Sains Malaysiana 48(5)(2019):
999–1009
http://dx.doi.org/10.17576/jsm-2019-4805-08
GC-MS Analysis of Chemical Constituents
and in vitro Antioxidant Activity of the Organic Extracts
from the Stem of Bridelia
stipularis
(Analisis GC-MS Juzuk Kimia dan Aktiviti Antioksidan
Ekstrak Organik
secara in vitro daripada
Batang Bridelia stipulari)
SAMINA KHAN
YUSUFZAI1,
MOHAMMAD
SHAHEEN
KHAN2*,
EUNICE
LUA
HANRY2,
MOHD.
RAFATULLAH1
& BELSHEERA BINTI ELISON2
1School of Industrial
Technology, Universiti Sains
Malaysia, 1180 Minden, Pulau Pinang,
Malaysia
2Industrial Chemistry
Programme, Faculty of Science and
Natural Resources, Universiti Malaysia
Sabah, 88400 Kota Kinabalu, Sabah, Malaysia
Received: 29 August
2018/Accepted: 27 February 2019
ABSTRACT
In the present study the stems
of the Bridelia stipularis (L.) Blume, which is traditionally used by ethnic
communities in Sabah, Malaysia, has been investigated for its
chemical composition, total flavonoid content (TFC) and total phenolic content
(TPC)
via Gas-Chromatography-Mass Spectroscopy (GC-MS)
analysis consuming hexane, chloroform and ethyl acetate as extraction
solvents and gallic acid and quercetin
as internal standards. In vitro antioxidant activity
(AA) was determined by the application of 1,1-diphenyl-2-picryl
hydrazine (DPPH) radical scavenging assay using tert-butyl-1-hydroxytoluene
(BHT) as comparative drug. The
GC-MS
profiling showed the presence of 1-dodecanol (40.917%),
oxalic acid, cyclobutyl octadecyl
ester (24.985%), 1-octanol,2-nitro (12.424%), benzaldehyde,
2,4-dimethyl- (9.583%), 4-tridecanol (6.359%) and nitric acid,
nonyl ester (5.616%) as major constituents.
The TPC (224.62
± 0.08 mg QE/g) and TFC (160.48 ± 0.08 mg GAE/g)
was reported highest for the most polar solvent i.e. ethyl acetate.
The in vitro antioxidant study disclosed highest IC50 value
for ethyl acetate (2.15 mg/mL), queued by chloroform (1.19 mg/mL)
and hexane (0.89 mg/mL), displaying that polar solvents are
good extraction solvents for the identification of free radical
scavenging properties, TFC and
TPC.
Keywords: Antioxidant activity;
GC-MS; medicinal plants; total flavonoid content; total
phenolic content
ABSTRAK
Dalam kajian terbaharu, batang Bridelia stipularis (L.), Blume secara
tradisi digunakan oleh etnik pribumi
di Sabah, Malaysia, telah dikaji
kerana komposisi
kimia, kandungan jumlah flavonoid (TFC) dan
jumlah (kandungan
fenolik KUHP) melalui
analisis Gas Jisim
Spektroskopi Kromatografi (GC-MS)
menggunakan heksana,
kloroform dan etil
asetat sebagai
pengekstrakan pelarut, asid galik dan
Quercetin sebagai piawai
dalaman. Aktiviti antipengoksida (AA) in vitro ditentukan oleh aplikasi hidrazina 1,1-difenil-2-
pikril (DPPH) radikal
menghapus-sisa cerakin
menggunakan tert-butil-1-hidroksitoluen (BHT)
sebagai perbandingan dadah. GC-MS pemprofilan
mendedahkan kehadiran
1-dodekanol (40.917%), asid oksalik,
ester oktadekil cyclobutyl
(24.985%), 1-oktanol,2-nitro (12.424%), benzaldehid,
2,4-dimetil-(9.583%), 4-tridekanol (6.359%) dan
asid nitrik, ester nonil (5.616%) sebagai juzuk utama. Dalam
TPC
(224.62 ± 0.08 mg QE/g) dan
TFC
(160.48 ± 0.08 mg GAE/g) dilaporkan
tertinggi bagi
pelarut paling terkutub iaitu etil asetat.
Kajian antioksidan
in vitro dinyatakan
nilai50 IC
tertinggi untuk
etil asetat (2.15 mg/mL), diikuti oleh kloroform
(1.19 mg/mL) dan heksana
(0.89 mg/mL), menunjukkan kutub
pelarut yang baik
pengekstrakan pelarut bagi pengenalpastian sifat radikal skaveng,
TFC
dan TPC.
Kata kunci: Aktiviti
antioksidan; GC-MS; jumlah kandungan fenolik; jumlah kandungan flavonoid; tumbuhan perubatan
REFERENCES
Afify, A.E., El-Beltagi, H.S., El-Salam, S.M.
& Omran, A.A. 2012. Biochemical
changes in phenols, flavonoids, tannins, vitamin E, β-carotene
and antioxidant activity during soaking of three white sorghum
varieties. Asian Pac. J. Trop. Biomed. 2: 203-209.
Ahmad,
N., Fazal, H., Abbasi,
B.H. & Farooq, S. 2010. Efficient free radical scavenging
activity of Ginkgo biloba, Stevia rebaudiana and
Parthenium hysterophorous
leaves through DPPH (2, 2-diphenyl-1-picrylhydrazyl). Int.
J. Phytomed. 2: 231-239.
Ainsworth,
E.A. & Gillespie, K.M. 2007. Estimation of total phenolic
content and other oxidation substrates in plant tissues using
Folin-Ciocalteu reagent. Nat. Protoc.
2: 875- 877.
Altemimi, A., Lakhssassi,
N., Baharlouei, A., Watson, D.G. &
Lightfoot, D.A. 2017. Phytochemicals: Extraction, isolation
and identification of bioactive compounds from plant extracts.
Plant 6: 42-63.
Anjum, A., Haque, M.R., Rahman, M.S., Hasan, C.M., Haque,
M.E. & Rashid. M.A. 2011. in vitro antibacterial,
antifungal and cytotoxic activity of three Bangladesh Bridelia
species. Int. Res. Pharm.
Pharmacol. 1: 149-154.
Aparna,
V., Dileep, K.V., Mandal, P.K., Karthe,
P., Sadasivan, C. & Haridas,
M. 2012. Anti- inflammatory property of N-hexadecanoic
acid: Structural evidence and kinetic assessment. Chem. Biol.
Drug. Des. 80: 434-439.
Arthur, H.R. 1954.
A phytochemical survey of some plants of North Borneo. J.
Pharm. Pharmacol. 6: 66-72.
Azmir, J., Zaidul, I.S., Rahman, M.M., Sharif, K.M., Mohamed, A., Sahena, F., Jahurul, M.H., Ghafoor, K., Norulaini, N.A. &
Omar, A.K. 2013. Techniques for extraction of bioactive compounds
from plant materials: A review. J. Food Eng. 117: 426-436.
Bondet, V., Brand-Williams,
W. & Berset, C. 1997. Kinetics
and mechanisms of antioxidant activity using the DPPH free radical
method. LWT-Food Sci. Technol. 30: 609-615.
Brand-Williams, W.,
Cuvelier, M.E. & Berset,
C.L. 1995. Use of a free radical method to evaluate antioxidant
activity. LWT-Food Sci. Technol. 28: 25-30.
Chandrakasan, L. & Neelamegam, R. 2011. In vitro studies on antioxidants
and free radical scavenging activities in the extracts of Loranthus longiflorus
desr. bark samples obtained from two host trees. J. Phytol.
3: 22-30.
Chowdury, K., Sharma, A.,
Kumar, S., Gunjan, G.K., Nag, A. &
Mandal, C.C. 2017. Colocynth extracts prevent epithelial to
mesenchymal transition and stemness of breast cancer cells. Front. Pharmacol. 8: 593-606.
Cuvelier, M.E. & Richard,
H. 1992. Mesure de l’efficacite
des antioxygenes d’origine
vegetale. Recherche des composes
actifs de la sauge. These en Sciences Alimentaires. ENSIA,
Massy. pp. 64-71.
De-Monte, C., Carradori, S., Granese, A., Di-Pierro, G.B., Leonardo, C. & De-Nunzio,
C. 2014. Modern extraction tecniques
and their impact on the pharmacological profile of Serenoa
repens extracts for the treatment of lower urinary tract
symptoms. BMC Urol. 14: 63-68.
Dhawan, D. & Gupta,
J. 2017. Comparison of different solvents for phytochemicals
extraction potential from Datura
metel plant leaves. Int. J.
Biol. Chem. 11: 17-22.
Douglas, B. &
Kiang, A.K. 1957. A phytochemical survey of Malaya. Malayan
Pharm. J. 6: 1-16.
Fialkov, A.B., Steiner,
U., Jones, L. & Amirav, A. 2006.
A new type of GC-MS with advanced capabilities. Int. J. Mass
Spect. 251: 47-58.
Firdous, S.M. 2014. Phytochemicals
for treatment of diabetes. EXCLI J. 13: 451-453.
Fujita, N., Saito,
Y., Ito, T., Mizuguchi, H., Endo,
M. & Ogata, T. 2012. Folin-Chiocalteu
colorimetric analysis using a scanner for rapid determination
of total polyphenol content in many test samples. Stud. Sci.
Technol. 1: 139-144.
Halim, A.A., Jawan, J.A., Ismail, S.R., Othman, N. & Masnin, M.H. 2013. Traditional knowledge and environmental
conservation among indigenous people in Ranau,
Sabah. Global J. Human-Soc. Sci. Res. 13: 5-11.
Harman-Ware, A.E.,
Sykes, R., Peter, G.F. & Davis, M. 2016. Estimation of terpene
content in loblolly. Front. Energy Res. 4: 16-20.
Ho, C.T. 1992. Phenolic
compounds in food and their effects on health II. ACS Symposium
Series 507: 87-97.
Huang, D.J., Ou, B.X. & Prior, R.L. 2005. The chemistry behind antioxidant
capacity assays. J. Agric. Food Chem. 53: 1841- 1856.
Jamal, J.A. 2006.
Malay Traditional Medicine. Tech Monitor (Special Feature:
Traditional Medicine: S & T Advancement). pp. 37-49.
Johnsen, S.J., Dahl-Jensen,
D., Gundestrup, N., Steffensen,
J.P., Clausen, H.B., Miller, H., Masson-Delmotte,
V., Sveinbjörnsdottir, A.E. &
White, J. 2001. Oxygen isotope and palaeotemperature
records from six Greenland ice-core stations: Camp Century,
Dye-3, GRIP, GISP2, Renland and NorthGRIP. J. Quater. Sci. 16: 299-307.
Kahkonen, M.P., Hopia, A.I., Vuorela, H.J., Rauha, J.P., Pihlaja, K., Kujala, T.S. & Heinonen, M.
1999. Antioxidant activity of plant extracts containing phenolic
compounds. J. Agr. Food Chem. 47:
3954-3962.
Katewa, S.S., Chaudhary,
B.L. & Jain, A. 2004. Folk herbal medicines from tribal
area of Rajasthan, India. J. Ethnopharmacol.
92: 41-46.
Kathriarachchi, H., Hoffmann, P.,
Samuel, R., Wurdack, K.J. & Chase,
M.W. 2005. Molecular phylogenetics
of Phyllanthaceae inferred from five
genes (plastidatpB, matK, 3’ndhF, rbcL, and nuclear
PHYC). Mol. Phylogenetics Evol.
36: 112-134.
Kedare, S.B. & Singh,
R.P. 2011. Genesis and development of DPPH method of antioxidant
assay. J. Food Sci. Technol. 48: 412-422.
Khan, M.S., Yusufzai, S.K., Kaun, L.P., Shah,
M.D. & Idris, R. 2016. Chemical composition and antioxidant
activity of essential oil of leaves and flowers of Alternanthera
sessilis red from Sabah. J.
App. Pharm. Sci. 6: 157-161.
Khan, M.S., Yusufzai, S.K., Kimin, L. &
Jabi, N.A. 2018. Determination of chemical composition, total
flavonoid content, total phenolic content and antioxidant capacity
of various crude extracts of Manihot
esculenta crantz leaves. IJRASET.
6: 2433-2443.
Kodoh, J., Mojiol, A.R., Lintangah, W., Gisiu, F., Maid, M. & Liew,
K.C. 2017. Traditional knowledge of the uses of medicinal plants
among the ethnic communities in Kudat,
Sabah, Malaysia. Int. J. Agr. Forest.
Planta. 5: 79-85.
König, W.A. & Hochmuth, D.H. 2004. Enantioselective gas chromatography in
flavor and fragrance analysis: Strategies for the identification
of known and unknown plant volatiles. J. Chromatogr.
Sci. 42(8): 423-439.
Krishnaiah, D., Sarbatly, R. & Nithyanandam,
R. 2011. A review of the antioxidant potential of medicinal
plant species. Food Bioprod. Process.
89: 217-233.
Krishnan, K.S. 1992.
The Useful Plants of India. New Delhi, India: Council
of Scientific & Industrial Research. pp. 86-87.
Kulip, J. 2003. An ethnobotanical
survey of medicinal and other useful plants of Muruts in Sabah, Malaysia. Telopea
10: 81-98.
Li, X., Wu, X. &
Huang, L. 2009. Angelicaesinensis
(Danggui). Molecules 14: 5349-5361.
Malenčić, D., Popović, M. & Miladinović,
J. 2007. Phenolic content and antioxidant properties of soybean
(Glycine max (L.) Merr.) seeds.
Molecules 12: 576-581.
Mall, T.P. &
Tripathi, S.C. 2017. Diversity of wild nutrimental fruits
of District Bahraich, Uttar Pradesh,
India. Int. J. Curr. Res. Biosci.
Plant Biol. 4: 65-76.
Meskin, M.S., Bidlack, W.R., Davies, A.J. & Omaye,
S.T. 2002. Phytochemicals in Nutrition and Health. Boca
Raton: CRC Press. p. 224.
Murthy, K.C., Kim, J., Vikram, A. & Patil, B.S. 2012.
Differential inhibition of human colon cancer cells by structurally
similar flavonoids of citrus. Food Chem. 132: 27-34.
Ngueyem,
T.A., Brusotti, G., Caccialanzaa,
G. & Finzi, P.V. 2009. The genus
Bridelia: A phytochemical and ethnopharmacological
review. J. Ethnopharmacol. 124:
339-349.
Peterson, D.M., Emmons,
C.L. & Hibbs, A.H. 2001. Phenolic antioxidants and antioxidant
activity in pearling fractions of oat groats. J. Cer.
Sci. 33: 97-103.
Priya, V., Jananie, R.K. & Vijayalakshmi,
K. 2011. GC-MS determination of bioactive components of Trigonella
foenum frecum.
J. Chem. Pharm. Res. 3: 35-40.
Rafat, A., Philip, K.
& Muniandy, S. 2010. Antioxidant
potential and phenolic content of ethanolic
extract of selected Malaysian plants. Res. J. Biotechnol.
5: 16-19.
Ravisankar, N., Sivaraj, C., Seeni, S., Joseph,
J. & Raaman, N. 2014. Antioxidant
activity of phytochemical analysis of methanol extract of leaves
of Hypericum hookerianum.
Int. J. Pharm. Pharmaceut. Sci. 6(4): 456-460.
Rashid, M.A., Gustafson,
K.R., Cardellina, J.H. & Boyd,
M.R. 2000. A new podophyllotoxin derivative
from Bridelia ferruginea.
Nat. Prod. Lett. 14: 285-292.
Sachidananda, M.P., Sudeendra, P., Jose, M. & Shrikara,
M.P. 2015. Anticandidal effect of
extract of Bridelia stipularis.
J. Int. Med. Dent. 2: 104-110.
Shanta, M.A., Ahmed, T.,
Uddin, M.N., Majumder, S., Hossain,
M.S. & Rana, M.S. 2013. Phytochemical screening and in
vitro determination of antioxidant potential of methanolic
extract of Streospermum chelonoides.
J. Appl. Pharm. Sci. 3: 117-121.
Sofowora, A. 1993. Medicinal
Plants and Traditional Medicine in Africa. 2nd ed. Ibadan,
Nigeria: Spectrum Books Ltd. p. 289.
Tan, M.C., Tan, C.P.
& Ho, C.W. 2013. Effects of extraction solvent system, time
and temperature and total phenolic content of henna (Lawsonia
inermis) stems. Int. Food Res.
J. 20: 3117-3123.
Togashi, N., Shiraishi, A., Nishizaka, M., Matsuoka,
K., Endo, K., Hamashima, H. &
Inoue, Y. 2007. Antibacterial activity of long-chain fatty alcohol
against Staphylococcus aureus. J. Molecules 12:
139-148.
Nasir, U.S. 2006.
Traditional uses of ethnomedical plants
of the Chittagong Hill tracts. 1st ed. Bangladesh National Herbarium.
pp. 407-408.
Vedavathy, S. 2003. Scope
and importance of traditional medicine. Ind. J. Trad.
Know. 2: 236-239.
Villaño, D., Fernández-Pachón, M.S., Moyá, M.L.,
Troncoso, A.M. & García-Parrilla,
M.C. 2007. Radical scavenging ability of polyphenolic compounds
towards DPPH free radical. Talanta.
71: 230-235.
Wu, X., Beecher,
G.R., Holden, J.M., Haytowitz, D.B.,
Gebhardt, S.E. & Prior, R.L. 2004. Lipophilic and hydrophilic
antioxidant capacities of common foods in the United States.
J. Agric. Food Chem. 52: 4026-4037.
Xu, C., Zhang, Y.,
Cao, L. & Lu, J. 2010. Phenolic compounds and antioxidant
properties of different grape cultivars grown in China. Food
Chem. 119: 1557-1565.
Zlotek, U., Mikulska, S., Nagajek, M. &
Świeca, M. 2016. The effect of different solvents and
number of extraction steps on the polyphenol content and antioxidant
capacity of basil leaves (Ocimum
basilicum L.) extracts. Saudi
J. Biol. Sci. 23: 628-633.
Zuo, Y., Chen, H. &
Deng, Y. 2002. Simultaneous determination of catechins,
caffeine and gallic acids in green,
Oolong, black and pu-erh teas using
HPLC with a photodiode array detector. Talanta
57: 307-316.
*Corresponding author; email: shaheenchem@gmail.com