H14O2 - 30.152 141 109.05 53,65,79,91,109,115,128,141,155,171,183,199,214
36 Bicyclo[4.4.0]dec-1-ene,2-isopropyl-5-methyl-9-methylene 0.95 C15H24 SH 30.484 160 161.10 55,69,81,95,105,119,134,147,161,176,189,204
37 Unidentified 8.96 C16H24 - 32.383 156 108.05 53,65,79,93,108,115,131,145,159,173,187,201,216
38 Germacron 0.03 C15H22O OS 31.287 297 107.10 53,67,79,93,107,121,135,149,161,175,200,217
39 Unidentified 1.23 C15H24 SH 31.530 189 93.10 55,67,81,93,107,121,133,147,161,175,189,204
40 Unidentified 0.42 C17H16O2S - 32.083 271 123.05 45,65,79,91,107,123,138,159,173,191,214,231,246
41 Thujen-2-one 3.98 C10H14O OM 32.383 154 108.05 53,65,79,93,108,115,131,145,159,173,187,201,216
42 Unidentified 3.80 C10H14O3 - 33.227 174 123.05 45,65,79,91,107,123,138,147,159,178,191,199,214,231,246
43 Eudesm-4-en-11-ol 0.18 C15H26O OS 35.776 312 161.01 55,67,79,93,107,121,133,147,161,175,189,204
44 Unidentified 0.06 C10H14 MH 36.843 322 106.05 55,65,83,91,106,119,125,145,159,174,187,202,215,230
45 9,12,15-Octadecatrienal, dimethyl acetal 0.12 C20H36O2 - 39.317 324 108.05 55,65,79,91,108,119,133,146,159,172,185,199,214,232,239,258,274
46 Unidentified 0.06 C13H18O2 - 40.956 338 146.10 55,69,79,91,108,119,135,146,159,171,185,199,214
47 Unidentified 0.05 C16H20 - 42.302 337 197.00 53,67,77,91,108,115,128,142,155,169,185,197,212,228,254,272

MH = Monoterpene hydrocarbons; OM = Oxygenated Monoterpenes;

SH = Sesquiterpene Hydrocarbons; OS = Oxygenated Sesquiterpenes.

Thirty two components were identified by GC/MS in C. myrrha oil, accounting for more than 68% of the whole oil. The C. myrrha essential oil mainly consists of oxygenated sesquiterpenes (Ca. 21.35%), followed by sessquiterpene hydrocarbons (Ca. 10.01%), oxygenated monoterpenes (2.98%) and monoterpene hydrocarbons (0.18%).

The main components were the C16H18O2 (42.68%), the oxygenated sesquiterpene, isofurano-germacrene (21.02%), C14H14O2 (13.59%) and 8,8-Dimethyl-1,9-methylene – 1,5-cycloundecadiene (3.81%). Some other components were only characterized but not identified (Ca. 32%).

Extracts prepared from C. molmol resins were analyzed by GC/MS. Twenty two terpenoid compounds were identified in the hexane extract of the resin. Among them, 2-acetoxyfuranodiene (9.80%), furanoeudesma-1,3-diene 8.97%, isofuranogermacrene 6.71%, epicurzerenone 3.64%, 2-methoxyfuranodiene 2.97% and lindestrene 2.74% were the main compounds from the myrrha resin, Tamar Ltd). Furanoeudesma-1,3-diene 20.59%, isofuranogermacrene 17.94%, 2-acetoxyfuranodiene 8.80% , 2-methoxyfuranodiene 7.33% and lindestrene 6.24% from myrrha resin , Pamir Ltd. [9]. The major constituents of the essential oil identified from the resin of C. myrrha by Mohammed et al., [10] were alpha- elemene, 7-isopropyl-1,4-dimethyl-2-azulenol, curzerne, germacra-1(10)7,11-trien-15-oic acid and 8,12-epoxy-6-hydroxy-C-lactone. Volatile concentrates from the oleo-gum resin of C. myrrha was isolated by supercritical extraction with carbon dioxide. It is main components, identified and quantified by GC/MS were furanoeudesma-1,3-diene, lindestrene, curzerene and germacrone [11]. Chemical analysis of essential oil from resin of Myrrha shows that the resin is rich in sesquiterpenes and sesquiterpene lactones compounds that possess anti-inflammatory and antitumor activity [12].

4. Conclusion

Analysis of C. myrrha resin oil in this study is an attempt to gain a better understanding of the secondary metabolite profile of this important valuable plant species.

Acknowledgement

We thank Department of Chemistry, Ministry of Science and Technology, Central Laboratory, Khartoum, Sudan, for the GC/MS facilities.


References

  1. EL-Egami AA, Burham BO and EL-KamaliHH. Essential oil composition of the flowering aerial parts of Sudanese Morettiaphillaeana (Del.) DC.Current Research Journal of Biological Sciences. 2011. 3(2):100-103.
  2. EL-KamaliHHet al.,.Chemical constituents of the volatile oil of Cyperusrotundus L. from Central Sudan.Journal of the Faculty of Science and Technology (JFST). 2011. Issue No. 2.
  3. Burham BO, EL-KamaliHH, EL-Egami AA. Volatile components of the resin of Pistacialentiscus "Mistica" used in Sudanese Traditional Medicine .Journal of Chemical and Pharmaceutical Research. 2011. 3(6):478-482.
  4. EL-kamaliHH, Burham BO, EL-EgamiAA .Analysis of the essential oil from fruits of Croton zambesicusMuel. Arg. Growing in Southern Kordofan , West Sudan. Natural Products Research Bulletin. 2012. 1(1): 1-6.
  5. Ramadan MM, Abdel GaderNN, EL-KamaliHH, GhanemKZ, Farrag AH. Volatile compounds and antioxidant activity of the aromatic herb Anethumgraveolens .Journal of the Arab Society for Medical Research. 2013. 8: 79-88.
  6. Tucker, A.O. Frankincense and Myrrh. Economic Botany. 1986. 40:425-433.
  7. British Pharmacopoea (BP). Vol. 2. HM Stationery Office: London. 1993 A- 154.
  8. Adam, R.P. Identification of essential oil components by Gas Chromatography/ Mass Spectrometry. Allured Publishing Corp., 2001.Illinois, USA.
  9. Hanus L O, Rosenthal D, Rezanka T, Dembitsky V M, Moussaief A. Fast and easy GC/MS identification of myrrha resins. Pharmaceutical Chemistry Journal. 2005. 42(12):719-720.
  10. Mohammed AA, Ali SI, EL-Baz FK, Hegazy AK, Kord MA. Chemical composition if essential oil and in vitro antioxidant and antimicrobial activities of crude extracts of Commiphora myrrha resin. Industrial Crops and Products. 2014. 57:10-16.
  11. Scorciapino A. Chemical composition of the essential oil and supercritical CO2 extract of Commiphora myrrha (Nees)Engl. And of Acorus calamus L. J.Agric Food Chem. 2005. 53(20):7939-43.
  12. AbdelGadir S, Ahmed IM. Commiphora myrrha and Commiphora africana essential oils. Journal of Chemical and Pharmaceutical Research. 2014. 6(7):151-156.

Article Tools
  Abstract
  PDF(179K)
Follow on us
ADDRESS
Science Publishing Group
548 FASHION AVENUE
NEW YORK, NY 10018
U.S.A.
Tel: (001)347-688-8931