The bioactive compounds in methanol extract of Xylopia aethiopica fruits were determined using a combination of gas chromatography and mass spectrometry (GC-MS). The compound identification was based on the molecular structure, molecular mass and calculated fragments. Interpretation on mass spectrum of GC-MS analyzer (Hewlett Packard GC-MS system) was done using the database of National Institute Stan dard and Technology (NIST). The results showed different peaks representing the presence of about 58 bioactive compounds which are mainly carboxylic acids, esters, phenolic compounds and fatty acids. The most abundant bioactive compounds detected were 2,4,6-octatriene (2.74%), cyclohexanemethanol (2.57%), kaurene (3.59%), 9,12-octadecadienoic acid (5.63%), 1,6-cyclodecadiene (10.81%), terpineol (3.22%), cyclohexene (3.32%), copaene (3.04%), 1,6-cyclodecadiene (5.53%), 1-hexadecyne (5.63%) and silane (4.63%). The presence of these bioactive components suggests that the extract is of great pharmaceutical value.
Africa is blessed with lots of medicinal plants that contain active principles that make them useful to cure Man’s diseases. Medicinal plants are locally accepted because they are believed to have less or no side effects when compared to synthetic drugs. They are also available and cheap to obtain [
Kingdom → Plantae
Subkingdom → Viridiplantae
Infra-kingdom → Streptophyta
Super-division → Embryophyta
Division → Tracheophyta
Subdivision → Spermatophytina
Class → Magnoliopsida
Superorder → Magnolianae
Order → Magnoliales
Family → Annonaceae
Genus → Xylopia L
Species → Xylopia aethiopica
Xylopia aethiopica has been recorded to have so many medicinal and nutritional values such as treatment of sores, boils, cough, wounds and cuts, among others [
The plant material used in this study, dried fruits of Xylopia aethiopica (
Nigeria. The dried fruits were ground into powder using a mechanical grinder. The powdered sample (1000 g) was soaked in 4.5 litres of methanol (JHD, China) in an air-tight container and was left for 48 hours with occasional stirring. The suspension was filtered and the filtrate concentrated using a rotary evaporator under reduced pressure at 40˚C. The oily dark brown concentrate of percentage yield of 17.8% was subjected to GC-MS analysis.
The bioactive components of methanol extract of Xylopia aethiopica fruits were determined using a GC-MS analyzer (Hewlett Packard GC-MS system with Purge and Trap, US EPA 8260/5035 by GC/MSD and ASTM D2600/D2908). The fused silica HP-20 M polyethylene glycol column (50 m × 0.2 mm, 0.2 µm thickness) was directly coupled to the mass spectrometer. The carrier gas was helium (1 mL/min). The program used was 4 min isothermal. The injection port temperature was 250˚C and the detector temperature 280˚C. Mass spectra were taken at 70 eV; a scan interval of 0.5 s and fragments from 45 to 450 Da. The relative percentage amount of each component was calculated by comparing its average peak area to the total area. Software adopted to handle mass spectra and chromatograms was Turbomass version 5.2.0. Identification of the compounds were based on the molecular structure, molecular mass and calculated fragments. Interpretation of mass spectrum from GC-MS was conducted using the database of National Institute Standard and Technology (NIST) having more than 82,000 patterns. The name of each bioactive component of the extract was ascertained and the percentage amount of each was calculated by comparing its average peak area to the total area. The spectrum of unknown components was compared with the spectrum of the known components stored in the NIST library. This was done in order to determine whether this extract contains any individual compound or group of compounds, which may substantiate its ethno-medicinal applications.
The identities of the bioactive compounds in methanol extract of Xylopia aethiopica fruits were confirmed based on the peak area and retention time and presented in
Peak No. | Retention Time | Area % | Identified compound |
---|---|---|---|
1. | 4.361 | 3.22 | Terpineol, cis-β-terpineol cyclohexene, 1-methyl-3-(1-methylethenyl) |
2. | 4.533 | 1.07 | 1,6-Octadien-3-ol, 3,7-dimethyl-bicyclo [2.2.1] hept-2-ene, 2,7,7-trimethyl-1,6-Octadien-3-ol, 3,7-dimethyl |
3. | 4.751 | 2.74 | 2,4,6-Octatriene, 2,6-dimethyl-, (E, Z), 2,4,6-Octatriene, 3,4-dimethyl- |
4. | 4.905 | 0.43 | Tricycle [4.4.0.0(2,8)] dec-4-ene 1,3-cyclohexadiene, 5-(3-butene-1-γ 1), Bicyclo [3.1.0] hex-2-ene, 4-methylene-1-(1-methylethyl)- |
5. | 5.019 | 0.34 | Bicyclo [6.1.0] non-1-ene cyclohexanone, 5-methyl-2-(1-methylethlidene)-2-methyl-1-octen-3-yne |
6. | 5.088 | 0.37 | 2-(5-Aminohexyl) furan ethanone, 1-(methylenecyclopropyl) 3-Methylenecyclohexene |
7. | 5.174 | 1.69 | 3-cyclohexen-1-ol , 4-methyl-1-(1-methylethyl)- |
8. | 5.266 | 1.59 | Cyclohexane, 1-methylene-3-(1-methylethyl)-, (R)-, 3 cyclohexene-1-methanol, α,α 4-trimethyl-, cyclohexene, 5-methyl-3-(1-methylethenyl) -, trans-(-)- |
9. | 5.317 | 0.44 | Bicyclo [3.1.1] hept-2-ene-2-methanol, 6,6-dimethyl-, cis-bicyclo [3.3.0] oct-2-ene, BIcyclo (3.2.1) oct-2-ene |
10. | 6.032 | 0.57 | Benzenemethanol, 4-(1-methylehyl) |
11. | 6.484. | 3.32 | Cyclohexene, 4-ethynyl-4-methyl-3-(1-methylethenyl) -1-(1-methyethyl)-(3R-trans)-, (+)-4-Carene |
12. | 6.582 | 1.37 | α-cubebene |
13. | 6.862 | 3.04 | Copaene, α-Cubebenecopaene |
14. | 6.982 | 2.84 | 1H-cyclopropa [a] naphthalene, 1a,2,3,5,6,7,7a,7b-Octahydro-1,1,7,7a-tetramethyl-, [1aR-(1a α, 7α, 7aα, 7bα)]-, Bicyclo [4.4.0] dec-1-ene, 2-isopropyl-5-methyl-9-methylene- |
15. | 7.137 | 0.49 | 3H-3a, 7-Methanoazulene, 2,4,5,6,7,8-hexahydro-1,4,9,9-tetramethyl-,[3aR-(3aα, 4β, 7α), 3H-3a, 7-Methanoazulene, 2,4,5,6,7,8-hexahydro-1,4,9,9-tetramethyl-,[3aR-(3aα, 4β, 7α)] δ-selinene |
16. | 7.303 | 5.53 | 1,6-cyclodecadiene, 1-methyl-5-methylene-8-(1-methylethyl)-, [s-(E,E)]-1H-cyclopenta [1,3] cyclopropa[1,2] benzene, octahydro-7-methyl-3-methylene-4-(1-methyethyl)-, [3aS-(3aα, 3bβ, 4β, 7α, 7aS*)]-, Bicyclo [4.4.0] dec-1-ene, 2-isopropyl-5-methyl-9-methylene- |
17. | 7.406 | 3.76 | (+)-Epi-bicyclosesquiphellandrene 1H-cyclopenta [1,3] cyclopropa [1,2] benzene, octahydro-7-methyl-3-methylene-4-(1-methylethyl)-, [3aS-(3aα, 3bβ, 4β 7α, 7aS*)]-, Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-7-methyl-4-methylene-1-(1-methylethyl)-, 1α,4aβ, 8aα) |
18. | 7.537 | 2.34 | Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-7-methyl-4-methylene-1-(1-methylethyl)-, 1α,4aβ, 8aα)-, Bicyclo[4.4.0] dec-1-ene, 2-isopropyl-5-methyl-9-methylene- |
19. | 7.640 | 2.65 | Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-7-methyl-4-methylene-1-(1-methylethyl)-, 1α,4aβ, 8aα)-, Naphthalene, 1,2,4a,5,6,8a-octahydro-7-methyl-4-methylene-1-(1-methylethyl)-, |
20. | 7.709 | 0.79 | 1,6-cyclodecadiene, 1-methyl-5-methlylene-8-(1-methylethyl)-, [s-(E,E)]-, 1H-cyclopenta [1,3] cyclopropa [1,2] benzene, octahydro-7-methyl-3-methylene-4-(1-methylethyl)-, [3aS-(3aα, 3bβ, 4β,7α,7aS*)]- |
21. | 7.921 | 10.81 | 1,6-cyclodecadiene, 1-methyl-5-methlylene-8-(1-methylethyl)-, [s-(E,E)]-, 1H-cyclopenta [1,3] cyclopropa [1,2] benzene, octahydro-7-methyl-3-methylene-4-(1-methylethyl)-, [3aS-(3aα, 3bβ, 4β,7α,7aS*)]-, (+)-Epi-bicyclosesquiphellandrene |
22. | 8.046 | 1.10 | Bicyclo [4.4.0] dec-1-ene, 2-isopropyl-5-methyl-9-methylene-, (+)-Epi-bicyclosesquiphellandrene, Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-7-methyl-4-methylene-1-(1-methylethyl)-, 1α,4aα, 8aα) |
23. | 8.109 | 1.78 | Naphthalene, 1,2,4a,5,6,8a-hexahydro-4,7-dimethyl -1-(1-methylethyl)-, 1,6-cyclodecadiene, 1-methyl-5-methylene-8-(1-methylethyl)-, [s-(E,E)]-, Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-7-methyl-4-methylene-1-(1-methylethyl)-, 1α,4aα, 8aα) |
24 | 8.212 | 1.76 | Cyclohexene, 6-ethenyl-6-methyl-1-(1-methylethyl)-3-(1-methyethylidene)-, (S)-, Copaene, Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-7-methyl-4-methylene-1-(1-methylethyl)-, 1α,4aα, 8aα) |
25. | 8.247 | 2.47 | Naphthalene, 1,2,3,5,6,8a-hexahydro-4,7-dimethyl -1-(1-methylethyl)-(1S-cis) |
---|---|---|---|
26. | 8.355 | 0.71 | Naphthalene, 1,2,3,4,4a,7-hexahydro-1,6-dimethyl -4-(1-methylethyl)-, 1H-3a, 7-methanoazulene, 2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-[3R-(3α,3aβ, 7β,8aα)], α-cubebene |
27. | 8.395 | 0.34 | Naphthalene, 1,2,4a,5,6,8a-hexahydro-4, 7-dimethyl-1-(1-methylethyl)-, [1R-(1α,4aβ, 8aα)]-, Isoledene, Naphthalene, 1,2,3,5,6,7,8a-octahydro-1-8a-dimethyl-7-methylene-7-(1-methylethyl)-, [1R-(1α,7β, 8aα)]- |
28. | 8.521 | 2.57 | Cyclohexanemethanol, 4-ethenyl-α,α, 4-trimethyl-3-(1-methylethenyl)-[1R-( 1α,3a, 4β)] |
29. | 8.573 | 0.59 | 1H-Indene, 2,3-dihydro-2,2-dimethyl 4, 4-dimethyl-3-(3-methybut-3-enylidine)-2-methylenbicyclo [4.1.0] heptane, 1H-Indene, 2,3-dihydro-2,2-dimethyl 4, 4-dimethyl- |
30. | 8.807 | 0.43 | 1-Hydroxy-1, 7-dimethyl -4-isopropyl -2, 7-cyclodecadiene, Bicyclo [2.2.1] heptan-2-ol, 1,3,3-trimethyl-, acetate, (1S-exo)-, ethanone, 1-(2-methyl-2-cyclopenten-1-y1)- |
31. | 8.859 | 0.90 | Tricyclo [5.2.2.0 (1,6)] undecan-3-ol, 2-methylene-6,8,8-trimethly-, Tricyclo [4.4.0.0(2,7)] dec -3-ene-3-methanol, 1-methyl-8-(1-methylethyl)-, 1H-cycloprop [e] azulen-7-ol, decahydro-1,1,7-trimethyl-4-methylene-, [1ar-(1aα, 4aα, 7β, 7aβ, 7bα)] |
32. | 8.928 | 0.46 | 2-(4a,8-demethyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-2-yl)-prop-2-en-1-ol, Patchoulene γ Gurjunenepoxide-(2) |
33. | 9.156 | 1.14 | 4,4-Dimethyl-3-(3-methylbut-3-enylidene)-2-methylenbicyclo [4.1.0] heptanes, ledene oxide-(II), 8-Quinolinol, 4-methyl- |
34. | 9.254 | 0.49 | Cyclohexene, 6-ethenyl-6-methyl-1-(1-methyethyl)-3-(1-methylethylidene)-, (S)-, 4,7-Methanoazulene, 1,2,3,4,5,6,7,8-Octahydro-1,4,9,9-tetramethyl-[1S-(1α, 4α, 7α)], Naphthalene, 1,2,3,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S-cis)- |
35. | 9.351 | 3.25 | 1H-cycloprop[e]azulen-7-ol, decahydro-1,1,7-trimethyl-4-methylene-, [1ar-(1aα, 4aα, 7β,7aβ, 7bα)]-(-)-spathulenol, 1,7,7-Trimethyl-2-vinylbicyclo [2.2.1]hept-2-ene |
36. | 9.431 | 0.48 | Aromadendrene, cedren-13-ol, 8-thujopsene-13 |
37. | 9.488 | 0.77 | Aromadendrene oxide-(2), 2-(4a, 8-dimethyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-2-yl)-prop-2-en-1-ol, longipinocarveol, trans- |
38. | 9.614 | 1.68 | 1H-Indole-3-carboxylic acid, 4-hydroxy-,6-isopropenyl-4, 8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-ol, Naphthalene, 1,2,3,4-tetrahydro-1, 6-dimethyl-4-(1-methylthyl)-, (1S-cis)- |
39. | 9.877 | 0.60 | Cycloisolongifolene, 8-hydroxy-, endo-, isolongifolene, 7,8-dehydro-8a-hydroxy-, 2-oxa-1,3-disilacyclohexane, 1,1,3,3,-tetramethyl- |
40. | 9.958 | 3.06 | Cycloisolongifolene, 8,9-dehydro-Cycloisolongifolene, 8-hydroxy-, endo-, 10-oxatricyclo [4.2.1.1(3,9)] dec-4-ene, 9-ethenyl- |
41. | 10.221 | 0.37 | 7R, 8R-8-Hydroxy-4-isopropylidene-7-methylbicyclo [5.3.1]undec-1-ene, isolongifolene, 9,10-dehydro-Neoisolongifolene, 8,9-dehydro- |
42. | 10.427 | 0.45 | Benzoic acid, 2-amino-3-hydoxy-phenol, 4-methyl-2-nitro-thiourea, N-ethyl-N’-tricyclo[3.3.1.1 (3,7)]dec-1-yl- |
43. | 10.581 | 0.46 | Tricycle [4.4.0.0(2,7)] dec-3-ene-3-methanol, 1-methyl-8-(1-methylethyl)-, calarene epoxide 1-(3,3-Dimethyl-1-1-yl)-2,2-dimethylcyclopropene-3-carboxylic acid |
44. | 10.719 | 0.37 | Cyclooctene, 4-methylene-6-(1-propenenylidene)-Isolongifolene, 7,8-dehydro-8a-hydroxy-4-(2-Nitrophenylimino)) -2-pentanon |
45. | 10.764 | 0.51 | 1H-cycloprop[e]azulen-7-oL, decahydro-1,1,7-trimethyl-4-methylene-, [1ar-(1aα, 4aα,7β, 7bα)], acetic acid, 6,6-dimethyl-2-methylene-7-(3-oxobutylidene) oxepan-3-yl methyl ester, isolongifolene, 7,8-dehydro-8a-hydroxy- |
46. | 10.999 | 0.58 | Aromadendrene oxide-(1), Alloaromadendrene oxide-(2) Glaucyl alcohol |
47. | 11.119 | 0.34 | 2-Butenal, 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, 2-(4a,8-dimethyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-2-yl)-prop-2-en-1-ol, isoaromadendrene epoxide |
48. | 11.296 | 0.42 | Benzeneethanol, 2-methoxy-α-methyl-(+)-2-carene, 4-α-isopropenyl-, Boldenone |
---|---|---|---|
49. | 11.428 | 0.41 | (-)-Neoclovene-(I), dihydro-1H-Cycloprop[e]azulene, decahydro-1,1,4,7-tetramethyl-, [1aR-(1aα, 4β, 4aβ,7β,7aβ,7bα)], 1-cyclohexene, 1,3,3-trimethyl-2-(1-methylbut-1-en-3-on-l-yl)- |
50. | 11.617 | 0.59 | 3-Heptadecene, (Z)-, 8-Heptadecene, n-Nonadecanol-1 |
51. | 11.657 | 0.61 | δ-Gurjunenepoxide-(2), 9-isoprop-yl-1-methyl-2-methylene-5-oxatricyclo [5.4.0.0 (3,8)] undecanecyclohexane, 1,5-diethenyl-3-methyl-2-methylene-, (1α,3α,5α |
52. | 12.510 | 2.62 | n-Hexadecanoic acid |
53. | 13.179 | 0.63 | 1H-Naphtho[2,1-b]pyran, 3-ethenyldodecahydro-3, 4a,7,7,10a-pentamethyl-, [3R-(3α,4aβ,6aα,10aβ,10bα)], 1H-Naphtho[2,1-b]pyran, 3 ethenyldodecahydro-3 , 4a,7,7,10a-pentamethyl-, [3S-(3α,4aα,6aβ,10aα,10bβ)], Acetamide, N-(3-methylphenyl)-2-phenylthio- |
54. | 13.499 | 3.59 | Kaur-16-ene, Kaurene |
55. | 14.198 | 5.63 | 9,12-Octadecadienoic acid (z,z)-, 1-Hexadecyne |
56. | 14.358 | 0.58 | Octadecanoic acid |
57. | 15.508 | 4.78 | Silane, dimethyl (3-methylbut-2-enyloxy) heptyloxy-, Galaxolide 1 (3E, 5E, 7E)-6-Methyl-8-(2.6.6-trimethyl-1-cyclohexenyl) -3,5,7-octatrien-2-one |
58. | 16.263 | 3.08 | Naphthalene, decahydo-1,1, 4a-trimethyl-6-methylene-5-(3-methylene-4-pentenyl)-, [4aS-(4aα, 5α,8aβ)], Benz [c] acridine, 7,9-demethyl-3-Methyl-1-phenyl-2-azafluorene. |
This study demonstrated the usefulness of GC-MS as a valuable tool for the identification of bioactive compounds present in plant materials. The analysis of the methanol extract of X. aethiopica fruits revealed the presence of 58 bioactive compounds. Among the identified compounds, the presence of fatty acids like n-hexadecanoic acid, 9,12-octadecanoic acid, hexadecanoic acid and methyl ester may be associated with the reported antioxidant property of the plant [
The present study identified 58 bioactive compounds in the methanol extract of Xylopia aethiopica fruits using gas chromatography-mass spectrometry (GC-MS). This plant has many bioactive compounds that possess antioxidant, anti-inflammatory, anti-microbial and anticancer properties. This showed that the plant extract should be of great pharmaceutical interest. Haven identified many bioactive compounds in methanol extract of Xylopia aethiopica fruits in the present study, and it is recommended that the active ingredients are isolated and subjected to further tests to compare their usefulness in the prevention and treatment of various conditions.
The authors declare no conflict of interest.
Okagu, I.U., Ngwu, U.E. and Odenigbo, C.J. (2018) Bioactive Constituents of Methanol Extract of Xylopia aethiopica (UDA) Fruits from Nsukka, Enugu State, Nigeria. Open Access Library Journal, 5: e4230. https://doi.org/10.4236/oalib.1104230