Antioxidant Xanthones from the Pericarp of Garcinia mangostana (Mangosteen)

As part of ongoing research on cancer chemopreventive agents from botanical dietary supplements, Garcinia mangostana L. (commonly known as mangosteen) was selected for detailed study. Repeated chromatography of a CH2Cl2-soluble extract of the pericarp led to the isolation of two new highly oxygenate...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2006-03, Vol.54 (6), p.2077-2082
Main Authors: Jung, Hyun-Ah, Su, Bao-Ning, Keller, William J, Mehta, Rajendra G, Kinghorn, A. Douglas
Format: Article
Language:English
Subjects:
Animal productions
Antioxidants - isolation & purification
Biological and medical sciences
Fruit - chemistry
Fundamental and applied biological sciences. Psychology
Garcinia mangostana - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Terrestrial animal productions
Vertebrates
Xanthones - chemistry
Xanthones - isolation & purification
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Summary:As part of ongoing research on cancer chemopreventive agents from botanical dietary supplements, Garcinia mangostana L. (commonly known as mangosteen) was selected for detailed study. Repeated chromatography of a CH2Cl2-soluble extract of the pericarp led to the isolation of two new highly oxygenated prenylated xanthones, 8-hydroxycudraxanthone G (1) and mangostingone [7-methoxy-2-(3-methyl-2-butenyl)-8-(3-methyl-2-oxo-3-butenyl)-1,3,6-trihydroxyxanthone, 2], together with 12 known xanthones, cudraxanthone G (3), 8-deoxygartanin (4), garcimangosone B (5), garcinone D (6), garcinone E (7), gartanin (8), 1-isomangostin (9), α-mangostin (10), γ-mangostin (11), mangostinone (12), smeathxanthone A (13), and tovophyllin A (14). The structures of compounds 1 and 2 were elucidated by spectroscopic data analysis. Except for compound 2, which was isolated as a minor component, the antioxidant activities of all isolates were determined using authentic and morpholinosydnonimine-derived peroxynitrite methods, and compounds 1, 8, 10, 11, and 13 were the most active. α-Mangostin (10) inhibited 7,12-dimethylbenz[α]anthracene-induced preneoplastic lesions in a mouse mammary organ culture assay with an IC50 of 1.0 μg/mL (2.44 μM). Keywords: Garcinia mangostana; mangosteen; Clusiaceae; prenylated xanthones; antioxidant activity; mouse mammary organ culture assay
ISSN:0021-8561
1520-5118
DOI:10.1021/jf052649z