Planta Med 2013; 79 - OP6
DOI: 10.1055/s-0033-1336420

Caged Polyprenylated Xanthones from Medicinal Plants of the Genus Garcinia

HM Hua 1, 2, ZL Li 1, 2, SL Niu 1, 2, LL Wang 1, 2, YK Jing 3
  • 1Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, P. R. China
  • 2School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, P. R. China
  • 3Department of Medicine, Mount Sinai School of Medicine, New York, NY 10029, USA

The medicinal plants of the genus Garcinia, which belongs to the family of Guttiferae (Clusiaceae), are well-known as rich sources of xanthones, biflavones, and benzophenones. Caged Garcinia xanthones, represented by gambogic acid, are a family of structurally diversified compounds possessing an unusual 4-oxatricyclo[4.3.1.03,7]dec-8-en-2-one (caged) scaffold, which have attracted great interest as challenging projects for total synthesis and biosynthetic research [1]. Gambogic acid is the main active compound of gamboge used as detoxificating, homeostasis-maintaining, anti-inflammatory, and parasiticidal medicines for thousands of years [2]. The chemical constituents in the resin of G. hanburyi and the leaves and stem barks of G. bracteata were investigated. Seventeen compounds were isolated from resin of G. hanburyi and 75 compounds from the leaves and stem barks of G. bracteata, of which totally 29 caged Garcinia xanthones including 13 new ones were obtained [3,4,5]. Twelve caged polyprenylated xanthones from resin of G. hanburyi inhibited cell growth with different activities against P388 and P388/ADR cells, in which gambogellic acid (1) and gambogic acid (2) were the most potent. Fourteen caged xanthones isolated from the leaves of G. bracteata showed potent cell growth inhibitory activities against HL-60 and K562 cells. 3-O-Methylbractatin (3) showed the most potent inhibitory activity against HL-60 with a GI50 value of 0.16 µM.

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Acknowledgements: Thanks go to Mr. Jingyun Cui for the collection of plant materials. This work was supported by National Natural Science Foundation (No. 81172958) of PRC. References: [1] Chantarasriwong O, Theodorakis EA, et al. (2010) Chem Eur J, 16: 9944 – 9962. [2] Yi TF, Liu MY, et al. (2008) Cancer Res, 68: 1843 – 1850. [3] Wang LL, Hua HM, et al. (2008) Chinese Chem Lett, 19: 1221 – 1223. [4] Wang LL, Hua HM, et al. (2008) Planta Med, 74: 1735 – 1740. [5] Niu SL, Hua HM, et al. (2012) Phytochemistry, 77: 280 – 286.