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Journal of Lipid Research, Vol 30, 719-730, Copyright © 1989 by Lipid Research, Inc.
DM Heuman
This paper describes the derivation of a bile salt monomeric hydrophobicity
index that quantitatively defines the composite hydrophilic-hydrophobic
balance of a mixture of bile salts. The index is based on the logarithms of
bile salt capacity factors determined using reversed phase high performance
liquid chromatography (HPLC) (stationary phase octadecyl silane; mobile
phase methanol-water 70:30 w/w, ionic strength 0.15). It has been
standardized arbitrarily to set indices of taurocholate and
taurolithocholate to 0 and 1, respectively. Indices of
tauroursodeoxycholate, taurohyodeoxycholate, taurochenodeoxycholate, and
taurodeoxycholate were found to be -0.47, - 0.35, +0.46, and +0.59,
respectively. Whereas capacity factors and hydrophobicity indices of
taurine-conjugated bile salts were constant for pH 2.8-9.0, the
hydrophilic-hydrophobic balance of glycine- conjugated and unconjugated
bile salts was strongly influenced by pH. At alkaline pH (greater than
8.5), hydrophobicity indices of fully ionized unconjugated (n = 4) and
glycine-conjugated (n = 6) bile salts differed by only 0.14 +/- 0.02 and
0.05 +/- 0.01, respectively, from those of the corresponding taurine
conjugates. At acid pH (less than 3.5) the hydrophobicity indices of four
unconjugated bile acids (protonated form) exceeded those of the
corresponding salts (ionized form) by 0.76 +/- 0.04; indices of six
glycine-conjugated bile acids exceeded those of the corresponding salts by
only 0.26 +/- 0.03. Capacity factors of the salt forms of cholate and its
conjugates increased dramatically with increasing ionic strength of the
mobile phase; retention of the protonated forms (cholic and glycocholic
acids) was only minimally influenced by ionic strength. Thus the difference
in hydrophilic-hydrophobic balance between a bile acid and its
corresponding salt decreases with increasing ionic strength. Examples are
given of calculation of hydrophobicity indices for biliary bile salts
(fully ionized) from four species under conditions of intact enterohepatic
circulation. Mean values, from least to most hydrophobic, were: rat (-0.31)
less than dog (0.11) less than hamster (0.22) less than human (0.32). This
study provides a rational basis for calculating the hydrophilic-hydrophobic
balance of mixed bile salt solutions over a broad range of pH.
ARTICLES
Quantitative estimation of the hydrophilic-hydrophobic balance of mixed bile salt solutions
Division of Gastroenterology, Medical College of Virginia, Richmond.
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