Document Detail

Structure elucidation of acid reaction products of indole-3-carbinol: detection in vivo and enzyme induction in vitro.
MedLine Citation:
PMID:  1954658     Owner:  NLM     Status:  MEDLINE    
The potency of indole-3-carbinol (I3C) to form condensation products under acidic aqueous conditions was studied. After identifying a known dimer, 3,3'-diindolylmethane (DIM), we elucidated the structures of two trimers also found in acid reaction mixtures: 5,6,11,12,17,18-hexahydrocyclonona[1,2-b:4,5-b':7,8-b"]tri-indole (CTI), and 2,3-bis[3-indolylmethyl] indole (BII). The formation of these indole oligomers was shown to be pH dependent. The highest amounts of DIM and BII were formed in aqueous solutions having a pH value ranging from 4 to 5. No CTI could be detected at pH values above 4.5. In rats that received an oral dose of I3C we could detect DIM and BII in gastric contents, stomach tissue, small intestine and liver. No CTI could be detected in vivo after oral exposure to I3C. In in vitro experiments, using rat hepatocytes, the cytochrome P-450IA1 apoprotein level, 7-ethoxyresorufin O-deethylation activity (EROD) and DT-diaphorase activity (DTD) were markedly enhanced by DIM and CTI as well as BII.
C A De Kruif; J W Marsman; J C Venekamp; H E Falke; J Noordhoek; B J Blaauboer; H M Wortelboer
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chemico-biological interactions     Volume:  80     ISSN:  0009-2797     ISO Abbreviation:  Chem. Biol. Interact.     Publication Date:  1991  
Date Detail:
Created Date:  1992-01-02     Completed Date:  1992-01-02     Revised Date:  2007-11-15    
Medline Journal Info:
Nlm Unique ID:  0227276     Medline TA:  Chem Biol Interact     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  303-15     Citation Subset:  IM    
UTOX, University of Utrecht, The Netherlands.
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MeSH Terms
Cells, Cultured
Chromatography, High Pressure Liquid
Cytochrome P-450 CYP1A1
Cytochrome P-450 Enzyme System / biosynthesis
Enzyme Induction / drug effects
Hydrogen-Ion Concentration
Indoles / chemistry*,  pharmacokinetics,  pharmacology
Liver / drug effects
Magnetic Resonance Spectroscopy
NAD(P)H Dehydrogenase (Quinone) / biosynthesis
Oxidoreductases / biosynthesis
Rats, Inbred Strains
Reg. No./Substance:
0/Indoles; 1968-05-4/3,3'-diindolylmethane; 700-06-1/indole-3-carbinol; 9035-51-2/Cytochrome P-450 Enzyme System; EC 1.-/Oxidoreductases; EC P-450 CYP1A1; EC Dehydrogenase (Quinone)

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