Reexamination U a S .S . 95/003 ,7?
`
`Declaration Of Dr. Chang Lee
`
`Atterney Becket N 9. NE: PN—0031’00BS 313653—20} S (ARRIVE-32174}
`
`E’A'E‘EEN'E"
`
`EN THEE: UNE'E‘EB S'i‘A’E‘ES PA’E‘EN'E' AME) 'E‘RABEMARK {EFF} CE
`
`in Re Patent of:
`
`SAMPALIS, Fetini
`
`Cnntirniatien N0;
`
`i897
`
`Ceiitrni N0;
`
`95/00 i 9774
`
`Gretin Art Unit:
`
`3991
`
`Filed:
`
`FOR:
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`October i9, 20} i
`
`Examiner:
`
`CAi‘t/iPiELi..., Bruce R.
`
`ENTER PARTES REEXAM 0?? U3. PATENT 8,030,348: NATURAL MARINE
`SQURCE E’HQSE’HGLEPEBS CGMFRESENG EEGLYEJNSATURATED FA'E‘TY
`
`ACEEFS AN E) ’i‘iiEER AE’E’LECATEQNS
`
`Maii Step Deeiaratinn
`Commissioner for Patents
`
`P0. Bax i450
`
`Aiexandria, V1- 223 13— i 450
`
`BECLARA'E‘EON OF CHQNG Mo LEE E’HiD‘ UNBER 37 CFR.
`
`
`
`
`
`L, Chang M. Lee, declare as feiiews:
`
`l.
`
`1 ant a tenured Pr‘ritessrii' Emeritus at the University of Rhode isianrt in the Department 0f
`
`Nutritien and Feed Sciences.
`
`1 have been at the University ef Rhode isiand since '1980 and
`
`have been a full tenured professor since 1988. Prior to that, it was an Assistant Professor at
`
`Drexe} University from i975 to 1980.
`
`g\)
`
`i earned a Phi) in Fond Chemistry frein the University ethode island in 1974 and, a MS.
`
`in Food 'i"eehnniegy from the University Of Geergia in 1970. My pest-tinetnrai work was
`
`undertaken at the University at Genrgia under Dr. Rnniee Toiede and tbcnsed on Feed,
`
`Science and Technology.
`
`3‘
`
`i have actively researched in the field (if marine feed science for over forty years.
`
`i have
`
`published 100 journai artieiesi the vast majority being peer—reviewed, 2t} beak chapters, and,
`
`1
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`000001
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`Petition for Inter Partes Review
`Of U.S. Patent 8,278,351
`Emmi
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`ENZYMOTEC - 1079
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`Reexamination U . S .S . 95/00 l ,774
`
`Declaration of Dr. Chong Lee
`
`one ‘ooolc All of these publications are related to marine sciences. One of my often cited
`
`publications is directly on point in the present matter, as it is directed to solvent extraction of
`
`lipids from marine sources.‘
`
`l served as a member of the Advisory Committee on Codex Code of Surimi Manufacturing
`
`Practice (FDA Office of Seafood) from 1994-2000 and was a member of the NFl Surimi
`
`Advisory Committee (19924996),
`
`the NMFS Policy Adviser
`
`for Surimi
`
`industry
`
`Development (l992—l996),
`
`the AFTOMeFee Award Committee (Chair, $98} and the
`
`KSEA Councilor for Group E (19964999).
`
`1 am also a member of the American Chemical
`
`Society (Agriculture and Food, Chemistry) as well as a past member of the institute of Food,
`
`'l'eclinologists (_Seafood 'l‘eclinol. Group-"Executive Committee (NBS-W993), American Oil
`
`Chemists Society (Protein and Co—Froducts Section —Executive Committee (l989—l99l))i
`
`and the Northeast institute of Food Technologists (Chairman, l995i).
`
`l am currently on the
`
`editorial board of the Journal oquuatic Food Product Technology and previously served in
`
`this capacity for Scanning i’lil'ti'roscopy In{emotional—Hind Structure.
`
`l was a recipient of the
`
`Earl l). McFee Award in l993. an international award that recognizes distinguished research
`
`in seafood, science and technology
`
`My Curriculum Vitae is attached as Appendix A.
`
`in December of 20l l,
`
`l was engaged by counsel
`
`for Neptune Technologies and
`
`Bioressources, inc. (“Neptune”) to review issued Patent 8,030,348 (“the ‘348 patent”) and its
`
`substantive prosecution papers,
`
`the Corrected Request
`
`for Reexamination (USSN.
`
`95/‘09l.7l4) tiled liy AKCT Biomarine (“Alter”), including the Declarations of Mr. Bjorn Ole
`
`l—laugsgjerd and Dr. Thomas Gundersern and supporting materials.
`
`l was asked to provide
`
`my expert scientific opinion regarding the use of heat in solvent removah as gathered from
`
`my nearly four decades in marine research.
`
`£11
`
`6.
`
`l have had no prior direct involvement with either Neptune or Alter:
`
`i am being compensated
`
`at my customary hourly rate for my time spent on developing forming, and expressing the
`
`at, “A Simple Rapid Solvent (CHCl3~l‘\/le0ll) Extraction Method for Determination of Total Lipids in
`: See Lee
`Fish 'l‘issue,” AOA Clarezr'nai’i 79(2):487-92 (1996). attached Appendix B.
`
`2
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`Reexamination U . S .S . 95/00 l ,774
`
`Declaration of Dr. Chong Lee
`
`facts and opinions in this declaration.
`
`l have no personal interest in the ultimate outcome of
`
`the reexamination proceedings involving the ‘348 patent.
`
`8.
`
`l have carefully read the inlorniation provided and also conducted my own search of
`
`relevant, peer-reviewed scientific literature. My expert scientific opinion follows.
`
`eientlsts Commonl Heated Total Ll rid Extracts to Remove Extraction Solvents at the
`
`
`
`
`l ime attire Beaudoin Ailieattons.
`
`S '
`
`9. Generally, solvents, including chloroform, methanol, hexane, acetone, carbon tetrachloride,
`
`petroleum ether, and ethanol, may he used in lipid extraction. To remove these solvents, it
`
`was common, at the time of the Beaudoin experiments,
`
`to use rotary evaporation under
`
`reduced pressure with a bath temperature in the range of 40430002 When a hot plate was
`
`used for heating, without vacuum, the temperature used generally ranged from till—80°C or
`
`higher,3
`
`ll). in the case where solvents contain water, the solvents must he removed together with the
`
`water. For example, when extraction with waterumiscihle acetone is undertaken, the acetone
`
`has to he removed together with the water at an elevated temperature which is higher than the
`
`boiling point of acetone or water at atmospheric pressure (226., ahout 56.2%: or lOGOC). For
`
`the case of extraction with water—miscible ethanol, a positive azeotrope forms, in which the
`
`boiling, point
`
`temperature of the 'waterwethanol azeotrope is less than the boiling point
`
`temperatures of any of its constituents.
`
`in this case, the boiling point of ethanol is reduced
`
`from about 78.595 (in the unlikely case that pure ethanol
`
`is used) to about 78.295.
`
`Nevertheless, one would have to exceed the azeotrope boiling point at atmospheric pressure
`
`(27.6., about 782°C) to remove both ethanol and moisture.
`
`4 See Radio NS. 1981. “Extraction of tissue lipids with
`Appendix C.
`
`solvent of low toxicity.” Methods in Enzymologv ’72: 5—7.
`
`See Lee CM, ’l‘revino B. and Chaiyawat, lvl. W96. “A simple rapid solvent <(ji‘ihjl3-lVl€()H) extraction method for
`determination of total lipids in fish tissue.” ,1: A 0.4 C Im‘. 79(2):487'-492, Appendix B; 'l'olasa S, Lee CM, and Calhi
`S. 2011. “Lipid oxidation and omega~3 fatty acid retention in salmon and mackerel nuggets during frozen storage” J.
`Aquatic Food Product Technoi. 20(2): 1723482, Appendix E).
`
`3
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`Reexamination U a S .S . 95/00 l ,774
`
`Declaration of Dr. Chong Lee
`
`ll. Accordingly, it was a common practice,“ particularly when seeking to isolate total lipids from
`
`a marine source“, to heat samples to drive off
`
`solvents and, moisture in order to quantitate
`
`the amount of lipids recovered in fact, l personally engaged in this practice around, the time
`
`of Beaudoin: See page 488 of Lee et ai. (Appendix B) (noting that l heated the total lipid
`
`extract on a hot plate to remove solvent)
`
`
`Beandoln Heated the Lliitl Extracts in His international Fatent A.lleation
`
`12. My review of the Beaudoin references shows that he was focused on improving upon the
`
`total lipid extraction of Folcli4 and, accordingly heated his fractions to high temperature to
`
`rentove all solvents and moisture.
`
`13.1111 Beaudoin’s international Application {WQ 00/023546} all oilncontaining extracts were
`
`subjected to rotary evaporation followed by heating for 15 minutes at 125°C to remove
`
`remaining solvents and water. W0 00/023546 page l0? states (underlining at ded): “Table l3
`
`shows also that fraction 1
`is corn irised of l0.€)0/E! of volatile matter and, hurnidit ' after
`
`evaporation of the solvent. For the sarne test, the fraction ll gives a value of 6.8%. To get
`
`rid of traces of solvents it is int ortant to hrlel’lv heat
`
`
`
`to ationt 125%? for about l5
`
`
`
`min the oil under nitroen.”
`
`
`
`
`14, Accordingly, Beaudoin analyzed his acetone extract (traction l) and his ethanol extraction
`
`samples (fraction ll) and noted that they contained high percentages of “volatile matter and
`
`moisture” (WQ (lo/023546, Table l3). As Beaudoin’s objective was to irnprove upon the
`
`Folch method, a total lipid extraction method that he characterizes as “not commercially
`
`feasible because of the toxicity of the solvents involved,” Beaudoin attempted to remove
`
`solvents, including even trace solvents (W0 (Ell/(323546, page 3.33 This is consistent with the
`
`fact that it was conventional to heat total lipid preparations.
`
`4 'l‘liis refers to the classical chloroform/methanol lipid extraction protocol described in Finch at all “A Simple
`l/lethod for the Isolation and Purification of Total Lipids from Animal Tissues”
`Emir Chem. 2260}: 497—09
`(1957)
`
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`Reexamination U . S .S . 95/00 l ,7?
`
`Declaration of Dr. Chong Lee
`
`lSXl‘he disclosure of the two Beaudoin references (WE) 00/233546 and CA 2,25l,265) is
`
`consistent with the disclosure of other patents. For example, in US. Patent 7,572,464, to
`
`Chandler, a patent which cites to Beatidoin’s Wt) Oil/23546, states:
`
`
`“The extraction of essential fattv acids such as the ool‘mnsaturated fattv acids ETA and EPA
`
`from raw material sources has been
`out routinel
`hv sini
`solvent extraction
`
`
`
`solvent. Alternatively. strpercritical carbon
`of
`followed lav eva oration and recover
`dioxide has been used
`a solvent eg. US. Pat. No. 6,083,536. The disadvantage of the
`former method is that heat must he used to evaporate the considerable Quantities of
`solvent used and this leads to (leeradation of the active E’UFA content.” Column 2, lines
`13—22.
`
`
`
`and
`
`“One of the main advantages of the invention Lie, the content of US. Patent 7,572,464]
`that the extraction and filtration process can he operated at, or below, ambient temperature to
`1.
`ensure the best yield of active PUFAS. There
`no need to evaporate large volumes of
`solvent from the extracted all using heat." Colurnn 3. lines 34—38..
`
`Further, in later patents issued, to Beandoin, he states that he used heat to remove solvents.
`
`in
`
`US. Patent 6,§2l,768 to Beaudoin, concerning a “Process for the Extraction ofLipids From
`
`Fatty Bird ’l‘issrtes” {Fl led l l/QQ/letll ), Beandoin states:
`
`“EXAMPLE 3 ln this example, freshly ground lipid containing tissue from Peking duck was
`
`'rnrnersed in l/S of their weight ofdi
`' led water at a temperature or" 65°C and gently agitated
`for 30 minutes While maintaining the temperature constant. Fat was then separated from the
`
`solid and aqueous base
`centrifuge. ‘ '
`'
`’
`°
`’
`1c yiv e or rpm us intrastate
`
`
`tri licale.” Column 3, lines
`
`
`
`
`gravimetry was 50.6%. The experiment was carried out
`
`Also, in US. Patent ti,7l3,I-‘l£l7 to Beautloin, concerning a “Method, for Purifying Marine
`
`Mammal {)il Enriched in Omega 3 Fatty Acids and Compositions Cornpri sing Same” (Filed
`
`l0/G7/2002), Beaucloin states:
`
`
`
`
`
`'sic of traces of organic solvents anti volatile material. it“To ret ride. id fractions were
`
`heated to 125° C for about 15 minutes under inert atmosphere.” Column 10, lines 65~6'7.
`
`
`Beantlolnls Heaths
`in His Canadian A lieation 'Wonltl Be lnsnfficlent
`to Remove
`
`Solvents ant} Moisture.
`
`to. My review of lseaudoiri’s Canadian Application ("CA 2,251,265) shows that he also heated
`
`the. extracted krill oil in this application. At page 3 of CA 2,25l,265 it is stated: “ltlo get no
`
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`Reexamination U , S .S . 95/00 l ,774
`
`Declaration of Dr. Chong Lee
`
`of traces of organic solvents, lipid fraction 1 and ll are warmed (60°C for fraction l and. 700C
`
`for traction H) for 5 min under inert atmosphere,”
`
`l7.
`
`l8.
`
`As this protocol is nearly identical to Wt) 00/023546, it is thy opinion that the tractions in
`
`CA 2,251,265 would contain the sarne high amounts of solvent and humidity (126,, ll). .% in
`
`traction l and 6.8% in fraction ll),
`
`l-lowever, l note that, in CA 2,25l,265, Beaudoin heats at lower temperatures and for a lesser
`
`period of tirne.
`
`in my opinion, these temperatures and times, especially without vacuum,
`
`would not he sufficient for removal of residual solvent in terms oftime/temperature needed
`
`to evaporate the solvent.
`
`
`Residual Solvent.
`
`l9. My review of Maruyama (JP 2909508) shows that insufficient detail is provided, to allow me
`
`to discern how solvent was removed. For instance, in Working Example l, Maruyania states
`
`that he “removledl the ethanol as rnuch is possible.” l—lowever, no methodology is given.
`
`. in my opinion, a few options would have heen available to l‘vlaruyarna to remove the excess
`
`solvent. One possibility is that he used rotary evaporation to remove ethanol under reduced
`
`pressure at
`
`the boiling point at
`
`that pressure, perhaps even using, slightly increased
`
`temperature of the water bath in the rotary evaporation apparatus.
`
`1 would expect boiling of
`
`an ethanol azeotrope at around 40°C under 60~80 atrn of pressure during rotary evaporation
`
`(785°C without pressure, 2'. at 760 atm). However, it is noted that ethanol will still remain
`
`with much of the water in the li'actions it‘ this possibility for solvent removal was undertaken.
`
`This likely explains why Maruyama undertook a suhsequent wash with acetone ------- not only
`
`to recover phospholipids, but also to attempt to remove remaining water.
`
`. Another possibility is that Marugaina heated the oils on a hot plate in a manner analogous to
`
`Beaudoin, as explained above. This would not he a surprising step as l‘vlaruyaina describes a
`
`rnethod for “extracting total lipids from, the krill using ethanol” {Page 3, underlining, added)
`
`and it is understood among extraction scientists that all traces of solvent must he removed in
`
`order to quantify the total lipids recovered.
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`Reexamination U i S .S . 95/00 l ,774
`
`Declaration of Dr. Chong Lee
`
`
`l-lvdrolvsls May l—lave ()ecnrred ll lleatln liiids in the Beandoin and Maruvarna
`
`References.
`
`. l’lydrolysis ot‘pltospholipids cornrnonly occurs as a result of an enayrnatic reaction with the
`
`aid of phospholipase. However, non—enzymatic hydrolysis of phospholipids can occur with
`
`heat.
`
`This heat—induced hydrolysis preferentially occurs at
`
`the m~2 position and
`
`preferentially releases polyunsaturated fatty acids (PUFA) such as EPA and DHA in
`
`phospholipids of marine origin.3
`
`. This heat~induced hydrolysis has been observed in the literature. For instan te, in Medina at
`
`at, a heat treatment during tuna canning at llOOC for 55 minutes
`
`described. This resulted
`
`in considerable hydrolysis which released DEA floor the sn—2 position, as detected by 13C
`
`nuclear magnetic resonance (N MR) spectroscopy.
`
`l?’urther, in Grit or at, the extent of fatty
`
`acidmphospholipid ester bond hydrolysis was a function of temperature when hydrated,
`
`phosphatidylcholine was heated at 50~820C for varying periods! 6 The hydrolysis of
`
`phosphatitlyleholine followed a. pseudowfirst order kinetics. Also, in Herman and, Grovesi
`
`hydrolysis of phospholipids occurred, upon thermal stress during sterilization at l’Zl 0C in a
`
`soy oil—hased emulsion and resulted in release of free fatty acids.’
`
`. in the extracted krill oils produced by Beaudoin {WQ 00/023546), the acetone extracted oil
`
`and the ethanol extracted oil contained l0% and {5‘89/{33 moisture and volatiles, respectively,
`
`even after extensive rotary evaporation since water—miscible acetone and ethanol were used
`
`as solvents. Likewise, for h’laruyarnan his extracts would have contained signiti cant amounts
`
`of moisture and volatiles if he used rotary evaporation to remove the solvent from his extract.
`
`The remaining rnoisture would he sufficient to allow heat~induced hydrolytic reaction in
`
`lipids.
`
`5 See Medina of aid, “DC Nuclear Magnetic Resonance Monitoring of Free Fatty Acid Release After Fish Thermal
`Processing,” J Amen Oil Chem. Soc. 71(5): 479-482 (1994),, Appendix E.
`
`I
`
`“ Grit et a]. “Hydrolysis of Phosphatidylcholine in Aqueous Liposorne Dispersions” 1m.
`(1989), Appendix
`
`Pharmaceutics 50: 1-0
`
`.«
`pll of Phospholipid—Stahilized
`and Groves “The lnfluence of Free Fatty Acid Formation on
`7
`Triglyceride Emulsions” Pharmaceutical Research “1(5): 7744776 (1993)., Appendix G“
`
`7
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`Reexamination U a S .S . 95/00} ,774
`
`Declaration Of Dr. Chang Lee
`
`25. E‘ohewing the themedyrtamic principles,“ the higher the temperature, the greater the extent of
`
`hydroiysis is expected. Heat treatment at 125°C for 15 minutes weuld likely resuit in l'reat~
`
`induced, hen—enzymatic hydreiysis.
`
`ofthis
`
`intentionally left
`
`8
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`USSN, 95/003 ,774
`
`Declaration Of Dr. Chang Lee
`
`Amfimdix A
`
`Curricuium Vima M Di”: Omng LES
`
`0000010
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`

`

`Chang M. Lee
`
`Name 2 Chong M. Lee
`
`Education;
`
`Title : Professor Emeritus
`Department : Nutrition and Food Sciences
`institution 2 University oleiode Island
`
`l974 ; Food Chemistry
`University othode island, Kingston, Kl ; PhD. ;
`University ol‘t’ieorgia, Athens. GA; MS. ; 1970 ; Food Technology
`Dong—Girl»: University, Seoul. Korea ;
`;
`l968 ; Food Engineering
`
`Experience
`1988 — 201i 2
`8 2
`0 2
`" .
`2
`
`
`
`Professor. University of Rhode lsland
`Assistant Professor!" Associate Professor, University of Rhode island
`Assistant Professor, Drexel University, Philadelphia
`Postdoctoral Research Associate, University ol‘Georgia (W," Dr. Romeo Toledo)
`
`Professional Societies/Honors
`
`Institute oonod Technologists ; American Cherni cal Society ; Korea-Atnerican Scientists and Engineers Assoc; World
`
`Aquaculture Society; Sca ‘
`lv’licroscopy international -- Food Structure and l. Aquatic Food Product Technology : Editorial
`Board; Earl P. McFee AW. rdtfl 993) for recognition of distinguis ted research
`seafood science and technology.
`
`
`
`
`Process Kl produ t development; component characteristics on freeze-thaw stability; hydrodynarni c properties of
`‘
`
`‘6
`hiopolyrneric ingredients in textural modili cation and pli’ 'sical stabilization of gel-7L;
`d composite foods; cryostabilization of
`’9
`ish mince; use of suriini protein as a novel gel matrix; r .covery
`avor and nutraceuticals from marine lay—products;
`aquaculture larval feed for iulation and production; fish rneal—oil replacement in aquaculture feeds
`
`Past Research Accent llshment‘s
`spray—drying
`19694971 :
`Recovery of squid protein by water extraction
`19744976 :
`Developrne it of liniisli—based sausage products by texture optimizin technique
`19764981 :
`Evaluation of kinetics of a glucose—lysine reaction and its biological significance
`19804984 :
`Discovery of mechanisms of fat stabilization in proteinaceous matrices by a non—emulsion principle
`198l 4984 2
`Mechanical recovery meat and llavor froni crab and lobster bodies
`198 l 4985 2
`lireeze~thaw stabilizing mechanism of hydroxypropylated starch in frozen surnni-based products
`19844985 2
`Process optimization of stn‘imi manufacturing from red hake
`19874988 2
`Development ofnon~tliernial flavor recovery process from shellfish waste
`19894990 2
`Assessment of the gel—enhancing ability ol‘ biopolymers by hydrodynamic properties
`Development of a specialty canned mackerel lorinulated with organic seasonings;
`199l 4994 2
`
`introduction of light mackerel meat concept for formulated seafood prodt cts
`Refining and cryostabilization of fish mince for development ol‘mince-based seafood product markets
`Technology development for bio-production of seafood flavors from processing byproducts
`llydrolysate process development from squid processing byproducts for larval fish feed and pet food palatant
`
`1994—2000 :
`1996—2000 2
`2000—20l1 :
`
`Publications
`
`Book
`1. Lanier, TC. and Lee, CM. (ed) 1992. Suriini Technology. Marcel Deldter. New York.
`
`Book Chapters
`of squid as a protein resource. in Fishery
`l.
`..ee, QM... Lee, T-vC. and Cliichester. {1.0. 1974. The potential
`Products. (R. Kinezer, ed), Fishin News (Books) Ltd, Suriy, England.
`243—244.
`2. Lee, CM. 1984. Mechanisms offat dispersion in proteinaceous gel matrices.
`in Engineering and Food.
`(B. McKenna, ed), Elsvier Applied Science l’ulr, ltd, Essex, England, Vol. l, Cliapt. 40,
`403—4l4.
`3. Lee, CM. and Kim, ELM.
`The relationship of composite characteristics of rheological
`roperties ofsurimi
`
`in Food Engineering
`Process An: lications
`(M. l..elvlaguer and P. .ielen,
`Elsvier Applied Science
`Pub, Ltd, Essex, England, Vol. 1,
`l, p. 63—79.
`
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`Chang M. Lee
`
`
`
`4. Lee, GM. and Chung, Kid. 1990. The role of hydrodynamic properties ol‘biopolymers in texture
`
`
`strengthening/modilication and freeze-thaw stabilizing oI‘ surirni
`In Advances in Fisheries Technolo'T ' and
`Biotechnolog for Increased I’rol‘itabilitv {Ix/I. Voigt and R. Betta, ed.) chap.9, p.397~4l2, 'ICCIII’IOUIIC I’ttb.Co. Inc.
`Lancaster, Pa.
`5. Bullens, C.W., Llanto, Mil”, Lee, CM. and Modliszewski, ll. 1990. The function of carrageenan~based stabilizers to
`..........................:i.es.II.e§IineInexandliietecl"meiosis:
`
`
`Increasedlirotit
`abilityfl‘vl. Voigt and R. Botta, ed.) chap—4, p.313—324, 'I'echnomic I’uh.Co. Lanc ster, Pa.
`6. Lanrer, TC. and Lee, QM. ted.) 1992. Surirni "I‘eclrnology. Marcel Deicker, New York.
`7. Lee, CM.
`I992. Factors affecting physical properties ol‘l‘ish protein (surirni) gel. In _"
`Flick, R. Martin and R. Ory, ed), p.43—68, Teclnrornic Pub. L
`8. Lee, C.M., Wu, M.C. and Charla. M.
`I992. Ingredient and Ionnulation technology for surinri—hased products. In
`
`‘
`ii_:_I:_e_c_h__n_r_:-__l_r_;-_gy_‘{l.anier,
`and Lee. CM. ed), p.273~30l, Marcel Delrker, New York.
`
`9. Toyoda, K.,I irnura, 1., Fajita, 'I‘.,Noguclii, S. and Lee, CM. 1992. Surirni manufacturing process. In _§ti_r_i_r_n_i_ :lle
`(Lanier, 'l‘.C. and Lee, QM. ed), p.79~l l 1, Marcel Deklrer, New York.
`l0. Lee, QM.
`l99I. Surian : Science and Technology (YIII. IIui, ed.) In
`Teclinologv. Wiley-Interscience. New York.
`Il. ...ee, QM.
`l994. Relationships of rheological and hy rodynarnic properties ot‘hiopolynieric ingredients to the
`
`
`cornposile snrirni gel exture. In Devel
`_ ments in Food Engineering-Part: l (T.Yano, R. Matsurio and Ii. Nakarnura,
`eds), p.
`0] , Blacki Academic & Professional, I..orrdon.
`-ee, QM.
`l994. Stirirni processing from lean tish. In Seafood: Che
`
`
`
`rnistrv Processing: Iechnolocv and
`
`
`
`I997. Rheological effect ol‘preactivated hiopolyrneri c ingredients on texture and structure
`I3. Filipi, I. and Lee, CM.
`of cornposite suri’unri gel. In Engineering & Food at ICEF 7- Part 2 (Iowilt, R. ed.i), Section 1., p I7, Sheffield.
`Academic Press.
`
`I997. Technical strategies for development of formulated seafood products from fish ini‘nce.
`I4. Lee, CM.
`INwi".m
`, "
`
`sing, and Biotechnolog (F. Shahidi, Y. .Ionmes and DD. Iiitts, eds.) Chapter I3, pl 19—129,
`echrronric Publishing Co, Lancaster, PA.
`I Yang, ‘r”., and Lee, CM. 1999. Enzyme—assisted bioproduetion ot’lobster flavor from process byproduct and its chemical
`
`
`
`
`and sensory properties. In Transformation in Fisheries and A uaculture: Global I’ers ectives, ScienceTech Publishing Co,
`Inc, St..Iohn's, Chap I3, p.160—l 69.
`I6. Lee, CM.
`I999. Seafood wastes: A resource for flavor extracts. In 799 Innovations for Seafood, National Seafood
`Centre, Iiisheries R 8: D Corp, Queensland, Australia Iin press)
`
`Lee, CI I.
`I999. Sttrirni : Science and Technology (IIJ. Francis, ed.) In WiIe r
`'l‘echriologv. (2nd ed), p. 22292239,
`.Iohri Wiley 8: Sons, Inc., New York.
`its chemical
`Y’ rig, Y.,
`Lee, CM. 1999. Enzyme—assisted bioproduction oflobster flavor from process lay—product
` ect
`sensory properties. In 'l‘ranst‘orniation in Iiisheries and A“ uaculture: (illo‘oal I’ers
`ives, (Ii . Shahidi, ed), Cliap.13,
`
`
`
`13.169494, Science’l‘ech Publishing Co, Inc, St..Iohn‘s, Canada
`
`Lee CM. 2007. Seafood flavor from processing byproducts. lri Maximizin the value ol‘niarine hv— roducts (I7. Shahidi,
`ed.) Chap.
`p.304—327 Woodhead Publishing, Cambridge,
`20. Lee CIVI. ZOIO. liish rnince: cryostabilization and product formulationIn
`(Alvasalvar C, ed) Chap l3, p Blackwell Publishing, Oxford,
`plS -17 0.
`Apostolidis, Ernrnanouil and Chong Lee. Brown Seaweed—Derived Phenolic Phytochenricals and Their Biological
`Activities for Functional Food Ingredients V 7ith Foe us on Ascoplryllurn nododun'r.“ In:
`2011.
`
`'clo tedia ofFood
`
`
`
`and
`
`Refereed ArticIes
`
`I. Lee, C.M., Toledo. IIIII. Nakayania, '1‘. and Chichester, CO.
`spray-dried squid protein.
`.I. Food Sci. 39 : 735-738.
`I.ee,C.M. and Toledo,I?..T.
`I976. Factors affecting textural characteristics of cooked conrnrinuted Iiin muscle.
`I. Food Sci. 4i:
`I--297.
`
`I974. Precess requirements and properties of
`
`I977. Degradation of Iiin muscle during mechanical deboning and storage with
`Lee, (1M. and Toledo, RE.
`emphasis on lipid oxidation. 1 Food Sci.
`: 1646-v 1649.
`4. Lee, C.I\/I., Lee, T-C. and Chichester, CO.
`I977. Effect oIMaillard reaction products on the absorption of
`I.-tr”yptophan. Comp. Biochem. Physio]. 56A : 473-476.
`5. Lee, C.M., Chichester, {7.0. and Lee, THIS.
`I 77. Et‘tect ofMaillard reaction products on disaccharidase
`activities.
`.I. Agr. Food Chem. 25 : 775~778.
`
`0000012
`
`0000012
`
`

`

`Chung M. Lee
`
`6. Lee. Chi. Lee, T-C‘. and Chichester, CD. 1979. Kinetics of the production of biologically active Maillard
`browned products in apricots and glucose-L-tryptophan.
`.l. Agr. Food Chem. 27 : 478-482.
`7. Lee, C i. and Toledo. Rfl‘. 1979. Fri. and ingredient influences on texture of cornminuted fish muscle.
`J. Food Sci. 44: 16l5—l618.
`
`l98l. A microscopic study of the structure of meat emulsions and its
`Lee, Chi. Carroll, R. and Abdolla‘ni. A.
`relationships to thermal stability.
`3. Food Sci. 46 : 1789~l'795.
`9. Lee. QM... l’larnpson, l. and Ahdollahi, A. l981. Fffect ofphysical properties of plastic fats on thermal stability
`and mechanical properties offat-protein gel products.
`J. Amer. Oil Chem. Soc. 58: 783—787.
`l0. Lee. CM. and Ahdollahi. A. 198d. Effect of physical properties of plastic fat on structure
`material properties
`of fish protein gels. J. Food Sci. 40: USS-1759.
`ll. Carroll. Rd. and Lee, CM. 198d. Meat emulsions: Lipid-protein relationships. 1. Scanning Electron
`Microscopy 198l: 447—452.
`l2. Kazantzisfi). and Lee.C.lVl. 1983. Effect of rheological interrelationships between starch gel and fat on the fat
`dispersion in farinaceous
`matrix. l. Texture Studies. 14: 303-—3l3.
`l3. l..ee,C.lVl., Slierr,B. and Kohfl’.
`l984. Evaluation oflrinetic parameters for a glucose-lysine Maillard reaction.
`I. Agr. Food Chem. 32.: 379-387.
`l4. Lee,C.l\/l. and Patel.K. 1984. Analysis ofjuiciness characteristics of commercial frank futters.
`.l. Texture Studies
`67-73.
`l
`l5. ,..ee, CM. and Toledo. FLT. 1984. Cornpari son of shelf-life and (uality of mullet stored at zero and sulizero
`temperature. J. Food Sci. 49 : 317-344.
`38(1. l) : 69-80
`l6. Lee, QM.
`Surirni process technology. Food Technol.
`) : 63—72
`Lee. CM.
`l985. Microstiucture of meat emulsion in relation to fat stabilization. Food Microstructurc
`, C
`l l5—124
`l8. Lee
`.M.
`1986. Surimi manufacturing
`fabrication of suriini~hased products. Food Tecli‘nol. 40(3) :
`l, . Kim. ELM. and Lee. (1M. 1987. Effect of starch on textural properties of surimi gel.
`.l. Food Sci. 52 : 722—725.
`'20. Lee, C.r\’l.. Whiting, RC. and .lenkins, R. K. 1987. Relationships of formulation
`processing parameters to
`textural characteristics offranlituiters.
`.l. Food Sci. 52 : 896—900.
`
`1
`
`'21. Kim. ELM. and Lee, CM. 1987. Textural properties and structure of starch—reinforced snrimi
`heat—setting. Food Mierostmcture 6(1) : Sl~89.
`'22. Douglas—Swarm, M. and Lee. CM. 1988. Comparison ofthemiostability of red bake and Alaska pollock surimi
`during processing.
`.3. Food
`53 : 1347—1351.
`23. Lee, CM. and Hardy, C.
`l989. Effect of cocoa feeding on human lactose intolerance. Amer. .l. Clin. Nutr. 49 : MUS—44.
`24. Sherr. 8.. Lee, CM. and .lelesciewicz. C. 1989. Absorption and metabolism of lysine~lvlaillard products in
`relation to utilization of L~lysine.
`.l. Agr. Food Chem. 37 : l19—122.
`25. An, ll, Wei, Cl. Zhao, .l., Marshall, MR. and Lee, CM. 1989. Electrophoretic identification of fish species
`used in sttriini products. J. Food Sci. 54 : 253-257.
`26. Lee, CM. and Chung, Kll. 1989. Analysis of suriini gel properties by compression and penetration tests.
`.l. Texture Studies 20 : 363-377.
`
`as affected by
`
`
`and Lee. CM. 1990. Effect of powdered cel 'ulose on the texture and freeze—thaw stability of
`2?. Yoon.
`surirni-based shellfish analog products. J. Food Sci. 55 : 87—91.
`28. Chung, Fill. and Lee. CM. 1990. Relationships between physicoclieniical properties of nonfish protein and
`textural properties of protein-incorporated surirni gel. 1. Food Sci. 55 : 972-97
`l’luang, Z~B.. Leihovitz, ll.. Lee, CM. and Millar. ll. 1990. Effect of dietary fish oil on omega—3 fatty acid levels
`in chiclren eggs and tigh flesh. J. Agr. Food Chem. 38 : 743 - 747.
`30. Yoon, KS. and Lee. CM. 1990. Cryoprotectants effects in surinii and surirni/nrincehased extruded products.
`J. Food Sci.
`: lth‘t—lllé.
`
`29.
`
`31. Dyrnsza, ll.A.. Lee, C.l‘v’l.. Saibu, l...0., llaurt. .l., Silverinan, Gd. and Josephson. ES. 1990. Gamma irradiation
`effects on shelf life and gel-forming properties of washed red li;al<e(Ui‘opli'y'cis cliuss) mince. .l. Food Sci. l745- l 746.
`
`J. Food Sci. J. .:
`
`2.66.
`
`33. Yoon. KS. Lee. CM. and l-lufnagel. LA. 199
`fish rninee. 3. Food Sci. 56‘ 294 -- 2.95.
`
`Effect of washing on the exture and mic rostruct'ure of frozen
`
`Textural and microstruetural ‘roperties of frozen fish mince as
`34. Yoon. KS. Lee. CM. and l-lutrtagel. LA. 199
`affected by the addition of non fish proteins and sorbitol. Food Structure l0: 255-265.
`35 Lee, HG, Lee, (11%.. Chung, KH. and Lavery. SA. 1992. Sodium aseorliate affects suriini gel—forming
`"
`’7
`properties. J. Food Sci. 57: 1343—13" I.
`
`0000013
`
`0000013
`
`

`

`36. ‘i’oo, B. and Lee, CM. 1993.
`Chem. 41: 190192.
`
`'i‘herinoprotective effect of sorbitol on proteins during dehydration. 3. Agr. Food
`
`37. Chen, .l-S, Lee, (2M. and Grape, C. 1993. Linear prograrnrniong and response surface niethodoiogy to optimize
`gei texture. J. Food Sci. 58: 535—538.
`‘i’oo, B. and Lee, CM. 1993. Rheological relationships between surimi sol and get as affected by ingredients.
`5. Food Sci. 58: 880883.
`
`39
`
`. Yoo, B. and Lee, QM.
`’l‘echnoi. 27533037.
`
`l994.
`
`'i'hernial geiation characteristics of composite surirni sot. Lebensrn.—Vv’iss. u. ~
`
`Chung M. Lee
`
`J}. t...»
`
`'Yoo, B., Lee. CM. and Shin. HS. 1994. Shear modulus (6") of surirni sol measured by various viscornetric methods
`and its relationship to gel properties in the composite system. Foods and Biotechnology 3: l65—168.
`. Lee, C.M., Trevino, B. and Chaiyavvat. M. 1995. A simple rapid solvent (CECE ~MeOH) extraction method for
`determination or" total 1ipids in fish tissue.
`3'. AOAC internationai 79:487-492.
`i997.
`. Lee. (lb/1.. iiilipi. 1., Xiong,
`Smith. 1)., Regenstein, 3., Damodaran. 8.. Na, C—Y., and Hague,
`Standardized faiiure compression test of protein gels from a collaborative study.
`.1. Food Sci. 62:1 l63--i166.
`’. Ellis. RC, Siiva. ML. and Lee. CM. 1997. Statistical ciassiiication ofseafood quality.
`.1. AOAC intern.
`80: 1347-1359.
`
`'
`
`OM. 1998. Preact‘
`». Filipi,1. and Lee.
`Lebensrn.-V 7iss. u.--Teclmol.
`1: i'
`
` ‘ied iota-carrageenan and its rheoiogica1 effects
`'7I
`
`composite surinii gei.
`
`. Jayarajah, C. and Lee. OM. 1999. Ultratiltration/reverse osmosis concentration oi"1obster extract- .1. Food Sci. 64: 93--
`98.
`
`’
`
`.
`
`l999. Production of seafood iilavor from red hake (L00pizycis chi/.33) by enzymatic hydro1ysis.
`on
`o ’r
`'
`4;.) 60-1,.) 6(L
`
`irnin. .1.Y. and Le‘, CM.
`J. Agric. Food Chem. 47:
`'1999. Causes for soft flesh in giant grenadier
`. Crapo, C., Hinie1b1ooni, 8., Pfiitzeirreutwe, R., and Lee, CM.
`(Albatrossia pectoralis) til ets.
`.l. Aquatic Food Product Technol. 8(3): 55—68.
`iinrn. .1.Y. and Lee, (1M. 2000. Gelatin; i and water binding properties oftransglutaminase—treated skim niilk powder.
`.1. Food Sci. 65:200—205.?
`
`49.
`
`U1 9
`
`LII s...
`
`BOD reduction in a squid processing
`
`Crapo, (I, Hinie1b1oo‘ni, 8., Ptutzeirreuter. R., and Lee, CM. 2000. Texture modification processes for giant grenadier
`(Albatrossia pectoralis) fillets. .1. Aquatic Food Product Technot 8(4): 27—40.
`Lian, P.Z., Lee, CM. and Hufnagel, L. 2000. Physicocheniica1 properties