Clinics in Dermatology
Volume 27, Issue 2 , Pages 217-224 , March 2009

Ascorbigen: chemistry, occurrence, and biologic properties

  • Anika E. Wagner, PhD
    • ,
  • Gerald Rimbach, PhD

      Affiliations

    • Corresponding Author InformationCorresponding author. Institute of Human Nutrition and Food Science, Christian Albrechts University, Olshausenstrasse 40, D-24118 Kiel, Germany.

References 

  1. Benito E, Obrador A, Stiggelbout A, et al. A population-based case-control study of colorectal cancer in Majorca. I. Dietary factors. Int J Cancer. 1990;45:69–76
  2. Chyou PH, Nomura AM, Hankin JH, Stemmermann GN. A case-cohort study of diet and stomach cancer. Cancer Res. 1990;50:7501–7504
  3. Bradlow HL, Michnovicz J, Telang NT, Osborne MP. Effects of dietary indole-3-carbinol on estradiol metabolism and spontaneous mammary tumors in mice. Carcinogenesis. 1991;12:1571–1574
  4. Grubbs CJ, Steele VE, Casebolt T, et al. Chemoprevention of chemically-induced mammary carcinogenesis by indole-3-carbinol. Anticancer Res. 1995;15:709–716
  5. Bonnesen C, Eggleston IM, Hayes JD. Dietary indoles and isothiocyanates that are generated from cruciferous vegetables can both stimulate apoptosis and confer protection against DNA damage in human colon cell lines. Cancer Res. 2001;61:6120–6130
  6. Verhoeven DT, Verhagen H, Goldbohm RA, van den Brandt PA, van Poppel G. A review of mechanisms underlying anticarcinogenicity by Brassica vegetables. Chem Biol Interact. 1997;103:79–129
  7. Sorensen H. Glucosinolates: structure-properties-function. In:  Shahidi F editors. Canola and rapeseed production, chemistry, nutrition and processing technology. New York: Van R. Nostrand; 1990;p. 149–172
  8. Svirbely J, Szent-Györgyi A. The chemical nature of vitamin C. Biochem J. 1932;26:865–870
  9. Ahmad B. Observations on the chemical method for the estimation of Vitamin C. Biochem J. 1935;29:275–281
  10. McHenry EW, Graham M. Observations on the estimation of ascorbic acid by titration. Biochem J. 1935;29:2013–2019
  11. Pal JC, Guha BC. Combined ascorbic acid in plant food stuffs. J Indian Chem Soc. 1939;16:871–872
  12. Sen Gupta PN, Guha BC. Estimation of total vitamin C in food stuffs. J Indian Chem Soc. 1937;14:95–102
  13. Prochazka Z, Sanda V, Sorm F. Isolation of pure ascorbigen. Coll Czech Chem Commun. 1957;22:333–334
  14. Kiss G, Neukom H. Über die struktur des ascorbigens. Helv Chim Acta. 1966;49:989–992
  15. Feldheim W. Research on the determination of the antiscorbutic activity of ascorbigen. Int Z Vitaminforsch. 1961;31:297–303
  16. Feldheim W, Prochazka Z. On the antiscorbutic effectiveness of synthetic ascorbigen. Studies on ascorbigen metabolism in man and guinea pigs. Int Z Vitaminforsch. 1962;32:251–257
  17. Hrncirik K, Valusek J, Velisek J. A study on the formation and stability of ascorbigen in an aqueous system. Food Chem. 1998;63:349–355
  18. McDanell R, McLean AE, Hanley AB, Heaney RK, Fenwick GR. Differential induction of mixed-function oxidase (MFO) activity in rat liver and intestine by diets containing processed cabbage: correlation with cabbage levels of glucosinolates and glucosinolate hydrolysis products. Food Chem Toxicol. 1987;25:363–368
  19. Virtanen AI. Studies on organic sulphur compounds and other labile substances in plants. Phytochemistry. 1965;4:207–228
  20. Searle LM, Chamberlain K, Butcher DN. Preliminary studies on the effects of copper, iron, manganese ions on the degradation of 3-indolyl methyl-glucosinolate (a constituent of Brassica spp.) by myrosinase. J Sci Food Agric. 1984;35:745–748
  21. Bradfield CA, Bjeldanes LF. Structure-activity relationships of dietary indoles: a proposed mechanism of action as modifiers of xenobiotic metabolism. J Toxicol Environ Health. 1987;21:311–323
  22. Latxague L, Gardrat C, Coustille JL, Viaud MC, Rollin P. Identification of enzymatic degradation products from synthesized glucobrassicin by gas chromatography-mass spectrometry. J Chromatogr. 1991;586:166–170
  23. Gmelin R, Virtanen AI. Glucobrassicin, the precursor of the thiocyanate ion, 3-indolylacetonitrile, and ascorbigen in Brassica oleracea (and related) species. Ann Acad Sci Fenn, Ser A II Chem. 1961;107:1–25
  24. Kutacek M, Prochazka Z, Veres K. Biogenesis of glucobrassicin, the in vitro precursor of ascorbigen. Nature. 1962;194:393–394
  25. Bjeldanes LF, Kim JY, Grose KR, Bartholomew JC, Bradfield CA. Aromatic hydrocarbon responsiveness-receptor agonists generated from indole-3-carbinol in vitro and in vivo: comparisons with 2,3,7,8-tetrachlorodibenzo-p-dioxin. Proc Natl Acad Sci U S A. 1991;88:9543–9547
  26. De Kruif CA, Marsman JW, Venekamp JC, et al. Structure elucidation of acid reaction products of indole-3-carbinol: detection in vivo and enzyme induction in vitro. Chem Biol Interact. 1991;80:303–315
  27. Grose KR, Bjeldanes LF. Oligomerization of indole-3-carbinol in aqueous acid. Chem Res Toxicol. 1992;5:188–193
  28. Aleksandrova LG, Korolev AM, Preobrazhenskaya MN. Study of natural ascorbigen and related compounds by HPLC. Food Chem. 1992;45:61–69
  29. Preobrazhenskaya MN, Korolev AM, Lazhko EI, Aleksandrova LG, Bergman J, Lindström J-O. Ascorbigen as a precursor of 5,11-dihydroindolo 3,2-b]carbazole. Food Chem. 1993;48:57–62
  30. Preobrazhenskaya MN, Lazhko EI, Korolev AM. Reaction of (indol-3-yl)ethanediol with L-ascorbic acid. Tetrahedron Asymmetry. 1996;7:641–644
  31. Reznikova MI, Korolev AM, Bodyagin DA, Preobrazhenskaya MN. Transformations of ascorbigen in vivo into ascorbigen acid and 1-deoxy-1-(indol-3-yl)ketoses. Food Chem. 2000;71:469–474
  32. Hrncirik K, Valusek J, Velisek J. Investigation of ascorbigen as a breakdown product of glucobrassicin autolysis in Brassica vegetables. Eur Food Res Technol. 2001;212:576–581
  33. Ciska E, Pathak DR. Glucosinolate derivatives in stored fermented cabbage. J Agric Food Chem. 2004;52:7938–7943
  34. Sepkovic DW, Bradlow HL, Michnovicz J, Murtezani S, Levy I, Osborne MP. Catechol estrogen production in rat microsomes after treatment with indole-3-carbinol, ascorbigen, or beta-naphthoflavone: a comparison of stable isotope dilution gas chromatography-mass spectrometry and radiometric methods. Steroids. 1994;59:318–323
  35. Stephensen PU, Bonnesen C, Bjeldanes LF, Vang O. Modulation of cytochrome P4501A1 activity by ascorbigen in murine hepatoma cells. Biochem Pharmacol. 1999;58:1145–1153
  36. Gillner M, Bergman J, Cambillau C, Fernström B, Gustafsson J-A. Interactions of indoles with specific binding sites for 2,3,7,8-Tetrachlorodibenzo-p-dioxin in rat liver. Mol Pharmacol. 1985;28:357–363
  37. Kravchenko LV, Avren'eva LI, Guseva GV, Posdnyakov AL, Tutel'yan VA. Effect of nutritional indoles on activity of xenobiotic metabolism enzymes and T-2 toxicity in rats. Bull Exp Biol Med. 2001;131:544–547
  38. Preobrazhenskaya MN, Bukhman VM, Korolev AM, Efimov SA. Ascorbigen and other indole-derived compounds from Brassica vegetables and their analogs as anticarcinogenic and immunomodulating agents. Pharmacol Ther. 1993;60:301–313
  39. Musk SR, Preobrazhenskaya MN, Belitsky GA, et al. The clastogenic and mutagenic effects of ascorbigen and 1′-methylascorbigen. Mutat Res. 1994;323:69–74
  40. Farris PK. Topical vitamin C: a useful agent for treating photoaging and other dermatologic conditions. Dermatol Surg. 2005;31(7 Pt 2):814–818
  41. Dinkova-Kostova AT, Jenkins SN, Fahey JW, et al. Protection against UV-light-induced skin carcinogenesis in SKH-1 high-risk mice by sulforaphane-containing broccoli sprout extracts. Cancer Lett. 2006;240:243–252
  42. Lu YP, Lou YR, Xie JG, et al. Topical applications of caffeine or (-)-epigallocatechin gallate (EGCG) inhibit carcinogenesis and selectively increase apoptosis in UVB-induced skin tumors in mice. Proc Natl Acad Sci U S A. 2002;99:12455–12460
  43. Zhu M, Zhang Y, Cooper S, Sikorski E, Rohwer J, Bowden GT. Phase II enzyme inducer, sulforaphane, inhibits UVB-induced AP-1 activation in human keratinocytes by a novel mechanism. Mol Carcinog. 2004;41:179–186
  44. Enomoto A, Itoh K, Nagayoshi E, et al. High sensitivity of Nrf2 knockout mice to acetaminophen hepatotoxicity associated with decreased expression of ARE-regulated drug metabolizing enzymes and antioxidant genes. Toxicol Sci. 2001;59:169–177
  45. Xu C, Huang MT, Shen G, et al. Inhibition of 7,12-dimethylbenz(a)anthracene-induced skin tumorigenesis in C57BL/6 mice by sulforaphane is mediated by nuclear factor E2-related factor 2. Cancer Res. 2006;66:8293–8296
  46. Srivastava B, Shukla Y. Antitumour promoting activity of indole-3-carbinol in mouse skin carcinogenesis. Cancer Lett. 1998;134:91–95
  47. Cope RB, Loehr C, Dashwood R, Kerkvliet NI. Ultraviolet radiation-induced non-melanoma skin cancer in the Crl:SKH1:hr-BR hairless mouse: augmentation of tumor multiplicity by chlorophyllin and protection by indole-3-carbinol. Photochem Photobiol Sci. 2006;5:499–507
  48. Stephensen PU, Bonnesen C, Schaldach C, Andersen O, Bjeldanes LF, Vang O. N-methoxyindole-3-carbinol is a more efficient inducer of cytochrome P-450 1A1 in cultured cells than indol-3-carbinol. Nutr Cancer. 2000;36:112–121

PII: S0738-081X(08)00013-8

doi: 10.1016/j.clindermatol.2008.01.012

Clinics in Dermatology
Volume 27, Issue 2 , Pages 217-224 , March 2009

Article Tools

* Image Usage & Resolution