Phylattrin, a New Cytotoxic Xanthone from Calophyllum soulattri

Our continuing studies on secondary metabolites from the stem bark of Calophyllum soulattri has led to the isolation of another new diprenylated xanthone, phylattrin (1), in addition to five other xanthones and two common sterols. The xanthones are soulattrin (2), caloxanthone C (3), macluraxanthone (4), brasixanthone B (5) and trapezifolixanthone (6) while the sterols are stigmasterol (7) and β-sitosterol (8). The structures of these compounds were determined on the basis of spectroscopic analyses such as 1D and 2D-NMR, HRESIMS, IR and UV. Compounds 1–7 exhibited moderate cytotoxic activities against SNU-1, HeLa, Hep G2, NCI-H23, K562, Raji, LS174T, IMR-32 and SK-MEL-28 cells.

[1]  Y. Taufiq-Yap,et al.  A new furanoxanthone from the stem bark of Calophyllum inophyllum , 2011, Journal of Asian natural products research.

[2]  Y. Taufiq-Yap,et al.  A New Pyranoxanthone from Calophyllum soulattri , 2011, Molecules.

[3]  Y. Taufiq-Yap,et al.  Mucigerin, a new coumarin from Calophyllum mucigerum (Guttiferae) , 2004, Natural product research.

[4]  M. Itoigawa,et al.  Chemical constituents of Calophyllum brasiliensis: structure elucidation of seven new xanthones and their cancer chemopreventive activity. , 2002, Journal of natural products.

[5]  M. Itoigawa,et al.  Cancer chemopreventive agents, 4-phenylcoumarins from Calophyllum inophyllum. , 2001, Cancer letters.

[6]  M. Itoigawa,et al.  A new biflavonoid from Calophyllum panciflorum with antitumor-promoting activity. , 1999, Journal of natural products.

[7]  H. Dharmaratne,et al.  Antimicrobial activity of xanthones from Calophyllum species, against methicillin-resistant Staphylococcus aureus (MRSA). , 1999, Journal of ethnopharmacology.

[8]  Takuya Kumamoto,et al.  An approach to anti-HIV-1 active Calophyllum coumarin synthesis: An enantioselective construction of 2,3-dimethyl-4-chromanone ring by quinine-assisted intramolecular Michael-type addition , 1999 .

[9]  S. Perveen,et al.  Epimers from the leaves of Calophyllum inophyllum , 1999 .

[10]  S. Sotheeswaran,et al.  Anti-HIV coumarins from Calophyllum seed oil. , 1998, Bioorganic & medicinal chemistry letters.

[11]  M. Iinuma,et al.  Two xanthones from root bark of Calophyllum inophyllum , 1995 .

[12]  S. Mohamed,et al.  Hypoglycaemic effect of Parkia speciosa seeds due to the synergistic action of β-sitosterol and stigmasterol , 1994 .

[13]  M. Iinuma,et al.  Two New Xanthones in the Underground Part of Calophyllum inophyllum. , 1994 .

[14]  N. Kunesch,et al.  Neoflavonoids from the stem bark of calophyllum verticillatum , 1987 .

[15]  S. Sotheeswaran,et al.  Triterpenoids and coumarins from the leaves of calophyllum cordato-oblongum , 1985 .

[16]  T. Mosmann.  Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. , 1983, Journal of immunological methods.

[17]  M. Sultanbawa,et al.  Chemical investigation of ceylonese plants. Part VIII. Trapezifolixanthone, a new di-isoprenylated xanthone from the bark of Calophyllum trapezifolium Thw. (Guttiferae) , 1974 .