Sains Malaysiana 51(3)(2022): 873-882

http://doi.org/10.17576/jsm-2022-5103-21

 

Chemical Constituents and Antiproliferative Activity of Eleusine indica (L.) Gaertn.

(Kandungan Kimia dan Aktiviti Antiproliferatif Eleusine indica (L.) Gaertn).

 

SYAHIRAH SUKOR1, ZURIATI ZAHARI1, NORINA RAHIM1, JULIANA YUSOFF2 & FATIMAH SALIM2,3,* 

 

1Faculty of Applied Science, Universiti Teknologi MARA, 40450 Shah Alam, Selangor Darul Ehsan, Malaysia

2Atta-Ur-Rahman Institute for Natural Product and Discovery (AuRins), Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia

  3Centre of Foundation Studies, Universiti Teknologi MARA, Dengkil Campus, 43800 Dengkil, Selangor Darul Ehsan, Malaysia

 

Diserahkan: 1 Januari 2021/Diterima: 12 Ogos 2021

 

Abstract

Eleusine indica, locally known as ‘rumput sambau’ is widely used by traditional practitioners in many parts of the world to treat various ailments including sprained muscle, asthma, black jaundice, stomach pain, diarrhea, convulsions, and those related to infection such as malaria, influenza, dysentery as well as pneumonia. The plant has been reported to possess a wide array of biological activities, which were antioxidant, anti-inflammatory, antimicrobial, antidiabetic, antipyretic, antiplasmodial, antiviral, hepatoprotective, and urolithiasis. Despite all the reported traditional uses and biological activities, not many chemical constituents have been isolated from the plant. In this work, E. indica methanolic and hexane extracts were assessed for their anti-proliferative activities against human liver cancer (HepG2) and African green monkey kidney epithelial normal (Vero) cell lines through 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide  (MTT) assay. Although both extracts were considered to be not active on both cell lines with an IC50 of 91.02 ± 5.74 and 85.30 ± 3.03 µg/mL, and CC50 of >1000 and 639.39 ± 13.97 µg/mL, they were nevertheless more selective towards HepG2 cancer cells compared to the Vero normal cells with selectivity indexes (SI) of 10.99 and 7.50, respectively. Chemical profiling of the extracts on ultra-high performance liquid chromatography (UHPLC) coupled with a diode array detector showed a mixture of different complexity and polarities of compounds. Further isolation and purification on the hexane extract afforded β-sitosterol and stigmasterol, while the methanolic extract yielded loliolide, a benzofuran type of compound. Loliolide has been previously reported to exhibit antitumor activity, which could correlate to the higher antiproliferative selectivity against HepG2 cancer cell line of the methanolic compared to the hexane extracts. This is the first report on the isolation of β-sitosterol, stigmasterol, and loliolide from E. indica.

 

Keywords: Antiproliferative; chemical profile; Eleusine indica; HepG2 cell; loliolide; Vero cell

 

Abstrak

Eleusine indica, atau nama tempatannyarumput sambaudigunakan secara meluas oleh pengamal perubatan tradisi di kebanyakan negara untuk merawat pelbagai jenis penyakit termasuk terseliuh otot, asma, penyakit kuning, sakit perut, cirit-birit, sawan dan yang berkaitan dengan jangkitan seperti malaria, influenza, disentri serta radang paru-paru, termasuklah Malaysia. Dalam kajian ini, ekstrak metanol dan heksana E. indica dinilai untuk aktiviti anti-proliferatifnya terhadap sel tunggal barah hati manusia (HepG2) dan sel tunggal ginjal monyet hijau Afrika (Vero) melalui asai 3-(4,5-dimetiltiazol-2-yl)-2,5-difenil tetrazolium bromide (MTT). Walaupun kedua-dua ekstrak dianggap tidak aktif pada kedua-dua jenis sel tunggal dengan nilai masing-masing IC50 91.02 ± 5.74 dan 85.30 ± 3.03 µg/mL, dan CC50 > 1000 dan 639.39 ± 13.97 µg/mL, namun mereka lebih selektif terhadap sel kanser HepG2 dibandingkan sel normal Vero dengan indeks selektiviti (SI) masing-masing 10.99 dan 7.50. Profil kimia ekstrak pada kromatografi cecair berprestasi tinggi (UHPLC) yang dilengkapi dengan alat pengesan dioda menunjukkan campuran kerumitan dan polariti sebatian yang berbeza. Kerja pengasingan dan pemurnian lebih lanjut pada ekstrak heksana menghasilkan β-sitosterol dan stigmasterol, sementara ekstrak metanol menghasilkan loliolida iaitu sejenis sebatian benzofuran. Loliolida sebelumnya dilaporkan menunjukkan aktiviti antitumor, yang mungkin boleh dikaitkan dengan antiproliferatif selektiviti terhadap sel tunggal barah HepG2 yang lebih tinggi oleh ekstrak metanol dibandingkan dengan ekstrak heksana. Ini adalah laporan pertama mengenai pemencilan β-sitosterol, stigmasterol dan loliolida daripada E. indica.

 

Kata kunci: Antiproliferatif; Eleusine indica; loliolida; profil kimia; sel tunggal HepG2; sel tunggal Vero

 

RUJUKAN

Abdul, G.H., Normah, M.N. & Khatijah, H. 2015. Nature’s Medicine: A Collection of Medicinal Plants from Malaysia’s Rainforest. Kuala Lumpur: Landskap Malaysia.

Azmi,  A., Abdul Rahim, N., Zahari, Z. & Salim, F. 2020. Cytotoxic activity of Erythrina fusca lour. leaf, twig and flower extracts. Malaysian Journal of Analytical Sciences 24(3): 313-319.

Ahmad, R. & Salim, F. 2015. Oxindole alkaloids of Uncaria (Rubiaceae, subfamily Cinchonoideae): A review on its structure, properties, and bioactivities. Vol. 45. Studies in Natural Products Chemistry. Elsevier. pp. 485-525.

Al-Zubairi, A.S., Abdul, A.B., Abdelwahab, S.I., Peng, C.Y., Mohan, S. & Elhassan, M.M. 2011. Eleucine indica possesses antioxidant, antibacterial and cytotoxic properties. Evidence-Based Complementary and Alternative Medicine ECAM 2011: 965370.

Alamgir, K.M., Kawashima, T., Tebayashi, S. & Kim, C.S. 2008. Acylflavonoid C-glycosides from Eleusine coracana. Phytochemistry Letters 1(2): 111-114.

Artun, F.T., Karagoz, A., Ozcan, G., Melikoglu, G., Anil, S., Kultur, S. & Sutlupinar, N. 2016.  In vitro anticancer and cytotoxic activities of some plant extracts on HeLa and Vero cell lines. J. BUON 21(3): 720-725.

Chandrasekara, A. & Shahidi, F. 2015. Determination of antioxidant activity in free and hydrolyzed fractions of millet grains and characterization of their phenolic profiles by HPLC-DAD-ESI-MSn. Journal of Functional Foods 3(3): 144-158.

De Oliveira, P.F., Alves, J.M., Damasceno, J.L., Oliveira, R.A.M., Dias, H.J., Crotti, A.E.M. & Tavares, D.C. 2015. Cytotoxicity screening of essential oils in cancer cell lines. Revista Brasileira de Farmacognosia25(2): 183-188.

Desai, A.V. 2017. Phytochemical investigation of Eleusine indica for in-vivo diuretic and in-vitro anti-urolithiatic activity. World Journal of Pharmaceutical  Research 6(8): 1292-1304.

Goldfarb, R., Saidel, L.J. & Mosovich, E. 1951. The ultraviolet absorption spectra of proteins. Journal of Biological Chemistry 193: 397-404.

Grabarczyk, M., Wińska, K., Mączka, W., Potaniec, B. & Anioł, M. 2015. Loliolide - the most ubiquitous lactone. Folia Biologica et Oecologica 11: 1-8.

Hilu, K.W., Dewet, J.M.J. & Seigler, D. 1987. Flavonoid patterns and systematics in Eleusine. Biochemical Systematics and Ecology 6: 249-251.

Iberahim, R., Yaacob, W.A. & Ibrahim, N. 2015. Phytochemistry, cytotoxicity and antiviral activity of Eleusine indica (sambau). AIP Conference Proceedings 1678(1): 030013.

Iqbal, M. & Gnanaraj, C. 2012. Eleusine indica L. possesses antioxidant activity and precludes carbon tetrachloride (CCl4)-mediated oxidative hepatic damage in rats. Environmental Health and Preventive Medicine - Japan 17(4): 307-315.

Kamal, N., Clements, C., Gray, A.I. & Edrada-Ebel, R.A. 2016. Anti-infective activities of secondary metabolites from Vitex pinnata. Journal of Applied Pharmaceutical Science 6(1): 102-206.

Kulip, J., Unchi, S. & Majawat, G. 2000. Medicinal plants of the Kadazandusun of Kuala Penyu, Sabah, Malaysia. In Proceedings of the 4th Seminar on Tropical Ecosystem Research in Sabah: Research Contributions towards Optimization of Resources in Tropical Ecosystems, edited by Aloysius, D., Goddos, R. & Johniu, F. pp. 179-193.

Lim, T.K. 2016. Edible medicinal and non-medicinal plants. Vol 12 Modified Stems, Roots, Bulb. Springer Science Business Media 11: 1-690.

Morah, F.N.I. & Otuk, M. 2015. Antimicrobial and anthelmintic activity of Eleusine indica. Acta Scientiae et Intellecuts 1(4): 28-32.

Murata, M., Nakai, Y., Kawazu, K., Ishizaka, M., Kajiwara, H., Abe, H., Takeuchi, K., Ichinose, Y., Mitsuhara, I., Mochizuki, A. & Seo, S. 2019. Loliolide, a carotenoid metabolite, is a potential endogenous inducer of herbivore resistance. Plant Physiology 179(4): 1822-1833.

Peñaloza, E.M.C., Casanova, L.M., Leal, I.C.R., De Aguiarc, P.F. & Costa, S.S. 2018. Metabolite fingerprinting and profiling of the medicinal grass Eleusine indica based on HPLC-DAD, UPLC-DAD-MS/MS and NMR analyses. Journal of the Brazilian Chemical Society 29(12): 2522-2534.

Phuong, N.M., Sung, T.V., Ripperger, H. & Adam, G. 1994. Sterol glucosides from Eleucine indica. Planta Med. 60(5): 498.

Piah, D. 2020. Direct communication with Nenek Piah, a traditional practitioner from ethnic Kadasan/Dusun at Keningau, Sabah (Pers. Comm.).

Salim, F. 2013. Phytochemicals from Malaysian Uncaria longifloravar. pteropoda (Miq) Ridsd. and their activities against the human neuroblastoma SH-SY5Y cell line. Ph.D. Thesis, Universiti Teknologi MARA, Shah Alam, Selangor, Malaysia (Unpublished).

Salim, F., Zain, M.M., Ridzuan, M.S.M., Langat, M.K., Mulholland, D.A. & Ahmad, R. 2013. Flavan-3-ols from the leaves of Malaysian Uncaria longiflora var. pteropoda (Miq.) Ridsd. Phytochemistry Letters 6: 236-240.

Suffness, M. & Pezzuto, J.M. 1990. Assays related to cancer drug discovery. In Methods in Plant Biochemistry: Assays for Bioactivity, edited by Hostettmann, K. London:  Academic Press. pp. 71-133.

Yang, X., Kang, M.C., Lee, K.W., Kang, S.M., Lee, W.W. & Jeon, Y.J. 2011. Antioxidant activity and cell protective effect of loliolide isolated from Sargassum ringgoldianum subsp. coreanum. Algae 26(2): 201-208.

Yuan, Z., Zheng, X., Zhao, Y., Liu, Y., Zhou, S., Wei, C., Hu, Y. & Shao, H. 2018. Phytotoxic compounds isolated from leaves of the invasive weed Xanthium spinosum. Molecules 23(11): 2840.

Zhang, C., Zhou, J., Yang, J., Li, C., Ma, J., Zhang, D. & Zhang, D. 2016. Two new phenylpropanoid glycosides from the aerial parts of Lespedeza cuneata. Acta Pharmaceutica Sinica B 6(6): 564-567.

 

*Pengarang untuk surat-menyurat; email: fatimah2940@uitm.edu.my

 

 

   

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