A fast and efficient preparative method for separation and purification of main bioactive xanthones from the waste of Garcinia mangostana L. by high-speed countercurrent chromatography (original) (raw)
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Molecules
Xanthones are significant bioactive compounds and secondary metabolites in mangosteen pericarps. A xanthone is a phenolic compound and versatile scaffold that consists of a tricyclic xanthene-9-one structure. A xanthone may exist in glycosides, aglycones, monomers or polymers. It is well known that xanthones possess a multitude of beneficial properties, including antioxidant activity, anti-inflammatory activity, and antimicrobial properties. Additionally, xanthones can be used as raw material and/or an ingredient in many food, pharmaceutical, and cosmetic applications. Although xanthones can be used in various therapeutic and functional applications, their properties and stability are determined by their extraction procedures. Extracting high-quality xanthones from mangosteen with effective therapeutic effects could be challenging if the extraction method is insufficient. Although several extraction processes are in use today, their efficiency has not yet been rigorously evaluated. ...
Journal of Chromatography A, 2009
Xanthones are well known for their interesting phytochemical properties, which make them attractive to the pharmaceutical and medicinal industry. We have therefore developed a method to analyse the major xanthones in Garcina mangostana. The xanthones were extracted by pressurized liquid extraction with ethanol and separated at the semi-preparative scale by centrifugal partition chromatography (CPC) with a biphasic solvent system consisting of heptane/ethyl acetate/methanol/water (2:1:2:1, v/v/v/v). A CPC-electrospray ionisation MS coupling was performed and used to simultaneously separate and identify the compounds. Thanks to a variable flow splitter and an additional stream of ethanol/1 mol L −1 ammonium acetate (95:5, v/v), all the compounds were ionised, detected and monitored whatever the solvents used in mobile phase for the CPC separation. The dual mode or elution-extrusion which are less solvent-consuming and faster than the elution mode were used without loss of ionisation and detection.
Acta Chromatographica, 2020
Xanthones are well recognized as chemotaxonomic markers for the plants belonging to the genus Garcinia. Xanthones have many interesting pharmacological properties. Efficient extraction and rapid liquid chromatography methods are essentially required for qualitative and quantitative determination of xanthones in their natural sources. In the present investigation, fruit rinds extracts of 8 Garcinia species from India, were prepared with solvents of varying polarity. Identification and quantification of 3 xanthones, namely, α-mangostin, β-mangostin, and γ-mangostin in these extracts were carried out using a rapid and validated ultra-high-performance liquid chromatographyphotodiode array detection (UHPLC-PDA) method at 254 nm. γ-Mangostin (3.97 ± 0.05 min) was first eluted, and it was followed by α-mangostin (4.68 ± 0.03 min) and β-mangostin (5.60 ± 0.04 min). The calibration curve for α-mangostin, β-mangostin, and γmangostin was linear in the concentration range 0.781-100 μg/mL. α-Mangostin was quantified in all 4 extracts of Garcinia mangostana. Its content (%) in hexane, chloroform, ethyl acetate, and methanol extracts of G. mangostana was 10.36 ± 0.10, 4.88 ± 0.01, 3.98 ± 0.004, and 0.044 ± 0.002, respectively. However, the content of α-mangostin was below the limit of detection or limit of quantification in the extracts of other Garcinia species. Similarly, β-mangostin was quantified only in hexane (1.17 ± 0.01%), chloroform (0.39 ± 0.07%), and ethyl acetate (0.28 ± 0.03%) extracts of G. mangostana. γ-Mangostin was quantified in all 4 extracts of G. mangostana. Its content (%) in hexane, chloroform, ethyl acetate, and methanol extracts of G. mangostana was 0.84 ± 0.01, 1.04 ± 0.01, 0.63 ± 0.04, and 0.15 ± 0.01, respectively. γ-Mangostin was also quantified in hexane (0.09 ± 0.01), chloroform (0.05 ± 0.01), and ethyl acetate (0.03 ± 0.01) extracts of G. cowa, ethyl acetate extract of G. cambogia (0.02 ± 0.01), G. indica (0.03 ± 0.01), and G. loniceroides (0.07 ± 0.01). Similarly, γ-mangostin was quantified in 3 extracts of G. morella, namely, hexane (0.03 ± 0.01), chloroform (0.04 ± 0.01), and methanol (0.03 ± 0.01). In the case of G. xanthochymus, γ-mangostin was quantified in chloroform (0.03 ± 0.001) extract only. α-Mangostin and β-mangostin were not detected in any of 4 extracts of G. pedunculata.
Journal of Pharmaceutical and Biomedical Analysis, 2007
A method is developed for the analysis of allantoin, gallic acid, dihydromelittoside, loganin, paeoniflorin, benzoylpaeoniflorin, and paeonol in Liuwei Dihuang tablets by high-performance liquid chromatography (HPLC)-UV-mass spectrometry (MS)-MS. Gradient elution with methanol-acetonitrile-water-formic acid solvent system is employed in the HPLC-electrospray ionization-MS study. The positive-ion ESI mode is suitable for these compounds. The peaks of gallic acid, loganin, dihydromelittoside, paeoniflorin, benzoylpaeoniflorin, and paeonol are identified by their mass spectra and the fragments of their MS-MS spectra. Allantoin, gallic acid, loganin, paeoniflorin, and paeonol are simultaneously determined by UV detection at 210 nm for quantitative purposes.
Journal of Medicinal Plants Research, 2013
Garcinia mangostana (Guttiferae) is an important botanical source of xanthones; these compounds have remarkable pharmacological properties such as anti-cancer, anti-inflammatory and anti-microbial effects. Xanthones-rich extracts have been widely used in nutritional supplements, herbal cosmetics and pharmaceutical preparations. In order to maintain consistency of the pharmacological and clinical outcomes, standardization of crude extracts is crucial for quality control assurance. This study reports development and validation of a ultraviolet-visible (UV-Vis) spectrophotometric method for determination of total xanthones in various G. mangostana fruit rind extracts. The method was validated at 4 wavelengths viz. 243.4, 254, 316.4 and 320 nm. Linearity was in the range of 0.5 to 20 µg/ml; intra-day and inter-day precision, as a relative standard deviation, was 1.1 and 1.8%, respectively; accuracy, limit of detection (LOD) and limit of quantification (LOQ) were in the range of 99 to 10...
Food Chemistry, 2012
Attention on mangosteen fruits as an ingredient of functional products is growing, particularly due to their rich content of xanthones. Whereas mangosteen products containing puree from the entire fruit of Garcinia mangostana L. are considered as novel food in the European Union, such products are widely used in the US due to their high antioxidant potential and traditional consumption in their countries of origin. With special emphasise on the xanthone profile and content, mangosteen pericarp, aril segments and a functional beverage made from whole mangosteens were compared. The fruit parts and the product showed a consistent pattern composed of mainly 7 xanthones, which could be unambiguously identified by LC-MS. Based on collision-induced dissociation experiments, fragmentation pathways of xanthones were suggested. The quantification of 7 derivatives contained in the arils, the pericarp and the functional beverage allowed an estimation of the amounts of bioactives which are ingested by the consumption of fresh mangosteen fruits and beverages produced thereof. Total xanthone content of the pericarp was the highest, revealing its potential as functional ingredient-followed by the aril segments and the functional beverage. It has been shown, that the content of bioactive xanthones in 90 mL of the beverage (i.e. the recommended daily dose) corresponds to about 0.9 g of pericarp and the aril segments (%30 g) of a single mangosteen. Since residual parts of pericarp are always ingested after usual peeling of the fruit, xanthone concentrations exceeding those of the nutritional beverage have been ingested, thus allowing to establish a safe history of use.
Solvent Extraction Research and Development, Japan, 2013
The extraction of xanthones, such as α-mangostin from the pericarp of mangosteen (Garcinia mangostana Linn.) by supercritical fluid extraction (SFE), for which the solvent was carbon dioxide (CO 2), was carried out at 35, 40 and 50 ºC. The extraction pressure was from 10 to 20 MPa. In order to enhance the yield of the extraction, ethanol was added as an entrainer. The yields of xanthones, such as α-mangostin in the extraction were significantly improved, whereas a change in the selectivity of the extract was not observed. We also conducted qualitative and quantitative analyses for xanthones in the extract by HPLC, and analyzed the extraction behavior. The effect of three operating parameters, such as temperature, pressure and the mole fraction of ethanol in a supercritical solution of CO 2 on the extraction yield was investigated using the single-factor method.
Xanthones from Stem Bark of Garcinia rostrata
Chemistry of Natural Compounds, 2018
Garcinia is one of the genera under the family of Clusiaceae. It is well known to have good medicinal properties. Previous studies have reported Garcinia plants to have good antioxidant [1-3], antibacterial [4], anti-inflammatory [2, 5, 6], and anticancer [2, 7] activities. Major compounds in this genus are mostly xanthones, benzophenones, and flavonoids, which are responsible for their biological activities. Although Garcinia plants were well studied, there are still many yet to be harvested and studied to find their chemical constituents and biological activities. This paper reports on the xanthones isolated from the stem bark of Garcinia rostrata, a species never reported before, and its antibacterial activities. There are no previous reports on the chemistry of Garcinia rostrata. The n-hexane extract of Garcinia rostrata gave ananixanthone (1) [8]. 6-Deoxyjacareubin (2) [9], and 6-deoxyisojacareubin (3) [10], which were isolated from the chloroform extract of the same plant. The polar fraction of the chloroform extract yielded 8-deoxygartanin (4) [11] and 1,7-dihydroxyxanthone (5) [12]. Compound 4 was also isolated from the ethyl acetate extract of Garcinia rostrata. The ethyl acetate extract of Garcinia rostrata was fractionated using gravity column chromatography and a C 18 column to give 1,3,7-trihydroxyxanthone (6) [13]. Plant Material. Stem barks of plant samples of Garcinia rostrata were collected from Kuching,
Xanthones from Garcinia mangostana Linn. Pulp
In an earlier study, we isolated α-mangostin as the major xanthone and 3-isomangostin as a minor constituent of the pulp of the ripe fruit of Garcinia mangostana Linn. Further study on the pulp has led to the isolation of garcinone D (1). The structure of 1 was elucidated by extensive 1D and 2D NMR spectroscopy. Garcinone D was reported to exhibit anticancer property.