xanthochymol and isoxanthochymol

The fruits of Garcinia xanthochymus can be eaten raw or processed into jams, preserves and vinegar. They provide not only vitamin and protein nutrients, but also pharmacologically active compounds, among which polycyclic polyprenylated acylphloroglucinols (PPAPs) are a major class. According to the literature, PPAPs exhibited good anti-cancer effects. This study investigated the antitumor effects and the underlying mechanism of S1 (the regioisomeric mixture of xanthochymol and guttiferone E) and S2 (the regioisomeric mixture of isoxanthochymol and cycloxanthochymol) isolated from the fruits of G. xanthochymus. In an H22 allograft mouse model, S1 and S2 could suppress the liver tumor growth and phosphorylation of STAT3. Computational modeling showed that S1 and S2 could form hydrogen bonds with the SH2 domain of STAT3. In HepG2 and MCF-7 cell lines, S1 and S2 downregulated the expression of p-STAT3

Topics: Animals; Antineoplastic Agents; Apoptosis; Benzophenones; Caspase 3; Cell Line, Tumor; Cyclin D1; Female; Fruit; Garcinia; Hep G2 Cells; Humans; Janus Kinase 2; Liver; Male; MCF-7 Cells; Mice; Molecular Docking Simulation; Phosphorylation; Plant Extracts; Signal Transduction; STAT3 Transcription Factor; Survivin

Topics: Benzophenones; Chromatography, High Pressure Liquid; Garcinia; Xanthones

A reverse-phase high-performance liquid chromatographic method was developed for qualitative and quantitative analysis of xanthochymol (1), and isoxanthochymol (2) in the fruit rinds, leaves and seed pericarps of Garcinia indica with confirmation using PDA detection and electrospray ionization MS. Absorption at 276 nm was chosen as the measuring wavelength at which resolution and baseline separation of compounds (1) and (2) could be obtained. The identity of the above two isomeric compounds (1) and (2) in the samples was unambiguously determined by their respective quasi-molecular ion [M - H]- in ESI-MS. Compounds (1) and (2) were qualitatively and quantitatively analyzed in the above three samples of Garcinia indica. The overall analytical procedure is rapid and reproducible and is considered for the analysis of the above two compounds.

Topics: Benzophenones; Chromatography, High Pressure Liquid; Fruit; Garcinia; Plant Leaves; Reproducibility of Results; Seeds; Spectrometry, Mass, Electrospray Ionization

The methanol extract of the fruit rinds of Garcinia indica showed potent cytotoxic activity against three human cancer cell lines, colon (COLO-320-DM), breast (MCF-7) and liver (WRL-68), as determined by the MTT assay. Fractionation of the methanol extract into hexane-, chloroform- and ethyl acetate-soluble fractions and evaluation of cytotoxic activity of each of the fractions revealed that the ethyl acetate fraction was the most effective as compared to the two other fractions. Two polyisoprenylated benzophenones, xanthochymol and isoxanthochymol, were isolated from the ethyl acetate fraction. Both xanthochymol and isoxanthochymol as a single pure entity did not turn out to be as effective as the ethyl acetate extract from which they have been isolated. The concentrations of xanthochymol and isoxanthochymol in four different extracts--methanol, hexane, chloroform and ethyl acetate--were determined with the help of LC-MS/MS. On the basis of the LC-MS/MS data, combinations of xanthochymol and isoxanthochymol in different ratios were tested in the MTT assay and were found to be effective. Moreover, it was established from the LC-MS/MS data that the combination of xanthochymol and isoxanthochymol in a ratio of 1 : 2 showed maximal cytotoxicity.

Topics: Antineoplastic Agents, Phytogenic; Benzophenones; Breast Neoplasms; Cell Line, Tumor; Chromatography, Liquid; Colonic Neoplasms; Garcinia; Humans; Liver Neoplasms; Molecular Structure; Phytotherapy; Tandem Mass Spectrometry

A sensitive liquid chromatography/electrospray ionization tandem mass spectrometrical (LC/ESI-MS/MS) method was developed for the identification and quantification of two polyisoprenylated benzophenones xanthochymol and isoxanthochymol in the extracts of the fruit rinds, stem bark, seed pericarps and leaves of Garcinia indica and in the fruit rinds of Garcinia cambogia. The separation of xanthochymol and isoxanthochymol was achieved on a RP-18 column using the solvent system consisting of a mixture of acetonitrile-water (9:1) and methanol-acetic acid (99.5:0.5) as a mobile phase at a flow rate of 0.4ml/min. A multiple reaction monitoring (MRM) method was developed for quantification of xanthochymol and isoxanthochymol in the above extracts of Garcinia species. On the basis of signal to noise ratio of 3, the limits of detection in MRM mode for xanthochymol and isoxanthochymol were 1.0ng/ml and 0.5ng/ml, respectively. The method was validated in terms of linearity, accuracy and precision for 6 days. The method developed was found to be useful for identification and quantification of xanthochymol and isoxanthochymol in the extracts of the fruit rinds, stem bark, seed pericarps and leaves of G. indica and in the fruit rinds of G. cambogia.

Topics: Benzophenones; Garcinia; Sensitivity and Specificity; Species Specificity; Spectrometry, Mass, Electrospray Ionization