Sains Malaysiana 50(9)(2021): 2663-2674

http://doi.org/10.17576/jsm-2021-5009-14

 

Alkaloid Caulerpin and Cytotoxic Activity against NCL-H460 Lung Cancer Cells Isolated along with β-sitosterol from the Halimeda cylindracea Decaisne

(Alkaloid Kaulerpin dan Aktiviti Kesitotoksikannya terhadapSel Barah Paru-Paru NCL-H460

Dipencilkan bersama β-sitosterol daripada Halimeda cylindracea Decaisne)

 

IWAN DINI1, NUNUK HARIANI SOEKAMTO2*, FIRDAUS2, UNANG SUPRATMAN3,4 & JALIFAH LATIP5

 

1Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Negeri Makassar, Makassar, Indonesia

 

2Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Hasanuddin, Makassar, Indonesia

 

3Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jatinangor, Indonesia

 

4Central Laboratory of Universitas Padjadjaran, Jatinangor, Indonesia

 

5School of Chemical Science and Food Technology, Faculty of Science and Tecnology, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor Darul Ehsan, Malaysia

 

Diserahkan: 5 Mei 2020/Diterima: 19 Januari 2021

 

ABSTRACT

Alkaloid caulerpin (1), along with β-sitosterol (2), were isolated from the n-hexane extract of the macroalga Halimeda cylindracea Decaisne. The chemical structure was identified by a spectroscopic method including IR, MS, UV, NMR 1D, NMR 2D, and comparison with data of spectra previously reported. Compounds (1) and (2) were isolated for the first time from this macroalga. Compund (1) were evaluated for their cytotoxicity activity against NCL-H460 lung cancer cells in vitro and showed moderate activity with IC50 value of 20.05 µg/mL.

 

Keywords: β-sitosterol; caulerpin; Halimeda cylindracea; NCL-H460 lung cancer cells

 

ABSTRAK

Alkaloid kaulerpin (1), bersama dengan β-sitosterol (2), diasingkan daripada ekstrak n-heksana daripada makroalga Halimeda cylindracea Decaisne. Struktur kimia dikenal pasti dengan kaedah spektroskopi termasuk IR, MS, UV, NMR 1D, NMR 2D dan perbandingan dengan data spektrum yang dilaporkan sebelumnya. Sebatian (1) dan (2) diasingkan untuk pertama kalinya daripada makroalga ini. Sebatian (1) dinilai untuk aktiviti kesitotoksikannya terhadap sel barah paru-paru NCL-H460 secara in vitro dan menunjukkan aktiviti sederhana dengan nilai IC50 20.05 µg/mL.

 

Kata kunci: β-sitosterol; Halimeda cylindracea; kaulerpin; sel barah paru-paru NCL-H460

 

RUJUKAN

Alarif, W.M., Abou-Elnaga, Z.S., Ayyad, S.E.N. & Al-Lihaibi, S.S. 2010. Insecticidal metabolites from the green alga Caulerpa racemosa. CLEAN - Soil, Air, water 38(5-6): 548-557.

Canche Chay, C.I., Gómez Cansino, R., Espitia Pinzón, C.I., Torres-Ochoa, R.O. & Martínez, R. 2014. Synthesis and anti-tuberculosis activity of the marine natural product caulerpin and its analogues. Mar. Drugs. 12(4): 1757-1772.

Dini, I., Soekamto, N.H., Firdaus & Supratman, U. 2019. Antibacterial and cytotoxic activities assay from the extract of macroalga Halimeda cylindracea from ulf of Boni, Indonesia. Journal of Physics: Conference Series 1341: 032035.

Dzeha, T., Jaspars, M. & Tabudravu, J. 2003. Clionasterol, a triterpenoid from the kenyan marine green macroalga Halimeda macroloba. Western Indian Ocean J. Mar. Sci. 2(2): 157-161.

Esteves, P.O., de Oliveira, M.C., de Souza Barros, C., Cirne-Santos, C.C., Laneuvlille, V.T. & Palmer Paixão, I.C. 2019. Antiviral effect of caulerpin against chikungunya. Natural Product Communications 14(10): 1-6. 

Guiry, M.D. & Guiry, G.M. 2020. AlgaeBase. World-wide electronic publication, National University of Ireland, Galway. http://www.algaebase.org. Accessed on 07 September 2020.

Govindasamy, C.S., Narayani, M., Arulpriya, P., Ruban, K., Anantharaj & Srinivasan, R. 2011. In vitro antimicrobial activities of seaweed extracts against human pathogens. Journal of Pharmacy Research 4(7): 2076-2077.

Güven, K.C., Percot, A. & Sezik, E. 2010. Alkaloids in marine algae. J.  Mar. Drugs 8(2): 269-284. 

Hendri, M., Darmanto, J.S., Prayitno, B., Radjasa, O.K. & Elvita. 2017. The isolation of metabolite compounds from seaweed (Halimeda gracillis) in the waters of Teluk Lampung as a source of antibacterial compounds. International Journal of Marine Science 7(31): 297-307.

Hillis-Colinvaux, L. 1980. Ecology and taxonomy of Halimeda: Primary producer of coral reefs. Advances in Marine Biology 17: 1-327.

Indira, K.S., Balakrishnan, M., Srinivasan, S., Bragadeeswaran & Balasubramanian, T. 2013. Evaluation of in vitro antimicrobial property of seaweed (Halimeda tuna) from Tuticorin coast, Tamil Nadu, Southeast coast of India. African Journal of Biotechnology 12(3): 284-289.

Kadi, A. 1987. Cara mengenal jenis-jenis dari marga Halimeda. Oseana XII(1): 1-12.

Koehn, F.E., Sarath, F., Gunasekera, D., Niel, N. & Cross, S.S. 1991. Halitunal, an unusual diterpene aldehyde from the marine alga Halmeda tuna. Tetrahedron Letters 32(2): 169-172.

Lambert, J.B., Mazzola, E.P. & Ridge, C.D. 2018. Nuclear Magnetic Resonance Spectroscopy: An Introduction to Principles, Applications, and Experimental Methods. 2nd ed. New York: John Wiley & Sons. 

Li, H., Liao, X., Sun, Y., Zhou, R., Long, W., Li, L., Gu, L. & Xu, S. 2018. An economical synthesis of Caulerpin and evaluation of its new anticancer activities. Chemistry Select 3: 12406-12409.

Macedo, N.R.P.V., Ribeiro, M.S., Villaça, R.C., Ferreira, W., Pinto, A.M., Teixeira, V.L., Cirne-Santos, C., Paixao, I.C.N.P. & Giongo, V. 2012. Caulerpin as a potential antiviral drug against herpes simplex virus type 1. Revista Brasileira de Farmacognosia 22: 861-867.

Maiti, B.C. & Thomson, R.H. 1977. Caulerpin. In Marine Natural Products Chemistry, edited by Faulkner, D.J. & Fenical, W.H. Nato Conference Series, Vol. 1. Boston, MA: Springer.

Maiti, B.C., Thomson, R.H. & Mahendran, M. 1978. The structure of Caulerpin, a pigment from Caulerpa algae. J. Chem. Res. Synop. 9: 126-127.

Moo-Puc, R., Robledo, D. & Freile-Pelegrin, Y. 2009. Actividad citotoxica y antiproliferativa in vitro de macroalgas marinas de Yucatan, Mexico. Ciencias Marina 35(4): 345-358.

Natrah, F.M.I., Harah, Z.M., Sidik, B.J., Izzatul, N.M.S. & Syahidah, A. 2015. Antibacterial activities of selected seaweed and seagrass from Port Dickson coastal water against different aquaculture pathogens. Sains Malaysiana 44(9): 1269-1273.

Ovenden, S.P.B., Nielson, J.L., Liptrot, C.H., Willis, R.H., Tapiolas, D.M., Wright, A.D. & Motti, C.S. 2012. Update of spectroscopic data for 4-hydroxydictyolactone and dictyol E isolated from a Halimeda stuposa Dictyota sp. Assemblage. Molecules 17(3): 2929-2938.

Patterson, G.W. 1974. Sterols of some green algae. Comparative Biochemistry and Physiology Part B47(2): 453-457.

Paul, V.J. & Van Alstyne, K.L. 1988. Use of ingested algal diterpenoids by Elysia halimedae Macnae (Opisthobranchia: Ascoglossa) as antipredator defenses. Exp. Mar. Biol. Ecol. 119: 15-29.

Paul, V.J. & Fenical, W. 1984. Novel bioactive diterpenoid metabolites from tropical marine algae of the genera halimeda (Chlorophyta). Tetrahedron 40(16): 3053-3062.

Pinto, A.M.V., Leite, J.P.G., Ferreira, W.J., Cavalcanti, D.N., Villaça, R.C., Giongo, V. & de Palmer Paixão, I.C.N. 2012. Marine natural seaweed products as potential antiviral drugs against Bovine viral diarrhea virus. Revista Brasileira de Farmacognosia22: 813-817.

Selim, S.A. 2012. Antimicrobial, antiplasmid and cytotoxicity potentials of marine algae Halimeda opuntia and Sarconema filiforme collected from Red Sea Coast. World Academy of Science, Engineering and Technology 6(1): 1154-1159S.

Su, J.Y., Xu, X.H., Zeng, L.M., Wang, M.Y., Lu, N., Lu, Y. & Zhang, Q.T. 1998. Sym-triazine derivative from Halimeda xishaensis. Phytochemistry 48(3): 583-584.

Suganya, S., Ishwarya, R., Jayakumar, R., Govindarajan, M., Alharbi, N.S., Kadaikunnan, S., Khaled, J.M., Al-anbr, M.N. & Vaseeharan, B. 2019. New insecticides and antimicrobials derived from Sargassum wightii and Halimeda gracillis seaweeds: Toxicity against mosquito vectors and antibiofilm activity against microbial pathogens. South African Journal of Botany 125: 466-480.

Sun, H.H. & Fenical, W. 1979. Rhipccephalin and rhipocephenal; toxic feeding deterrents from the tropical marine alga rhipccephaius phoenix. Tetrahedron Letters 8: 685-688.

Tillekeratne, L.M.V. & Schmitz. F.J. 1984. 4,9-diaacetoxyyodoteal: A linear diterpene aldehyde from the green alga Halieda opuntia. Phytochemistry 23(6): 1331-1333.

Yang, H., Liu, D.Q., Liang, T.J., Li, J., Liu, A.H., Yang, P. & Wang, B. 2014. Racemosin C, a novel minor bisindole alkaloid with protein tyrosine phosphatase-1B inhibitory activity from the green alga Caulerpa racemosa. Journal of Asian Natural Products Research 16(12): 1158-1165.

Yu, H., Zhang, H., Dong, M., Wu, Z., Shen, Z., Xie, Y., Kong, Z., Dai, X. & Xu, B. 2017. Metabolic reprogramming and AMPKα1 pathway activation by Caulerpin in colorectal cancer cells. Int. J. Oncol. 50(1): 161-172.

 

*Pengarang untuk surat-menyurat; email: nunukhariani@unhas.ac.id

 

     

 

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