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Studies on the preventive effect of Micromeria cristata extracts 
on fatty liver development by carbon tetrachloride in rats
Tatjana Kadifkova Panovska
1
, Svetlana Kulevanova
2
, Icko Gjorgoski
3
, 
Mirjana Bogdanova
4
, Gordana Petrushevska
5
1
Institute of Applied Biochemistry, Faculty of Pharmacy, 
University "Ss. Cyril and Methodius" Vodnjanska 17, 1000 Skopje, Republic of Macedonia
2
Institute of Pharmacognosy, Faculty of Pharmacy, 
University "Ss. Cyril and Methodius" Vodnjanska 17, 1000 Skopje, Republic of Macedonia
3
Institute of Biology, Faculty of Natural Sciences and Mathematics, 
University "Ss. Cyril and Methodius" P.B. 126, 1000 Skopje, Republic of Macedonia
4
Institute of Clinical Biochemistry, Clinical Center, Vodnjanska 17, 1000 Skopje, Republic of Macedonia
5
Institute of Pathology, Faculty of Medicine, 
University "Ss. Cyril and Methodius" Vodnjanska 17, 1000 Skopje, Republic of Macedonia
The liver is the key organ regulating homeostasis in the body. It is involved with almost all the biochemical
pathways related to growth, fight against disease, nutrient supply, energy provision and reproduction. The liver is
expected not only to perform physiological functions but also to protect against the hazard of harmful drugs and
chemicals. In spite of tremendous scientific advancement in the field of hepatology in recent years, liver problems
are on the rise. Jaundice and hepatitis are two major hepatic disorders that account for a high death rate. Presently
only a few hepatoprotective drugs from natural sources are available for the treatment of liver disorders.
The purpose of this study was to evaluate the hepatoprotective effect of Micromeria cristata extracts (diethyl
ether, ethyl acetate and n-butanol) in vivo using carbon tetrachloride (CCl
4
) intoxicated rats as an experimental model.
To assess the degree of liver damage we estimated some biochemical parameters in blood and in liver homogenates
and performed histopatological liver examinations.
The activities of hepatic marker enzymes (GPx and SOD) and biochemical parameter TAS were assayed in
blood and liver homogenate. Colorimetric estimation of reduced glutathione (GSH) in blood and in liver homogenate
was performed. The quantitative measurement of lipid peroxidation was done by measuring the concentration of
thiobarbituric acid reactive substances (TBARS) in liver homogenate. The amount of malondialdehide (MDA) formed
was quantitated by reaction with thiobarbituric acid and used as an index of lipid peroxidation. The content of pro-
tein was determined according to the method of Bradford using bovine serum albumin as a standard. Liver pieces
for histopatological examinations were preserved in 10% formaldehyde solution, embedded in paraffin wax, stained
with hematoxylin and eosin and photographed.
The results indicate that after CCl4 administration there was a slight increase in blood GPx relatively to the
control group. In the groups where sylimarin (reference substances) was given, the levels of GPx were significant-
ly lower (p<0.05) than in CCl
4
-treated group. The levels of SOD and TAS were significantly (p<0.05) reduced after
intoxication with CCl
4
. Acute exposure to a single intraperitoneal dose of CCl
4
resulted in a severe depletion of
GSH content in both blood and in liver homogenate. The depletion of GSH by CCl
4
was associated with an increase
in lipid peroxidation as measured by the level of TBARS in liver homogenate. Preceding administration of M. crista-
ta extract for 7 consecutive days afforded different degrees of protection against such depletion. The most signifi-
cant protection effect was found at the level of GPx, SOD and TBARS. This protective effect of M. cristata extracts
was confirmed by histological examination in which in the groups pretreated with M. cristata extracts the livers
exhibited an almost normal architecture, with the presence of double nucleus hepatocytes, barring a little deformity
of hepatocytes with pyknosis and clearing of cytoplasm.
The ability of M. cristata extracts to stimulate hepatic GPx and SOD can enhance the functioning of hepat-
ic GSH antioxidant system, in which the concerted action of these enzymes can provide a sustainable GSH-depend-
ent antioxidant mechanism, thereby protecting against CCl
4
hepatotoxicity.
Macedonian pharmaceutical bulletin 53 (1,2) 294-295 (2007)
PP - 143
294
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Studii za preventivniot efekt na ekstraktite 
od Micromeria cristata vrz razvojot na masen crn drob 
kaj CCl
4
tretirani staorci  
Tatjana Kadifkova Panovska
1
, Svetlana Kulevanova
2
, Icko \orgoski
3
, 
Mirjana Bogdanova
4
, Gordana Petru{evska
5
1
Institut za Primeneta biohemija, Farmacevtski fakultet, 
Univerzitet “Sv. Kiril i Metodij”, Vodwanska 17, 1000 Skopje, R. Makedonija 
2
Institut za Farmakognozija, Farmacevtski fakultet, 
Univerzitet “Sv. Kiril i Metodij”, Vodwanska 17, 1000 Skopje, R. Makedonija 
3
Institut za Biologija, Prirodno matemati~ki fakultet, 
Univerzitet “Sv. Kiril i Metodij”, P.B. 126, 1000 Skopje, R. Makedonija
4
Institut za Klini~ka biohemija, Klini~ki centar, Vodwanska 17, 1000 Skopje, R. Makedonija
5
Institut za Patologija, Medicinski fakultet, 
Univerzitet “Sv. Kiril i Metodij”, Vodwanska 17, 1000 Skopje, R. Makedonija 
Crniot drob e klu~niot organ vo reguliraweto na homeostazata na organizmot. Vo nego se odvi-
vaat site biohemiski reakcii povrzani so rastewe, odbrana od bolesti, obezbeduvawe na hranlivi materii
i energija i reprodukcija. So ogled na negovata kompleksnost, se o~ekuva ne samo da gi obezbeduva fizio-
lo{kite funkcii, tuku i da deluva za{titno vo odnos na {tetni lekovi i hemiski supstancii. Nasproti
silniot napredok na poleto na hepatologijata vo poslednite godini, problemite so crniot drob se vo po-
rast. @olticata i hepatitisot se dvete naj~esti zaboluvawa na crniot drob so golema stapka na smrtnost.
Denes postojat samo ograni~en broj na hepatoprotektivni lekovi za tretman na bolesti na crniot drob.
Celta na ovoj trud e da se proceni hepatoprotektivniot efekt na ekstraktite od Micromeria cristata
(dietil eteren, etil acetaten i n-butanolen) in vivo primenuvaj}i CCl
4
intoksicirani staorci kako eksper-
imentalen model. Za da se opredeli stepenot na o{tetuvawe na crniot drob, opredeluvani se odredeni bio-
hemiski parametri vo krv i homogenat na crn drob i napraveni se histopatol{ki ispituvawa.
Aktivnosta na hepati~nite marker enzimi (GPx i SOD) i biohemiskiot parametar TAS e opredelu-
vana vo krv i homogenat na crn drob. Reduciraniot glutation (GSH) kolorimetriski e opredeluvan vo krv
i homogenat na crn drob.  Kvantitativnoto izrazuvawe na lipidnata peroksidacija e mereno preku kon-
centracijata na tiobarbiturna kiselina reaktivnite supstancii vo homogenat na crb drob. Koli~inata
na formiraniot malondialdehid (MDA) e opredeluvana vo reakcija so tiobarbiturnata kiselina i se
upotrebuva kako indeks za lipidnata peroksidacija. Koli~inata na proteinite e opredeluvana spored
metodata na Bradford so govedski serum albumin kako standard.  Histopatolo{kite ispituvawa se
napraveni so prethodna podgotovka na crniot drob vo 10% formaldehid, vklopeni vo parafinski vosok,
boeni so hematoksilin i eozin i fotografirani. 
Rezultatite uka`uvaat deka posle davawe na CCl
4
se zgolemuva aktivnosta na GPx vo krvta vo spored-
ba so kontrolnata grupa. Vo grupata tretirana so silimarin, nivoto na  GPx e signifikantno namaleno
(p<0.05) vo odnos na grupata so CCl
4
. Nivoata na SOD i TAS signifikantno (p<0.05) se namaleni posle intok-
sikacija so CCl
4
. Akutnata ekspozicija na ednokratna intraperitonealna doza na CCl
4
predizvikuva
izrazeno opa|awe na nivoto na GSH, kako vo krvta, taka i vo homogenatot na crn drob. Ovoj fenomen e
povrzan so zgolemuvawe na obemot na lipidnata peroksidacija izmerena kako nivo na TBARS vo homogena-
tot na crniot drob. Administriraweto na ekstraktite od M. cristata vo tek na 7 posledovatelni denovi
obezbeduva razli~ni nivoa na za{tita. Najgolema za{tita e postignata na nivo na GPx, SOD i TBARS.
Protektivniot efekt na ekstraktite od M. cristata e potvrden so histopatolo{kite ispituvawa, vo koi
kaj grupite tretirani so ekstraktite e registrirana skoro normalna arhitektura na tkivoto, so prisust-
vo na dvojadreni hepatociti.
Sposobnosta na ekstraktite od M. cristata da gi stimuliraat hepati~nite GPx i SOD, mo`e da ja
podobri funkcijata na hepatalniot GSH antioksidativen sistem, vo koj sinhroniziranoto deluvawe na
ovie enzimi, obezbeduva odr`liv GSH-zavisen antioksidativen mehanizam, potreben za za{tita od CCl
4
hepatotoksi~nosta.
Macedonian pharmaceutical bulletin 53 (1,2) 294-295 (2007)
PP - 143
295
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Defining of the morphological - anatomical markers for identification
of root and herb from Eryngium campestre L. (Apiaceae)
Flurim Nebija
1
, Gjose Stefkov
2
, Marija Karapandzova
2
, Biljana Bauer Petrovska
2
, Svetlana Kulevanova
2
1
Medical faculty, Section Pharmacy, University in Prishtina, Kosovo
2
Faculty of Pharmacy, University of  Ss. Cyril and Methodius, Skopje, Republic of Macedonia
Genera Eryngium (Apiaceae) is consist from approximately 220 species, spread in Europe especially on the
Mediterranean region. The most spread species is Eryngium campestre, in Macedonia known as „vetrogon“, „vol-
sko trnje“, „bel trn“ or „sikavica“. From this plant root Eryngii radix and dry above soil part in stage of blooming
Eryngii herba are used. Both drugs are used mostly in the folk medicine, for treatment of infections on the urinary
tract, for regulation of the disturbed function of prostate, for treatment of disturbed functions of kidney and for
increased urine secretion, throwing out of stones and sand from kidney and bladder,  for healing of kidney colic's,
scarcely pissing, water retaining and other conditions.
Drugs Eryngii radix and Eryngii herba are not so much investigated. In relation to the chemical content it
is known that they comprehend saponin and flavonoid components, various coumarines, pirano coumarines,
acetylenes (falkarinol, falkarinon), sugar alcohol etc. In relation to the biological and pharmacological activity, in
the literature could be found data agreeable with the folk medicine, especially in the treatment of the infections and
other diseases on the uro-genital tract. Contrary to this macroscopic and microscopic characteristics are scarcely
investigated. The aim of this paper is to define the morphological - anatomical characteristics of both drugs which
could be used in purpose of identification.  
On the base of the obtained results from our investigations it could be concluded that the plant organs of
Eryngium campestre showed significant xeromorphity, especially leafs which are separated in spiny jagged slices,
covered with thick cuticle, with isolateral mesophill with palisade tissue on the upper and lower region of the leaf
and much reduced spongy parenchyma. Characteristic arrangement of the mechanical collenchyma tissue, especial-
ly in leafs, in combination with isolateral structure and present calcium oxalate druses, and characteristic wrinkles
in the leaf cuticle are pharmacodiagnostic markers for identification of drug on cross section. In the herb's powder
the follow elements could be found: trachea fragments with specific ring wrinkles, parts from the epiderma with
stomata, druses and knee-shaped mechanical hairs. In the root and the stem characteristic are secretory tubes and
the presence of calcium oxalate druses in great quantity. Additionally in the root typical arrangement of tissues char-
acteristic for the secondary root construction could be noticed, with: xylem rays in wood and in a bark, laticifers,
periderma on the periphery, characteristic arrangement of the vascular bundles and great number of druses, espe-
cially in the wood. In the root powder: trachea fragments with spiral thickenings, fragments of periderm and cork,
parts from parenchyma of the bark with druses could been put aside.
Macedonian pharmaceutical bulletin 53 (1,2) 296-297 (2007)
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Definirawe na morfolo{ko-anatomskite markeri za 
identifikacija na koren i herba od Eryngium campestre L. (Apiaceae)
Flurim Nebija
1
, \o{e Stefkov
2
, Marija Karapanxova
2
,
Biljana Bauer Petrovska
2
, Svetlana Kulevanova
2
1
Medicinski fakultet, Otsek Farmacija, Univerzitet vo Pri{tina, Kosovo
2
Farmacevtski fakultet, Univerzitet Sv. Kiril i Metodij, Skopje, Makedonija
Rodot Eryngium (Apiaceae) opfa}a okolu 220 vida, rasprostraneti vo Evropa, osobeno vo oblasta na
Mediteranot. Najrasprostranet vid e 
Eryngium campestre vo Makedonija poznat kako vetrogon, volsko
trwe, bel trn ili sikavica. Od ova rastenie se koristi korenot, Eryngii radix i suv nadzemen del vo faza
na cvetawe, Eryngii herba. Dvete drogi se koristat glavno vo narodna medicina, za tretman na infekcii na
urinarniot trakt, za regulirawe na naru{ena funkcija na prostatata, za tretman na naru{ena funkcija
na bubrezite i za zgolemno la~ewe na urinata, za isfrlawe na kamen i pesok od bubrezite i od mo~niot
meur, pri bubre`ni koliki, te{ko urinirawe, zadr{ka na voda i drugi sostojbi. 
Drogite Eryngii radix i Eryngii herba se malku prou~eni. Vo pogled na  hemiskiot sostav, poznato e
deka sodr`at saponinski i flavonoidni komponenti, razli~ni kumarini, piranokumarini, acetileni
(falkarinol, falkarinon), {e}erni alkoholi i drugo. Vo pogled na biolo{kata i farmakolo{kata
aktivnost, vo literaturata mo`at da se najdat podatoci  {to se vo soglasnost so upotrebata vo narodnata
medicina, osobeno vo tretmanot na infekciite i drugite zaboluvawa vo urogenitalniot trakt. Sprotivno
na ova, makroskopskite i mikroskopskite karakteristiki na korenot i herbata se malku prou~eni. Celta
na ovoj trud e definirawe na morfolo{ko-anatomskite karakteristiki na dvete drogi {to bi mo`ele da
se koristat vo farmakodijagnosti~kite celi. 
Vrz baza na dobienite rezultati od napravenite ispituvawa zaklu~eno e deka rastitelnite organi
na Eryngium campestre poka`uvaat izrazita kseromorfnost na rastenieto, osobeno kaj listovite kade tie
se podeleni vo bodlikavo-zap~esti rezni, pokrieni so debela kutikula, so mezofil koj ima izolateralna
gradba so palisadno tkivo na gornata i dolnata strana na listot i so mnogu reduciran sun|erest paren-
him. Karakteristi~en raspored na mehani~ko kolemhinsko tkivo, osobeno vo listovite, vo kombinacija
so izolateralnata gradba i prisutnite druzi od kalcium oksalat, kako i karakteristi~nite nabori na
kutikulata se farmakodijagnosti~ki markeri za identifikacija na drogata vo napre~en presek. Vo
pra{okot od herbata se izdvojuvaat fragmenti od traheite so specifi~ni prstenesti nabori, delovi od
epidermisot so stomite, druzi i kolenesti mehani~ki vlakna so specifi~na forma kako dijagnosti~ki
elementi bitni za identifikacijata. Utvrdeno e deka kaj korenot i kaj stebloto se karakteristi~ni sekre-
tornite kanali i prisustvoto na golemi koli~ini na druzi od kalcium oksalat. Kaj korenot se zabele`uva
tipi~en raspored na tkiva {to e karakteristi~en za sekundarna gradba na koren, so srcevinski zraci vo
drvoto i vo korata, mle~ni cevki, peridermis na periferija, karakteristi~en raspored na sprovodni
snop~iwa i golem broj druzi, osobeno vo drvoto. Vo pra{okot od korenot se izdvojuvaat fragmenti od tra-
hei so spiralni zadebeluvawa, fragmenti od peridermisot i od plutata, delovi od parenhimot na korata
so druzi i poedine~ni druzi, kako dijagnosti~ki elementi bitni za identifikacijata. 
Macedonian pharmaceutical bulletin 53 (1,2) 296-297 (2007)
PP - 144
297
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HPLC metod for identification and determination of flavonoids 
in Eryngii herba (Eryngium campestre L., Apiaceae)
Flurim Nebija
1
, Gjose Stefkov
2
, Marija Karapandzova
2
,  Marina Stefova
3, 
Svetlana Kulevanova
2
1
Medical faculty, Section Pharmacy, University in Prishtina, Kosovo
2
Faculty of Pharmacy, University of  Ss. Cyril and Methodius, Skopje, Republic of Macedonia
3
Faculty of Science, University of  Ss. Cyril and Methodius, Skopje, Republic of Macedonia
Eryngium campestre L. (Apiaceae) is perennial plant, spread in Europe especially on the Mediterranean
region. From this plant roots and dry above soil parts in stage of blooming are used in the folk medicine for treat-
ment of infections on the urinary tract, for regulation of the disturbed function of prostate, for treatment of disturbed
functions of kidney and for increased urine secretion, throwing out of stones and sand from kidney and bladder, for
healing of kidney colic's, scarcely pissing, water retaining and other conditions. Huge usage of Eryngii herba in folk
medicine as well as obtained results from investigation of biological and pharmacological activity of different species
of Eryngium, made the representatives of this genus interesting for investigation of the chemical composition and
definition the substances responsible for particular activity. In the frame of phenolic compounds the most investi-
gated are flavonoids. The literature data showed that Eringium planum contain kaempferol and its glycosides, E. ili-
cifolim contain daltoin, while E. maritimum contain glycosides of kaempferol, isoquercetin and astragalin and E.
creticum daltoin and quercetin. The data about flavonoids in E. campestre are very few in number and they point out
the presence of glycosides of quercetin, kaempefrol, isorhamnetin and luteolin. The aim of this work is establishing
HPLC method for identification and determination of flavonoids in Eryngii herba collected in Kosovo. 
The identification of the flavonoids in the extracts from Eryngii herba was made by HPLC method, using
reverse phase column (C18). Experimental conditions were in the accordance to expected flavonoids in the extracts.
Kaempferol was found as the most abundant flavonol, followed by smaller amounts of quercetin.
For quantification purposes of identified flavonols modification of previously established HPLC method
was done. Few approaches were defined: quantification of separated flavonols or quantification of total flavonols
measured as quercetin or as kaempferol. 
The obtained results of quantification of kaempferol and quercetin in the investigated extracts of Eryngium
campestre have showed that kaempferol is the dominated flavonol in this plant, found in amounts 0.029-0.103%,
while quercetin was found only in the range 0.001-0.039%. The content of total flavonols expresed as kaempferol
was 0.039-0.135%. It was concluded that the total content of flavonoids in the extracts which contain much more
kaempferol against quercetin, measuring them as kaempferol is much more recommended, instead of expression
them as quercetin, which is commonly present in the practice.  
Macedonian pharmaceutical bulletin 53 (1,2) 298-299 (2007)
PP - 145
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Voveduvawe na HPLC metod za identifikacija i opredeluvawe 
na flavonoidi vo Eryngii herba (Eryngium campestre L., Apiaceae)
Flurim Nebija
1
, \o{e Stefkov
2
, Marija Karapanxova
2
, Marina Stefova
3,
Svetlana Kulevanova
2
1
Medicinski fakultet, Otsek farmacija, Univerzitet vo Pri{tina, Kosovo
2
Farmacevtski fakultet, Univerzitet  Sv. Kiril i Metodij, Skopje, Makedonija
3
Prirodno-matemati~ki fakultet, Univerzitet Sv. Kiril i Metodij, Skopje, Makedonija
Eryngium campestre L. (Apiaceae) e pove}egodi{no rastenie, rasprostraneto vo Evropa, osobeno vo
oblasta na Mediteranot. Od rastenieto se koristat herbata i korenot, glavno vo narodna medicina za
tretman na infekcii na urinarniot trakt, za regulirawe na naru{ena funkcija na prostatata, za tret-
man na naru{ena funkcija na bubrezite i za zgolemno la~ewe na urinata, za isfrlawe na kamen i pesok
od bubrezite i od mo~niot meur, pri bubre`ni koliki, te{ko urinirawe, zadr{ka na voda i drugi sosto-
jbi. Golemata primena vo narodnata medicina kako i opredelenite rezultati od ispituvawata na
biolo{kata i farmakolo{kata aktivnost na vidovite od rodot Eryngium, gi pravat prestavnicite od ovoj
rod osobeno interesni za prou~uvawe na hemiskiot sostav i utvrduvaweto na potencijalno aktivnite kom-
ponenti, odgovorni za opredelni efekti. Vo odnos na fenolnite soedinenija, flavonoidnite komponen-
ti se podetalno prou~uvani. Podatocite poka`uvat deka vidot E. planum sodr`i kemferol i negovi het-
erozidi, vidot E. ilicifolium deltoin, E. maritinum heterozidi na kemferol, izokvercetin i astragalin, a E.
creticum deltoin i kvercetin. Podatocite za flavonoidnite komponenti vo vidot E. campestre se dosta oskud-
ni i se odnesuvat na utvrdeno prisustvo na heterozidi na kemferol, izoramnetin, luteolin i kvercetin.
Celta na ovoj trud e vospostavuvawe na metodi za identifikacija i opredeluvawe na flavonoidi vo Eryngii
herba (Eryngium campestre L.), po poteklo od Kosovo.
Identifikacija na flavonoidnite komponenti vo ekstrakti od Eryngii herba e napravena so HPLC
metod so reverzno fazna stacionarna faza (C18). Eksperimentalnite uslovi se postaveni vo soglasnost so
o~ekuvaweto na flavonolni aglikoni vo analiziraniot ekstrakt. Pri toa e utvrdeno prisustvo na kemfe-
rol kako dominantna flavonoidna komponenta vo site ispituvani ekstrakti, a vo pomala mera prisustvo
na kvercetin. 
Za kvantitativno opredeluvawe na identifikuvanite flavonoli izvr{ena e modifikacija na
predhodno vospostaveniot i validiran metod za opredeluvawe na kvercetin vo rastitelni ekstrakti
dobieni so vklu~ena hidroliza na heterozidnite formi. Vo kvantitativnata analiza bea razgledani
nekolku mo`ni pristapi: opredeluvawe na sodr`inata na sekoj od flavonolite, posebno, opredeluvawe
na sodr`ina na vkupni flavonoli presmetani kako kvercetin ili opredeluvawe na vkupni flavonoli
presmetani kako kemferol.
Rezultatite od opredeluvaweto na kemferol i kvercetin vo ekstraktite od Eryngium campestre
poka`uvaat deka dominanten flavonol e kemferolot ~ij masen udel se dvi`i od 0,029-0,103 %, dodeka
kvercetinot e zastapen od 0,001-0,019 %. Sodr`inata na vkupnite flavonoli presmetani kako kemferol
se dvi`i od 0,039-0,135 %. Zaklu~eno e deka vo rastitelni ekstrakti vo koi kako flavonol dominira kem-
ferol naspram kvercetin, izrazuvaweto na vkupni flavonoli treba da bide na molekulska masa na kem-
ferol, a ne na kvercetin {to e voobi~aena praksa.
Macedonian pharmaceutical bulletin 53 (1,2) 298-299 (2007)
PP - 145
299
^ETVRTI KONGRES NA FARMACIJATA NA MAKEDONIJA SO ME\UNARODNO U^ESTVO
FOURTH CONGRESS OF PHARMACY OF MACEDONIA WITH INTERNATIONAL PARTICIPATION