Skip to main content
SpringerLink
Log in

Urocanic Acid and Skin Photodamage: New Light on an Old Chromophore

  • Chapter
  • First Online:
Skin Stress Response Pathways

Abstract

Urocanic acid (UCA) is one of the most efficient ultraviolet (UV) radiation-absorbing substances of the skin. UV irradiation leads to the interconversion of the two stereoisomers trans-UCA and cis-UCA, of which the latter is able to induce immunosuppression. Accordingly, the regulation of UCA biosynthesis, UV absorption by UCA in the cornified layer of the epidermis and the effects of UCA on the adaptive immune system are integral components of the cutaneous UV stress program. Here the evidence for the multiple roles of UCA in the skin and the associated open scientific questions are reviewed comprehensively.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 149.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 199.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 199.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  • Alm J, Holmgren G, Larsson A, Schimpfessel L (1981) Histidinaemia in Sweden: report on a neonatal screening programme. Clin Genet 20:229–233

    CAS  PubMed  Google Scholar 

  • Andersen FA (1995) Final report on the safety assessment of urocanic acid. J Am Coll Toxicol 14:386–423

    Article  Google Scholar 

  • Baden HP, Pathak MA (1967) The metabolism and function of urocanic acid in skin. J Invest Dermatol 48:11–17

    Article  CAS  PubMed  Google Scholar 

  • Baden HP, Hori Y, Pathak MA, Levy HL (1969a) Epidermis in histidinemia. Arch Dermatol 100:432–435

    Article  CAS  PubMed  Google Scholar 

  • Baden HP, Sviokla S, Maderson PF (1969b) A comparative study of histidase activity in amphibian, avian, reptilian and mammalian epidermis. Comp Biochem Physiol 30:889–894

    Article  CAS  PubMed  Google Scholar 

  • Barresi C, Stremnitzer C, Mlitz V, Kezic S, Kammeyer A, Ghannadan M, Posa-Markaryan K, Selden C, Tschachler E, Eckhart L (2011) Increased sensitivity of histidinemic mice to ultraviolet B radiation suggests a crucial role of endogenous urocanic acid in photoprotection. J Invest Dermatol 131:188–194

    Google Scholar 

  • Beissert S, Rühlemann D, Mohammad T, Grabbe S, El-Ghorr A, Norval M, Morrison H, Granstein RD, Schwarz T (2001) IL-12 prevents the inhibitory effects of cis-urocanic acid on tumor antigen presentation by Langerhans cells: implications for photocarcinogenesis. J Immunol 167:6232–6238

    Google Scholar 

  • Brand LM, Harper AE (1976) Histidine ammonia-lyase from rat liver. Purification, properties, and inhibition by substrate analogues. Biochemistry 15:1814–1821

    Article  CAS  PubMed  Google Scholar 

  • Brookman J, Chacón JN, Sinclair RS (2002) Some photophysical studies of cis- and trans-urocanic acid. Photochem Photobiol Sci 1:327–332

    Article  CAS  PubMed  Google Scholar 

  • Brusilow SW, Ikai K (1968) Urocanic acid in sweat: an artifact of elution from the epidermis. Science 160:1257–1258

    Article  CAS  PubMed  Google Scholar 

  • Bulfield G, Kacser H (1975) Histamine and histidine levels in the brain of the histidinaemic mutant mouse. J Neurochem 24:403–405

    Article  CAS  PubMed  Google Scholar 

  • Campos AM, Cárcamo C, Silva E, García S, Lemp E, Alarcón E, Edwards AM, Günther G, Lissi E (2008) Distribution of urocanic acid isomers between aqueous solutions and n-octanol, liposomes or bovine serum albumin. J Photochem Photobiol B 90:41–46

    Article  CAS  PubMed  Google Scholar 

  • Colburn NH, Lau S, Head R (1975) Decrease of epidermal histidase activity by tumor-promoting phorbol esters. Cancer Res 35:3154–3159

    CAS  PubMed  Google Scholar 

  • Cope RB, Fabacher DL, Lieske C, Miller CA (2001) Resistance of a lizard (the green anole, Anolis carolinensis; Polychridae) to ultraviolet radiation-induced immunosuppression. Photochem Photobiol 74:46–54

    Google Scholar 

  • De Fabo EC, Noonan FP (1983) Mechanism of immune suppression by ultraviolet irradiation in vivo. I. Evidence for the existence of a unique photoreceptor in skin and its role in photoimmunology. J Exp Med 158:84–98

    Article  PubMed  Google Scholar 

  • De Fabo E, Noonan F, Fisher M, Burns J, Kacser H (1983) Further evidence that the photoreceptor mediating UV-induced systemic immune suppression is urocanic acid. J Invest Dermatol 80:319 (Abstract)

    Google Scholar 

  • De Fabo EC, Webber LJ, Ulman EA, Broemeling LD (1997) Dietary L-histidine regulates murine skin levels of trans-urocanic acid, an immune-regulating photoreceptor, with an unanticipated modulation: potential relevance to skin cancer. J Nutr 127:2158–2164

    PubMed  Google Scholar 

  • de Fine Olivarius F, Wulf HC, Crosby J, Norval M (1996) The sunscreening effect of urocanic acid. Photodermatol Photoimmunol Photomed 12:95–99

    Article  Google Scholar 

  • de Fine Olivarius F, Wulf HC, Crosby J, Norval M (1998) Urocanic acid isomers and photosensitivity in healthy children. Br J Dermatol 139:605–609

    Article  PubMed  Google Scholar 

  • Denecker G, Hoste E, Gilbert B, Hochepied T, Ovaere P, Lippens S, Van den Broecke C, Van Damme P, D’Herde K, Hachem JP, Borgonie G, Presland RB, Schoonjans L, Libert C, Vandekerckhove J, Gevaert K, Vandenabeele P, Declercq W (2007) Caspase-14 protects against epidermal UVB photodamage and water loss. Nat Cell Biol 9:666–674

    Article  CAS  PubMed  Google Scholar 

  • Eckhart L, Schmidt M, Mildner M, Mlitz V, Abtin A, Ballaun C, Fischer H, Mrass P, Tschachler E (2008) Histidase expression in human epidermal: regulation by differentiation status and all-trans retinoic acid. J Dermatol Sci 50:209–215

    Article  CAS  PubMed  Google Scholar 

  • el-Ghorr AA, Norval M (1995) A monoclonal antibody to cis-urocanic acid prevents the ultraviolet-induced changes in Langerhans cells and delayed hypersensitivity responses in mice, although not preventing dendritic cell accumulation in lymph nodes draining the site of irradiation and contact hypersensitivity responses. J Invest Dermatol 105:264–268

    Article  CAS  PubMed  Google Scholar 

  • Espinós C, Pineda M, Martínez-Rubio D, Lupo V, Ormazabal A, Vilaseca MA, Spaapen LJ, Palau F, Artuch R (2009) Mutations in the urocanase gene UROC1 are associated with urocanic aciduria. J Med Genet 46:407–411

    Article  PubMed  Google Scholar 

  • Ferguson J, Johnson BE (1986) Photosensitivity due to retinoids: clinical and laboratory studies. Br J Dermatol 115:275–283

    Article  CAS  PubMed  Google Scholar 

  • Fluhr JW, Elias PM, Man MQ, Hupe M, Selden C, Sundberg JP, Tschachler E, Eckhart L, Mauro TM, Feingold KR (2010) Is the filaggrin-histidine-urocanic acid pathway essential for stratum corneum acidification? J Invest Dermatol 130:2141–2144

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Forbes D, Johnston L, Gardner J, MacCallum SF, Campbell LE, Dinkova-Kostova AT, McLean WH, Ibbotson SH, Dawe RS, Brown SJ (2016) Filaggrin genotype does not determine the skin’s threshold to UV-induced erythema. J Allergy Clin Immunol. doi:10.1016/j.jaci.2015.11.022

    Google Scholar 

  • Fujitaka M, Eguchi T, Sakura N, Ueda K (1993) Measurement of histidase activity in human fingernail by reversed-phase HPLC. Clin Chim Acta 215:227–232

    Article  CAS  PubMed  Google Scholar 

  • Gers-Balag H, Müller A, Sauermann G, Mann T (1997) The influence of sunscreens on the loss of urocanic acid during bathing. J Invest Dermatol 108:667 (Abstract)

    Google Scholar 

  • Gibbs NK, Tye J, Norval M (2008) Recent advances in urocanic acid photochemistry, photobiology and photoimmunology. Photochem Photobiol Sci 7:655–667

    Google Scholar 

  • Gill SC, von Hippel PH (1989) Calculation of protein extinction coefficients from amino acid sequence data. Anal Biochem 182:319–326

    Article  CAS  PubMed  Google Scholar 

  • Gilmour JW, Vestey JP, Norval M (1993) The effect of UV therapy on immune function in patients with psoriasis. Br J Dermatol 129:28–38

    Article  CAS  PubMed  Google Scholar 

  • Hanson KM, Simon JD (1998) Epidermal trans-urocanic acid and the UV-A-induced photoaging of the skin. Proc Natl Acad Sci USA 95:10576–10578

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Heenen M, Giacomoni PU, Golstein P (2001) Individual variations in the correlation between erythemal threshold, UV-induced DNA damage and sun-burn cell formation. J Photochem Photobiol B 63:84–87

    Article  CAS  PubMed  Google Scholar 

  • Hug DH, Dunkerson DD, Hunter JK (1999) The degradation of L-histidine and trans- and cis-urocanic acid by bacteria from skin and the role of bacterial cis-urocanic acid isomerase. J Photochem Photobiol B 50:66–73

    Article  CAS  PubMed  Google Scholar 

  • Hunter A (1912) On urocanic acid. J Biol Chem 11:537–545

    Google Scholar 

  • Ijland SA, Noonan FP, Ceryak S, Steenvoorden DP, Bouscarel B, Hug D, Beijersbergen van Henegouwen GM, De Fabo EC (1998) Urocanic acid does not photobind to DNA in mice irradiated with immunosuppressive doses of UVB. Photochem Photobiol 67:222–226

    Article  CAS  PubMed  Google Scholar 

  • Imamura I, Watanabe T, Hase Y, Sakamoto Y, Fukuda Y, Yamamoto H, Tsuruhara T, Wada H (1984) Histamine metabolism in patients with histidinemia: determination of urinary levels of histamine, N tau-methylhistamine, imidazole acetic acid, and its conjugate(s). J Biochem 96:1925–1929

    CAS  PubMed  Google Scholar 

  • Jaffe M (1874) Ueber einen neuen Bestandtheil des Hundeharns. Berichte der deutschen chemischen Gesellschaft 7:1669–1673

    Google Scholar 

  • Jauhonen HM, Kari E, Pylkkänen L, Poutanen J, Laihia J, Kaarniranta K, Leino L (2015) A randomized phase I clinical study of cis-urocanic acid eye drops in healthy adult subjects. Acta Ophthalmol 93:368–376

    Article  CAS  PubMed  Google Scholar 

  • Jones CD, Barton AK, Crosby J, Norval M, Gibbs NK (1996) Investigating the red shift between in vitro and in vivo urocanic acid photoisomerization action spectra. Photochem Photobiol 63:302–305

    Article  CAS  PubMed  Google Scholar 

  • Joo KM, Han JY, Son ED, Nam GW, Chung HY, Jeong HJ, Cho JC, Lim KM (2012) Rapid, simultaneous and nanomolar determination of pyroglutamic acid and cis-/trans-urocanic acid in human stratum corneum by hydrophilic interaction liquid chromatography (HILIC)-electrospray ionization tandem mass spectrometry. J Chromatogr B Analyst Technol Biomed Life Sci 897:55–63

    Article  CAS  Google Scholar 

  • Kacser H, Bulfield G, Wallace ME (1973) Histidinaemic mutant in the mouse. Nature 244:77–79

    Article  CAS  PubMed  Google Scholar 

  • Kammeyer A, Eggelte TA, Bos JD, Teunissen MBM (1999) Urocanic acid isomers are good hydroxyl radical scavengers: a comparative study with structural analogues and with uric acid. Biochim Biophys Acta 1428:117–120

    Article  CAS  PubMed  Google Scholar 

  • Kammeyer A, Eggelte TA, Overmars H, Bootsma A, Bos JD, Teunissen MBM (2001) Oxidative breakdown and conversion of urocanic acid isomers by hydroxyl radical generating systems. Biochim Biophys Acta 1526:277–285

    Article  CAS  PubMed  Google Scholar 

  • Kaneko K, Smetana-Just U, Matsui M, Young AR, John S, Norval M, Walker SL (2008) cis-Urocanic acid initiates gene transcription in primary human keratinocytes. J Immunol 181:217–224

    Article  CAS  PubMed  Google Scholar 

  • Kaneko K, Travers JB, Matsui MS, Young AR, Norval M, Walker SL (2009) cis-Urocanic acid stimulates primary human keratinocytes independently of serotonin or platelet-activating factor receptors. J Invest Dermatol 129:2567–2573

    Article  CAS  PubMed  Google Scholar 

  • Kaneko K, Walker SL, Lai-Cheong J, Matsui MS, Norval M, Young AR (2011) cis-Urocanic acid enhances prostaglandin E2 release and apoptotic cell death via reactive oxygen species in human keratinocytes. J Invest Dermatol 131:1262–1271

    Article  CAS  PubMed  Google Scholar 

  • Kawasaki H, Nagao K, Kubo A, Hata T, Shimizu A, Mizuno H, Yamada T, Amagai M (2012) Altered stratum corneum barrier and enhanced percutaneous immune responses in filaggrin-null mice. J Allergy Clin Immunol 129:1538–1546

    Article  CAS  PubMed  Google Scholar 

  • Kezic S, Kammeyer A, Calkoen F, Fluhr JW, Bos JD (2009) Natural moisturizing factor components in the stratum corneum as biomarkers of filaggrin genotype: evaluation of minimally invasive methods. Br J Dermatol 161:1098–1104

    Article  CAS  PubMed  Google Scholar 

  • Kim K (2012) Neuroimmunological mechanism of pruritus in atopic dermatitis focused on the role of serotonin. Biomol Ther (Seoul) 20:506–512

    Article  CAS  Google Scholar 

  • Kinuta M, Kinuta K, Yamada H, Abe T, Yoshida Y, Araki K, Li SA, Otsuka A, Nakanishi A, Moriyama Y, Takei K (2003) Formation of S-[2-carboxy-1-(1H-imidazol-4-yl) ethyl]glutathione, a new metabolite of L-histidine, from cis-urocanic acid and glutathione by the action of glutathione S-transferase. Electrophoresis 24:3212–3218

    Article  CAS  PubMed  Google Scholar 

  • Krien PM, Kermici M (2000) Evidence for the existence of a self-regulated enzymatic process within the human stratum corneum - an unexpected role for urocanic acid. J Invest Dermatol 115:414–420

    Article  CAS  Google Scholar 

  • Kripke ML, Cox PA, Alas LG, Yarosh DB (1992) Pyrimidine dimers in DNA initiate systemic immunosuppression in UV-irradiated mice. Proc Natl Acad Sci USA 89:7516–7520

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Kurogochi Y, Fukui Y, Nakagawa T, Yamamoto I (1957) A note on cis-urocanid acid. Jpn J Pharmacol 6:147–152

    Article  CAS  PubMed  Google Scholar 

  • Laihia JK, Taimen P, Kujari H, Leino L (2012) Topical cis-urocanic acid attenuates oedema and erythema in acute and subacute skin inflammation in the mouse. Br J Dermatol 167:506–513

    Article  CAS  PubMed  Google Scholar 

  • Langie SA, Knaapen AM, Houben JM, van Kempen FC, de Hoon JP, Gottschalk RW, Godschalk RW, van Schooten FJ (2007) The role of glutathione in the regulation of nucleotide excision repair during oxidative stress. Toxicol Lett 168:302–309

    Google Scholar 

  • Lam WK, Cleary MA, Wraith JE, Walter JH (1996) Histidinaemia: a benign metabolic disorder. Arch Dis Child 74:343–346

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Lee HJ, Park MK, Kim SY, Park Choo HY, Lee AY, Lee CH (2011) Serotonin induces melanogenesis via serotonin receptor 2A. Br J Dermatol 165:1344–1348

    Google Scholar 

  • Levy HL, Baden HP, Shih VE (1969) A simple indirect method of detecting the enzyme defect in histidinemia. J Pediat 75:1056–1058

    Article  CAS  PubMed  Google Scholar 

  • Ley RD, Reeve VE, Kusewitt DF (2000) Photobiology of Monodelphis domestica. Dev Comp Immunol 24:503–516

    Article  CAS  PubMed  Google Scholar 

  • Mehler AH, Tabor H (1953) Deamination of histidine to form urocanic acid in liver. J Biol Chem 201:775–784

    CAS  PubMed  Google Scholar 

  • Miajlovic H, Fallon PG, Irvine AD, Foster TJ (2010) Effect of filaggrin breakdown products on growth of and protein expression by Staphylococcus aureus. J Allergy Clin Immunol 126:1184–1190

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Mildner M, Jin J, Eckhart L, Kezic S, Gruber F, Barresi C, Stremnitzer C, Buchberger M, Mlitz V, Ballaun C, Sterniczky B, Födinger D, Tschachler E (2010) Knockdown of filaggrin impairs the diffusion barrier function and increases the UV sensitivity in a human skin model. J Invest Dermatol 130:2286–2294

    Article  CAS  PubMed  Google Scholar 

  • Mlitz V, Strasser B, Jaeger K, Hermann M, Ghannadan M, Buchberger M, Alibardi L, Tschachler E, Eckhart L (2014) Trichohyalin-like proteins have evolutionarily conserved roles in the morphogenesis of skin appendages. J Invest Dermatol 134:2685–2692

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Mohammad T, Morrison H, HogenEsch H (1999) Urocanic acid photochemistry and photobiology. Photochem Photobiol 69:115–135

    Google Scholar 

  • Moodycliffe AM, Norval M, Kimber I, Simpson TJ (1993) Characterization of a monoclonal antibody to cis-urocanic acid: detection of cis-urocanic acid in the serum of irradiated mice by immunoassay. Immunology 79:667–672

    CAS  PubMed  PubMed Central  Google Scholar 

  • Noonan FP, De Fabo EC (1992) Immunosuppression by ultraviolet B radiation: initiation by urocanic acid. Immunol Today 13:250–254

    Article  CAS  PubMed  Google Scholar 

  • Norval M (2006) The mechanisms and consequences of ultraviolet-induced immunosuppression. Prog Biophys Mol Biol 92:108–118

    Article  CAS  PubMed  Google Scholar 

  • Norval M, Gibbs NK, Gilmour J (1995) The role of urocanic acid in UV-induced immunosuppression: recent advances (1992–1994). Photochem Photobiol 62:209–217

    Google Scholar 

  • Palaszynski EW, Noonan FP, De Fabo EC (1992) cis-urocanic acid down-regulates the induction of adenosine 3′,5′-cyclic monophosphate by either trans-urocanic acid or histamine in human dermal fibroblasts in vitro. Photochem Photobiol 55:165–171

    Article  CAS  PubMed  Google Scholar 

  • Peltonen JM, Pylkkänen L, Jansén CT, Volanen I, Lehtinen T, Laihia JK, Leino L (2014) Three randomised phase I/IIa trials of 5% cis-urocanic acid emulsion cream in healthy adult subjects and in patients with atopic dermatitis. Acta Derm Venereol 94:415–420

    Article  CAS  PubMed  Google Scholar 

  • Reaven EP, Cox AJ (1965) Histidine and keratinization. J Invest Dermatol 45:422–431

    Article  CAS  PubMed  Google Scholar 

  • Reeve VE, Greenoak GE, Canfield PJ, Boehm-Wilcox C, Gallagher CH (1989) Topical urocanic acid enhances UV-induced tumour yield and malignancy in the hairless mouse. Photochem Photobiol 49:459–464

    Article  CAS  PubMed  Google Scholar 

  • Reilly JT, Troester KA, Tyner TT, Vitale DA, Risher TR (2010) Inhibition of histidine ammonia lyase by 8-methoxypsoralen and psoralen-oxidized photoproducts. Photochem Photobiol 86:1272–1277

    Google Scholar 

  • Safer D, Brenes M, Dunipace S, Schad G (2007) Urocanic acid is a major chemoattractant for the skin-penetrating parasitic nematode Strongyloides stercoralis. Proc Natl Acad Sci USA 104:1627–1630

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Sastry CM, Whitmore SE, Breysse PN, Morison WL, Strickland PT (2005) The effect of clinical UVA/B exposures on urinary urocanic acid isomer levels in individuals with caucasian type (II/III) skin types. Dermatol Online J 11:1

    PubMed  Google Scholar 

  • Schwarz T, Schwarz A (2011) Molecular mechanisms of ultraviolet radiation-induced immunosuppression. Eur J Cell Biol 90:560–564

    Article  CAS  PubMed  Google Scholar 

  • Schwarz A, Stander S, Berneburg M, Bohm M, Kulms D, van Steeg H, Grosse-Heitmeyer K, Krutmann J, Schwarz T (2002) Interleukin-12 suppresses ultraviolet radiation-induced apoptosis by inducing DNA repair. Nat Cell Biol 4:26–31

    Article  CAS  PubMed  Google Scholar 

  • Schwarz A, Eckhart L, Tschachler E, Schwarz T (2012) The function of Langerhans cells is intrinsically regulated by urocanic acid. J Invest Dermatol 132 (Suppl 2):S118–S123 (Abstract)

    Google Scholar 

  • Schwede TF, Rétey J, Schulz GE (1999) Crystal structure of histidine ammonia-lyase revealing a novel polypeptide modification as the catalytic electrophile. Biochemistry 38:5355–5361

    Article  CAS  PubMed  Google Scholar 

  • Scott IR (1981) Factors controlling the expressed activity of histidine ammonia-lyase in the epidermis and the resulting accumulation of urocanic acid. Biochem J 194:829–838

    Article  CAS  PubMed  Google Scholar 

  • Scott IR, Harding CR, Barrett JG (1982) Histidine-rich protein of the keratohyalin granules. Source of the free amino acids, urocanic acid and pyrrolidone carboxylic acid in the stratum corneum. Biochim Biophys Acta 719:110–117

    Article  CAS  PubMed  Google Scholar 

  • Shen L, Ji HF (2008) Theoretical investigation of the photosensitization mechanisms of urocanic acid. J Photochem Photobiol B 91:96–98

    Google Scholar 

  • Shimizu K, Andoh T, Yoshihisa Y, Shimizu T (2015) Histamine released from epidermal keratinocytes plays a role in α-melanocyte-stimulating hormone-induced itching in mice. Am J Pathol 185:3003–3010

    Article  CAS  PubMed  Google Scholar 

  • Sreevidya CS, Fukunaga A, Khaskhely NM, Masaki T, Ono R, Nishigori C, Ullrich SE (2010) Agents that reverse UV-induced immune suppression and photocarcinogenesis affect DNA repair. J Invest Dermatol 130:1428–1437

    Article  CAS  PubMed  Google Scholar 

  • Suchi M, Sano H, Mizuno H, Wada Y (1995) Molecular cloning and structural characterization of the human histidase gene (HAL). Genomics 29:98–104

    Article  CAS  PubMed  Google Scholar 

  • Tabachnik J (1957) Urocanic acid, the major acid soluble UV absorbing compound in guinea pig epidermis. Arch Biochem Biophys 70:295–297

    Article  Google Scholar 

  • Tanabe M, Sakura N (1989) Hyperhistaminemia in patients with histidinemia due to increased decarboxylation of histidine. Clin Chim Acta 186:11–17

    Article  CAS  PubMed  Google Scholar 

  • Taylor RG, Lambert MA, Sexsmith E, Sadler SJ, Ray PN, Mahuran DJ, McInnes RR (1990) Cloning and expression of rat histidase. Homology to two bacterial histidases and four phenylalanine ammonia-lyases. J Biol Chem 265:18192–18199

    CAS  PubMed  Google Scholar 

  • Taylor RG, Grieco D, Clarke GA, McInnes RR, Taylor BA (1993) Identification of the mutation in murine histidinemia (his) and genetic mapping of the murine histidase locus (Hal) on chromosome 10. Genomics 16:231–240

    Article  CAS  PubMed  Google Scholar 

  • Thyssen JP, Thuesen B, Huth C, Standl M, Carson CG, Heinrich J, Krämer U, Kratzsch J, Berg ND, Menné T, Johansen JD, Carlsen BC, Schwab S, Thorand B, Munk M, Wallaschofski H, Heickendorff L, Meldgaard M, Szecsi PB, Stender S, Bønnelykke K, Weidinger S, Bisgaard H, Linneberg A (2012) Skin barrier abnormality caused by filaggrin (FLG) mutations is associated with increased serum 25-hydroxyvitamin D concentrations. J Allergy Clin Immunol 130:1204–1207

    Article  CAS  PubMed  Google Scholar 

  • Thyssen JP, Bikle DD, Elias PM (2014) Evidence that loss-of-function filaggrin gene mutations evolved in northern Europeans to favor intracutaneous vitamin D3 production. Evol Biol 41:388–396

    Article  PubMed  PubMed Central  Google Scholar 

  • Torres N, Martinez L, Aleman G, Bourges H, Tovar AR (1998) Histidase expression is regulated by dietary protein at the pretranslational level in rat liver. J Nutr 128:818–824

    CAS  PubMed  Google Scholar 

  • Tye J, Walter JH, Griffiths CEM, Gibbs NK (2008) A lack of epidermal urocanic acid in histidinaemic skin influences ultraviolet B-induced CD1a+ Langerhans cell trafficking. Br J Dermatol 158:885 (Abstract)

    Google Scholar 

  • Ullrich SE (2005) Mechanisms underlying UV-induced immune suppression. Mutat Res 571:185–205

    Article  CAS  PubMed  Google Scholar 

  • Walterscheid JP, Nghiem DX, Kazimi N, Nutt LK, McConkey DJ, Norval M, Ullrich SE (2006) Cis-urocanic acid, a sunlight-induced immunosuppressive factor, activates immune suppression via the 5-HT2A receptor. Proc Natl Acad Sci USA 103:17420–17425

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Widhalm K, Virmani K (1994) Long-term follow-up of 58 patients with histidinemia treated with a histidine-restricted diet: no effect of therapy. Pediatrics 94:861–866

    CAS  PubMed  Google Scholar 

  • Wondrak GT, Jacobson MK, Jacobson EL (2006) Endogenous UVA-photosensitizers: mediators of skin photodamage and novel targets for skin photoprotection. Photochem Photobiol Sci 5:215–237

    Article  CAS  PubMed  Google Scholar 

  • Woodward EA, Prele CM, Finlay-Jones JJ, Hart PH (2006) The receptor for cis-urocanic acid remains elusive. J Invest Dermatol 126:1191–1193

    Article  CAS  PubMed  Google Scholar 

  • Wright AF, Bulfield G, Arfin SM, Kacser H (1982) Comparison of the properties of histidine ammonia-lyase in normal and histidinemic mutant mice. Biochem Genet 20:245–263

    Article  CAS  PubMed  Google Scholar 

  • Yarosh DB, Gettings SD, Alas LG, Kibitel JT, San RH, Wagner VO 3rd, McEwen GN Jr (1992) The biological interaction of cis and trans-urocanic acid with DNA. Photodermatol Photoimmunol Photomed 9:121–126

    CAS  PubMed  Google Scholar 

  • Yokoya S, Tokuhiro E, Suwa S, Maesaka H (1983) Measurement of the skin urocanic acid content in normal and histidinemic infants. Eur J Pediatr 140:330–332

    Article  CAS  PubMed  Google Scholar 

  • Yu B, Li AH, Muzny D, Veeraraghavan N, de Vries PS, Bis JC, Musani SK, Alexander D, Morrison AC, Franco OH, Uitterlinden A, Hofman A, Dehghan A, Wilson JG, Psaty BM, Gibbs R, Wei P, Boerwinkle E (2015) Association of rare loss-of-function alleles in HAL, serum histidine: Levels and incident coronary heart disease. Circ Cardiovasc Genet 8:351–355

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Zannoni VG, La Du BN (1963) Determination of histidine alpha-deaminase in human stratum corneum and its absence in histidinaemia. Biochem J 88:160–162

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Zenisek A, Kral JA (1953) The occurrence of urocanic acid in human sweat. Biochim Biophys Acta 12:479–480

    Article  CAS  PubMed  Google Scholar 

  • Zenisek A, Kral JA, Hais IM (1955) Sun-screening effect of urocanic acid. Biochim Biophys Acta 18:589–591

    Article  CAS  PubMed  Google Scholar 

  • Zhang Y, Wang W, Chen J, Zhang K, Gao F, Gao B, Zhang S, Dong M, Besenbacher F, Gong W, Zhang M, Sun F, Feng W (2013) Structural insights into the intrinsic self-assembly of Par-3 N-terminal domain. Structure 21:997–1006

    Article  CAS  PubMed  Google Scholar 

  • Zhang XX, Ritchie SR, Rainey PB (2014) Urocanate as a potential signaling molecule for bacterial recognition of eukaryotic hosts. Cell Mol Life Sci 71:541–547

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Research Division of Biology and Pathobiology of the Skin, Department of Dermatology, Medical University of Vienna, Lazarettgasse 14, 1090, Vienna, Austria

    Leopold Eckhart

Authors
  1. Leopold Eckhart
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Leopold Eckhart .

Editor information

Editors and Affiliations

  1. Department of Pharmacology and Toxicology, College of Pharmacy & The University of Arizona Cancer Center, Department of Pharmacology and Toxicology, TUCSON, Arizona, USA

    Georg T. Wondrak

Rights and permissions

Reprints and permissions

Copyright information

© 2016 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Eckhart, L. (2016). Urocanic Acid and Skin Photodamage: New Light on an Old Chromophore. In: Wondrak, G. (eds) Skin Stress Response Pathways. Springer, Cham. https://doi.org/10.1007/978-3-319-43157-4_4

Download citation

Publish with us

Policies and ethics

Search

Navigation