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 American Journal of  
Food Science and Technology (AJFST)

Identification of  Bioactive Compounds in Chrysobalanus icaco Seed Kernel Using Gas 
Chromatography-Mass Spectrometry

Oganezi N. C.1*, Agbaeze T.1, Kalu S. O.1

Volume 3 Issue 1, Year 2024
ISSN: 2834-0086 (Online)

DOI: https://doi.org/10.54536/ajfst.v3i1.2365
https://journals.e-palli.com/home/index.php/ajfst

Article Information ABSTRACT

Received: February 12, 2024
Accepted: March 17, 2024
Published: March 21, 2024

Chrysobalanus icaco seed kernel (i.e Cocoplum) is good source of  oil and is utilized as spice in 
soups or stews in some African cuisines. The work aimed to identify compounds in methanol 
and dichloromethane/methanol (1:1, v/v) flour extract from its seed kernels using gas 
chromatography-mass spectrometry. Eleven compounds were identified from the methanol 
extract while thirteen compounds were identified from the dichloromethane/methanol 
extract. The most abundant compounds from the methanol extract were cis-13-octadecenoic 
acid methyl ester, cis vaccenic acid and n-Hexadecanoic acid. They had relative abundance of  
28.83, 17.14 and 15.40% respectively. 2,6-octadienal-3,7-dimethyl (E) (ie α-citral), citral, cis-
3-hexenyl cis-3-hexenoate and trans-2,7-dimethyl-4,6-octadiene-2-ol were the most abundant 
in the dichloromethane/methanol extract. These had relative abundance of  12.86, 18.92, 
10.56 and 20.59% respectively. Compounds which were common to both methanol and 
dichloromethane/methanol extracts of  C. icaco seed kernel were 2,6-octadienal-3,7-dimethyl 
(E), hexadecanoic acid methyl ester, n-Hexadecanoic acid, heptadecanoic acid, 16 methyl, 
methyl ester, cis-vaccenic acid and oleic acid. Both solvents extracted varied concentrations 
of  compounds which fall in different classes of  either being an unsaturated long chain 
aldehyde, fatty acids, fatty acid methyl esters, indene derivatives, monoterpenoid alchohol. 
The compounds identified in both extracts of  Chrysobalamus icaco seed kernels have various 
beneficial bioactivities and sensory attributessuch as being flavor compounds which confers 
C.icaco seed kernel a peculiar aroma. As such, Chrysobalamus icaco seed kernel is a functional 
food and can serve as a good raw material for edible oil from which bioactive compounds can 
be isolated and utilized in relevant food systems and in the preparation of  neutraceuticals and 
pharmaceuticals. Therefore, its use in cuisines is greatly encouraged.   

Keywords

Chrysobalanusicaco, Seed Kernel, 
Gas Chromatography-Mass 
Spectrometry, Bioactive Compounds, 
Extracts

1 Department of  Food Science and Technology, Abia State University, Uturu, Abia State, Nigeria
* Corresponding author’s e-mail: chinonyeremwog@yahoo.com

INTRODUCTION
A spice is dried seed, fruit, root, bark or flower of  a plant 
or a herb used in small quantities for flavor, color or as 
a preservative (Kunnumakkara et al., 2009). Herbs and 
spices have been utilized as additives globally not only 
to enhance the sensory attributes of  food, but also to 
increase shelf  life of  foods by reducing or eliminating 
food borne pathogens (Lai and Roy, 2004). Spices can 
perform functions as nutrient sources, antioxidants, 
preservatives, insecticides and as medicinal plants for 
human use (Fasoyiro, 2015). Besides adding flavor 
and taste to dishes, they help prevent and alleviate 
various health problems due to the presence of  various 
bioactive compounds which have different physiological 
and biochemical functions. Spices have shown many 
health benefits in preventing and curing a number of  
diseases such as cancer, aging, metabolic, neurological, 
cardiovascular and inflammatory diseases (Gottardi et 
al., 2016). The active phytochemicals derived from these 
spices have provided the molecular basis for these actions 
(Kunnumakkara et al., 2009). 
Chrysobalanus icaco (Cocoplum) belongs to the family 
Chrysobalanaceae (Burkill, 1985). It is a low shrub or bushy 
tree which grows near sea beaches and inland throughout 
tropical Africa, tropical America, the Caribbean, southern 
Florida and the Bahamas (KWCSP,2023). It grows fruit 
for which its pulp and seed are consumed as food. The 

seed’s kernel is utilized as soup spice either as pepper 
soup spice or ‘ofeakwu’ (ie palm fruit) soup spice in some 
parts of  West Africa. The seed kernel is ground into a 
fine flour/powder and used as spice. C. icaco, commonly 
called ‘gbafilo’ seeds are economically and medicinally 
important as they are utilized for the preparation of  
special soup, control blood pressure, malaria fever and 
treatment of  stomach disorder (Davies and Zibokere, 
2011).In some climes, where it is common C. icaco plays 
a role in traditional medicine (Presta et al., 2007). De 
Aguiar et al.(2017) reported that the seeds can produce an 
edible oil and they identified the types of  fats using gas 
chromatography. Vargas et al. (2010) identified essential 
oil from the leaves of  C. icaco after supercritical fluid 
extraction using gas chromatography. 
Many bioactive compounds have been extracted from 
spices, providing a scientific basis for the use of  such 
spices in our diet (Kunnumakkara et al., 2009). The 
development of  equipment and methods for identifying 
and evaluating natural products bioactive compounds 
to ensure their quality and discover new drugs is very 
necessary (Fu et al., 2019). So many naturally synthesized 
compounds have bioactive functions and are being 
explored for different applications, particularly in the 
food and pharmaceutical industry (do’ Nascimento et al., 
2021). Gas chromatography – mass spectrometry analysis 
is a convenient method to test the quantitative amount 



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of  bioactive compounds in plant extracts (Gomathi et al., 
2015). There is death of  information on C. icaco  seeds but 
a good number of  research work has been done on leaf  
extracts and fatty acids of  oil extract from the leaves and 
seeds. It is in view of  this that gas chromatography mass 
spectrometry analysis was carried out on methanol and 
dichloromethane/methanol (1:1,v/v) extracts of  whole 
seed flour of  Chroysobalanus icaco.   

MATERIALS AND METHODS
Sourcing of  Materials and Extraction of  Bioactive 
Compounds
Chrysobalanus icaco seeds were sourced from Afor Oru 
market, Oru Ahiara in Ahiazu Mbaise in Imo State, 
Nigeria. They were cracked to remove the husk and 
free the seed kernel. After which, the seed kernels were 
washed in clean water, drained off  water, air dried before 
milling to get fine flour. The resultant Chrysobalanus icaco 
seed kernel flour was used for the extraction of  bioactive 
compounds using methanol and dichloromethane/
methanol (1:1, v/v). To extract the bioactive compounds, 
twenty (20) grams of  the pulverized flour was dispensed 
into two different labelled conical flasks. Two hundred 
(200) mL absolute methanol and dichloromethane/
methanol (1:1, v/v) were dispensed into the two different 
conical flasks respectively. The sample mixtures were 
shaked vigorously on a vortex mixer for 30mins and 
covered using aluminium foil. They were allowed to stand 
for 24h at room temperature and subsequently filtered 
through No1 Whatman filter paper respectively. Each 
sample extract was concentrated by heating over a boiling 
water bath to remove excess solvent. Hence, two extracts 
from whole seed flour of  Chrysobalanus icaco were obtained. 
These extracts were subjected to gas chromatography/ 
mass spectrometry (GC-MS) analysis for the separation 
and identification of  compounds. 

Gas Chromatography Mass Spectrometry Analysis  
(GC–MS) 
The GC–MS analysis of  bioactive compounds from the 
two extracts were done using Agilent Technologies GC 
systems with GC-7890A/MS-5975C model (Agilent 
Technologies, Santa Clara, CA, USA) equipped with 
HP- 5MS column (30 m in length × 250 μm in diameter 
× 0.25 μm in thickness of  film). Helium gas (99.995%) 
was used as carrier gas with flow rate of  1 mL/min. The 
initial column temperature was set at 50 –150 °C with 
increasing rate of  3 °C/min and hold time of  10 min. 
Finally, the temperature was increased to 300 °C at 10 
°C/min. One microliter (1μl) of  each extract was diluted 
with respective solvents and injected in a splitless mode 
into the gas chromatogram using hamilton syringe. 
The injector temperature was 250ºC while the mass 
spectrometer ion source temperature was 200ºC with 
an interface temperature of  280ºC but with electron 
impact ionization energy of  70 eV. Total run time of  
the gas chromatography-mass spectrometry analysis for 
the methanol extract was 20mins for both extracts. The 

relative abundance of  the chemical compounds present 
in each extract was expressed as percentage based on 
peak area normalization produced in the chromatogram. 
Compounds were identified by mass spectroscopy. 
Bioactive compounds in the different extracts were 
identified based on GC retention time on HP-5MS 
column and matching of  the spectra with computer 
software data of  standards by comparing retention indices 
and mass fragmentation patterns of  the compounds with 
those stored in the computer library software of  the 
National Institute of  Standard Technology (NIST/EPA/ 
NIH, Mass Spectral Library, Version 2.0). Quantitative 
determinations were made by relating respective peak 
areas to TIC areas of  the GCMS. 

RESULTS AND DISCUSSION
Table 1 shows results on methanol extract of  
Chrysobarlanus icaco seed kernel. Results indicated the 
presence of  eleven compounds. The most abundant 
compounds were cis-13-octadecenoic acid methyl ester, 
cis- vaccenic acid, hexadecanoic acid methyl ester, and 
n-hexadecanoic acid. They had relative abundance of  
28.83, 17.14, 16.40 and 15.40% respectively. These 
compounds have been reported to have various biological 
activities and nutritional values. Cis-13-octadecenoic acid 
methyl ester is a fatty acid methyl ester with therapeutic 
uses in medicine and surgery (Awonyemi et al., 2020). 
Cisvaccenic acid is a monounsaturated n -7 fatty acid 
and is reported to have antibacterial and hypolipidemic 
effects in rats (Hamazakiet al., 2016). Cis-vaccenic acid 
may have multiple modes of  activity such as antioxidant 
activity which involves the neutralization of  free radicals 
hence reducing oxidative stress, it may serve as an anti-
inflammatory agent by decreasing the production of  
cytokines that promote inflammation; it may also act as 
a transcription factor regulating the expression of  genes 
that are involved in metabolic processes (Aimola et al, 
2016., Rontani et al, 2003). Hexadecanoic acid methyl 
ester was reported to have bactericidal effect against 
multi drug resistant bacteria (Shaaban et al., 2021). It 
has other biological activities such as anti-inflammatory, 
hypocholesterolemic, cancer preventive, hepatoprotective, 
nenaticid, insectifuge, antihistaminic, anticorona, and 
anti antiarthritic properties (Jegadeeswariet al., 2012). 
n-Hexadeanoic acid has been reported to posses 
antioxidant, antimicrobial and anti-inflammatory activities 
(Siswadi and Saragih, 2021). 
Other bioactive compounds found in significant 
quantities in the methanol extract of  C. icaco seed 
with well documented biological, physiological and 
pharmacological activities are oleic acid (6.02%) 
heptadecanoic acids, 16-methyl methylester (6.43%) and 
2,6-octadienal-3,7-dimethy (E) (i.eα-citral). Oleic acid 
has been reported to induce apoptosis in carcinoma 
cells via the activation of  different intracellular pathways 
involved in carcinoma cell development which could be 
the main mechanism of  its antitumoreffects reported in 
clinical studies (Carrilo et al., 2012) Heptadecanoic acid, 



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Am. J. Food. Sci. Technol. 3(1) 13-18, 2024

16-methyl, methyl ester is a branched fatty acid methyl 
ester . It was reported to have the best activity against 
skin cancer protein and is considered for further in vitro 
studies towards development of  anti skin cancer drug 
(Saravanakumar et al., 2012). 2,6- octadienal – 3,7-dimethy 
(E) is reported to be a major component of  lemon grass, 

volatile oil of  Cymbopogon, atratus or of  C. flexuosus. It has 
a role as a flavoring agent, a fragrance, an insecticide and 
aldehyde oxidase inhibitor (Aiemsaard et al., 2011). It 
was reported to be suitable acaricidal and mite indicator 
ingredient and can be used for the control of  dust mites 
(Park and Lee, 2018). 

Table 1: Results on Gas Chromatography -Mass Spectrometry analysis of  methanol extract of  Chrysobalamusicaco 
(Cocoplum)seed kernel
Peak 
number

Retention 
time (mins)

Compound name Relative 
abundance (%)

Molecular 
formular

Molecular 
weight

1 7.081 10-Undecen-4-one-2,2,6,6, tetramethyl 2.43 C15H28O 224.38
2 7.691 2,6-Octadienal 3.7-dimethyl ester (E) 4.35 C10H16O2 152.23
3 16.993 Hexadecanoic acid methyl ester 16.40 C17H34O2 270.45
4 17.641 n-Hexadecanoic acid 15.40 C16H32O2 256.42
5 18.808 Cis-13-Octadecanoic acid, methyl ester 28.83 C19H36O2 296.49
6 18.974 Furamic acid, pent-4-en-2-yl tridecyl ester 0.89 C22H38O4 366.53
7 19.050 Heptadecanoic acid, 16-methyl,  methyl ester 6.43 C19H38O2 298.50
8 19.448 Cis-vaccenic acid 17.14 C18H34O2 282.46
9 19.647 Oleic acid 6.02 C18H34O2 282.47
10 19.697 12-methyl-E,E-2,13-Octadecadien-1-ol 0.44 C19H36O 280.41
11 19.799 1H-Indene,2-butyl-5-hexyloctahydro- 0.52 C19H36 264.49

Table 2 shows results on the compounds present in 
dichloromethane/methanol extract of  Chrysobalamusi 
caco seed kernel. The most abundant compounds were 
2,6-octadienal – 3,7-dimethyl (i.e α-citral),citral, Cis-
3- hexehyl-cis-3-hexenoate and trans-2,7-dimethyl-4,6- 
octadiene-2-ol. They had relative abundance of  12.86, 
18.92, 10.56 and 20.59% respectively. These compounds 
have been reported to have beneficial biological 
activities. In addition to already mentioned biological 
activities2, 6-octadienal-3,7-dimethyl and citral are similar 
compounds. Citral is anacyclic monoterpene aldehyde 
which consists of  a racemic mixture of  two isomers 
namely geranial and neral (Ganjewala et al., 2012). It has 
biological activities  such as antimicrobial, antioxidant, 

anticancer, antidiuretic and anti-inflammatory (Shama 
et al., 2021). Cis-3-hexeny, cis -3-hexenoate is a flavor 
compound which has a fruity aroma and flavor and is 
widely used in the food industry as a flavor and fragrance 
ingredient (JECFA FAO/ WHO, 1997). Trans-2,7-
dimethyl-4,6-octadiene-2-ol is a monoterpeniod alchohol. 
It has anti-inflammatory, antimicrobial, anticonvulsant, 
antiviral, antioxidant, anti-diabetic activity and also 
improves the functions of  the endocrine system (Uju et al, 
2022).9,7-octadecadienal, (Z) is an unsaturated long chain 
aldehyde which is reported to have antioxidant, anti-
inflamatory activities (Geraci et al., 2017, Adeoye-Isijola., 
et al., 2018) as well as antimicrobial property(Karthika and 
Paulsamy, 2014). 

Figure 1: Chromatograph of  Methanol extract of  Chrysobalanusicaco (Cocoplum) seed kernel



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Minor components were found in Chysobalanus icaco 
seed kernel for both extracts and they have important 
biological activities because of  their synergistic effects 
based on several studies that have identified them from 
other sources. Compounds common to both extracts were 
2,6-octadienal – 3,7-dimethyl(i.e α-citral), hexadecanoic 
acid methyl ester, n-Hexadecanoic acid, heptadecanoic 

acid-16- methyl, methyl ester, cis -vaccenic acid and oleic 
acid. Oleic acid is the most commonly occurring fatty acid 
in nature and its high content in olive oil is responsible 
for the hypotensive effect observed in olive oil (Ayed et 
al., 2018). This suggests that the presence oleic acid in 
Chysobalanus icaco seed kernel will proffer hypotensive 
activity in human biological system.

Table 2: Gas Chromatography and Mass Spectrometry analysis of  bioactive compounds from Dichloromethane/ 
methanol extract of  Chrysobalanus icaco (Cocoplum) seed kernel 
Peak 
number

Retention 
time (mins)

Compound name Relative 
abundance (%)

Molecular 
formular

Molecular 
weight

1 7.067 2.6-Octadienal,3,7-Dimethyl 12.86 C10H16O 152.23
2 7.691 Citral 18.92 C10H16O 152.23
3 9.103 Cis-3-Hexenyl-cis-3-Hexenoate 10.56 C12H20O2 196.29
4 9.767 Trans-2,7-Dimethyl 4,6-Octadien-2-ol 20.59 C10H18O 154.25
5 11.693 3.8.11-Trioxotetracyclo [4.4.1.0 (2,4). 

0(7.9)] Undecane (1 α, 2 α, 4 α, 6 α, 7β, 9β)
3.08 C8H10O3 154.16

6 12.544 3-Hexene, 2-methyl-(2) 3.48 C7H14 98.19
7 16.982 Hexadecanoic acid, methyl ester 3.75 C17H34O2 270.45
8 17.631 n-Hexadecanoic acid 5.39 C16H32O2 256.42
9 18.809 Cis-Vaccenic acid 4.93 C18H34O2 282.46 
10 18.972 6,11- Dimethyl-2,6,10-dodecatrien-1-ol 2.77 C14H24O2 208.34
11 19.041 Heptadecanoic acid,16-methyl-methyl ester 2.49 C19H38O2 298.50
12 19.431 9,7 Octadecadienal 7.75 C18H32O 264.45
13 19.605 Oleic acid 2.33 C18H34O2 282.47
14 20.087 Oleic acid 1.09 C18H34O2 282.47

Figure 2: Chromatograph of  Dichloromethane/methanol extract of  Chrysobalanus icaco (Cocoplum) seed kernel

CONCLUSION
The seed kernel of  Chysobalanus icaco fruit which is used 
as seed spice in some African cuisines contains beneficial 
bioactive phytochemicals with documented beneficial 
activities. These compounds have activities which serve as 
flavor compounds that proffer the seed spice its peculiar 
aroma, while some of  the compounds found in substantial 
quantities are reported to promote good health via having 
antioxidant activities, anti-inflammatory, bactericidal 

effect, anticancer, antidiuretic effects to mention but a 
few. Hence, Chrysobalanus icaco (ie Cocoplum) seeds used 
as spice for culinary is a functional ingredient that can 
be beneficial in promoting good health by preventing 
degenerative diseases. 

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