BraccoU94_Effect of Triglyceride Structure

8/2/2019 BraccoU94_Effect of Triglyceride Structure

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rA IO HB .[ Ch em ic a l s p litting AB + C + OH Id en tifies fa tty ac ids InC I OH sn -I. s n -2 , sn -3

rAB . Panc rea t i c Ilpase Iden tifies fa tty ac id

L C In position sn -2

1AB Phosph o llp id de riv at ives

C

Phosph o llpases (A 2 -C )

Id en tifies fa t ty a c ids In p os itio n sn -I, s n -3

F IG I. S te reo sp ec ific an a ly s is o f tria cy lg lyce ro ls .

I 0 02 S A m I C liii Nutr 19 94 :60 (su pp l): 1 002S -9S . P rin te d in U SA. 1994 American Society for Clinical Nutrit ion

E ffe c t o f tr ig ly ce ride s tru c tu re on fa t abso rp tio n1 Um berto B racco

A BSTRA CT S tereo spec ific d istribu tion o f fa tty acids o ntriacy lg lycen o l stru ctu res in fluences the techno log ica l behav io ro f fa ts as w ell as the ir ab sorp tio n fate . L ong-cha in fa tty ac id s in ____________ex te rna l ( sn - I and sn -3 ) po sitions m ay im pair fa t ab sorp tio n andthere fo re th e ph ysio log ica l respo nse to d ie ta ry fa ts. L ow er d i-g es tib ility o f bov in e m ilk fa t com pared w ith tha t o f hum an m ilkis re la ted to the d iffe ren t pos ition o f pa lm itic ac id in bo th fa ts.S te reospec ific an alys is o f cocoa bu tte r and fa ts con ta in ing s tearicac id of the s tea ric -o le ic -stea ric ac id (SO S) typ e show ed tha t long -ch ain sa tu ra ted fa tty acids a re a lm o st ex clus ive ly presen t inn-I and sn -3 positions , w h ich cou ld exp la in the ir im pa ired abso rp -tion and there fo re the ir neu tra l e ffec t o n se rum lip id in hum ansd esp ite the ir sa tu ra tion an d ch ain leng th . T he tru e energy va lueo f th ese fa ts the re fo re needs to be verified in m ixed d ie ts .Am J C /in Nutr 1994 ;60(supp l) :1002S-9S .

K EY W O RD S T rig lycerides, s truc tu re , lo ng-cha in fatty ac -ids , abso rp tion , cocoa bu tte r

In t roduc t ion

L ip id d ig es tion is a p ro cess tha t in vo lves the d ispersion o f bu lkfa t g lobu les in to fine ly d iv ided partic les . It in vo lves enzym aticsp litting of n eu tra l an d po lar m o lecu les , it re lie s on th e ch em ica land configu ra tion al stru ctu re o f lip id subs tra tes , an d it is re la tedto the phys ical sta te and the ph ysicochem ica l b eh av io r o f lip id s,the ir hydro ly tic p rod uc ts , and the em ulsified system s in a chang -ing env ironm ent (pH , pK a) during the d igestion , abso rp tion , andtransport o f lip ids .

M any d ete rm inan ts a re the re fo re in vo lved in in tralum ina l fa td ig es tio n , the up take o f d iges ted fa t, and the m etab o lism of ab-so rbed lip id -d iges tio n produ cts . A ll th ese facto rs gov ern thep hysio lo g ica l respon se to d ie ta ry fa ts, w here any d istu rb an ce isre la ted to pa tho log ica l s itu a tion s, concern in g , fo r ex am p le , theetio logy of ca rd iovascu la r d iseases , obes ity , and in flamm ato ryd iso rders . T he sm all in tes tine , in W este rn adu lt popu la tions , isp resen ted w ith 120 - 15 0 g lip ids/d , w here exog en ous trig lycen-ides a re the m ain fa t com ponen ts; ex ogenous ch o leste ro l, endog -en ous cho leste ro l, ph osp ho lip ids, an d g lyco lip ids con tr ib u te anaverage of 10% of the lip ids p resen ted da ily . H e te ro geneous lip ids truc tu res (sa tu ra ted , m onoun sa tuna ted , an d po lyun sa tu ra ted fa ttyac ids ), p o la r lip ids (partia l g ly cen id es and pho sph o lip id s), g ly c-ero l, cho leste ro l, and phy tos teno ls a re p rocessed d aily ex trace l-lu la rly an d in trace llu lar ly , crea ting re lationsh ips am ong ing es tedlip ids, the ir transp ort an d m etab o lism , an d the ir p hys io lo g icals ign if icance .

E n zym atic ac tiv ity

In vivoD ig es tive enzym es , such as lingua l and pan crea tic lipase ,

and cofac to rs (eg , co lipase ) ac t p red om inan tly a t then- I an dsn -3 position este r bond s of trig lycerides: the fa tty acid es terlinkages of 2 -m onog ly cerides , ph osp ho lip ids, and cho les te ro leste rs a re res istan t. L in gua l lipase is spec ific fo r then- 3 ra the rthan th e sn - l position , w hereas the pancrea tic en zym es sp litbo th fa tty acid este r link ages. T h is m ean s th at the spec ificdis tr ibut ion of th e fa tty ac ids in the g lyceride m olecu le p laysa k ey ro le in lip id d iges tio n and abso rp tio n alon g w ith tphys ic a l sta te, the fa te o f the h ydro ly tic p rod uc ts , and the irp hase behav io r in w ate r.

In vitroBy m im ick ing the in v iv o en zym atic sp litting , an im al (p ig )

p an crea tic lip ase can b e used u nder w ell-co n tro lled con d ition sto d ef in e the s truc tu re o f na tu ra l trig lycerides ( I. By th is hy-dro ly t ic s p li ttin g , little o r no hyd ro lys is o f es ters o f seco ndaryh ydnoxy l g roups occurs . A s in som e vege tab le fa ts , sa tu ra tedfa tty ac ids o f the trig lycerides a re fo und a lm os t ex clus ive lyth e sn - I an d sn -3 positions . T h is re la tive ly sim ple m etho do l-ogy a llow s u s to confirm tha t in vege tab le fa ts then-2 pos i -t ion of the trig lycer id e m olecu le con ta ins a h igh propo rtio n o

Fr om the Nestl#{233}esea rch C en tre , L au sa nn e . S w itze r lan d .Pre sented at M eta bo lic C o as equ ea ce s o f S tea ric A c id R e la tiv e to

O th e r L aa g-C ha ia F a tr A c ids .A dd re ss re p r in t req ue sts to U B rac co . N es te c L td R esea rch Cen tre .

V e rs-c he z-le s-B la nc , P0 Bo x 44 . C H -l00 0 La usan ne 2 6 , Sw itz e rla nd .


2/8

C,- SI

c.1- S - SC C I

C

ci

C-S

C

-S

a

CC

-S

CC

-S

CC

30 35 4 0 4 5

. S D.

EFFECT OF TRIGL Y CERIDE STRUCTURE

F IG 2 . H P LC of black-curra nt-se ed oil with a la se r light-sca tte ring dete ctor. 0 . ole ic acid: L. linole ic acid; Ln. a -linole nic acid: yLn, y-linolenic a cid: P . pa lm itic acid: S . ste aric acid.

lOO3S

unsaturated (olei c, l i nolei c, and l i noleni c) fatty acids and thatthe external (sn-l and sn-3) posi ti ons are mainl y occupied bysaturated fatty acids (palm i tic and steari c) w hen present i n thefat (eg, cocoa butter).

Stereospeci f i c analysis of fats

The pancreati c l i pase technique does not di sti nguish be-tween sn- I and sn-3 and is theref ore appl i cable to f ats and oi lsw i th a restri cted number of f atty acids originating f rom sym-metri cal tri gl ycerides, eg, POP, SOS, and 000 (w here P. 0,and 5, are palm i ti c, olei c, and steanic acids, respecti vel y ), asin cocoa butter and B orneo tal l ow . A steneospeci f i c analysi sof a complex tri gl ycerol m ix ture (eg, m i l k fat) requi res a moresophisti cated procedure invol v ing the Gnignard reagent to spl i tthe tri gl ycer ide into digl ycenides, denivati zati on to phospho-l i pi ds, and spl i tti ng w ith speci f ic phosphol i pases and subse-quent treatment w i th pancreatic l i pase (2). The analy ti cal stepsfor the steneospeci f i c analysi s of complex tri gl ycerides in-volving chemical and speci f i c enzymati c reacti ons are sum-mari zed in Figure 1. Thus w e are able to def ine for each fatand oi l the fatty acids in then-2 posi ti on and the overal l

composi ti on of the tri gl yceride as w el l as total f atty acidcomposition.

Posi ti onal di stri buti on of fatty acids in tri acy lgl ycerol s can alsobe determ ined ei ther by high-resoluti on 3C nuclear-magneti c-resonance spectroscopy (3), on the basi s of the chemical shi f t oesteni f i ed fatty acids in al l three posi ti ons, and by HPL C of thediastereomenic deri vati ves (urethane) of parti al gl ycer ides (4).The posi ti onal di stributi on of fatty acids in tri acy lgl ycerol s andthe major tri acy lgly cerol s of fats and oi l s therefore can be cal-culated w i th good accuracy, w hich i s a major step in the under-standing of the role of tr igly ceride structures in absorpti on andmetabol i sm . The tri gl y ceride di stri buti on of black-currant-seedoi l (an oi l r ich in y -l inolenic acid) is show n in Figure 25) andthe major fatty acids and thei r posi ti ons in the tr iacy lgl ycerol areshown in Table 1 (6). The number of tri acy lgl ycenols in an oor fat depends on the number of fatty acids present: there arerelati vel y simple conf igurations, such as in cocoa butter and ol i veoi l (Table 2), and more complex structures, such as in humanand nonhuman mi l k fats. I n fact, bov ine and human mi l k fat eachcontain one of the most complex m ix tures of natural f atty acids(n 25), w hich could theoreti cal ly gi ve 15 625 di f f erent tnigl yc-erides (n3). This value includes opti cal i somers, so that the num-ben of species w ould be reduced (Table 3).

T ABLE IT niacylglycerol ste rospecific ana lysis of bla ck-curra nt-see d oilsit sn-2 sa-3 Average

1 6: 0 1 4 . 2 2 . 7 2 . 0 1 .0 4 .4 1 . 1 6 . 918 :0 4 .9 0 .7 1 .5 1 .7 0 1 .31 8 :1 12 .6 1 .4 14 .1 1 .1 5. 1 1 . 1 1 0 . 8l8 :2n-6 42 .7 1 .2 53 .1 0 .9 43 .8 1 .6 4 6 .718 :3n-6 4 .1 0 . 7 1 7 . 4 1 .7 25 .8 1 . 7 1 5 . 918 :4n-3 0 .7 0 .2 2 .6 0 .6 5 .6 0 .4 2 .9
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3/8

1004S BRACCO

F IG 3 . S im plifie d sche m e of e nz ym atic dige stion. R ,, R and R ,, fa tty acids: b.s.s.l. , b ile -sa lt-stim ula te dipase:D G s, d ig ly ce rid es .

T ABLE 2F atty acid and triglyceride com position of fa ts w ith lim ited num bers offa tty a cids

Component C ocoa butte r O live oil%

F atty acids1 6 :0 2 4 -2 7 7 .0 - 17 .018:0 3 2 -3 6 1 .5 -4 .01 8 : 1 3 3 - 3 7 6 3 . 0 - 8 3 . 01 8 :2 1 -3 13 .51 8 : 3 - .5

TriglyceridesOL O - 1 200 0 0. 5 52 .5OO P 2 -5 2 7 . 3OP P - 4. 5P O P 1 4-16 -P0 5 34- 42 -S O S 2 4-28 -50 0 3 -7 -

0 . ole ic a cid; L, linole ic acid: P . pa lm itic a cid; S . stea ric a cid.

T ABLE 3M ajor triglyce rides in hum a n m ilk lip ids

F rom re fere nce 6 .

Trisaturates18:0-16:0-14:018:0-16:0-16:018:0-16:0-18:0

Mo n o en es18:1-16:0-12:01 8 : 1 - 1 6 : 0 - 1 4 : 018:1-16:0-16:018:1-16:0-18:012:0-16:0-18:11:0-16:0-1:116:0-16:0-18:118:0-16:0-18:1

Di e n e sI 8 : 0 - 1 8 : 1 - I 8 : 118:1-16:0-18:1

T rie ne s and te trenesI 8: 1 - I 8 : 1 - I 8:118:1-18:2-18:2

T ri gl yceride structure and digesti bi l i tyT ri gl yceri de structure analy si s has tw o purposes: to determ ine

the fatty acid i n thesn-2 posi tion w i thout di scrim inati ng betw eenex ternal posi tions sn-l and sn-3 and to i denti f y each fatty aci don the tri gl ycerol molecule by a complete stereospeci f ic anal ysis.W i t h these methodologies, i n parti cul ar, the speci f i ci ty of pan-creatic l ipase, w e can exam ine the ef f ects of tr ig ly cer ide structureon l i pi d digestion, absorpti on, and metabol i sm . A simpl i f i edscheme of the enzymati c di gesti on of dietary f at (F i g 3) show sthat i n the stom ach sn-3 f atty aci ds are released by l ingual l i pase,w i th some speci f i ci ty of the enzyme for short- and medium -chaintrig ly cer ides (i e, m i l k f at). Fatty aci ds w i th 1 2 carbon atoms

r RjR2- L R 3

r Ri- R 21

10 H

have a PK a of 4.5 and are w ater soluble w hen protonated andioni zed. They are absorbed passi vely by the gastri c mucosa andenter the portal vein. L ong-chain f atty aci ds (> 12 carbon atoms)are l ess soluble and are total l y i oni zed only at a v ery high pHThey di f f use into f at droplets and parti al l y to the surf ace of thdroplets, and thei r behav ior i n aqueous systems i s pH - and tem -perature-dependent. A t i ncreasing pH and in the presence of otheramphiphi l es (bi l e, sal ts, monogl yceri des, and calci um ), l i paseand i ts protei n cofactor col i pase l i beratesn- I and sn-3 f atty aci dsin the upper smal l i ntesti ne, l eav i ng sn-2 monogl y ceri des for sub-sequent esteri f i cation w i thi n the enterocy tes and plasm a transport(Fig 3) (7).

r O H- R2- [

OH

die ta ry fa t lingua l llpase(stom ach)

R 3 R 3 iD cSshort, m edium ch aIn (C i2)(pK a-4.5)

protonatedlionlzed(w a te r s o lu b le )

undissociated

p a nc re atic lip a se(u p p er s m a ll in te stin e )

R I + R 3

protonated toionized formsp H- d e p e n d e n t

C arboxy lesteraseb .s .s .l. (h u m a n m ilk I

p assive d iffusion In fat glob uleportal vein g lob ule m em brane
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4/8

EFFEC T O F T R I G L Y CER I D E ST RUC T URE I 00 5S

0 . o le ic a c id ; S . s te a ric a c id . Fro m re fe re nc e 1 3 . S D.

TABLE 4Me lting (TM) a nd c rys ta lliz a tio n (To ) te m p e ra tu re s o f m a in lip idsd uring c o c o a butte r d ig e s tio n

TM Tc

#{176}CTrisa turated

5 5 5 7 3 5 5P P P 6 6 4 4P S P 6 8 4 7S P S 6 8 5 1

Di s a t u r a t e dP 0 5 3 8 20S O S 4 1 2 3

Diunsa t ura t edOOP 1 8. 2 - 4OOS 2 4 .0 -1

Dig lycerides5 5 - 7 7 5 7P P - 7 0 4 7SO - 5 4 -P 0 - 4 6 -

Monog ly c e r ide s2 -P 6 8 -2-S 74 -

F r ee f a t t y a c i d sP 70 -S 7 7 -

5 , s te a ric a c id ; P , pa lm itic a c id ; 0 . o le ic a c id . Ad a p te dro m re fe re nc e 7 .

Physical pr oper ties of lipids dur ing fat metabolismThe physi cal state of the f ree fatty aci ds spl i t f rom then-l

and sn-3 po sition s of the tr ig ly ceri des and thei r behav ior i n aque-ous sy stems w i th l ow to high pH values play a key rol e i n de-term ini ng thei r rate of absorpti on. Once hydrol ysi s begins andf atty aci ds are rel eased, a vari ety of f atty aci ds and tri -, di -, andmonogl yceri des are formed and thus are present dur ing fat me-tabol i sm . Each has speci f i c mel ti ng and crystal l i zati on charac-teri sti cs. For example, the digesti ve spl i tt i ng of cocoa butter tr i -g ly cer ides gi ves ri se to l ip id structures w i th speci f i c physi cal be-haviors (T able 4).

The absorption rate of a f atty aci d under physiol ogical condi -ti ons i s theref ore dependent on the mel ti ng transi tion temperature

TABLE 6F a tty a c id c o m po s itio n a nd po s itio n a l d is trib u tio n o f m a jo r fa tty a c id si n hum an a nd bo vin e m ilk

Hum a n m ilk fa t Bo v i n e m l k f a t

Fa tty a c id C o m po s itio n P e rc e n t s , , -2 C o m po s itio n P e rc e n tn- 2

%12 :014 : 016:018 : 018:11 8: 218:3

4. 77. 8

2 7. 39. 7

3 4. 59 . 51.5

36576 8

59

1 8-

2. 91 2 . 03 0. 71 1. 62 6. 0

1 . 80 . 9

516 94 3II1 61 8-

o f the chain, w hi ch al l ow s the fatty aci d ei ther to enter into m i -cel l es or to f orm , at the increasing pH of the gastroi ntesti nall umen (pH 5 . 5 - 7 . 5 ) , hydrated acid soaps that are i nsoluble inaqueous media (Fig 4) (8). Phase- tr ansition temper atur es ar e de-term ined by the number of carbons in the chain and the degreeo f saturati on. I t i s not surprisi ng, theref ore, that the posi ti onaldi str i buti on of f atty aci ds and thei r phy si cochem ical behav iorm ay inf l uence the absorpti on of f ats, the uptake into the mucosa,the nesynthesi s i nto chy lom icrons, and the subsequent hepatic-l i pase spl i tt ing of l i poprotei ns.

L ong-chain satur ated fatty acids and fat absor ptionStearic acid structures

A s earl y as 1890 A rnschink (9) f ound tri steari n to be only 9-14% digesti bl e i n dogs. M atti l and H iggins (10) l ater reportedlow er digesti bi l i ty f or rats f ed syntheti c tr i gl yceri des contain ingstear ic and olei c aci ds, w i th a better uti l i zati on of steari c aci dw hen fed as m ixed tri gl ycer ides (550) than w hen f ed as tri steari nand tri o lei n physi cal m i xes (555 and 000). M ore recentl y , Jonese t a l (1 1 ), using oral l y adm ini stered stable-isotope-l abeled fattyaci d substrates, f ound that absorption ef f ici ency for [ 3C ] steari caci d i s 78% compared w i th 98-99.9% for olei c andino leic acids.

T he metabol i sm of single stereospeci f ic tr i acy l gl ycenol s w herestear ic aci d occupies ei ther then-2 on the sn-3 posi ti on of thediol ey l -tr iacy l gl ycenol w as investigated by Redgrave et al ( 12).

TABLESAbs o rptio n o f d ie ta ry fa t a n d c o m po n e n t a c ids

D i e t

000 050 500 0 5 5 S O SCa lc ium -m a g n e s ium s uffic ie n t (%)

To ta l 9 9 .4 0 .1 2 9 8 . 7 0 . 2 8 1 . 9 0 . 6 7 1 . 3 1 .3 5 6 .5 1 .2S t ea ra t e - 9 7 . 8 0 .4 5 5 .0 1 . 6 5 9 . 1 2 . 0 3 7 . 0 1 . 7O le a te 9 9 .4 0 .1 9 9 .7 0 .1 9 6 .7 0 .2 9 6 .8 0 .2 9 7 .0 0. 4

C a lc ium -m a g n e s ium d e fic ie n t (%)T o t a l 9 9 . 5 0 . 1 9 9 . 5 0 . 2 9 8 . 6 0 . 1 7 0 . 9 1 .8 7 9 .3 1 . 5St e a r a t e - 9 9 . 2 0 . 2 9 6 . 4 0 .3 6 0 .1 2 . 4 7 0 . 5 2 . 0O le a te 9 9 .5 0 . 1 9 9 . 9 9 9 . 8 9 3 . 5 0 . 8 9 7 . 1 0 . 2
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5/8

Meltedj

p H

Intestinall u m e n

S t o m a c h

r Cs t h l s ]A cid -s o a p c r y s ta l sS oa p c r y st a lsA q u e o u s

F a tty acid crysta lsA cid -s o ap c r y s t a lsA q u e o u s

Fatty a cid c ry sta lsA q u e o u s

f 7 IonizedC a r b o x y l a t e dG r o u p s (C O O )

III0

I II I L a m e l l a r l M i c e l l a r,! ,p A q u e o u s

lid Oi lp/p I dII

/p /p/O ilI A q u e o u s

P r o t o n a t e d l i d C a r b o x y lG r o u p s (C O O H )

TM T

l ( )06S BRACCO

F IG 4 . P hysica l sta te of long-cha in fa tty a cids (c-1 6 ) as a function of pH and te m pera ture . Adapted from re fe r-e nce 8 .

The reco very rate for the s,i-3 fatty ac ids at the chy lom icron lev elvarie s according to the ir chain leng th, be ing 90% for18carbon atoms and, re spec tiv ely , 2 0%, 8%, and 2% for c -20 , c-22 , and c -24 fatty ac ids. S truc tures such as OOS or 05 0 (asym -metrical and symmetrical) also influence the fatty ac id compo-sition o fchy lom icnon trig lycerides: more s tearic ac id w as presentin the OSO than in the 0 05 chy lom icrons . W ith the same syn-thetic s truc tural trig lycerides, M attson ( 1 3 ) reported that the ab-so rbability o f the various trig lycerides o f s tearic and o leic ac idin rats w as influenced by bo th the pos itio n occupied by s tearicac id in the trig lyceride mo lecule and by the die tary amount o fthe tw o divalent cations , as show n in Table.

Thus, in stearic ac id-rich s truc tures, to tal fat absorption isadverse ly affec ted by the to tal long -chain saturated fatty ac ids

pre sent a nd corre la te s direc tly w ith the ir co ncentration in then-2 position o f the trig lycerides .Bovine and human mi /k fats

The improved absorption o f human m ilk fat o ver bov ine m ilkfat is explained by structural differences be tw een fats . ATomarell i e t al (14 ), B reckeridge and Kuks is (15 ), and I (16 )repo rted, the co ncentration o f palm itic acid (16 :0 ) is re lativ elysim ila r in both fa ts. but human m ilk fat co ntains a higher pro -po rtio n o f palm itic ac id in thea-2 position (T able 6). L ard hasa sim ila r tota l am ount of pa lm itic a cid a nd conta ins 80 %f itin the sn-2 pos ition, w hich explains its high absorption rate . Thea b s o r p t i o n o f indiv idual fatty ac ids in different fat m ix tures isgene ra lly re la te d to the ove ra ll absorption o f the fat, but some

T ABLE 7F atty acid com position of the triglycerides (T G ) and the 2 -m onoglyce rides (2 -M G ) of diffe re nt oil sam ple s

F atty acid

B u t t e r

T G 2 -M G TG

C o c o a b u t te r

2- MG

Oh

TG

y e oil

2 -M G T G

S oybea n oil

2 - MG%

C a proic (6 :0 ) 1 .6 0 .3 - - - - - -C a prylic (8 :0 ) 0.7 0 . 7 - - - - - -C a pric ( 1 0 :0 ) 2 . I 3 .0 - - - - - -Lauric ( 12 :0 ) 2 .7 4 .2 - - - - - -M yristic ( 14 :0 ) 1 0 .9 1 8 .6 - - - - - -P alm itic (l6 :t)) 2 9 .2 3 4 .6 2 5 .6 1 .7 10 .1 3 .1 9 .9 2. 6S te aric (1 8 :0 ) 1 4 .6 8 .3 3 5 .1 1 .9 2 .8 0 .8 3 .6 0 .5O le ic (1 8 :1 ) 2 9 .5 2 1 .2 3 5 .4 88 .9 80 .9 8 8 .9 2 5 .0 2 6 .6Linole ic (1 8 :2 ) 1 .9 1 .2 2 .9 6 .8 5 .7 6 .6 53 .6 64.6Linolenic (18 :3 ) 1 .2 1. 7 0.4 2 .2 0 .6 0 .8 9 .3 1 0 .8O thers 6 .8 7 .9 1 .0 0 .7 0 .5 0 .6 1 .0 1 .2
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6/8

EFFECT OF TRIGLY CERIDE STRUCTURE lOO7STAB LE 8Pe rcen tag e o f ea ch ia in fa tty ac id in thesi i-2 p os itio n o f th etr ig lycer ide

Fa tty a c id Bu tte r C ocoa bu tte r O live o il S oybe an o il(7 ,

Lau r ic ( I 2 : t) )Myr is t ic ( 1-1 :0 )Pa lm i t i c ( 1 6: 0)S tea ric ( I 8 :0 )Oleic ( l8: l)L inoleic (18:2)Linolenic ( l8:3)

5 I . 856 .839 .51 8 . 9 523 .952. 1

38 .7

-

-

2. 2I .8

83 .778 .123 .3

-

-

10 .29. 5

36 .638 .640 .0

-

-

8. 74. 6

35 .540 .224 .1

fa tty ac ids de v ia te from th is g en e ra l tre nd , su ch as p a lm it ic ac idi n l a r d .

The absorption of saturated fatty acids depends on their posi-tion: th e low absorption of stearic acid in the fat mixtures weexamined is explained by its low proportion in then- 2 positionof the triglyceride. Randomizing milk fat by a conventional in-dustnial process results in shif ting pant of the palmitic acid fromth e in te rn al position to the external positions of the triglyceride.Chnistophe et al ( I 7) studied the effect of this modification onth e cholesterolemic behavior of butter in men and found thatrandomization may lower its cholestenolemic effect.

Fat str uctur e and dige stibilityFrom the above-reported studies, we conclude that saturated

triglycerides and structured triglycerides with external positionsestenified w ith long-chain saturated fatty acids show impairedabsorption rates. H ashim and Babayan ( I 8) report lower absorp-tion compared with corn oil of synthetic triglycerides in humanswhen glycerol is esterified w ith stearic and palmitic acids. N a-bisco (19. 20) filed patents covering the production of reduced-energy triglycerides derived from glycerol esterified w ith satu-rated long-chain fatty acids in then-I and sn-3 positions andshort-chain fatty acids in then-2 position. T riglyceride mixturesca n be modulated, for example: LSS, SLS, LLS, LSL , and LLL ,

TAB LE 9

where L and S are. respectively. long- and short-chain fatty acids.T he ratio of S(4:0) to L ( I 8 :0) and the position of L in the glycerolmolecule ofT en a range of energy availability. For example, ath e ratio of S to L is increased from 0.9 to I .2 to I .9, availableenergy increases from 16.7 to 18.4 to 19.7 kJ/g (4.0 to 4.4 to 4.7kcal/g). respectively. Procter & Gamble (21 ) also claim to haveproduced a reduced-energy fat in which long-chain saturatedfatty acids, in particular behenic acid, are combined with me-dium-chain triglycerides in structured lipids.

T ypical natural fats and oils with long-chain saturated fattyacids in the sn- I and sn-3 positions of tniacylglycenol are cocoabutter, Borneo tallow , shea butter, and sal (all with a high con-centration of steanic acid) : peanut oil, in which fatty acids 20:0to 24 :0 rep resen t 15% ofthe fatty acid in the, i -3 position (22) :and milk fat, in which 65% of the total palmitic acid esterifiesthe sn- I and sn-3 positions of the triglycerides.Th e of c o a a butter

The study on the effect of whole-food diets high in steanic acidon serum lipids in free-living subjects done at the PennsylvaniaState University (23) gave us the opportunity to do parallel struc-tural determination of fats by the technique already mentioned( I ). Table 7 reports the comparative data in percentage of eachfatty acid determined in the total triglyceride and the 2-mono-glyceride fractions. T able 8 shows the percentage of each fattyacid in the sn-2 position calculated according to the formula

(M /T X 3) X l( )0where M is the fatty acid in the s,z-2 position and T is totatriglycerides. For cocoa butter the molecular weight of the fattyacids varies in a very narrow range (from 256.4 for palmitic acidto 284.5 for stearic acid) and the molar quantities are similarmass percentages, whereas for milk fat (which contains short-and medium-chain fatty acids) the proportional dif ferences arelarger (T able 9).

T he unique composition and structure of cocoa butter, being monounsatunated fat w ith almost all monounsaturation in thesn-2 position and only two saturated chains esterified in the ex-ternal primary alcohol groups, gives this fat particular physico-chemical and metabolic characteristics. T he physical behavior i

Mo la r fa tty a c id com po s ition o f trig lyc e rid es (TG ) a ndn- 2 m onog lyce rid es (2 -M G ) com pare d w ith th e m a ss pe rce n ta ge sB u tt e r fa t C o coa b u tte r

TG 2-M G T G 2-M G

Fa tty ac id C om po s ition M ass C om po s it ion M ass C om po s it ion M ass C om po s it ion M assitiol c/ r % b vt F m ) ! % % by si tria l % % b y ,c t , , io l 3 % by

6 :0 4 .4 2 .1 1 .1 0 .5 - - - -8 :0 2 .0 1 .1 2 .2 1 .3 - - - -

1 0 : 0 3 . 8 2 . 6 5 . 0 3 . 5 - - - -12 :0 4 .0 3 .2 5 .8 4 .7 - - - -1 4 : 0 1 2 . 4 11 .3 20 .7 1 9 .1 - - - -16 :0 2 9 .0 29 .6 34 .0 35 .3 2 3 .75 25 .6 1 .5 5 1 .71 8 : 0 1 3 . 1 1 4 . 9 7 . 6 8 . 8 3 6 .15 35 .1 1 .9 0 1 .91 8 :1 2 6 .5 29 .9 1 8 .9 21 .7 3 6 .15 35 .4 8 9 .0 8 88 .918 :2 2 .1 2 .3 1 .5 1 .8 2 .9 0 2 .9 6 .7 6 6 .818 :3 - - - - 1 . 0 1 . 0 0 . 7 0 . 7

Ot h e r s 2 . 7 3 . 6 3 . 2 3 . 3 - - - -
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7/8

9 08 07 0

uooi ness anaF la vo ur R e le a se4

2 0

1 0

5, sa tura te d (pa lm itic a nd ste aric) fa tty acid; 0 . ole ic acid; Ln, lin-ole ic acid.

lO( )8S BRACCOchemical and metabol i c characteri sti cs. T he phy si cal behav ior i ssim i l ar to that of a pu re t ri gl ycer id e : monotropi c polymorphi ccrystal l i zati on and a short mel ting range are typi cal of w el l -de-f i ned tri gl ycer ides. Compared w i th beef tal low , w hi ch has sim i l aramounts of steani c acid that are more random ly di str i buted (T able10), cocoa butter show s a unique mel ti ng behav ior (Fi g), wh ichexplains i ts technologi cal perf ormance.

T he high concentrati on of steari c aci d and i ts speci f i c di stni -buti on on the tri gl y ceri de of cocoa butter , w hi ch makes i t d i f f er -ent f rom other natural edibl e f ats and oi l s, may explai n i ts re-ported neutral ef f ect on plasma l ip ids through i ts l ow er absorb-abi l i ty . A nimal ex periments w i th rats (24,5) , rabbi ts (26), andmonkeys (27) and human studies (28-30) conf i rm that cocoabutter has a neutral ef f ect on plasma total cholesterol concentra-ti ons and no platel et-cl otti ng ef f ect i n humans (3 1. Could thei rphysio logi cal behav ior be related to the low er digesti bi l i ty ofstearic acid i n cocoa butter? Experiments i n animals (32, 33) andhumans (34) seem to indi cate a low er digesti bi l i ty of cocoa but-ten, but better m ethods f or measuri ng the digesti on and absorpti onof total di etary l i pi ds is needed. T hi s need is also indi cated bythe di f f erent chem ical species and phy si cal states of f ecal f at (Fi g4) i n heal thy humans, w hi ch incl ude protonated f atty aci ds, soapsof di valent i ons, nonsaponi f i abl e matter, and thei r potenti al eu-tecti c m ix tures w i th the other f atty aci ds i n the diet35).

Conclusions

Stereospecificity i n terms of enzymatic di gesti on, l i pi d trans-port, and structure of natural oi ls and fats pl ays an essenti al ro lei n l i pi d metabol ism and therefore i n physiol ogical response. T hi si s parti cul arl y cri t i cal f or f ats and oi l s contai ni ng relati vel y highconcentrati ons of saturated long-chain f atty aci ds, w here low hy-drophilic and high mel ting characteri sti cs impai r thei r absorpti on.T hus, f ats contai ni ng sim i lar concentrati ons of palm i ti c and ste-ari c aci ds, such as human and bov ine m i l k f ats, have di f f erentabsorbabi l i ty because of the di f f erent locati on of f atty aci ds i nthe tri gl yceri de (14).

H uman inf ants w ere al so found to absorb 88% of the stearicacid w hen fed lard but onl y 40% w hen fed random ized lard (36).Rearrangement of f atty aci ds by random izati on may also explainthe low er cholesterol em ic ef f ect of random ized butter vs naturalbutter (7) and the low er atherogenic ef f ect of random ized peanut

T ABLE 1 0C om pa ra tive triglyceride distribution of fa ts w ith high conce ntra tionsof ste aric acid: cocoa butte r from diffe rent growing are as and ta llow

C ocoa butte r

T riglyce ride Braz il G ha na M a laysia T a llow%

55 5 1 .0 1 .4 2 .3 5 -7S O S 63 .7 76 .8 84 .0 2 9 -3 255 0 0 .5 0 .4 0 .5 3 4 -4 4S LnS 8 .9 6 .9 6 .8 5 -75 0 0 1 7 .9 8 .4 5 .1 10- 13000 8.0 6.1 1.3 5- 9

6 0z:; o00C/ )

30

0

- -Iow

cocoa buffer

-

-

-

4 Hardness : Waxiness

4 H e a t R esi stance

0 10 2 0 30 4 0T e m p e r a t u r e (#{176}C)

F IG 5 . S olid fa t a t diffe re nt tem pe ra ture s: m e lting behavior of fa ts astem pe ra ture increa se s from 0 to 4 0 # {1 76 }C .

oil vs natura l peanut oi l (37) . Sim i l arl y , the noncholesterol em icef f ect of cocoa butter can be rel ated to i ts composi ti on and struc-tural conf i guration and f i nal l y to i ts absorpti on.

T here i s sti l l considerable controversy about the degree of ste-ari c aci d absorpti on that must be inf l uenced by the rate of emul -si f i cati on i n the upper i ntesti ne and the presence of parti al g ly c-er ides acti ng as emulsi f iers enhancing m icel l i zati on. L ow er steari c aci d absorbabi l i ty could mean a low er energy value for cocoabutter. T he unansw ered questi on concerns how fats high in saturated fatty aci ds (> 1 8 carbon atoms) i n ex ternal tr i gl yceri deposi ti ons behave in f atty aci d m ix tures (eg, f rom lard) i n tupper smal l i ntesti ne. A

ReferencesI . Inte rna tiona l U nion of P ure and Applie d C he m istry. D e term ina tion

of fa tty a cids in the 2 -position in the triglyce ride s of oils and fa ts-m ethod 2 .21 0 . In : Paquot C , H a u t fe n n e A , e d s . S t a n d a r d m e t h o d sfor the ana lysis of oils, fa ts and deriva tive s. 7 th ed. O xford, U K:Blackwe ll S cientific P ublica tions, 1 98 7 : 1 1 1 -5 .

2 . M yhe r J J , K u k s is A . S tere ospe cific ana lysis of triacylglycerols viara ce m ic phosphatidylcholines and phospholipase C . C an J Bioche m1979: 7 : 117 - 24 .
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EFFECT OF TRIGLY CERID E STRUCTURE l OO9 S3 . C is to la DP . S m a ll DM. Ha m ilto n JA . Io n iz a tio n b e h a vio r o f a qu e o us

s ho rt-c h a in c a rbo xylic a c ids : a c a rbo n -1 3 NMR s tu dy . J Lip id R e s1 982 : 2 3 : 7 9 5 - 9 .

4 . C hris tie WW , N ic o lo va -D a m ya n o va B . La a ks a P . He rs l# {2 4 6 }fB . S te r-e o s pe c ific a n a ly s is o f tria c y l-s n -g ly c e ro ls v ia re s o lu tio n o f d ia s te r-e o m e ric d ia c y lg lyc e ro l d e riva tive s b y HP LC o n s ilic a . J Am O ilCh e m S oc 1 9 9 1 :6 8 :6 9 5 -7 0 1 .

5 . P e rrin JP . P re v o t A. Tra itle r H , B ra c c o U . Ana lys is o f trig lyc e rid es pe c ie s o f b la c k c u rra nt s e e d o il by HP LC via a la s e r h ig h s c a tte rin gde te c to r. R e v Fr C o rp s G ra s 9 8 7 :3 4 :2 2 1 -3 .

6. Je n s e n RG . Lip ids in hum a n m ilk. C o m po s itio n a nd fa t s o lub le v ita -m in s . In : Le b e n tha l E , e d . Te xtbo o k o f g a s tro e n te ro lo g y a nd nutri-tio n in in fa nc y . N e w Yo rk: R a ve n P re s s Ltd . 1 9 8 9 :1 5 7 -2 0 8 .

7 . S m a ll DM. The e ffe c t o f g ly c e ride s tru c ture o n a bs o rp tio n a nd m e -ta b o lis m . Annu R e v N utr 1 9 9 1 :1 1 :4 1 3 -3 4 .

8 . S m a ll DM. P h ys ic a l pro pe rtie s o f fa tty a c ids a n d the ir e xtra c e llu la ra nd in tra c e llu la r d is trib u tio n . In : B ra c c o U . D e c ke lba um R . P o ly-u ns a tu ra te d fa tty a c ids in hum a n nu tritio n . N e w Yo rk: R a ve n P re s s ,1 9 9 2 :2 5 - 3 9 .

9 . Arn s c h ink L. In te s tina l a bs o rp tio n o f d iffe re n t fa ts . (Ve rs u c h e Ub e rd ie R e s o rp tio n Ve rs c h ie d e n e r Fe tte a us d e m D a rm Ka na le ) . Z B io l1 8 9 0 :2 6 :4 3 4 -4 0 (in G e rm a n) .

I 0 . Ma ttil KF . H ig g in s JW . Th e re la tio n s h ip o f g lyc e rid e s truc ture to fa td ig e s tib ility . S ynth e tic g ly c e ride s o f s te a ric a nd o le ic a c id s . Ind E ngCh e m 1 9 4 5 : 2 9: 2 55 - 6 0 .

I 1 . Jo n e s P JH . P e n c ha rz P B , C la nd in in MT. Abs o rp tio n o fC- labelleds te a ric . o le ic , a n d lino le ic a c ids in hum a ns : a p p lic a tio n to bre a thte s ts . J La b C lin Me d l9 8 5 ;1 0 5 :6 4 7 -5 2 .

I 2 . R e dg ra v e TG , Ko da li DR . S m a ll DM. Th e e ffe c t o f tria c y l-s n -g ly c -e ro l s tru c tu re o n th e m e ta b o lis m o f c hy lom ic ro n s a nd tria c y lg ly-c e ro l-ric h -e m uls io ns in the ra t. J B io l C he m 1 9 8 8 ;2 6 3 :5 l 1 8 -2 3 .

I 3 . Ma tts o n FH . Th e a b s o rba b ility o f s te a ric a c id wh e n fe d a s a s in g leo f m ixe d trig ly c e ride . J N utr 1 9 5 9 :6 9 :3 3 8 -4 2 .

14 . To m a re lli RM, Me ye r B J, W e a b e r JR . B e nnh a rt FW . E ffe c t o f po -s itio n a l d is tribu tio n o n the a bs o rp tio n o f th e fa tty a c ids o f hum a nm ilk a nd in fa n t fo rm u la s . J Nu tr l9 6 9 ;9 5 :5 8 3 -9 0 .

1 5 . B re c ke ridg e WC , Kuks is A . Mo le c u la r w e ig h t d is tribu tio n o f m ilkfa t trig ly c e rid e s fro m s e v e n s pe c ie s . J Lip id R e s 1 9 6 7 :8 :4 7 3 -8 .

1 6 . B ra c c o U . Hum a n m ilk lip id s a nd p ro b le m s re la te d to the ir re p la c e -m e nt. In : G a lli C , P e c ile A , e ds . D ie ta ry lip id s a nd po s tn a ta l d e v e l-o pm e n t. N e w Yo rk: R a v e n P re s s , 1 9 7 3 :2 3 -4 0 .

1 7 . C hn is to p he A , Ma tthy s F , G e e rs R , Ve rdo nk G . Nu tritio n a l s tud ie sw ith ra nd om is e d butte r. C ho le s te ro le m ic e ffe c ts o f bu tte r-o il a n dra nd om is e d butte r-o il in m a n . Arc hm t P hys io l B io c h im1978;83:413-5 .

18. Ha s h im S A, Ba ba ya n VK. S tu d ie s in m a n o f pa rtia lly a bs o rb e d d i-e ta ry fa ts . Am J C lin N utr l9 7 8 ;3 1 (s u pp l):5 2 7 3 -6 .

19. N a b is c o B ra nd s , In c . R e du c e d c a lo rie trig lyc e ride s in fo o ds . P a rs ip -pa ny , N J: N a b is c o , 1 9 9 0 . (pu b lic a tio n WO 9 1 /0 3 9 4 4 -1 8 .0 9 .)

20 . Na bis c o B ra nd s , Inc . R e duc e d c a lo rie trig ly c e ride m ixture s .P a rs ipp a ny , N J : N a b is c o , 1 9 9 1 . (p ub lic a tio n WO 9 2 //bb S ,6 . 1 2 . )

2 1 . P ro c te r & G am ble C o . R e duc e d c a lo rie fa ts m a d e fro m trig ly c e ride sc o n ta in ing m e d ium a nd lo ng c h a in fa tty a c ids . C in c in na ti: P ro c te r& Gamb le . 1 9 8 9 . (p ub lic a tio n E ur. P t. 0 3 2 2 0 2 7 . 8 8 .0 6 .)

2 2 . S e m po re G . B e z a rd J . Q ua lita tiv e a n d qua ntita tive a n a ly s is o f pe a nuto il tria c y lg lyc e ro ls by re ve rs e d ph a s e liq u id c h ro m a to g ra phy .C hro m a to g r 1 9 8 6 ;3 6 6 :2 6 l -8 2 .

2 3 . Kris -E the rto n P M. D e rr J , Mitc he ll DC , e t a l. The ro le o f fa tty a c ids a tura tio n o n p la s m a lip id s . lipo pro te in s , a n d a po lipo pro te in s : I. E f-fe c ts o f wh o le fo o d d ie ts h ig h in c o c o a bu tte r, o live o il, s o yb e a n o il.da iry bu tte r, a nd m ilk c h o c o la te o n th e p la s m a lip ids o f yo un g m e n .Me ta b o lis m 1 9 93 :4 2:1 21 -9 .

24 . Kritc h e v s ky D . Te ppe r S A, B is e s G . Klurfe ld DM. In flue nc e o f c o -c o a butte r o n c h o le s te ro l m e ta bo lis m in ra ts : c o m pa ris o n w ith c o rno il, c o c o n ut a n d pa lm ke rn e l o il. N utr R e s 1 9 8 2 ;3 :2 2 9 -3 6 .

2 5 . Mura ka m i C , Ch im i K, Kam e m a ta u H, N iiya. Hira i C . E ffe c t o fpro c e s s e d o ils a nd fa ts o n c h o le s te ro l m e ta bo lis m iii. C om pa ris o no f th e e ffe c ts o f pa lm o il. ha rde ne d s o ybe a n o il a nd c a c a o butte r.Yu k a g a k u I 99 1 ; 4 0 : 7 I 9- 24 .

2 6 . Kritc he vs ky D . Te ppe r S A. B is e s G . Klurfe ld DM. Expe rim e nta la th e ro s c le ro s is in ra b b its fe d c ho le s te ro l fre e d ie t. P a rt 1 0 . C o c o abu tte r a nd p a lm o il. Ath e ro s c le ro s is 1 9 8 2 :4 1 :2 7 9 -8 4 .

2 7 . Fra s e r R , D ub ie n L, Mu s il F , Fo s s lie n E , W is s le r RW . Tra ns p o rt oc ho le s te ro l in tho ra c ic d uc t lym ph a nd s e rum o f rh e s us m o nke y fe dc ho le s te ro l w ith va rio us fo o d fa ts . A th e ro s c le ro s is 1 9 7 2 :1 6 :2 0 3 -1 6 .

28 . Co nn o r WE , W itia k DT, S to ne DB , Arm s tro ng ML. Cho le s te ro lba la n c e a nd fe c a l n e u tra l s te ro id a nd b ile a c id e xc re tio n in n o rm a lm e n fe d d ie ta ry fa ts o f d iffe re n t fa tty a c id c om po s itio n . J C he mI n vest 1 96 9:4 8: 13 63 -7 S.

29. D e nke MA, G rund y S M. E ffe c t o f fa ts h ig h in s te a ric a c id o n lip ida nd lip o p ro te in c o nc e n tra tio n s in m e n . Am J C lin N ut1 9 9 1 : 4 : 1 03 6- 4 0 .

3 0 . G ra nde F , And e rs o n JT, Ke ys A . C om pa ris o n o f e ffe c ts o f p a lm itica n d s te a ric a c id s in th e d ie t o n s e rum c h o le s te ro l in m a n . Am J C linNutr l9 7 0 ;2 3 :l 1 8 4 -9 3 .

3 1 . Stearic a c id ha s no p la te le t c lo tting e ffe c t: P e nn S ta te s tudy . Fo o dCh e m N e w s 1 9 9 2 N o v 5 :2 1 -2 .

3 2 . Apg a r JL, S h ive ly CA. Ta rka S M. D ig e s tib ility o f c o c o a butte r a n dc o rn o il a nd the ir in flue nc e o n fa tty a c ids d is tribu tio n in ra ts . J N utr1 98 7; I 1 7: 6 60 - S .

3 3 . C h e n IS , S u bra m a nia m 5 , Va hdun y G V, C a s s idyM, Ike da I.Kritc he vs ky D . A c o m pa ris o n o f the d ig e s tio n a nd a bs o rp tio n o fc o c o a butte r a n d pa lm ke rn e l o il a n d the ir e ffe c ts o n c ho le s te ro la bs o rp tio n in ra ts . J N utr 1 9 8 9 ;I 1 9 :1 5 6 9 -7 3 .

3 4. Mitc he ll DC, Ma cMa ho n KE , S h iv e ly CA, Apg a r JL, Kris -E the rto nPM . D ig e s t ib ility o f c o c o a butte r a nd c o rn o il in hum a n s ub je c ts : ap re lim in a ry s tu dy . Am J C lin Nu tr l9 8 9 ;S 0 :9 8 3 -6 .

35 . Ca re y MC , S m a ll DM, B lis s CM. Lip id d ig e s tio n a nd a bs o rp tio n .Annu R e v P h ys io l 1 9 8 3 ;4 5 :6 5 l -7 7 .

3 6 . F ile r U , Ma tts o n FF1 , Fom o n S J . Trig lyc e ride c o n fig ura tio n a nd fa ta bs o rp tio n b y the hum a n in fa n t. J Nu tr l9 6 9 ;9 9 :2 9 3 -8 .

3 7 . Kritc he vs ky D , Te ppe r S A, Ve s s e lino vitc h D , W is s le r RW . Cho le s -terol ve h ic le in e xp e rim e nta l a the ro s c le ro s is . 1 3 . R a nd om is e d pe a nu to il. A the ro s c le ro s is I 9 7 3 ; 1 7 :2 2 5 -4 3 .
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BraccoU94_Effect of Triglyceride Structure

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