antinutrientes tanino

8/6/2019 antinutrientes tanino

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Overview of Soybean Processing and Products

Compositional Changes in T rypsin Inhibitors, Phytic Acid,Saponins and Isoflavones Related to Soybean Processing12ROBERT L. ANDERSON AND WALTER J. WOLFB iopolym er R esearch, N ation al C enter fo r A gricultural U tiliza tion R esea rch, A gricultura l R esearchService, U .S. D epartm ent of Agriculture, Peor-a, IL 61604

ABSTR ACT Soybeans are high in protein but alsoc on ta in a n umbe r o f m in or c on stitu en ts tra ditio na llyc on si de re d t o b e antin utritio na l fa cto rs . T he se in clu det rypsin inh ibi to rs , phyt ic ac id , sapon ins and sof lavones.T hese c om pound s are now th ought to have be neficialbiological effects in the diet, such as low ering bloodcho le ste ro l o r p re ventin g c an ce r. S oy be an p ro ce ss in gc ha ng es th e c on te nt o f t he se m in or c on stitu en ts in v ario us w ays . T his re view d is cu ss es th e chang es i n co nte nto f try psin in hib ito rs, p hy tic a cid , sa po nin s a nd so flav on es a s s oy be an s a re p ro ce ss ed in to th e con ventio na lp ro te in in gre di en ts , flo urs , c on centra te s a nd is ol ate s,as w ell as som e of the traditional Oriental soybeanfoods. J. N utr. 125: 581S-588S, 1995.IN DEXING KEY WORD S:s oy be an s ofla vo ne phy ti c a cidaponin rypsin inh ib it or

P rocessing of soybeans, w hether by traditional orWestern meth od s, is n ec essa ry to p ro du ce a nim al fee dingredients, food for hum an consum ption or functio na l p ro te in in gre die nts in te nd ed fo r in co rp ora tio ninto a w ide variety of hum an foods. D uring the courseo f so yb ean p ro ce ssin g to chang e p rope rtie s, th e c hemical com position m ay change as w ell. In this revieww e summarize the com positional changes that occuri n tryps in i nh ib ito rs , phy ta te , s apon in s and i so flavonesa s a re su lt o f p ro ce ssin g.Proteins

The content and properties of oil and protein areth e p rim ary d eterm in ants o f who le so yb ean v alu e. O ilan d p ro tein are sep ara ted from ea ch o th er e arly in mostWestern pro ce ssin g; in some trad itio na l O rien tal so yfo od s, o il an d p ro te in rem ain to ge th er wherea s in o thers they are separated. Soybean oil is not included inthis discuss ion.0022-3166 /95 $3 .00 1995 Ameri can Ins ti tu te o f Nutr it ion .

The proteins of soy contribute to the nutritionalvalue of foods and feeds and are responsible for anum ber of functional characteristics in a variety offo od s. H eatin g is n ece ssary to a tta in max imum nutritional value and to m odify functional properties ofsoybean pro te in .K akade et al. (1973), using immobilized trypsin toremov e try psin in hib ito rs from a raw so y flo ur ex trac tfo llowe d b y rat feed ing e xpe rim en ts, co nc lu ded th ata pp ro ximate ly 40% o f th e g row th -d ep re ssin g e ffe ct o fth e unh ea te d extra ct was due to th e try psin in hib ito rs.T he remain de r o f th e g row th d ep re ssio n was a ttrib ute dto p oor d ig estib ility of th e u nd en atu re d p ro tein.

Trypsin inhibitorsA lthough soybean protein products require heatprocessing to achieve m axim um nutritional value,p artly th ro ugh try psin in hib ito r d en atu ra tio n, try psinin hib itors a lso d isp la y a ntic arcin og en ic p ro perties(Me ssin a and Barn es 1991). T he p re dom in an t try psininhibitors in soybeans and derived m aterials are proteins and they are located, for the m ost part, w ith themain storage proteins in the protein bodies of thecotyledon (H orisberger et al. 1986, H orisberger andTacchini-V onlanthen 1983a, H orisberger and T ac-c hin i-Vonla nth en 1983b ). T his b ein g th e c ase , try psininhibitors tend to fractionate w ith the m ilieu of storage p ro te in s a s s oybeans a re p roce ss ed in to ingr ed ientsan d fo od s. T he re a re e xce ptio ns to this g en era lity th at1P re se nte d a t th e F irs t In te rn atio na l S ympo sium on th e R ole o fSoy in P re venti ng and T re atin g Ch ronic D is ea se , h eld i n Me sa , AZ ,F eb ru ary 2 0-2 3, 1 99 4. T he s ympo sium was s po nso re d b y P ro te inT echnol og ie s I nte rn atio na l, th e s oybe an g rower s fr om Neb ra sk a,In dia na a nd Iowa a nd th e U nite d S oy be an B oa rd . G ue st e dito rs fo rthis sym posium w ere M ark M essina, 1543 L incoln Street, PortT ow nsen d, WA 9 83 68 , an d Jo hn W . E rdman, Jr., D iv ision o f N ut ri ti ona l Sc iences, Un ive rs it y o f I ll ino is , U rbana , IL 61801-3852 .2 T he m en tion o f firm n am es o r trad e p rod ucts d oes n ot im plyth at th ey a re e nd ors ed o r re commen de d b y th e U .S . D ep artm en t o fAg ri cu ltu re ove r o th er f irms o r s im ila r p roducts not mentio ned.

581S


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582S SUPPLEMENTT ABL E 1

Tr y psi a i nhi bi tor con ten t of soybeans and pr ocessed soypro te in produc tsType Tryps in i nh ib it or ac ti v it y1

mg/g sam ple m g/g proteinW hole soybeansR awlour5Toastedflour5Concentrate6Isolate5'616.

7-27. 21 '328-327.9-9.45.4-7.31.2-30.034.7-122.63'457.815.98.4-11.21.4-29.4

1Measured by t ryps in i nh ib it ion .1 Hafez (1983).3V alu es, o rig in ally e xp re sse d as try p sin u nits in hib ite d, w e rec on v erte d to try p sin in hib ito r u nits w i th th e re latio nsh ip th at l p go f p ure try p sin h as an ac tiv ity o f 1 .9 try ps in u nits.4 Kakad e e t al. (1 972) .5R ac k is e t al. ( 1985 ).6 Peac e e t al. ( 1992 ).

w ill be discussed as they arise. R ack is et al. (1986)rev iew ed the literature through 1985 on protease inhibitor content of som e plant f oods.B ased on 19 v arieties and strains, w hole soy beansw ere reported to contain 17-27 m g of try psin inhib-ito r/g (Haf ez 1 98 3) ac co rd in g to ac tiv ity assay s w ithth e resu lts ex presse d as th ou gh all activ ity re sid ed inthe m ain species, the K unitz try psin inhibitor (T able1). S oy beans are approx im ately 40% protein and K ak ad e et al. (1 97 2), af ter an aly z in g 1 08 strain s an d c ul-tiv ars, reported they contain 35-123 m g try psin in-h ib ito r/g o f p ro te in . W hen so ybean s are p ro ce sse d in toraw defatted f lour, a process in w hich the hulls andoil are rem o ved, none of the try psin inhibitors are rem o ved but they becom e enriched in the f lour to lev elsof 28-32 m g/g of f lour, w hich equates to approx im ately 58 m g try psin inhibitor/g of protein (T able 1).T ry psin inhibitors, being proteins, are subject todenaturation and inactiv ation by heat. Heated orto aste d f lo urs are pro du ce d h av in g a ran ge o f try psinin hib ito r ac tiv itie s d ep endin g upon th eir in te nd ed u se .A f ully toasted soy f lour w ill hav e a try psin inhibitorlev el of only 8-9 m g/g of f lour or approx im ately 16mg /g o f p ro te in . Soy pro te in concentrat es are p roducedb y wash in g d ef atte d f lo urs w i th e ith er aqueou s e th anolo r ac id if ied wa te r. In thes e p roce ss es o ligos accharidesand other constituents are rem ov ed but m ost of theprotein is not; the protein content is therefore increased to >65% . T he ranges of try psin inhibitor activ ity are giv en in T able 1, 5-7 m g try psin inhibitor/g o f co nc en trate o r 8 -1 1 mg /g o f c on cen trate pro te in .S oy protein isolates are processed to contain >90%protein. D epending upon the am ount of w ashing ofthe precipitated curd as w ell as the try psin inhibitorc on te nt o f th e s tartin g s oyb ean s, iso late s c on tain try psin inhibitor lev els in the range of 1-30 m g/g or, be

cause nearly all of this product is protein, the sam erange per gram of protein (T able 1).O rie ntal and o th er so ybean f oods are g en erally lowin try psin in hib ito r (T ab le 2 ). S oy sauc e, p ro du ced b yen zym ic o r acid ic h yd ro ly sis o f a m ix tu re o f so yb ean sand w heat, is low in try psin inhibitor content at 0.3m g/g of sam ple or 3.3 m g/g of protein equiv alent. Itis unlik ely that these v alues represent activ ity f romthe protein inhibitors but the origin of the m easuredactiv ity is uncertain. M iso is a product m ade by ferm entation of soak ed and steam ed soy beans. T able 2show s a v alue of 4 m g/g of sam ple or 23 m g/g of prote in f or m iso . H ow e ve r, w h en lip id s are remo v ed f romm iso b y e xtractio n, th e try psin in hib ito r le vel f alls to4 m g/g of protein and it w ill decrease further if them i so is h eate d.T ofu, w hich is m ade from heated soy bean m ilk byco ag ulatio n o f the p ro te in s w ith a salt su ch as c alc iumsulf ate follow ed by cooling, has a try psin inhibitorcontent (9 m g/g of protein, T able 2) near to that asso ciated w ith a f ully to aste d so y f lo ur (1 6 mg /g o f p rotein, T able 1). S oy infant form ula is m ade f rom soyprotein isolate w ith the addition of other nutrients.T he try psin inhibitor lev el in these products f alls inthe range of 0.3-3 m g/g of sam ple or 2-16 m g/g ofp ro te in (T ab le 2 ).D iPie tro and L ie ne r (1 989) d if f ere ntiate d b etw e enthe K unitz and B ow m an-B irk inhibitor content ofso y bean f lo urs, c on centrate s, iso late s and a varie ty o ff oo ds (T ab le 3 ). T h e K u nitz so yb ean try psin in hib ito rpresent w as quantitated by rock et imm u noelectro-phore sis and the Bowm an-B i rk inhib ito r was measuredby chym otry psin inhibition. S oy f lours w ere f ound tocontain from 1.1 to 19.6 m g/g and f rom


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COM POS IT IONA L CHA NGES W ITH SOY BEA N PROCESS ING 583ST ABL E 3

Kunitz and Bowntaa-Bi rk trypsin inhibi tors insoy protein products and some foods1

Sample Kunitzinhibitor Bowman-Birkinhibitormg /g s amp le

FloursConcentratesIsolatesDehydratedsoymilkW heat-soypancake mix 1.1-19.6


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584S SUPPLEMENTmenting cook ed soy beans to produce tem p eh (S udar-m adji and M ark ak is 1977; S utardi and B uck le 1985).SaponinsMo st listin gs o f soy be an an tin utritio nal f acto rs in

the past included saponins, although w ith little or noju stif ic atio n. T o xicity w as attrib uted to th em simp lyby analogy w ith saponins f rom other sources that, ind eed, are to x ic . Howev e r, mo st re v iew ers h av e ig no re dstudies reported 25 y ears ago show ing that f eedingsoy bean saponins to chick s, rats and m ice failed toinhibit grow th ev en w hen fed at lev els three to f iv etim es those of a norm al soy bean m e al diet (Ishaay a etal. 1 969). Mo re re ce ntly , h y po chole ste ro lem ic and an -tic arc in og en ic e ff ec ts h av e b een attrib ute d to so ybeansapon in s (Me ssin a and Barn es 1991). C on sequ en tly ,there is justif ication f or rem o ving saponins f rom thelis t o f an tinutritional f ac to rs in s oybeans (L i ener 1981 ) .S oy bean sap on in s are comple x compo un ds co nsistin g o f n onpo lar trite rp enoid alc ohol ag ly c on es lin k edto one or m ore polar oligosaccharides resulting inmo lec ules w ith amp hip hilic p ro pertie s sim ilar to d ete rg en ts. E arly stu die s re su lte d in c on fu sio n abou t th enum ber and structures of the agly cones but it is nowb elie ved th at o nly th re e ag ly co ne s, so yasapo ge nol A ,B and E , o ccur in in tac t sapon in s. O th er so yasapog en -o ls re po rte d earlie r e v id en tly w e re artif ac ts o f h y drol y sis conditions (Pric e e t al. 1987) . Five ma jo r s apon in sh av e b een is olate d and s tru ctu rally c harac te riz ed (K i-tag aw a et al. 1 98 5a, K itag aw a et al. 1 98 5b , K itag aw aet al. 1988b). T he m ain com plex ity arises from the

s tructu re s o f th e attached o ligos accharides , wh ich maybe free or acety lated (K itagaw a et al. 1988a). A d ditional com plex ity has been reported recently in thef o rm o f 2 ,3 -d ihyd ro -2 ,5 -d ihyd roxy -6 -me thy l -4H-py ran-4-one attached to the C-22 hy drox yl group ofsoy asapogenol B ; this group is rem o ved w ith the f ormation o f malto l w h en th e sap on in s are h eate d (K u douet al. 1 99 3).T h is d iv e rsity o f stru ctu re and compo sitio n has alsom ade it dif ficult to analy ze f or soy bean saponins. Av ariety of m e thods hav e been reported but at presenth ig h p erf ormanc e liq uid c hromato graphy te chniq ue sare availab le f or analy sis o f th e in tac t sapon in s (K udouet al. 1993) as w ell as the agly cones obtained uponacid hy droly sis of the saponins (Ireland et al. 1986).T he latter m e thod assum e s that the ratio of agly coneto sugars is 1:1 and this is not alw ay s justif ied (Pricee t al. 19 86 ); h enc e, resu lts m ay n ot alw ay s agree w ithan aly sis of in tact sap on in s. A t ten tio n is also calle d tothe f act that som e of the early results obtained by thinlay er ch romatog rap hy (Fenw ick an d Oak en fu ll 1 98 1,Fenw ick and O ak enf ull 1983) gav e v alues that w erealmo st 1 0-f old to o h ig h. T h ese h ig h valu es appare ntlyresulted f rom im p urities and use of a nonspecif ic detectio n re ag en t (C url et al. 19 85 ). S tru ctural stu dies

TABL E 6Sa pon in con ten t of soybea ns a nd pr ocessed

so y p ro tein p ro du ctsProduct S apon in con te nt

Soybeans'Soybeans2Soybeans3Cotyledons4Hypocotyl-radicle4S e ed coat ( hu ll s]4Ful l- fat f l ou r, u nh eat ed2Ful l- fat f lo ur, h eat ed2Protein concentrate2Pro tein i so late2

g /1 00 g dry ma tte r0.22-0.330.530.09-0.320.21-0.271.67-1.9800.470.5300.81

1 K i tagaw a e t al. (1 98 4).2 I re lan d e t al . ( 19 86 |.3 S h iraiw a e t al. (1 99 1).4 T an iy am a et al. (1 98 8).

and problem s of analy sis are rev iew ed by Price et al.(1987).T able 6 show s saponin contents f or soy beans, seedparts and d eriv e d p ro te in p rodu cts. S o ybean s c on tain0 .1-0 .5% sap on in s; th e h ig h en d o f the rang e d ep en dson a v alue determ ined by analy sis of the sapogenols.T he coty ledons contain 0.2-0.3% saponins w hereasthe lev el in the hy pocoty l approaches 2% . H ow ev er,the hy pocoty l represents only approx im ately 2% ofth e see d; h en ce , it h as little e ff ec t on th e c omp ositio nof f lours and related products that m ay contain thisf raction. T he seed coat (hull) contains no saponins.U nh eated an d h eated f ull-f at f lo urs co ntain ap pro xim ate ly 0 .5% sap on in s; th e resu lts in dicate th at th e saponins are heat stable (ex cept f or such changes as reported by K udou et al. 1993). N o saponins w ere detected in a protein concentrate prepared by aqueousalcohol ex traction as w ould be ex pected based on thesolubility properties of the saponins. Isolates hav ebeen reported to contain 0.8% saponins. A lthoughw ater so lu ble , th e sapo nin s ap paren tly comple x w ithth e p ro te in s and h en ce are retain ed w ith th e p ro te in sduring the is ol ation proce ss .S ap on in co nten t of sev eral O rie ntal f oo ds (T ab le 7)such as soy m ilk , y uba, tofu and natto is in the rangeof 0.3-0.4% , about the sam e as in soy beans. Ok ara(th e in so lu ble resid ue remain in g af ter p re paration o fsoym ilk ), m iso (f erm e nted soy bean paste) and natto(ferm ented, cook ed soy beans) tend to be som ew hatlow er in sap on in co nten t at 0.1 -0 .3%.W ith the ex ception of alcohol-ex tracted concentrates, the saponins tend to rem ain w ith the proteinp ro du cts d eriv ed f rom so yb ean s. Fe rm e ntatio n, as inth e p rep aratio n o f m iso, resu lts in som e d eg rad atio nof the saponins and thus a low er saponin content asc ompared w i th so ybean s.


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COM POS IT ION AL CHA NGES W ITH SOY BEA N PROCESS IN G 585ST ABL E 7

Supon i n content of Or iental soybean foodsProduct S apon in con te nt

Soymi lk1Soymi lk2Y u ba (dried soy m ilk f ilm )2O k ara (resid ue f rom so ym ilk )2Tofu2Miso2Natto2

g/100 g dr y mat ter0.26-0.310.39

0 . 410.100.30-0.330.150.251 I relan d et al. (1 98 6).2 K itag aw a et al. (19 84 ).

IsoflavonesA l th ou gh lo ng c on sid ered to b e an tin utritio nal f ac

to rs, b ec au se o f th eir e stro ge nic pro pertie s so yb eaniso flav on es are n ow o f g re at in te re st b ecau se o f th eiran tic an cer ac tiv itie s (see ref eren ce s in C ow ard et al.1 99 3). S oy be an s co ntain tw o majo r iso flav one s, g en -istein an d daid ze in , an d a m i no r o ne, g ly cete in . In th eseed, the isof lav ones are present prim arily as /3-glu-cosides and a portion of the glucosides also is substituted on the C-6 hy drox yl of the glucose by a m alony lgro up , e sp ec ially in th e h yp oco ty l (K u do u et al. 1 99 1 ),w hich represents only approx im ately 2% of the seed.A c ety l deriv ativ es also hav e been reported (Farm a-k alidis and M urphy 1985; W ang and M urphy 1994a,W ang and M urphy 1994b) but these m ay be degradatio n p rodu cts re su ltin g f rom decarbox y latio n o f th emalo ny liso flav on es d urin g ex trac tio n an d w o rk up o fthe ex tracts (H orow itz and A s en 1989).T ab le 8 sh ow s low a nd h igh va lu es for isofla von econtents of soy bean v arieties reported by W ang and

Murphy (1 994b ); t he se v alu es range f rom 1200 to 4200Mg /g -Fo r additio nal in fo rma tio n on variatio ns o f isof lavones w i th s oybean varie ti es , c rop year and locationof grow th, see E ldridge and Kw olek (1983) and W angand M urphy (1994b). T he glucoside f orm s of the isof lav on e p re dom in ate . In th e v ariety Pio ne er 9 11 1, f orex am p le, 6"-O -m alony lgenistin accounts f or 42% ofth e to tal f ollow ed b y g en istin (2 1% ) an d 6 "-O -malo n-y l daid z in ( 16%). In con tras t, th e ag lycones ( geni ste in ,daidz ein and gly cetein) m ak e up only 2% of the totalisoflavones.S oy f lour, m ade by defatting dehulled f lak es andgrinding, has an is of lavone pro f ile approx ima ting thato f so y bean s. G ranule s and te x tu re d v ege tab le p ro te inp rod uc ts c on tain ap pre ciab le q uantitie s o f th e 6 "-O -acety l derivat iv e s o f gen is ti n and daid z in , p re sumab lybecause of heat treatm e nt during processing, w hichdecarboxy l ate s th e ma lony l g luco si de s.Pro te in i so lates contain reduced leve ls o f i so f lavones( 600-1000 Mg /g)as compared w i th s oybeans and f loursas a re su lt o f th e aq ueo us p ro cessin g u sed d urin g manuf acture. A concentrate m ade by aqueous alcohol extraction is v ery low in isof lav ones (73 M g /g) becauseth e iso flav on es are solu ble in aq ueo us alco ho l an d areth us larg ely remov ed d urin g p ro ce ssin g. A d ditio naldata on f lours , concentrate s and is olate s were reportedby E ldridge (1982), C ow ard et al. (1993) and Frank eet al. (1994), although these w ork ers did not reportv alu es f or th e ac ety late d o r ma lo ny late d d eriv ativ e s.Isof lav one contents of traditional O riental andW e stern soy bean foods are sum m ariz ed in T able 9.R o aste d so yb ean s are low in the malo ny l d eriv ativ esbut higher in the acety l form s as a result of the heattreatm ent. B ev erage products approx im ate the comp ositio n f or so yb ean s ex cep t f or red uce d lev els o f th emalo ny l d eriv ativ es. T o fu is g re atly red uce d in iso flav on es b ec au se o f th e aq ueo us p ro cessin g d urin g manufacture. T em peh is som ew hat low er in isof lav one

TA BLE 8I sofl avone content of soybeans and pr ocessed pr otei nroducts1*GlucosideProductVinton

8 1oybeansPioneer9111oybeansSoyflourSoygranuleTVPAProteinisolateProtein isolateProtein concentrateDin234637147727507tr88trGin32688840787063413730118Glin666041132146344931Din121690261106932018ndMalonylGin290175610231931

1 D ata f rom W ang and M urphy (1994a, 1994b).2 D in = daidz in; G in = genistin; G lin = gly cetin; D ein = daidz ein; G ein = genistein; G lein = gly cetein; tr = trace; nd = not detected.


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586S SUPPLEMENTT ABL E 9

I sof lavon e con ten t of tr adi ti on al Or ien tal an d Wester n soybean f oods' 1ClucosideProductRoasted

soybeansInstantbeverageInstant beverageTofuTempehBeanpastemiso|HonzukurimisoFermentedbeanurdSoyho togSoybaconTempehburgerTofuyogurtSoyParmesanCheddarcheeseCheddar

cheeseMozzarellacheeseFlatnoodleDin460444525252ml72ml35tr3642trtr167trGinM g/g551775745846596123tr672715880trml46336Glin6876758142118nd15141812nd121715ndMalon

159255ndndnd12tr256126nd671715GinMg/g63144259108164ndndnd425nd79trtr7637Glin

' Data from W ang and M urphy (1994a).2 D in = daidz in; G in = genistin,- G lin = gly cetin; D ein daidz ein; G ein = genistein; G lein = gly cetein; tr = trace; nd = not detected.

content than tof u and contains elev ated lev els of theag ly co ne s f orm e d b y e nz ymatic h yd roly sis d uring f erm entation. S im ilar trends are noted for bean paste(m iso) and the other f erm ented soy f oods.C ontent of isof lav ones in W estern-sty le soy f oodsf alls in to th e range o f 4 3 ig /go r c heddar c he ese -lik ep ro du ct to 3 86 ju g/g f or tempeh b urg er. T h e v alue s f orthese f oods are considerably low er than those of soybeans because soy is only one of sev eral ingredientsused, including fat and w ater. Cow ard et al. (1993)and Dw yer et al. (1994) also report analy ses f or O riental and W estern soy f oods.It is ap pare nt th at p ro cessin g ge nerally d oe s n ot remo v e th e iso flav on es f rom so yb ean p ro tein p ro du ctsand f oods, e x ce pt f or c on centrate s p re pare d b y alc ohole xtractio n. T he f orm may be altered b y h eat tre atm e ntand by enz ym e reactions during f erm entation but theiso flav on es remain . L ow erin g o f iso flav on e c on ten tsof som e soy bean foods also results from dilution bec au se o f th e ad dition o f o th er in gre dien ts, e .g ., salt inmiso.Conclus ionsA s is the case w ith m any of the foods w e consum etoday , soy bean processing is usef ul and necessary tod estro y o r remo v e u nd esirab le co nstitu en ts, m ak e n utrients m o re accessible or to im p rov e palatability .H ow ev er, processing tow ard these ends also leads tochanges in the com position of the v arious soy bean

m aterials com pared w ith w hole soy beans. T hesechanges m ay be intentional, as in the case of heatingto d im i nish try p sin in hib ito r ac tiv ity ; th e re su lt o f d iff eren tial solub il it ies, as when i so f lavones and saponinsare ex trac ted in to e thanol duri ng the wash ing requ iredto p ro du ce som e co nc en trate s; o r th ey may b e ef fec tedas a result of binding to the protein com ponentsthroughout processing, as appears to occur w ith saponins and phy tic acid. W ith the ex ception of thetry psin in hib ito rs, th e c omp ou nd s rev iew ed h ere g enerally are s tab le to p roce ss ing o f s oybeans as p rac tic edto day . It sh ou ld n ot th ere fo re b e dif ficu lt to main tainapprox im ately the naturally occurring lev els in theseed in man y p ro ce ssed p ro du cts if f utu re stu dies d ictate that these com p ounds are desirable in our diet.

L IT ER AT UR E C IT EDB eleia, A ., Ida, E. I. & L ethi, T . T . (1990) Phosphorus and phy ticacid distribution during soy m ilk processing. A rq. B iol. T ecnol.33 : 623-629 .B eleia, A ., T hu Thao, L . T . & Ida, E. I. (1993) L ow ering phy ticpho spho ru s b y h y drati on o f s oy b ean s. J. Food S c i. 5 8: 3 75 -377 ,388.Cow ard, L ., B arnes, N . C., S etchell, K . D. R . & B arnes, S . (1993)G en is te in , d aid z ei n, an d th eir /3 -g ly c os id e c on ju gat es : an tit umo ris of lav on es in s oy b ean f oo ds f rom Am e ric an an d A s ian d ie ts. J.A g rie . Fo od C hem . 4 1: 19 61 -1 96 7.Curl, C . L ., Price, K . R . & Fenw ick , G . R . (1985) T he quantitativ ees tim atio n o f sap on in in p ea (Pis um sativ um L .) a nd so ya (G ly cin ema x). F ood Chem. 1 8: 2 41-2 50 .


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COMPOS IT IONA L CHA NGES W ITH SOY BEA N PROCESS ING 587SDav ies, N . T . & R eid, H. (1979) A n evaluation of the phy tate,z inc , co pp er, iro n an d m an gan ese c onten ts o f, an d Z n av ailabilityf rom , s oy a- bas ed te x tu re d- ve ge tab le -p ro te in m e at- su bs tit ute s o rm eat-e xte nde rs. B r. J. N u tr. 41 : 57 9-5 89.D iPietro, C . M . & L iener, I. E . (1989) S oy bean protease inhibitorsin foods. J. Food S ci. 54: 606-609, 617.Doell, B . H ., Ebden, C. J. a S mith, C. A . (1981) T rypsin inhibitoractiv ity of conv entional foods w hich are pan of the B ritish dietand som e soy a products. Q ual. Plant. Plant Foods H um . N utr.3 1: 139 -150 .Dw yer, J. T ., Goldin, B . R ., S aul, N ., Gualtieri, L ., B arakat, S . &A dlercreutz , H. (1994) T ofu and soy drinks contain phy toes-trogens. J. A m . D iet. A s soc. 94: 739-743.Eldridge, A . C. (1982) Determ ination of isof lav ones in soybeanf lo urs, p rote in c on cen trate s, and iso late s. J. A g rie . Fo od C hem .30 : 353-355 .E ldridge, A . C . & Kw olek , W . F. (1983) S oy bean isof lav ones: ef fectof en viro nm e nt an d v ariety on co m po sitio n. J. A g rie. Foo d C hem .31 : 394-396 .Farm ak alidis, E. & M urphy , P. A . (1985) Isolation of 6"-O-ace-ty lgenistin and 6"-O -acety ldaidz in f rom toasted def atted soy -f lak es. J. A g rie. Food C hem . 33: 385-389.Fenw ick , D. E. & Oakenfull, D . (1981) Saponin content of soyabeans and som e com m ercial soy a bean products. J. S ci. FoodAg ri e. 3 2: 2 73 -2 78 .Fenw ick , D. E. a Oakenfull, D . (1983) Saponin content of foodp lan ts an d so m e p re pare d f oo ds. J. S ci. Fo od A g rie. 34 : 1 86 -1 91 .Frank e, A . A ., Custer, L . J ., Cerna, C. M . & N arala, K . K . (1994)Q uantitation of phy toestrogens in legum es by H PL C. J. A grie.Fo od C hem . 4 2: 19 05 -1 91 3.Hafez , Y . S . (1983) N utrient com position of dif f erent v arietiesand strains of soy bean. N utr. R ep. Int. 28: 1197-1206.H arland, B . F. & Oberleas, D. (1977) A m odif ied m ethod for phytate analy sis using an ion-ex change procedure: application totex ture d v eg etab le p ro tein s. C ere al C hem . 5 4: 8 27 -8 32 .Honig, D. H., W olf , W . J. & . R ack is, J. J. (1984) Phy tic acid andp hos ph oru s co nte nt o f v ario us s oy be an pro tein f rac tio ns. C ere alChem . 61:523 -526 .Hori sb erg er, M . , C le rc , M . -F. a Pah ud , J.-J. ( 19 86 ) U ltras tru ctu rallocaliz ation of gly cinin and /3-congly cinin in G ly cine m ax (soybean) cv . M aple A rrow by the im m unogold m ethod. H istochem -istry85:291-294.H orisberger, M . & T acchini-V o nlanthen, M . (1983a) U ltrastructu ral lo caliz atio n o f K un itz in hib ito r o n th in sec tio ns o f G ly cin ema x (so yb ea n) cv. Ma ple Ar ro w b y th e g old metho d. H isto ch em-i st ry 7 7: 3 7- 50 .H orisberger, M . & T acchini-V o nlanthen, M . ( 1983b) U ltrastructural localiz ation of B owm an-B irk inhibitor on thin sections of

G lycine ma x (soybea n) cv. Maple Ar row by the gold method.H is to ch em i st ry 7 7: 3 13 -3 21 .H orow itz , R . M . & sen, S . (1989) D ecarbox ylation and ex changere ac ti on s i n f lav o no id g ly c os id e malo nat es . P hy to ch em i stry (O x f )28:2531-2532.Ireland, P. A ., Dz iedz ic, S . Z . & K earsley , M . W . (1986) S aponincontent of soy a and som e com mercial soy a products by m eanso f h ig h-p erf orm an ce liq uid ch ro m ato grap hy of th e s ap og en in s.J. S ci. Fo od A g rie. 3 7: 6 94 -69 8.Ishaaya, I., B irk , Y ., B ondi, A . & Tencer, Y . (1969) Soybean sa-ponins IX . S tudies of their ef fect on birds, m am m als and coldb lo ode d o rg an is m s. J. S ci. Fo od A g rie. 2 0: 4 33 -4 36 .K ak ade, M . L ., Hof fa, D. E. & L iener, I. E. (1973) Contributionof try psin inhibitors to the deleterious ef fects of unheated soybeans f ed to rats. J. N utr. 103: 1772-1778.K ak ade, M . L ., S im ons, N . R ., L iener, I. E ., & L am bert, J. W . (1972)B io ch em ical an d n utritio nal asses sm e nt o f d if fe ren t v arietie s o fsoy beans. J. A g rie. Food C hem . 20: 87-90.K itagaw a, I., S aito, M ., T aniy am a, T . & Y oshik aw a, M . (1985a)S aponin and sapogenol. X X X V I II. S tructure of soy asaponin A 2 ,

a bisdesm oside of soy asapogenol A , f rom soy bean, the seeds ofG lycine ma x Mer rill. C hem. P ha rm. Bull. 33: 598-608.K itagaw a, I. S aito, M ., T aniyam a, T . & Y oshikaw a, M . (1985b)S aponin and sapogenol. X X X IX . S tructure of soy asaponin A 1 ; abisdesm oside of soy asapogenol A , f rom soy bean, the seeds ofGlycine max Merr ill. Chem. P ha r m. Bull. (Tokyo) 33: 1069-1076.K itagaw a, I., T aniy am a, T ., N agaham a, Y . , O kubo, K ., Y am auchi,F. & Y oshikaw a, M . |1988a) Saponin and sapogenol. X LII.S tructures of acety l-soy asponins A I , A 2 , and A 3 , astringent partially acety lated bisdesm osides of soy asapogenol A , f rom Am e rican soy bean, the seeds of G ly cine m ax M errill. C hem . Pharm .Bu ll . ( T ok y o) 3 6: 2 81 9-2 82 8.K itagaw a, I., W ang, H . K ., T aniy am a, T . & .Y o shik aw a, M . (1988b)S aponin and sapogenol. X L I. R einv estigation of the structureso f s oy as ap og en ols A , B , a nd E , o le an en e- sap og en ol s f rom s oy b ean ,structures of soyasponins I, II, and III. Chem . Pharm . B ull.( To k yo ) 3 6: 1 53 -1 61 .K itagaw a, I., Y oshikaw a, M ., Hay ashi, T . a T aniy am a, T . (1984)Q uantitativ e determ ination of soy asaponins in soy beans of v ario us o rigin s an d so yb ean p ro du cts b y m ean s o f h ig h p erf orm anc eliq uid c hro m atog raph y. Y ak ugak u Z assh i 1 04 : 2 75 -27 9.K udou, S ., Fleury , Y . , W e lti, D ., M agnolato, D ., U chida, T ., R ita-m ura, K . a Okubo, K . (1991) M alony l isof lav one glycosidesin soy bean seeds (G ly cine m ax M errill). A grie. B iol. C hem . 55:2227-2233.K udou, S ., T onom ura, M , T suk am oto, C., Uchida, T . S ak abe, T .,T am ur, N . &. Okubo, K . (1993) Isolation and structural eluc id at io n o f DDMP- co nj ug ate d s oy as ap on in s as g en uin e s ap on in sf ro m s oy bean se ed s. B ios ci. B io tec hn ol. B io ch em . 5 7: 5 46 -55 0.L ehrf eld, J. (1989) H igh-perf orm ance liquid chrom atographyan aly sis o f p hy tic ac id o n a pH -stab le, m acro po ro us p oly m er c olum n. C ereal C hem . 66: 510-515.L iener, I. E. (1981) Factors af fecting the nutritional quality ofsoy a products. J. A m . O il C hem . S oc. 58: 406-415.Lolas, G. M ., Palam idis, N . & M arkak is, P. (1976) T he phy ticac id -to tal p ho sp ho ru s re lati on sh ip i n b arl ey , o at s, s oy be an s, an dw h eat. C ereal C hem . 53 : 8 67-8 71 .M essina, M . a B arnes, S . (1991) The role of soy products in reducing risk of cancer. J. N ati. C ancer Inst. 83: 541-546.Om osaiy e, O. a Cheryan, M . (1979) Low -phy tate, full-fat soyprotein product by ultraf iltration of aqueous ex tracts of w holeso yb eans . C ere al C hem . 5 6: 5 8-6 2.O 'N eill, I.K ., S argent, M . & T rim ble, M . L . (1980) D eterm inationo f ph ytate in f oo ds b y p ho sp ho ru s-31 Fo urier tran sf orm n ucle arm ag netic res on an ce s pe ctro m etry . A n al. C hem . 5 2: 1 28 8-1 29 1.Peace, R . W ., S arw ar, G. & T ouchburn, S . P. (1992) T rypsin inhibitor lev els in soy -based inf ant f orm ulas and comm ercial soyp ro te in iso lates and co nce ntrate s. Fo od R es . In t. 2 5: 1 37 -1 41 .Prattley , C . A . & S tanley , D . W . (1982) Protein-phy tate interactions in soy beans. I. L ocaliz ation of phy tate in protein bodiesan d glo boid s. J. Fo od B io ch em . 6 : 2 43 -25 3.Price, K . R ., Curl, C . L . & Fenw ick , G. R . (1986) T he saponincontent and sapogenol com position of the seed of 13 v arietiesof legum e. J. S ci Food A g rie. 37: 1185-1191.Price, K . R ., Johnson, I. T . a Fenw ick , G . R . (1987) T he chem istryan d b io lo gic al s ig ni fic an ce o f s ap on in s i n f oo ds an d f ee din gs tu ff s.C rit. R ev . Food S ci. N utr. 26: 27-135.R aboy , V , Dick inson, D. B . a B elow , F. E. (1984) V ariation inseed total phosphorus, phy tic acid, z inc, calcium , m agnesium ,and protein am ong lines of Glycine m ax and G. soja. Crop S ci.24 : 431-434 .R ack is, J. J., Gum bm ann, M . R . a L iener, I. E . (1985) T he USDAtry p si n in hi bi to r s tu dy . I. B ac kg ro un d, o bje ct iv e s, an d p ro ce du raldetails. Q ual. Plant. Plant Foods H um . N utr. 35: 213-242.R ack is, J. J., W o lf , W . J. a B ak er, E.G . (1986) Protease inhibitorsin plant foods: content and inactiv ation. In: N utritional andT ox ico log ical S ign if ic an ce o f E nz y m e In hib ito rs in Fo ods (Friedm an, M ., d.),p. 299-347. Plenum Press, N ew Y ork , N Y .


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588S SUPPLEMENTR anhotra, G. S ., L oew e, R . J. & Puyat, L . V . (1974) Phy tic acidin soy and its hy droly sis during breadm ak ing. J. Food S ei. 39:1023-1025.S chaef er, M . J. & L ov e, J. (1992) R elationships betw een soy beancom ponents and tof u tex ture. J. Food Q ual. 15: 53-66.S chuster, E. M . & B odw ell, C . E. (1980) Phy tic acid content ofthirty -tw o comm ercial soy products. Fed. Proc. 39: 659 (abs.|.S hiraiw a, M ., Harada, K . &. O kubo, K . (1991) Com position andcontent of saponins in soy bean seed according to v ariety , culti

v ation y ear and m aturity . A g rie. B iol. C hem . 55: 323-331.S udarm adji, S . & M ark ak is, P. (1977) T he phy tate and phy taseof soy bean tem peh. J. S ci. Food A g rie. 28: 381-383.S utardi & B uck le, K . A . (1985) Phy tic acid changes in soy beansf erm ented by traditional inoculum and six strains of R hiz opuso li go sp or us . }. Ap pi . Ba ct er io l. 5 8: 5 39 -5 43 .

T aniy am a, T ., Y oshikaw a, M . & K itagaw a, I. (1988) S aponin andsapogenol. X L IV . S oy asaponin com position in soy beans of v arious origins and soy asaponin content in v arious organs of soybean. S tructure of soy asaponin V from soy bean hy pocoty l. Y a-k ugak uZ as sh i 1 08: 5 62 -5 71 .Thom pson, D . B . & Erdm an, J. W ., Jr. (1982) Phy tic acid determ ination in soy beans. J. Food S ci. 47: 513-517.v an der R iet, W . B ., W ight, A . W ., Cilliers, J. J. L . S . Datei, J. M .(1989) Food chem ical inv estigation of tof u and its by productok ara. Food C hem . 34: 193-202.W ang, H. S i M urphy , P. A . (1994a) Isof lav one content in comm ercial soy bean f oods. J. A g rie. Food C hem . 42: 1666-1673.W ang, H. & M urphy , P. A . (1994b) Isof lav one com position ofAm e ric an an d Jap an ese so yb ean s in Io w a: e ff ects o f v ariety , cro py ear, an d lo catio n. J. A g rie. Fo od C hem . 4 2: 16 74 -1 67 7.

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