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 KHAN^2*, 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

 

Diserahkan: 29 Ogos 2018/Diterima: 27 Februari 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

RUJUKAN

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.

 

*Pengarang untuk surat-menyurat; email: shaheenchem@gmail.com