Sains Malaysiana 47(8)(2018): 1749–1756

http://dx.doi.org/10.17576/jsm-2018-4708-14

Isolation of Carbazole Alkaloids and Coumarins from Aegle marmelos and Murraya koenigii and Their Antioxidant Properties

(Pengasingan Alkaloid dan Koumarin daripada Karbazol Aegle marmelos dan Murraya koenigii serta Sifat Antioksidannya)

ROU CHIAN NG¹, NUR KARTINEE KASSIM^1*, YUNIE SOON YU YEAP¹, GWENDOLINE CHENG LIAN EE¹, SAIFUL LATIFAH YAZAN² & KHALID HAMID MUSA³

¹Department of Chemistry, Faculty of Science, 43300 UPM Serdang, Selangor Darul Ehsan, Malaysia

²Department of Biomedical Sciences, Faculty of Medicine and Health Sciences, 43300 UPM Serdang, Selangor Darul Ehsan, Malaysia

³School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor Darul Ehsan, Malaysia

Received: 29 August 2017/Accepted: 21 March 2018

ABSTRACT

In this paper, antioxidant properties of Aegle marmelos (stem bark, leaves) and Murraya koenigii (stem bark, root) were evaluated by 2,2-diphenyl-1-picrylhydrazy (DPPH) free radical scavenging, 2,2’-Azino-bis(3-ethylbenzthiozoline-6-sulfonic acid) (ABTS) decolourisation, cupric reducing antioxidant capacity (CUPRAC), ferric reducing antioxidant power (FRAP) and linoleic acid/β-carotene assays. The chloroform extract of Murraya koenigii stem bark was found to possess the highest antioxidant activity in CUPRAC (1490.89 mgTE/g extract). In contrary, the hexane extract from Aegle marmelos leaves exhibited the weakest antioxidant activity in the DPPH assay (81.06 mgTE/g extract). The bioactive compound mahanimbine (7) isolated from the stem bark of Murraya koenigii was found to be the most active antioxidant agent with TEAC of 927.73 and 1649.31 mgTE/g corresponding to the ABTS and CUPRAC assays, respectively, as well as a good lipid peroxidation inhibitor with an inhibitory percentage of 70.95%. These CUPRAC and ABTS assays are the first report for Malaysian Murraya koenigii species.

Keywords: Aegle marmelos; antioxidant; CUPRAC; mahanimbine; Murraya koenigii

ABSTRAK

Dalam kertas ini, sifat antipengoksida Aegle marmelos (kulit batang, daun) dan Murraya koenigii (kulit batang, akar) dinilai oleh perencatan radikal bebas 2,2-difenil-1-pikrilhidrazil (DPPH), Asid-2,2’-azino-bis(3-etilbenztiozolin-6-sulfonik) (ABTS), kapasiti antipengoksida penurunan ion kuprik (CUPRAC), kuasa antioksidan penurunan ion ferik (FRAP) dan asid linoleat/β-karotena. Ekstrak kloroform kulit batang Murraya koenigii didapati memiliki aktiviti antioksidan tertinggi dalam CUPRAC (1490.89 mgTE/g ekstrak). Sebaliknya, ekstrak heksana daripada daun Aegle marmelos memperlihatkan aktiviti antioksidan paling lemah dalam penilaian DPPH (81.06 mgTE/g ekstrak). Mahanimbine (7) merupakan sebatian yang diasingkan daripada kulit batang Murraya koenigii didapati sebagai agen antioksidan paling aktif dengan TEAC daripada 927.73 mgTE/g sampel dan 1649.31 mgTE/g sampel sepadan dengan ujian ABTS dan CUPRAC serta perencat lipid yang baik dengan peratusan perencatan 70.95%. Ujian CUPRAC dan ABTS ini merupakan laporan pertama untuk spesies Malaysia Murraya koenigii.

Kata kunci: Aegle marmelos; antioksidan; CUPRAC; mahanimbin; Murraya koenigii

REFERENCES

Almeida, M.M.B., Paulo, H.M., Ângela, M.C.A., Giovana, M., Carlos, E.M., Geraldo, A.M. & Telma, L.G. 2011. Bioactive compounds and antioxidant activity of fresh exotic fruits from northeastern Brazil. Food Research International 44(7): 2155-2159.

Ariharan, V.N., Kalirajan, K. & Prasad, P.K. 2014. Antioxidant property of different phenotypic traits of Aegle marmelos (l.) Corr.–vilvam. International Journal of Pharma and Bio Sciences 5(4): 692-697.

Bendary, E., Francis, R.R., Ali, H.M.G., Sarwat, M.I. & Hady, S.E. 2013. Antioxidant and structure-activity relationships (SARs) of some phenolic and anilines compounds. Annals of Agricultural Sciences 58(2): 173-181.

Bernhoft, A. 2010. A brief review on bioactive compounds in plants. Bioactive compounds in plants-benefits and risks for man and animals. Proceedings from a Symposium, the Norwegian Academy of Science and Letters, Oslo, Norway.

Gil-González, J.H., Diego, L.D., Benjamín, A.R. & Juan, C.M. 2013. Antioxidant activity and chemical composition of Biocides from Wild Medicinal Plants, edited by Cespedes, C., Sampietro, D., Rai, M. & Seigler, D. Oxfordshire: CABI. p. 92.

Guaadaoui, A., Soumaya, B., Naima, E., Mohammed, B. & Abdellah, H. 2014. What is a bioactive compound? A combined definition for a preliminary consensus. International Journal of Nutrition and Food Sciences 3(3): 174-179.

Jagan Mohan Rao, L., Ramalakshmi, K., Borse, B.B. & Raghavan, B. 2007. Antioxidant and radical-scavenging carbazole alkaloids from the oleoresin of curry leaf (Murraya koenigii Spreng.). Food Chemistry 100(2): 742-747.

Jayaprakasha, G.K., Singh, R.P. & Sakariah, K.K. 2001. Antioxidant activity of grape seed (Vitis vinifera) extracts on peroxidation models in vitro. Food Chemistry 73(3): 285-290.

Kassim, N.K., Rahmani, M., Ismail, A., Sukari, M.A., Gwendoline, C.L.E., Nadiah, M.N. & Khalijah, A. 2013. Antioxidant activity-guided separation of coumarins and lignan from Melicope glabra (Rutaceae). Food Chemistry 139(1): 87-92.

León-González, A.J., Cyril, A. & Valérie, B.S. 2015. Pro-oxidant activity of polyphenols and its implication on cancer chemoprevention and chemotherapy. Biochemical Pharmacology 98(3): 371-380.

Lopez, M., Mart?nez, F., Del Valle, C., Ferrit, M. & Luque, R. 2003. Study of phenolic compounds as natural antioxidants by a fluorescence method. Talanta 60(2-3): 609-616.

Moon, J.K. & Takayuki, S. 2009. Antioxidant assays for plant and food components. Journal of Agricultural and Food Chemistry 57(5): 1655-1666.

Moure, A., Jose, M.C., Daniel, F., Manuel, D.J., Jorge, S., Herminia, D., Mar?́a, J.N. & Carlos, P.J. 2001. Natural antioxidants from residual sources. Food Chemistry 72(2): 145-171.

Ningappa, M.B., Ramadas, D. & Leela, S. 2008. Antioxidant and free radical scavenging activities of polyphenol-enriched curry leaf (Murraya koenigii L.) extracts. Food Chemistry 106(2): 720-728.

Özkan, M., Patrick, B.C., Mutiso, L.N., Peng, L., Sarah, B., Wang, W. & Sarker, S.D. 2013. Zanthoxylum usambarense (Engl.) Kokwaro (Rutaceae) extracts inhibit the growth of the breast cancer cell lines MDA-MB-231 and MCF-7, but not the brain tumour cell line U251 in vitro. Phytotherapy Research 27(5): 787-790.

Pereira, A.S., Seixas, F.R. & Aquino Neto, F.R. 2002. Própolis: 100 anos de pesquisa e suas perspectivas futuras. Química Nova 25: 321-326.

Reihani, S.F.S. & Azhar, M.E. 2012. Antioxidant activity and total phenolic content in aqueous extracts of selected traditional Malay salads (Ulam). International Food Research Journal 19(4): 1439-1444.

Sasidharan, I. & Nirmala, M.A. 2011. Effects of temperature and solvent on antioxidant properties of curry leaf (Murraya koenigii L.). Journal of Food Science and Technology 48(3): 366-370.

Satyal, P., Katherine, E.W., Noura, S.D., Sanjaya, N. & William, N.S. 2012. Biological activities and volatile constituents of Aegle marmelos (L.) Corrêa from Nepal. Journal of Medicinally Active Plants 1(3): 114-122.

Shimada, K., Fujikawa, K., Yahara, K. & Nakamura, T. 1992. Antioxidative properties of xanthan on the autoxidation of soybean oil in cyclodextrin emulsion. Journal of Agricultural and Food Chemistry 40(6): 945-948.

Singh, A.P., Wilson, T., Luthria, D., Freeman, M.R., Scott, R.M., Bilenker, D., Shah, S., Somasundaram, S. & Vorsa, N. 2011. LC-MS-MS characterisation of curry leaf flavonols and antioxidant activity. Food Chemistry 127(1): 80-85.

Tachakittirungrod, S., Siriporn, O. & Sombat, C. 2007. Study on antioxidant activity of certain plants in Thailand: Mechanism of antioxidant action of guava leaf extract. Food Chemistry 103(2): 381-388.

Weaver, C.M. 2014. Bioactive foods and ingredients for health. Advances in Nutrition: An International Review Journal 5(3): 306S-311S.

Yeap, Y.S.Y., Nur, K.K., Rou, C.N., Gwendoline, C.L.E., Latifah, S.Y. & Khalid, H.M. 2017. Antioxidant properties of ginger (Kaempferia angustifolia Rosc.) and its chemical markers. International Journal of Food Properties 20(Issue sup 1): S1158-S1172.

Zhang, P. & Omaye, S.T. 2001. Antioxidant and prooxidant roles for β-carotene, α-tocopherol and ascorbic acid in human lung cells. Toxicology In Vitro 15(1): 13-24.

Zhang, D., Thomas, G.H. & Mabberley, D.J. 2008. Rutaceae. Flora of China 11: 51. http://flora.huh.harvard.edu/china/ mss/volume11/Rutaceae.pdf - unknown status. Accessed on May 10, 2013.

*Corresponding author; email: kartinee@upm.edu.my