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1H and 13C NMR characterization and stereochemical assignments of bile acids in aqueous media

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Lipids

Abstract

The unconjugated bile acids cholic acid, deoxycholic acid, and chenodeoxycholic acid; their glycine and taurine conjugated glycocholic acid, glycodeoxycholic acid, glycochenodeoxycholic acid, taurocholic acid, taurodeoxycholic acid, and taurochenodeoxycholic acid; and a taurine conjugated ursodeoxycholic acid, tauroursodeoxycholic acid, were characterized through 1H and 13C NMR in aqueous media under the physiological pH region (7.4±0.1). Assignments of 1H and 13C signals of all the bile acids were made using a combination of several one- and two-dimensional, homonuclear (1H−1H) and heteronuclear (1H−13C) correlations as well as spectral editing NMR methods. Stereochemical assignment of the five-membered ring of the bile acids is reported here for the first time. The complete characterization of various bile acids in aqueous media presented here may have implications in the study of the pathophysiology of biliary diseases through human biliary fluids using NMR spectroscopy.

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Abbreviations

CA:

cholic acid

CDCA:

chenodeoxycholic acid

DCA:

deoxycholic acid

DQF-COSY:

double-quantum filtered COSY

FID:

free induction decay

GCA:

glycocholic acid

GCDCA:

glycochenodeoxycholic acid

GDCA:

glycodeoxycholic acid

HMBC:

heteronuclear multiple-bond correlation

HSQC:

heteronuclear single-quantum correlation

nOe:

nuclear Overhauser enhancement

NOESY:

nuclear Overhauser enhancement spectroscopy

QCD:

quaternary carbon detection

SEFT:

spin-echo FT

TCA:

taurocholic acid

TCDCA:

taurochenodeoxycholic acid

TDCA:

taurodeoxycholic acid

TUDCA:

tauroursodeoxycholic acid

UDCA:

ursodeoxycholic acid

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Authors and Affiliations

  1. Centre of Biomedical Magnetic Resonance, Sanjay Gandhi Post-graduate Institute of Medical Sciences, 226 014, Raebareli Road, Lucknow, India

    Omkar B. Ijare, B. S. Somashekar, Y. Jadegoud & G. A. Nagana Gowda

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  1. Omkar B. Ijare
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  2. B. S. Somashekar
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  3. Y. Jadegoud
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  4. G. A. Nagana Gowda
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Correspondence to G. A. Nagana Gowda.

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Ijare, O.B., Somashekar, B.S., Jadegoud, Y. et al. 1H and 13C NMR characterization and stereochemical assignments of bile acids in aqueous media. Lipids 40, 1031–1041 (2005). https://doi.org/10.1007/s11745-005-1466-1

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  • DOI: https://doi.org/10.1007/s11745-005-1466-1

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