Formation and conversion of indoles in mammal gastrointestinal tract (IMAGE)
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LTr1 and DIM form as antitumor agents in mouse gastrointestinal tract from cruciferous vegetable-derived indole-3-carbinol (I3C). In the upper gastrointestinal tract, LTr1 generates through the Michael addition of 3-methyleneindolium (3MI, derived in situ from I3C) to DIM that is produced from I3C via the formaldehyde-releasing (major) and CO2-liberating (minor) pathways. The indole-recruiting pathway occurs primarily in large intestine where I3C and DIM formed from couplings of formaldehyde with one and two indole molecules, respectively. I3C, indole-3-carbinol; I3A, indole-3-carbaldehyde; I3CA, indole-3-carboxylic acid; DIM, 3,3'-diindolylmethane; LTr1, 2-(indol-3-ylmethyl)-3,3'-diindolylmethane; 3MI, 3-methyleneindolium; IS-1 and IS-2, intermediate salts 1 and 2, respectively; WMR, Wagner-Meerwein rearrangement.
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