New comprehensive biochemistry vol 12 sterols and bile acids

STEROLS AND BILE ACIDS New Comprehensive Biochemistry Volume 12 General Editors A NEUBERGER London L.L.M van DEENEN Urrecht ELSEVIER AMSTERDAM NEW YORK OXFORD * * Sterols and Bile Acids Editors HENRY DANIELSSON a and JAN SJOVALL Department of Pharmaceutical Biochemistiy, University of Uppsala, Uppsala (Sweden) and Department of Physiological Chemistiy, Karolinska Institutet, Stockholm (Sweden) a 1985 ELSEVIER Amsterdam - New York Oxford * 1985 Elsecier Science Publishers B.V (Biomedical Division) All nghts reserved No part of ths publication may be reproduced stored in a retrieval system or transmtted in any form or by any means, electronic, mechanical, photocopying, recording or otherwise without the prior writren permission of the publisher Elsevier Science Publishers B.V (Biomedical Division) P.O Box 1527, lo00 BM Amsterdam (The Netherlands) Special regulation for readers in the U.S.A.: This publication has been registered with the Copyright Clearance Center Inc (CCC), Salem, Massachusetts Information can be obtained from the CCC about conditions under which the photocopying of parts of this publication may be made in the U.S.A All other copyright questions, including photocopying outside of the U.S.A., should be referred to the publisher ISBN for the series: 0-444-80303-3 ISBN for the volume: 0-444-80670-9 Published by : Fl\evier Science Publishers B.V (Biomedical Division) P.0 Box 211 loo0 AE Amsterdam (The Netherlands) Sole distributors for the U.S.A dnd Canada Elsevier Science Publishing Company Inc 52 Vanderbilt Avenue Ye* York K Y 10017 (USA) Library of Congress Cataloging-in-Publication Data Main entry under title Sterols and bile acids (New comprehensive biochemistry: v 12) Includes bibliographies and index Sterols 1Metabolism.2 Bile acids-Metabolism I Danielsson Henry 11 Sjovall Jan 111 Series [DNLM: Bile Acids and Salts metabolism Sterols metabolism W1 NE372F v.12 / QU 95 S8391 QD415.N48 VOI.12 574.19’2 s 1574.19’2431185-20620 /QB752.S75] ISBN 0-444-80670-9 (U.S.) Printed in The Netherlands Preface Sterols are essential components of all eukaryotic cells Their function is structural, and by being precursors of hormones and bile acids they exert a regulatory function on metabolic processes Cholesterol and its metabolism are of importance in human disease Although the mechanisms are largely unknown, it can be surmised that abnormalities in the metabolism of sterols and bile acids are associated with cardiovascular disease and gallstone formation Steroid hormones are vital for man, animals and plants Disturbances in their production can have deleterious consequences T h s volume of New Comprehensive Biochemistry is entitled Sterols and Bile Acids It includes fourteen chapters written by prominent scientists in the field The large volume of material in the field of sterols and bile acids has necessitated a limitation of the areas covered Chapters on steroid hormones have been excluded since this field requires a volume of its own In spite of this it has not been possible to produce a book of some few hundred pages Efforts have been made to condense the contributions of the individual authors, but the wealth of important information is such that a further reduction in size would seriously affect the value of the chapters to the reader It may be argued that there are important gaps in the contents of this volume For instance, full discussions of the role of compartmentation of sterols and their metabolism, of the dynamics of cholesterol balance, etc are lacking We as editors take full responsibility for ths Our only excuse is that the material contained in the volume is already at the limit of what can be accommodated in a volume of New Comprehensive Biochemistry Although we have tried to make terminology, abbreviations, etc reasonably uniform it will be apparent that there are differences between chapters, but hopefully not within a chapter We have felt it more important to let the individualities of the authors be expressed It is our conviction that the eminent contributions in this volume, for which we are very grateful to our colleagues, will be of the value they deserve for all scientists in the field of sterol and bile acid research Uppsala and Stockholm September 1985 Henry Danielsson Jan Sjovall This Page Intentionally Left Blank H Danielsson and J Sjovall (Eds.), Sterols and Bile Acids 1985 Elsevier Science Publishers B.V (Biomedical Division) Contents v Chapter I Biosynthesis of cholesterol Hans C filling and Liliane T Chayet (Salt Lake City and Santiago) - Preface 11 I 11 111 Acetyl-CoA acetyl transferase (EC 2.3.1.9) Cellular location Enzymology IV Enzymology V Mechanism VI VII Phosphomevalonate kinase (EC 2.7.4.2) VIII IX Enzymology 12 13 14 21 X Mechanism Termination XI Squalene synthetase 20 24 XII Enzymology Mechanism 28 XIII The conversion of lanosterol to cholesterol Sterol function General aspects of enzymology The pathway Decarbonylation at (2-14 Decarboxylation at C-4 Introduction of As , Acknowledgement References Chapter Control mechanisms in steroi uptake and biosynthesis John F Gill Jr., Peter J Kennelly and Victor W Rodwell (West tafayette) 11 Control of sterol uptake Plasma lipoproteins , , , , , a Normal plasma lipoproteins, 41 - b Abnormal plasma lipoproteins, Chemically modified lipoproteins, 44 Cellular mechanisms of cholesterol uptake a The LDL receptor and receptor-mediated endocytosis, 45 - b Other receptor-mediated lipoprotein uptake mechanisms, 48 - c Receptor ndent cholesterol uptake, 51 Regulation of receptor-mediated sterol uptake _ ._ Diseases related to receptor-mediated cholesterol upta a Homozygous FH, receptor-negative and receptor-defective, 54 - b Heterozygous FH 56 - c Homozygous FH internalization-defective, 56 - d Wolman syndrome, 56 - e Cholesterol ester storage disease, 56 Control of sterol biosynthesis Mammalian HMG-CoA reductase a Rate-limiting step in sterol bi b Distribution, 57 - c Diurnal rhythm and developmental pattern, 58 - d Regulation of HMG-CoA reductase protein level 59 - e Modulation of HMG-CoA reductase activity, 62 Other sites of control a Early sites of control 65 - b Later sites of control, 66 ~ 31 31 31 32 32 34 36 37 37 41 41 41 44 52 _54 57 57 65 67 61 Chapier Participution of sterol carrier proteins in cholesterol biosynthesis, utilization and intracellulur transfer Terence J Scallen and George V Vahouny (Albuquerque and Washington) I 11 Introduction Sterol carrier protein, (SCP,) Purification and characteri Substratespecificity Participation of SCP, in squalene to sterol Properties of SCP, , 73 13 74 74 74 75 75 ix 111 IV Sterol carrier protein, (SCP,) Participation of SCP, in cholesterolbiosynthesis a General remarks, 77 - b Purification and characterization of SCP,, 77 - c Substrate specificity,78 - d Kinetic studies, 78 - e Anti-SCP, IgG, 792 Participation of SCP, in cholesterolutilization a Cholesterol esterification, 80 - b Cholesterol 7a-hydroxylase,81 Participation of SCP, in intracellular cholesterol transfer a SCP, is required for cholesterol transport from adrenal lipid droplets to mitochondria, 82 - b Identification of adrenal SCP,, 84 - c SCP, facilitates the translocation of cholesterol from the outer to the inner mitochondrial membrane, 85 Comparisoqof SCP, with other low molecular weight proteins a Fatty-acid-binding protein (FABP), 87 - b Nonspecific phospholipid exchange protein, 90 The participation of sterol carrier proteins in intracellular cholesterol metabolism 77 77 Acknowledgements References 91 91 Chapter Biosynthesis, function and metabolism of sterol esters Alan Jones and John Glomset (Seattle) Introduction I 11 Distribution and physical properties of cholesterolesters 111 Enzymes and proteins that mediate the formation, transp esters Acyl-CoA :cholesterol acyltransferase(EC 2.3.1.26) Cholesterol ester hydrolase (EC 3.1.1.13) a Acid CEH, 101 - b Neutral CEH, 102 Lecithin :cholesterolacyltransferase(EC 2.3.1.43) Plasma cholesterolester transfer protein IV Physiology of choles Plasma lipoprotein cholesterol esters Tissue cholesterolesters a Fibroblasts, 111 - b Cells that form steroid hormones, 112 - c Macrophages, 112 - d Hepatocytes, 113 Cholesterol sulfate V VI Cholesterol esters and disease , VII Conclusion References 80 82 87 91 95 95 95 98 98 101 103 106 107 107 110 113 114 116 116 Chapter Cholesterol absorption and metabolism by the intestinal epithelium Eduard F Stange and John M Dietschy (Dallas) 121 I 11 111 Introduction Absorption of cholesterol Intestinal cholesterolsynthesis Methodology Localization 121 123 125 125 126 434 Dealkylation of phytosterols, insects, in, 213 marine invertebrates, in, 211 mechanism of, 214-216 Decarbonylation, cholesterol biosynthesis, in, 32 Decarboxylation, cholesterol biosynthesis, in, 34 Deconjugation, conjugated bile acids, of, 333 24(28)-Dehydroaplysterol Occurrence of, 201 structure of, 201 7-Dehydrocholesterol ecdysteroids, biosynthesis of and, 220 membranes, in, 152 22-Dehydr~clerosterol, poriferasterol, formation of, from, 180, 188 structure of, 180 24-Dehydro-26-deoxy-Sa-ranol Occurrence of, 280, 285 structure of, 285 24-Dehydro-26-deoxy-5P-ranol, Occurrence of 280, 285 structure of, 285 7a-Dehydroxylase, C bifermentas in, 339 Eubacterium sp V.P.I 12708, in, 339 induction of 339 mechanism of, 338 microbial bile acid metabolism, in, 338 properties of, 339 stimulation of, 339 7P-DehydroxyIase, microbial bile acid metabolism, in, 339 Demethylation, mechanisms of, 32-35, 184-186 24-methylene lophenol, formation of, by, 185 31-norcycloartenol, formation of, by, 185 obtusifoliol, of, 186 poriferasterol, formation of, by, 186 23-Demethylgorgosterol, Occurrence of, 205 structure of, 205 Democolcine, mevalonate kinase, effect on, of, 65 Density, bile acids and salts of, 351 bile acid micelles, of, 351 Deoxycholic acid, allodeoxycholic acid, formation of, from, 321 12a-hydroxy-5P-cholanoic acid, formation from, of, 311 6j?-hydroxylation of 312 7a-hydroxylation of, 313 16n-hydroxylation of, 315 1~,3a,12a-trihydroxy-5~-cholanoic acid, formation of, from, 321 Deoxycorticosterone, plants, in, 190 27-Deoxy-5a-cyprinol, metabolism of, 297 Occurrence of, 280 284 structure of, 284 2-Deoxyecdysone, biosynthesis of, 222 Occurrence of, 221 structure of, 221 16-Deoxymyxinol, Occurrence of, 280, 284 structure of, 284 26-Deoxyranol, Occurrence of, 280, 284 structure of, 284 26-Deoxy-Sfi-ranoI biosynthesis of, 298 cholic acid biosynthesis, and, 295 a-Dermophol, Occurrence of, 280, 281 structure of, 282 5P-Dermophol, Occurrence of, 280, 281 structure of, 282 Desa turation, cholesterol biosynthesis, in, 36 Desmosterol, membranes, in, 152 Desulfation sulfated bile acids, of, 334 Diabetes, HMG-CoA reductase, effect on, of, 60 Dichloroacetate, HMG-CoA reductase effect on, of, 60 Dietary lipids, composition of, 121 digestion of, 121 Diffusion barriers, intestinal mucosa, of 123-125 410 435 a,6P-Dihydroxy-5P-cholanoicacid, 7P-hydroxylation of, 313 lithocholic acid, formation from, of, 311 3P,6 a-Dihydroxy-5/3-cholanoicacid, occurrence of, 313 3P,7a-Dihydroxy-5-cholenoicacid, chenodeoxycholic acid biosynthesis, in, 296 human bile, in, 291, 293 metabolism of, 315, 318 3P.12 a-Dihydroxy-5-cholenoic acid, occurrence of, 291, 292 sulfate of, 234 3a,7a-Dihydroxy-5/3-cholestan-26-oic acid, biosynthesis of, 298 chenodeoxycholic acid biosynthesis, in, 295 human bile, in, 291, 292 Occurrence of, 286, 288 a,7a-Dihydroxy-5P-cholest-23-en-26-oic acid, Occurrence of, 286, 288 3a,7a-Dihydroxy-5/3-cholest-24-en-26-oic acid, Occurrence of, 286, 288 7a,12 a-Dihydroxy-6cholesten-3-one, formation of, 234 7a,26-Dihydroxy-4-cholesten-3-one, bile acid biosynthesis, in, 235, 259 20,26-Dihydroxyecdysone, formation of, 222 structure of, 222 26,27-Dinor-5P-cholestane-3a,7a,l2 q24.25pentol, occurrence of, 289, 290 26,27-Dinor-5a-cholestane-3a,7a,l2 a,24-tetrol, occurrence of, 285 26,27-Dinor-5~-cholestane-3a,7a,l2a,24-tetrol, occurrence of, 285 Dinosterol, occurrence of,205 structure of, 205 Dolichol biosynthesis, control of, 66 Durissimasterol, occurrence of, 202 structure of, 202 Ecdysones, biological activity of, 222 biosynthesis of, insects, in, 220, 222 plants, in, 192 metabolism of, 222 occurrence of, 192, 219 structure of, 192, 219 Ecdysone-22-phosphate, Occurrence of, 223 structure of, 223 Ecdysonoic acid, formation of, 223 Occurrence of, 223 structure of, 223 Ecdysteroids, biosynthesis of, 192 insects, in, 219, 220 plants, in, 192 insects, in, 219, 221 Echinodermata, sterols in, 207 Electron microscopy, mixed micelles, of, 395 Electron spin resonance, lipid interactions, studies of, with, 156 mixed micefles, of, 392 Ellipsometry, bile salt films, studies of, with, 362 Emulsification, lipolysis, in, 407 Endocytosis, receptor-mediated, 45 Enterocytes, bile salts, effect of, on, 417 isolation of,411 Enterohepatic circulation, bile acids, 303 bile acid biosynthesis, and, 265 intestinal cholesterol biosynthesis, and, 129 lipid digestion, and, 124, 406 Enteroliths, composition of, 359 20-Epicholanic acids, marine invertebrates, in, 205 Epicholesterol, see 5-Cholesten-3a-01 3-Epi-16-deoxymyxino1, Occurrence of, 280, 284 structure of, 284 Epimerization, microbial, bile acids, of, 334 interspecies, 334 intraspecies, 334 3-Epimyxinol, occurrence of, 280, 284 structure of, 284 436 Epinephrine, HMC-CoA reductase, effect on of, 60 Equilibrium dialysis mixed micelles, of, 392 Ergosterol, biosynthesis of, 178 distribution of, 188 membranes, in 152 structure of 178 Erythrocyte membrane cholesterol in 151 cholesterol-lipid organisation of, in, I64 Estradiol see Oestradiol 24-Ethylidene lophenol, poriferasterol formation of, from, 179 structure of, 179 Ethynyloestradiol, bile acid conjugation, stimulation of, by, 308 bile acid sulfation stimulation of, by 310 Eubacterium sp V.P.I 12708 7a/B-dehydroxylase in, 339 NADPH-flavin oxidoreductase in 339 Fasting, cholesterol 7a-hydroxylase effect on, of 266 HMG-CoA reductase, effect on, of, 60 12a-hydroxylation effect of, on, 245 intestinal cholesterol synthesis, effect on, of, 131 Fatty acids, absorption of 125 choleic acids, in 358 mixed monolayers with, 362 Fatty acid binding protein, lipid absorption in 413 sterol carrier proteins, comparisons with, of, 87 Ferredoxin, mitochondrial 26-hydroxylation in, 250 Ferrodoxin reductase, mitochondrial 26-hydroxylation, in, 250 Ficisterol, biosynthesis of 203 Occurrence of, 203 structure of, 203 “Flip-flop” liposomes in, 163 unilamellar vesicles in, 387 Fluidity, mixed micelles of, 395 Fluidity, (continued) phospholipid-cholesterol dispersions, of 155 Fluorescence, lipid interactions, studies of, with, 156 Fluorescence spectroscopy, mixed micelles, of, 392, 393 Fucosterol, poriferasterol formation of, from, 188 structure of, 175 Fucosterol epoxide, cholesterol formation of, from, 214 Gallbladder, bile acids in, 406 emptying of, 406 Gallstones, ursodeoxycholic acid and, 320 Gangliosides, mixed micelles, in, 394 Glaucasterol Occurrence of, 205 structure of, 205 Glucagon, HMG-CoA reductase, effect on, of, 60 GlucOcorticoids, bile acid conjugation, induction of, by, 308 bile acid sulfation induction of, by, 310 cholesterol 7a-hydroxylase, effect on, of, 266 HMG-CoA reductase, effect on of, 60 intestinal HMG-CoA reductase, effect on, of, 131 Glycocalyx, composition of, 412 Gorgos terol, biosynthesis of, 212 Occurrence of, 203, 204 structure of, 204 Hellibrigenin, structure of, 192 Hemulcholic acid, formation of, 316 Occurrence of, 316 structure of, 316 High-density lipoproteins, HMG-CoA reductase, effect on, of, 60 LCAT, substrates for, as, 105 plasma, in, 44 High-performance liquid chromatography, bile acid CoA derivatives, of, 307 bile acids and salt, of, 348 437 Hippurin-I, occurrence of, 205 structure of, 205 Hollaphyllamine, biosynthesis of, 194 pregnenolone, formation of, from, 194 structure of, 193 Hydrocarbons, absorption of, bile salts and, 421 choleic acids, in, 258 Hydrodynamic radius, bile salt micelles, of, 374, 376 Hydrogen bonding, bile salt micelles, of, 376 Hydrophilic- hydrophobic balance, bile salts, in, 348 bile salt solubility and, 370 12a-Hydroxy-5/3-cholanoic acid, 7a-hydroxylation of, 313 metabolism of, 311 3/3-Hydroxy-5-cholenoicacid, bile acid biosynthesis, in, 233, 258 chenodeoxycholic acid biosynthesis, in, 296 occurrence of, 291, 292, 318 sulfate of, 324 urine, in, 258, 291, 323 3/3-Hydroxy-5/3-cholestan-26-oic acid, occurrence of, 286 7a-Hydroxy-4-cholesten-3-one, allo bile acids, formation of, from, 257 stereochemistry in, 257 bile acid biosynthesis, in, 234 cholestanol, formation of, from, 263 formation of, 244 isotope effect in, 244 7a-Hydroxycholesterol, bile acid biosynthesis, in, 233 25-Hydroxycholesterol, HMG-CoA reductase, effect on, of, 11, 61 26-Hydroxycholesterol, cerebrotendinous xanthomatosis, in, 262 chenodeoxycholic acid, formation of, from, 258 20-Hydroxyecdysone, biosynthesis of, 222 insects, in, 219 marine invertebrates, in, 210 structure of, 210 26-Hydroxyecdysone, metabolism of, 223 26-Hydroxyecdysone, (continued) structure of, 222 2-Hydroxyecdysterone, marine invertebrates, in, 210 structure of, 210 6/3-Hydroxylase, properties of, 312 12a-Hydroxylase, half-life time of, 242 26-Hydroxylase, see 26-Hydroxylation 1-Hydroxylation, bile acids, of, 321 2/3-Hydroxylation, bile acids, of, 322 3a-Hydroxylation, 5/3-cholanoic acid, of, 311 12a-hydroxy-5/3-cholanoicacid, of, 311 a-Hydroxylation, allochenodeoxycholic acid, of, 313 bile acids, of, 322-323 6/3-Hydroxylation, bile acids, of, 322-323 chenodeoxycholic acid, of, 311 deoxycholic acid, of, 312 12a-hydroxy-5~-cholanoic acid, of, 311, lithocholic acid, of, 311 ursodeoxycholic acid, of, 312 7a-Hydroxylation, allolithocholic acid, of, 313 58-cholanoic acid, of, 313 cholesterol, of, 237 deoxycholic acid, of, 313 lithocholic acid, of, 313 7P-Hydroxylation, 3a,6P-dihydroxy-5/3-cholanoicacid, of, 313 rat hepatocytes, in, 314 12a-Hydroxylation, allochenodeoxycholic acid, of, 315 bile acid biosynthesis, regulatory role in, of, 270 biliary drainage, effect of, on, 271 chenodeoxycholic acid, of, 315 cytochrome P-450 in, 245 cytochrome P-450 LM,, and, 242 8-naphthoflavone, effect of, on, 245 starvation, effect of, on, 245 16a-Hydroxylation, deoxycholic acid, of, 315 22s-Hydroxylation, bile acids, of, 316 438 23-Hydroxylation, bile acids of, 316 323 24b-Hydroxylation, cerebrotendinous xanthomatosis, in, 262 25-Hydroxylation cytochrome P-450 LM, and, 242 liver mitochondria, in, 249 26-Hydroxylation, bile acid biosynthesis, in, 235 microsomal cytochrome P-450, in, 249 stereochemistry of, 248 mi tochondrial, biliary obstruction, effect of, on, 249 cytochrome P-450, in, 250 ferredoxin in, 250 ferredoxin reductase, in, 250 stereochemistry of, 248 3-Hydroxy-3-methylglutaryl-CoA reductase (HMG-CoA reductase), activity of, effectors and 60, 266 apo-E receptor and 54 biliary drainage, effect of, on, 266 cholate infusion, effect of, on, 269 cholesterol biosynthesis and, 8-11, 57-65 cholesterol 7a-hydroxylase, relation to of, 239 266 degradation of, 61 developmental pattern of, 58 diurnal rhythm of 58, 266 gene amplification of, 61 inhibitors of, 65 intracellular distribution of, 58 LDL-receptor and 54 levels, control of of, 59 61 lymphatic drainage, effect of, on, 266 mechanism of, membrane fluidity and 64 mevaldic acid and, 10 modulation of, 62 molecular weight of Occurrence of 57 phosphorylation-dephosphorylation of, 62 regulation of 1 , 53, 57-65, 131 mRNA levels and 61 stereochemistry of, 10 substrate specificity of, 10 tissue distribution of 58 2-protein and, 64 3-Hydroxy-3-methylglutaryl-CoAsynthetase, acyl-CoA derivatives, binding of, to, cholestyamine, effect of, on, enzyme-bound intermediate in, levels, alterations in, of, 65 mechanism of, regulatory role of, 6, 65 7a-Hydroxy-3-oxo-4-cholenoic acid, chenodeoxycholic acid, formation of, from, 258 metabolism of, 318, 319 3u-Hydroxysteroid dehydrogenase, bile acid biosynthesis, in, 247 bile acid metabolism, in, 317 Clostridium perfringens, in, 335 Eubacterium lentum, in, 335 properties of, 247, 317 stereochemistry of, 247, 317 subcellular localization of, 247, 317 3b-Hydroxysteroid dehydrogenase, alcohol dehydrogenase and, 318 bile acid metabolism, in, 317 Clostridium perfringens, in, 335 Eubacterium lentum, in, 335 stereochemistry of, 317 subcellular localization of, 317 a-Hydroxysteroid dehydrogenase, Clostridium sp., in, 335 Eubacterium lentum, in, 335 68-Hydroxysteroid dehydrogenase, Clostridium sp., in, 335 Eubacterium lentum, in, 335 7a-Hydroxysteroid dehydrogenase, B fragilis, in, 336 Escherichia coli, in, 336 7p-Hydroxysteroid dehydrogenase, Clostridium absonus, in, 337 Eubacterium aerofaciens, in, 337 Peptoslreptococcus productus, in, 337 12 a-Hydroxysteroid dehydrogenase, Clostridium leptum, in, 337 E lentum, in 338 38-Hydroxy-d-steroid oxidoreductase, inhibitor of, 245 Hyocholic acid, 7u-dehydroxylation of, 312 formation of, 312 meconium, in, 324 Occurrence of, 312 structure of 312 439 Hyodeoxycholic acid, formation of, 312 metabolism of, 313 occurrence of, 312 structure of, 312 Hypercholesterolemia, familial, types of, 51, 54,56 LDL-receptors and, 51, 54, 56 lipoproteins in, 164 Infrared spectroscopy, lipid interactions, studies of, with, 156 Insects, ecdysteroids in, 219 sterol metabolism in, 213 Insertion of A** double bond, poriferasterol, formation of, in, 188 stereochemistry of, 188 Insulin, HMG-CoA reductase, effect on, of, 60 Intermicellar concentration, definition of, 373 mixed micellar solutions, of, 392 Intestinal cholesterol, pools of, 144 biosynthesis of, 125-132 Intestinal microflora, bile acid metabolism, and, 331 Isofucosterol, biosynthesis of, 181 poriferasterol, formation of, from, 179 structure of, 175 Isomerization A* + A', animals, in, 35-36 plants, in, 187 Isopentenyl pyrophosphate isomerase, isotope effects with, 17 lability of, 15 mechanism of, 16 stereospecificity of, 15 substrate analogs of, 15 substrate specificity of, 15 24-Isopropylcholesterol, occurrence of, 201 structure of, 201 Isotope effect, cholesterol 7a-hydroxylation, in, 241 7a-hydroxy-4-cholesten-3-oneformation, in, 244 Krafft point, definition of 371 L, phase, composition of, 410 Lanosterol, 2,3-oxidosqualene, formation from, of, 27 photosynthetic tissues, absence in, of, 184 structure of, 184 Lateral diffusion, cholesterol, effect of, on, 157 phospholipids, of, 158, 386 Lathosterol, membranes, in, 152 Latimerol, occurrence of, 280,283 structure of, 284 LDL receptor, bile acids, effect of, on, 270 HMG-CoA reductase and, 54 Lecithin:cholesterol acyltransferase, assay of, 103 deficiency, familial, of, cornea deposits in, 110 erythrocyte abnormalities in, 109 kidney abnormalities in, 110 lipoprotein abnormalities in, 109 high-density lipoproteins as substrates of, 105 molecular weight of, 103 phosphatidylcholine: lysophosphatidylcholine acyltransferase activity of, 105 phospholipase A, activity of, 103 plasma lipoproteins, effects on, of, 105 Lichesterol, structure of, 188 Light cycling, intestinal cholesterol synthesis and, 131 Light scattering, bile salt micelles, of, 376 mixed micelles, of, 392 Lingual lipase, lipid digestion, role in, of, 409 Lipid absorption, bile acids in, 405-422 Lipid digestion, bile acids in, 405-422 liquid crystalline vesicles in, 397 mixed micelles in, 397 Lipid malabsorption, bile deficiency and, 422 Pluronic F68,effect of, on, 422 Pluronic L-81,effect of, on, 422 Lipid peroxidation, cholesterol, and, 237 440 Lipid uptake, mixed micelles from, 415 Lipoproteins, abnormal, 44 chemically modified, 44 hypercholesterolemia, in, 164 liver disease, in 164 normal, 41 plasma, in, 41 Lipoprotein lipase, function of, 122 Lipoprotein receptors acetyl-LDL, for 50 apo-E, for, 48 cholesterol ester-protein complex and, 51 diseases related to, 54 LDL, for, 45 LDL-dextran sulfate and, 50 life cycle of, 47, 51 regulation of, 52-54 P-VLDL, for, 49 Lipoprotein uptake, intestinal, function of, 135 localization of, 133 methods of study of, 132 regulation of, 134 villus-crypt gradient and, 135 Liposomes, cholesterol exchange, studies of, with, 163 cholesterol “flip-flop” in, 163 permeability of, 159 Liquid crystalline bilayers, bile salts, in, 384-387 Liquid crystalline vesicles, bile, in, 396 lipid digestion, in, 397 Lithocholic acid, brain, in, 320 formation of, 334, 338 6/3-hydroxylation of, 311-312 7a-hydroxylation of, 313 Lithocholic acid sulfate formation of, 309, 334 microbial metabolism of, 334 occurrence of, 309 Liver disease bile acids in, 291, 321-324 lipoproteins in, 164 Low-density lipoproteins, degradation of, intestine, in, 133 plasma, in, 43 receptor for, 45-48 Lymphatic cholesterol, amount of, 141 newly synthesized, 142 origin of, 141 Lymphatic drainage, cholesterol 7a-hydroxylase, effect on, of, 266 HMG-CoA reductase, effect on, of, 266, 269 Macdougallin, Occurrence of, 186 structure of, 186 Makisterone A, Occurrence of, 220 structure of, 220 Malaria, membrane permeability and, 166 Marine invertebrates, sterols in, 199 analysis of, 199 Mass spectrometry, bile alcohols, of, 281 cholesterol 7a-hydroxylase, assay of, with, 238 Meconium, bile acids in 324 Membrane fluidity, cholesterol and, 169 HMG-CoA reductase and, 64 Membrane permeability, cholesterol and, 169 plant sterols and, 168 Membrane proteins, cholesterol and, 159, 160 Membrane sterols, plant cells, in, 196 3-Methylbutenyl pyrophosphate, cholesterol biosynthesis, in, 14 22-Methylenecholesterol, biosynthesis of, 203 Occurrence of, 203 structure of, 203 (22 R ,23R)-Methylenecholesterol, biosynthesis of, 203 occurrence of, 203 structure of, 203 24Methylene cycloartanol, formation of, 182 structure of, 182 441 24-Methylene lanosterol, photosynthetic tissues, absence in, of, 184 structure of, 184 24-Methylene lophenol, formation of, 182, 185 structure of, 182 26-Methylstrongylosterol, occurrence of, 202 structure of, 202 25-Methylxestosterol, occurrence of, 202 structure of, 202 Mevalonate kinase, cholesterol biosynthesis, in, 12 levels, alterations in, of, 65 Mevalonate phosphate kinase, levels, alterations in, of, 65 Mevalonate-5-phosphotransferase, see Mevalonate kinase Mevalonate-5-pyrophosp hate, cholesterol biosynthesis, in, 13 Mevalonate pyrophosphate decarboxylase, levels, alterations in, of, 65 Mevalonolactone, HMG-CoA reductase, effect on, of, 60 Mevinolin, HMG-CoA reductase, interaction with, of, 11 Micellar phase, lipids during digestion, of, 414 Micelles, bile salts, of, calcium binding to, 379 charge of, 378 coulombic interactions in, 378 counterion binding to, 348, 378, 382 density of, 351 formation of, 372 hydration of, 375 hydrodynamic radius of, 374, 376 hydrogen bonding of, 376 light scattering of, 376 lipid digestion, in, 407 NMR, studies with, of, 378, 379 polydispersity of, 375 quasi-elastic light scattering of, 374 relaxation processes in, 379 reversed, non-aqueous media, in, 382 self-association of, 379-382 shape of, 375 Micelles, bile salts, of, (continued) size of, 373-375 structures of, 377 van der Waals interactions in, 377 Microorganisms, intestinal, bile acid metabolism and, 331 Mitochondria1 membranes, cholesterol translocation in, 85 Mixed micelles, bile, in, 392 bile salt-bile acid, of, 365-369 bile salt-fatty acid, diffusion coefficient of, 415 bile salt-hydrocarbon, 388-389 bile salt-insoluble amphiphile, 389 bile salt-soluble amphiphile, 393-394 bile salt-swelling amphiphile, 390-393 bile salt-swelling amphiphile-insoluble amphiphile, 394-395 cholesterol in, 394-395 critical micellar concentrations of, 373 electron microscopy of, 395 electron spin resonance, studies with, of, 392 equilibrium dialysis of, 392 fluidity of, 395 fluorescence spectroscopy, studies with, of, 392, 393 formation of, 388-397 gangliosides in, 394 intermicellar concentrations, and, 392 light scattering, studies with, of, 392 lipid digestion, in, 397, 407 lipid transport, in, 415 lipid uptake, in, 415 NMR, studies with, of, 392 phase transition temperature of, 393 phospholipids in, 390-393 quasi-elastic light scattering, studies with, of, 392 scanning calorimetry, studies with, of, 392 size of, 391, 395 unilamellar vesicles, transition to, of, 395-396 X-ray scattering, studies with, of, 392 Mixed monolayers, bile acid-fatty acid, of, 362 bile acid-phospholipid, of, 362 condensing effects in, 362 Model membranes, bile salts in, 384-387 cholesterol in, 384-387 442 Model membranes, (ronfmued) NMR studies with, of, 384-387 phospholipids in, 384-387 reverse micelles in, 384 387 transport through, 387 X-ray diffraction of 384 Molar volumes, bile salts of 351 Mollusca sterols in 210 Monogl yceriden, mixed micelles, in 390 392 Monolayers, bile acids of 359 bile salts, of 346 phospholipids, of, 158 sterols effects of on, 153 158 Monooxygenases cholesterol biosynthesis, in 31 a-Muncholic acid, chenodeoxycholic acid formation from, of 311 56-cholanoic acid, formation from, of, 31 /3-muricholic acid, formation of, from, 314 precursors of, 311-312 structure of, 311 /Y-Muricholic acid, chenodeoxycholic acid, formation from, of 31 5,Ll-cholanoic acid, formation from, of 31 cholestasis in, 312 3a,6P-dihydroxy-5P-cholanoicacid formation from, of 313 microbial metabolism of, 335 a-muricholic acid, formation from, of 314 precursors of, 311-312 structure of, 31 w-Muricholic acid, hyodeoxychotic acid, formation From, of 31 microbial formation of, 335 fi-muricholic acid, formation from, of, 313 structure of 313 iMuristerone, hormonal activity of 223 structure of, 223 Muscular dystrophy sarcoplasmic reticulum in, 166 Myelin, cerebrosides in, 151 cholesterol in 151 Myxinol, Occurrence of, 280, 284 structure of 284 N a + and K + transport, cholesterol, effect of, on, erythrocytes, in 161 fibroblasts, in, 161 thymocytes, in, 161 NADPH-cytochrome P-450 reductase, cholesterol 7a-hydroxylation, and, 240 Na '/K +-ATP-ase, cholesterol, inhibitory effect of, on, 160 thymocytes, in 160 Nodonside, occurrence of 208 structure of, 208 Non-absorbable marker, lipid absorption studies, use in, of, 411 Non-micellar phase, lipids during digestion, of, 416, 417 27-Nor-5/3-cholestane-3a,7a,I a,24,25-pentol, Occurrence of, 289, 290 27-Nor-5P-cholestane-3~,7a,l2a,25-tetrol, occurrence of 289, 290 Norcholic acid, N M R analysis of, 348 1-Norcycloartenol, formation of, 185 structure of, 185 25-Nor-26-deoxy-5a-ranol, Occurrence of, 280, 285 structure of 285 25-Nor-26-deoxy-SP-ranoI, Occurrence of, 280, 285 structure of, 285 Norepinephrine, HMG-CoA reductase, effect on, of, 60 A-Norsterols, Occurrence of, 203 structures of, 203, 204 Nuclear magnetic resonance spectroscopy, bile acid structure studies of, with, 346-348 bile salts in model membranes, studies of, with 385 bile salt micelles, studies of, with, 378, 379 cholesterol in erythrocyte membrane, studies of, with, 155 lanthanide probe in, 347 lipid interactions, studies of, with 155 mixed micelles, of, 392 model membranes, studies of, with, 384-387 443 Obtusifoliol, demethylation of, 186 formation of, 183 structure of, 183 Occelasterol, occurrence of, 211 structure of, 211 Oestradiol, marine invertebrates, in, 208 Oestrone, plants, in, 190 Oil phase, emulsified, 417 lipids during digestion, of, 409, 414 Oo-ecdysteroids, insects, in, 221 Oogoniol, formation of, 197 structure of, 197 Ornithocholic acid, occurrence of, 307 /%Oxidation, bile acid biosynthesis, in, 235, 252 2,3-Oxidosqualene formation of, 27 7-Oxolithocholic acid, metabolism of, 312 A4-3-Oxosteroid 5a-reductase, allo bile acids, formation of, in, 257 bile acid metabolism, in, 319 stereochemistry of, 257, 319 A4-3-Oxosteroid5P-reductase, bile acid biosynthesis, in, 246 bile acid metabolism, in, 319 stereochemistry of, 246, 319 Pancreatic lipase, colipase and, 408 lipid digestion, in, 408 Permeability, liposomes, of, 159 model membranes, of, 387 bile salts, effect of, on, 387 Peroxisomes, bile acid biosynthesis, in, 253 Zellweger’s disease, absence in, of, 263 a-Petromyzonol, occurrence of, 280, 285 structure of, 285 5P-Petromyzonol, occurrence of, 280, 285 structure of, 280 Petrosterol, occurrence of, 202 structure of, 202 Phase transition temperature, mixed micelles, of, 393 Phenobarbital, bile acid glucuronidation, induction of, by, 310 bile acid hydroxylation, effect on, of, 323 cholesterol 7a-hydroxylation, and, 241 a-Phocaecholic acid, see 3a,7a,12a,23-Tetrahydroxy-5/3-cholanoic acid /3-Phocaecholic acid, see 3a,7a,23-Tnhydroxy-5/3-cholanoic acid Phospholipase A,, bile salt requirement of, 409 substrates of, 409 Phospholipids, absorption of, bile salts and , 419 digestion of, phospholipase A , by, 409 liquid crystalline bilayers, in, 385-387 mixed micelles, in, 390-393, 407 mixed monolayers with, 362 Phospholipid exchange protein, sterol carrier proteins, comparisons of, with, , 90 Phosphomevalonate kinase, cholesterol biosynthesis, in, 12 Phosphorylation-dephosphorylation, ACAT, of, 101, 139 cholesterol 7a-hydroxylase and, 243, 268, 270 HMG-CoA reductase, of, 11, 62, 270 Physical constants, bile acids and salts, of 349-351 Phytosterol metabolism inhibition of, 217, 218 insects, in, 213 PKa, bile acids, of, 366-369 Plasma lipoproteins, cholesterol, association of,with, 97 cholesterol esters, association of, with, 97 cholesterol esters, formation of, in, 108 cholesterol esters, metabolic role of, in, 107 cholesterol esters, removal of, from, 109 444 Pluronic F68, cholesterol absorption and, 419 lipid malabsorption and, 422 Pluronic L-81, lipid malabsorption and, 422 Polydispersity bile salt micelles of, 375 index of, 374 Poriferasterol 22-dehydroclerosterol formation from, of 180 demethylation and, 186 22-desaturation and, 188 ethylidene lophenol, formation from of 179 isofucosterol formation from of 179 structure of 175 Portacaval anastomosis bile acid biosynthesis effect on of, 265 Pregnenolone, cardenolide biosynthesis, in 190 hollaphyllamine biosynthesis in 194 Prenyltransferases, fluorine analogs and, 20 2-fluoro-farnesyl pyrophosphate, binding of to 18 kinetics of 20 mechanism of, 19 metal ions and 19 polymerization termination of, by, 21 substrate analogs of, 22 substrate binding to 18 Z-and E-prenols, synthesis of by 18 Progesterone, marine invertebrates in 208 plants, in 190 Prolactin HMG-CoA reductase effect on of 60 Prothoracic gland ecdysone, secretion of from, 220 Prothoraco-ecdysteroids, insects in, 221 Pyrophosphomevalonate decarboxylase mechanism of, 14 Pythocholic acid, formation of,315 occurrence of 31.5 structure of 315 Quasi-elastic light scattering (QLS), bile salt micelles of 374 mixed micelles of 392 5a-Ranol, Occurrence of, 280 284 structure of, 284 5,l-Ranol biosynthesis of, 298 cholic acid biosynthesis and, 295 Occurrence of, 280 284 structure of, 284 Relaxation processes, bile salt micelles, in 379 Retinol, absorption of, bile salts and, 420 Sapogenins biosynthesis of, 192 plants, in, 192 Saponins marine invertebrates, in, 208 toxicity of, 209 Sarcoplasmic reticulum, cholesterol in 166 Scanning calorimetry, lipid interactions, studies of, with, 154 mixed micelles of, 392 SCP, see Sterol carrier protein, SCP, see Sterol carrier protein Scymnol, cholic acid biosynthesis, and, 295 Occurrence of 280, 281 structure of, 281 9.1 1-Secogorgost-5-me-3.1t-diol-9-one, occurrence of, 205 structure of 205 Self-association, bile acid esters, of 382 bile salt micelles of, 379-382 Sepositoside A occurrence o f , 208 structure of 208 Sex differences bile acids of, liver, in, 305 Sitosterol, biosynthesis of 181 structure of, 175 Solasodine, biosynthesis of, 194 structure of, 193 445 Solubility, bile acids and salts, of, 365-372 Sponges, sterols in, 201 Squalene epoxidase and cyclase, 2-aza-2,3-dihydrosqualene, inhibition by, of, 30 cytoplasmic effectors and, 27 20,21-dehydrooxidosqualene,cyclization of, by, 30 2,3-iminosqualene, inhibition by, of, 29 mechanism of, 28 NADPH-cytochrome c reductase in, 27 2,3-oxido-10,15-bisnorsqualene,cyclization of, by, 30 Squalene 2,3-oxide:cycloartenol cyclase, cycloartenol, formation of, by, 177 Squalene synthetase, kinetics of, 24 lycopersene, formation of, by, 24 mechanism of, 25 presqualene pyrophosphate and, 23 solubilization of, 23 substrate analogs of, 24, 25 Stelliferasterol, occurrence of, 201 structure of, 201 Steroid alkaloids, biosynthesis of, 194 structures of, 193 Steroid hormones, biosynthesis of, plants, in, 190 function of, plants, in, 197 plants, in, 190 A6-Steroid reductase, microbial bile acid metabolism, in, 341 Sterol absorption, human intestine, in, 125 Sterol acylglycosides, biosynthesis of, plants, in, 196 plants, in, 196 Sterol biosynthesis, control of, 57, 66 Sterol carrier protein,, sterol biosynthesis, participation in, of, 75 properties of, 75 purification of, 74 substrate specificity of, 74 Sterol camer protein,, adrenal, in, 84 antibody against, 79 Sterol carrier protein,, (continued) cholesterol biosynthesis, participation in, of, 77 cholesterol esterification, participation in, of, 80 cholesterol 7a-hydroxylase, effect on, of, 81 cholesterol transfer and, 82 cholesterol translocation and, 85 kinetics of, 78 purification of, 77 substrate specificity of, 78 Sterol esters, plants, in, 196 Sterol evolution, membrane permeability, and, 168 Sterol function, membranes, in, 31 plant cell membranes, in, 196 Sterol glycosides, biosynthesis of, plants, in, 196 plants, in, 196 Sterol requirement, insects, in, 219 Sterols, coelenterata, in, 204 marine invertebrates, in, 199 sponges, in, 201 C,,-sterols, marine invertebrates, in, 211 5,24-Stigmastadien-3P-o1, metabolism of, 181 structure of, 181 Stigmasterol, dealkylation of, 215 occurrence of, 152 structure of, 152 Stress, HMG-CoA reductase, effect on, of, 60 Strongylosterol, Occurrence of, 201 structure of, 201 Subcellular distribution, bile acids of, liver, in, 305 Sulfotransferase, bile acid sulfation, in, 309 diurnal variation of, 310 induction of, 310 Surface pressure-area isotherms, bile acid monolayers, of, 359 Surface tension, bile salts, of, 360 446 Tangier disease, apolipoprotein Al, processing of, in, 110 Taurocholic acid, absorption of, 416 Taurodeoxycholic acid 7a-hydroxylase, properties of, 314 Testosterone, plants, in, 190 18,3a,7a,l2a-Tetrahydroxy-5/3-cholanoicacid, cholic acid, formation from, of, 321 meconium, in, 324 Occurrence of, 321 2~,3a.7a.12a-Tetrahydroxy-5~-cholanoic acid, occurrence of, 322 aY,6a.7a 12a-Tetrahydroxy-5~-cholanoic acid, occurrence of, 322 3a,7a,l2 a.23 a-Tetrahydroxy-58-cholanoicacid, formation of, 316 Occurrence of 316, 323 2~,3a.7a.l2a-Tetrahydroxy-5~-cholestan-26-oic acid, Occurrence of 286, 287 3a,7a,l2a,22-Tetrahydroxy-5/3-cholestan-26-oic acid, Occurrence of 286 287 3a,7a,12a,24-Tetrahydroxy-5~-cholestan-26-oic acid, cholic acid biosynthesis, in, 293-294 human bile, in, 291, 292 lower vertebrates, in, 286, 287 58-ranol formation of, from, 298 stereochemistry of 287, 294 Zellweger’s disease, in 263 3a,7a.12a,24-Tetrahydroxy-24-methyl-5@, cholestanoic acid, Occurrence of, 286 Terrah.vmenu pyrijormis, membrane lipids in 168 Thornasteroid A, occurrence of, 208 structure of 208 Thyroid hormone cholesterol 7a-hydroxylase, effect on of 266 HMG-CoA reductase effect on, of, 60 266 12a-hydroxylation effect on of, 271 26-hydroxylation, effect on, of, 271 intestinal sterol synthesis effect on, of, 131 Titration curves, hile acids and salts, of, 365-369 Tocopheryl acetate, absorption of, 418 Trig1ycerides, absorption of, bile salts and, 419 mixed monolayers with, 364 18.3a.12 a-Trihydroxy-5~-cholanoicacid, deoxycholic acid, formation from, of, 321 occurrence of, 321 3a,6a,12 a-Trihydroxy-5~-cholanoic acid, Occurrence of, 322 3a,6B, 12a-Trihydroxy-5j3-cholanoic acid, deoxycholic acid, formation from, of, 312 Occurrence of, 312, 322 3a,78,12 a-Trihydroxy-5b-cholanoicacid, metabolism of, 314 Occurrence of, 314 polarity of, 349 3a,7a,23-Trihydroxy-5~-cholanoic acid, Occurrence of, 316 3a,12 a,23-Trihydroxy-5/3-cholanoicacid, formation of, 316 occurrence of, 316 3a.7a.12 a-Tri hydroxy-5B-cholestan-26-al, metabolism of, 251 3a,7a,12 a-Trihydroxy-5a-cholestan-26-oic acid, occurrence of, 286, 288 synthesis of, 288 12a-Trihydroxy-5~-choIestanoic acid, 3a,7a, bile acid biosynthesis, in, 235 biosynthesis of, 298 cholic acid, formation of, from, 352 formation of, 251, 293 human bile, in, 291, 292 lower vertebrates, in, 286, 287 peroxisomes, metabolism in, of, 253 stereochemistry of, 287, 292 stereoisomers of,287 Zellweger’s disease, accumulation in, of, 263 acid, 3a,7a,22-Trihydroxy-5~-cholestan-26-oic occurrence of 286, 288 3a,7a,24-Trihydroxy-5j3-cholestan-26-oic acid, Occurrence of, 286, 288 3a.7a,12 a-Trihydroxy-5a-cholest-22-ene-24carboxylic acid, Occurrence of, 286 287 3a,7a,l2 a-Tri hydroxy-5&cholest-22-ene-24carboxylic acid, occurrence of, 286 447 a,7a,12 a-Trihydroxy-5P-cholest-23-en-26-oic acid, occurrence of, 286, 288 stereochemistry of, 288 3a,7a,12a-Trihydroxy-5~-cholest-24-en-26-oic acid, occurrence of, 286, 288 3a,7a,l2 a-Trihydroxy-27a,27b-dihomo-5Pcholestane-26,27b-dioic acid, serum, in, 291,292 3a,7a,12 a-Trihydroxy-26,27-dinor-5~-cholestan24-one, occurrence of, 289, 290 3a,7a,12 a-Trihydroxy-24-methyl-5ficholestanoic acid, occurrence of, 286 Triiodothyronine, HMG-CoA reductase, effect on, of, 60 UDP-glucuronosyltransferase, bile acid glucuronidation and, 310 induction of, 310 purification of, 310 Unilamellar vesicles, mixed micelles, transition of, to, 395-396 size of, 395 Unstirred water layer, diffusion barrier, as, 412 intracellular lipid transport and, 413 structure of, 412 Urine, bile acids in, 258, 291, 292, 321-324 bile alcohols in, 289, 290 Ursodeoxycholic acid, galldones and, 320 6P-hydroxylation of, 312 metabolism of, 320 microbial metabolism of, 337 occurrence of, 314 polarity of, 349 van der Waals interactions, bile salt micelles, in, 377 choleic acids, in, 358 Varanic acid, see 3a,7a,l2 a,24-Tetrahydroxy-SP-cholestan26-oic acid Verongulasterol, biosynthesis of, 213 occurrence of, 201 structure of, 201 Very-low-density lipoproteins, metabolism of, 122 plasma, in, 42 Villus-crypt axis, intestinal cholesterol synthesis and, 127 LDL uptake and, 135 Viscous isotropic phase, composition of, 410 Vitamins, absorption of fat-soluble, bile salts and, 420 polyunsaturated fatty acids and, 421 Vitamin C deficiency, bile acid biosynthesis, effect on, of, 267 cholesterol biosynthesis, effect on, of,267 Withanolides, biosynthesis of, 194 structures of, 194 Wolman syndrome, genetic defects in, 48, 56 Xestospongesterol, biosynthesis of, 213 occurrence of, 201 structure of, 201 Xestosterol, biosynthesis of, 213 occurrence of, 201 structure of, 201 X-ray diffraction, lipid interactions, studies of, with, 158 liquid crystalline bilayers, of, 384 X-ray scattering, mixed micelles, of, 392 Zellweger’s disease, bile acids in, 291, 292 bile acid biosynthesis in, 263 peroxisomes, lack of, in, 263 3a,7a,12a,24-tetrahydroxy-5/3-cholestanoic acid in, 263 3a,7a,l2a-trihydroxy-5~-cholestanoic acid in, 263 Z-protein, HMG-CoA reductase, modulation of, by, 64 This Page Intentionally Left Blank .. .STEROLS AND BILE ACIDS New Comprehensive Biochemistry Volume 12 General Editors A NEUBERGER London L.L.M van DEENEN Urrecht ELSEVIER AMSTERDAM NEW YORK OXFORD * * Sterols and Bile Acids. .. Cataloging-in-Publication Data Main entry under title Sterols and bile acids (New comprehensive biochemistry: v 12) Includes bibliographies and index Sterols 1Metabolism.2 Bile acids- Metabolism I Danielsson Henry... primitive bile acids in mammals V V I Metabolism of bile alcohols and primitive bile acids in mammals V l i Metabolism of bile alcohols and primitive bile acids