Nutraceutical composition from
Pharmaceutical, cosmetic, nutraceutical and dietary compositions derived from Garcinia mangostana are rich in γ-mangostin and other demethylated xanthones. These compositions exhibit potent antioxidative activity and reduce inflammation. These compositions may be used in a method of treating TNF-α, and aP2 mediated disorders. The compositions are prepared by subjecting a hydroalcoholic extract of fruit pericarp (fruit hull) of Garcinia mangostana , wherein said hydroalcoholic extract comprises predominantly α-mangostin, to demethylation in the presence of a Lewis acid, an organic base and a catalyst.
1. A process for producing a composition with antibacterial activity, comprising an enriched Garcinia mangostana extract, said process comprising the step of:
a) demethylating a hydroalcoholic extract of a fruit pericarp (fruit hull) of Garcinia mangostana in an organic solvent, wherein said hydroalcoholic extract comprises α-mangostin and minor amounts of other xanthones,
said demethylating being performed in the presence of a Lewis acid, an organic base, and a catalyst to yield composition-I enriched in demethylated xanthones,
wherein said composition-I comprises γ-mangostin in the range of 20% to 40% of total weight of composition-I, α-mangostin in the range of 0 to 3%, garcinone C in the range of 0.5 to 3% and 3-isomangostin in the range of 0.5 to 2.5%.
2. The process as claimed in claim 1 , wherein said Lewis acid used in said demethylating step is selected from the group consisting of aluminum chloride, aluminum bromide, aluminum iodide, boron tribromide, a boron trichloride-methyl sulfide complex, a sodium salt of N-methylaniline, sodium ethanethiolate, lithium chloride, beryllium chloride in dimethyl formamide, and a mixture thereof.
3. The process as claimed in claim 1 , wherein the catalyst used in said demethylating step is an alkali metal iodide, magnesium iodide, calcium iodide, or a phase transfer catalyst.
4. The process as claimed in claim 1 , wherein said composition-I is subjected to column chromatography to yield composition-II enriched in γ-mangostin in the range of about 50 to 70%.
5. The process as claimed in claim 1 , wherein said composition-I is subjected to silica gel/reversed phase flash column chromatography to yield composition-II enriched in γ-mangostin in the range of about 50 to 70%.
6. The process as claimed in claim 4 , wherein said composition-II is subjected to:
column chromatography over silica/reversed phase silica, and then
crystallization to yield composition-III comprising γ-mangostin in the range of 85-95%.
7. The process as claimed in claim 6 , further comprising a step of recrystallizing said composition-III repeatedly in methanol/dichloromethane solvent to obtain a solid containing up to 99% γ-mangostin.
8. The process as claimed in claim 4 , wherein subjecting said composition-I to column chromatography comprises:
dissolving said composition-I in an aqueous organic solvent and adjusting the pH to 10-10.5 with alkali solution, followed by
subjecting the solution of composition-I to a column chromatography by depositing the solution on a styrene-divinylbenzene resin column, eluting the column with water, followed by eluting the column with an organic solvent to obtain an organic fraction, and evaporating the organic solvent from the organic fraction to obtain composition-II,
wherein said composition-II comprises γ-mangostin in the range of 50% to 70% of the total weight of composition-II, α-mangostin in the range of 0 to 4%, garcinone C in the range of 0.5 to 4% and 3-isomangostin in the range of 0.5 to 4%.
9. The process as claimed in claim 8 , wherein said aqueous organic solvent contains an organic solvent selected from the group consisting of acetone, ethyl acetate, methanol, ethanol, isopropanol, and mixtures thereof.
10. The process as claimed in claim 8 , wherein said organic solvent used in said eluting is selected from the group consisting of acetone, ethyl acetate, methanol, ethanol, isopropanol, and mixtures thereof.
11. The process as claimed in claim 4 , wherein said Composition-II is dispersed into dichloromethane, followed by stirring the dichloromethane solution for 30 min, followed by filtration of insoluble solid material, and drying the insoluble solid material under vacuum to obtain composition-III;
wherein said composition-III comprises γ-mangostin in the range of 85% to 95% of the total weight of composition-III, α-mangostin in the range of 0 to 1%, garcinone C in the range of 0.1 to 2% and 3-isomangostin in the range of 0.1 to 2%.