Three New Xanthones from the Resin of Garcinia hanburyi

Abstract

Three new xanthones, 22,23-dihydroxydihydrogambogenic acid (1), 12-hydroxygambogefic acid A (2), and hanburixanthone (3), along with thirteen known compounds were isolated from the resin of Garcinia hanburyi. The structures of the new compounds were determined by detailed analysis of 1D and 2D NMR spectra and by comparison with related model compounds. All compounds were tested for their cytotoxicities against A549, HCT116, and MDA-MB-231, and most of them showed significant effects on the cell lines.

Key words

Garcinia hanburyi - Clusiaceae - xanthones - cytotoxicity

• References

• 1 Han QB, Wang YL, Yang L, Tso TF, Qiao CF, Song JZ, Xu LJ, Chen SL, Yang DJ, Xu HX. Cytotoxic polyprenylated xanthones from the resin of Garcinia hanburyi . Chem Pharm Bull 2006; 54: 265-267
• 2 Lin LJ, Lin LZ, Pezzuto JM, Cordell GA. Isogambogic acid and isomorellinol from Garcinia hanburyi . Magn Reson Chem 1993; 31: 340-347
• 3 Asano J, Chiba K, Tada M, Yoshii T. Cytotoxic xanthones from Garcinia hanburyi . Phytochemistry 1996; 41: 815-820
• 4 Feng F, Liu WY, Chen YS, Guo QL, You QD. Five novel prenylated xanthones from Resina Garciniae. J Asian Nat Prod Res 2007; 9: 735-741
• 5 Han QB, Yang L, Wang YL, Qiao CF, Song JZ, Sun HD, Xu HX. A pair of novel cytotoxic polyprenylated xanthone epimers from gamboges. Chem Biodivers 2006; 3: 101-105
• 6 Jia MM, Shou QY, Tan Q, Shen ZW. Chemical Constitutes of Garcinia hanburyi . Acta Chim Sin 2008; 66: 2513-2517
• 7 Sukpondma Y, Rukachaisirikul V, Phongpaichit S. Antibacterial caged-tetraprenylated xanthones from the fruits of Garcinia hanburyi . Chem Pharm Bull 2005; 53: 850-852
• 8 Tao SJ, Guan SH, Li XN, Guo DA. A Highly Rearranged Pentaprenylxanthonoid from the Resin of Garcinia hanburyi . Helv Chim Acta 2010; 93: 1395-1400
• 9 Tao SJ, Guan SH, Wang W, Lu ZQ, Chen GT, Sha N, Yue QX, Liu X, Guo DA. Cytotoxic polyprenylated xanthones from the resin of Garcinia hanburyi . J Nat Prod 2009; 72: 117-124
• 10 Wang LL, Li ZL, Song DD, Sun L, Pei YH, Jing YK, Hua HM. Two novel triterpenoids with antiproliferative and apoptotic activities in human leukemia cells isolated from the resin of Garcinia hanburyi . Planta Med 2008; 74: 1735-1740
• 11 Wang LL, Li ZL, Xu YP, Liu XQ, Pei YH, Jing JK, Hua HM. A new cytotoxic caged polyprenylated xanthone from the resin of Garcinia hanburyi . Chin Chem Lett 2008; 19: 1221-1223
• 12 Deng YX, Pan SL, Zhao SY, Wu MQ, Sun ZQ, Chen XH, Shao ZY. Cytotoxic alkoxylated xanthones from the resin of Garcinia hanburyi . Fitoterapia 2012; 83: 1548-1552
• 13 Elfita E, Muharni M, Latief M, Darwati D, Widiyantoro A, Supriyatna S, Bahti HH, Dachriyanus D, Cos P, Maes L, Foubert K, Apers S, Pieters L. Antiplasmodial and other constituents from four Indonesian Garcinia spp . Phytochemistry 2009; 70: 907-912
• 14 Lee S. Fractionated product of gamboge resin useful for treating cancer, is obtained by fractionating acetone-extracted product from resin powder by chromatography to provide five eluates; and separately concentrating, partitioning and refining. EP Patent 2395007-A1; 2011.
• 15 Bhat HB, Nair PM, Venkataraman K. The colouring matters of Garcinia morella: Part V – Isolation of desoxymorellin & dihydroisomorellin. Indian J Chem 1964; 2: 405-410
• 16 Tao SJ, Wang Y, Zhang X, Guan SH, Guo DA. Biotransformation of gambogenic acid by Chaetomium globosum CICC 2445. Nat Prod Commun 2012; 7: 197-198
• 17 Li NG, You QD, Huang XF, Wang JX, Guo QL, Chen XG, Li Y, Li HY. Structure-activity relationship of gambogic acid. Chin J Nat Med 2008; 6: 37-42