Ascorbigen and Other Indole-Derived Compounds From Brassica Vegetables and Their Analogs as Anticarcinogenic and Immunomodulating Agents

Pharmacol Ther. 1993 Nov;60(2):301-13. doi: 10.1016/0163-7258(93)90012-3.

Abstract

Searches for the natural compounds that determine the anticarcinogenic properties of a cruciferous-vegetable diet, revealed the products of alkaloid glucobrassicin biotransformations; among these, ascorbigen, an indole-containing derivative of L-ascorbic acid, was found to be the most abundant. Study of chemical properties of ascorbigen showed that it is capable of different transformations in acidic (including gastric juice) and slightly alkaline (including blood) media. The stable and unstable products of ascorbigen transformation determine the biological properties of the compound. The most important product of ascorbigen transformation in gastric juice is 5,11-dihydroindolo[3,2-b]-carbazole, with a binding affinity to the Ah receptor only 3.7 x 10(-2) lower than that of tetrachlorodibenzodioxin. This compound may be responsible for modifying P450 enzyme activities. Ascorbigen and its analogs are available synthetically. Their biological evaluation showed that some of the compounds of these series are immunomodulators. The most active is N-methylascorbigen, which demonstrates therapeutic effects (inhibition of tumor growth, protection of animals from bacterial and viral infections). The immunomodulatory activity of natural ascorbigen may be an additional factor of importance for the anticarcinogenic properties of a cruciferous-vegetable diet.

Publication types

  • Review

MeSH terms

  • Adjuvants, Immunologic / chemistry
  • Adjuvants, Immunologic / isolation & purification
  • Adjuvants, Immunologic / therapeutic use*
  • Animals
  • Anticarcinogenic Agents / chemistry
  • Anticarcinogenic Agents / isolation & purification
  • Anticarcinogenic Agents / therapeutic use*
  • Ascorbic Acid / analogs & derivatives*
  • Ascorbic Acid / chemistry
  • Ascorbic Acid / pharmacokinetics
  • Ascorbic Acid / therapeutic use
  • Biotransformation
  • Brassica* / chemistry
  • Brassica* / metabolism
  • Glucosinolates / chemistry
  • Glucosinolates / isolation & purification
  • Glucosinolates / pharmacokinetics
  • Humans
  • Hydrogen-Ion Concentration
  • Indoles / chemistry
  • Indoles / isolation & purification
  • Indoles / pharmacokinetics
  • Indoles / therapeutic use*
  • Molecular Sequence Data
  • Neoplasms, Experimental / drug therapy*

Substances

  • Adjuvants, Immunologic
  • Anticarcinogenic Agents
  • Glucosinolates
  • Indoles
  • ascorbigen
  • indole-3-carbinol
  • glucobrassicin
  • Ascorbic Acid