The biosynthesis of ethyl esters of lithocholic acid and isolithocholic acid by rat intestinal microflora
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Lithocholic acid
Dietary lithocholic acid elevated plasma cholesterol and lipid phosphorus levels, and increased liver size of growing chicks. In cholesterol-fed chicks, lithocholic acid depressed liver lipid and cholesterol levels. The effects of lithocholic acid were partially reversed by cholic acid in chicks fed a cholesterol-free diet and almost completely reversed in chicks fed cholesterol. The plasma cholesterol level of cholesterol-fed chicks was increased by cholic acid feeding.
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Dietary lithocholic acid alone and in combination with cholic acid or cholesterol has been shown to induce the ductular cell reaction in the livers of chickens. Dietary cholic acid, deoxycholic acid, or cholesterol did not alter liver structure. Removal of lithocholic acid from the diet resulted in regression of the reaction.
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Dietary lithocholic acid increased plasma lipid levels, decreased liver fat, increased liver size and induced a marked biliary hyperplasia in chicks fed either a cholesterol-free or supplmented diet. Lithocholic acid increased liver cholesterol levels in chicks fed a cholesterol-free diet and decreased liver cholesterol in chicks fed a cholesterol-supplemented diet. Cholic acid supplementation partially prevented the changes in liver size and plasma liver lipid levels resulting from ingestion of a lithocholic acid-supplemented cholesterol-free diet. In cholesterol-fed chicks, cholic acid afforded almost complete protection against the effects of dietary lithocholic acid.
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As lithocholic acid has been found by many workers to exert a cirrhogenic effect on the liver in a variety of animal species, it seemed probable that, given simultaneously with butter-yellow, this biliary acid would act as a hepato-cocarcinogen. In an experimental investigation carried out in rats, both lithocholic and cholic acid showed no accelerating action on the carcinogenicity of butter-yellow. On the contrary, lithocholic acid alone, administered daily for several months, showed a slightly lower toxicity when compared with cholic acid.
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The population levels of intestinal microflora and bile acid composition in the digestive tract were examined in rats fed bile acids to determine the relationships between gastrointestinal microflora and the host. The population level of Bacteroides was increased in the ceca of rats fed cholic acid or deoxycholic acid. In the ileum, the concentration of conjugated bile acid in rats fed cholesterol, cholic acid, hyodeoxycholic acid or lithocholic acid was higher than that in control rats, and was very low in ceca and feces of all the rats. The concentration of total free bile acid was much higher in the ceca than in the ilea of rats fed hyodeoxycholic acid or lithocholic acid. Cholic acid and deoxycholic acid were found in the ilea, ceca and feces of the cholic acid-fed rats. In the deoxycholic acid-fed rats, cholic acid was localized in the ileum. 7-Ketodeoxycholic acid was also found in the ceca of the cholic acid-fed rats. 12-Ketolithocholic acid was found in the feces of rats fed cholic acid or deoxycholic acid. 3-Ketocholanic acid was found in some samples from the lithocholic acid-fed rats. Therefore, some kinds of bile acids influence the population levels of gastrointestinal microflora and bile acid composition in the intestine.
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The synthesis of macrocyclic derivatives of bile acids (cholaphanes) is elaborated using the formation of ester or amide linkages at the 3α,3′α- and 24,24′-positions of lithocholic, deoxycholic or cholic acids. The conditions were found under which the selective diacylation at the 3α,3′α- and 24,24′-positions of two molecules of cholic acid by dichloroanhydrides of arene(hetarene)dicarboxylic acid proceeds in good yields without prior protection of the 7α- and 12α-hydroxy groups.
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Lithocholic acid has been shown to counteract the hypercholesterolemic effect of cholic acid in the mouse and rat (Howe et al., 1960; Portman and Bruno, 1961). Recently, Edwards (1961) has presented data demonstrating a lack of effect of dietary cholic acid on serum cholesterol levels of growing chicks. In this report (Edwards, 1961), dietary lithocholic acid was shown to have a hypercholesterolemic effect in the chick in contrast to its cholesterol depressing action in the rat and mouse (Howe et al., 1960; Portman and Bruno, 1961). The influence of dietary bile acids on cholesterol and lipid metabolism is presently under investigation in this laboratory. During the course of these studies, dietary lithocholic acid was found to influence liver size markedly. Groups of six chicks were fed the experimental diets for 4 weeks (4 through 8 weeks of age). Prior to receiving the experimental diets, the chicks were fed a commercial …
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