Sains
Malaysiana 42(9)(2013): 1261–1266
Xanthones from Calophyllum
gracilipes and Their Cytotoxic Activity
(Zanton daripada Calofilum grasilipes dan
Aktiviti Ketoksikannya)
Nadiah Mad Nasir1, Mawardi
Rahmani1*, Khozirah
Shaari1,
Nur Kartinee Kassim1,
Rusea Go2, Johnson Stanslas3
& Ethel Jeyaseela Jeyaraj3
1Department
of Chemistry, Universiti Putra Malaysia,
43400 UPM,
Serdang, Malaysia
2Department of Biology, Universiti Putra Malaysia, 43400 UPM, Serdang,
Malaysia
3Departments of Medicine, Universiti Putra Malaysia, 43400 UPM, Serdang,
Selangor
Diserahkan: 14 Disember 2012/Diterima:
11 April 2013
ABSTRACT
Extraction and chromatographic isolation of the
hexane, chloroform and methanol extracts of stem bark of Calophyllum gracilipes has led to the isolation
of a new xanthone, gracixanthone (1) and the known zeyloxanthanone
(2) and trapezifolixanthone (3) together with three common sterols,
namely stigmasterol, friedelin and lupeol. The structures of the
compounds were elucidated and established by spectroscopic analysis
and compared with the spectral data from literature. The cytotoxicity
of the compounds was evaluated and zeyloksanthanone (2) exhibited
strong activity towards five cell lines with IC50 values
ranging at 8.00-26.00 μΜ.
Keywords: Calophyllum gracilipes; gracixanton; sterols; trapezifolixanthone;
zeyloxanthanone
ABSTRAK
Pengekstrakan dan pemisahan kromatografi terhadap
ekstrak heksana, klorofom dan metanol kulit batang Calofilum grasilipes telah berjaya memisahkan
satu zanton baru, graciksanton (1) dan dua zanton kenali, zeyloksantanon
(2) dan trapezifoliksanton (3) bersama dengan tiga sterol biasa,
stigmasterol, friedelin dan lupeol. Struktur
sebatian ini telah dikenal pasti dengan kaedah analisis spektroskopi
dan dibandingkan dengan data spektrum yang terdapat dalam rujukan.
Ujian ketoksikan sebatian ini telah ditentukan dan zeyloksantanon
(2) menunjukkan aktiviti yang kuat terhadap lima sel dengan nilai IC50 dalam julat 8.00-26.00
μΜ.
Kata kunci: Calofilum
grasilipes; graciksanton; steros; trapezifoliksanton;
zeyloksantanon
RUJUKAN
Ali,
M.S., Mahmud, S., Perveen, S., Ahmad, V.U. & Rizwani, G.H. 1999. Epimers from the leaves of Calophyllum
inophyllum. Phytochemistry 50: 1385-1389.
Corner,
E.J.H. 1988. Wayside
Trees of Malaya. Kuala Lumpur: The Malayan Nature Society, Malaysia.
Ee,
G.C.L., Mah, S.H., Rahmani, M., Taufiq-Yap, Y.H., Teh, S.S. & Lim, Y.M.
2011. A new furanoxanthone from
stem bark of Calophyllum inophyllum. Journal of Asian Natural
Products Research 13: 956-960.
Hay, A-E., Helesbeux, J-J.,
Duval, O., Labaied, M., Grellier, P. & Richomme, P. 2004. Antimalarial xanthones from Calophyllum caledonicum and Garcinia
vieillardii. Life Sciences 75: 3077-3085.
Iinuma,
M., Ito, T., Tosa, H., Tanaka, T., Miyake, R. & Chelladurai, V. 1997. Prenylated xanthonoids from Calophyllum
apetalum Phytochemistry 46: 1423-1429.
Iinuma,
M., Tosa, H., Toriyama, N., Tanaka, T., Ito, T. & Chelladurai, V. 1996. Six xanthones from Calophyllum austroindicum
Phytochemistry 43: 681-685.
Ishikawa, T. 2000. Anti HIV
active Calophyllum coumarins: Distribution, chemistry and activity. Heterocycles 53: 453.
Kijjoa,
A., Gonzalez, M.J., Pinto, M.M.M., Silva, A.M.S., Anantachoke, C. & Herz,
W. 2000. Xanthones
from Calophyllum teysmanii var inophylloide. Phytochemistry 55: 833-836.
Kostova, I. 2006, Coumarins
as inhibitors of HIV reverse transcriptase. Current HIV Research 4:
347-363.
Laure, F.,
Raharivelomanana, P., Butaud, J-F., Bianchini, J-P.
& Gaydou, E.M. 2008. Screening of anti-HIV-1 inophyllums by HPLC-DAD of Calophyllum
inophyllum leaf extracts from Fresh Polynesia Islands. Analytica Chimica
Acta 624: 147-153.
Nasir, N.M., Rahmani, M., Shaari, K., Ee,
G.C.L., Go, R., Kassim, N.K., Muhamad, S.N.K. & Iskandar, M.J. 2011.
Two new xanthones from Calophyllum nodusum (Guttiferae). Molecules 16: 8973-8980.
Seo, E.K., Wall, M.E., Wani, M.C.,
Navarro, H., Mukherjee, R., Farnsworth, N.R. & Kinghorn, A.D. 1999. Cytotoxic constituents from the roots of Tovomita brevistaminea. Phytochemistry 52: 669-674.
Whitmore, T.C. 1973. Tree Flora of
Malaya: A Manual for Foresters, Vol II. London: Longman.
Pp. 162-195.
*Pengarang untuk surat-menyurat; email: mawardi@science.upm.edu.my
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