1-SIMILAR-TO-1 THE CHEMISTRY AND PHARMACOLOGY OF INDOLE-3-CARBINOL (INDOLE-3-METHANOL) AND 3-(METHOXYMETHYL)INDOLE - [PART I]

Indole-3-carbinol (I3C) (2) is produced endogenously from naturally oc curring glucosinolates contained in a wide variety of plant food subst ances including members of the family Cruciferae, and particularly mem bers of the genus Brassica, whenever they are crushed or cooked. The a cid environment of the gut very facilely converts it into a range of p olyaromatic indolic compounds, e.g. (3,4,5), which appear to be respon sible for many of the physiological effects observed following the ing estion of these foods. 3-(Methoxymethyl)indole (6) is formed with grea t ease whenever 2 contacts methylating agents, including methanol, and it is often found as a contaminant of 2, This contamination is often not recognized or easily removed because of the great similarities of the two in melting points and solubilities. However, their biological properties are essentially identical. These so-called chemopreventive compounds are important because of their enzyme induction and suppress ion, mutagenic, carcinogenic and, particularly, antimutagenic and anti carcinogenic properties. The natural occurrence, formation, preparatio n, identification, separation, quantification, chemical transformation s and general toxicological properties of these substances are critica lly reviewed in detail in this paper of 146 references, the first of t wo parts. The enzyme induction and suppression, mutagenic, antimutagen ic, mutagenic, anticarcinogenic and carcinogenic effects will be publi shed later as Part II. At the present time it appears that these have considerable potential as natural prophylactic anticancer agents again st certain common neoplasms, especially inasmuch modern diets are incr easingly deficient in these vegetable-derived substances.