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Chemical Compound Review

C13431     (1R,3S)-6-[18-[(1R,3S,6S)-3- hydroxy-1,5,5...

Synonyms:
 
 
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Disease relevance of C13431

 

High impact information on C13431

  • Wild-type tomato (Solanum lycopersicum) flowers are intensely yellow due to accumulation of the xanthophylls neoxanthin and violaxanthin [4].
  • Neoxanthin insertion into light-harvesting chlorophyll-a/b complex prefolded from overexpressed apoprotein (Lhcb1*2 from Pisum sativum) in the presence of chlorophylls a, b, and lutein as the sole carotenoid is kinetically controlled by an activation energy barrier of approximately 120 kJ mol(-1) [5].
  • Assembly of the major light-harvesting chlorophyll-a/b Complex: Thermodynamics and kinetics of neoxanthin binding [5].
  • Neoxanthin is bound to a distinct site (N1) that is highly selective for this species and whose occupancy is not essential for protein folding [6].
  • In the present study, we investigated the gastrointestinal metabolism of neoxanthin in mice and the in vitro digestion of spinach, and estimated the antiproliferative effect of neoxanthin metabolites on PC-3 human prostate cancer cells [7].
 

Biological context of C13431

  • The neoxanthin binding site of the major light harvesting complex (LHCII) from higher plants [8].
  • These results indicate that dietary neoxanthin is partially converted into (R/S)-neochrome by intragastric acidity before intestinal absorption and that (R/S)-neochrome exhibits an antiproliferative effect on PC-3 cells by the induction of cytostasis [7].
  • Although neoxanthin induced evident apoptotic cell death, (R/S)-neochrome inhibited the cell proliferation without obvious apoptosis induction [7].
  • Neoxanthin complexes (containing 30-50% of the all-trans isomer) disintegrate during electrophoresis, exhibit a largely reduced resistance against proteolytic attack; in addition, energy transfer from Chl b to Chl a is easily disrupted at elevated temperature [9].
  • When the leaf water potential was -2MPa (severe water deficit), there was nearly complete inhibition of photosynthesis apart from a decrease in chlorophylls, beta-carotene, neoxanthin and lutein [10].
 

Anatomical context of C13431

 

Associations of C13431 with other chemical compounds

 

Gene context of C13431

  • However, neoxanthin did not inhibit ODC activity when animals were treated with neoxanthin one hour before the application of DMBA in two-stage carcinogenesis, and there was no subsequent tumor formation [13].
  • We conclude that neoxanthin strongly modifies the electronic states of the nearby Chl b molecules causing a large electrooptical response at 650 nm stemming from one or more Chls b in the control samples [14].
 

Analytical, diagnostic and therapeutic context of C13431

References

  1. Carotenoids affect proliferation of human prostate cancer cells. Kotake-Nara, E., Kushiro, M., Zhang, H., Sugawara, T., Miyashita, K., Nagao, A. J. Nutr. (2001) [Pubmed]
  2. Identification of neoxanthin synthase as a carotenoid cyclase paralog. Bouvier, F., D'harlingue, A., Backhaus, R.A., Kumagai, M.H., Camara, B. Eur. J. Biochem. (2000) [Pubmed]
  3. Comparative immunological detection of lipids and carotenoids on peptides of photosystem I from higher plants and cyanobacteria. Makewicz, A., Radunz, A., Schmid, G.H. Z. Naturforsch., C, J. Biosci. (1996) [Pubmed]
  4. A chromoplast-specific carotenoid biosynthesis pathway is revealed by cloning of the tomato white-flower locus. Galpaz, N., Ronen, G., Khalfa, Z., Zamir, D., Hirschberg, J. Plant Cell (2006) [Pubmed]
  5. Assembly of the major light-harvesting chlorophyll-a/b Complex: Thermodynamics and kinetics of neoxanthin binding. Hobe, S., Trostmann, I., Raunser, S., Paulsen, H. J. Biol. Chem. (2006) [Pubmed]
  6. Carotenoid-binding sites of the major light-harvesting complex II of higher plants. Croce, R., Weiss, S., Bassi, R. J. Biol. Chem. (1999) [Pubmed]
  7. An epoxide-furanoid rearrangement of spinach neoxanthin occurs in the gastrointestinal tract of mice and in vitro: formation and cytostatic activity of neochrome stereoisomers. Asai, A., Terasaki, M., Nagao, A. J. Nutr. (2004) [Pubmed]
  8. The neoxanthin binding site of the major light harvesting complex (LHCII) from higher plants. Croce, R., Remelli, R., Varotto, C., Breton, J., Bassi, R. FEBS Lett. (1999) [Pubmed]
  9. Carotenoid binding sites in LHCIIb. Relative affinities towards major xanthophylls of higher plants. Hobe, S., Niemeier, H., Bender, A., Paulsen, H. Eur. J. Biochem. (2000) [Pubmed]
  10. Water deficit induced oxidative damage in tea (Camellia sinensis) plants. Jeyaramrajaa, P.R., Meenakshi, S.N., Kumar, R.S., Joshi, S.D., Ramasubramanian, B. J. Plant Physiol. (2005) [Pubmed]
  11. The effect of antibodies to neoxanthin on electron transport on the oxygen evolving side of photosystem II and the reactions of this antiserum with variuos chloroplast preparations. Radunz, A., Schmid, G.H. Z. Naturforsch., C, Biosci. (1975) [Pubmed]
  12. Seasonal changes in photosynthesis and photoprotection in a Quercus ilex subsp. ballota woodland located in its upper altitudinal extreme in the Iberian Peninsula. Corcuera, L., Morales, F., Abadía, A., Gil-Pelegrín, E. Tree Physiol. (2005) [Pubmed]
  13. The inhibition of DMBA-induced carcinogenesis by neoxanthin in hamster buccal pouch. Chang, J.M., CHen, W.C., Hong, D., Lin, J.K. Nutrition and cancer. (1995) [Pubmed]
  14. Stark effect measurements on monomers and trimers of reconstituted light-harvesting complex II of plants. Palacios, M.A., Caffarri, S., Bassi, R., van Grondelle, R., Amerongen Hv, H. Biochim. Biophys. Acta (2004) [Pubmed]
  15. Identification and aroma impact of norisoprenoids in orange juice. Mahattanatawee, K., Rouseff, R., Valim, M.F., Naim, M. J. Agric. Food Chem. (2005) [Pubmed]
 
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