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Comparative analysis of caffeine, theobromine and theophyline 
in food and drinks by MEKC and HPLC
Rade Injac
1
, Branislava Srdjenovic
2
, Matevz Prijatelj
3
, Marija Boskovic
4
, Nevena Grujic
2
, 
Borut Strukelj
1
, Biljana Govedarica
2
, Natasa Radic
2
, Zika Lepojevic
5
1
Faculty of Pharmacy, Institute of Pharmaceutical Biology, University of Ljubljana, Askerceva 7, 1000 Ljubljana, Slovenia
2
Medical Faculty, Department of Pharmacy, University of Novi Sad, Hajduk Veljkova 3, 21000 Novi Sad, Serbia
3
Faculty of Pharmacy, Institute of Pharmacy, University of Ljubljana, Askerceva 7, 1000 Ljubljana, Slovenia
4
Faculty of Pharmacy, Institute of Pharmacokinetics and Biopharmaceutics, 
University of Ljubljana, Askerceva 7, 1000 Ljubljana, Slovenia
5
Faculty of Technology, University of Novi Sad, Cara Lazara 1, 21000 Novi Sad, Serbia
Caffeine is the world’s most popular drug. Coffee began to be popular in Europe in the 17th century. By the
18th century plantations had been established in Indonesia and the West Indies. Today, caffeine could be found in
different food and drinks, alone or with associated compounds.
A rapid and selective micellar electrokinetic capillary chromatography (MEKC) and high performance liquid
chromatograpy (HPLC) methods have been developed for the separation and determination of caffeine, theobromine
and theophyline in corresponding real samples of food and drinks. The separation was carried out at 25°C and 25 kV,
using a 25 mM borate buffer (pH 9.0), 50 mM sodium dodecyl sulfate (SDS) and 10% (v/v) methanol, for MEKC,
and on a Zorbax C8 column (4.6 mm x 150 mm, i.d., 5 µm particle size) at 25°C, with a mobile phase of THF (0.1%
in water, pH 8) – acetonitrile (90:10, v/v) with flow rate of 0.8 ml/min, for HPLC. UV detection was at 210 and 273 nm
for MEKC and HPLC, respectively.
The methods were shown to be specific, accurate (recoveries were > 97.1%), linear over the tested range
(correlation coefficients > 0.999) and precise (RSD below 2.1%), for both methods. The within- and between-day
precision was determined for both retention times and peak area. 
Data suggested that the proposed MEKC and HPLC methods could be used for routine quality control of
food and drinks. The advantage of MEKC over HPLC method is in its lower running costs and higher environmen-
tal acceptability. 
Macedonian pharmaceutical bulletin 53 (1,2) 327 (2007)
PP - 168
327
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Viability of Lactobacillus casei in fermented soymilk 
after drying and storage
T. Petreska
1
, K. Mladenovska
1
, L. Acevska
1
, M. J. Pavlova
2
, M. Petrovska
2
, L. Petrusevska-Tozi
1
1
Faculty of Pharmacy, Vodnjanska 17, 1000, Skopje; 
2
Faculty of Medicine, Vodnjanska 19, 1000 Skopje, University "Ss. Cyril and Methodious", Skopje, Macedonia
Soymilk is a water extract of soybean that can provide a plentiful and inexpensive supply of proteins and
calories. However, the presence of indigestible oligosaccharides and the raw bean flavour have limited the wide con-
sumptions of soymilk and other soybean products. It was observed that soymilk could support the growth of vari-
ous probiotics and significantly higher reduction in the contents of stachyose and raffinose was found in soymilk
fermented with cultures of lactic acid bacteria. These observations suggested the possibility and the potential of
developing the lactic acid bacteria-containing probiotic soymilk dietary adjunct. Lactobacillus casei has been report-
ed to exert beneficial effects including the reduction of serum cholesterol, activation of the immune system and inhi-
bition of the growth of potential pathogens that may cause infections disease in the host. 
Because a fluid product usually has limited shelf-life and occupies large volume, and the microorganism is
less stable in fluid than dried product, an attempt was made to dehydrate the soymilk with freeze-drying which is
commonly employed in food industry. Survival of L. casei during the drying process and the effect of cryoprotec-
tant in preserving probiotic's viability were investigated. In addition, the viability of this probiotic microorganism in
the dried soymilk under different storage conditions during 5 weeks was compared in the present study.
When probiotic soymilk drink was prepared, 100 ml of sterile soymilk (SoVita, Vitalia, Macedonia) was
inoculated with 0.05 g/L of L. casei (Chr. Hansen, Denmark), fermented for 3 days at 25
o
C and subjected to freeze-
drying. The fermented soymilk was first poured into a fast-freeze flask (100 ml) and frozen at -20
o
C. The frozen
samples were than lyophilized with a freeze-dryer (Labconco, USA) at a condenser temperature of -45
o
C and 0.180
mBar for about 50 h. The freeze-dried samples were placed in a 100 ml glass bottle, which was vacuum sealed before
storage. They were than held at either 25 or 4
o
C for a period of 4 weeks. The viability of L. casei, moisture content,
pH (pH electrode and meter, Jenway ltd., Felsted, UK) and titratable acidity were measured at predetermined time
intervals in comparison with non-freeze-dried soymilk stored under same conditions. Titratable acidity, expressed
as percent of lactic acid, was determined by an end point titration using 0.1N sodium hydroxide and phenolphthalein
as a colour indicator. For the enumeration of L. casei, MRS broth (Merck KGaA, Darmstadt, Germany) was used.
When the enumeration of bacteria was performed, 1 g of the dried soymilk or 1 ml of the liquid soymilk sample was
mixed with 9.0 ml of peptone water, vortexed for 15 s and serially diluted with peptone water. After 72 h of incuba-
tion at 37
o
C, the colonies that appeared on the plates were counted and the CFU per ml was calculated. The same
procedure and analysis was applied to freeze-dried samples of soymilk prepared with cryoprotectant sorbitol added
in the phase of fermentation (2.5 %w/v). 
Under the drying conditions tested, moisture content ranging from 5.6-7.2% was determined. After freeze-
drying, L. casei exhibited a higher survival percent in respect to non-freeze-dried soymilk sample. Presence of sor-
bitol increased survival of L. casei immediately after freeze-drying and during the investigated storage period. A
higher percent of survival was also noted when the dried soymilk was stored for 4 weeks at 4
o
C than 25
o
C. Values
for pH and titratable acidity ranging from 6.82 and 0.073% l.a. for samples with probiotic only and 6.74 and 0.073
l.a. for samples with probiotic and sorbitol, respectively for the non-freeze-dried samples were determined, while
immediately after freeze-drying the corresponding values were 6.92 and 0.058% l.a. for samples without sorbitol
and 6.85 and 0.07% l.a. for samples with sorbitol, respectively. During storage at 4
o
C for 5 weeks, pH values and
titratable acidity of 3.40 / 0.074% l.a. for samples without sorbitol and 3.69 / 0.50% l.a. for samples with sorbitol
were determined. The corresponding values during storage period at 25
o
C were 3.08 /1.32% l.a. and 2.98 / 1.40 %
l.a., respectively.
In conclusion, freeze-drying of fermented probiotic soymilk in a presence of sorbitol preserves probiotc via-
bility. It is recommended the freeze-dried soymilk to be stored at low temperature of 4
o
Macedonian pharmaceutical bulletin 53 (1,2) 328-329 (2007)
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Vitalnost na Lactobacillus casei vo fermentirano soja mleko vo
uslovi na su{ewe i ~uvawe
T. Petreska
1
, K. Mladenovska
1
, L. Acevska
1
, M. J. Pavlova
2
, M. Petrovska
2
, L. Petru{evska-Tozi
1
1
Farmacevtski Fakultet, Vodwanska 17, 1000, Skopje; 
2
Medicinski Fakultet, Vodwanska 19, 1000 Skopje, Univerzitet "Sv. Kiril i Metodij", Skopje, Makedonija
Mlekoto od soja pretstavuva voden ekstrakt od plodovi na soja i ekonomi~en izvor na mnogubro-
jni biolo{ki vredni proteini. Me|utoa, {irokata upotreba na proizvodite od soja e ograni~ena poradi
nesvarlivite oligosaharidi i oporiot vkus. Mlekoto od soja e pogodna sredina za rast na razli~ni pro-
biotici, za {to govori i zna~itelno namalenoto koli~estvo na oligosaharidite, stahioza i rafinoza vo
fermentirano soja mleko so kulturi na mle~no-kiseli bakterii. Ovoj podatok ja poddr`uva mo`nosta za
proizvodstvo na soja mleko so probiotici od familijata laktobacili. Lactobacillus casei deluva povolno
taka {to go namaluva serumskiot holesterol, ja stimulira imunata funkcija i deluva inhibitorno na ras-
tot na potencijalnite patogeni za doma}inot. 
Poradi ograni~eniot rok na upotreba, pogolemiot volumen i nestabilnosta na mikroorganizmite
vo te~ni proizvodi, soja mleko so L. Casei e podlo`eno na su{ewe so liofilizacija. Vo ovoj trud, sledena
e i sporeduvana vitalnosta na L. casei za vreme i po su{ewe vo razli~ni uslovi na ~uvawe vo tek na 4 nedeli.
So cel da se odredi potencijalot na krioprotekantot sorbitol da ja zgolemi vitalnosta i stabilnosta na
probiotikot vo uslovi an su{ewe i ~uvawe, podgotveni se i ~uvani pod istite uslovi primeroci na soja
mleko so L. casei vo koi vo fazata na fermentacija e dodaden sorbitol  (2.5 % m/v).   
Za podgotovka na liofiliziranoto soja mleko so probiotik, sterilno mleko od soja (SoVita,
Vitalija, Makedonija) be{e inokulirano so L. casei (0.05 g/L) (Chr. Hansen, Denmark) i ostaveno da fermen-
tira 3 dena na 25
o
C. Fermentiranoto soja mleko be{e zamrznato na -20 
o
C i potoa liofilizirano (freeze-
dryer, Labconco, USA) na temperatura od -45
o
C i pritisok od 0.180 mBar vo vreme od 50 ~asa. Liofiliziranite
primeroci, smesteni vo vakumirani stakleni fla{i od 100 ml, bea ~uvani na 25 
o
C i 4
o
C vo tek na 4 nedeli.
Vo ovoj period, ispituvani se periodi~no vitalnosta na L. casei, koli~estvoto na vlaga, pH (pH electrode and
meter, Jenway ltd., Felsted, UK) i titraciskiot aciditet i sporeduvani so soodvetnite parametri na neliofil-
izirani primeroci ~uvani pod isti uslovi. Titraciskiot aciditet, izrazen vo % na mle~na kiselina,
be{e odreduvan so titrirawe so 0.1N rastvor na natrium hidroksid i fenolftalein kako indikator.
Broeweto na koloniite na L. casei (CFU/ml) be{e vr{eno na MRS podloga (Merck KgaA, Darmstadt, Germany),
posle zasaduvawe na soodveten rastvor na liofiliziranoto soja mleko vo peptonska voda i inkubacija vo
vreme od 72 ~asa na temperatura od 37
o
C. 
Vlagata vo liofiliziranite primeroci se dvi`e{e od 5.6-7.2%. Vrednostite za pH i titraciskiot
aciditet kaj neliofiliziranite primeroci so probiotik se dvi`ea od 6.82 i 0.073% m.k., a za tie so probi-
otik i sorbitol od 6.74 i 0.073% m.k., dodeka soodvetnite vrednosti vedna{ po liofilizacija za primerocite
bez sorbitol bea 6.92 i 0.058% m.k. i za tie so sorbitol 6.85 za pH i 0.07% m.k., soodvetno. Vo uslovi na ~uvawe,
4 nedeli na 4
o
C, vrednostite za pH i titraciski aciditet iznesuvaa 3.40/0.074% m.k. za primerocite bez sor-
bitol i 3.69/0.50% m.k. za primerocite so sorbitol. Soodvetnite vrednosti za primerocite so probiotik na
25
o
C iznesuvaa 3.08 /1.32 i za tie so sorbitol 2.98/1.40% m.k. Pogolema vitalnost na L. casei be{e zabele`ana
kaj liofiliziranite primeroci so sorbitol vedna{ po su{ewe i za vreme na ~uvawe na 4
o
C. 
Kako zaklu~ok, probiotikot L. casei poka`uva pogolema vitalnost i stabilnost vo fermentiran-
oto i liofilizirano soja mleko vo koe e dodaden sorbitol kako krioprotektant koga se ~uva na 4
o
C. 
Macedonian pharmaceutical bulletin 53 (1,2) 328-329 (2007)
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Selen content of some edible mushrooms from Republic of Macedonia
Biljana Bauer Petrovska
1
; Mitko Karadelev
2
; Olga Kirovska Cigulevska
3
1
Faculty of Pharmacy, University of “Ss Ciryl and Methodius“, Vodnjanska 17;
2
Institute of Biology, Faculty of Natural Sciences and Mathematics, 
University of “Ss Ciryl and Methodius“, Gazi Baba bb, P.O.Box 162;
3
JZO ZZZ Skopje, Treta Mak. Brigada 18; 1000 Skopje, R Macedonia
Selenium is an essential dietary component for humans, and there is increasing evidence for the efficacy
of selenium as cancer-preventive compound and its protective effect at various stages of carcinogenesis including
both the early and later stages of cancer progression. Also negative effect in the case of hiperselenosis exists. It is,
therefore of interest to know the levels of selenium in higher edible mushrooms, since mushrooms can easily accu-
mulate minerals. Mushrooms collecting and its cultivation is very popular in Republic of Macedonia, particularly
due to its substantial contribution to food intake.
Acumulation of selenium was analyzed in eleven mushroom species collected from different mountanous
regions of the Republic of Macedonia in 1998-2005. Determination of the concentration of selenium was made with
the aid of atomic absorption spectrometry on the instrument Optima-QES 2000. 
Results expressed on dry mass basis indicate that the content of selenium in the analysed mushroom sam-
ples was consistent ranging from 0.02 mg/kg in Agaricus campester (L.) Fr. to 0.14 mg/kg in Tricholoma terreum
(Schaeff.) Quel., with the exception of Lactarius deliciosus Fr. from Krushino with a mean level of 0.46 mg/kg.
The average selenium content of 0.12 mg/kg make the investigated mushrooms a valuable source of selenium for
human diet. Our results agree reasonably well with the levels found in literature for many mushrooms species, less
than 1.0 mg/kg dry matters. But some species in the literature were found exceptionally rich in selenium what will
facilitate us for our further investigations on more samples from more areas in Republic of Macedonia.
Macedonian pharmaceutical bulletin 53 (1,2) 330-331 (2007)
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Sodr`ina na selen vo nekoi jadlivi gabi 
od Republika Makedonija
Biljana Bauer Petrovska
1
; Mitko Karadelev
2
; Olga Kirovska Cigulevska
3
1
Farmacevtski fakultet, Univerzitet „Sv. Kiril i Metodij“, Vodwanska 17; 
2
Institut za Biologija, Prirodno - matemati~ki fakultet, 
Univerzitet „Sv. Kiril i Metodij“, Gazi Baba bb, P. Fah 162; 
3
JZO ZZZ Skopje, Treta Mak. Brigada 18; 1000 Skopje, R. Makedonija
Selen e esencielna dietska komponenta na ~ovekot. Vo posledno vreme postojat zgolemen broj na
dokazi za efikasnosta na selen kako kancer protektivna komponenta i za negovite protektivni efekti
vrz razli~ni stepeni na karcinogeneza vklu~uvaj}i gi i ranite i kasnite fazi od progresijata na kancerot.
Me|utoa, se javuvaat i negativni efekti vo slu~aj na hiperselenoza. Poradi toa e zna~ajno od nutritiven
i toksikolo{ki aspekt da se odredat koli~inite na selen vo vi{ite jadlivi gabi, koi lesno mo`at da aku-
muliraat minerali. Sobiraweto i kultivacija na gabi e mnogu popularno vo Republika Makedonija,
osobeno poradi nivniot zna~aen pridones vo vkupniot vnes na hrana.
Akumulacijata na selen e istra`uvana vo edinaeset razli~ni vidovi gabi sobrani vo pove}e planin-
ski regioni na Republika Makedonija vo period od 1998-2005 godina. Odreduvaweto na koncentracijata
na selen e napraveno so metodot na atomska emisiona spektrometrija na instrument Optima-QES 2000.
Rezultatite od istra`uvawata vr{eni na suvi gabi poka`uvaat deka sodr`inata na selen vo anal-
iziranite primeroci na gabi se dvi`i vo tesni granici od 0,02 mg/kg vo Agaricus campester (L.) Fr. do 0,14
mg/kg vo Tricholoma terreum (Schaeff.) Quel. Isklu~ok e gabata Lactarius deliciosus Fr. od Kru{ino kade e najde-
na povisoka koncentracija od 0,46 mg/kg. Odredenata prose~na koncentracija na selen od 0,12 mg/kg vo suvi
gabi poka`uva deka ispituvanite gabi pretstavuvaat zna~aen izvor na selen vo ~ovekovata ishrana. 
Sodr`inite na selen dobieni vo makedonskite jadlivi gabi, se vo ramkite na podatocite najdeni
vo literaturata za pove}e razli~ni vidovi gabi, pomalku od 1.0 mg/kg vo suvi gabi. No, za nekoi vidovi,
vo literaturata se najdeni ekstremno visoki koncentracii na selen {to pretstavuva predizvik za na{i
ponatamo{ni istra`uvawa na sodr`ina na selen vrz pove}e razli~ni vida na jadlivi gabi sobrani od
pove}e predeli na Republika Makedonija.
Macedonian pharmaceutical bulletin 53 (1,2) 330-331 (2007)
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Biological value of proteins of some edible species of mushrooms 
from Republic of Macedonia
Biljana Bauer Petrovska
1
, Mitko Karadelev
2
, Svetlana Kulevanova
1
1
Faculty of Pharmacy, Ss Cyril and Methodius University, Vodnjanska 17; 
2
Institute of Biology, Faculty of Natural Science and Mathematics, Ss Cyril and Methodius University, Gazi Baba bb,
P.O. Box 162, 1000 Skopje, Republic of Macedonia
Edible mushrooms are rich with proteins with different biological values which varied in accordance with the bio-
logical characteristics of the genera and their origin. Thus, the purpose of this study was to estimate the values of param-
eters important for evaluating the protein biological value of edible mushrooms and their appreciating as protein nutrients.
The present study comprised fifty three specimens of wild and cultivated edible specieses of mushrooms, col-
lected in different areas of Republic of Macedonia. After acid hydrolysis and pre – column derivatisation with phenyl
isothiocyanate (PITC) determination of seventeen amino acids was carried out by the HPLC method. Tryptophan was
determined spectrophotometrically in the alkaline hydrolysates. Biological protein value of the investigated mushrooms
was evaluated by comparison of the essential amino acid content with the reference FAO/WHO pattern.
Most of the investigated species of edible mushrooms from Republic of Macedonia distinguished for their great
biological value, great protein efficiency ratio, and high place in the protein chemical range. The obtained high values of
essential amino acid index showed that the investigated Macedonian edible mushrooms contained proteins with good
quality able to supplement the necessity requirements for preserving of the human organisms. Essential amino acids made
37 to 75 % of all amino acids. The most found limiting amino acids in the investigated mushroom samples were lysine,
leucine threonine and valine. The biological value of the mushroom proteins varied from 51.3 % (Boletus edulis s.l. Bull.: Fr.)
to 90.4 % [Agaricus campester (L.)Fr. ]. The investigated edible Macedonian mushroom species can serve as a source of
good quality proteins able to supplement and replace the animal proteins in the human diet. The investigated cultivated
and wild Macedonian mushroom samples contained proteins necessary for the growth of the human organisms. According
to the protein efficiency ratio values the species from the following genera Calvatia, Russula, and Coprinus could serve as a
source of high quality proteins. Marasmius, Macrolepiota, Leccinium, Boletus, Agrocybe and Lactarius have medium qual-
ity proteins. Low quality proteins were estimated in the specimens from the genera Morchella, Laetiporus, Tricholoma,
Pleurotus and Cantharellus.
Macedonian pharmaceutical bulletin 53 (1,2) 332-333 (2007)
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Biolo{ka vrednost na proteinite na nekoi jadlivi vidovi gabi
od Republika Makedonija
Biljana Bauer Petrovska
1
, Mitko Karadelev
2
, Svetlana Kulevanova
1
1
Farmacevtski fakultet, Univerzitet „Sv. Kiril i Metodij“, Vodwanska 17; 
2
Institut za Biologija, Prirodno - matemati~ki fakultet, 
Univerzitet „Sv. Kiril i Metodij“, Gazi Baba bb, P. Fah 162; 1000 Skopje, Republika Makedonija
Jadlivite gabi se bogati so proteini so razli~na biolo{ka vrednost koja varira vo zavisnost od
biolo{kite karakteristiki na rodovite i nivnoto poteklo. Spored toa, celta na ovaa studija be{e da
se utvrdat vrednosti na parametri za ocenuvawe na biolo{kata vrednost na proteinite na jadlivi gabi
i nivno vrednuvawe kako proteinski namirnici. 
Vo ovaa studija bea vklu~eni pedeset i tri primeroci na samoniknati i kultivirani vidovi na
jadlivi gabi, sobrani od razli~ni podra~ja na Republika Makedonija. Po pretkolonska derivatizacija
na aminokiselinite vo kiseli hidrolizati so fenilizotiocijanat (PITC) so HPLC metod e opredeluvana
sodr`ina na sedumnaeset aminokiselini. Triptofanot e opredeluvan so spektrofotometriski metod vo
bazni hidrolizati. Biolo{kata vrednost na proteinite vo ispituvanite gabi oceneta e vrz osnova na
sodr`inata na esencijalnite aminokiselini vo odnos na istite aminokiselini vo predlo`eniot model
na FAO/SZO. 
Pove}eto od ispitanite vidovi na jadlivi gabi od Makedonija imaat visoka bilo{ka vrednost,
visok indeks na efikasnost i visoko mesto vo hemiskata skala na proteini. Dobienite visoki vrednos-
ti za esencielni aminokiselinski indeks poka`uva deka ispituvanite gabi sodr`at kvalitetni protei-
ni potrebni za odr`uvawe na ~ovekoviot organizam. Vo dovolni koli~estva od 37 do 75 % se zastapeni
site esencielni aminokiselini, osven limitira~kite lizin, leucin, treonin i valin. Biolo{kata vred-
nost na proteinite na ispituvanite makedonski jadlivi gabi se dvi`i vo granici od 51,3 % (Boletus edulis
s.l. Bull.:Fr.) do 90,4 % (Agaricus campester (L.)Fr.). Ispituvanite gabi mo`e da slu`at kako dobar izvor na
kvalitetni proteini, sposobni da gi nadopolnat i celosno zamenat proteinite od `ivotinsko poteklo
vo ~ovekovata ishrana. Vrz osnova na izvr{enite analizi i dobienite rezultati na pogolem broj na
jadlivi gabi od Republika Makedonija, mo`e da se konstatira deka vo grupata na gabi koi sodr`at visoko
kvalitetni proteini potrebni za rast na ~ovekoviot organizam, spa|aat slednite rodovi na gabi Calvatia,
Russula, Coprinus, Suillus, Agaricus, Amanita, Lentinus, so sreden kvalitet se proteinite na gabite od rodot
Marasmius, Macrolepiota, Leccinium, Boletus, Agrocybe, Lactarius, i nizok kvalitet na proteini imaat gabite od
rodovite Morchella, Laetiporus, Tricholoma, Pleurotus i Cantharellus.
Macedonian pharmaceutical bulletin 53 (1,2) 322-333 (2007)
PP - 171
333
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