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. 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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