Chemistry, Texture, and Flavor of Soy

397 Pages·2010·21.19 MB·English

by  Keith R. Cadwallader and Sam K. C. Chang (Eds.)

1 Chemistry, Texture, and Flavor of
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In Chemistry, Texture, and Flavor of Soy; Cadwallader, K., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2010.
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In Chemistry, Texture, and Flavor of Soy; Cadwallader, K., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2010.
1059
ACS SYMPOSIUM SERIES
Chemistry, Texture, and Flavor of
Soy
Keith R. Cadwallader, Editor
1
0 Department of Food Science and Human Nutrition,
0
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g 9.f University of Illinois
or05
pubs.acs.k-2010-1 DepaSrtmamentKof.CCe.reCalhaanndgF,oEoddiStocirences,
p://1/b
htt02 North Dakota State University
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ACSDivisionofAgriculturalandFoodChemistry
AmericanChemicalSociety,Washington,DC
In Chemistry, Texture, and Flavor of Soy; Cadwallader, K., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2010.
LibraryofCongressCataloging-in-PublicationData
Chemistry,texture,andflavorofsoy/[editedby]KeithR.Cadwallader,SamK.C.Chang;
1 sponsoredbytheACSDivisionofAgriculturalandFoodChemistry.
0
0 p.cm.-- (ACSsymposiumseries;1059)
w
g 9.f Includesbibliographicalreferencesandindex.
or05 ISBN978-0-8412-2561-9
pubs.acs.k-2010-1 4(1S..aFmSoooKydfo-ow-oA-dCnsa-h-liyCnsgois)n-gI-IrCIe.osAsnegmsr.ee2sris.ceaPsn.laCIn.htCepamrdoiwtceaainlllsSa-od-Cceiroe,ntKyg.erDeitshisveRiss..i,o31n.9o6Sf3oA-yIgbIr.eiCcaunhl-at-unCrgoa,lnSgaanrmedssFKeos.o.Cd.
p://1/b Chemistry.
htt02 TX558.S7C442010
2 | 0.1 664′.805655--dc22
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P
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In Chemistry, Texture, and Flavor of Soy; Cadwallader, K., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2010.
Foreword
The ACS Symposium Series was first published in 1974 to provide a
mechanism for publishing symposia quickly in book form. The purpose of
the series is to publish timely, comprehensive books developed from the ACS
sponsoredsymposiabasedoncurrentscientificresearch. Occasionally,booksare
1
0 developed from symposia sponsored by other organizations when the topic is of
0
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g 9.f keeninteresttothechemistryaudience.
or05
p://pubs.acs.1/bk-2010-1 fpoarpaepBrspermfoopareyriaabtgeereeaexnicdnlcguodtmeodpptruoebhbleiesnthsteiavrebfoococoukvs,etrthahegeepbaroonopdkof;sooerdtihnteatrebsrlemesotatfyocbtoheneateadnudtdesideisntocreepv.riSoeovwmieddee
htt02 comprehensiveness. When appropriate, overview or introductory chapters are
2 | 0.1 added. Draftsofchaptersarepeer-reviewedpriortofinalacceptanceorrejection,
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In Chemistry, Texture, and Flavor of Soy; Cadwallader, K., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2010.
Preface
For centuries soy has served as an important and inexpensive source of
highqualityproteinthroughouttheworld,especiallyinAsia. Soybeansarenow
cultivated in large scale in North and South America, where they are mainly
used for production of edible oil and animal feed. Part of the defatted soy meal
1
0 by-products are refined into functional ingredients for inclusion into various
0
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s.acs.010-1 in the Western countries in the last thirty-forty years. More recent discoveries
pubk-2 of a number of health benefits of soy have spurred a new wave of demand for
p://1/b soy foods, not only in Western countries, but also in those countries which
on June 23, 2012 | htt14, 2010 | doi: 10.102 tqaaprrluoaseapdoluisiDttlotiyaiocel,tlncsiopaumnnlirultrsayeit.nnriyctgthiooetinennscaturhdlemnemaovenleedodlnogdspiohociyeuan.alsgltcghcGhroaroupolwlnrweottnrhtmihgeoeisnistnitnotthgshaohetyaetblgmtperloiuabmbnsutaetlpeebrtsecoondomnuufstecruttisimtooitooynpn-tciiaamoolnnnpdntreaooueifvntdieisslniozgtoyhaf,etfiototfhhonooedosrisdees.
5.42 mber In particular, numerous flavor and textural challenges impact the quality and
3.3ce consumeracceptabilityofsoyfoods. Theseflavorandtexturepropertiesaswell
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1D as the nutritional and health-promoting attributes are mainly determined by the
y 89.eb): chemistry and functionality of the chemical components of soy. We hope that
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wnlon This book is a culmination of a symposium titled “Chemistry, Texture and
Doati Flavor of Soy”, which was sponsored by the Agricultural and Food Chemistry
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P Meeting in Philadelphia, PA, August 17-21, 2008. Leading national and
international academic, government and industrial researchers from several
countries have covered the following topics as they relate to the quality of soy
foodsandingredients:
• Chemistry of soy and soy components, including isolation and
characterizationofbioactivesandfunctionalingredients/compounds.
• Texture aspects of soy and soy ingredients, including processing,
characterizationandmeasurementbysensoryand/orinstrumentalmeans.
• Flavorchemistryandanalysis(sensoryandinstrumental)ofsoyandsoy
products/ingredients/components.
xi
In Chemistry, Texture, and Flavor of Soy; Cadwallader, K., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2010.
We are grateful to the authors for their contributions and express our
appreciationtothemanyreviewersfortheirvaluableinsightsandcritiquesofthe
chapters. Weacknowledgewithgreatappreciationthefinancialsupportfromthe
ACS Division of Agricultural and Food Chemistry, the Illinois Center for Soy
Foods(throughgenerousfundingfromtheIllinoisSoybeanAssociation)andthe
NorthDakotaSoybeanCouncil.
KeithR.Cadwallader
Professor
UniversityofIllinois
1 DepartmentofFoodScienceandHumanNutrition
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pr 1302W.PennsylvaniaAvenue,Urbana,IL61801
org 059. [email protected](e-mail)
s.acs.010-1
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n June 23, 2012 | http://4, 2010 | doi: 10.1021/b DISPNAareooCmprftaCehrsKtsD3mo.2areC2kn,.otDCtoaefhSpaCttna.etgre7e6aU4ln0ainvderFsiotoydSciences
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5.42 mber KFaorwgo.c,[email protected](e-mail)
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xii
In Chemistry, Texture, and Flavor of Soy; Cadwallader, K., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2010.
Chapter 1
Carbon-Centered Radicals in Soy Protein
Products
1 WilliamL.Boatright*,1andM.ShahJahan2
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org 059. 1Department of Animal and Food Sciences, University of Kentucky,
pubs.acs.k-2010-1 2DepartmentofPhysics*W,LUelnxbiionvaegtrt1os@inty,pKoopfY.Mu4ke0ym5.e4pd6huis,Memphis,TN38152
p://1/b
htt02
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n June 23, 204, 2010 | doi: pTTrhhoeedsuefcrlteesevr-earlansdgaiecrdealfarbocomount2te1.9n46t-×toof1100t1y04p-ttioicma4l.e1s0pgo×rwe1ad0tee1rr5etsdhpainnsosoyptheerprrgofrotaemoidn.
o1
42 er protein sources. The majority of these free radicals appear to
35.mb be formed after the soy protein product is manufactured, and
63.ece during storage of the ‘dry’ powder exposed to oxygen. The
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aded ate ( or cysteine that result in elevated levels of radicals. If the
Downloation D wstoatreerd-heyxdproasteeddtoprooxteyignesn,atrheesleuvbeslesqoufenratldyicadlrsiewdillangdradaugaalilny
blic increase back to levels that existed prior to hydration. Based
Pu onthepeakshape,g-valueandpowersaturationcharacteristics

obtained with electron paramagnetic resonance spectroscopy,
thefreeradicalsinsoyproteinarepredominatelycomprisedof
carbon-centeredradicals.
Free-radicalsinfoodproductshavebeenstudiedextensivelybecauseoftheir
contribution to deteriorative-type reactions; both in foods during storage and in
humans. Generally, free radicals in biological materials are very short-lived.
Oxygenradicalshavetypicalhalf-livesrangingfrom10-9secondsforahydroxyl
radical (OH•) to 7 seconds for a lipid peroxy radical (LOO•) (1). In solution,
the stability of alkyl radicals generally follow the order of tert-alkyl > sec-alkyl
> n-alkyl > methyl, with the methyl radical having a half-life of 0.2 × 10-3
©2010AmericanChemicalSociety
In Chemistry, Texture, and Flavor of Soy; Cadwallader, K., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2010.
seconds(2). Hydroxylradicalshavebeenshowntoreactwithproteinstoproduce
carbon-centered radicals. These carbon-centered radicals are short-lived in
solution and react with a variety of compounds to produce non-radicals species
includingprotein–proteincrosslinks(3),DNAadducts(4,5),DNAstrandscission
(6,7)andproteinstrandscission(8,9).
Thedirectdetectionandquantificationofcarbon-centeredradicalsinsolution
hasprovendifficultbecausetheirhalf-livesareinmicroseconds,andbecausethey
canreactwithoxygenatadiffusion-controlledratetoformsecondaryradicalsthat
areoxygen-centered. Spin-trapadductscanaidintheanalysesoftheseshortlived
radicals. Thespin-trapadductsofcarbon-radicalshadshorterhalf-lives(from3.1
to8.4min)thancorrespondingadductsformedfromhydroxyl-orsulfur-centered
radicals (10).
1 Certain purified proteins in the ‘dry’ state, exposed to ionizing irradiation,
0
0
h were found to act as free-radical traps (11, 12). Using electron paramagnetic
c
org 059. resonancespectroscopy(EPR),UchiyamaandUchiyama(13)foundthatpyrolysis
pubs.acs.k-2010-1 or(e1fs4up)lrtaoentdediinHn-rutihacnehgffooarnomddsao,titohinnecrlsouf(d1fin5reg)ei-‘drdaerdnyit’cifiaselosdy(agpcr=oent2eti.r0na0la3sn0ind-g2il.ne0td0i4svi9gi)dn.uaalLlienaemsaoinnydoporaotchtieedirsns,
http://021/b (g = 2.00412.0054) as being from carbon-radicals, based on the observations
2 | 0.1 of Pshezhetskii and others, and Henriksen and others (16, 17). Uchiyama and
11
n June 23, 204, 2010 | doi: sγrUeo-cipyrhoriparytdreaoidmatetiaitonhn(es1a3tomy)r,ppelLliepeosoertxhalyaengtvdeehnlaoadtoshefbeerfasercen(tei1e-v4rxia)tpydoa;icsneadrdlessHtpoiuneascontsiomgvyeealynpty)dr.optoeetiohNnfesortnsrteeh(aa1totm5f)heatnahdltel(sopeenxylarysomtulbyidnesieeiesdns,
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42 er exposedtoprocessingandstorageconditionstypicallyencounteredwithproteins
35.mb useforhumanfoods.
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aded ate (
Downloation D ISPsBaomaptrlieghatt1anmdWothpeorsw(e1r8()Fpigreusreen1teAd)a.nThEePRlarsgpeecsytrmummeotfriactaylppiecaaklc(ogm=m2e.0rc0i5a)l
blic wastypicalforradicalslocalizedonthecarbonsofaminoacids(16,17). Also,a
Pu plotofsignalamplitudevs. squarerootofthepowerrevealedthatthemicrowave

powerwasatnon-saturatinglevelsfortheprimaryradicalsignal(g=2.005)upto
slightlyabove4mW.OnlythecarbonradicalproducesanEPRspectrawiththese
characteristicsofpeakshape,g-valueandpowersaturationlevel.
For comparison, the EPR spectra of three other common food proteins
(casein,sodiumcaseinateandeggalbumin)alongwithasampleofrancidsoybean
oil(PV=16±0.0)arepresented(Figure1,B-E).Theleveloffree-radicalsinthe
‘dry’ (or powdered) protein samples were estimated using a standard curve of
powderedK CrO inK NbO preparedbythemethodofCageandothers(19)and
3 8 3 8
dilutedwithpowderedKCl. TheCr(V)spinconcentrationswerecalculatedfroma
standardcurveoftheESRsignalofFremy’ssalt(dipotassiumnitrosodisulfonate)
solutions at –196°C after double integration. The free-radical content of the
commercial sample was 14-times greater than that of similar radicals trapped in
sodiumcaseinate,29-timesgreaterthaneggalbumin,andabout100-timesgreater
4
In Chemistry, Texture, and Flavor of Soy; Cadwallader, K., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 2010.