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Chemical Compound Review

Capsanthin     (2E,4E,6E,8E,10E,12E,14E,16E,1 8E)-19-[(4S)...

Synonyms: UPCMLD-DP025, CHEBI:3375, AC1NQY83, LS-48670, LMPR01070265, ...
 
 
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Disease relevance of Paprika extract

 

High impact information on Paprika extract

  • The amino acid sequence of B is similar to capsanthin-capsorubin synthase, an enzyme that produces red xanthophylls in fruits of pepper (Capsicum annum) [4].
  • Analysis of the capsanthin-capsorubin synthase promoter in combination with a beta-glucuronidase reporter gene reveals strong activation in transformed pepper protoplasts challenged with the above ROS [5].
  • Similarly, down-regulation of catalase by amitrole induces expression of carotenogenic gene mRNAs leading to the synthesis of capsanthin in excised green pericarp discs [5].
  • In contrast to the situation prevailing in chromoplasts, capsanthin was not esterified and its increased level was balanced by a concomitant decrease of the major leaf xanthophylls, suggesting an autoregulatory control of chloroplast carotenoid composition [6].
  • The biosynthesis of leaf carotenoids in Nicotiana benthamiana was altered by forced re-routing of the pathway to the synthesis of capsanthin, a non-native chromoplast-specific xanthophyll, using an RNA viral vector containing capsanthin-capsorubin synthase (Ccs) cDNA [6].
 

Biological context of Paprika extract

  • Leaves from transfected plants expressing Ccs developed an orange phenotype and accumulated high levels of capsanthin (up to 36% of total carotenoids) [6].
  • The pharmacokinetics of dietary capsanthin was measured in four male volunteers to assess the bioavailability of oxygenated carotenoids (xanthophylls) [7].
  • The areas under the curves (AUC) for capsanthin between 0 and 74 h and for lycopene between 0 and 72 h were 4.68 +/- 1.22 and 0.81 +/- 0.17(micromol.h)/L, respectively [7].
  • While the capsanthin-capsorubin synthase gene is uninterrupted, the fibrillin gene is interrupted by two introns, the first one being inefficiently spliced [8].
 

Anatomical context of Paprika extract

 

Associations of Paprika extract with other chemical compounds

 

Gene context of Paprika extract

  • Capsanthin was distributed in the plasma lipoproteins (VLDL, 13 +/- 3%; LDL , 44 +/- 3%; HDL, 43 +/- 3%) at the end of the experiment [7].
  • Supplementing capsanthin-rich paprika juice for 1 wk (equivalent to three doses of 5.4 micromol capsanthin/d; 16.2 micromol/d), the level of capsanthin reached a plateau (0.10-0.12 micromol/L) between d 2 and 7 and was not detectable by d 16 [7].
  • In the present study, the cultivar Mana had the highest total carotenoid content (13 208 mg/kg dwt), but the lowest R/Y (1.25) and Caps/Zeax (3.38) ratios, which are therefore the parameters to improve [13].
 

Analytical, diagnostic and therapeutic context of Paprika extract

  • The number of colonic aberrant crypt foci, preneoplastic lesions, at Week 6 was significantly fewer (by 42%) in the 0.2 mg capsanthin group, but not in other groups, than the control group [1].
  • To unequivocally identify plasma carotenoids, liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry analysis was applied, which had never been used as an analytical tool to evaluate the carotenoids of chicken plasma; HPLC chromatograms of chicken plasma following capsanthin feeding have not been presented [14].
  • Quantification of carotenoids in chicken plasma after feeding free or esterified lutein and capsanthin using high-performance liquid chromatography and liquid chromatography-mass spectrometry analysis [14].

References

  1. Prevention of N-methylnitrosourea-induced colon carcinogenesis in rats by oxygenated carotenoid capsanthin and capsanthin-rich paprika juice. Narisawa, T., Fukaura, Y., Hasebe, M., Nomura, S., Oshima, S., Inakuma, T. Proc. Soc. Exp. Biol. Med. (2000) [Pubmed]
  2. Cancer chemopreventive activity of carotenoids in the fruits of red paprika Capsicum annuum L. Maoka, T., Mochida, K., Kozuka, M., Ito, Y., Fujiwara, Y., Hashimoto, K., Enjo, F., Ogata, M., Nobukuni, Y., Tokuda, H., Nishino, H. Cancer Lett. (2001) [Pubmed]
  3. Modulation of multidrug resistance and apoptosis of cancer cells by selected carotenoids. Molnár, J., Gyémánt, N., Mucsi, I., Molnár, A., Szabó, M., Körtvélyesi, T., Varga, A., Molnár, P., Tóth, G. In Vivo (2004) [Pubmed]
  4. An alternative pathway to beta -carotene formation in plant chromoplasts discovered by map-based cloning of beta and old-gold color mutations in tomato. Ronen, G., Carmel-Goren, L., Zamir, D., Hirschberg, J. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  5. Induction and control of chromoplast-specific carotenoid genes by oxidative stress. Bouvier, F., Backhaus, R.A., Camara, B. J. Biol. Chem. (1998) [Pubmed]
  6. Functional integration of non-native carotenoids into chloroplasts by viral-derived expression of capsanthin-capsorubin synthase in Nicotiana benthamiana. Kumagai, M.H., Keller, Y., Bouvier, F., Clary, D., Camara, B. Plant J. (1998) [Pubmed]
  7. Accumulation and clearance of capsanthin in blood plasma after the ingestion of paprika juice in men. Oshima, S., Sakamoto, H., Ishiguro, Y., Terao, J. J. Nutr. (1997) [Pubmed]
  8. Structure and expression of two plant genes encoding chromoplast-specific proteins: occurrence of partially spliced transcripts. Deruère, J., Bouvier, F., Steppuhn, J., Klein, A., Camara, B., Kuntz, M. Biochem. Biophys. Res. Commun. (1994) [Pubmed]
  9. Xanthophyll biosynthesis in chromoplasts: isolation and molecular cloning of an enzyme catalyzing the conversion of 5,6-epoxycarotenoid into ketocarotenoid. Bouvier, F., Hugueney, P., d'Harlingue, A., Kuntz, M., Camara, B. Plant J. (1994) [Pubmed]
  10. Incorporation of carotenoids from paprika oleoresin into human chylomicrons. Pérez-Gálvez, A., Martin, H.D., Sies, H., Stahl, W. Br. J. Nutr. (2003) [Pubmed]
  11. A study on the toxicity of natural food dyes--toxicity and enzyme inhibition in Paramecium caudatum. Sako, F., Kobayashi, N., Taniguchi, N., Takakuwa, E. The Journal of toxicological sciences. (1978) [Pubmed]
  12. Effect of ascorbic acid on the stability of beta-carotene and capsanthin in paprika (Capsicum annuum) powder. Morais, H., Rodrigues, P., Ramos, C., Forgács, E., Cserháti, T., Oliveira, J. Die Nahrung. (2002) [Pubmed]
  13. Carotenoid biosynthesis changes in five red pepper (Capsicum annuum L.) cultivars during ripening. Cultivar selection for breeding. Hornero-Méndez, D., Gómez-Ladrón De Guevara, R., Mínguez-Mosquera, M.I. J. Agric. Food Chem. (2000) [Pubmed]
  14. Quantification of carotenoids in chicken plasma after feeding free or esterified lutein and capsanthin using high-performance liquid chromatography and liquid chromatography-mass spectrometry analysis. Breithaupt, D.E., Weller, P., Grashorn, M.A. Poult. Sci. (2003) [Pubmed]
 
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