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inhibitory effect of the isolated compounds and water
infusion from the leaves of L. vulgare on the activ-
ity of lipoxygenase isolated from the cytosolic fraction
of rat lungs. Data are reported as IC50 values (Ta-
ble 1). Water infusion and two isolated compounds,
oleuropein and echinacoside, exhibited remarkable in-
hibitory effect on LOX. An iridoid derivative, oleu-
ropein, was proved to be the most effective. This is
in good correlation with literature data. Oleuropein is
one of the most active substances in virgin olive oil (de
la Puerta et al., 1999). In intact rat peritoneal leuko-
cytes stimulated with calcium ionophore, oleuropein,
tyrosol, hydroxytyrosol, and caffeic acid from virgin
olive oil, leukotriene B4 generation was inhibited at
the 5-lipoxygenase level.
Fig. 1 shows the determination of the character of
inhibition in the presence of inhibitors. Kinetic pa-
rameters KM and Vmax of Michaelis–Menten equa-
tion were expressed from Lineweaver–Burk equation:
V −1 = KMVm−a1x[S]−1 + Vm−a1x; where [S]/(mol L−1) is
a substrate concentration; they demonstrate competi-
tive inhibition of all tested inhibitors. This activity can
be potentiated with the activity of flavonoids, exhibit-
ing remarkable activity against LOX (Bezáková et al.,
2007), isolated from this plant previously (Šeršeň et
al., 2006; Mučaji et al., 2006) or on the classical path-
way of the complement system (Pieroni & Pachaly,
2000a). These results clearly indicate that the tested
samples contribute to the inhibitory activity of L. vul-
gare water infusion used for anti-inflammatory pur-
poses in traditional medicine. However, the potential
therapeutic value and the real clinical efficacy of this
plant should be proved by further in vitro and in vivo
experiments.
Franzyk, H., Olsen, C. E., & Jansen, S. R. (2004). Dopaol 2-
keto- and 2,3-diketoglycosides from Chelone obliqua. Journal
of Natural Products, 67, 1052–1054. DOI: 10.1021/np04994
16.
Hammermann, A. F., Damirov, J. A., & Sokolov, W. S. (1971).
Einige aussichtsreiche Pflanzen der Volksmedizin von Azer-
bajdschan. Planta Medica, 20, 374–380. DOI: 10.1055/s-
0028-1099719.
Hromádková, Z., Hirsch, J., & Ebringerová, A. (2010). Chemical
evaluation of Fallopia species leaves and antioxidant proper-
ties of their non-cellulosic polysaccharides. Chemical Papers,
64, 663–672. DOI: 10.2478/s11696-010-0054-2.
Jiménez, J. T., O’Connell, S., Lyons, H., Bradley, B., & Hall, M.
(2010). Antioxidant, antimicrobial, and tyrosinase inhibition
activities of acetone extract of Ascophyllum nodosum. Chem-
ical Papers, 64, 434–442. DOI: 10.2478/s11696-010-0024-8.
Kemal, C., Louis-Flamberg, P., Krupinski-Olsen, R., & Shorter,
A. L. (1987). Reductive inactivation of soybean lipoxyge-
nase 1 by catechols: a possible mechanism for regulation
of lipoxygenase activity. Biochemistry, 26, 7064–7072. DOI:
10.1021/bi00396a031.
Kiss, A. K., Man´k, M., & Melzig, M. F. (2008). Dual inhibition
of metallopeptidases ACE and NEP by extracts, and iridoids
from Ligustrum vulgare L. Journal of Ethnopharmacology,
120, 220–225. DOI: 10.1016/j.jep.2008.08.015.
Kulkarni, A. P., Cai, Y., & Richards, I. S. (1992). Rat pul-
monary lipoxygenase: dioxygenase activity and role of xeno-
biotic metabolism. International Journal of Biochemistry,
24, 255–261. DOI: 10.1016/0020-711X(92)90255-Y.
Ma, S.-C., He, Z.-D., Deng, X.-L., But, P. P.-H., Ooi, V. E.-
C., Xu, H.-X., Lee, S. H.-S., & Lee, S.-F. (2001). In vitro
evaluation of secoiridoid glucosides from the fruits of Ligus-
trum lucidum as antiviral agents. Chemical & Pharmaceuti-
cal Bulletin, 49, 1471–1473. DOI: 10.1248/cpb.49.1471.
Mabry, T. J., Markham, K. R., & Thomas, M. B. (1970). The
systematic identification of flavonoids. New York, NY, USA:
Springer-Verlag.
Mučaji, P., Nagy, M., Grančai, D., & Švajdlenka, E. (2006).
Flavonoidné glykozidy Ligustrum vulgare L. Farmaceutický
Obzor, 75(10–11), 266–271.
Acknowledgements. This work was supported by the Slovak
Grant Agency VEGA (projects Nr. 1/0145/10 and 2/0083/08).
NMR measurements were enabled by the Slovak State Pro-
gram Project No: 2003SP200280203. Standard of acteoside for
HPLC identification was kindly provided by the authors from
the Institute of Natural Drugs, Faculty of Pharmacy, Univer-
sity of Veterinary and Pharmaceutical Sciences, Brno.
Nagao, T., Abe, F., & Okabe, H. (2001). Antiproliferative con-
stituents in the plants 7. leaves of Clerodendron bungei and
leaves and bark of C. trichotomum. Biological & Pharma-
ceutical Bulletin, 24, 1338–1342. DOI: 10.1248/bpb.24.1338.
Nagy, M., Križková, L., Mučaji, P., Kontšeková, Z., Šeršeň,
F., & Krajčovič, J. (2009). Antimutagenic activity and rad-
ical scavenging activity of water infusions and phenolics
from Ligustrum plants leaves. Molecules, 14, 509–518. DOI:
10.3390/molecules14010509.
References
Nagy, M., Spilková, J., Vrchovská,V., Kontšeková, Z., Šeršeň,
F., Mučaji, P., & Grančai, D. (2006). Free radical scavenging
activity of different extracts and some constituents from the
leaves of Ligustrum vulgare and L. delavayanum. Fitoterapia,
77, 395–397. DOI: 10.1016/j.fitote.2006.04.010.
Pan, L. T., He, X. P., & Yanag, L. Y. (2002). Studies on chemical
constituents in the leaf of Ligustrum delavayanum. Zhongguo
Zhong Yao Za Zhi, 27, 754–756.
Pieroni, A., & Pachaly, P. (2000a). An ethnopharmacological
study on common privet (Ligustrum vulgare) and phillyrea
(Phillyrea latifolia). Fitoterapia, 71, Supplement 1, S89–S94.
DOI: 10.1016/S0367-326X(00)00182-9.
Pieroni, A., & Pachaly, P. (2000b). Isolation and structure elu-
cidation of ligustroflavone, a new apigenin triglycoside from
the leaves Ligustrum vulgare L. Pharmazie, 55, 78–80.
Scogin, R. (1992). The distribution of acteoside among an-
giosperms. Biochemical Systematics and Ecology, 20, 477–
480. DOI: 10.1016/0305-1978(92)90090-Z.
Bezáková, L., Grančai, D., Obložinský, M., Vanko, M., Holková,
I., Pauliková, I., Garaj, V., & Gáplovský, M. (2007). Effect
of flavonoids and cynarine from Cynara cardunculus L. on
lipoxygenase activity. Acta Facultatis Pharmaceuticae Uni-
versitatis Comenianae, 54, 48–53.
Bezáková, L., Misik, V., Máleková, L., Svajdlenka, E.,
&
Kostálová, D. (1996). Lipoxygenase inhibition and antiox-
idant properties of bisbenzylisoquinoline alkaloids isolated
from Mahonia aquifolium. Pharmazie, 51, 758–761.
Bradford, M. M. (1976). Rapid and sensitive method for the
quantitation of microgram quantities of protein utilizing the
principle of protein-dye binding. Analytical Biochemistry, 72,
248–254. DOI: 10.1016/0003-2697(76)90527-3.
de la Puerta, R., Ruiz Gutierrez, V., & Hoult, J. R. S. (1999).
Inhibition of leukocyte 5- lipoxygenase by phenolics from vir-
gin olive oil. Biochemical Pharmacology, 57, 445–449. DOI:
10.1016/S0006-2952(98)00320-7.