Cytotoxic xanthone constituents of the stem bark of Garcinia mangostana (mangosteen).

Abstract

Bioassay-guided fractionation of a chloroform-soluble extract of Garcinia mangostana stem bark, using the HT-29 human colon cancer cell line and an enzyme-based ELISA NF-kappaB assay, led to the isolation of a new xanthone, 11-hydroxy-3-O-methyl-1-isomangostin (1). The structure of 1 was elucidated by spectroscopic data analysis. In addition, 10 other known compounds, 11-hydroxy-1-isomangostin (2), 11alpha-mangostanin (3), 3-isomangostin (4), alpha-mangostin (5), beta-mangostin (6), garcinone D (7), 9-hydroxycalabaxanthone (8), 8-deoxygartanin (9), gartanin (10), and cratoxyxanthone (11), were isolated. Compounds 4-8 exhibited cytotoxicity against the HT-29 cell line with ED50 values of 4.9, 1.7, 1.7, 2.3, and 9.1 microM, respectively. In an ELISA NF-kappaB assay, compounds 5-7, 9, and 10 inhibited p65 activation with IC50 values of 15.9, 12.1, 3.2, 11.3, and 19.0 microM, respectively, and 6 showed p50 inhibitory activity with an IC50 value of 7.5 microM. Alpha-mangostin (5) was further tested in an in vivo hollow fiber assay, using HT-29, LNCaP, and MCF-7 cells, but it was found to be inactive at the highest dose tested (20 mg/kg).

• Authors: Ah-Reum Han, Jeong-Ah Kim, Daniel D Lantvit, Leonardus B S Kardono, Soedarsono Riswan, Heebyung Chai, Esperanza J Carcache de Blanco, Norman R Farnsworth, Steven M Swanson, A Douglas Kinghorn
• Journal: Journal of natural products (J Nat Prod) Vol. 72 Issue 11 Pg. 2028-31 (Nov 2009) ISSN: 1520-6025 [Electronic] United States
• PMID: 19839614 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't)

Chemical References

• 11-hydroxy-3-O-methyl-1-isomangostin
• Antineoplastic Agents, Phytogenic
• Xanthones

Topics

• Antineoplastic Agents, Phytogenic (chemistry, isolation & purification, pharmacology)
• Drug Screening Assays, Antitumor
• Garcinia mangostana (chemistry)
• HT29 Cells
• Humans
• Indonesia
• Models, Biological
• Plants, Medicinal (chemistry)
• Xanthones (chemistry, isolation & purification, pharmacology)