http://www.europa.com/~rsc/cancer/pip.txt Referrence 33, rcrs020197.txt From the Classic: Introduction to Physiological Chemistry by Meyer Bodansky, Ph.D., M.D. Director of Laboratories, John Sealy Hospital, Galveston, and Professor of Pathological Chemistry, University of Texas Third Edition John Wiley & Sons, Inc. London: CHAPMAN & HALL, LIMITED 1934. -------------------------------------------------------------------- [p.204, Par.1] Products of Intestinal Putrefaction[22] The contents of the large intestine undergo bacterial or putrefactive changes. Concerning bacterial action on fat, little can be said except that it results in the formation of fatty acids and glycerol. From lecithin may be formed choline, neurine, muscarine, and related compounds. CH3 CH2---CH2OH CH3 CH==CH2 CH3 CH2CHO \ / \ / \ / CH3-N CH3-N CH3-N / \ / \ / \ CH3 OH CH3 OH CH3 OH Choline Neurine Muscarine The carbohydrates yield a variety of substances, including oxalic acid, the lower fatty acids[23] and their derivatives--formic, acetic, propionic, lactic, butyric, oxybutyric, and succinic--acetone, and the gases carbon dioxide, methane, and hydrogen. If present in sufficient amount, some of the products of carbohydrate fermentation may act as irritants to the intestinal tract and cause diarrhea. Bacterial enzymes acting on protein yield proteoses, peptones, amino acids, ammonia, and hydrogen sulfide. From the aromatic amino acids are formed indole, skatole, phenol, cresol, and tyramine. Cadaverine, putrescine, and ethylidene-diamine are among the toxic amines, or ptomaines, formed from amino acids in putrefaction. Ethyl mercaptan(C2H5SH), methyl mercaptan (CH3SH), and hydrogen sulfide owe their origin to the putrefaction of cystine. With regard to the formation of these substances, much remains to be learned, but sufficient is known to enable us to consider briefly the chemistry of some of the reactions involved. Among the more important of these is one involving the removal of a carboxyl group (decarboxylation), presumably due to an enzyme, carboxylase, present in the bacteria. Another reaction consists in the splitting off of an amino group by deaminization. Reduction, due to a reductase, and reactions of hydrolysis as well as of oxidation are also believed to occur. Referrences 22. For a comprehensive survey of the subject, the student is referred to Marjory Stephenson's "Bacterial Metabolism," Longmans, Green & Co., London, 1930. 23. Grove, Olmstead and Koenig, J.Biol. Chem., 85, 127 (1929-30). ------------------------------------------------------------------------