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

被引:86
作者
Han, Ah-Reum [1 ]
Kim, Jeong-Ah [1 ]
Lantvit, Daniel D. [2 ]
Leonardus, B. S. Kardono [3 ]
Riswan, Soedarsono [4 ]
Chai, Heebyung [1 ]
de Blanco, Esperanza J. Carcache [1 ]
Farnsworth, Norman R. [2 ]
Swanson, Steven M. [2 ]
Kinghorn, A. Douglas [1 ]
机构
[1] Ohio State Univ, Coll Pharm, Columbus, OH 43210 USA
[2] Univ Illinois, Coll Pharm, Chicago, IL 60612 USA
[3] Indonesian Inst Sci, Res Ctr Chem, Tangerang 15310, Indonesia
[4] Indonesian Inst Sci, Biol Res Ctr, Herbarium Bogoriense, Bogor 16122, Indonesia
来源
JOURNAL OF NATURAL PRODUCTS | 2009年 / 72卷 / 11期
关键词
PRENYLATED XANTHONES;
D O I
10.1021/np900517h
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
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-kappa B 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), 11 alpha-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 mu M, respectively. In an ELISA NF-kappa B 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 mu M, respectively, and 6 showed p50 inhibitory activity with an IC50 value of 7.5 mu M. 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).
引用
收藏
页码:2028 / 2031
页数:4
相关论文
共 31 条
[1]   Anti-cancer effects of xanthones from pericarps of mangosteen [J].
Akao, Yukihiro ;
Nakagawa, Yoshihito ;
Iinuma, Munekazu ;
Nozawa, Yoshinori .
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2008, 9 (03) :355-370
[2]   Xanthones from the botanical dietary supplement mangosteen (Garcinia mangostana) with aromatase inhibitory activity [J].
Balunas, Marcy J. ;
Su, Bin ;
Brueggemeier, Robert W. ;
Kinghorn, A. Douglas .
JOURNAL OF NATURAL PRODUCTS, 2008, 71 (07) :1161-1166
[3]   TRITERPENOIDS, TOCOTRIENOLS AND XANTHONES FROM THE BARK OF CRATOXYLUM-COCHINCHINENSE [J].
BENNETT, GJ ;
HARRISON, LJ ;
SIA, GL ;
SIM, KY .
PHYTOCHEMISTRY, 1993, 32 (05) :1245-1251
[4]   Mangostanol, a prenyl xanthone from Garcinia mangostana [J].
Chairungsrilerd, N ;
Takeuchi, K ;
Ohizumi, Y ;
Nozoe, S ;
Ohta, T .
PHYTOCHEMISTRY, 1996, 43 (05) :1099-1102
[5]   Xanthones with quinone reductase-inducing activity from the fruits of Garcinia mangostana (Mangosteen) [J].
Chin, Young-Won ;
Jung, Hyun-Ah ;
Chai, Heebyung ;
Keller, William J. ;
Kinghorn, A. Douglas .
PHYTOCHEMISTRY, 2008, 69 (03) :754-758
[6]   Structural Characterization, Biological Effects, and Synthetic Studies on Xanthones from Mangosteen (Garcinia mangostana), a Popular Botanical Dietary Supplement [J].
Chin, Young-Won ;
Kinghorn, A. Douglas .
MINI-REVIEWS IN ORGANIC CHEMISTRY, 2008, 5 (04) :355-364
[7]  
Crews P., 1998, Organic Structure Analysis
[8]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[9]   Garcinia mangostana:: a source of potential anti-cancer lead compounds against CEM-SS cell line [J].
Ee, Gwendoline Cheng Lian ;
Daud, Shaari ;
Izzaddin, Sheikh Ahmad ;
Rahmani, Mawardi .
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2008, 10 (05) :481-485
[10]   XANTHONES OF GARCINIA-MANGOSTANA LINN [J].
GOVINDACHARI, TR ;
KALYANARAMAN, PS ;
MUTHUKUMARASWAMY, N ;
PAI, BR .
TETRAHEDRON, 1971, 27 (16) :3919-+