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1

The effect of 5-(n-alk(en)yl) resorcinols on membranes. I. Characterization of the permeability increase induced by 5-(n-heptadecenyl) resorcinol

100%

Kozubek A.

Acta Biochimica Polonica

|

1987

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tom 34

|

nr 4

2

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Isolation of 5-n-alkyl, 5-n-alkenyl- and 5-n-alkdienyl- resorcinol homologs from rye grains

100%

Kozubek A.

Acta Alimentaria Polonica

|

1985

|

tom 11

|

nr 2

For the isolation of pure individual saturated, mono and di unsaturated homologs of 5-n-alk(en)ylresorcinols from the acetone extracts of rye grains the chromatographic procedure was used. This procedure employed column chromatography on silica gel followed by reversed-phase high pressure liquid chromatography and silver nitrate impregnated silica gel. The yeld of the pure homologs after rechromatography by reversed-phase high pressure liquid chromatography was about 27 per cent.

3

The effect of 5-(n-alk(en)yl) resorcinols on membranes. II. Dependance on the aliphatic chain lenght and unsaturation

100%

Kozubek A.

Acta Biochimica Polonica

|

1987

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tom 34

|

nr 4

4

Aktywnosc biologiczna lipidow rezorcynolowych

100%

Kozubek A.

Postępy Biochemii

|

1993

|

tom 39

|

nr 4

264-270

5

Interaction of alkylresorcinols with proteins

100%

Kozubek A.

Acta Biochimica Polonica

|

1995

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tom 42

|

nr 2

Alkylresorcinol homologs form stable monomolecular layers at air-water interface. Their interaction with proteins present in the subphase results in an increase of alkylresorcinol molecular packing in the extent dependent upon the protein studied. Strongest effects were observed for proteins with large hydrophobic regions, e.g. glycophorin or serum albumin. Interaction of proteins with alkylresorcinol monolayers is stronger than with phospholipids. A decrease and a shift of intrinsic protein fluorescence upon interaction with the compounds studied support their involvement in alteration of hydrophobic regions. For trypsin, 50% quenching was observed at the alkylresorcinol/trypsin ratio of 0.75. Concomitantly, an apparent inhibition of the enzymatic activity was noted. These results indicate that direct interaction of alkylresorcinols and modulation of enzymatic activities should be recognised as a significant part of the biological effect of these cereal bran components.

6

Determination of octanol-water partition coefficients for long-chain homologs of orcinol from cereal grains

100%

Kozubek A.

Acta Biochimica Polonica

|

1995

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tom 42

|

nr 2

Polycratic reversed-phase high-performance liquid chromatography (RPHPLC) was used for estimation of the octanol/water partition coefficient for three highly hydrophobic long chain orcinol homologs. The homologs studied (C 15:0, C 17:0 and C 19:0) showed high preference for hydrophobic phase as evidenced by their high octanol/water partition coefficient (log P o/w ) values of 7.02-7.74; 8.71-9.47 and 10.49-11.32 for the 95% prediction interval, respectively. Experimentally estimated values were compared with log P values calculated with the use of several fragmental systems. The experimental values of log P o/w are in best agreement to those calculated with the use of the Klopman system (Klopman, Gv Namboodiri, K. & Schochet, M., 1985, /. Comput. Chem. 6,28-38). The lack of appropriate standard compounds with known log P 0/w in the range over 6 markedly affected the accuracy of experimental determinations.

7

The effect of long chain orcinol homologs from cereal grains on platelet fibrinogen binding

63%

Wroblewski Z., Kozubek A.

Biophysics of Membrane Transport

|

1990

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tom 10

|

nr 2

8

5-n-alkilorezorcynole ziaren zboz i pelnoziarnistych produktow spozywczych jako biomarkery zdrowej zywnosci

63%

Kulawinek M., Kozubek A.

Postępy Biochemii

|

2007

|

tom 53

|

nr 3

287-296

9

The effect of resorcinolic lipids on the development of eggs and hatching of miracida in Fasciola hepatica L.

63%

Bielecki A., Kozubek A.

Zoologica Poloniae

|

1994

|

tom 39

95-104

10

Antioxidant properties of long chain orcinol homologs from cereal grains

63%

Struski D. G. J., Kozubek A.

Biophysics of Membrane Transport

|

1990

|

tom 10

|

nr 2

11

Inhibition of soybean lipoxygenases by resorcinolic lipids from cereal bran

63%

Deszcz L., Kozubek A.

Cellular and Molecular Biology Letters

|

1997

|

tom 02

|

nr 2

Incubation of soybean lipoxygenase isoenzymes (L-1, L-2, and L-3) with total resorcinolic lipids isolated from wheat bran or their purified homologs (5-n-pentadecylresorcinol and 5-n-tricosylresorcinol) led to apparent inhibition of all three isoenzyme activities. The IC50 values determined for studied compounds showed that the inhibitory activity was related to the length of the resorcinolic lipid aliphatic chain and was more effective for homolog with longer chain attached to 1,3-dihydroxybenzene ring in metha position. Similar dependence on the length of the alkylresorcinol side chain was observed also for Ki values. The 5-n-tricosylresorcinol (23:0 AR) was found to be the most efficient inhibitor of soybean lipoxygenases with IC50 values in the range of several µM regardless of the substrate used (linoleic acid or arachidonic acid). All alkylresorcinols studied caused increase of apparent KM values and decrease of VMAX values of the enzymes thus suggested the mixed type of lipoxygenase inhibition.

12

Modulation of 5-N-alkylresorcinol hemolytic properties by divalent cations. Dependence of the effect of cations on alkylresorcinol structure

63%

Stasiuk M., Kozubek A.

Cellular and Molecular Biology Letters

|

1997

|

tom 02

|

nr 1

It was demonstrated that the process of hemolysis of erythrocytes induced by resorcinolic lipids is inhibited by divalent cations present in the incubation medium. The extent of inhibition is dependent on the nature of both type of the cation and the hemolytic agent. Lysis most susceptible to divalent cations is that induced by short (C15) and medium-chained (C19) 5-n-alkylresorcinols, which also have the highest observed hemolytic potencies. Furthermore, the protection was the stronger the stronger lytic activity was exerted by studied compound. The homologs with the longest side chain studied, although exhibiting the lowest hemolytic activity by themself, were the least susceptible to inhibition of their hemolytic activity by cations. The effect of cobalt cation has been found to be intermediate between the effect of Mn2+ and Zn2+. The most effective in protection of erythrocytes was Zn2+ which almost completely protected the cells against alkylresorcinol-induced lysis at the concentrations of 10-6 M and above.

13

Cereal grain resorcinolic lipids inhibit H2O2-induced peroxidation of biological membranes

63%

Kozubek A., Nienartowicz B.

Acta Biochimica Polonica

|

1995

|

tom 42

|

nr 3

Cereal grain resorcinolic lipids (S-n-alk(en)ylresorcinols) at micromolar concentrations are able to protect the erythrocyte membrane against hydrogen peroxide-induced lipid oxidation. The antioxidative effect is dependent upon chain length of alkylresorcinol molecules. The C15:0 homolog (IC50 of 10 uM) exhibited strongest activity whereas for long chain homologs (C19: 0 and C23 : 0) IC50 values were higher, 32.5 and 59 uM, respectively. The protective effect of alkylresorcinolic antioxidants was also dependent on their incorporation into the membrane, that is governed by their water-membrane partition coefficient The results obtained show that alkylresorcinols should be recognized as hydrophobic, membrane-localised antioxidants.

14

The effect of resorcinolic lipids on the development of eggs and hatching of miracidia in Fasciola hepatica L.

63%

Bielecki A., Kozubek A.

Zoologica Poloniae

|

1994

|

tom 39

|

nr 1-2

15

Long-chain orcinol homologs from cereal bran are effective inhibitors of glycerophosphate dehydrogenase

63%

Rejman J., Kozubek A.

Cellular and Molecular Biology Letters

|

1997

|

tom 02

|

nr 4

It was found that 5-n-alk(en)ylresorcinols isolated from high-fiber diet, wheat or rye bran, effectively inhibit glycerol-3-phosphate dehydrogenase (GPDH, EC 1.1.1.8), the key enzyme of triacylglycerol synthesis in adipocytes. The concentration of alk(en)ylresorcinols necessary for 50 per cent inhibition of GPDH vary from 3.8 µM to 6.4 µM. The effectiveness of the inhibition depends on the length of alk(en)enylresorcinol side chain and hydrophilic ring substitutions. The effectivity of homologs with long side chain (C17 and C19) in apparent inhibition of GPDH is slightly higher than that reported previously for adipostatin A (5-n-pentadecylresorcinol) isolated from Streptomyces (Tsuge, N., Mizokami, M., Imai, S., Shimazu, A., & Seto, H. (1992) J. Antibiot. 45, 886- 891). The fact that the studied resorcinols are natural components of high-fiber human diet, such as porridge and bran products, suggests their possible participation in prevention of the risk of corpulence.

16

Modulation of plant nuclear matrix nucleolytic activity and specificity may result from interaction of nuclease-protein 14-3-3 complex with inner nuclear membrane lipids

63%

Lubocka J., Kozubek A.

Cellular and Molecular Biology Letters

|

1998

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tom 03

|

nr 1

Plant cell nuclear matrix depleted in lipids exhibited approximately 50% lower endonucleolytic activity attributed to 32 kDa nuclease. Supplementation of delipidated matrix with phospholipids, sterols and glycolipids resulted in the recovery of nuclease activity. The extent of recovery is dependent upon the type of lipid used for reconstitution. The most effective (over 97%) in recovery of the nucleolytic activity were PC, PE, DGDG and stigmasterol. Some recovery is also observed when other natural amphiphilic molecules are studied (resorcinolic lipids). Recombinant plant protein 14-3-3 showed ability for direct interaction with lipid monolayers. The interaction was confirmed by analysis of the monolayer collected from the subphase after incubation with protein 14-3-3. Deletion of the 12 kDa N-terminal fragment of the protein 14-3-3 abolished its ability for binding to lipid monolayer. The results suggest that in vivo direct interaction of protein 14-3-3 with nuclear envelope lipids may participate in modulation of the nuclease 32 kDa activity. A postulated model of the interactions is discussed.

17

Modulation of nuclear matrix nucleolitic activity by lipids

63%

Lubocka J., Kozubek A.

Cellular and Molecular Biology Letters

|

1997

|

tom 02

|

nr 2

18

Resorcinolic lipids from cereal bran as natural antioxidants

63%

Nienartowicz B., Kozubek A.

Polish Journal of Food and Nutrition Sciences

|

1993

|

tom 02

|

nr 4

19

Modulation of hemolytic properties of resorcinolic lipids by divalent cations

63%

Stasiuk M., Kozubek A.

Cellular and Molecular Biology Letters

|

1996

|

tom 01

|

nr 2

The effect of divalent cations in concentrations 10-9-10-3M upon the hemolysis of sheep erythrocytes induced by resorcinolic lipids was studied. It was demonstrated that the process of hemolysis is inhibited by divalent cations present in the incubation medium. The extent of inhibition is dependent on both type of the cation and hemolytic agent. In alkylresorcinol-induced hemolysis the most effective in protection of the cells were Zn2+ and Co2+ cations. Weaker protective action was observed for Cd2+ and Mn2+. Calcium ions, in all studied concentrations, were without marked effect on the level of relative hemolysis. Magnesium ions as well as Ba2+ in nanomolar concentrations were effective inhibitors of the lysis but this effect diminished at higher (millimolar) concentrations of these ions. When alkenylresorcinols were used as hemolysis-inducers no effective protection of erythrocytes by Ca2+, Ba2+ or Mg2+ was observed. Most effective in protection of cells against this amphiphile-induced lysis, similarly to their effect observed previously for various lytic agents, were cations of Zn2+, Co2+ and Cd2+. Mn2+ cations were intermediate, with respect to their protective potency.

20

Zmiany kształtu erytrocytów i czynniki je wywołujące

51%

Stasiuk M., Kijanka G., Kozubek A.

Postępy Biochemii

|

2009

|

tom 55

|

nr 4

Ograniczanie wyników

The effect of 5-(n-alk(en)yl) resorcinols on membranes. I. Characterization of the permeability increase induced by 5-(n-heptadecenyl) resorcinol

Isolation of 5-n-alkyl, 5-n-alkenyl- and 5-n-alkdienyl- resorcinol homologs from rye grains

The effect of 5-(n-alk(en)yl) resorcinols on membranes. II. Dependance on the aliphatic chain lenght and unsaturation

Aktywnosc biologiczna lipidow rezorcynolowych

Interaction of alkylresorcinols with proteins

Determination of octanol-water partition coefficients for long-chain homologs of orcinol from cereal grains

The effect of long chain orcinol homologs from cereal grains on platelet fibrinogen binding

5-n-alkilorezorcynole ziaren zboz i pelnoziarnistych produktow spozywczych jako biomarkery zdrowej zywnosci

The effect of resorcinolic lipids on the development of eggs and hatching of miracida in Fasciola hepatica L.

Antioxidant properties of long chain orcinol homologs from cereal grains

Inhibition of soybean lipoxygenases by resorcinolic lipids from cereal bran

Modulation of 5-N-alkylresorcinol hemolytic properties by divalent cations. Dependence of the effect of cations on alkylresorcinol structure

Cereal grain resorcinolic lipids inhibit H2O2-induced peroxidation of biological membranes

The effect of resorcinolic lipids on the development of eggs and hatching of miracidia in Fasciola hepatica L.

Long-chain orcinol homologs from cereal bran are effective inhibitors of glycerophosphate dehydrogenase

Modulation of plant nuclear matrix nucleolytic activity and specificity may result from interaction of nuclease-protein 14-3-3 complex with inner nuclear membrane lipids

Modulation of nuclear matrix nucleolitic activity by lipids

Resorcinolic lipids from cereal bran as natural antioxidants

Modulation of hemolytic properties of resorcinolic lipids by divalent cations

Zmiany kształtu erytrocytów i czynniki je wywołujące