Xanthones with quinone reductase-inducing activity from the fruits of Garcinia mangostana (Mangosteen).
Bioactivity-guided fractionation of a dichloromethane-soluble extract of Garcinia mangostana fruits has led to the isolation and identification of five compounds, including two xanthones, 1,2-dihydro-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-enyl)furo[3,2-a]xanthen-11-one (1) and 6-deoxy-7-demethylmangostanin (2), along with three known compounds, 1,3,7-trihydroxy-2,8-di-(3-methylbut-2-enyl)xanthone (3), mangostanin (4), and alpha-mangostin (5). The structures of compounds 1 and 2 were determined from analysis of their spectroscopic data. All isolated compounds in the present study together with eleven other compounds previously isolated from the pericarp of mangosteen, were tested in an in vitro quinone reductase-induction assay using murine hepatoma cells (Hepa 1c1c7) and an in vitro hydroxyl radical antioxidant assay. Of these, compounds 1-4 induced quinone reductase (concentration to double enzyme induction, 0.68-2.2microg/mL) in Hepa 1c1c7 cells and gamma-mangostin (6) exhibited hydroxyl radical-scavenging activity (IC50, 0.20microg/mL).
Chin
Young-Won
YW
Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA.
Jung
Hyun-Ah
HA
Chai
Heebyung
H
Keller
William J
WJ
Kinghorn
A Douglas
AD
D000818:Animals; D016588:Anticarcinogenic Agents / Q000737:chemistry / Q000302:isolation & purification; D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004789:Enzyme Activation / Q000187:drug effects; D005638:Fruit / Q000737:chemistry*; D029762:Garcinia mangostana / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D017665:Hydroxyl Radical / Q000737:chemistry; D008752:Methylene Chloride / Q000737:chemistry / Q000494:pharmacology; D051379:Mice; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000737:chemistry*; D012995:Solubility; D044004:Xanthones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*
C530094:1,2-dihydro-1,8,10-trihydroxy-2-(2-hydroxypropan-2-yl)-9-(3-methylbut-2-enyl)furo(3,2-a)xanthen-11-one; C530095:6-deoxy-7-demethylmangostanin; D016588:Anticarcinogenic Agents; D000975:Antioxidants; D006576:Heterocyclic Compounds, 4 or More Rings; D044004:Xanthones; D017665:Hydroxyl Radical; D008752:Methylene Chloride; D016660:NAD(P)H Dehydrogenase (Quinone)