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JMPS 2017; 5(1): 261-265
© 2017 JMPS
Department of Chemistry,
Faculty of Sciences, Federal
Nasarawa State, Nigeria.
Department of Chemistry,
Faculty of Natural Sciences
University of Jos, Jos-Nigeria.
Plateau State, Nigeria.
Faculty of Sciences, Federal
Nasarawa State, Nigeria.
Introduction: Syzygium guineense leaf and bark of are used for the treatment of tuberculosis, chronic
diarrhea, cough, dysentery, malaria, amenorrhea, wounds, ulcers, rheumatism and infections.
Material and Method: The various compounds in the n-hexane extract of the leaf were analysed by
TLC and identified by GC-MS technique. The TLC results indicated that four (4) terpenes are present in
hexane extracts of the leaf of Syzygium guineense after treating TLC plates with vanillin-Conc.H
methylethenyl)azulene(2.06%), caryophyllene oxide(3.86%), myristic acid (2.11%), n-hexadecenoic acid
(11.94%), 9-octadecanoic acid (25.72%), tetratriacontane (31.45%), 1,2-benzenedicarboxylic acid
(2.71%), tetratriacontane (6.70%) and pentatriacontane (3.95%). These compounds fall into three classes;
terpene/terpenoids, organic acids and hydrocarbons with the major compounds been the organic acids
42.48%. Hydrocarbons constituent 42.1% of the extract while only 0.38% constitute terpenes/terpenoids.
agent as anti-inflammatory analgesic, antipyretic and platelet-inhibitory actions.
Syzygium guineense leaf, TLC, GC-MS, Terpenes.
Plants are described as “nature’s chemical factories” which may contain natural substances
that exhibit bioactive properties by producing a definite physiological action on the human
body when administered
. Such derived compounds are reported to be less toxic and even
anti-malarials known to date with quite a number awaiting investigation
. Isolating and
. In some cases the crude extract is more effective pharmacologically
compounds with other compounds present in seems to add to pharmacological activity
Natural products introduces new chemical entities of wide structural diversity that will are
sources are yet to be fully tapped from planktonic organisms to mammals. Intensive research is
still needed through concerted cooperation to explore the biological activity of all sources of
natural products as core scaffolds for future drugs
. New approaches to drug discovery, such
important role of natural products in drug discovery
tuberculosis, chronic diarrhea, cough, dysentery, malaria, amenorrhea, wounds, ulcers,
rheumatism and infections. The investigation involves extracting the leaves with organic
solvents, concentrating the extracts, thin layer chromatography (TLC) analysis of the extracts,
and spectra analysis using hyphenated technique of gas chromatography-mass spectrometry
(GC-MS). This work seeks to establish a scientific basis for the application of Syzygium
dicotyledon which grows to a height of 8 – 15 metres
. In Africa, the plant is distributed in
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Namibia, Uganda, Swaziland, Cameroon, and South Africa.
dialect such as afour (Afizere/Jarawa), molmol (Hausa) and
ori (Yoruba). The root, bark and leaf are used in traditional
medicine as remedy for various ill health conditions. A
mixture of water and powder made from the bark and roots of
the plant when administered act as a purgative
treatment of stomach ache
. Syzygium guineense extract is
upsets can also be remedied by using this plant
activity and anti-diarrheal activity in tested organisms
The aqueous extract exhibited antibacterial activity against
caryophyllene oxide, cadinene, viridiflorol, epi-α- cadinol,
caryophyllene and humulene
. Betulinic acid, oleanolic
arjunolic acid, asiatic acid, terminolic acid, 6-hydroxyasiatic
acid, arjunolic acid 28-glucopyranosyl ester and the asiatic
Arabinogalactan polysaccharide was isolated from the Malian
caryophyllene oxide (7%), δ-cadinene (7.5%), viridiflorol
(7.5%), epi-α-cadinol (9.8%), α-cadinol (12.7%), cis-
calamenen-10-ol (14%), citronellyl pentanoate (15.2%), β-
caryophyllene (20.1%) and α-humulene (39.5%)
(2α,3β,4α) olean-11-en-28 oic acid and asiatic acid
(Hydroxyasiatic acid) were also isolated and they show
antibacterial activity against B. subtilis, E. coli and Shigella
oic acid isolated from the same plant were also antibacterial
activity against Planchonia careya and Enterococcus
The plants of the Family Myrtaceae are dicotyledonous
angiosperm shrubs and trees found in the tropics, sub-tropics
and temperate Australia
. They are characterised by radially
(petals) and numerous stamens
. The sepals and petals
flower (as with the eucalypts)
. The fruit is usually a berry
closely 150 genera in this family. The total number of species
seems to be disputable as different literature report gives
different number of species
. However within Myrtaceae,
widespread compared to the other species. Phytochemically,
several members of this family mainly accumulate flavonoids,
tannins, other phenolic derivatives and Terpenoids
compositae, matricaria, Labiatae, menthe spp; Myrtaceae,
compositions of terpenes can be markedly different from one
species to another
in terpenoids for antibacterial, antineoplastic, and other
range of distribution than the other myrtaceous genera since
they are frequently grown as exotics in commercial
. Members of this genus are used in folk
antirheumatic, anti-inflammatory, cleansing agents and are
also known to be effective in reducing blood cholesterol
Majority of the plants are also known to produce essential
oils, most of which are bacteriostatic, fungistatic, anti-
inflammatory and antifungal activities and as such used in
creams, soaps and toothpastes
analyzed by GC-MS majorly contains atractylone and
curzerene. It’s essential oils are active towards gram-positive
bacteria, Streptococcus equi and Staphylococcus epidermis
Plinia trunciflor leaf contains α-cadinol, apiole and cubenol
positive Streptococcus equi and Staphylococcus epidermis
In P. cattleianum, the most prominent compound is
constituent most Psidium species. Where variations exist in
oil content and composition, it is attributable to factors related
to ecosystem, the environment (temperature, relative
humidity, irradiance and photoperiod), genetics, chemotypes
and the nutritional status of the plant
genera Eugenia and Eucalyptus (Myrtaceae)
Syzygium australe and Syzygium leuhmannii are widespread
Australia and Africa
. The use of these plants as medicinal
meters from Myanmar and to Afghanistan and in other
countries like Thailand, Philippines and Madagascar
sub-Saharan Africa particularly Benin, Democratic Republic
of Congo and Cameroon to treat infectious diseases
been used in the treatment of pernicious attack, amenorrhea,
abdominal pain and diarrhea. This specie of Syzygium is also
distributed in Reunion Island, Central America (i.e.
Guatemala) and Asia (i.e. Malaysia, Nepal)
mountain slopes (altitude range from 800 to 2400 m) endemic
to Yunnan Province, in southwest of China
The family Myrtaceae is characterised by tannins and
flavonols as the main chemical constituents. The isolated
flavonoid, myricitrin seems to be the main flavonoid in this
family. This same flavonoid is present in Syzygium levinei and
Syzygium samarangense while (-)-epicatechol-3-O-gallate
was found from S. samarangens
. Furthermore, nilocitin,
present in Syzygium aromaticum. Similar flavonoids and
hydrolysable tannins ar contained in S. forrestii. Therefore,
the flavonoid glycoside myricitrin and the three hydrolyzable
tannins can serve as the chemosystematic markers of the
Methanol extracts of S. australe showed antimicrobial activity
gram-positive bacteria tested had their growth inhibited. The
leaf extract showed non-activity against Enterobacter
aerogenes, Escherichia coli, Salmonella salford, Bacillus
subtilis Candida albicans, Saccharomyces cerevisiae
extract displayed antifungal activity against a nystatin
resistant strain of A. niger but did not affect the growth of C.
albicans or S. cerevisiae
The major components in n-hexane extracts of Syzygium
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aromaticum identified using GC-MS are eugenol and eugenol
limonin and ferulic aldehyde along with eugenol while the
ethanol extract yielded the flavonoids tamarixetin 3-O-b-D-
glucopyranoside, ombuin 3-O-b-D-glucopyranoside and
quercetin which showed strong antioxidant activity against 1,
2-diphenyl picrylhydrazyl (DPPH)
.The leaf of Syzygium
such as quercetin, myricetin, myricetin 3-O-(4”-acetyl)-α-L-
rhamnopyranoside and galloyl carboxylase. The stem bark is
rich in the pentacyclic triterpenoid, betulinic acid, friedelin,
epi-firedenalol, β-sitosterol, eugenin and fatty acid ester of
epi-fierdanalol, quercetin, kaempferol, myrecitin, gallic acid,
bergenins and ellagic acid. These phytochemicals are also
reported present in the flower of Syzygium cumini
Pharmacological studies on activities of Syzgium cumini
revealed that it is gastro-protective, anti-ulcerogenic, anti-
inflammatory, hypoglycemic, a ntioxidant hypolipidaemic,
anti-anaemic, antibacterial, and radio-protective
flowers are rich in kaempferol, quercetin myricetin-
(quercetin-3-glucoside), myricetin-3-L-arabinoside, quercetin-
3-D-galactoside, dihydromyricetin, oleanolic acid, acetyl
oleonolic acid and eugenol
glycosides. One of the varieties found in Brazil possesses
malvidin-3-glucoside and petunidin-3-glycoside. The purple
colour of the fruit is due presence of one or two cyanidin
the actual colour the express on the plant depends on the pH.
The fleshy pericarp contains sterol
glycoside, oleanolic acid, betulinic acid and friedelin are main
constituents of Syzgium cumini L. The medicinal value of the
plant was attributed to malic acid, oxalic acid and gallic acid.
The leaf contains essential oils with pleasant odour which
contains limonene, dipentene (20%), sesquiterpenes of
cadalane type (40%), and sesquiterpenes of azulene type
(10% or less) with yield and physical characteristics of the oil
varying according to the season of collection
component of the essential oil appears to be triterpene
hydroxyl acid, oleanolic acid
ellagic acid, gallic acid, a glycoside- jamboline, starch,
myricyl alcohol in the unsaponified fraction of seeds and a
small quantity (0.05%) of pale yellow essential oil
Djipa et al reported that different studies between 1982 and
extracts of S. jambos Guatemala leaf possess anti-
inflammatory activity while the ethanol extract showed
. Myricetin and quercetin-3-O-β-D-
from the active extracts
. The methanol extract of the leaf
methylellagic acid. Ellagitannins (pedunculagin, casuarinin,
tellimagrandin I, strictinin, casuarictin, and traces of
tellimagrandin II) were detected, as in several other
Myrtaceae, in the extract of S. jambos from Japan
area in Jos Plateau state, Nigeria in August, 2012. The plant
was authenticated at Federal College of Forestry, Jos and a
herbarium sample deposited with voucher number FHJ 0947
in the herbarium. The leaves of the plant were air dried under
shade and stored in an air tight container for subsequent use.
Crude extract of n-hexane was prepared by soaking 500grams
of coarsely pulverized leaf of the plant in 2 litres of n-hexane.
This mixture was intermittently agitated for 72 hours at room
temperature. After the 72 hours, the extract was decanted,
filtered and concentrated using a rotary evaporator to give
7.0grams of the crude n-hexane extracts and the yield
calculated and the n-hexane crude extract was kept in the
refrigerator for analysis.
2.3 TLC Analysis of Hexane Extract
TLC analysis of hexane extract was carried out in the solvent
The TLC analysis using 100% hexane didn’t resolve the
components. Analysis with Hex: EtOAc (2:1) gave three
components with R
values 0.13, 0.23 and 0.84 while Hex:
values of 0.07,
(3:1). After heating the plates for 5mins, five coloured
components were obtained with R
values of 0.06, 0.12, 0.19,
0.06, 0.12, 0.19 and 0.75 were
The crude n-hexane extract was analyzed using GC–MS-
QP2010 system (Shimadzu, Kyoto, Japan) with split mode
(1:0) and the purge flow of 3 mL/min. The injector
temperature was 250 ˚C. Helium with constant flow of 1.5
mL/min served as carrier gas. The oven was programmed at
the following rates; the initial temperature of the column was
80 ˚C (2 min hold) followed by 200 ˚C (4min hold) and
finally at 280 ˚C (5min hold). The mass spectrometer
conditions were as follows: electron impact ionization (EI);
interface temperature, 250 ˚C; ion source temperature, 200 ˚C;
the detector voltage, 1 kV; solvent delay, 1.5 min. All data
were obtained by collecting the full-scan mass spectra within
the scan range of m/z 30 – m/z 800 over 30min.
2.5 Identification of Phytocompounds
The chemical compositions of the hexane extract of S.
Mass Spectrometry while the mass spectra of the compounds
found in the extract was matched with the National Institute
of Standards and Technology (NIST) library along with other
libraries. The identity of the components in the extract was
assigned by comparing their retention indices and mass
spectra fragmentation patterns with those stored in the
computer library. Interpretation of Mass-Spectrum was
conducted using the database of National Institute Standard
and Technology (NIST) having 191, 436 general compounds
and the Wiley library containing 310, 000 general
compounds. The spectrum of the unknown was compared
with the spectrum of known components stored in the NIST
libraries and were used for matching the identified
components from the plant material. The name, molecular
weight and structure of the components of the tested samples
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3. Results and Discussion
The extraction using n-hexane yielded 1.4% of the leaf
extract. The TLC analysis showed four terpenes are present in
the extract when plates were treated with vanillin-
coloured components were obtained with R
values of 0.06,
values of the four
compounds may likely be corresponding with the compounds
1-ethyl-2-methylbenzene, Ylangene, decahydro-4a-methyl-1-
methylethenyl)azulene and caryophyllene oxide not necessary
in that order, thereby asserting the relationship between the
two chromatographic methods employed for the analysis.
The studies on the principles in the leaf of Syzygium
showed the presence of twelve compounds. The compounds,
their structures, class and concentration are presented in
Tables 1, 2 and 3.
Table 3: Organic Acids and Fatty Acids Identified in the Leaf of
(Elaidic acid) C
(Pthalic acid) C
The compounds identified by the mass spectroscopy are
of Syzygium aromaticum identified using GC-MS are eugenol
and eugenol acetate, the major components in Syzygium
components in the n-hexane extracts are n-hexadecenoic acid
(11.94%), 9-octadecanoic acid (25.72%) and tetratriacontane
(31.45%). The other nine (9) components put together makes
up only 26.42% and these are 1-ethyl-2-methylbenzene
methylethenyl)azulene (2.06%), caryophyllene oxide(3.86%),
myristic acid (2.11%), 1,2-benzenedicarboxylic acid (2.71%),
tetratriacontane (6.70%) and pentatriacontane (3.95%). This
study is reporting two acids present in the leaf of syzygium
are myristic acid and 1,2-benzenedicarboxylic acid.
inflammatory actions as well as analgesic, antipyretic, and
platelet-inhibitory actions. It acts by blocking the synthesis of
prostaglandins by inhibiting cyclooxygenase. One mechanism
by which it does this is through inhibition of prostaglandin
synthesis and this account for their analgesic, antipyretic, and
platelet-inhibitory actions. Myristic acid is active in 7 of 711
bioassays, elaidic acid in 2 of 11, palmitic acid is 21 in 381,
pthalic acid active in 3 of 645 bioassays. Tetratriacontane is
inactive in 6 tested bioassays. The results of this study offer a
basis of using S. guineense as an alternative medicinal agent.
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In the present study twelve (12) phytochemical constituents
have been identified from hexane extract of Syzygium
Gas Chromatogram Mass spectrometry (GC-MS) analysis.
The presence of the various compounds particularly the
bioactive ones i.e. azulene, tetradecanoic acid (myristic acid),
and trans-octadec-9-enoic acid (elaidic acid) justifies the use
of the leaf against various ailments by traditional
The immense contribution of Prof. (Mrs.) E. A. Adelakun of
Chemistry Department, University of Jos, Jos-Nigeria is
Authours have declared that no competing interests exist.
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