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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
Chemical Compound Review

Pelargonidol     2-(4-hydroxyphenyl)chromene- 3,5,7-triol...

Synonyms: P1659_ALDRICH, CHEMBL591036, AG-J-59386, CHEBI:28510, P1659_SIGMA, ...
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Disease relevance of Pelargonidol chloride

 

High impact information on Pelargonidol chloride

  • Transformation of RL01 with a vector p35A1, containing the A1-complementary DNA behind the 35S promotor leads to red flowers of the pelargonidin-type [2].
  • Petunia does not produce orange flowers because dihydroflavonol 4-reductase (DFR) from this species, an enzyme involved in anthocyanin biosynthesis, inefficiently reduces dihydrokaempferol, the precursor to orange pelargonidin-type anthocyanins [3].
  • The transgenic petunia line 17-R contains one copy of the maize A1 gene which mediates brick-red pelargonidin pigmentation of the flower [4].
  • However, at concentrations > or = 50 microM, all anthocyanidins tested (delphinidin, cyanidin, malvidin, pelargonidin, and paeonidin), including those not interfering with topoisomerases, were found to induce DNA strand breaks in the comet assay [5].
  • Based on the results, we propose that RsPrx1 and orthologs are targeted to the vacuoles to modify stored anthocyanins like pelargonidin [6].
 

Biological context of Pelargonidol chloride

  • Furthermore, a correlation was found between the methylation status of the 35S RNA promoter and the instability of the floral pelargonidin coloration [7].
  • Peonidin and pelargonidin were identified after acid hydrolysis by comparison of the fragmentation patterns and retention times of the released aglycones with those of standard compounds [8].
  • The introduction of the maize A1 cDNA under the control of the CaMV 35S RNA promoter leads to the production of pelargonidin derivatives, resulting in a brick red flower phenotype [7].
  • A similar increase in methylation, specifically in the transgene region, was also observed among progeny of R101-17del, a deletion derivative of R101-17 that no longer produces pelargonidin pigments due to a deletion in the A1 coding region [9].
  • Absorption, tissue distribution and excretion of pelargonidin and its metabolites following oral administration to rats [10].
 

Associations of Pelargonidol chloride with other chemical compounds

 

Gene context of Pelargonidol chloride

  • By spectral and chemical methods, seven of the 10 pigments were determined to be pelargonidin 3-O-[2-O-(2-O-(acyl-I)-beta-D-xylopyranosyl)- 6-O-(acyl-II)-beta-D-glucopyranoside]-5-O-[6-O-(malonyl)-beta-D- glucopyranoside], in which acyl moieties varied between sinapic, ferulic, caffeic and p-coumaric acids [16].
  • Similarly, pelargonidin inhibited AGS, HCT-116, NCI H460, MCF-7 and SF-268 cell growth by 64, 63, 62, 63 and 34%, respectively, at 200 microg/mL [17].
  • Among the anthocyanins most effective in suppressing the tumor cell growth, cyanin and pelargonidin made a mild rise between the 1st and 2nd peak suggesting block between G1 and S phase [18].
 

Analytical, diagnostic and therapeutic context of Pelargonidol chloride

  • Pel was reacted with ONOO(-), then the reaction mixture was analyzed using high-performance liquid chromatography (HPLC) [11].
  • Based on HPLC and LC-MS analyses we demonstrate that pelargonidin is absorbed and present in plasma following oral gavage to rats [10].

References

  1. Metabolic engineering of anthocyanin biosynthesis in Escherichia coli. Yan, Y., Chemler, J., Huang, L., Martens, S., Koffas, M.A. Appl. Environ. Microbiol. (2005) [Pubmed]
  2. A new petunia flower colour generated by transformation of a mutant with a maize gene. Meyer, P., Heidmann, I., Forkmann, G., Saedler, H. Nature (1987) [Pubmed]
  3. Alteration of a single amino acid changes the substrate specificity of dihydroflavonol 4-reductase. Johnson, E.T., Ryu, S., Yi, H., Shin, B., Cheong, H., Choi, G. Plant J. (2001) [Pubmed]
  4. Differences in DNA-methylation are associated with a paramutation phenomenon in transgenic petunia. Meyer, P., Heidmann, I., Niedenhof, I. Plant J. (1993) [Pubmed]
  5. Anthocyanidins modulate the activity of human DNA topoisomerases I and II and affect cellular DNA integrity. Habermeyer, M., Fritz, J., Barthelmes, H.U., Christensen, M.O., Larsen, M.K., Boege, F., Marko, D. Chem. Res. Toxicol. (2005) [Pubmed]
  6. Purification and cloning of a Chinese red radish peroxidase that metabolise pelargonidin and forms a gene family in Brassicaceae. Wang, L., Burhenne, K., Kristensen, B.K., Rasmussen, S.K. Gene (2004) [Pubmed]
  7. Epigenetic changes in the expression of the maize A1 gene in Petunia hybrida: role of numbers of integrated gene copies and state of methylation. Linn, F., Heidmann, I., Saedler, H., Meyer, P. Mol. Gen. Genet. (1990) [Pubmed]
  8. Detection of peonidin and pelargonidin glycosides in black carrots (Daucus carota ssp. sativus var. atrorubens Alef.) by high-performance liquid chromatography/electrospray ionization mass spectrometry. Kammerer, D., Carle, R., Schieber, A. Rapid Commun. Mass Spectrom. (2003) [Pubmed]
  9. Epigenetic variants of a transgenic petunia line show hypermethylation in transgene DNA: an indication for specific recognition of foreign DNA in transgenic plants. Meyer, P., Heidmann, I. Mol. Gen. Genet. (1994) [Pubmed]
  10. Absorption, tissue distribution and excretion of pelargonidin and its metabolites following oral administration to rats. El Mohsen, M.A., Marks, J., Kuhnle, G., Moore, K., Debnam, E., Kaila Srai, S., Rice-Evans, C., Spencer, J.P. Br. J. Nutr. (2006) [Pubmed]
  11. Mechanism for the peroxynitrite scavenging activity by anthocyanins. Tsuda, T., Kato, Y., Osawa, T. FEBS Lett. (2000) [Pubmed]
  12. Candidate gene analysis of anthocyanin pigmentation loci in the Solanaceae. De Jong, W.S., Eannetta, N.T., De Jong, D.M., Bodis, M. Theor. Appl. Genet. (2004) [Pubmed]
  13. Pomegranate fruit extract modulates UV-B-mediated phosphorylation of mitogen-activated protein kinases and activation of nuclear factor kappa B in normal human epidermal keratinocytes paragraph sign. Afaq, F., Malik, A., Syed, D., Maes, D., Matsui, M.S., Mukhtar, H. Photochem. Photobiol. (2005) [Pubmed]
  14. Determination of anthocyanidins in berries and red wine by high-performance liquid chromatography. Nyman, N.A., Kumpulainen, J.T. J. Agric. Food Chem. (2001) [Pubmed]
  15. Flavonoids in flowers of 16 Kalanchoë blossfeldiana varieties. Nielsen, A.H., Olsen, C.E., Møller, B.L. Phytochemistry (2005) [Pubmed]
  16. Acylated pelargonidin 3-sambubioside-5-glucosides in Matthiola incana. Saito, N., Tatsuzawa, F., Hongo, A., Win, K.W., Yokoi, M., Shigihara, A., Honda, T. Phytochemistry (1996) [Pubmed]
  17. Human tumor cell growth inhibition by nontoxic anthocyanidins, the pigments in fruits and vegetables. Zhang, Y., Vareed, S.K., Nair, M.G. Life Sci. (2005) [Pubmed]
  18. Influence of flavonoids on cell cycle phase as analyzed by flow-cytometry. Koide, T., Kamei, H., Hashimoto, Y., Kojima, T., Terabe, K., Umeda, T. Cancer Biother. Radiopharm. (1997) [Pubmed]
 
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