Norcholic acid

A trihydroxycholestenoic acid was isolated as a major bile acid from bile of the toad, Bufo vulgaris formosus [70] and was characterized as (25/ )-3a,7a,12o(-trihy-droxy-5/8-cholest-23-en-26-oic acid by oxidation to 23-norcholic acid and hydrogenation to (25/ )-3a,7a,12a-trihydroxy-5j8-cholestan-26-oic acid [71]. The 5a isomer, 3a,7a,12a-trihydroxy-5a-cholest-23-en-26-oic acid, was recently detected as a minor bile acid in toad bile [46]. The bile of Varanus monitor contains as minor constituents 3a,7a,12a-trihydroxy-5j8-cholest-23- and 24-enoic acids [69]. The acid has been synthesized prior to its detection in nature [72]. 

This unsaturated coprostanic acid was isolated from toad bile by Haya-kawa (181). It was characterized by oxidation to norcholic acid and by... 

The enol lactone (12.7 g) is added to 157 ml of 0.5 M perbenzoic acid in benzene and allowed to stand at 25° for 140 hr. The solution is cooled to 15° and 15% sodium bisulfite solution is added to neutralize the excess peracid. The organic layer is separated and washed with saturated sodium bicarbonate solution and water. The benzene solution is dried over anhydrous sodium sulfate, filtered and concentrated to 30 ml. The product is crystallized by adding 80 ml of petroleum ether, filtered and washed with petroleum ether to yield 12.8 g (98%) of 3a,20,23-trihydroxy-16a-methyl-17(20)-oxido-ll-oxo-21-norchol-22-enoic acid-24(20)-lactone 3,23-diacetate mp 225-227°. 

Trihydroxy-21-diazopregnan-20-one 3,19-diacetate, 176 3 a,20,23 -Trihydroxy-16a-methyl-17(20)-oxido-11-0X0-2l-norchol-22-enoic acid 24(20)-lactone 3,23,diacetate, 191 3a,l l, 20 -Trihydroxy-5/3-C-norpregnane-l l -carboxylic acid, 438 3/3,11 a ,20/3-Trihydroxy-5o -pregnan-18-oic acid 18,20-lactone-3,l 1-diacetate, 252 3/3,5/S, 19-Trihydroxypregnan-20-one 3,19-diacetate, 176... 

CSH7NO 1953-54-4) see Oxitriptan (3P)-3-hydroxy-21-iodo-20,23-dioxo-21-norchol-5-en-24-oic acid etbyl ester... 

The bromohydrins, bromoketones, ketones, and alcohols derived from the 22,23-epoxides were also characterized.Stereochemical features of the reactions between the 24-norchol-22-ene system (84) and m-chloroperbenzoic acid, hypo-bromous acid, and osmium tetroxide have also been studied. 

Hydroxylation. Common to the reports of 3 papers [164,194,198] was identification of the urinary acid 3a,7a,12a,23-tetrahydroxy-5j8-cholanate, present as the taurine and glycine conjugates. Whether this is a precursor of norcholate (23-nor-3a,7 ,12a-trihydroxy-5/S-cholanate) remains to be determined. 

It was also demonstrated (Mandeau et al., 2005) that the ethanolic extract of the sponge Euryspongia contained petrosterol and was shown to display anti-inflammatory activity. This petrosterol on partitioning and further chromatography yielded compounds 3-hydroxy-24-norchol-5- -23-oic acid and 3p-hydroxy-26-norcampest-5-m-25-oic acid. The sterols were evaluated for their action on the metabolism of... 

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