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Chemical Compound Review

retinol     (2E,4E,6E,8E)-3,7-dimethyl-9- (2,6,6...

Synonyms: Alphalin, Aquasola, Prepalin, Retinolo, Testavol, ...
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Disease relevance of retinol


Psychiatry related information on retinol


High impact information on retinol

  • Apoptosis induced by vitamin A signaling is crucial for connecting the ureters to the bladder [12].
  • We show that the common nephric duct does not differentiate into the trigone but instead undergoes apoptosis, a crucial step for ureter transposition controlled by vitamin A-induced signals from the primitive bladder [12].
  • Rara(-/-) Rarb2(-/-) mice display impaired vitamin A signaling and develop syndromic urogenital malformations similar to those that occur in humans, including renal hypoplasia, hydronephrosis and mega-ureter, abnormalities also seen in mice with mutations in the proto-oncogene Ret [13].
  • Here we show that a single maternal administration of a low dose of the vitamin A metabolite retinoic acid is sufficient to compensate the requirement for Hoxa1 function [14].
  • Our studies indicate the presence of a new reciprocal signaling loop between the ureteric bud epithelium and the stromal mesenchyme, dependent on Ret and vitamin A. In the first part of the loop, vitamin-A-dependent signals secreted by stromal cells control Ret expression in the ureteric bud [15].

Chemical compound and disease context of retinol


Biological context of retinol


Anatomical context of retinol

  • Nutritional night blindness is thus part of the pathophysiology of this genetic disease and vitamin A supplementation can lead to dramatic restoration of photoreceptor function [2].
  • Regulation of terminal differentiation of cultured human keratinocytes by vitamin A [23].
  • Mutation of RPE65 can cause severe blindness from birth or early childhood, and RPE65 protein is associated with retinal pigment epithelium (RPE) vitamin A metabolism [24].
  • This paper reports the effect of vitamin A and its derivatives, the retinoids, on plasminogen activator (PA) synthesis in chick embryo fibroblast cultures (CEF) [25].
  • These results identify a temporal window of susceptibility to retinoids that is critical for mammalian inner ear specification, and provide the first evidence that a subteratogenic dose of vitamin A derivative can be effective in rescuing a congenital defect in the mammalian embryo [14].

Associations of retinol with other chemical compounds


Gene context of retinol

  • These malformations belong to the fetal vitamin A deficiency syndrome, supporting the idea that RXR alpha is involved in retinoid signaling in vivo [31].
  • Vitamin A controls epithelial/mesenchymal interactions through Ret expression [15].
  • In contrast to other genes whose defects have been implicated in degenerative retinopathies, RPE65 is the first disease gene in this group of inherited disorders that is expressed exclusively in the RPE, and may play a role in vitamin-A metabolism of the retina [32].
  • In a SFD family with a novel TIMP3 point mutation, we tested a hypothesis that their night blindness is due to a chronic deprivation of vitamin A at the level of the photoreceptors caused by a thickened membrane barrier between the photoreceptor layer and its blood supply [2].
  • These results suggest two vitamin A-mediated regulation steps in IFN-gamma gene expression: positive regulation of IFN-gamma transcript levels, and negative regulation posttranscriptionally [33].
  • We demonstrate that SANTA MARIA functions upstream of vitamin A formation in neurons and glia, which are outside of the retina [34].

Analytical, diagnostic and therapeutic context of retinol


  1. Vitamin A transport in human vitamin A toxicity. Smith, F.R., Goodman, D.S. N. Engl. J. Med. (1976) [Pubmed]
  2. Night blindness in Sorsby's fundus dystrophy reversed by vitamin A. Jacobson, S.G., Cideciyan, A.V., Regunath, G., Rodriguez, F.J., Vandenburgh, K., Sheffield, V.C., Stone, E.M. Nat. Genet. (1995) [Pubmed]
  3. Serum beta-carotene, vitamins A and E, selenium, and the risk of lung cancer. Menkes, M.S., Comstock, G.W., Vuilleumier, J.P., Helsing, K.J., Rider, A.A., Brookmeyer, R. N. Engl. J. Med. (1986) [Pubmed]
  4. A prospective study of the intake of vitamins C, E, and A and the risk of breast cancer. Hunter, D.J., Manson, J.E., Colditz, G.A., Stampfer, M.J., Rosner, B., Hennekens, C.H., Speizer, F.E., Willett, W.C. N. Engl. J. Med. (1993) [Pubmed]
  5. Vitamin A supplementation for extremely-low-birth-weight infants. National Institute of Child Health and Human Development Neonatal Research Network. Tyson, J.E., Wright, L.L., Oh, W., Kennedy, K.A., Mele, L., Ehrenkranz, R.A., Stoll, B.J., Lemons, J.A., Stevenson, D.K., Bauer, C.R., Korones, S.B., Fanaroff, A.A. N. Engl. J. Med. (1999) [Pubmed]
  6. Vitamin A, retinol, and carotenoids and the risk of gastric cancer: a prospective cohort study. Larsson, S.C., Bergkvist, L., Näslund, I., Rutegård, J., Wolk, A. Am. J. Clin. Nutr. (2007) [Pubmed]
  7. Vitamin A deficiency decreases and high dietary vitamin A increases disease severity in the mouse model of asthma. Schuster, G.U., Kenyon, N.J., Stephensen, C.B. J. Immunol. (2008) [Pubmed]
  8. Megavitamins for minimal brain dysfunction. A potentially dangerous therapy. Shaywitz, B.A., Siegel, N.J., Pearson, H.A. JAMA (1977) [Pubmed]
  9. Alcoholic liver injury in baboons: transformation of lipocytes to transitional cells. Mak, K.M., Leo, M.A., Lieber, C.S. Gastroenterology (1984) [Pubmed]
  10. Evidence for defective retinoid transport and function in late onset Alzheimer's disease. Goodman, A.B., Pardee, A.B. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  11. Taste perception in cirrhosis: its relationship to circulating micronutrients and food preferences. Madden, A.M., Bradbury, W., Morgan, M.Y. Hepatology (1997) [Pubmed]
  12. Apoptosis induced by vitamin A signaling is crucial for connecting the ureters to the bladder. Batourina, E., Tsai, S., Lambert, S., Sprenkle, P., Viana, R., Dutta, S., Hensle, T., Wang, F., Niederreither, K., McMahon, A.P., Carroll, T.J., Mendelsohn, C.L. Nat. Genet. (2005) [Pubmed]
  13. Distal ureter morphogenesis depends on epithelial cell remodeling mediated by vitamin A and Ret. Batourina, E., Choi, C., Paragas, N., Bello, N., Hensle, T., Costantini, F.D., Schuchardt, A., Bacallao, R.L., Mendelsohn, C.L. Nat. Genet. (2002) [Pubmed]
  14. Retinoic acid rescues inner ear defects in Hoxa1 deficient mice. Pasqualetti, M., Neun, R., Davenne, M., Rijli, F.M. Nat. Genet. (2001) [Pubmed]
  15. Vitamin A controls epithelial/mesenchymal interactions through Ret expression. Batourina, E., Gim, S., Bello, N., Shy, M., Clagett-Dame, M., Srinivas, S., Costantini, F., Mendelsohn, C. Nat. Genet. (2001) [Pubmed]
  16. Decreased expression of N-myc precedes retinoic acid-induced morphological differentiation of human neuroblastoma. Thiele, C.J., Reynolds, C.P., Israel, M.A. Nature (1985) [Pubmed]
  17. Clinical applications of fish oils. Yetiv, J.Z. JAMA (1988) [Pubmed]
  18. Diet and cancer of the colon and rectum: a case-control study. Potter, J.D., McMichael, A.J. J. Natl. Cancer Inst. (1986) [Pubmed]
  19. Overview of current knowledge of metabolism of vitamin A and carotenoids. Goodman, D.S. J. Natl. Cancer Inst. (1984) [Pubmed]
  20. Reduced mortality among children in southern India receiving a small weekly dose of vitamin A. Rahmathullah, L., Underwood, B.A., Thulasiraj, R.D., Milton, R.C., Ramaswamy, K., Rahmathullah, R., Babu, G. N. Engl. J. Med. (1990) [Pubmed]
  21. Teratogenicity of high vitamin A intake. Rothman, K.J., Moore, L.L., Singer, M.R., Nguyen, U.S., Mannino, S., Milunsky, A. N. Engl. J. Med. (1995) [Pubmed]
  22. Embryonic retinoic acid synthesis is essential for early mouse post-implantation development. Niederreither, K., Subbarayan, V., Dollé, P., Chambon, P. Nat. Genet. (1999) [Pubmed]
  23. Regulation of terminal differentiation of cultured human keratinocytes by vitamin A. Fuchs, E., Green, H. Cell (1981) [Pubmed]
  24. Rpe65 is necessary for production of 11-cis-vitamin A in the retinal visual cycle. Redmond, T.M., Yu, S., Lee, E., Bok, D., Hamasaki, D., Chen, N., Goletz, P., Ma, J.X., Crouch, R.K., Pfeifer, K. Nat. Genet. (1998) [Pubmed]
  25. Plasminogen activator in chick fibroblasts: induction of synthesis by retinoic acid; synergism with viral transformation and phorbol ester. Wilson, E.L., Reich, E. Cell (1978) [Pubmed]
  26. Jun-Fos and receptors for vitamins A and D recognize a common response element in the human osteocalcin gene. Schüle, R., Umesono, K., Mangelsdorf, D.J., Bolado, J., Pike, J.W., Evans, R.M. Cell (1990) [Pubmed]
  27. A direct repeat in the cellular retinol-binding protein type II gene confers differential regulation by RXR and RAR. Mangelsdorf, D.J., Umesono, K., Kliewer, S.A., Borgmeyer, U., Ong, E.S., Evans, R.M. Cell (1991) [Pubmed]
  28. Membranes as the energy source in the endergonic transformation of vitamin A to 11-cis-retinol. Deigner, P.S., Law, W.C., Cañada, F.J., Rando, R.R. Science (1989) [Pubmed]
  29. Orphan nuclear receptors: shifting endocrinology into reverse. Kliewer, S.A., Lehmann, J.M., Willson, T.M. Science (1999) [Pubmed]
  30. The contribution of plant foods to the vitamin A supply of lactating women in Vietnam: a randomized controlled trial. Khan, N.C., West, C.E., de Pee, S., Bosch, D., Phuong, H.D., Hulshof, P.J., Khoi, H.H., Verhoef, H., Hautvast, J.G. Am. J. Clin. Nutr. (2007) [Pubmed]
  31. Genetic analysis of RXR alpha developmental function: convergence of RXR and RAR signaling pathways in heart and eye morphogenesis. Kastner, P., Grondona, J.M., Mark, M., Gansmuller, A., LeMeur, M., Decimo, D., Vonesch, J.L., Dollé, P., Chambon, P. Cell (1994) [Pubmed]
  32. Mutations in RPE65 cause autosomal recessive childhood-onset severe retinal dystrophy. Gu, S.M., Thompson, D.A., Srikumari, C.R., Lorenz, B., Finckh, U., Nicoletti, A., Murthy, K.R., Rathmann, M., Kumaramanickavel, G., Denton, M.J., Gal, A. Nat. Genet. (1997) [Pubmed]
  33. Immunity to Trichinella spiralis infection in vitamin A-deficient mice. Carman, J.A., Pond, L., Nashold, F., Wassom, D.L., Hayes, C.E. J. Exp. Med. (1992) [Pubmed]
  34. Dissection of the pathway required for generation of vitamin A and for Drosophila phototransduction. Wang, T., Jiao, Y., Montell, C. J. Cell Biol. (2007) [Pubmed]
  35. Activity of vitamin A analogues in cell cultures of mouse epidermis and organ cultures of hamster trachea. Sporn, M.B., Clamon, G.H., Dunlop, N.M., Newton, D.L., Smith, J.M., Saffiotti, U. Nature (1975) [Pubmed]
  36. Limbs generated at site of tail amputation in marbled balloon frog after vitamin A treatment. Mohanty-Hejmadi, P., Dutta, S.K., Mahapatra, P. Nature (1992) [Pubmed]
  37. Infectious disease surveillance during emergency relief to Bhutanese refugees in Nepal. Marfin, A.A., Moore, J., Collins, C., Biellik, R., Kattel, U., Toole, M.J., Moore, P.S. JAMA (1994) [Pubmed]
  38. Vitamin A supplementation and child mortality. A meta-analysis. Fawzi, W.W., Chalmers, T.C., Herrera, M.G., Mosteller, F. JAMA (1993) [Pubmed]
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