Hyodeoxycholic acid

Soils have also been examined directly, not for evidence of possible contamination, but as a study of manuring practice in medieval to early modern Orkney, Scotland. The sterols campesterol, sitosterol, and 5/1-stigmastanol were used as biomarkers for ruminant animal manure and coprostanol for omnivorous animal manure, with hyodeoxycholic acid used to further define the manure as coming from pigs (Bull et al. 1999, Simpson et al. 1999). It is rare to be able to extract sterols from such samples because their natural abundance is generally low. If they can be found, however, then they are useful as unambiguous biomarkers for either plants or animals. 

Fig. 5.4.6 Mass chromatograms of pentafluorobenzyl bromide-trimethylsilylimidazole derivatives of BA standards (reprinted from [18]). 1 3j5-hydroxychol-5-enic acid, 2 LCA, 3 DCA, 4 CDCA, 5 hyodeoxycholic acid (HDCA), 6 ursodeoxycholic acid (UDCA), 7 [ll,12-d2] CDCA,...

Further study to examine the environment was done with biotin-appended dansyl-modified (3-CDs (42 and 43) [50], Biotin is well known to bind avidin (protein) tightly therefore, in this case, the environment is protein. The fluorescence intensities of 42 and 43 are more than three times larger in the presence of avidin. The lifetime measurements indicate that the longer-lifetime component, which newly appears in the presence of avidin, is likely to be the dansyl moiety located in the hydrophobic region of avidin. The addition of hyodeoxycholic acid in the presence of avidin decreased the fluorescence intensities of 42 and 43, but the degrees of the fluorescence variations induced by hyodeoxycholic acid are limited (AIII0 <0.16 for 42, AI/I0 <0.18 for 43) in comparison to the case in the absence of avidin (AI/I0 <0.29 for 42, AI/I0 <0.54 for 43). This may be due to the limited movement of the dansyl moiety in the presence of avidin. 

Ritter JK, Chen F, Sheen YY, et al. Two human liver cDNAs encode UDP-glucuronosyltransferases with 2 log differences in activity toward parallel substrates including hyodeoxycholic acid and certain estrogen derivatives. Biochemistry 1992 31(13) 3409-3414. 

Liu and Zhou applied Roush s crotylboration to the stereoselective synthesis of the orostanal 70, a novel sterol that induces apoptosis in human acute promyelotic leukemia cells28 (Scheme 3.ly). The aldehyde 72, prepared from hyodeoxycholic acid methyl ester, underwent asymmetric reaction with crotylboronate (R,R)-43E to furnish 73. Hydrogenation of the terminal alkene followed by Swem oxidation gave the ketone 74. Methylenation of the ketone and removal of the protective groups afforded orostanal in 50% yield. 

Tripodi et al. (1993) investigated the antic-holelithogenic and choleretic activities of tauro-hyodeoxycholic acid by measurement of biliary flow and biliary solids content in rats. 

There is a wide variety in the types of bile acids found in different animal species. Some species have unique bile acids, such as a-muricholic acid (3a,6p,7a-trihydroxy-5p-cholan-24-oic add) and -muridiolic add (3a,6, 7 -trihydroxy- -cholan 24-oic acid) in rats and mice, and hyodeoxycholic acid (3a,6a-dihydroxy-Sp-cholan>24-oic acid) in pigs. Haslewood (H9) has studied the distribution of bile acids in the animal kingdom and has suggested that the C-24 adds, which are common to most advanced animal forms, can be regarded as the present endpoints in the evolution of the chemical structure of bile adds. 

Internal standards which have been used for GLC of bile acids are numerous and include 7-ketoIithocholic acid (KIO, R12), hyodeoxycholic acid (K8),... 

Crystallise a-hyodeoxycholic acid from EtOAc or Mc2CO. The K salt separates in needles from an alcoholic solution of the acid when an equivalent of KOMe is added (see lithocholic acid). [Weiland Gumlish Hoppe Seyler s Z Physiol Chem 215 18 1933, Windaus Bohne Justus Liebigs Ann Chem 433 278 1923, Beilstein 10 III 1631.1... 

Abbreviations HDCA hyodeoxycholic acid C20ap 3a-hydroxyetianic acid C20pp 3p-hydroxyetianic acid LA lithocholic acid atRA all tran retinoic acid atRAc all tran retinyl acetate 13-HODE 13-hydroxy-9,lloctadecadienoic acid 13-Oxo-ODE 13-oxo-9, 11-octadeca-dienoic acid nd not determined. 

The synthesis of allomuricholic acids has been reported and is shown in Scheme Hyodeoxycholic acid (315) was selectively oxidized at C-6 and... 

FIGURE 3.4 Structures of endogenous compounds involved in glucuronidation bile adds, lithocholic add (LA) and hyodeoxycholic acid (HDCA) short chain bile acids, etianic add and isoetianic add, steroid hormones, androsterone, testosterone, estrone, estradiol, estriol. 

Bile acid Hyodeoxycholic acid 3a-OH-pregnanes and 3a, 16a, I7p-androgens... 

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