flo Hx; -,"- c H 2- c ti a-, 7a-, and IZG-OH group specific enzymic analysis of biliary bile acids: comparison with gas-liquid chromatography
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1 3-, 7-, nd IZG-OH group speifi enzymi nlysis of biliry bile ids: omprison with gs-liquid hromtogrphy In A. Mdonld,. Noel Willims, nd Bonnie. Musil Deprtment of Mediine, Dlhousie University, Hlifx, N.S., nd Summry 3-Hydroxysteroid dehydrogense (3-HSDH) from P. testosteroni, 7-HSDH (Esherihi oli AT #29532) nd I2-HSDH (lostridium group P, strin 48-50, AT #29733) were used to diretly mesure 3-, 7-, nd 12-OH groups in extrted humn bile-rih duodenl spirtes. Twelve smples hosen for widely differing rtios of holid henodeoxyholi/deoxyholi were omputed by solving three simultneous equtions. omprison of these rtios with those obtined by ) thin-lyer hromtogrphy nd 3- nd 7-HSDH ssys nd b) gs-liquid hromtogrphi nlysis showed no signifint differene. Addition of known niounts of pure holi, henodeoxyholi, deoxyholi, or lithoholi id to individul bile extrts gve n pproprite yield of' 3-, 7-, nd 12-OH groups. The diret (non-hromtogrphi) enzymi method hs the dvntges of being rpid, onvenient, nd inexpensive, nd thus suitble for linil use.-mdonld, I. A.,. N. Willims, nd B.. Musil. 3-, 7-, nd 124-OH group speifi enzymi nlysis of biliry bile ids: omprison with gsliquid hromtogrphy.]. Lipid Res : Abbrevitions:, holi id; D, henodeoxyholi id; D, deoxyholi id; L, lithoholi id, denine dinuleotide; NADP, /3-niotinmide denine dinuleotide phosphte; HSDH, hydroxysteroid dehydrogense; GL, gs-liquid hromtogrphy; TL, thin-lyer hromtogrphy. Supplementry key words 3-, 7-, nd 12-hydroxysteroid dehydrogenses. heptofluorohutyrtes Individul bile ids n be quntified by gs-liquid hromtogrphy ( 1-4) nd seprted by thin-lyer hromtogrphy (TL). Thin-lyer hromtogrphy is usully ombined with enzymi or hemil methods to mesure individul bile ids (5, 6). The disdvntge of TL is the filure to seprte bile id omponents suh s the glyo- nd turo-onjugtes of isomeri, -dihydroxy-5/3-holnotes. Additionlly, TL requires preprtive lensing, nd the elution of bile slts from sili is inomplete. In this ommunition we report the diret, non- HO Hx; -,"- H 2- ti flo TAUROHOLATE D [Tjx 10-6M Fig. 1. Stndrd urve for 3-HSDH (losed irles, 0-O), 7-HSDH (losed tringles, A-A), nd 12~-HSDH (losed squres, - m) using turoholte s substrte. Assys were performed in duplite. Downloded from by guest, on August 22, 2018 Journl of Lipid Reserh Volume 21, 1980 Notes on Methodology 381
2 TABLE 1. omprison of the rtios of holidhenodeoxyholiddeoxyholi ids nd totl bile id onentrtions by diret enzymi ssys (), gs-liquid hromtogrphy (b), nd thin-lyer hromtogrphy nd 3- nd 7-HSDH ssys () Perentge omposition Smple" holi henodeoxyholi Deoxyholi Totl mm 1 b '3 2 b b h b 6 h 7 h 8 b 9 h d IO b 11 h i o I o Downloded from by guest, on August 22, b 55.8.io.o I Averge vlues t 1 SD d h 49.1 i t t i i t t t i r t 20.9 Norml (N = 7)b 42.5 i ? * 7.4 " All bile smples were obtined from feiirle subjets; smples 1-4 were eh obtined from ptients with gllstones (rdiologilly norl-visu1iz.d gllbldder, smple 4); smples 5-8 from norml women tking orl ontreptives, srnple 9 from n infnt with eli disese, nd smples from noi-ml w~1111e11 on no tnetlitiorl.!' Referene # 19. hromtogrphi use of three group-speifi bile id hydroxysteroid dehydrogenses (HSDH) to rpidly ompute the rtios iid mounts of the three min bile ids in humn biliry extrts. We ompre these rsults with those derived both from L nd TL s previously desribed (4-7). 382 Journl of Lipid Reserh Volume 2 1, 1980 Notes on Mrthodology
3 TABLE 2. orreltion oeffiients (r vlues) for omprison of the perentge omposition nd totl bile id omposition heno- # omprison holi deoxyholi Deoxyholi Totl 1 A'versus Bb A versus Bversus A, diret enzymi ssy. B, gs-liquid hromtogrphy., thin-lyer hromtogrphy nd enzymi ssy. % MATERIALS 3-Hydroxysteroid dehydrogense ws purhsed from Worthington Enzymes, Freehold, NJ. All bile id stndrds were obtined from lbiohemils, Los Angeles, A, nd /3-niotinmide denine dinuleotide (NAD) denine dinuleotide phosphte (NADP) were obtined from Sigm hemils, St. Louis, MO. METHODS 7- nd 1 2-Hydroxysteroid dehydrogenses 7- nd 1 P-hydroxysteroid dehydrogenses were prepred s desribed erlier (7,8). Lyophilized preprtions were stored t -20. Extrtion of bile-rih duodenl spirtes Bile-rih duodenl spirtes were olleted s desribed before (9) nd extrted ording to Folh, Lee, nd Slone Stnley (10) nd nlyses were performed in duplite. The ombined top phses were evported to dryness, reonstituted into volume of methnol-3% hydrogen peroxide solution 4: 1 identil to tht of the originl liquot. Aspirtes were olleted from norml women tking orl ontreptives (for high holi nd low deoxyholi id proportion), ptients with gllstones, ptient with non-funtioning gllbldder (for high deoxyholi id proportion), nd ptient with eli disese on tetryline (for low deoxyholi id proportion). Spetrophotometri ssy systems for 3-, 7-, nd 12-OH groups in biliry extrts 3-OH Groups. uvettes ontined 0.9 ml of 1.0 M glyine/noh buffer ph 9.5, 50 p1 of 53 mm NAD, 1-10 p1 of extrted bile ids in solvent (lo), nd 20 p1 of freshly prepred P. testosteroni 3-HSDH (4 mg/ml distilled wter). All onstituents (exept the enzyme) were introdued into the uvette, mixed thoroughly, nd red t 340 nm in Bekmn DB-GT spetrophotometer equipped with 10 in reorder. The enzyme preprtion ws introdued subsequently, nd the uvette ws monitored until no further bsorbne ould be mesured; the totl bsorbne t 340 nm ws reorded. Totl 3-OH groups were omputed on the bsis of the 'NADH = 6.2 x lo3 (11). All ssys were performed in duplite. 7-OH Groups. The ssy system desribed for 3- OH groups ws utilized exept tht 10 pl of solution of lyophilized E. oli 7-HSDH (5 mg/ml distilled wter) ws used insted of 3-HSDH. 12-OH roups. The ssy system desribed for 3-OH groups ws utilized exept tht 20 PI of solution of lyophilized lostridium group P strin HSDH (10 mg/ml) ws used insted of 3- HSDH, nd NADP ws used insted of NAD. TABLE 3. Reovery of bile id stndrds on ddition to smple in uvette nd stndrd bile id ssys Downloded from by guest, on August 22, 2018 Finl Absorbne hnge t 340 nm Perent Reovery of Hydroxyl Group on Addition of Stndrd to Smple # uvette ontents 3- HS D H 7-HSDH 12-HSDH ~Q-HSDH 7 - ~ i2-nsdh ~ ~ ~ 2.5 p1 duodenl bile smple lone 2.5 p1 duodenl bile smple + 10 p1 2 mm holi 2.5 p1 duodenl bile smple + 10 p12 mm D 2.5 pi duodenl bile smple + 10p12mMD 2.5 pl duodenl bile smple + 10pl2mML Mesured stndrd bile ids dded 10 pl 2 mm holi 10 pl 2 mm D 10 pi 2 mm D 10 p12 mm L t t k k IO ? t k t k t ? k 0 Journl of Lipid Reserh Volume 21, 1980 Notes on 'Methodology 383
4 lultion of the rtio of holi henodeoxyholi deoxyholi ids The rtio of holi/henodeoxyholi/deoxyholi ids ws omputed by solving three simultneous equtions s previously proposed ( 12): A,, = k(() + (D) + (D)) A,, = k(() + (D)) AI,, = k(() + (D)) where A,,, A7,, nd AI2, re the bsorbne vlues of the NAD(P)H produed nd (),(D), nd (D) represent the finl onentrtions of holi, henodeoxyholi, nd deoxyholi ids. The onstnt k reltes bsorbne to the bile id onentrtion nd is essentilly identil to the E vlue of NAD(P)H whih is 6.2 x lo3. All nlyses were performed under onditions where these retions go to ompletion. Anlysis of bile ids by gs-liquid hromtogrphy The rtio of /D/D ws lso determined by gs-liquid hromtogrphy fter derivtiztion of the extrts to the heptofluorobutyrtes (4), nd the results were diretly ompred with both the diret nd hromtogrphi enzymi pprohes. RESULTS AND DISUSSION Superimposble stndrd urves for turoholte s estimted by eh individul enzyme (3-, 7-, nd 12-HSDH) re shown in Fig. 1. Using 0.1 M glyine/ NOH buffer nd in the bsene of hydrzine, we were ble to hieve omplete oxidtion of 3-, 7-, nd 12-OH groups of both onjugted nd unonjugted bile ids with three group-speifi enzymes. The bile id perentge omposition s mesured by the three methods for ll 12 smples is shown in Tble 1; published vlues for norml subjets re shown for omprison ( 13). There is lose greement mong the three methods s shown by omprison of the verges s well s by the orreltion oeffiients (Tble 2). As n be seen, the omprison of the rtios determined by the three methods is exellent, with r vlues exeeding 0.90, thus vlidting the diret pproh nd the ssumption tht minor omponents n be negleted in these prtiulr humn bile smples. A omprison of the totl bile id onentrtion in the smple by GL gve slightly lower r vlues (Tble 2). This result presumbly reflets differentil losses by the methods. When known mount of prestndrdized bile id solutions (holi, henodeoxyholi, deoxyholi or lithoholi id) ws dded to uvette ontining n liquot of duodenl bile smple, the reovery in terms of hydroxyl groups of stndrd mesured ws quntittive (Tble 3). Additionlly, the dt demonstrte the bsolute speifiity of the 7- nd 12-HSDH preprtions for their respetive hydroxyl groups, s demonstrted before (7,8, 14-16). It hs been shown erlier tht both 7- nd 12-HSDH ret with both onjugted nd free bile ids (7, 8, 14-16). Thin-lyer hromtogrphy of smples indited tht minor bile ids (lithoholi, ursodeoxyholi nd oxo-bile ids) were present only in tre mount (<5%). It must be emphsized tht the presene of disproportionte mount of ny of these normlly minor omponents would negte the diret method sine it ssumes mixture of the three mjor bile ids, holi, henodeoxyholi, nd deoxyholi id. Thus, in situtions suh s ursodeoxyholi id therpy for dissolution of holesterol gllstones or holestti liver disese (17), this diret enzymi pproh would not detet the inresed mounts of ursodeoxyholi nd lithoholi id, respetively. Additionlly, the presene of bile id-sulftes nnot be deteted by the enzymi method, thus the omposition results reflet the unsulfted form. Although lithoholi sulfte hs been shown to be present in norml humn bile, it represents only very smll frtion of the totl bile id pool (18). Although neither GL nor the diret enzymi method will revel the rtio of glyine to turine onjugted bile ids, the enzymi nlysis fter TL will give this informtion nd non-hromtogrphi methods for estimting this rtio re lso vilble (19, 20). The use of tripleenzyme kit for biliry bile id nlysis would provide n inexpensive, simple, non-hromtogrphi, nd potentilly utomtble method (2 1) for biliry bile id nlysis in linil prtie.m This work ws supported by grnt #MA5075 from the Medil Reserh ounil of nd nd by Dlhousie University Internl Mediine Reserh Fund. We re indebted to Mrs. Sherry Mrthy for her exellent tehnil ssistne. j21nusnpt reeved 25 June 1979 nd zn reused form 16 Otober REFERENES 1. Nir, P. P., nd. Gri A modified gs-liquid hromtogrphi proedure for the rpid determintion of bile ids in biologil fluids. Anl. Biohem. 29: Ross, P. E.,. R. Pennington, nd I. A. D. Bouher Gs-liquid hromtogrphi ssy of serum bile ids. Anl. Biohem. 80: Sndberg, D. H., J. Sjovll, K. Sjovll, nd D. A. Turner Mesurement of humn serum bile ids by gsliquid hromtogrphy. J. Lipid Res. 6: Downloded from by guest, on August 22, Journl of Lipid Reserh Volume 2 1, 1980 Notes on Methodology
5 4. Musil, B.., nd. N. Willims Quntittive ssy of onjugted nd free bile ids s heptfluorobutyrte derivtives by gs-liquid hromtogrphy. J. Lipid Res. 20: Shiod, R., P. D. S. Wood, nd L. W. Kinsell Determintion of individul onjugted bile ids in humn bi1e.j. Lipid Res. 10: Turnberg, L. A., nd A. Anthony-Mote The quntittive determintion of bile slts in bile using thinlyer hromtogrphy nd S-hydroxysteroid dehydrogense. lin. him. At. 24: Mdonld, I. A.,. N. Willims, nd D. E. Mhony Lyophylized 7-hydroxysteroid dehydrogense: stble enzyme preprtion for routine bile id nlysis. J. Lipid Res. 16: Mdonld, I. A., J. F. Jellett, nd D. E. Mhony Hydroxysteroid dehydrogense from lostridium group P strin AT #29733: prtil purifition nd hrteriztion. J. Lipid Res. 20: Willims,. N., J. W. I. Morse, I. A. Mdonld, R. Kotoor, nd M. D. Riding Inresed lithogeniity of bile on fsting in norml subjets. Am. J. Dig. Dis. 22: Folh, H., M. Lees, nd G. H. Slone Stnley A simple method for the isoltion nd purifition of totl lipids from niml tissue. J. Biol. hem. 226: Horeher, B. L., nd A. Kornberg The extintion oeffiients of the redued bnd ol pyridine nuleotides. J. Biol. hem. 175: Mdonld, I. A,,. N. Willims, id D. E. Mhony A rpid nonhromtogrphi r ilysis of individul bile ids in humn bile extrts. J, Theoret. Biol. 57: Willims,.N., I. A. Mdonld, nd H. Prk-Dinsoy Primry bile id kinetis in ptients with primry biliry irrhosis nd in norml subjets. lin. Invest. Med. 2: Mdonld, I. A.,. N. Willims, nd D. E. Mhony ~~-Hydroxysteroid dehydrogense from Eshrihi oli: preliminry studies. Biohim. Biophys. At. 309: Hselwood, E. S., nd G. A. D. Hselwood The speifiity of 7-hydroxysteroid dehydrogense from Esherihi oli. Biohem. J. 156: Mhony, D. E.,. E. Meier, I. A. Mdonld, nd L. V. Holdemn Bile slt degrdtion by non-fermenttive lostridi. App. Enuiron. Mirobiol. 34: Willims,. N., R. Ky, L. Bker, R. Hurwitz, nd J. R. Senior Progressive fmilil holestti irrhosis nd bile id metbo1ism.j. Ped&. 81: Plmer, R. H., nd M. G. Bolt Bile id sulftes. I. Synthesis of lithoholi id sulftes nd their identifition in humn bi1e.j. Lipid Res. 12: hristie, W. H. M., I. A. Mdonld, nd. N. Willims Non-hromtogrphi olorimetri ssy for totl turine-onjugted bile ids: pplition of mesurements of g1yine:turine rtio in bi1e.j. Lb. lin. Med. 85: Hfien-Sheid, J.. M., nd M. P.. Hetors An enzymi method for the determintion of the g1yine:turine rtio of onjugted bile ids in bile. lin. him. At. 65: Domingo, N., J. Ami, nd J. Huton Dosge utomtique des sels bilires onjugues de l bile pr l S-hydroxysteroide deshydrogense. lin. him. At. 37: Downloded from by guest, on August 22, 2018 Journl of Lipid Reserh Volume 21, 1980 Notes on Methodology 385
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