A new heteroleptic copper(II) compound named C0-UDCA was prepared by reaction of [Cu(phen)2(OH2)](ClO4)2 (C0) with the bile ursodeoxycholic acid (UDCA). The resulting compound is able to inhibit the lipoxygenase enzyme showing more efficacy than the precursors C0 and UDCA. Molecular docking simulations clarified the interactions with the enzyme as due to allosteric modulation. The new complex shows antitumoral effect on ovarian (SKOV-3) and pancreatic (PANC-1) cancer cells at the Endoplasmic Reticulum (ER) level by activating the Unfolded Protein Response. In particular, the chaperone BiP, the pro-apoptotic protein CHOP and the transcription factor ATF6 are upregulated in the presence of C0-UDCA. The combination of Intact Cell MALDI-MS and statistical analysis have allowed us to discriminate between untreated and treated cells based on their mass spectrometry fingerprints.

• Klíčová slova
• Copper complex, ER stress, Lipoxygenase, Mass spectrometry, Molecular docking, Solution equilibria,
• MeSH
• apoptóza MeSH
• buněčné linie MeSH
• fenantroliny chemie   MeSH
• inhibitory enzymů farmakologie   MeSH
• inhibitory lipoxygenas * farmakologie   MeSH
• kyselina ursodeoxycholová farmakologie   MeSH
• měď farmakologie   chemie   MeSH
• nádory slinivky břišní MeSH
• nádory * MeSH
• simulace molekulového dockingu MeSH
• stres endoplazmatického retikula MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• fenantroliny MeSH
• inhibitory enzymů MeSH
• inhibitory lipoxygenas * MeSH
• kyselina ursodeoxycholová MeSH
• měď MeSH

The aim of the study was to broadly determine the biological activities of purple potato ethanolic extract of the Blue Congo variety (BCE). The antioxidant activity of BCE was determined in relation to liposome membranes, and peroxidation was induced by UVB and AAPH. To clarify the antioxidant activity of BCE, we investigated its interactions with hydrophilic and hydrophobic regions of a membrane using fluorimetric and FTIR methods. Next, we investigated the cytotoxicity and pro-apoptotic activities of BCE in two human colon cancer cell lines (HT-29 and Caco-2) and in normal cells (IPEC-J2). In addition, the ability to inhibit enzymes that are involved in pro-inflammatory reactions was examined. Furthermore, BCE interactions with serum albumin and plasmid DNA were investigated using steady state fluorescence spectroscopy and a single molecule fluorescence technique (TCSPC-FCS). We proved that BCE effectively protects lipid membranes against the process of peroxidation and successfully inhibits the cyclooxygenase and lipoxygenase enzymes. Furthermore, it interacts with the hydrophilic and hydrophobic parts of lipid membranes as well as with albumin and plasmid DNA. It was observed that BCE is more cytotoxic against colon cancer cell lines than normal IPEC-J2 cells; it also induces apoptosis in cancer cell lines, but does not induce cell death in normal cells.

• MeSH
• albuminy MeSH
• antioxidancia chemie   farmakologie   MeSH
• fytogenní protinádorové látky chemie   farmakologie   MeSH
• inhibitory cyklooxygenasy chemie   farmakologie   MeSH
• inhibitory lipoxygenas chemie   farmakologie   MeSH
• lidé MeSH
• lipidy chemie   MeSH
• liposomy MeSH
• nádorové buněčné linie MeSH
• plazmidy MeSH
• reaktivní formy kyslíku MeSH
• rostlinné extrakty chemie   farmakologie   MeSH
• sérový albumin chemie   metabolismus   MeSH
• Solanum tuberosum chemie   MeSH
• vazba proteinů MeSH
• viabilita buněk účinky léků   MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• albuminy MeSH
• antioxidancia MeSH
• fytogenní protinádorové látky MeSH
• inhibitory cyklooxygenasy MeSH
• inhibitory lipoxygenas MeSH
• lipidy MeSH
• liposomy MeSH
• reaktivní formy kyslíku MeSH
• rostlinné extrakty MeSH
• sérový albumin MeSH

Based on the significant anti-inflammatory activity of natural quinone primin (5a), series of 1,4-benzoquinones, hydroquinones, and related resorcinols were designed, synthesized, characterized and tested for their ability to inhibit the activity of cyclooxygenase (COX-1 and COX-2) and 5-lipoxygenase (5-LOX) enzymes. Structural modifications resulted in the identification of two compounds 5b (2-methoxy-6-undecyl-1,4-benzoquinone) and 6b (2-methoxy-6-undecyl-1,4-hydroquinone) as potent dual COX/5-LOX inhibitors. The IC50 values evaluated in vitro using enzymatic assay were for compound 5b IC50 = 1.07, 0.57, and 0.34 μM and for compound 6b IC50 = 1.07, 0.55, and 0.28 μM for COX-1, COX-2, and 5-LOX enzyme, respectively. In addition, compound 6d was identified as the most potent 5-LOX inhibitor (IC50 = 0.14 μM; reference inhibitor zileuton IC50 = 0.66 μM) from the tested compounds while its inhibitory potential against COX enzymes (IC50 = 2.65 and 2.71 μM for COX-1 and COX-2, respectively) was comparable with the reference inhibitor ibuprofen (IC50 = 4.50 and 2.46 μM, respectively). The most important structural modification leading to increased inhibitory activity towards both COXs and 5-LOX was the elongation of alkyl chain in position 6 from 5 to 11 carbons. Moreover, the monoacetylation in ortho position of bromo-hydroquinone 13 led to the discovery of potent (IC50 = 0.17 μM) 5-LOX inhibitor 17 (2-bromo-6-methoxy-1,4-benzoquinone) while bromination stabilized the hydroquinone form. Docking analysis revealed the interaction of compounds with Tyr355 and Arg120 in the catalytic site of COX enzymes, while the hydrophobic parts of the molecules filled the hydrophobic substrate channel leading up to Tyr385. In the allosteric catalytic site of 5-LOX, compounds bound to Tyr142 and formed aromatic interactions with Arg138. Taken together, we identified optimal alkyl chain length for dual COX/5-LOX inhibition and investigated other structural modifications influencing COX and 5-LOX inhibitory activity.

• Klíčová slova
• 5-Lipoxygenase, Anti-inflammatory activity, Cyclooxygenase, Quinones, Resorcinols,
• MeSH
• benzochinony chemie   MeSH
• inhibitory cyklooxygenasy chemická syntéza   chemie   farmakologie   MeSH
• inhibitory lipoxygenas chemická syntéza   chemie   farmakologie   MeSH
• katalytická doména MeSH
• oxidace-redukce MeSH
• počítačová simulace MeSH
• resorcinoly chemie   MeSH
• simulace molekulového dockingu MeSH
• spektrální analýza metody   MeSH
• vztahy mezi strukturou a aktivitou MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• benzochinony MeSH
• inhibitory cyklooxygenasy MeSH
• inhibitory lipoxygenas MeSH
• quinone MeSH Prohlížeč
• resorcinol MeSH Prohlížeč
• resorcinoly MeSH

Stilbenoids represent a large group of bioactive compounds, which occur in food and medicinal plants. Twenty-five stilbenoids were screened in vitro for their ability to inhibit COX-1, COX-2 and 5-LOX. Piceatannol and pinostilbene showed activity comparable to the zileuton and ibuprofen, respectively. The anti-inflammatory potential of stilbenoids was further evaluated using THP-1 human monocytic leukemia cell line. Tests of the cytotoxicity on the THP-1 and HCT116 cell lines showed very low toxic effects. The tested stilbenoids were evaluated for their ability to attenuate the LPS-stimulated activation of NF-κB/AP-1. Most of the tested substances reduced the activity of NF-κB/AP-1 and later attenuated the expression of TNF-α. The effects of selected stilbenoids were further investigated on inflammatory signaling pathways. Non-prenylated stilbenoids regulated attenuation of NF-ĸB/AP-1 activity upstream by inhibiting the phosphorylation of MAPKs. A docking study used to in silico analyze the tested compounds confirmed their interaction with NF-ĸB, COX-2 and 5-LOX.

• Klíčová slova
• Anti-inflammatory, Cyclooxygenase, Lipoxygenase, Macrophages, Molecular docking simulations, NF-κB, Stilbenes,
• MeSH
• antiflogistika nesteroidní chemie   farmakologie   MeSH
• HCT116 buňky MeSH
• inhibitory cyklooxygenasy 2 chemie   farmakologie   MeSH
• inhibitory lipoxygenas chemie   farmakologie   MeSH
• lidé MeSH
• lipopolysacharidy farmakologie   MeSH
• makrofágy účinky léků   metabolismus   MeSH
• NF-kappa B metabolismus   MeSH
• preklinické hodnocení léčiv metody   MeSH
• prenylace MeSH
• signální transdukce účinky léků   MeSH
• simulace molekulového dockingu MeSH
• stilbeny chemie   farmakologie   MeSH
• TNF-alfa metabolismus   MeSH
• transkripční faktor AP-1 metabolismus   MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• 3,3',4,5'-tetrahydroxystilbene MeSH Prohlížeč
• antiflogistika nesteroidní MeSH
• inhibitory cyklooxygenasy 2 MeSH
• inhibitory lipoxygenas MeSH
• lipopolysacharidy MeSH
• NF-kappa B MeSH
• pinostilbene MeSH Prohlížeč
• stilbeny MeSH
• TNF-alfa MeSH
• transkripční faktor AP-1 MeSH

Neuroinflammation and cholinergic deficit are key detrimental processes involved in Alzheimer's disease. Hence, in the search for novel and effective treatment strategies, the multi-target-directed ligand paradigm was applied to the rational design of two series of new hybrids endowed with anti-inflammatory and anticholinesterase activity via triple targeting properties, namely able to simultaneously hit cholinesterases, cyclooxygenase-2 (COX-2) and 15-lipoxygenase (15-LOX) enzymes. Among the synthesized compounds, triazoles 5b and 5d, and thiosemicarbazide hybrid 6e emerged as promising new hits, being able to effectively inhibit human butyrylcholinesterase (hBChE), COX-2 and 15-LOX enzymes with a higher inhibitory potency than the reference inhibitors tacrine (for hBChE inhibition), celecoxib (for COX-2 inhibition) and both NDGA and Zileuton (for 15-LOX inhibition). In addition, compound 6e proved to be a submicromolar mixed-type inhibitor of human acetylcholinesterase (hAChE). The anti-neuroinflammatory activity of the three most promising hybrids was confirmed in a cell-based assay using PC12 neuron cells, showing decreased expression levels of inflammatory cytokines IL-1β and TNF-α. Importantly, despite the structural resemblance to tacrine, they showed ideal safety profiles on hepatic and murine brain cell lines and were safe up to 100 μM when assayed in PC12 cells. All three hybrids were also predicted to have superior BBB permeability than tacrine in the PAMPA assay, and good physicochemical properties, drug-likeness and ligand efficiency indices. Finally, molecular docking studies highlighted key structural elements impacting selectivity and activity toward the selected target enzymes. To the best of our knowledge, compounds 5b, 5d and 6e are the first balanced, safe and multi-target compounds hitting the disease at the three mentioned hubs.

• Klíčová slova
• 15-lipoxygenase, Acetylcholinesterase, Alzheimer's disease, Butyrylcholinesterase, Cyclooxygenase-2,
• MeSH
• acetylcholin nedostatek   MeSH
• Alzheimerova nemoc farmakoterapie   patologie   MeSH
• buněčné linie MeSH
• buňky PC12 MeSH
• cholinesterasové inhibitory chemie   MeSH
• inhibitory cyklooxygenasy 2 chemie   MeSH
• inhibitory lipoxygenas chemie   MeSH
• krysa rodu Rattus MeSH
• lidé MeSH
• myši MeSH
• neurony účinky léků   enzymologie   patologie   MeSH
• racionální návrh léčiv MeSH
• semikarbazidy chemie   farmakologie   MeSH
• simulace molekulového dockingu MeSH
• triazoly chemie   farmakologie   MeSH
• zánět farmakoterapie   MeSH
• zvířata MeSH
• Check Tag
• krysa rodu Rattus MeSH
• lidé MeSH
• myši MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• acetylcholin MeSH
• cholinesterasové inhibitory MeSH
• inhibitory cyklooxygenasy 2 MeSH
• inhibitory lipoxygenas MeSH
• semikarbazidy MeSH
• thiosemicarbazide MeSH Prohlížeč
• triazoly MeSH

A new series of 1,2-diaryl-4-substituted-benzylidene-5(4H)-imidazolone derivatives 4a-l was synthesized. Their structures were confirmed by different spectroscopic techniques (IR, 1 H NMR, DEPT-Q NMR, and mass spectroscopy) and elemental analyses. Their cytotoxic activities in vitro were evaluated against breast, ovarian, and liver cancer cell lines and also normal human skin fibroblasts. Cyclooxygenase (COX)-1, COX-2 and lipoxygenase (LOX) inhibitory activities were measured. The synthesized compounds showed selectivity toward COX-2 rather than COX-1, and the IC50 values (0.25-1.7 µM) were lower than that of indomethacin (IC50 = 9.47 µM) and somewhat higher than that of celecoxib (IC50 = 0.071 µM). The selectivity index for COX-2 of the oxazole derivative 4e (SI = 3.67) was nearly equal to that of celecoxib (SI = 3.66). For the LOX inhibitory activity, the new compounds showed IC50 values of 0.02-74.03 µM, while the IC50 of the reference zileuton was 0.83 µM. The most active compound 4c (4-chlorobenzoxazole derivative) was found to have dual COX-2/LOX activity. All the synthesized compounds were docked inside the active site of the COX-2 and LOX enzymes. They linked to COX-2 through the N atom of the azole scaffold, while CO of the oxazolone moiety was responsible for the binding to amino acids inside the LOX active site.

• Klíčová slova
• anti-inflammatory, cytotoxicity, diaryl imidazolone derivatives, molecular docking study,
• MeSH
• antiflogistika nesteroidní chemická syntéza   chemie   farmakologie   MeSH
• arachidonát-5-lipoxygenasa metabolismus   MeSH
• cyklooxygenasa 2 metabolismus   MeSH
• imidazoly chemická syntéza   chemie   farmakologie   MeSH
• inhibitory cyklooxygenasy 2 chemická syntéza   chemie   farmakologie   MeSH
• inhibitory lipoxygenas chemická syntéza   chemie   farmakologie   MeSH
• kultivované buňky MeSH
• lidé MeSH
• molekulární struktura MeSH
• racionální návrh léčiv * MeSH
• simulace molekulového dockingu MeSH
• viabilita buněk účinky léků   MeSH
• vztah mezi dávkou a účinkem léčiva MeSH
• vztahy mezi strukturou a aktivitou MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• antiflogistika nesteroidní MeSH
• arachidonát-5-lipoxygenasa MeSH
• cyklooxygenasa 2 MeSH
• imidazoly MeSH
• inhibitory cyklooxygenasy 2 MeSH
• inhibitory lipoxygenas MeSH

Geranyl flavones have been studied as compounds that potentially can be developed as anti-inflammatory agents. A series of natural geranylated flavanones was isolated from Paulownia tomentosa fruits, and these compounds were studied for their anti-inflammatory activity and possible mechanism of action. Two new compounds were characterized [paulownione C (17) and tomentodiplacone O (20)], and all of the isolated derivatives were assayed for their ability to inhibit cyclooxygenases (COX-1 and COX-2) and 5-lipoxygenase (5-LOX). The compounds tested showed variable degrees of activity, with several of them showing activity comparable to or greater than the standards used in COX-1, COX-2, and 5-LOX assays. However, only the compound tomentodiplacone O (20) showed more selectivity against COX-2 versus COX-1 when compared with ibuprofen. The ability of the test compounds to interact with the above-mentioned enzymes was supported by docking studies, which revealed the possible incorporation of selected test substances into the active sites of these enzymes. Furthermore, one of the COX/LOX dual inhibitors, diplacone (14) (a major geranylated flavanone of P. tomentosa), was studied in vitro to obtain a proteomic overview of its effect on inflammation in LPS-treated THP-1 macrophages, supporting its previously observed anti-inflammatory activity and revealing the mechanism of its anti-inflammatory effect.

• MeSH
• antiflogistika chemie   izolace a purifikace   farmakologie   MeSH
• arachidonát-5-lipoxygenasa metabolismus   MeSH
• cyklooxygenasa 1 metabolismus   MeSH
• cyklooxygenasa 2 metabolismus   MeSH
• flavonoidy chemie   izolace a purifikace   farmakologie   MeSH
• inhibitory cyklooxygenasy 2 chemie   izolace a purifikace   farmakologie   MeSH
• inhibitory lipoxygenas chemie   izolace a purifikace   farmakologie   MeSH
• Magnoliopsida chemie   MeSH
• molekulární struktura MeSH
• ovoce chemie   MeSH
• proteomika * MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• antiflogistika MeSH
• arachidonát-5-lipoxygenasa MeSH
• cyklooxygenasa 1 MeSH
• cyklooxygenasa 2 MeSH
• flavonoidy MeSH
• inhibitory cyklooxygenasy 2 MeSH
• inhibitory lipoxygenas MeSH

Two new series of N-substituted indole derivatives 4a-l and 5a-h were synthesized. Their chemical structures were confirmed using spectroscopic tools including IR, (1)H NMR, (13)C NMR mass spectroscopy and elemental analyses. The results showed no significant cytotoxic activity on either cancer or normal human cells. Anti-inflammatory activity for all target compounds was evaluated in vitro. Compounds 5a-h were found to have better anti-inflammatory activity than 4a-l. The inhibitory activity of COX-2 and 5-LOX were tested for 5a-h. Three compounds, 5c, 5d and 5f showed excellent COX-2 inhibitory activity with IC50 ranging from 0.98 to 1.23 μM compared to the reference celecoxib (1.54 μM). These compounds had a reasonable selectivity index between 7.03 and 8.05. Additionally, p-methylbenzoyl derivative 5g (IC50 = 5.78 μM) had superior 5-LOX inhibitory activity, higher than quercetin. 5e was close to quercetin in its LOX inhibitory activity. Compounds 5a-h were docked inside the active site of COX-2 and 5-LOX enzymes.

• Klíčová slova
• Anti-inflammatory activity, Antiproliferative activity, Cyclooxygenase enzymes, Indole derivatives, Molecular docking study,
• MeSH
• antiflogistika chemická syntéza   chemie   metabolismus   farmakologie   MeSH
• arachidonát-5-lipoxygenasa chemie   metabolismus   MeSH
• cyklooxygenasa 1 metabolismus   MeSH
• cyklooxygenasa 2 metabolismus   MeSH
• indoly chemická syntéza   chemie   metabolismus   farmakologie   MeSH
• inhibitory cyklooxygenasy 2 chemická syntéza   chemie   metabolismus   farmakologie   MeSH
• inhibitory lipoxygenas chemická syntéza   chemie   metabolismus   farmakologie   MeSH
• katalytická doména MeSH
• lidé MeSH
• nádorové buněčné linie MeSH
• protinádorové látky chemická syntéza   chemie   metabolismus   farmakologie   MeSH
• racionální návrh léčiv * MeSH
• Schiffovy báze chemie   MeSH
• simulace molekulového dockingu * MeSH
• techniky syntetické chemie MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• antiflogistika MeSH
• arachidonát-5-lipoxygenasa MeSH
• cyklooxygenasa 1 MeSH
• cyklooxygenasa 2 MeSH
• indoly MeSH
• inhibitory cyklooxygenasy 2 MeSH
• inhibitory lipoxygenas MeSH
• protinádorové látky MeSH
• Schiffovy báze MeSH

The induced differentiation of tumor cells into mature phenotypes is a promising strategy in cancer therapy. In this study, the effects of combined treatment with all-trans retinoic acid (ATRA) and lipoxygenase/cyclooxygenase inhibitors were examined in two osteosarcoma cell lines, Saos-2 and OSA-01. Caffeic acid and celecoxib were used as inhibitors of 5-lipoxygenase and of cyclooxygenase-2, respectively. Changes in the cell proliferation, matrix mineralization, and occurrence of differentiation markers were evaluated in treated cell populations at intervals. The results confirmed the capability of caffeic acid to enhance the antiproliferative effect of ATRA in both cell lines. In contrast, celecoxib showed the same effect in Saos-2 cells only. Furthermore, the extension of matrix mineralization was observed after combined treatment with ATRA and celecoxib or caffeic acid. The increased expression of osteogenic differentiation markers was observed in both cell lines after the combined application of ATRA and inhibitors. The obtained results clearly demonstrate the capability of lipoxygenase/cyclooxygenase inhibitors to enhance the antiproliferative and differentiating effect of ATRA in osteosarcoma cells, although some of these effects are specific and depend on the biological features of the respective tumor or cell line.

• MeSH
• buněčná diferenciace účinky léků   MeSH
• celekoxib MeSH
• inhibitory cyklooxygenasy farmakologie   MeSH
• inhibitory lipoxygenas farmakologie   MeSH
• kyseliny kávové farmakologie   MeSH
• lidé MeSH
• nádorové buněčné linie MeSH
• nádory kostí farmakoterapie   patologie   MeSH
• osteosarkom farmakoterapie   patologie   MeSH
• proliferace buněk účinky léků   MeSH
• protinádorové látky farmakologie   MeSH
• pyrazoly farmakologie   MeSH
• sulfonamidy farmakologie   MeSH
• tretinoin farmakologie   MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• caffeic acid MeSH Prohlížeč
• celekoxib MeSH
• inhibitory cyklooxygenasy MeSH
• inhibitory lipoxygenas MeSH
• kyseliny kávové MeSH
• protinádorové látky MeSH
• pyrazoly MeSH
• sulfonamidy MeSH
• tretinoin MeSH

Quinones are compounds frequently contained in medicinal plants used for the treatment of inflammatory diseases. Therefore, the impact of plant-derived quinones on the arachidonic acid metabolic pathway is worthy of investigation. In this study, twenty-three quinone compounds of plant origin were tested in vitro for their potential to inhibit leukotriene B4 (LTB4) biosynthesis in activated human neutrophil granulocytes with 5-lipoxygenase (5-LOX) activity. The benzoquinones primin (3) and thymohydroquinone (4) (IC50 = 4.0 and 4.1 microM, respectively) showed activity comparable with the reference inhibitor zileuton (1C50 = 4.1 microM). Moderate activity was observed for the benzoquinone thymoquinone (2) (1C50 = 18.2 microM) and the naphthoquinone shikonin (1) (IC50 = 24.3 microM). The anthraquinone emodin and the naphthoquinone plumbagin (5) displayed only weak activities (IC50 > 50 microM). The binding modes of the active compounds were further evaluated in silico by molecular docking to the human 5-LOX crystal structure. This process supports the biological data and suggested that, although the redox potential is responsible for the quinone's activity on multiple targets, in the case of 5-LOX the molecular structure plays a vital role in the inhibition. The obtained results suggest primin as a promising compound for the development of dual COX-2/5-LOX inhibitors.

• MeSH
• antiflogistika analýza   MeSH
• benzochinony farmakologie   MeSH
• chinony farmakologie   MeSH
• inhibitory cyklooxygenasy 2 analýza   MeSH
• inhibitory lipoxygenas analýza   MeSH
• léčivé rostliny chemie   MeSH
• leukotrien B4 antagonisté a inhibitory   biosyntéza   MeSH
• lidé MeSH
• neutrofily účinky léků   metabolismus   MeSH
• preklinické hodnocení léčiv MeSH
• rostlinné extrakty chemie   farmakologie   MeSH
• simulace molekulového dockingu MeSH
• thymol analogy a deriváty   farmakologie   MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• antiflogistika MeSH
• benzochinony MeSH
• chinony MeSH
• inhibitory cyklooxygenasy 2 MeSH
• inhibitory lipoxygenas MeSH
• leukotrien B4 MeSH
• primin MeSH Prohlížeč
• rostlinné extrakty MeSH
• thymohydroquinone MeSH Prohlížeč
• thymol MeSH