Disease relevance of Spasfon-Lyoc

• Production of phenazine and phloroglucinol antibiotics, as examples, account for most of the natural defense provided by fluorescent Pseudomonas strains isolated from among the diversity of rhizobacteria associated with take-all decline [1].
• Purification and properties of phloroglucinol reductase from Eubacterium oxidoreducens G-41 [2].
• We previously reported that hyperforin (HF), a natural phloroglucinol purified from Saint John's wort, can induce the apoptosis of leukemic cells from patients with B-cell lymphocytic leukemia (B-CLL) ex vivo [3].
• A variety of phloroglucinol derivatives isolated from the pericarps of Mallotus japonicus were assessed for growth inhibiting activity against human larynx (HEp-2) and lung (PC-13) carcinoma cells as well as mouse B16 melanoma, leukemia P388, and L5178Y cells [4].
• A tentative degradative pathway for phloroglucinol by Rhodococcus sp. BPG--8 is proposed [5].

High impact information on Spasfon-Lyoc

• Drugs acting on visceral afferent pathways (octreotide and granisetron) did not modify this reflex, whereas the spasmolytic drug phloroglucinol inhibited phasic contractions without affecting tone [6].
• Furthermore, a polyketide synthase that resembles phloroglucinol synthase was detected [7].
• PhlD, a type III polyketide synthase from Pseudomonas fluorescens, catalyzes the synthesis of phloroglucinol from three molecules of malonyl-CoA [8].
• The enzyme is specific for phloroglucinol and NADPH [2].
• Substrate specificity of chalcone synthase from Petroselinum hortense. Formation of phloroglucinol derivatives from aliphatic substrates [9].

Chemical compound and disease context of Spasfon-Lyoc

• A rapid capillary electrophoretic (CE) method was developed for the determination of phloroglucinol compounds, monoacetylphloroglucinol (MAPG) and 2,4-diacetylphloroglucinol (DAPG), in microbial supernatants of Pseudomonas fluorescens F113 over a 24-h growth cycle [10].
• Metabolism of gallate and phloroglucinol in Eubacterium oxidoreducens via 3-hydroxy-5-oxohexanoate [11].

Biological context of Spasfon-Lyoc

• This compound is synthesized in three successive methylation steps from phloroglucinol, the initial precursor [12].
• The anti-HIV agent (+/-)-calanolide A (1) has been synthesized in a five-step approach starting with phloroglucinol [-->5-->6-->11-->18-->(+/-)-1], which includes Pechmann reaction, Friedel-Crafts acylation, chromenylation with 4,4-dimethoxy-2-methylbutan-2-ol, cyclization, and Luche reduction [13].
• A novel C3-symmetric scaffold has been efficiently synthesized exhibiting the property that variable receptor arms can be easily attached by simple alkylation reactions; the utility of the scaffold as a skeleton for large receptors has been examined with a corresponding tris(bipyridyl) derivative toward phloroglucinol [14].
• With the exception of the assay in which acetyl-CoA was used as the starter molecule, all substrates yielded a phloroglucinol derivative resulting from three sequential condensations of acetate units derived from three malonyl-CoA decarboxylations [15].
• Cytoprotective effect of phloroglucinol on oxidative stress induced cell damage via catalase activation [16].

Anatomical context of Spasfon-Lyoc

• AOPP enhanced the growth of cultured cells of Lonicera prolifera Rehd. while it inhibited the production of extracellular material that gave a positive reaction with phloroglucinol/HCl [17].
• We investigated the cytoprotective effect of phloroglucinol, which was isolated from Ecklonia cava (brown alga), against oxidative stress induced cell damage in Chinese hamster lung fibroblast (V79-4) cells [16].
• These results suggest that MJE and its phloroglucinol derivatives have the pharmacological ability to suppress PGE(2) production by activated macrophages [18].
• Prostaglandin E(2) production and induction of prostaglandin endoperoxide synthase-2 is inhibited in a murine macrophage-like cell line, RAW 264.7, by Mallotus japonicus phloroglucinol derivatives [18].

Associations of Spasfon-Lyoc with other chemical compounds

• Four novel phloroglucinol derivatives, garcinielliptones A (1), B (2), C (3), D (4), a novel triterpenoid, garcinielliptone E (5), and three known compounds were isolated from the seeds of Garcinia subelliptica [19].
• The equilibrium constant of the reaction was determined, and the free-energy change (delta G degree') of phloroglucinol formation from pyrogallol was calculated to be -15.5 kJ/mol [20].
• A crude (ECH) and a purified cyclohexane extract (HCP) of Hypericum caprifoliatum and their main phloroglucinol derivative (HC1) were evaluated regarding their action on monoaminergic systems, more precisely on dopamine [21].
• Hyperforin, a phloroglucinol derivative, is a major pharmacologically and therapeutically active constituent of Hypericum perforatum extract that is widely used as an herbal antidepressant drug [22].
• The same experiment is performed using the solute phloroglucinol (PG), which is not sorbed by PRP-infinity and serves as an "impulse response function marker" (IRF-Marker) [23].

Gene context of Spasfon-Lyoc

• Moreover, RT-PCR analysis showed that MJE and its phloroglucinol derivatives significantly suppressed PGHS-2 mRNA expression [18].
• However, induction of PGHS-2 in LPS-activated macrophages was inhibited by MJE and its phloroglucinol derivatives, whereas the level of PGHS-1 protein was not affected [18].
• We conclude that these phloroglucinol derivatives inhibit pro-inflammatory cytokine production and mRNA expression via suppression of NF-kappaB activation in activated macrophages [24].
• Furthermore, the inactivation of phlF results in derepression of phloroglucinol production in this strain [25].
• Garsubellin A, a novel polyprenylated phloroglucin derivative, increasing choline acetyltransferase (ChAT) activity in postnatal rat septal neuron cultures [26].

Analytical, diagnostic and therapeutic context of Spasfon-Lyoc

• Two adducts derived from (+)-catechin and three adducts from phloroglucinol were isolated and identified using reversed-phase high performance liquid chromatography (HPLC) and electrospray ionization mass spectrometry (ESI-MS) [27].
• Several of the phloroglucinol derivatives isolated from this tree were cytotoxic against the KB system and L-5178Y in cell culture [28].
• Culture filtrates of cells grown on phloroglucinol detected 1,2,3,5-tetrahydroxybenzene when extracted and analyzed using gas chromatography--mass spectrometry, thin-layer chromatography, and ultraviolet spectrophotometry [5].
• Degradation pathways were proposed based on the intermediates detected by high performance liquid chromatography (HPLC) and HPLC coupled with mass spectrometry (LC-MS) and the detection of enzymes that catalyze reactions such as taxifolin isomerization, phloretin hydrolysis and phloroglucinol reduction [29].
• Degradation was monitored by reversed-phase HPLC following acid-catalyzed cleavage in the presence of excess phloroglucinol (phloroglucinolysis) and by high-performance gel permeation chromatography [30].

References