Nuclear magnetic resonance identification of the taurine conjugate of 3 alpha,6 beta,7 beta-trihydroxy-5 beta,22-cholen-24-oic acid (tauro-delta 22-beta-muricholate) in the serum of female rats treated with alpha-naphthylisothiocyanate.
Recently developed 1H nuclear magnetic resonance methods, including 2-dimensional, 1H-detected-[13C] shift correlation spectroscopy and 1-dimensional HOHAHA spectroscopy at 500 MHz have been used to identify the major bile acid in the serum of rats treated with alpha-naphthylisothiocyanate as the taurine conjugate of 3 alpha,6 beta,7 beta-trihydroxy-5 beta,22-cholen- 24-oic acid (tauro-delta 22-beta-muricholate), a derivative of beta-muricholate having an unsaturated bond in the acyclic side chain. Complete stereospecific assignments of the 1H and protonated 13C spectra of the title compound and beta-muricholate are reported. The assignments were based entirely on 1H-1H and 1H-13C scalar connectivities and were made using approximately 0.5-2.0 mg of material. It is suggested that these new methods will be of general value for identifying the structure and assigning the spectra of other scarce steroid-like molecules.
Davis
D G
DG
National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709.
Thompson
M B
MB
D015058:1-Naphthylisothiocyanate / Q000494:pharmacology; D000818:Animals; D002247:Carbon Isotopes; D005260:Female; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D011522:Protons; D051381:Rats; D011916:Rats, Inbred F344; D013656:Taurocholic Acid / Q000031:analogs & derivatives* / Q000097:blood
D002247:Carbon Isotopes; D011522:Protons; C037351:tauromuricholic acid; D015058:1-Naphthylisothiocyanate; D013656:Taurocholic Acid