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

Received: 14 December 2012/Accepted: 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 zeyloxanthanone (2) exhibited strong activity towards five cell lines with IC₅₀ values ranging at 8.00-26.00 μΜ.

Keywords: Calophyllum gracilipes; gracixanthone; 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 trapezifolikanton (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; sterod; trapezifoliksanton; zeyloksantanon

REFERENCES

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 Phytochemistry46: 1423-1429.

Iinuma, M., Tosa, H., Toriyama, N., Tanaka, T., Ito, T. & Chelladurai, V. 1996. Six xanthones from Calophyllum Austroindicum Phytochemistry43: 681-685.

Ishikawa, T. 2000. Anti HIV active Calophyllum coumarins: Distribution, chemistry and activity. Heterocycles 53: 453-474.

Kijjoa, A., Gonzalez, M.J., Pinto, M.M.M., Silva, A.M.S., Anantachoke, C. & Herz, W. 2000. Xanthones from Calophyllum teysmaniivar 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 inophyllumleaf extracts from Fresh Polynesia Islands. Analytica Chimica Acta624: 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 nodosum(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. Phytochemistry52: 669-674.

Whitmore, T.C. 1973. Tree Flora of Malaya: A Manual for Foresters, Vol II. London: Longman. pp. 162-195.

*Corresponding author; email: mawardi@science.upm.edu.my