Cytotoxic Xanthone Constituents of the Stem Bark of Garcinia mangostana (Mangosteen)

• Published in: Journal of natural products (Washington, D.C.) Vol. 72; no. 11; pp. 2028 - 2031
• Main Authors: Han, Ah-Reum, Kim, Jeong-Ah, Lantvit, Daniel D, Kardono, Leonardus, B. S, Riswan, Soedarsono, Chai, Heebyung, Carcache de Blanco, Esperanza J, Farnsworth, Norman R, Swanson, Steven M, Kinghorn, A. Douglas
• Format: Journal Article
• Language: English
• Published: Northbrook, IL American Chemical Society and American Society of Pharmacognosy 01.11.2009; American Society of Pharmacognosy
• Subjects: anticarcinogenic activity; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Biological and medical sciences; chemical structure; cratoxyxanthone; cytotoxicity; deoxygartanin; Drug Screening Assays, Antitumor; Garcinia mangostana; Garcinia mangostana - chemistry; garcinone; gartanin; General pharmacology; HT29 Cells; human diseases; human health; Humans; hydroxycalabaxanthon; Indonesia; isomangostin; mangostanin; mangostin; Medical sciences; medicinal properties; Models, Biological; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; phytochemicals; Plants, Medicinal - chemistry; secondary metabolites; spectral analysis; stereochemistry; xanthones; Xanthones - chemistry; Xanthones - isolation & purification; Xanthones - pharmacology; Indonesia; Human; Pharmacognosy; Guttiferae; Bark; Cytotoxicity; Isoprenoid; In vitro; Biological activity; Stem; Medicinal plant; Cell line; Fruit crop; Dicotyledones; Angiospermae; Mangosteen; Plant origin; Phenols; Isolation; Spermatophyta; Colon; Transcription factor NFκB; Tumor cell; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np900517h

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-κB 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), 11α-mangostanin (3), 3-isomangostin (4), α-mangostin (5), β-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 μM, respectively. In an ELISA NF-κB 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 μM, respectively, and 6 showed p50 inhibitory activity with an IC50 value of 7.5 μM. α-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).