guttiferone-e and xanthochymol

Brazilian green and red propolis stand out as commercial products for different medical applications. In this article, we report the antimicrobial activities of the hydroalcoholic extracts of green (EGP) and red (ERP) propolis, as well as guttiferone E plus xanthochymol (8) and oblongifolin B (9) from red propolis, against multidrug-resistant bacteria (MDRB). We undertook the minimal inhibitory (MIC) and bactericidal (MBC) concentrations, inhibition of biofilm formation (MICB

Topics: Anti-Infective Agents; Bacterial Proteins; Benzophenones; Binding Sites; Biofilms; Brazil; Catalase; Catalytic Domain; Drug Resistance, Multiple, Bacterial; Microbial Sensitivity Tests; Molecular Docking Simulation; Propolis; Staphylococcus aureus

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: Apoptosis; bcl-2-Associated X Protein; Benzophenones; Cell Cycle Checkpoints; Cell Line, Tumor; Cyclin D1; Cytotoxins; Humans; Leukemia; Magnetic Resonance Spectroscopy; Molecular Structure; Polycyclic Compounds; Proto-Oncogene Proteins c-bcl-2; Resting Phase, Cell Cycle; Spectrometry, Mass, Electrospray Ionization

Xanthochymol (XCM) and guttiferone E (GFE), a pair of π bond benzophenone isomers from Garcinia xanthochymus, were once reported to be difficult or impossible to separate. The present study reports the successful separation of these two isomers through high performance liquid chromatography (HPLC), as well as their effective isolation using high speed counter-current chromatography (HSCCC) based on the silver nitrate (AgNO

Topics: Benzophenones; Chromatography, High Pressure Liquid; Countercurrent Distribution; Garcinia; Magnetic Resonance Spectroscopy; Mass Spectrometry; Plant Extracts; Silver Nitrate

Polyisoprenylated benzophenones derived from Garcinia xanthochymus have cytotoxic activity in vitro and antitumor activity in rodent models, but the mechanism is unknown. The purpose of our study was to examine in parallel molecular pathways that are targeted by 3 Garcinia-derived benzophenones-xanthochymol (X), guttiferone E (GE) and guttiferone H (GH), in 3 human colon cancer cell lines, HCT116, HT29 and SW480. The IC50 concentrations were determined and the cells were then treated with X, GE or GH at their respective IC50 or IC50x2 concentrations. Effects on the cell cycle, mitochondrial membrane potential and apoptosis were assessed by flow cytometry and caspase activation. Changes in gene expression were assessed with Illumina 24 K gene arrays. We found that X, GE and GH induced loss of mitochondrial membrane potential and G1 arrest at their IC50 concentrations and induced caspase activation at IC50 x 2 concentrations. An analysis of the changes in gene expression revealed that with all 3 compounds and all 3 cell lines there was a marked increase in expression of several genes, including XBP1, ATF4 and DDIT3/CHOP, which are components of the endoplasmic reticulum stress response. The DDIT4/REDD1 gene, an inhibitor of the mTOR survival pathway, was also up-regulated. Therefore, X, GE and GH appear to inhibit the growth of human colon cancer cells, at least in part, by activating the endoplasmic reticulum stress response and inhibiting the mTOR cell survival pathway. These combined effects may contribute to the anticancer activity of these novel compounds.

Topics: Activating Transcription Factor 4; Apoptosis; Benzophenones; Caspases; Cell Cycle; Cell Line, Tumor; Cell Survival; Colonic Neoplasms; DNA-Binding Proteins; Endoplasmic Reticulum; Garcinia; Gene Expression Regulation, Neoplastic; HCT116 Cells; HT29 Cells; Humans; Inhibitory Concentration 50; Linear Models; Mitochondrial Membranes; Nuclear Proteins; Prenylation; Protein Kinases; Reactive Oxygen Species; Regulatory Factor X Transcription Factors; Signal Transduction; TOR Serine-Threonine Kinases; Transcription Factor CHOP; Transcription Factors; Up-Regulation; X-Box Binding Protein 1

Microtubule disassembly inhibitory properties have been established for the known polyisoprenylated benzophenones xanthochymol (1a) and guttiferone E (1b). The compounds were isolated from the fruits of Garcinia pyrifera collected in Malaysia. A structure-activity relationship study, including natural and semisynthetic derivatives, delineated some structural features necessary for the interaction with tubulin within this compound class.

Topics: Benzophenones; Butadienes; Chromatography, Gel; Chromatography, High Pressure Liquid; Fruit; Gas Chromatography-Mass Spectrometry; Hemiterpenes; Humans; KB Cells; Magnetic Resonance Spectroscopy; Malaysia; Microtubules; Optical Rotation; Pentanes; Plants, Medicinal; Rosales; Spectrophotometry, Infrared; Spectrophotometry, Ultraviolet; Structure-Activity Relationship; Tubulin