<?xml version="1.0" encoding="UTF-8"?><!DOCTYPE article  PUBLIC "-//NLM//DTD Journal Publishing DTD v3.0 20080202//EN" "http://dtd.nlm.nih.gov/publishing/3.0/journalpublishing3.dtd"><article xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" dtd-version="3.0" xml:lang="en" article-type="research article"><front><journal-meta><journal-id journal-id-type="publisher-id">OALibJ</journal-id><journal-title-group><journal-title>Open Access Library Journal</journal-title></journal-title-group><issn pub-type="epub">2333-9705</issn><publisher><publisher-name>Scientific Research Publishing</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="doi">10.4236/oalib.1104230</article-id><article-id pub-id-type="publisher-id">OALibJ-82814</article-id><article-categories><subj-group subj-group-type="heading"><subject>Articles</subject></subj-group><subj-group subj-group-type="Discipline-v2"><subject>Biomedical&amp;Life Sciences</subject><subject> Business&amp;Economics</subject><subject> Chemistry&amp;Materials Science</subject><subject> Computer Science&amp;Communications</subject><subject> Earth&amp;Environmental Sciences</subject><subject> Engineering</subject><subject> Medicine&amp;Healthcare</subject><subject> Physics&amp;Mathematics</subject><subject> Social Sciences&amp;Humanities</subject></subj-group></article-categories><title-group><article-title>
 
 
  Bioactive Constituents of Methanol Extract of &lt;i&gt;Xylopia aethiopica&lt;/i&gt; (UDA) Fruits from Nsukka, Enugu State, Nigeria
 
</article-title></title-group><contrib-group><contrib contrib-type="author" xlink:type="simple"><name name-style="western"><surname>Innocent</surname><given-names>Uzochukwu Okagu</given-names></name><xref ref-type="aff" rid="aff1"><sup>1</sup></xref></contrib><contrib contrib-type="author" xlink:type="simple"><name name-style="western"><surname>Uchenna</surname><given-names>Ekpereamaka Ngwu</given-names></name><xref ref-type="aff" rid="aff1"><sup>1</sup></xref></contrib><contrib contrib-type="author" xlink:type="simple"><name name-style="western"><surname>Chinyere</surname><given-names>Jane Odenigbo</given-names></name><xref ref-type="aff" rid="aff1"><sup>1</sup></xref></contrib></contrib-group><aff id="aff1"><addr-line>Medical Biochemistry, Toxicology and Drug Discovery Unit, Department of Biochemistry, University of Nigeria, Nsukka, Nigeria</addr-line></aff><pub-date pub-type="epub"><day>02</day><month>03</month><year>2018</year></pub-date><volume>05</volume><issue>03</issue><fpage>1</fpage><lpage>11</lpage><history><date date-type="received"><day>3,</day>	<month>December</month>	<year>2017</year></date><date date-type="rev-recd"><day>2,</day>	<month>March</month>	<year>2018</year>	</date><date date-type="accepted"><day>5,</day>	<month>March</month>	<year>2018</year></date></history><permissions><copyright-statement>&#169; Copyright  2014 by authors and Scientific Research Publishing Inc. </copyright-statement><copyright-year>2014</copyright-year><license><license-p>This work is licensed under the Creative Commons Attribution International License (CC BY). http://creativecommons.org/licenses/by/4.0/</license-p></license></permissions><abstract><p>
 
 
  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.
 
</p></abstract><kwd-group><kwd>&lt;i&gt;Xylopia aethiopica&lt;/i&gt;</kwd><kwd> Bioactive Compounds</kwd><kwd> Gas Chromatography</kwd><kwd>  Mass Spectrometry</kwd><kwd> Methanol Extract</kwd></kwd-group></article-meta></front><body><sec id="s1"><title>1. Introduction</title><p>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 [<xref ref-type="bibr" rid="scirp.82814-ref1">1</xref>] . The analysis of the chemical constituents of these medicinal plants would be necessary in determining and isolating the active principles of these plants and hence, making way for the assessment of their biological activities. Currently, there are lots of techniques that can be employed to identify these constituents of plants such as chromatographic and spectroscopic techniques. A combination of gas chromatography (GC) and mass spectrometry (MS) has over the years proven to be one of the best combinational techniques in the identification of the chemical constituents of various plants. While gas chromatography separates the constituents, mass spectrometry helps to determine the molecular weight of these compounds [<xref ref-type="bibr" rid="scirp.82814-ref2">2</xref>] . The GC also separates volatile components in a sample while MS fragments the components and identifies them on the basis of their mass. Separation in GC is based on their boiling point where the substances with higher boiling point come out later and those with lower boiling point come out first. When they are out, they go into the MS which identifies them using their mass to charge ratio [<xref ref-type="bibr" rid="scirp.82814-ref3">3</xref>] . Xylopia aethiopica is a plant that is widely spread in the tropical Africa, especially in Ghana, Zambia, Mozambique and Angola. It is abundant in lowland rainforest and most fringe forest in the savanna zones of Nigeria [<xref ref-type="bibr" rid="scirp.82814-ref4">4</xref>] . It matures as a slim, tall tree of approximately 60 cm in diameter and up to 30 m high with a straight stem having a slightly stripped or smooth bark [<xref ref-type="bibr" rid="scirp.82814-ref5">5</xref>] . The taxonomical classification of Xylopia aethiopica includes:</p><p>Kingdom → Plantae</p><p>Subkingdom → Viridiplantae</p><p>Infra-kingdom → Streptophyta</p><p>Super-division → Embryophyta</p><p>Division → Tracheophyta</p><p>Subdivision → Spermatophytina</p><p>Class → Magnoliopsida</p><p>Superorder → Magnolianae</p><p>Order → Magnoliales</p><p>Family → Annonaceae</p><p>Genus → Xylopia L</p><p>Species → Xylopia aethiopica</p><p>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 [<xref ref-type="bibr" rid="scirp.82814-ref5">5</xref>] . [<xref ref-type="bibr" rid="scirp.82814-ref6">6</xref>] reported that fruits of the plant are used by herbalists for increasing menstrual flow and for terminating unwanted pregnancy. It is also added as a stimulant to several other herbal preparations in traditional medicine for treating stomach ache, bronchitis, dysentery, neuralgia and biliousness. Several biological activities such as promotion of prostaglandin synthesis [<xref ref-type="bibr" rid="scirp.82814-ref7">7</xref>] , hypertensive and diuretic effects as well as antimicrobial, antimalarial and anti-parasitic activities have been reported of the plant [<xref ref-type="bibr" rid="scirp.82814-ref8">8</xref>] . Some of the chemical constituents of this plant include resins, annonacin, reberoside, avicien, rebersole, alkaloids, tannin, oxalate and flavonoids [<xref ref-type="bibr" rid="scirp.82814-ref9">9</xref>] . Anonaceine, an alkaloid similar to morphine was found in the essential oil from X. aethiopica [<xref ref-type="bibr" rid="scirp.82814-ref10">10</xref>] . The antifertility effect of the plant has also been reported [<xref ref-type="bibr" rid="scirp.82814-ref8">8</xref>] . The plant has been shown to elevate intraocular pressure [<xref ref-type="bibr" rid="scirp.82814-ref11">11</xref>] , induce hepatic [<xref ref-type="bibr" rid="scirp.82814-ref12">12</xref>] and renal cell damages [<xref ref-type="bibr" rid="scirp.82814-ref13">13</xref>] , and decreases sperm quality [<xref ref-type="bibr" rid="scirp.82814-ref8">8</xref>] . The major bioactive components of X. aethiopica fruits varied based on the location of source [<xref ref-type="bibr" rid="scirp.82814-ref14">14</xref>] : that from Cameroun were β-phellandrene +1,8-cineole (31%), β-pinene (8%) and α-pinene (3.4%) [<xref ref-type="bibr" rid="scirp.82814-ref15">15</xref>] while that from Ivory Coast was β-pinene (20.56%) [<xref ref-type="bibr" rid="scirp.82814-ref16">16</xref>] . In Chad, the major constituents were α-pinene (5.56%), β-pinene (24.6%), β-phellandrene (12.36%) and α-phellandrene (7.16%) [<xref ref-type="bibr" rid="scirp.82814-ref17">17</xref>] . From Togo, α-pinene (23.6%), β-pinene (11%), sabinene (9.8%), germacrene D (8.3%) and 1,8-cineole (8.2%) were detected by [<xref ref-type="bibr" rid="scirp.82814-ref18">18</xref>] . In Sudan, the GC-MS results revealed the presence of monoterpenes (78.58%): monoterpene hydrocarbons (42.31%) and oxygenated monoterpenes (36.27%) and sesquiterpenes (18.85%): sesquiterpene hydrocarbons ((15.88%) and oxygenated sesquiterpenes (2.97%) [<xref ref-type="bibr" rid="scirp.82814-ref19">19</xref>] . It is also believed that solvent extraction affects the chemical content of plant materials; hence, this study was therefore designed to determine the bioactive compounds of methanol extract of Xylopia aethiopica fruits from Enugu State, Nigeria using gas chromatography-mass spectrometry (GC-MS) technique.</p></sec><sec id="s2"><title>2. Materials and Methods</title><sec id="s2_1"><title>2.1. Collection, Authentication and Extraction of Plant Material</title><p>The plant material used in this study, dried fruits of Xylopia aethiopica (<xref ref-type="fig" rid="fig1">Figure 1</xref>), was collected from Ogige Main-Market in Nsukka, Enugu State, Nigeria in the month of March, 2017. It was authenticated at the Herbarium of the Department of Plant Science and Biotechnology, University of Nigeria, Nsukka, Enugu State,</p><p>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.</p></sec><sec id="s2_2"><title>2.2. Determination and Identification of Bioactive Compounds in Methanol Extract of Xylopia aethiopica Fruits</title><p>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 &#215; 0.2 mm, 0.2 &#181;m 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.</p></sec></sec><sec id="s3"><title>3. Results</title>Bioactive Compounds in Methanol Extract of Xylopia aethiopica Fruits<p>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 <xref ref-type="table" rid="table1">Table 1</xref>. The GC-MS analysis of methanol extract of X. aethiopica fruits revealed fifty eight compounds representing 99% of the total extract and ten compounds representing only 1% unidentified. The major constituents 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%).</p><table-wrap-group id="1"><label><xref ref-type="table" rid="table1">Table 1</xref></label><caption><title> Bioactive compounds in methanol extract of Xylopia aethiopica fruits</title></caption><table-wrap id="1_1"><table><tbody><thead><tr><th align="center" valign="middle" >Peak No.</th><th align="center" valign="middle" >Retention Time</th><th align="center" valign="middle" >Area %</th><th align="center" valign="middle" >Identified compound</th></tr></thead><tr><td align="center" valign="middle" >1.</td><td align="center" valign="middle" >4.361</td><td align="center" valign="middle" >3.22</td><td align="center" valign="middle" >Terpineol, cis-β-terpineol cyclohexene, 1-methyl-3-(1-methylethenyl)</td></tr><tr><td align="center" valign="middle" >2.</td><td align="center" valign="middle" >4.533</td><td align="center" valign="middle" >1.07</td><td align="center" valign="middle" >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</td></tr><tr><td align="center" valign="middle" >3.</td><td align="center" valign="middle" >4.751</td><td align="center" valign="middle" >2.74</td><td align="center" valign="middle" >2,4,6-Octatriene, 2,6-dimethyl-, (E, Z), 2,4,6-Octatriene, 3,4-dimethyl-</td></tr><tr><td align="center" valign="middle" >4.</td><td align="center" valign="middle" >4.905</td><td align="center" valign="middle" >0.43</td><td align="center" valign="middle" >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)-</td></tr><tr><td align="center" valign="middle" >5.</td><td align="center" valign="middle" >5.019</td><td align="center" valign="middle" >0.34</td><td align="center" valign="middle" >Bicyclo [6.1.0] non-1-ene cyclohexanone, 5-methyl-2-(1-methylethlidene)-2-methyl-1-octen-3-yne</td></tr><tr><td align="center" valign="middle" >6.</td><td align="center" valign="middle" >5.088</td><td align="center" valign="middle" >0.37</td><td align="center" valign="middle" >2-(5-Aminohexyl) furan ethanone, 1-(methylenecyclopropyl) 3-Methylenecyclohexene</td></tr><tr><td align="center" valign="middle" >7.</td><td align="center" valign="middle" >5.174</td><td align="center" valign="middle" >1.69</td><td align="center" valign="middle" >3-cyclohexen-1-ol , 4-methyl-1-(1-methylethyl)-</td></tr><tr><td align="center" valign="middle" >8.</td><td align="center" valign="middle" >5.266</td><td align="center" valign="middle" >1.59</td><td align="center" valign="middle" >Cyclohexane, 1-methylene-3-(1-methylethyl)-, (R)-, 3 cyclohexene-1-methanol, α,α 4-trimethyl-, cyclohexene, 5-methyl-3-(1-methylethenyl) -, trans-(-)-</td></tr><tr><td align="center" valign="middle" >9.</td><td align="center" valign="middle" >5.317</td><td align="center" valign="middle" >0.44</td><td align="center" valign="middle" >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</td></tr><tr><td align="center" valign="middle" >10.</td><td align="center" valign="middle" >6.032</td><td align="center" valign="middle" >0.57</td><td align="center" valign="middle" >Benzenemethanol, 4-(1-methylehyl)</td></tr><tr><td align="center" valign="middle" >11.</td><td align="center" valign="middle" >6.484.</td><td align="center" valign="middle" >3.32</td><td align="center" valign="middle" >Cyclohexene, 4-ethynyl-4-methyl-3-(1-methylethenyl) -1-(1-methyethyl)-(3R-trans)-, (+)-4-Carene</td></tr><tr><td align="center" valign="middle" >12.</td><td align="center" valign="middle" >6.582</td><td align="center" valign="middle" >1.37</td><td align="center" valign="middle" >α-cubebene</td></tr><tr><td align="center" valign="middle" >13.</td><td align="center" valign="middle" >6.862</td><td align="center" valign="middle" >3.04</td><td align="center" valign="middle" >Copaene, α-Cubebenecopaene</td></tr><tr><td align="center" valign="middle" >14.</td><td align="center" valign="middle" >6.982</td><td align="center" valign="middle" >2.84</td><td align="center" valign="middle" >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-</td></tr><tr><td align="center" valign="middle" >15.</td><td align="center" valign="middle" >7.137</td><td align="center" valign="middle" >0.49</td><td align="center" valign="middle" >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</td></tr><tr><td align="center" valign="middle" >16.</td><td align="center" valign="middle" >7.303</td><td align="center" valign="middle" >5.53</td><td align="center" valign="middle" >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-</td></tr><tr><td align="center" valign="middle" >17.</td><td align="center" valign="middle" >7.406</td><td align="center" valign="middle" >3.76</td><td align="center" valign="middle" >(+)-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)</td></tr><tr><td align="center" valign="middle" >18.</td><td align="center" valign="middle" >7.537</td><td align="center" valign="middle" >2.34</td><td align="center" valign="middle" >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-</td></tr><tr><td align="center" valign="middle" >19.</td><td align="center" valign="middle" >7.640</td><td align="center" valign="middle" >2.65</td><td align="center" valign="middle" >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)-,</td></tr><tr><td align="center" valign="middle" >20.</td><td align="center" valign="middle" >7.709</td><td align="center" valign="middle" >0.79</td><td align="center" valign="middle" >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*)]-</td></tr><tr><td align="center" valign="middle" >21.</td><td align="center" valign="middle" >7.921</td><td align="center" valign="middle" >10.81</td><td align="center" valign="middle" >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</td></tr><tr><td align="center" valign="middle" >22.</td><td align="center" valign="middle" >8.046</td><td align="center" valign="middle" >1.10</td><td align="center" valign="middle" >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)</td></tr><tr><td align="center" valign="middle" >23.</td><td align="center" valign="middle" >8.109</td><td align="center" valign="middle" >1.78</td><td align="center" valign="middle" >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)</td></tr><tr><td align="center" valign="middle" >24</td><td align="center" valign="middle" >8.212</td><td align="center" valign="middle" >1.76</td><td align="center" valign="middle" >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)</td></tr></tbody></table></table-wrap><table-wrap id="1_2"><table><tbody><thead><tr><th align="center" valign="middle" >25.</th><th align="center" valign="middle" >8.247</th><th align="center" valign="middle" >2.47</th><th align="center" valign="middle" >Naphthalene, 1,2,3,5,6,8a-hexahydro-4,7-dimethyl -1-(1-methylethyl)-(1S-cis)</th></tr></thead><tr><td align="center" valign="middle" >26.</td><td align="center" valign="middle" >8.355</td><td align="center" valign="middle" >0.71</td><td align="center" valign="middle" >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</td></tr><tr><td align="center" valign="middle" >27.</td><td align="center" valign="middle" >8.395</td><td align="center" valign="middle" >0.34</td><td align="center" valign="middle" >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)]-</td></tr><tr><td align="center" valign="middle" >28.</td><td align="center" valign="middle" >8.521</td><td align="center" valign="middle" >2.57</td><td align="center" valign="middle" >Cyclohexanemethanol, 4-ethenyl-α,α, 4-trimethyl-3-(1-methylethenyl)-[1R-( 1α,3a, 4β)]</td></tr><tr><td align="center" valign="middle" >29.</td><td align="center" valign="middle" >8.573</td><td align="center" valign="middle" >0.59</td><td align="center" valign="middle" >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-</td></tr><tr><td align="center" valign="middle" >30.</td><td align="center" valign="middle" >8.807</td><td align="center" valign="middle" >0.43</td><td align="center" valign="middle" >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)-</td></tr><tr><td align="center" valign="middle" >31.</td><td align="center" valign="middle" >8.859</td><td align="center" valign="middle" >0.90</td><td align="center" valign="middle" >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)]</td></tr><tr><td align="center" valign="middle" >32.</td><td align="center" valign="middle" >8.928</td><td align="center" valign="middle" >0.46</td><td align="center" valign="middle" >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)</td></tr><tr><td align="center" valign="middle" >33.</td><td align="center" valign="middle" >9.156</td><td align="center" valign="middle" >1.14</td><td align="center" valign="middle" >4,4-Dimethyl-3-(3-methylbut-3-enylidene)-2-methylenbicyclo [4.1.0] heptanes, ledene oxide-(II), 8-Quinolinol, 4-methyl-</td></tr><tr><td align="center" valign="middle" >34.</td><td align="center" valign="middle" >9.254</td><td align="center" valign="middle" >0.49</td><td align="center" valign="middle" >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)-</td></tr><tr><td align="center" valign="middle" >35.</td><td align="center" valign="middle" >9.351</td><td align="center" valign="middle" >3.25</td><td align="center" valign="middle" >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</td></tr><tr><td align="center" valign="middle" >36.</td><td align="center" valign="middle" >9.431</td><td align="center" valign="middle" >0.48</td><td align="center" valign="middle" >Aromadendrene, cedren-13-ol, 8-thujopsene-13</td></tr><tr><td align="center" valign="middle" >37.</td><td align="center" valign="middle" >9.488</td><td align="center" valign="middle" >0.77</td><td align="center" valign="middle" >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-</td></tr><tr><td align="center" valign="middle" >38.</td><td align="center" valign="middle" >9.614</td><td align="center" valign="middle" >1.68</td><td align="center" valign="middle" >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)-</td></tr><tr><td align="center" valign="middle" >39.</td><td align="center" valign="middle" >9.877</td><td align="center" valign="middle" >0.60</td><td align="center" valign="middle" >Cycloisolongifolene, 8-hydroxy-, endo-, isolongifolene, 7,8-dehydro-8a-hydroxy-, 2-oxa-1,3-disilacyclohexane, 1,1,3,3,-tetramethyl-</td></tr><tr><td align="center" valign="middle" >40.</td><td align="center" valign="middle" >9.958</td><td align="center" valign="middle" >3.06</td><td align="center" valign="middle" >Cycloisolongifolene, 8,9-dehydro-Cycloisolongifolene, 8-hydroxy-, endo-, 10-oxatricyclo [4.2.1.1(3,9)] dec-4-ene, 9-ethenyl-</td></tr><tr><td align="center" valign="middle" >41.</td><td align="center" valign="middle" >10.221</td><td align="center" valign="middle" >0.37</td><td align="center" valign="middle" >7R, 8R-8-Hydroxy-4-isopropylidene-7-methylbicyclo [5.3.1]undec-1-ene, isolongifolene, 9,10-dehydro-Neoisolongifolene, 8,9-dehydro-</td></tr><tr><td align="center" valign="middle" >42.</td><td align="center" valign="middle" >10.427</td><td align="center" valign="middle" >0.45</td><td align="center" valign="middle" >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-</td></tr><tr><td align="center" valign="middle" >43.</td><td align="center" valign="middle" >10.581</td><td align="center" valign="middle" >0.46</td><td align="center" valign="middle" >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</td></tr><tr><td align="center" valign="middle" >44.</td><td align="center" valign="middle" >10.719</td><td align="center" valign="middle" >0.37</td><td align="center" valign="middle" >Cyclooctene, 4-methylene-6-(1-propenenylidene)-Isolongifolene, 7,8-dehydro-8a-hydroxy-4-(2-Nitrophenylimino)) -2-pentanon</td></tr><tr><td align="center" valign="middle" >45.</td><td align="center" valign="middle" >10.764</td><td align="center" valign="middle" >0.51</td><td align="center" valign="middle" >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-</td></tr><tr><td align="center" valign="middle" >46.</td><td align="center" valign="middle" >10.999</td><td align="center" valign="middle" >0.58</td><td align="center" valign="middle" >Aromadendrene oxide-(1), Alloaromadendrene oxide-(2) Glaucyl alcohol</td></tr><tr><td align="center" valign="middle" >47.</td><td align="center" valign="middle" >11.119</td><td align="center" valign="middle" >0.34</td><td align="center" valign="middle" >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</td></tr></tbody></table></table-wrap><table-wrap id="1_3"><table><tbody><thead><tr><th align="center" valign="middle" >48.</th><th align="center" valign="middle" >11.296</th><th align="center" valign="middle" >0.42</th><th align="center" valign="middle" >Benzeneethanol, 2-methoxy-α-methyl-(+)-2-carene, 4-α-isopropenyl-, Boldenone</th></tr></thead><tr><td align="center" valign="middle" >49.</td><td align="center" valign="middle" >11.428</td><td align="center" valign="middle" >0.41</td><td align="center" valign="middle" >(-)-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)-</td></tr><tr><td align="center" valign="middle" >50.</td><td align="center" valign="middle" >11.617</td><td align="center" valign="middle" >0.59</td><td align="center" valign="middle" >3-Heptadecene, (Z)-, 8-Heptadecene, n-Nonadecanol-1</td></tr><tr><td align="center" valign="middle" >51.</td><td align="center" valign="middle" >11.657</td><td align="center" valign="middle" >0.61</td><td align="center" valign="middle" >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</td></tr><tr><td align="center" valign="middle" >52.</td><td align="center" valign="middle" >12.510</td><td align="center" valign="middle" >2.62</td><td align="center" valign="middle" >n-Hexadecanoic acid</td></tr><tr><td align="center" valign="middle" >53.</td><td align="center" valign="middle" >13.179</td><td align="center" valign="middle" >0.63</td><td align="center" valign="middle" >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-</td></tr><tr><td align="center" valign="middle" >54.</td><td align="center" valign="middle" >13.499</td><td align="center" valign="middle" >3.59</td><td align="center" valign="middle" >Kaur-16-ene, Kaurene</td></tr><tr><td align="center" valign="middle" >55.</td><td align="center" valign="middle" >14.198</td><td align="center" valign="middle" >5.63</td><td align="center" valign="middle" >9,12-Octadecadienoic acid (z,z)-, 1-Hexadecyne</td></tr><tr><td align="center" valign="middle" >56.</td><td align="center" valign="middle" >14.358</td><td align="center" valign="middle" >0.58</td><td align="center" valign="middle" >Octadecanoic acid</td></tr><tr><td align="center" valign="middle" >57.</td><td align="center" valign="middle" >15.508</td><td align="center" valign="middle" >4.78</td><td align="center" valign="middle" >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</td></tr><tr><td align="center" valign="middle" >58.</td><td align="center" valign="middle" >16.263</td><td align="center" valign="middle" >3.08</td><td align="center" valign="middle" >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.</td></tr></tbody></table></table-wrap></table-wrap-group></sec><sec id="s4"><title>4. Discussion</title><p>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 [<xref ref-type="bibr" rid="scirp.82814-ref16">16</xref>] [<xref ref-type="bibr" rid="scirp.82814-ref20">20</xref>] . Also, the presence of these fatty acids and esters in the extract suggests that it can serve as a pesticide, an anti-androgenic flavor, and α-reductase inhibitor [<xref ref-type="bibr" rid="scirp.82814-ref21">21</xref>] . It can also serve as cancer preventive, [<xref ref-type="bibr" rid="scirp.82814-ref22">22</xref>] , hepatoprotective, antieczemic, hypocholesterolemic and anticoronary agent [<xref ref-type="bibr" rid="scirp.82814-ref23">23</xref>] . In traditional practice, the fruits are crushed and mixed with Shea butter and used as body creams or perfumes [<xref ref-type="bibr" rid="scirp.82814-ref5">5</xref>] . This is could be due to the presence of carboxylic acids such as octadecanoic acid and esters such as acetic acid, 6,6-dimethyl-2-methylene-7-(3-oxobutylidene) oxepan-3-yl methyl ester in the plant [<xref ref-type="bibr" rid="scirp.82814-ref23">23</xref>] . Xylopia aethiopica has been applied in traditional medicines as an effective antimicrobial agent [<xref ref-type="bibr" rid="scirp.82814-ref5">5</xref>] . This antimicrobial activity could be due to the presence of some aliphatic alcoholic compounds like octadiene-3-ol, which has earlier been shown to possess antimicrobial effects [<xref ref-type="bibr" rid="scirp.82814-ref24">24</xref>] . The compound, 1,6-cyclodecadiene, otherwise known as Germacrene D, was also identified by [<xref ref-type="bibr" rid="scirp.82814-ref25">25</xref>] . The compound is a class of volatile organic hydrocarbons, which plays a role as a precursor of various sesquiterpenes such as cadinenes and selinenes [<xref ref-type="bibr" rid="scirp.82814-ref26">26</xref>] . Reports showed that Germacrene D has insecticidal activity against mosquitoes [<xref ref-type="bibr" rid="scirp.82814-ref27">27</xref>] , antibacterial activity [<xref ref-type="bibr" rid="scirp.82814-ref28">28</xref>] , as well as repellent activity against aphids [<xref ref-type="bibr" rid="scirp.82814-ref29">29</xref>] and ticks [<xref ref-type="bibr" rid="scirp.82814-ref30">30</xref>] . [<xref ref-type="bibr" rid="scirp.82814-ref25">25</xref>] also detected the presence of spathulenol, an oxygenated sesquiterpene that has immunomodulatory effects, mosquito repellant activity, antimicrobial and anti-inflammatory activities [<xref ref-type="bibr" rid="scirp.82814-ref31">31</xref>] . This could be the reason why essential oil from the plant is used as mosquito and housefly repellents, and termite antifeedant in traditional practice [<xref ref-type="bibr" rid="scirp.82814-ref32">32</xref>] . Xylopia aethiopica has been reported to be of help in enhancing the healing of some ailments in man [<xref ref-type="bibr" rid="scirp.82814-ref33">33</xref>] and this may be associated with the presence of phenolic compounds such as 2-amino-3-hydroxy phenol as detected in extract in the present study and by [<xref ref-type="bibr" rid="scirp.82814-ref24">24</xref>] . Xylopia aethiopica has been used as flavour pepper and spice in food and for management of liver diseases [<xref ref-type="bibr" rid="scirp.82814-ref34">34</xref>] . This could be as a result of the compound, terpineol, cis-β-terpineol cyclohexene, 1-methyl-3-(1-methylethenyl) which is a citrus essential oil. Citrus essential oils could be considered suitable alternatives to chemical additives for use in various industrial areas such as food, cosmetics and pharmaceuticals. They also have an attractive and mild aroma that can mask food smells from fish, meat, garlic and onion. These seem to be positive functions for use as industrial antimicrobial agents such as preservatives. Cyclohexanones and cyclohexanols such as bicyclo [6.1.0]-non-1-ene-cyclohexanone, 5-methyl-2-(1-methylethlidene)-2-methyl-1-octen-3-yne, 3-cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)-, and others identified in the plant can be used as solvents for paints and dyes, in pesticides, and as an intermediate for pharmaceuticals, films, soaps, and coatings [<xref ref-type="bibr" rid="scirp.82814-ref35">35</xref>] . Naphthalene identified in the plant is said to be hazardous [<xref ref-type="bibr" rid="scirp.82814-ref36">36</xref>] . This could be the reason excessive consumption of the plant has been reported to be toxic [<xref ref-type="bibr" rid="scirp.82814-ref13">13</xref>] . This study has also shown the presence and amount of bioactive components in plant materials depend on the location of the plant source.</p></sec><sec id="s5"><title>5. Conclusion</title><p>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.</p></sec><sec id="s6"><title>Conflict of Interest</title><p>The authors declare no conflict of interest.</p></sec><sec id="s7"><title>Cite this paper</title><p>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</p></sec></body><back><ref-list><title>References</title><ref id="scirp.82814-ref1"><label>1</label><mixed-citation publication-type="other" xlink:type="simple">Ashokkumar, R. and Ramaswamy, M. (2014) Phytochemical Screening by FTIR Spectroscopic Analysis of Leaf Extracts of Selected Indian Medicinal Plants. International Journal of Current Microbiology and Applied Sciences, 3, 395-406.</mixed-citation></ref><ref id="scirp.82814-ref2"><label>2</label><mixed-citation publication-type="other" xlink:type="simple">Murugan, M. and Mohan, V.R. (2014) Phytochemical, FT-IR and Antibacterial Activity of Whole Plant Extract of Aerva lanata (L.) Juss. Ex. Schult. Journal of Medicinal Plants Studies, 2, 51-57.</mixed-citation></ref><ref id="scirp.82814-ref3"><label>3</label><mixed-citation publication-type="other" xlink:type="simple">Ashish, C., Manish, K.G. and Priyanka, C. 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