food flavor review

8/12/2019 food flavor review

http://slidepdf.com/reader/full/food-flavor-review 1/24

FOODBIOTECHNOLOGY, (2&3), 167-190 (1994)

ENZYMES AND FOOD IKLAVOR - A REVIEW

j$&sten'* andA. ópez-Munguía2

ORSTOM. nstitut Français de Recherche Scientifiquepur le Ddveloppement en Coo-#ration. Cicer6n 609, Col. LosMorales. Mexico DR , CP 11530,MEXICO.

Instituto d e Biotecnologfa. Universidad Nacional Aut6noma de MBxico. Apdo Postal510-3,Cuernavac a, Mor., CP62271,MEXICO.

ABSTRACT

The use of enzymes in flavor generation in food technology is reviewed. In the first part, im portant products derivedfrom natural macromolecules present in foods suchas ats, proteins, nucleic acids and flavorp recursors arediscussed interms of the enzymes involved in thereactions and therelation ofthe products with flavor. Enzymes that are used toeli-minate natural or process induced off-flavors are.dsodiscussed.In the second part, the useof enzymes for the direct syn-thesis of flavoring compounds is presented.

WTRODUCTION

Flavor compounds synthesis by biotechnological processes plays nowadays an increasing role

in the food industry. This is the result, among other things, of scientific advances in biological pro-

cesses, making use of microorganisms or enzymesas an alternative o chemical synthesis, combined

with recent developments in analytical techniques such as HPLC, GC, IR or mass spectrometry

(Knorr1987).Thiscanbeevidencedby the great number of reviews related to flavorpublishedin he

last twelve years covering a broad area: Schindler and Schmid (1982), Kempler (1983), Sharpell

(1985), Gatfield (1986, 1988), Crouzet (1989). Welsh et hL(1989), Herráiz (1990), Cheetham

(1991,1993), Janssens et aL(1992), Gutierrezand Revah.( 1993); or concerning specific topics: li-

pases characteristics (Borgström and Brockman 1984) and their industrial applications (Macrae

1983,West 1988), enzymes involved in-the cheese flavor biosynthesis (Kinsella and Hwang 1976,

Law 1984, Seitz 1990), enzymes affecting the flavor of citrus products (J3ruemmere? al.1977) or tea

(Jain and Take0 1984), enzymatic aroma genesis in food (Schwimmer 1981) or biocatalysts in the

natural generation of flavor (Schreier 1985) to give onlya few examples.Thereis stillmore potential

for this area in biotechnology since liquid cultures of plant cells may also be used as a technique to

* corresponding author

Copyright 1994 by Marcel Dekkcr Inc.

167



168 CHRISTEN AND L6PEZ-MUNGUiA

synthesize a wide array of chemicals (Whitaker and Evans 1987, Knorr eral.1990). Research in this

area for new products and bio-processes is also enhanced by a growing market and an increasing

public concern for the total wholesomeness and chemical safety of food ingredients (Basset,l990).

From a total world market of 6 billion dollars for the flavor and fragrance industry in 1990, food fla-

vors account for25%, ith about 5%annual growth rate (Cheetham 1991). Flavor sales were esti-

mated tB be aboutU S$675 millions in 1991and are expected to reachUS$376 millions in the Euro-

pean Community (Cheetham 1993). Most of the major companies producing aromas are carrying

out research programs for developing the biotechnological production of such compounds (Dziezak

1986a). It must be alsopointed out that a specific policy concerning labelling of processed foods

containing natural compounds has been issued in several countries (e.g. in the EC with the directive

.published in July 1988 in theOfficial Journal of the European Community, Spinnler 1989).

On the other hand, the food industry has been strongly influenced by the increasing public awa-reness of the nutritional characteristics of their diet and, in particular,ofthe additives used in the food

industry.This is shown, not only by the high number ofindustrial products low in fat, sodium, caffei-

ne or cholesterol, but also n the displacement of saccharine by aspartame and the search for natural

colorants or alternative antioxidants and preservatives.

Enzymes asbiocatalysts offer a wide variety of possibilities for food flavor production: their

specificity, whether applied via whole-cell or cell-free systems enable the production of certain

chemicals difficult to synthesize; their stereoselectivity is an important advantage for the food

industry where aspecific optical conformation may be associated to flavorproperties. Enzymes may

alsobe used directly as food additives, not only toproduce or liberateflavor from precursors, but also

to correct off-flavors caused by specific compounds, naturally occurring or produced during proces-

sing (Bigelis,1992). Whitaker (1990) presents in a broad review on the prospective of enzymes in

food technology in general. Enzymes involved in flavors may also be endogenous, inherent to the

food or may come frommicrobial sources, added intentionally to foodsor coming from contamina-

tion. In Table 1,the main objectives for the use of enzymes in flavor technology are presented.

In this article, different ways in which enzymes are related to flavor are reviewed, presenting

examples of actual research in this area as well as potential applications. In some cases, processes

arid reactions known for two decades-are mentioned and updated with recent advances such as who-

le-cell biocatalysts or reaction in organic media.

~- . _

ENZYMATIC MODIFICATIONS OF MACROMOLECULES

Almost all macromolecules present in foods have an impact on flavor when hydrolyzed. There

is a wide variety ofenzymes available for-thehydrolysis ofproteins, starch and othercarbohydrates,

fats and nucleic acids (Shahani e t al.1976). so there are enormous alternatives for their

transformation or for the development of processes having asamain objective the production of fla-

voring compounds.

1. Fats.

There &e many examples in the food industry where the main flavor properties are derived

from far. As proof of the interest of scientists and companies in the applicaticn of lipolytic enzymes



E N Z Y M E S A N D F O O D FLAVOR 169

TABLE -Enzyme technology related to food flavor.. dditives to enhance orproduce flavor from precursors.. iocatalysts in processes for flavor production.. dditives in flavor extraction processes from natural raw materials..Activation of endogenous enzymes to induce reactions leading to flavor production.. nactivation ofendo genou s enzymes to avoid off-flavor generation..Use ofenzvm es.for the elimination of off-flavors.

.

as a tool to improve cheese manufacture, one can refer to the reviews of Arnold et al. 1975), Kilara

(1985a) and Dziezak (1986b).The basic and first step of the process is the lipase-catalyzed hydroly-

sis of glycerides. In some cases, the free fatty acids released are converted to the flavoring com-

pounds by microorganisms (e.g. in the case of cheeses). Fatty acid profiles required for particular

flavors are obtained with various lipases: short chain fatty acids (C4) will develop a sharp, tangy

flavor tending towards rancid notes, while intermediate chain fatty acids (like C12) are associated

with a soapy flavor (Nelson 1972). This isa problem for example in the piña colada beverage were

the C12 fatty acid of he coconut isreleased by the thermostable lipase of the pineapple producing a

strong soapy off-flavor in the cannedbeverage (Heath and Reineccius 1986). On the other hand, lar-

gest fatty acids (up to C12 are known to do not make a significant contibution to flavor.

(c6 CIO)isimportant in fat flavor development: pancreatic lipases are adequate for short chain fatty

acids,Aspergillusand Candida spp. for a wide range of sizes and Penicillium roqueforti for buty-

ric acid release (Godfrey andHawkins 1991).A. oryzue liberatesc6 Cl0 fatty acids, characteristic i

of Cheddar,sothat the ripening process might be reduced from several months to only 12-72 hours.

Butyric and propionic acidsarecharacteristicof Romano, Provolone and Swiss cheese, respectively

and while the former is released by lipase action, the latterisproduced by Propionibacteriumfer-

mentation.

The rationalization of this traditional microbiological process has resulted in the development

of theEnzyme Modified Cheeses (EMC), obtained by direct addition of enzymes to fresh cheese. As

an application of this process, Torres and Chandan (1981) used lactic culture, yogurt culture and li-

pase preparations to modify flavor, tex-ture and to reduce the ripening time of the Latin American

white cheese. Revah and Lebeault (1989), working in the manufacture of blue cheese, demonstrated

that controlled lipolysis results in a concentrated product, 20-30 times stronger in flavor than the

maturecheese. The accelerated ripening process is currentlypracticed with pancreatic and microbial

lipases as well asproteinases (Rabie 1989). Another applicationofthisprocess has been proposed by

Panne1and Olson (199 1a,b), for the production ofmethyl ketones, major components of blue cheese

flavor. In thiscase they used pancreatic lipase and spores ofPenicillium roquefortìin milk-fat coa-

ted microcapsules. They reported the production of 2-pentanone, 2-heptanone, 2-nonanone and he-

xanoic, octanoic and decanoic acids atthelevelof 12mglg capsules in17days.In this process itisas-

sumed that the spores convert the lipase-hydrolyzed fatty acids to ketones, thecritical pathway being

/

I+ P

A balance between these extremes with only small amountsof intermediate length fatty acids '

> (i



170 CHRISTEN A N D L6PEZ-MUNGUÍA

the liberationof free fatty acids. Cheddar cheese has alsobeen studied (Arbigeet al. 1986): afteriso-

lating a very active lipase fromAspergiZZus oryzae, these authors canied out the accelerated ageingof the cheese by adding a combination of alipase and aprotease, obtaining a balance between flavor

development and body breakdown in areduced time. El-Sodaetal. 1992), by using freeze-shocked

mutant strains of Lactobacillus casei as a source of lipase, could shorten the ripening time of the

Egyptian Ras cheese, minimizing the development of bitterness. As another example, Davide and

Foley (198 1), ried to improve sensorial properties (appearence, flavor and texture) of Cheddar type

cheese withcoconut oilas asubstituteformilkfat by addingcommerciallipasepreparations. Experi-

ments showed it was not feasible. As a conclusion, full flavored cheeses of different types may be

obtained, with a specific fatty acid profile, depending on the enzyme used (Godfrey and Hawkins

1991, Kim Ha and Lindsay 1993).

Lipases have also been used for the modification of animal fats and tallows.Asan example, the

production of aromas from raw material such as butter has been proposed (Seitz 1990). In 1984, a

process for producing an aroma rich fat phase from butter was patented: a mixture of P.roqueforti

cells and pancreatic lipase was used on a pilot scale (Kunzer al.1984). Another process for this pur-

pose employed extra and intra cellular enzymes of Lactobacillus plantarum (Reimerdes 1984).

Bothauthorsclaimthattheproductcanbe added tocheeses, sausagesormeatproducts. Chen andPai

(1991) applied this process to the hydrolysis of milk fat in reversed micelles stabilized by lecithin.

They optimized this technique for parameters such as temperature, pH and molar ratio of water to

surfactantand found that enzyme activity could be improved with increasingenzyme and surfactant

concentrations.Garcia t al. 1991) carried out a selective ipolysis of glycerides from butteroil with

anAspergillus nigerlipase in order to obtain a pleasant flavor enhancement (ieleasing preferably

butyric acid). Luck and Hagg (1991) discussed the influence of parameters such as pH, enzyme

concentration and temperature on the kinetics of lipolysis in an enzymatichicrobiological process

for the production of cheese flavor from a butter emulsion. Finally, it is nteresting to point out that

fungal lipase produced in solid state fermentation displayed3.3 times greater activity than in sub-

merged culture and could be applied to hydrolyze oliveoilor for a simple control of flavor profile of

lipolyzed milk (Chen and McGill 1992).

Although lipases and cheeses are the most common enzymes and substrates, respectively, in

relation to enzymatic flavor production from fats, there are other examples: active soya flour is

added as a source of lipoxygenase- acting by hyper oxidation of linoleic acid and other polyunsatu-

red lipids - to bleach and to improve the volarde composition of bread. It has been found that the

concentrations of hexanal, hexanol, l-penten-3 -01,l-pentano1 and 2-heptanone are increased uponthe addition of soya flour (Luning et al.1991 Addo etal. 1993). Fatty acids are oxidized for the pro-

duction of "green" flavor components, the so-called "leaf aldehydes" and "leafalcohols", which may

be obtainedenzymatically through lipoxygenase and hydroperoxide yase. However,thisarea isstill

far from practical applicationsdue to the lack of availability of these enzymes (Gatfield 1988).

Josephson and Lindsay (1986) reported that lipoxygenase could be employed successfully in

the generation of fresh fish aroma, liberating alcohols and carbonyls from polyunsatured fatty acids.

They also pointed out that plant-derived lipoxygenases may be potentiallyused to restore thisaroma

in fish.-. - - _- - . .



ENZYMES AND FOOD LAVOR 171

2. Proteins.

The development of soy sauce fermentation, centuries ago, is probably one of the first proces-

ses where traditional biotechnology had a stronger impact on flavor than in preservation. More

recent developments of protein hydrolysates from vëgetals, soy bean, wheat or yeasts are

'specifically related to the production of flavor and flavor enhancers (Kilara 1985b). Although the

most important commercial product -yeast extraçt - is produced by autolysis, which involves the

activation of degradativeenzymes nherently present in the yeasç (Dziezak 1987,Mermelstein 1989,

Nagodawithana 1992), when proteases ike papain are used, glutamic acid may be obtained as a free

amino acid : ts perception in food is the main factor influencing flavor. Cysteineisalso important in

the developmentofmeat flavor due toits participation in the Maillard reaction (Tyrrelll990, Grosch

and Zeiler-Hilgart 1992); methionine, eucine and isoleucine (in that order) are the next most reacti-ve (Weir 1986). Different proteases have been proposed for the production of flavorings from pro-

tein hydrolysates: an immobilized protease from Penicillium duponti for the hydrolysis of soy pro-

tein; pronase for casein hydrolysis; pepsin andrenin or pea protein and reconstituted skimmed milk

respectively; pepsin for cotton seed and a variety of proteases for the protein from faba bean, as re-

viewed by Weir (1986).

After proteolysis it is possible to further enhance the flavor by treatment with a glutaminase

(Yasuyuki et al. 1989). The flavor enhancing glutaminase enzyme increased the level of glutamic : '

acid by a factor of 2.6 in a mash ofKoji wheat treated withBacillus subtìlìsand Aspergillusoryzae ,

proteases.

A succesful approach in this context is that of "cascade hydrolysis". It consists oftwoorthree

successive enzymatic hydrolysis steps starting from an alkaline protease allowing the pH to fall or

maintaining i t constant. The final steps may include peptidases to hydrolyze fragments that will

otherwise give bittemess to the product. Acid hydrolysis results in products such as mono and ,

dichloro compounds that have recently given rise to concem (Godfrey 1990).

Peptidases and proteases may also be used in cheese making processes (Kilara and Iya 1985).

Muir et a1.(1992), reported that enhancement of the level of degradative enzymes in reduced-fat

cheese, by addition to curd of an attenuated starter culture rich in peptidase and protease, resulted in

significant improvements in both intensity of Cheddar flavor and in the mouth-coating character. In

areview, Femandez-García (1986) discussed thenew trends in the accelerating process of cheese ri-

pening. It appears that not only lipases may be helpful, but alsoß-galactosidase and proteases. If the

use of a lactase preparation displayedan improvement in sensorial properties of cheese, proteasesmustbe employedcarefully because of the possible induction of bitter taste due to the release of hy-

drophobic residues (Femandez-García et al. 1988).Thisresearch group also demonstrated hat neu-

tral bacterial protease could highly increase the amount of non-protein nitrogen in two kindsof Spa-

nish cheese and therefore contribute to the accelerationof the ripening of such cheeses (Femandez-

García etal. 1990,1993). Ithas alsobeen reported that bacterial methioninase may be helpful in the

generation of aroma when added to unripened Cheddar cheese by promoting the transformation of

sulphurcontaining amino acids into methanethiol, one of the constituentsofthe typical aroma of that

cheese (Lindsay and Rippe 1986).

i



172 CHRISTEN A N D L6PEZ-MUNGUíA

dso, during fermentation, specific enzyme activities are important in flavor generation. In a

recent publication, the importance of the combined protease and esterase activities of wine yeasts on

aroma compound formation was studied (Rosi et ~1.1989). t is probable that the advances in

research conceming the specific activities nvolved in aroma production during microbial transfor-

mationswill have an impact on traditional processes. This is already the case in the dairy industry

andmay also include in the near future other fermented products such as wine and beer.

3. Nucleic acids.

Besides glutamate, the most widely used flavor enhancers are 5'-ribonucleotides 9-GMP and

5'-IMP). They canbe obtained by fermentation orby nuclease- mediated hydrolysis fromRNA (Na-

kao 1979). The nucleotides may be obtainedby direct additionof the enzymes to the food or in enzy-

me reactors using soluble or immobilized enzymes (Benaigeser al. 1990, Cho and Lung 1991,Ol-

medo et al.1993).The enzymatic process utilizes 5'-phosphodiesterase produced from Penicillium

citrinum. t is important to use an enzyme preparation free of contaminating nuclease activities. 5 -

AMP is obtained in a second enzymatic conversion from5'AMPwith adenylic deaminase. It has al-

sobeen reported that a mixture of IMPand monosodium glutamate could provide a strong "meaty"

taste and develop a sense of greater smoothness, body and viscosity (Bigelis 1992).

4. Hydrolysis of precursors.

As early as 1956, Hewitt reported that flavor lost by food processing could be restored by

addition of an appropriate enzyme preparation (Crouzet 1977). The hypothesis was that flavor

precursors, glucosinolates in that case, were still present in the food after processing, while flavor

had been lost and enzymes deactivated. Upon addition of fresh enzymes from the fresh product or

from a part of the plant of the processed food, the reaction giving rise toflavor compounds could be

restored. Thiswas the case with watercress and later with mustard, cabbage, string bean, onion and

raspbeny (Gatfield 1988).

Sulfur volatile compounds are produced by alliaceous (onion, garlic, leek,...) and cruciferous

(cabbage,mustard, broccoli, horseradish,...)plants by direct action of enzymes. With the former, en-

zymes knownas alliinases produce disulfides and related volatile substances from derivatives of

cysteine (S-allyl and S-propyl cysteine sulfoxide for garlic and onion, respectively) while in the lat-

ter, thioglucosidases like sinigrinase, sinalbinasé,myrosinase produceisothiocyanates, responsible

of the pungent taste of these plants. Inboth cases, enzymes and substrates are compartmentalized,so

when the tissues are disrupted, enzyme and substrategenerate the flavor compound. Using this well

known mechanism, horseradish aroma has been produced with myrosinase immobilized in a plug-

flow reactor (Gatfield etal.1983). Hanley etaL(1990) applied this enzyme to the hydrolysis of glu-

cosinolates in a low water system, finding out that reverse micelles process was more efficient than

aqueous buffer solution. Someof theseproducts are toxic: although a widevariety ofglucosinolates

are present in cruciferous seeds, the principal one in rapeseed and crambe is progoitrin which yields

goitrin, a growth depressor, after hydrolysis with myrosinase (Liener 1987).

t

- -- - - --



ENZYhlESAND FOOD FLAVOR 173

Hundreds of compounds from biosynthetic pathways have been identified n flavors. Some of

these compounds are derived from the direct action of enzymes precursor-transforming and often

play asignificant role in defining he aroma.In a general model, a glycosidase s used to hydrolyze

, he precursorof the type carbohydrate-aglycone. or this reason, enzymesarenow included in the

aroma extraction techniques (Simultaneous Enzyme Catalysis Extraction: SECE) (Schwab and

Schreier 1988). InTable 2, a survey concerning the kind of flavor products obtained by enzymatic

extraction is presented.

During maturation, odorous monoterpenes are converted to glycosyl derivativessuchasO-a-L

rhamnopyranosyl-ß-D-glucopyranosidesnd O-a-L arabinofuranosyl-ß-D-glucopyranosides.n

most cases, these glycosides accumulate n the fruit and canbe found at a concentrationgreater than

the free aroma constituents.However, the enzymatic treatment must be short and specific, otherwise

the changes in aroma may result from side ncubation effects,asendogenous enzymes like esterases,

lipoxygenases, aldehyde-lyase or alcohol dehydrogenase which are active for a long periodof time,

as demonstrated in apple juice by Jenniskenset aL 1991).

For many fruits, there are nowenzymaticprocessesproposedor an efficient release of aroma

compounds. Vasserot et al. 1989), studied the properties of a ß-glucosidase from a Hunseniasporu

strain. They showed that this enzyme, due to its lack of substrate specificity,was highly interesting

for fruit aroma liberation, especially for bound terpenols. Its activity s inhibited by glucosebut acti-

vated by ethanol. Side activitiesof commercial enzymatic products are also used for this purpose.

This is the case of arabinopyranosidase activitiespresent in hemicellulasepreparations. In a syste-

matic study carried out by Cordonnier et aL(1989), in order to test the abilityof 34 commercial

preparations o liberate aroma from glycosidic precursors,5enzymes were selected due to theirß-D

glucopyranosidase, a-L rhamnopyranosidase and a-L arabinofuranosidase activities. These

enzymes were able to liberate linalool and geraniol. It is clear that in the near future, commercial

enzyme preparationswill be developed for specific fruits to liberate specificaromacompounds. Ho-

wever, there are still some limitations o overcome, such as inhibition by glucose or by ethanol, the

pH-activity profile and the thermostability.

Another interesting feature is hat many precursors are also found in other parts of the plant

(leaves, skin, etc.) so t might be possible to produce natural aroma from agro-industrial residues. An

example of this trend is the hydrolysis of picrocrocin, the glucoside precursor of safranal, the

essential volatile characteristicof the saffron aroma and odor, by ß-glucosidase (n;orra et aZ.1992).

The same type of process may be possible in the near future for the production of vanilla, by

treatment of the precursor, the glucovanilline present in the pod with a ß-glucosidase. Pouget et

a¿.( 1990) showed the feasabilityof the process at a laboratory scale submittingvanilla pod residues

to the action ofAspergillus niger hydrolases. This process has been developed at a pre-industrial

scale (Therre 1990).

Using sensory analysis, Abbotterd. 991)found that glycosidic hydrolysatescontain aroma

compounds that are very importantinhigh qualityShirazwine. Forthispurpose, they hydrolyzed the

volatile componentsderived fromisolatesof wine and juice of Shiraz grapes, with a non specific gly-

cosidase. By sensorial analysis, the hydrolyzed samples were found to contribute to notes such as



174 CHRISTEN AND L6PEZ-MUNGUIA

TABE2 -Examples ofaglycons involved in the flavorof fruits liberated by enzymatic treatment.

Fruit Enzym es Bound volatiles . Authors *

Papaya emulsin*

acid phosphatase

Apple

Various fruits

Raspberry

Strawberry

Grape

Lulo fruit

ApricotPeachYellow plum

Vanilla

romito

4pricot

Blackberry

4frican mango

emulsin'

endo-glucosidase

tannaseanthocyanase(from A.niger)

pectinase

pectinase

glucosidase

ß-glucosidase from yeastsvarious (fungal enzymes)almond emulsinfungal ßapiosidase

glucosidase '

emulsin*

ß-glucosidasehesperidinase

ßglucosidasepectinase

ß-glucosida&

pectinase

ßglucosidase

benzaldehydebenzyl alcohol2- phenylethanol.linalool2.6-dimethyloct-7ene-2,3,6-trioI

C I3 norisoprenoids

linalool

C I3 norisoprenoids(ionones & damascones)

(s)-Zmethil butanoic acidbenzy l alcohol2,5 dimethyl-4-hydroxy-2H-furan-3-oneE-cinnamic acidbenzoic acid

norisopenoids from lutein,violaxanthin. neoxanthin.monoterpene alcohols .

C-13 norisoprenoids: ßdamas-cone, ß ionone.megastigm-diolsapiosylglucoside of terpenols

(R)-linalool and otherterpenoids.

MonoterpenesC- I3 nonsoprenoidsMarmelactones (peach)

vanillin

2-phenyl eth&oJ, benzylalcohol, benzoic acidsh i-kimate type products....

hexanol,2-phenylethanol,linalool, dienediols, nerol,...benzyl alcohol; 3-hexen-1-01,benzoic acid,vitispiranes, heptahol

8monoterpene alcohols, 5 alde-hydes, 7 esters, 5C-13 noriso-Drenoids. 4 acids.

Schwab etal.1989

Schwab &Schreier 1988

Shoseyov et al.1988

Pabst etal.1991

Wintoch et al. 1991

Williams et al.1992

Günata et al. 1990

Sefton &Williams 1991

Dupin et al. 1992

Suarez er al.1991

Krammer et al. 1991

Belford er aL'1992

Marlatr et al.1992

Salles et al.1991

Humpf & Schreier 1991

Adedeji et al.1992

Emulsin is a co mercial j3-glucosidase enzyme preparation.



ENZYMES AND FOOD FLAVOR 175

"earthy", "stalky" and "tobacco".Wines onsidered of higher quality wereratedhigher n these non-berry attributes. The use of this technique lead Francis et aL(1992) to similar conclusions with Se-

millon, Chardonnay and SauvignonBlancgrapes.Enzymatic or acid hydrolysiswas ound toenhan-

ce intensity of the attributes "honey", "tea", "lime" or "floral" present in the neutral wine.

5. Eliminationof off-flavorsin foods.

If some enzymes, like ipoxygenasesinsoybeans, lipases in dairy products or proteases n aged

cheeses, have been reported to be associated with off-flavor generation (Heath and Reineccius

1986), here is alsoan ncreasing number of enzymes proposed to eliminateoff-flavors naturally oc-

curing in foods or producedasa consequence of food processing. Some examples date back decades.

This is the case of the use of amicrobial naringinase (a fungal enzyme withrhamnosidase and ß-glu-

cosidase activities) to debitterize grapefruit uice or grapefruit concentrate (Chase 1974).This en-

zyme hydrolyzes the naringin (responsible or the bitter taste) to prunin and rhamnose. There is evi-

dence that thisprocess could be achieved by immobilizing the enzyme on porous glass (Manjón et

al.1985). Another interesting example is given by Hasegawa and Maier (1983). These authors used

a limonoate dehydrogenase fromAcinetobucter to oxidize limonin, a bitter compound of grapefruit

and orange to non-bitter limonoate A-ring lactone and they showed that the process could be greatly

improved by immobilizing the enzyme in acrylamide gel. In the field of alcoholic beverages, the re-

moval of diacetyl from beer has been studied by Tolls etal. 1970). They used a bacterial diacetyl re-

ductase to reduce diacetyl (responsible of unpleasant butter-like note) to2,3 butylene glycol but, al-

though the process was successful, it presented the drawback of requiring great amounts of NADH

cofactor. A different approach exists in the addition of acetolactate decarboxylase to the ferqenta-tion broth at the end of the process. This enzyme allows the direct transformation of a-acetolactic

acid to acetoin avoiding its spontaneous conversion to diacetyl (Cochet 1988). In a more recent re-

port, the gene coding forthisenzyme has already been cloned in Saccharomycescerevisiueused for

brewing, reducing the levelofdiacetyltoless than 0.01ppm(Scott 1989). However, the brewing in-

dustry is very conservative,soit isdifficult to predict if thiskindof strain will reachcommercializa-

tion stage.

Glucose oxidase can be helpful in removing tracesof dissolved oxygen which cause oxidative

rancidity and removing glucose which leads, inturn, o enzymatic browning in processed foods.As

an example, Takenawa et aL(1990) patented a process in which this enzyme is added to hydrated

soybeans in order to reduce the development of oxidation in the preparation of soya milk. Thisen-

zyme has also beenused in processed eggs, dehydrated potatoes andmayonnaise Godfrey and Rei-

chelt 1983).

Another example of enzymatic off-flavor removal is the use of sulphydryloxidase in ultrahigh

temperature ilk. This enzyme oxidizes sulphydryl or thiol groups to disulfides, the former

beingresponsible orthecookedflavorofsterilizedmilk Shipe 976,SwaisgoodandHorton1989).

However, a big limitation is the lack of an abundant source of the enzyme.

Nomura et a¿. 1988,1991) examined the decomposition of hexanal, which causes the off-fla-

vor in food materials, by immobilized acetic acid bacteria and cell-free extract of Baker's yeast. They

.



176 CHRISTENAND LC~PEZ-MUNGUÍA

found that hexanal was converted to either hexanol or hexanoic acid under the action of ADH, alde-

hyde dehydrogenase and the NADH oxidase enzymes. Theyalsoreported its possible application to

reduce off-flavor in deffatted soy milk, since the system was used during sixty cycles without any

loss in enzyme activity. The ADH has also been studieddirectly in foods. Matobaer al. 1990) repor-

tedthe reduction of n-hexanal to n-hexanol in soybean extracts with best results usi@NADH asco-

factor. Hildebrand (1992) reported also that genetic engineering could be an interesting solution t o

indirectly eliminate some off-flavors from food: or example by altering the gene coding for the li-

poxygenases system synthesis thereby stopping the lipoxygenase-catalyzed peroxidation of fatty

acids reponsible for the formation of hexanal.

Finally, an indirect participation of enzymes in the eliminationof off-flavors s the increasing

use of cyclodextrins (CD) in the food industry. Thesearecyclic glucose oligosaccharides containing

6,7or 8 glucose units, prgduced by the enzyme cyclodextrin glycosyl transferasefrom starch. CDs

have been successfully used in the removal of the off-flavor due to naringin and bitter peptides (Psze-

Zola 1988, Korpella etal 1989).

ENZYMATIC SYNTHESISOFFLAVOR COMPOUNDS

One of the important focusses in the flavor ndustry is the biosynthesis, solation and purifica-

tion of individual active chemicalsusing enzymes. Themany advantages of enzymes in biosynthesis

are widely recognized, considering their specificity(enantio and stereo selectivity), he use of mild

reaction conditions and their availability(Sicsic1987). There are parallel efforts in the enzyme re-

search to develop new enzymes through protein engineering (Haas 1984, Leuchtenberger 1992),

new ways of stabilization by immobilization or chemical modification (Shamieral.1989),cofactorregeneration process in redox reactions (Duine 1991 .new strategies suchasextractive bioconver-

sions (Andersson and Hahn-Hagerdal1990) and new properties and specificitiesby the modifica-

tion of the reaction medium (Klibanov 1986,Zaks and Klibanov 1988). In the following section we

will review some examples of flavor compounds that maybe roduced by enzymatic processes, fol-

lowing the already mentioned trends in enzyme technology.

1.Lipases and esterases.

A great deal of research has been directed towards the use of lipid related enzymes - lipases

mainly- (Welsh etal.1989,Yamane 1991) forinvitroflavor synthesis.InFigure 1,the reactions in

this field catalyzed by lipasesareshown. Moreover, special’interest as.been given to ushg organic

solvents as eaction mediabecausein hese conditions, hese hydrolytic enzymes work preferably in

the synthetic way (Klibanov 1986).Recently, Vulfson (1993) reviewed the application of this tech-

nique for food ingredient production.

Ester synthesis by means of lipase is &interesting altemative considering that there aremany

well known flavor esters in the natural aroma of fruits, traditionally obtained by extractionor by

chemical synthesis. The enzymatic synthesis of more than 50esters has been described to date by

Welsh etp_I,( 989). Some of the more recent examples are reported in.Table 3.



ENZYMES A N D FOOD FLAVOR 177

1)Hydrolysis : RCOOR' +H 2 0- COOH +R'OH

2) Esterification: RCOOH +R'OH ___ RCOOR' +H20

3)Transesterification:3.1) Alcoholysis :RCOOR' +R 0H ___ RCOOR +R O H3.2) Acidolysis : RCOOR' +R C 0 0 H ____+ RCOOR R'COOH3.3) Interesterification: COOR' +R COOR '- COOR +R'COOR

4)Lactonization: RCOO-(CH2)n-OH ___+ 8rC1(Intramolecular Esterification)

(CH2)n O

FIGURE 1-Lipase-mediated reactions

TABLE 3- In vitro fiDase-mediated svnthesisof flavor esters.

Substrates

Esterification. -butanol butyric acid. thanol+ oleic acid. eptanoIf oleic acid. thanol +buty ric acid,

aliphatic alcohols and acids. 3-C5 aliphatic alcohols+

acetic or butyric acids

. thanol acetic acid. thanol and n-butanol+butyric acid. 2, C4, 5 alcohols+

C2, C4 acids. erpene alcohols

C2, C3, C4, C6 acids. sopentanol and geraniol

C2-C4 acids.Cl-C6 , terpene alcohols+

C2-C6 acids. thanol fiee fatty acids or

unhydrolyzed butterfat. 5-ClO n-alcoh ols or phenyl-

alkanols dodecanoic acid. utanol +butyric acid

'Ji-ansesterification. thanol or isopropanol

. onanol ethyl propionate

. sopentanol ethyl acetate

. sopentanol or geraniol

. econdary alcohols+

triglycerides

ethyl or isopenty l ac. or but.

vinyl acetate

Lipase source Reaction medium Immobilization Authors

M.miehei

M miehei

C.cylindracea

M.miehei

C. ylindracea

C. ylindraceaA. niger, PPL*C. ylindracea

various (M. miehei.

C. ylindracea...A. niger,R elemar,

G. andidum, ...various A. iger,

M.miehei,...)

various (M. miehei.

R. arrhiws ,...)

C. ylindraceo

PPL*

M miehei

P. fluorescens

C. ylindracea

M.miehei .

various (A. niger,

M. miehei,...)

not given

n-hexaneorganic

n-hexane

n-hexane

n-heptanen-hexane

hexane,.octa-ne, decanewater

n-heptane

n-heptane

water

n-heptane

hexane

excessalcohol

n-hexanen-heptane

not given

no

no

nocelite

no

silica gel0

no

no

no

. no

no

no

no

celite

no

no

no

anionic resin

Borzeix et 01 1992Gatfield 1988Goldberg er al. 1990Manj6n etal:1991

Welsh & Williams 1989

Gillies e t al 1987Welsh &Willi ms 199C

Welsh e t a[.1990

Iwai et al. 1980

Langrand et aL 1988

Langrand et al. 1990

Kanisawa 1983

Gerlach et a1.1989

Borzeix et al.1992

Shaw et 01.1991

Goldberg e t al.1990Rizzi et al.1992Langrand e t al.1988

Holla et al.1990

*PPL : orcine Pancreatic Lipase.




Synthetisyields have been shown to be a function of the hydrophobicity of the solvent (logP), the

source of lipase and the molecularweight of alcohols and acids.In particular,Goldberg er aL(1990)

showed that substratepolarity and water activity greatly nfluence the esterification and transesteri-

ficatiQn ates. Enzyme activity was shown to be highly dependent on the water molecules released

during the esterification eaction, while the transesterificationratewas found to be constant from the

beginning of the reaction (Goldberg et al. 1990). Generally, solventswith logP>3.5 and a water

content of less than 1 are optimal conditions for the synthesis of short-chain flavor esters (Welsh et

al.1989,1990,Manj6n et al. 1991). However, in many cases, enzyme stability n organic solvents is

still a major problem.

Transestenfication (acidolysis or solvolysis) is preferable to esterificationbecause inhibition

by the acid or the alcohol does not occur (Langrand et al.1988, Rizzi et aZ.1992). Moreover, thi3

reaction did not release water molecules and hence, initial water content of the reaction medium is

kept cgnstant (Goldberg et al.1990). This process has been successfully applied by Shaw et

aL(1991) for the solvolysis of triglycerides with long-chain fatty acids for the production of the cor-

responding esters, while Holla etal. 1990)carriedout the transesterification of vinyl acetate for the

resolution of secondary higher alcohols.

As a practical application of estenfication, Kanisawa (1983) produced an ethyl ester mixture

from butterfat oil and Welsh et aL(1989) achieved the synthesis of C3-C5 alcohols from fusel oil,

concluding that controlled hydration of the enzyme increased the efficiency of the systemin terms of

reaction rate. Nevertheless,thisparameter mustbe consideredcarefully: Gillieset al. 1987) pointed

out that hydration of immobilized C. cylindr ce lipase decreased the final ester concentration, al-though the hydrated enzyme wasmore stable after repeated use. In terms of strategy, microaqueous

or biphasic water/solvent systems are preferable to reverse micelles as shown by Boaeix et

aL(1992) with butyl butyrate synthesis as a model.

UedaetaZ.( 1992) studiedthebiosyntheticpathwayofaromaestersinvarious ruitssuchasba-

nana, melon and strawberry. They showed that the production of ethyl, butyl, isobutyl and isoamyl

esters of acetate and butyrate was linked to the activity of an alcohol acyl COA ransferase-or ester

synthetase- extracted from these fruits. They proved that the reactivity of the purified enzyme, em-

ployed in vitro was dependent on its origin and on the substratestructure. For example, the synthe-

tase from banana and melon reacted well with acetyl-COA, propionyl-COA and butyril-COA while

the enzyme from strawberry reacted better with vaIeryI-COA.

L-menthol is one of the most important terpene alcohols widely usedin the perfume and flavor

industry. It is used intoothpaste and many other products for itsmint aste and refreshing sensation.

I t s commonly obtained by isolation and crystallization rompeppermintoilorchemically synthesi-

zed from benzoic acid. However, in thisprocess the limiting stepisthe separation of L-menthol (the

activecompound) from DL-mixtures. There aremany patents dealing with the enzymatic resolution

of the mixture by the specific hydrolysis of DL-menthol esters, L-menthol being then recovered by

crystallization.This process has been successfully achieved with esterasesof Saccharomyces Mo-

roe et al. 1970), bacteria (Moroe-et al.-1971);Alginomonas (Watanabe and hag& 1977, 1979).

More recently, a whole cell process involving the esterase lipase ofRhodotodiYminuta has been

\

- - - - .



ENZYMES A N D FOOD LAVOR 179

described (Omata etal.1981). Moreover, these authors showed that the catalytic activity of the cellswas enhanced because of its entrapment n polyurethane resin gels (estimated half life of more than

55days)yieldingL-mentholoflOO opticalpurity.Theesterificationcanbecarriedoutdirectlyin a

specific process to produce L-menthol-5-phenyl valerate using Candida Cylindracea lipase adsor-

bed onto celite and entrapped in polyurethane (Cheetham 1991). The same selective esterification

may be carried out for the resolution of DL-citronellol (Cheetham 1991) and DL-bomeol mixtures

with esterase of Trichudenna (Oritani and Yamashita 1976).

Enantiomericsecondary alcohols are present in fruits such asblackberry, com, coconut or ba-

nana. As an altemative oute to synthesize hese compounds, lipase enantioselectiveesterifications

have been studied n thelast few years. Janssen etal.( 1991)have shown it was possible to apply this

technique successfullyfor the resolution of secondary alcohols by transesterification n alkyl carbo-

xylatesassolvent. They pointedout that addition of amolecularsieve o the reaction mixture greatly

improved he reaction yield for theresolution of 1-phenylethanol. Another examp e is given by Ger-

lach etal.( 1989)who prepared aliphatics and phenyl alkanols with high chemical and optical yields,

outlining the importance of experimental conditions such as temperature, chain length of the sub-

strate and enzyme immobilization.

Lipase ofMucorspecies has been shown to catalyze the lactonization reaction of 15-hydroxy-

pentadecanoic and 16-hydroxyhexadecanoic acids to the corresponding macrocyclic lactones

(Antczaketal. 1991).Thereaction was achieved in an organic mediumcontaining ether and'ioluene

at80 Cand aconversionyieldofover30%wasreached.The yieldofthisreaction can beincreasedif

free water contentismaintained at0.083% and if sugar alcohols such aserythritol, arabitol or sorbi-

tol are added before lyophilization of the enzyme (Yamane et al. 1990).

2. Oxidoreductases.

Oxidoreductases play major roles in determining the quality of certain food products (Whita-

ker 1984). Nevertheless, very few of them have been used for industrial applications, mainly due to

the difficulties found in the economical production and/or regeneration of cofactors-involved n the

process. There are, however, some examples indicating the potential application of oxidoreducta-

ses, regenerating the cofactor by a second enzymatic reaction, mainly in a membrane reactor where

the cofactor may be retained.

2.1 Alcohol dehvdroeenase (ADH).

Thisenzyme canbeextractedfromhorse liver, plants like the grape (Molina etal.1986, 1987)

or produced by microorganisms.I t s able to workinboth directions, for reducing ketones to alde-

hydes, aldehydes to alcohols or oxidizing alcohols to the corresponding aldehydes. Initially, possi-

ble applications of the ADHwere reported by Ericksson (1975). The relation between the intercon-

version yield of aldehyde to alcohol and the sensorial note obtained was studied, showing that ADH

added with NADH to milk containing polyunsaturated fats could reduce the amountof aldehydes,

particularly hexanal (Erickssoner al.1977). A few years later, Tamaki and Hama (1982) purified

and characterized the ADH from bakers' yeast. This enzyme was found to be active for the oxidation

of a wide range of aldehydes to their corresponding carboxylic acids.



1

180 CHRISTENAND L ~ P E Z - M U N G U Í A

Acetaldehyde plays asignificant role in the flavor of certain fruits ike orange and foods like yo-

gurt. Raymond (1984) patented an enzymatic procedure employing ADH to prdduce acetaldehyde

from ethanol present in orange essence, in which the cofactor NAD is regenerated by use of flavin

mononucleotide (FMN)in a light-catalyzedprocess with oxygen and catalase. Three other different

methods for the production of flavor aldehydes were tested by Legoy et aL(1985). These authors

studied the conversion of geraniol to geranial n a biphasic system (waterhexane) taking advantage

of the difference in solubility of each compound in the organic phase.This system avoids the end

product inhibitory effect allowing conversion yields close o50%. t has been applied successfully to

the production of citronellal, hexanal and 3-phenyl propanal. BowenetaL 1986)used asimilarpro-

cess to study the conversion of cinnamaldehyde to cinnamyl alcohol with an immobilized yeast

ADH.Reducing enzymes (specifically secondary ADH) of acetic acid bacteria were found to trans-

form a great number of ketones to their corresponding alcohols.Best results were found with the en-

zymatic system ofGluconobacteroxydansandAcetobacter acetiireducing 12 ketones to S)- alco-

holswith an enantiomeric excessofmore than 94% (Adlercreutz 1991) while the redox-enzymatic

system of Gluconobacter subuxydanswas found to be able to convert glucose in 5-ketogluconic

acid, which is then convertedby controlledheating into amonomethyl furanone, astrongly meat-fla-

vor molecule (Cheetham 1991).

Braun and Olson (1986) attained he controlledproduction of acetic acid, 3-methyl-butanal and

3-methyl-butanol with cofactor recycling (NAD-NADH) with the reducing enzyme system of Glii-

conobacteroxydansand Streptococcus lactis.The alcohol dehydrogenase and aldehyde dehydro-

genase of G. oxydanswere shown to be able to regenerate NADH and to produce acetic acid fromethanol while the enzymatic system ofS. l c h transaminase, decarboxylase and ADH) was found

to synthesize the aldehyde (with malty flavor and the alcohol from leucine as precursor).

2.2 Alcohol oxidase.

Benzaldehyde is themainmolecule in the cherry fruit flavor and is enzymatically fo.rmed when

the seeds or pits of fruits suchasalmonds, apricots, peaches orapplesarecmshed. The biotechnolo-

gical production of this compound by enzymic oxidation with alcohol oxidase has been studied in

the past few years (Cheetham 1993). Duff andMusay (1989), showeditwaspossible ousethisuni-

directionalenzyme (only oxidation pathway) to produce benzaldehyde from benzyl alcohol. They

developed a two phase whole-cell process, withPichiapastoris, a methylotrophic yeast, using cata-

lase to transform the denaturing H202 produced. The same authors (1990), demonstrated that it was

possible to extend this application to the oxidation of c2 c6aliphatics alcohols to their correspon-

ding aldehydes. Nevertheless,Nikolova and Ward (1992), showed that the whole-cell process gave

higher rates of conversion than cell-free extracts with Saccharomyces cerevisiae. As a novel

concept in bioprocess engineering, Banana et aL(1989) studied the enzymatic oxidation of ethanol

in the gaseous phase with twomicrobial alcohol oxidases.The authors demonstrated he importance

of water activity on both enzyme thermostabilityand activity.- -



ENZYMES AND FOOD FLAVOR

2.3 Glucose dehvdrogenase and aldose reductase.

181

In astrategy of cofactorregeneration by means of coupling two enzymatic reactions, a process

has been developed by the Denki Kagaku Kogyo company to produce gluconic acid, an acidulant,

from glucose using glucose dehydrogenase requiringNADP+, the cofactor s reduced again with the

sihe substrate, glucose, but transformed by the enzyme aldose reductase to sorbitol: the resulting

concentrated syrup has sweet and acid taste (Fukui 1990).

2.4 Other oxidoreductases.

- A dehydrogenase fromPseudomonasputidahas been found to be able to convert L-menthone

into L-menthol (Nakajimaetal.1978). Thisfinding canbe applied to the bioconversion of the essen-

tial oil (containing nearly only L-menthone) of the plantMentha piperita inits immature stage in or-der toincreask the proportion of L-menthol, the active flavoring compound. Mitsui Company has re-

cently reported a similar process using cells of Cellulomonas urbata.In both cases, there is a need

for a cofactor regeneration system. In 1979, Takahashi etal.isolated an aldehyde oxidase from bo-

vine liver and applied it for the reduction of the green beany taste in soybean. The reaction was car-

ried out under aerobic conditions with dissolved oxygen as the electron acceptor, without the need of

cofactor. It is assumed that the loss in the intensity of green note was due to the oxidation of n-penta-

nal and n-hexanal.

Ionones and other related compounds including ß-ionone and ß-damasconearevery important

aroma compounds in tobacco and many fruits, formed by enzymatic degradation of carotenoids.

Sode et aL(1989) have been able to cany out the microbial conversion of ß-ionone using A. niger

cells in organic solvents. However, using enzymes such as polyphenoloxidase, it has been possible

to obtain small amounts of ß-ionone, when acting on substrates ike palm oil rich in carotenoids

(Therre, 1990).

In the field of lactones, Maguire et al. 1991) achieved the reaction of lactonization of the lino-

leic acid employing an immobilized soybean lipoxygenase leading to acl macrocyclic lactone as a

product. Willets et al. 1991), obtained the transformation of endo-bicyclo heptan-2-01s and endo-

bicyclo hept-2-en-6-01 into their corresponding lactones using a coupled enzyme system (dehydro-

genase from Themoanaerobium brockii and monooxygenase fromAcinetobacter calcoaceticus)

with coupled regeneration of NADPH+/NkDP+ cofactor.

As an indirect positive influence on the development of flavor in wine, the action of glucose

oxidase to remove any remaining glucose, transforming it in gluconic acid maybecited (Heresztyn

1987).

Using formate dehydrogenase as he second enzyme for regeneration of NAD, the company

Genzyme produces a wide range of optically active a-hydroxy acids via lactate dehydrogenase as

first enzyme (Dunnet al.1991).In he case of flavor compounds, several enzymes display potential

applications. Magee et al. 1981) produced diacetyl (responsible for butter flavor) and acetoin by

multienzymatic system consisting ofmilk fat coated microencapsulated cell free extracts of Strep-

tococcus lactis. These authors assumed that diacetyl was synthesizedthrough the oxidative path-

? .



182 CHRISTEN AND L6PEZ-MUNGUíA

way involvinglacetyl-CoA, nd acetoin through the a-acetolactate route, both of them by means of

oxidative enzymes.

3. Other enzymes

The major groups of enzymes involved in the productionof flavors are hydrolases or oxidore-

ductases. Nevertheless, other types of biocatalysts canberegarded aspotentialy interesting.This is

the caseof a lyase: the a-terpineol dehydratase catalyzes the reaction of limonene (a by-product of

the citrus ndustry)conversion o a-terpineol, monoterpeneof great interest.This enzyme has been

isolated from Pseudomonas gladioli by Cadwallader er aL(1992). These authors showed that the

isolate was composed of2proteins with apparent molecular weight of 94,500 and 206,500 daltons.

Almosnino and Belin (199 1) solated an enzyme systemfrom apple pomace, able to produce C6-Ciovolatile aldehydes fromlinoleic acid through the action of two main enzymes: lipoxygenasewhich is

reponsible of the formation of hydroperoxides from unsaturatedfatty acids and hydroperoxide yase

which ensures the generation of the volatile aldehydes. They found that the amount of aroma com-

pound could be significantly increased by adding SO2 or vitamin C in the reaction medium.

CONCLUSIONS

Research n the areas of food technology and biotechnologyhas been influenced by the increa-

sing demand of consumers for nutritious ood and natural food ingredients. In this review, the impact

of enzyme technology on flavorhas been examined. Itmust be pointed out that this review mainly

concernsreports in the scientific and technological iterature and shows he trends in research on fla-

vorrelated enzymes. It is helpful1 to add that most of the actual researchis far from the appkation to

the flavor industry. Some potential applications are mentioned and they stillneed further research

and to show economical feasability in order to reach the commercial scale. Other problems encoun-

tered are the production capacity and the enzymes stability. Genetic and protein engineering may

contribute to overcome some of these drawbacks but it is mportant to consider the development

costs including eventual toxicological studies and market sizes.Also, some sectors of the food in-

dustry are regarded as traditional and might not beopened soeasily to the introduction ofnew pro-

ducts or processes.

However, some advantages of enzymatic-cátalyzed synthesis (mild temperature, pressure and

pH conditions,high enantioor regiospecificity, ackof contaminatingby-products) are attractive for

the production offlavorcompounds.Itmaybeconcludedthat theuseofenzymes as additives forfla-

vor production and/or modification may become an important part of enzyme technology as shown

by some recent developments. The better understandingof flavor generation in foods aswell as the

advances n the use of enzymes in non-aqueous media alsqoffersa great potential for this activity in

thenearfuture.Thisis already afact forEMCandin general,forflavorderivedfromdairyproducts.

ACKNOWLEDGMENTS

Authors wish to thankDr S.Revah from theMetropolitan Autonomous U niversity ofMexico for hishelpful comments.



ENZYMESANDFOODFLAVOR 183

REFERENCESAbbott,N.A.,Coombe,B.G. andWilliams,PJ. 1991.Thecontributionofhydrolyzedflavorprecursorsoqualitydiffe-rences in Shiraz uice and wines:An investigationby sensory descriptiveanalysis.Am. J. Enol. Vitic. 42(3): 167-17 4.

Addo,K. urton , D., Stuart,M.R.,Burton, H.R and Hildebrand, D.F. 1993. Soybe an flourlip oxy gen ase isozy me mu-tant effects on bread dough vo latiles.J. ood S i. 58(3): 583485,608.

Adedeji, J., Hartm an, T.G., Lech , J. an d Ho, C.T. 1992. Characteriza tionof glycosidically boudd arom a compounds n. he african mang o Mungifem indicuL ..Amic. Food Chem. 40(4): 659-661.

Adlercreutz,P. 1991.Asymmetricreductionofketoneswithenzymesfrom cetic acidbacteriaBiotechnol. Lett, 13(4):

Almo snino, A.M. and B elin, J.M. 1991. Apple pomace:An nzyme system for producing aroma com pounds fromplyunsaturated fatty acids. Biotechnol. Le& 13(12): 893-898.

Andersson. E. and Hahn -Hagerdal,B. 1990. Biocon versions n aqueous two-phase systems. Enzy me Microb . Tech nol.

Antczak, U., Gora, J., Antczak,T. and Galas . 1991. Enzymatic lactonization of 1 5-hydroxy pentadecano ic nd 16-hydroxyhexadecanoicacids to m acrocyc lic lactones. Enzyme Microb. Technol. 13(7): 589-593.

Arbige, M.V., Freun d, P.R., Silver, S.C. and Ze lko, J.T. 1986. Novel lipase for Ched dar cheese flavor developm ent.FoodTechnol. 40(4): 91-96.

Arnold,RG., Shah ani, K.M. and Dw ivedi, B.K. 1975. Application of lipolytic enzym es to flavor deve lopm ent n dairyproducts.J.Dai? Sci. 58 8): 1127-1143.

Barzana,E., Karel, M. andKlibanov,A.M. 1989.Enzymaticoxidationofethanolinthe gaseous phase. Biotechnol. Bio-

Basset,F. 1990. Arôme s naturels: oui aux biotechnologies.parfums. Cosmetiqueset Arômes. 9 3 (JuinlJuillet): 17-26.

Belford, A.L., Lind say. R.C. and R idley, S.C. 1992. Bound vanillin in maple sap. Flav. Fran. J.7(1): 9-13.

Benaig es, M.D., L6pez -Santin. J. and Sol C. 1990. Produc tionof 5'ribonucleotides by enzy ma tichydrolysis of RNA.Enzvme Microb. Technol,l2(2): 86-89.

Bigelis, R. 1 992. Flavo r metab olites and enzymes from filamentous fungi. Food Tec hnol. 46(10):151-161.

Borgström,B. and B rockm an. H.L. 1984. Lipases. Elsevier Science, Amsterdam.

Borzeix,F.,Monot,F.and vand ecas teele, J.P. 1992. Strategies or enzymatic esterification n orga nicsolvents: Compa-rison of microaqueous. biphasic and micellar systems. Enzvme Microb. TechnoL14(10): 791-797.

Bowen,W.R.,Lambert,N.,Pugh,S.Y.R ndTay1or.F. 1986.Theyeastalcoholdehydrogenasecatalysedconversion fcinnamaldehyde to cinnamy l alcohol. J. Chem. Technol. Biotechnol. 3 6 267-272.

Braun, S.D. an dOls on. N.F. 198 6.Regulating lavor compoundsynthesis nd cofactorrecyclinginheterogeneousenzy-matic reactions by mixturesof b acterial cell-free extracts.J,Daim Sci. 69(5): 1209-1218.

Bruemmer, J.H., Baker, R A . and Ro e, B. 1977. Enzymes affecting flavor and appearance of citrus products. In: En-zvmes n food andbeverapeprocessing,Eds.R.L. OryandAJ.St.Angelo.,A.C.S. ymp. Ser.47,WashingtonD.C..pgs1-11.

Cadwal1ader.K.R. Braddrock, R J . and Parish, M.E. 1992. Isolation of a-terpineol deh ydratase from Pseudom onasgladioli.J. ood Sci. 5 7(1): 241-244.248.

Chase,T. 1974. Flavor enzymes. Adv. Chem. Ser. 1 3 6 241-266.

Cheetham, P.S.J. 1991. The flavour and fragrance industry.h. iotechnolow. The science and the business,Eds.V.Mo ses and R.E. Cape., Ha nvo od Acad., London , pgs 48 1-506.

Cheetham,P.S.J. 1993.Theuse ofbiotransformationsfortheproduction fflavours and hgrances.TrendsBiotechno1,1111 :478-488.

Chen , J.P. andM cGill, S.D. 1992. Enzym atichydro lysis of triglyceridesby Rhizopusdelemurimmobilized onbiomasssupport particles. Food Biotechnol.al): -18.

Chen , J.P. and Pai, H. 1991. Hydroly sis of milk fat with lipase in reversed micelles. J. Fo od Sc i56 (1 ): 234-237.

Cho, J.and Lung, F. 1991. Production of nucleotide by imm obilized cells. Bull. Korean Fish SOC. 4 1 11-1 16.

229-234.

12(4): 242-254.

=. 4: 1178-1185.

'*



184 CHRISTEN AND L6PEZ-MUNGUíA

C oche t, N. 1988. L es enzymes mic robiennes d ~ s'industrie agro-aliment& nouvelles applications. Biofutuc. 67(4):

Cordonnier,RE., Giinata,Y.Z.,Baumes,R.L. andBayon ove, C.L. 1989.Recherched'unmatCrielenzymatiqueadapté

l'hydrolyse de s pr6curseurs da ram e de nature glycosidique du raisin. Connaissance de la viene et du vin. 23( 1 7-23.

Crouzet, J. 1 977. Régénération enzym atique des adm es.

Crouzet, J. 1989. LabiogCnBse des aram es. IIBmes En tretiens d'Am- . .Mon tpellier. FRANC E. 27 Sept. 1 8 pp.

Davide, C L. and Foley. J. 1981. Cheddar-type cheese with coconu t oil and lipase treatment. Philippine A miculturist

Duff, S.J.B. and Murray,W.D. 1989. Oxidation of benzyl alcohol by whole cells ofPi chiu part oris and by alcohol oxi-dase in aqueous and non a queou s reaction media. Biotechnol. Bioeng. 34: 153-159.

Duine, JA . 1991. Cofactor engineering. Trends Bio echnol, 9 343-346.

Dunn, C.R. .Wilks, H.M., H alsall, DJ ., A tkinson,T., Clarke, A.R., Mu irhead, H. and Holbrook, J.J. 1991. Design an dsynthesis of new enz ymes based on lactate dehydrogenase. Phil. Trans. R. Soc.Lond332: 117-184.

Dupin,I iinata, Z., apis, J.C., Bayonove , C., MB aiaraoua,O. and Tapiero, C. 1992. Production of ß -apiosidase byAspergillus niger. partial purification. properties and effect on terpenyl apiosylglucosides from grape. L A e c . Food-40(10): 1886-1891.

Dziezak. J.D. 19 8 6a Biotech nology and flavor development: An industrialresearchperspective.FocdTechnol,40(4):

Dziezak, J.D. 1986b . Biotechn ology and flavor development: Enzym e modification of dairy products. Food Technol,40(4): 114-120.

Dziezak , J.D. 1987. Yea sts and yeast derivatives: Applications. FoodTechn oL 41(2): 122-125-

El-Soda, M A . Hanti ra , A A , Ezzat, N.I. and El-Shafei, H.K. 1992 . Acce lerated ripening of Ras cheese using freeze-shoked mutant strains ofLoctobu cillus cusei.FoodChem,44(3): 179-184.

- .55-56.

8(5): 29-35.

64(1 67-77.

108- 13,120.

Eriksson, C. 197 5. Aromaco mpo unds derived from oxidized lipids. Some biochemical and analytical aspects.J.Aeric,

FoodChem,23(2): 126-128.Eriksson, C., Q vist, I. and Vallentin, K.1977. Conversion of aldehy des in liquid foods by alcoho l dehydrogen ase. In:Enzvmes in food nd bev eraee proces sing, Eds R.L. Ory and A.J. St.Angelo., A.C.S. Symp. Ser. 47, Washi gton D.C.,

Fem bdez -Garcfa , E. 1986. Maduracidn acelerada del queso. Nuevas tendencias. Alimen taci6~. (4): 53-63.

Femb ndez-G arcia, E., Ram os, M., Polo, C., Jufirez, M. and O lano, A. 1988 . Enzym e accelerated ripening of Span ishhard cheese. Food Cheq. 28: 63-80.

Femindez-Garcfa, E..Lopez-Fandino, R,Olano,A. andRamos, M. 1990. Comparative study of the proteolytic activityof a Bucillus subtilis neutral protease preparation during early stages of ripening of cheese made from cow and ewemik Milchwissenschafr. 4 5 0 : 428-431.

Femindez-Garcia, E.. Olano. A., Cabezudo, D., Martin-Alvarez, P.J. and Ramos, M. 1993. Accelerated ripening ofManchego cheese by added commercial enzyme preparation from Aspergillus oryzne. Enzyme M crob. Technol..

Francis, I.L., Sefton, M.A. and William s, P.J. 1992. Sensory descriptive analysis of the aroma of hydrolyzed precurso r

Fukui,S.1990. Recen t topics in research and development of hioreactor systems in Japan. Ann. NewYorkAcad. Sci.

Garcia , H.S., Am und son , C.H. and Hill, C.G. 1991. cha racte rizatio n of the action of an Aspergillus nigerlipase

Gatfield.I.L.1986. Generation of flavor and aroma componen ts by microbial fermentation and enzyme engineeringtechnology. In: Bioeen eration of aromas, Eds. R.Croteau andT. arl im en t A.C.S. Symp. Ser. 317, Wa shington D.C.,pgs 310-322.

Gatfield,LL. 1 988.Production offlavorandaromacompounds bybiotechnology.FoodTechnol,42(10): 110-122,169.

pgs132- 142.

15(6): 519-524.

fractions from Semillon, Chardonnay and Sauvignon blanc grapejuices. J. Sci. Food A mc, 59(4): 511-520.

613: 1-13.

on butteroil emulsions. J. Food S i. 56(5): 1233-1237.



r

ENZYMES AND FOOD FLAVOR 185

Gatfïeld,I.L., Schmidt-Kastner, G . andSand,T. 1983.Immobilizedmyrosinase,itsproductionprocessnduseforpro-ducing natural aromas. German PatentNO 3 312 21 4A l.

Gerlach, D.,Lutz, D..Mey, B. andSch reier,P. 1989.Enantioselectivelipasecatalyzedesterificationin rganicmediumforpreparation of optically active secondary alcohols.Z. ebensm. Unters. Forsch.

Gillies,B..Yama7aki.H. and Ar mstr ong , D.W. 1987. Natura l flavo ur esters: Prod uction by andidaCyrindruceulipaseadsorbed to silica gel. In:Biocatalvsis in oreanic medir\.Eds. C. Laane, J.Tramper and M.D. fi lly , Elsevier Science.Amsterdam, pgs 227-232.

Gcdfrey.T. 990. Enzym e m odifications for bakedgoods and flavour proteins.Fur. Food and Drink Rev, Autumn: 43-48.

Gcdfrey,T.and H awkins, D. 1991. Enzymic modification of fats for flavour. Eur. Food and Drink Rev. Autumn: 103-107.

Godfrey,T. nd Reichelt, J.1983. Industrial enzym ology. The applications of enzymes in industry. Th e Nature Press,New York, N.Y.

Goldberg. M.. T hom as,D. nd Legoy , M.D. 1990. The control of lipase-catalysed transesterification and esterificationrates. Effects of subs trate po larity, water activity and water moleculesonenzyme activity. Eur. JBiochem. 190603-609.

Grosch. W. and Ze.iler-Hilgart,G.1992. Foxmation of mea tlike flavor compou nds. In: Flavor precurso rs, Eds. R. Tera-nishi, G . Takeoka and M. Giintert. A.C.S. S ymp . Ser. 490, Washington D.C., pgs 183-192.

Giinata,Y.Z., Bayonove, C., Cordonnier,RE., maud. A. and Galzy,P.1990. Hydro lysis of grape monoterpe nyl gly-cosides by Cundida molischiunu and Candid a wickerhumii ß-glucosidases. J. Sci. Food Amic, 50(4): 499-506.

Gutierrez,M. yReva h, S. 1993.Aromasy sabores.In:Biotecnolo~íaAlimentariq.Eds.M.Carcfa,R. QuinteroyAL6-pez-Munguía. Limusa, MLxico, pgs 453-478.

Haas, M J. 1984. Meth ods and applications of genetic engineering.Food Technol, 38(2): 69-77.

Hanley. A. B.. Kw iatko wsk a, C.A. and Fenwick, G.R 1990. Enzymic hydrolysis of glucosinolates in a low w ater sys-

tem. J.Sci. Food Aen'c, 51: 417-420.

Hasegawa, S. nd Maier, V.P. 1983. Solutions to the limonin bittemess problem of citrus juices. Fo od T echnol, 37(6):73-77.

Heath, H.B. and Reineccius, G. 986. Flavor chemistry and technology. AVI Book. Van Nostrand Reinhold Co. Pub.New York. 442 Pp.

Heresztyn ,T. 1987. Conversion of glucose to gluconic acid by g lucose oxidase enzyme in Muscat Gordo juice. Au stra-]¡an GraDeerower and Winemaker, 280 5-27.

Herriiz, T. 1990. Produccidn biotecnologica de compuestos del aroma de alimentos. Aplicaci6n a laindustria alimenta-ria. Alim entarh. Junio: 35-39.

Hildebran d, D.F. 1992. Altering fatty acid m etabolism in plants. Food Technol, 46(4): 71-74.

Holla, W., Fiilling , G. and Keller, R 1990.Thepreparation of optically active flavour compoun ds by enz ymatic reac-tions in nonaqueous systems. Food B ote ch no l4( 1): 39.

Huffer,M. andSchreier,P. 1991.Lipase-catalysedtransesterificationn organic solve ntxh epar ation andenantiodiffe-rentiation of optically enriched 4(5>alk ylated 1,4(1,5>olides. Tetrahedron A s y " etry. 2(11): 1157-1164.

Humpf. H U nd Schreier. P. 19 91. Bound aroma compounds from the fruit and the leaves of blac kbe ny Rubus laci-

niatu L ..Amic. Food Cheq. 39(10): 1830-1832.

Iborra,J.L., Castellar, M.R., Cin ova s, M. and Manj6n. A. 1992. Picrocrocin hydrolysis by immo bilized ß-glucosidase.14(6): 475-480.

189 141-143.

Iwai, M., Okumura,S. ndTsu jisaka, Y. 1980. Synthesisofterpene alcohol esters by lipase.&&. Biol. .44(11):

273 1-2732.

Jain, J.C. and Takeo, T. 1984.The enz ymes of tea and their role in tea making. J.Food B i o c h m 8(4): 243-279.

Janssen, A.J.M., Klunde r. A.J.H. and Zwanenb urg, B. 1991. Resolution of secondary alcohols by enzy me-catalyze dtransesterification in alkyl c arboxylates as the solvent. Tetrahedroq. 47(36): 7645-7662 .



,

186 CHRISTENAND L ~ P E Z - M U N G U Í A

Janssens, L. de Poo ter, H.L., Scham p,N.M . and Vandam me, E.I. 1992. Production of flavours by microorganism s.&cess Biochem,27(4): 195-215. ’

Jenniskens,L.H.D.,Voragen,A.G.J., Pilnik,W. andPosthumus,M.A. 1991. Effecb’of the reatment of apple pulp withliquefying enzym es on the aroma of apple juice. T ebe nm . Wiss. Technol. 24: 86-92.

Josephson, D.B. arid Lindsa y,RC. 1986. Enzymic generationof volatile aroma compounds from frdsh fish.In:-nerabon of aromas. ds. R Croteau and T: Parli men t A.C.S. Symp. Ser. 317, Washington D.C.. pgs 201-219.

Kanisawa,T. 1983. Studieso n heproduction offlavours by biochemicalmethods.II.Production ofethyl estermixturefrom butter fat by Candidacylindrucea lipase. Pippm Shokuhin Kowo Gakkai-Shi. 30(10): 572-578.

Kempler, G.M. 1983. Production of flavor compounds by &roorgan isms. A l . 9: 29-51.

Kilara, A. 198 5a. Enzyme-mod ified lipid food ngredients. Process Biochem. 20(2): 35-45.

%la& A. 1985b. Enzyme-modified protein food ingredients. Process B whem . 2 q5) : 149-157.

Kilara,A.andIya, K.K. 1 9 8 5 . P r o t e o l y ti c e n z y m e s a n d t h e i r a p p l i c a t i o n s i n th e d a i ~ i n d u s t r y : ~ ~ 3 8 ( 1 ) :70-85.

Kinsella.J. and H wan g, D.H. 1976. Enzym es of Penicillium roqueforti involved in thebiosynthesis of chee se flavor.Cnt. Rev. Food [email protected](2): 191-228.

Klibanov, M.A. 1986. Enzym es that work in organic solvent. Chemtech, 1 6 354-359.

Knorr. D. 19 87. Biotechnologicalprocesses in food production. FoodBiotechnol, l(2): 225-248.

Knorr,D..Beaumont,M.D.. Ca ster , C.S., Dö me nb Gg , H:, Gross,B., Pandy a,Y. and Romagno1i.L.G. 1990. Pla nt tiss ueculture for the prod uction of naturally derived food ingredien ts.FoodT chnoL 44 6): 1-79.

, . . .

’

Korpella, T., Mattsso n,P..Hellman, J. Paavilainen.S. nd M akela, M. 1989. Cyclodextrins: production. properties andapplications in food chem istry. FoodBiotechnoL 2(2): 199-210.

Krammer. G.. Winterhalter,P., Schw ab,M. and Schreier.P. 1991. Glycosidically bound aroma compounds n the ruitsof Prunusspp.: apricot PrunusanneniacaL),peach (Prunuspersicu L),yellow plum Prunusdomestica ssp. syria-Ca).J.Amic. Food Ch m. 39(4): 778-781.

Kunz, B.. Ru tdof f,H.. Rothe M., Leuchtenberger, A., Qu ehl, A., E ngst, W., Birnbaum, A. and Henmann, H. 1984.Technique for producing aroma substancesby a combined enzymidm icrobial process. German Patent N” 208 54 5.

Langrand. G., Rondot, N., Triantaphylides,C. and Baratti,J.1990. Short chain flavour esters synthesis by m icrobial lipases. Biotech nol. Lett, 12(8): 581-586.

Langrand, G., Triantaphylides,C. and Baratti, J 1988. Lipase ca talysed formation of flavour esters. Biotechnol. Lett,IO(8): 549-554.

Law,B.A. 1984.Microorganismsand their enzymes in the maturation of cheeses. In: ao m e ss in industrial micro biolo-gy,Ed. M.E. Bus hell, Elsev ier Scien ce, Amsterdam, pgs 245-283.

Lego y, M.D., K im. H.S. a d homas D. 1985.Useof alco hol dehydrogenase for flavour aldehyde production. Process

Biocheq. 2 0 145-148.

Leuchtenberger, A. 1992. Ap plication of genetic and gene tic-engin eeringmethods to theproduction of ood and foodadditives. Acta Biotechnd. 12(1): 57-65

Liener, I. 1987. D etoxifying enzymes. In: FoodB i o t e c h n o l o u Eds. R.D. King and P.SI. Cheetham, Elsevier A pplied Science , Lon don, 249-272.

Lindsay, R.C. and Rippe , J K 1986.Enzymatic g eneratio n of methanethiol to assist in the lavor development of Ched -darcheeseandotherfoods.In:Bioeeneration ofaromas. Eds.R CroteauandT. arl im en t A.C.S. Sym p. Ser . 3 17.Was-hington D.C., p gs 286-308.

Luck,T.andHagg, U. 1991. Kinetics 0fthelipase-catalyzedhydrolysisoffatinfermentationbroths.FettWissen.Tech-

Luning, P.A., Roo zen, J.P., Mo est, R.A.F. and Posthum us, M.A. 1991 . Volatile composition of white bread using en-zyme active soya flour as improver. Emd Chem. 41: 81-91

Macrae, A.R,1983 . Extracellularmicrobial ipases.In: Micro bial enzvmes and biotechnolegy, Ed. W.M. Fogarty,Ap-plied Science, London, pgs 225-250.

d 3(4): 141-144.



ENZYMESANDFOODFLAVOR 187

Magee.E.L., Olson,N.F. andLindsay,RC. 1981.Microencapsulationofcheeseripeningsystems:production ofdiace-tyl and acetoin in ch eese by encapsulated bacterial c el l-h e extract.J.Daim Sci. 64(4): 616-621.

Maguire. N.M.. Mahon,M.F.,Molloy,KC.. ead, G..Roberts,S.M. and Sik, V. 1991. Chemoenzym atic synthesis ofsome m acrocyclic C-13 lactones.J. Chem. Soc P a k a . . 8: 2054-2056.

.Manj6 n,A.,Ba stida. J..Romero.C.. Jimen0.A. and Ibo rra,J .L.1985.Immobilizationofnaringinaseonglycophase-CO-ated porous glass.Biotechnol- 7(7): 477-482.

Manj6n. A., Iborra,J.L. andArocas A. 1991. Short-chain flavour ester synthesis by im mob ilized ipase in o rganicme-dia. Biotechnol. Le& 13(5): 339-344.

Marlatt, C., Ho, C.T. and Chien , M. 1992. Studie s of aromaconstituents bound as glycosides in tomato. JJpYic Food

Matoba,T.. Sakurai,A., Tanik oni, N., Saitoh,T.. Kariya,F., Kuw ahata, M., Yuk awa , N., Fujino ,S. nd Hasegawa, K.1989. N-hexanol form ation from n-hexanal by enzyme action in soybean extracts. J. Food S i. 54(6): 1607-1610.

Mermelstein. N.H. 1989 . Con tinuous fermentorproduces natural flavor enhancers for foodsand pet foods. Food Tech-

Molina,I., Nicolas, M. and Crouzet, J. 1986. Grape alcohol dehydrogenase. I. Isolation and characterization.Enol. Vitic, 37(3): 169-173.

Molina, I., Salles, C., Nic olas,M. nd Crouzet, J. 1987.Grape alcohol dehydrogenase.II.Kin etic studies: Mechanism,substrate and coen zyme spec ificity. Am. J. E nol. Vitic. 38(1): 60-64.

Moroe,T.,Hattori,S., K0matsu.A. andYamaguchi.Y. 1971.BiochemicalisolationofL-menthol. erman PatenfN’2036 875.

Moroe,T., Komatsu, A.,Hattori. S. andYamag uchi,Y. 1970.Biochemical separation ofl m en th ol . German Patent NC1 958 587.

Muir, D.D.. Banks, J.M. andHunter.E.A. 1992. Sensory changes during maturation of fat-red uced Chedd ar cheese: Ef-fect of addition of en zymically active attenuatedstarter cultures. Milchw issenschaft. 47(4): 218-222 .

Murray , W.D. and Duff, S.J.B. 990. Bio-oxidation of aliphatic and aromatic high m olecular w eight alco hols byPichia

iotechnd. 33:202-205.astoris alcohol oxidase.Bppl. Microbiol. B

Nag0dawithana.T. 1992. Yeas t- derived flavorsand flavorenhancers andtheirprobablemo deofaction.

Nakajima,O., E y e , R. nd Hayashi,T . 1978. Conversion of L-menthone by Pseudomonnsputzifustrain YK-2. Meta-bolic intermed iateand stereochemiocal structureof the metabolicproducts. Nippon Noe ikaFaku Kaishi.52: 167-174.

Naka0.Y. 1979.Microbialprcduction fnucleosidesandnucleotides.ln:Microbial echnoloev,Eds. H. PepplerandD .Perlman., Acad. Press., N ew Y ork, N.Y. pgs 311-354.

b 0(2): 249-252.

&.43(7): 50-53.

~

. .

(46)ll: 138-144.

Nelson, J.H. 1972. Enzyma tically produced flav ors for fatty systems. J.Am Oil. Chem. Soc 4 9 559-561.

Niko1ova.P. and Wa rd, O.P. 1992 .Redu ctive biotransformation by wild type nd mutant strain s of Saccharom ycesce-revisine in a que ous- orga nk solve nt biphasic systems. Biotechnol. Bioe rg, 39(8): 870-876.

Nomura,Y., Sugisawa,K Adachi,O. and Ameyam a, M. 1988. Reductionofoff-flavor in liduìd foo ds with imm obili-zed acetic acid bacteria.&p- 62(2): 143-148.

Nomura,Y..Ko ma tani, Y., Yamam0to.M.and Sugisawa, K. 1991. Elimination of hexanal by a cel l f ree extract of ba-

Olmedo,F..Ih~rbe,F., G6mez-Hernandez. J. andL6pez-Mungufa,A. 1994. Continuou sprodu ction o f 5’ribonucleotidefromyeast RNA by hydrolysiswt immobilized5phosphodiesteraseand S’adenylate de amina se.World 3,Microbiol.Bjotechnol.lO(1): 36-40.

Omata, T.. Iwam oto, N., Kimura, T., Tanaka, A. andFukui,S.1981. Stereoselec tivehydrolysis of DL-menthyl succi-nate by gel-entrappe dRhodotorulnminuta var. texe nsis cellsi n organic solvent.&pl. Micro biol. Biotech nol. 11: 199-204.

Oritani, T.and Yamashita, . 1976. Optical separation of terpene alcohol by microbe. Jap . Pa tent No 76 35491.

Pabst, A., Barron, D. EtiEvant, P. nd Schre ier, P. 1991. Studies on the enzy matic hydro lysis of bound aroma cons ti-tuents from raspbeny h i t pulp. J.Amic, Food Ch m. 39(1): 173-175.

ker‘s yeast. Hippen Noeeikaeaku Kaishi, 65(6): 993-996.

t



188 CHRISTEN A N D L6PEZ-MUNGUíA

Panne1.L.K. andO lson,N .F. 199 la:M ethyl ketone produc tion nmilk-fat-coatedmicrocapsules:1.Variation of lipaseand spore concentrations.J.Daim Sci. 74(7): 2048-2053.

P kne l , L.K. and O lson, N.F. 199 lb. Methyl ketone production in milk-fat-coated microcapsules: 2. Me thyl ketonesfrom controlled concentrationsof free fatty acids.JDair v S ci. 74(7): 2054-2059.

Pouget.M.P..Pourrat, A. qndP0urrat.H. 1990. Recov ery offlav or enhanc ers rom vanilla podr esidue sby fermentation. ’

Lebbe nsmitt. Wissen ; Techno l, 23(1): 123.

Pszezola, D.E. 1988. Production and potential food applications of cyclodextrins.FoodTechno l. 42(1): 96-100.

Rabie, A.M. 198 9. Acceleration of blue cheese ripening by cheese slurry q d xtracellularenzymes of Penicillium ro-queforti.l~ .9(4): 305-314.

Raym ond, W.R. 1984. Proce ss for the generation of ace taldehyde from ethanol.VS Paten tN”4 481 292.

Reimerd es, E.H. 1984. Proce ss for producing aroma-co ntaining food products. US Patent N’4 432 997.

Revah, S. and L ebea ult, J.M. 1989. Accelerated prqduction of blue cheese flavors by ferm entation on granularcurds

with lipase additio n. 69: 281-289.Rizzi,M..Stylos,P.,Riek,A. andReuss,M. 1992.Akineticstudyofimmobilizedlipasecatalysingthesynthesis fisoa-my1 acetate by transesterification in n-hexane. Enzvm e Microb. Techn ol. 14(10): 709-714.

Rosi, I., Con tini, M. and Bertuccioli, M. 1989. Relatio nshipbetween activitiesofwine yeasts and aromaco mpou nd for-mation. In: Flavors and off-flavors,Ed. G. Charalambous, Elsevier Sc ience, Amsterdam. pgs103-120.

Salles, C., Jallage as, J.C.,Fournier,F.,Tab et, J.C;andCro uzet, J.C. 1991.Apricot glycosidicallybound volatilecompo-nents. J, Azric; Food Chem . 39(11): 1979-1983.

Schindler,J. and Schm id, R.D. 1982. Fragra nce and arom a chemicals. Microbial synthesis and enzymatic transform a-tion. A review. Process Biochem. 17(5): 2-8.

Schreier, P. 1985. Some aspects ofbiocataly sis in natural products chemistry. In: Tou ics in flav ourre search ,Eds. R.G.Berger, S.Nitz and P. Schreier,H. ichhom. W est Germany, pgs 353-369.

Schwab, W., Mahr, C. nd Schreier,P. 1989. Studie son the enzym ic hydrolysisof bound aroma components from Cu-

ricupupuyu fruit.J.Aeric. FoodChen. 37(4): 1009-1012.

Schwab, W. and Schreier,P. 1988. Simultaneo usEnzyme CatalysisExtraction:a versatile ech nique or the study offla-vor precursors. J. A ~r ic . ood chem, 36(6): 1238-1242.

Schwimmer, S.1981. Sou rce book of food enzym ology. AVI, Westport. Connecticut.

. .’ . ?’

. .

Scott,D. 989. Specialityenzym es and products for the food industry. In: Biocatalvsts n avricultural biotechnoloev,Eds. J.R. W hita ker and P.E. Son net, A.C.S. Sym p. Ser. 389, Wash ingto n D.C., pgs 176-192.

Sefton , M.A. and W illiams, P.J. 1991. Generation of oxidation artifacts during the hydrolysis-of nonsop renoid gly co-sides by fun gal enzym e preparations.J. A s k . Food Chem. 39(1l): 1994-1997.

Seitz, E.W. 1990. Micro bial and enzym e-induced flavo rs in dairy foods. J. Dairv Sci. 73: 3664-3 691.

Shami,E.Y., Roth stein , A. and Ram jeesin gh,M. 1989. Stabiliza tionof biologically activeproteins. Trends Biotechnol.7: 186-190.

Sharpell,F.H. 1983.Mic robial flavors and fragrances . In: Co mureh ensiveBiotechnoloyy,Ed.M. Moo-Young,Perga-mon Press , Toronto,V ol.3, pgs 965-981.

Shaw, J.F., Wang,D.L. and Wang , Y. J. 1991. Lipase-catalysed ethanolysis and isopropa nolysis of triglyc erides withlong-chain fatty a cids. Enzvme Microb . Techno l. 13(7): 544-546.

Shoseyov.O., Chet, I.,Bravdo, B. andlka n,R 1988. Flavor and fragranceenhancingenzymes.Fur.PatentN”0 307 071.

Sicsic,S. 1987. Enzym es et chimie fine.La Recherche. 18(188): 626-630.

Sode,K., Karube, I.,Araki R andMikam i,Y. 1989. Microbialconversion of ßionone by immobilizedAspergillusni-

ger in the presenc e of an organ ic solvent. Biotechnol. Bioene. 33:1191-1195.

Spinnler, E. 1 989. Arames: Mo tivations pou r l’emploi des outils biologiques. Biofutur, 68(6): 24-28.

Suarez, M., Du que, C., W intoch, H. and Schre ier, P. 199 1. Glycosid icallybound aroma compounds from the pulp andthe peelings of lulo fruit (Solanum vestissum D.).J.A r i c . Food Chem. 39(9): 1643-1645.

’ :



ENZYMESANDFOODFLAVOR. .

189

. .

..

Swaisgo cd, H.E. and Horton, H.R. 1989. Imm obilized enzymes asprocessing aids oranalytical tools. In: Bioc atalvstsjn amicultural biotechnoloev, E&. J.R.Wh itake rand P.E. Sonnet, A.C.S. Symp. Ser. 389, Washington D.C., pgs 242-261.

Takahashi,N.. Sasaki,R and Chiba.H. 1979.Enzym atic improvment of food flav0r.W . Oxid ation of aldehydes in soy-bean extracts by aldehyd e oxidase . 43(12): 2557-2561.

Takenawa, S.,Takeda,H. andHonk0shi.M. 1990.Processforeliminatingdisagreeableodor rom soyamilk.USPatent

Tama ki, N. and Hama, T. 1982. Aldehy de de hydrog enase from bakers' yeast. Methods Enzymol, 8 9 469-473.

Therre,H. 1990. Les arômes: chassez le naturel...Biofutu r. 69(6): 51-55.

Tolls.TN., Shovers,J Sandine , W.E. andElliker. P .R 1970. Enzymatic emoval of diacetyl from beer. II: Further stu-dies on the useof diacetyl reductase . A ppl. Microb iol, 19(4): 649-657.

Torres, N. and Ch andan , R.C. 1981. Flavor and texture development in Latin American white cheese. J.Dairv Sci,

Tyrrel1,M.H. 1990. Evolution of n atural flavor development with the assistance ofmod em tech nologies. Foo dTe chn ol.

Ueda,Y.,Tsuda, A., Bai, J.H.,Fujishita,N. and cha chi n, K. 992. Characteristic pattem of arom aes ter formation frombanana.melon andstrawbemywithreferen ce to the substratespe cificityofestersynth etase and alcohol contents in pulp.NiDpon Shokuhin Koevo Gakkaishi. 39(2): 183-187.

Vas sero t, Y., C hristiaens , H.. C hem ardin ,P.Arnaud , A. and Galzy, P. 1989. Purification and prop erties of a ß-glucosi-dase of Hunseniosporu vim e (Van d er Walt andT scheusc hner) with the view to its utilization in fruit arom a liberation.J.Apd. Bacteriol. 66(4): 271-279.

Vulfson, E.N. 1993. Enzym atic synthesis offoo d ingredients in low-water media. Trends Food Sci.Technol,4(7): 209-215.

Watanabe. Y. and Inagaki, T. 19 77. Large scale biochemical production of L-menthol. Jan. Patent N D 7 122 690.

Watan abe, Y. and Inagaki,T. 1979 . Optical division of racemic menthol and iso-pulegol. NO7 9 101 487.

Weir, G.S.D. 1986. Protein hydrolyzatesas flav0uring s.h: Developments in food. ofeing Ed. B.J.F. Hudso n ,Elsev ierApplied Science, London, 4:175-217.

Welsh, F.W., Murray, W.D. and W illiams, R.E. 1989. Microbiological and enzymatic produc tion of flav or and fra -grance chemicals. Crit. Rev. Biotechno l. 9(2): 105-169.

We1sh.F. W. and W illiam s, R.E. 1989. Lipa se mediated production of flavor and fragrance ester s from fusel oil.J&d

Welsh,F.W. and W illiams, R.E. 1990. Lipase-med iated production of ethyl butyrate and butyl butyrate in no naqueo ussystems. Enzvme Microb. Technol. 12(10): 743-748.

We1sh.F. W., W illiams, R E . andD aw son , K.H.1990.Lipasem ediated synthesis of low molecu larweight flavor esters.J,Food Sci. 55 (6): 1679-1682.

West, S.I. 1988. Lipase - a new chemical catalyst. Specialitv Cheq . 8 5): 410,414.

Whitaker, J R. 1976. Developm ent of flavor, odor and pungency in onion and garlic. Adv. Food. Res, 22 3-133.

Whitak er, J.R. 1984. Mec hanism s ofoxidoreduc tases impo rtant in foodcomponentmodification.FoodTechnolL38 3):49.

Whitak er, J.R. and Evan s, D.A. 1987. Plant biotechnology and the production of flavor compo unds. Food Technol.41(9): 86-101.

Whitaker, J R. 1990. New and future usesof enzy mes in food processing. Food Biotechn ol, 4(2): 669-69 8.

Williams, PJ.. Sefton, M.A. and Francis.L. 1992. Glycosidic precursors of varietal grape and w ine flavor. In: ?&XQSprecursors, E&. R. Teranishi, G. Takeok a and M. Giinte rt. A.C.S. Symp. Ser. 490, Washington D.C., pgs74-86.

Wille ts, A.J.. K nowles, C.J., Levitt,M.S.. Rob erts, SM..Sandey.H. ndShip ston, N.F. 1991. Biotransform ation o f en-do-b icyc lo (2.2.1) heptan-2-01s and endo -bicy clo (3.2.0) hep t-Zen -6-01nto the corresponding actones. J chem. Soc,

PerkinTrans. , 6: 1608-1610.

* N 4929451.

64(11): 2161-2169.

44 1): 68-72.

L_

&. 54 (6): 1565-1568.




Wintoch,H.. Krammer,G.andSchreier,P. 1991.Glycosidallyboundaromacompoundsfromtwostrawbenyfruitspe-

Yamane, T. Ichiryu.T., Nagata,M., Ueno. A. andShimizu,S.1990. Intmmolecularesterificationby lipase powder inmicroaqueous benzene: Factors affectingactivity of pure enzyme. Biotechnol. BioenG 3 6 1063-1069 .

Yamane, T. 991. Reactions catalyzedby lipid-related enzymes. J. an. Oil Chem. Sw. q10 : 965-973.

Yas;yuki,M.,Yoshinori, K.,Mitsugi, ICYoshiki,Y.Toshio,T.,Fumio,HandHiroshi,N. 1989.Manufactureofseaso-ning materials using imm obilized glutaminase.Japan Kokai TokkyoKoho JP (Ja?. Pateno O1 10,957.

Zaks,A. and Klibanov, A.M. 1988. Enzymatic catalysis n non-aqueous solvents.JChen 63: 3194-3201.

cies,Fragariavexa semperjlorensandFragaria x ananassa, cv. Korona Rav, Frae. L.6 209-215.

food flavor review

Documents

Transcript of food flavor review