1 - 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 occurring glucosinolates contained in a wide variety of plant food substances including members of the family Cruciferae, and particularly members of the genus Brassica, whenever they are crushed or cooked. The acid environment of the gut very facilely converts it into a range of polyaromatic indolic compounds, e.g. (3, 4,5), which appear to be responsible for many of the physiological effects observed following the ingestion of these foods. 3-(Methoxymethyl)indole (6) is formed with great 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 suppression, mutagenic, carcinogenic and, particularly, antimutagenic and anticarcinogenic properties. The natural occurrence, formation, preparation, identification, separation, quantification, chemical transformations and general toxicological properties of these substances are critically reviewed in detail in this paper of 146 references, the first of two parts. The enzyme induction and suppression, mutagenic, antimutagenic, mutagenic, anticarcinogenic and carcinogenic effects will be published later as Part II. At the present time it appears that these have considerable potential as natural prophylactic anticancer agents against certain common neoplasms, especially inasmuch modern diets are increasingly deficient in these vegetable-derived substances.
Food & Drug Administration, Center for Drug Evaluation and Research, ONDC, DNDC-1, Division of Neuropharmacological Drug Products (HFD-120), Woodmont II, 1451 Rockville Pike, Rockville MD 20852-1420, USA.
T A
TA
Broadbent
H S
HS
Broadbent
D016588:Anticarcinogenic Agents / Q000737:chemistry / Q000494:pharmacology; D016587:Antimutagenic Agents / Q000737:chemistry / Q000494:pharmacology; D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology*; D001937:Brassica / Q000737:chemistry; D019607:Brassicaceae / Q000737:chemistry; D003296:Cooking; D007211:Indoles / Q000737:chemistry* / Q000494:pharmacology*
C115454:3-(methoxymethyl)indole; D016588:Anticarcinogenic Agents; D016587:Antimutagenic Agents; D000975:Antioxidants; D007211:Indoles; C016517:indole-3-carbinol