The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

phloroglucinol     benzene-1,3,5-triol

Synonyms: Floroglucin, Phloroglucin, Floroglucinol, Phloroglucine, Spasfon-Lyoc, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of Spasfon-Lyoc


High impact information on Spasfon-Lyoc


Chemical compound and disease context of Spasfon-Lyoc


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


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


Analytical, diagnostic and therapeutic context of Spasfon-Lyoc


  1. Molecular mechanisms of defense by rhizobacteria against root disease. Cook, R.J., Thomashow, L.S., Weller, D.M., Fujimoto, D., Mazzola, M., Bangera, G., Kim, D.S. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  2. Purification and properties of phloroglucinol reductase from Eubacterium oxidoreducens G-41. Haddock, J.D., Ferry, J.G. J. Biol. Chem. (1989) [Pubmed]
  3. Hyperforin inhibits MMP-9 secretion by B-CLL cells and microtubule formation by endothelial cells. Quiney, C., Billard, C., Mirshahi, P., Fourneron, J.D., Kolb, J.P. Leukemia (2006) [Pubmed]
  4. Cytotoxic and antitumor constituents in pericarps of Mallotus japonicus. Arisawa, M., Fujita, A., Morita, N., Koshimura, S. Planta Med. (1990) [Pubmed]
  5. 1,3,5-Trihydroxybenzene biodegradation by Rhodococcus sp. BPG-8. Armstrong, S., Patel, T.R. Can. J. Microbiol. (1993) [Pubmed]
  6. Intracolonic injection of glycerol: a model for abdominal pain in irritable bowel syndrome? Louvel, D., Delvaux, M., Staumont, G., Camman, F., Fioramonti, J., Bueno, L., Frexinos, J. Gastroenterology (1996) [Pubmed]
  7. Genome sequence of an industrial microorganism Streptomyces avermitilis: deducing the ability of producing secondary metabolites. Omura, S., Ikeda, H., Ishikawa, J., Hanamoto, A., Takahashi, C., Shinose, M., Takahashi, Y., Horikawa, H., Nakazawa, H., Osonoe, T., Kikuchi, H., Shiba, T., Sakaki, Y., Hattori, M. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  8. Characterization of the Substrate Specificity of PhlD, a Type III Polyketide Synthase from Pseudomonas fluorescens. Zha, W., Rubin-Pitel, S.B., Zhao, H. J. Biol. Chem. (2006) [Pubmed]
  9. Substrate specificity of chalcone synthase from Petroselinum hortense. Formation of phloroglucinol derivatives from aliphatic substrates. Schüz, R., Heller, W., Hahlbrock, K. J. Biol. Chem. (1983) [Pubmed]
  10. Rapid analysis of antimicrobial metabolites monoacetylphloroglucinol and 2,4-diacetylphloroglucinol using capillary zone electrophoresis. Guihen, E., Glennon, J.D., Cullinane, M., O'Gara, F. Electrophoresis (2004) [Pubmed]
  11. Metabolism of gallate and phloroglucinol in Eubacterium oxidoreducens via 3-hydroxy-5-oxohexanoate. Krumholz, L.R., Crawford, R.L., Hemling, M.E., Bryant, M.P. J. Bacteriol. (1987) [Pubmed]
  12. The key role of phloroglucinol O-methyltransferase in the biosynthesis of Rosa chinensis volatile 1,3,5-trimethoxybenzene. Wu, S., Watanabe, N., Mita, S., Dohra, H., Ueda, Y., Shibuya, M., Ebizuka, Y. Plant Physiol. (2004) [Pubmed]
  13. Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers. Flavin, M.T., Rizzo, J.D., Khilevich, A., Kucherenko, A., Sheinkman, A.K., Vilaychack, V., Lin, L., Chen, W., Greenwood, E.M., Pengsuparp, T., Pezzuto, J.M., Hughes, S.H., Flavin, T.M., Cibulski, M., Boulanger, W.A., Shone, R.L., Xu, Z.Q. J. Med. Chem. (1996) [Pubmed]
  14. A C3-symmetric molecular scaffold for the construction of large receptors. Haberhauer, G., Oeser, T., Rominger, F. Chem. Commun. (Camb.) (2004) [Pubmed]
  15. Molecular characterization of root-specific chalcone synthases from Cassia alata. Samappito, S., Page, J., Schmidt, J., De-Eknamkul, W., Kutchan, T.M. Planta (2002) [Pubmed]
  16. Cytoprotective effect of phloroglucinol on oxidative stress induced cell damage via catalase activation. Kang, K.A., Lee, K.H., Chae, S., Zhang, R., Jung, M.S., Ham, Y.M., Baik, J.S., Lee, N.H., Hyun, J.W. J. Cell. Biochem. (2006) [Pubmed]
  17. Inhibition of lignin formation by L-alpha-aminooxy-beta-phenylpropionic acid, an inhibitor of phenylalanine ammonia-lyase. Amrhein, N., Frank, G., Lemm, G., Luhmann, H.B. Eur. J. Cell Biol. (1983) [Pubmed]
  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. Ishii, R., Horie, M., Saito, K., Arisawa, M., Kitanaka, S. Biochim. Biophys. Acta (2002) [Pubmed]
  19. Novel and anti-inflammatory constituents of Garcinia subelliptica. Weng, J.R., Lin, C.N., Tsao, L.T., Wang, J.P. Chemistry (Weinheim an der Bergstrasse, Germany) (2003) [Pubmed]
  20. Pyrogallol-to-phloroglucinol conversion and other hydroxyl-transfer reactions catalyzed by cell extracts of Pelobacter acidigallici. Brune, A., Schink, B. J. Bacteriol. (1990) [Pubmed]
  21. The antidepressant-like effect of Hypericum caprifoliatum Cham & Schlecht (Guttiferae) on forced swimming test results from an inhibition of neuronal monoamine uptake. Viana, A., do Rego, J.C., von Poser, G., Ferraz, A., Heckler, A.P., Costentin, J., Kuze Rates, S.M. Neuropharmacology (2005) [Pubmed]
  22. Modulation of ion channels in rat neurons by the constituents of Hypericum perforatum. Krishtal, O., Lozovaya, N., Fisunov, A., Tsintsadze, T., Pankratov, Y., Kopanitsa, M., Chatterjee, S.S. Pharmacopsychiatry (2001) [Pubmed]
  23. Continuous desorption rate measurement from a shallow-bed of poly(styrene-divinylbenzene) particles with correction for experimental artifacts. Bujalski, R., Cantwell, F.F. Journal of chromatography. A. (2004) [Pubmed]
  24. Inhibition of lipopolysaccharide-induced pro-inflammatory cytokine expression via suppression of nuclear factor-kappaB activation by Mallotus japonicus phloroglucinol derivatives. Ishii, R., Horie, M., Saito, K., Arisawa, M., Kitanaka, S. Biochim. Biophys. Acta (2003) [Pubmed]
  25. Regulation of production of the antifungal metabolite 2,4-diacetylphloroglucinol in Pseudomonas fluorescens F113: genetic analysis of phlF as a transcriptional repressor. Delany, I., Sheehan, M.M., Fenton, A., Bardin, S., Aarons, S., O'Gara, F. Microbiology (Reading, Engl.) (2000) [Pubmed]
  26. Garsubellin A, a novel polyprenylated phloroglucin derivative, increasing choline acetyltransferase (ChAT) activity in postnatal rat septal neuron cultures. Fukuyama, Y., Kuwayama, A., Minami, H. Chem. Pharm. Bull. (1997) [Pubmed]
  27. ABTS radical-driven oxidation of polyphenols: isolation and structural elucidation of covalent adducts. Osman, A.M., Wong, K.K., Fernyhough, A. Biochem. Biophys. Res. Commun. (2006) [Pubmed]
  28. Studies on cytotoxic constituents in pericarps of Mallotus japonicus, Part I. Arisawa, M., Fujita, A., Suzuki, R., Hayashi, T., Morita, N., Kawano, N., Koshimura, S. J. Nat. Prod. (1985) [Pubmed]
  29. Transformation of flavonoids by intestinal microorganisms. Blaut, M., Schoefer, L., Braune, A. International journal for vitamin and nutrition research. Internationale Zeitschrift für Vitamin- und Ernährungsforschung. Journal international de vitaminologie et de nutrition. (2003) [Pubmed]
  30. Analysis of the oxidative degradation of proanthocyanidins under basic conditions. Jorgensen, E.M., Marin, A.B., Kennedy, J.A. J. Agric. Food Chem. (2004) [Pubmed]
WikiGenes - Universities