In vitro inhibition of mouse epidermal cell lipoxygenase by flavonoids: structure—activity relationships

Wheeler, Edward L.; Berry, David L.

doi:10.1093/carcin/7.1.33

Cited by 26 publications

(15 citation statements)

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“…Their effects on bacteria-derived enzymes is less well documented. Flavones and flavonols, which possess the C2-C3 double bond [Wheeler and Berry, 1986;Ferriola et al, 1989;Merlos et al, 1991;Eaton et al, 1996], have been considered the main flavonoids related to the inhibition of enzymes. Among them, quercetin, galangin, kaempferol, kaempferide (flavonols) and chrysin, apigenin, and acacetin (flavones) were identified in the EEPs tested in the present study Koo et al, 1999].…”

Section: Discussionmentioning

confidence: 99%

Effects of Apis mellifera Propolis on the Activities of Streptococcal Glucosyltransferases in Solution and Adsorbed onto Saliva–Coated Hydroxyapatite

et al. 2000

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Propolis, a resinous hive product collected by Apis mellifera bees, has been used for thousands of years in folk medicine. Ethanolic extracts of propolis (EEP) have been shown to inhibit the activity of a mixture of crude glucosyltransferase (Gtf) enzymes in solution. These enzymes synthesize glucans from sucrose, which are important for the formation of pathogenic dental plaque. In the present study, the effects of propolis from two different regions of Brazil on the activity of separate, purified Gtf enzymes in solution and on the surface of saliva–coated hydroxyapatite (sHA) beads were evaluated. The EEP from Minas Gerais (MG; Southeastern Brazil) and Rio Grande do Sul (RS; Southern Brazil) were tested for their ability to inhibit the enzymes GtfB (synthesis of insoluble glucan), GtfC (insoluble/soluble glucan) and GtfD (soluble glucan). The effects of propolis on Gtf from Streptococcus sanguis (soluble glucan synthesis) was also explored. The EEP from both regions effectively inhibited the activity of all Gtfs in solution (75–95%) and on the surface of sHA beads (45–95%) at concentrations between 0.75 and 3.0 mg of propolis/ml. However, the two samples of propolis showed different levels of inhibition on each of the enzymes tested. In general, EEP RS demonstrated a significantly higher inhibitory activity on GtfB and C activities (both solution and surface assays) than EEP MG at concentrations between 0.047 and 0.187 mg/ml (p<0.05). EEP MG, on the other hand, exhibited a greater inhibitory effect on the activities of surface GtfD (at 0.375, 0.75 and 1.5 mg/ml) and S. sanguis Gtf (at 1.5 and 3.0 mg/ml; p<0.05). These data indicate that EEP is a potent inhibitor of Gtf enzymes in solution and adsorbed on an experimental pellicle; however, its effect on Gtf activity is variable depending on the geographical origin of the propolis samples. There is a need to identify the active compounds of propolis.

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Section: Discussionmentioning

confidence: 99%

Effects of Apis mellifera Propolis on the Activities of Streptococcal Glucosyltransferases in Solution and Adsorbed onto Saliva–Coated Hydroxyapatite

et al. 2000

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“…Flavones and flavonols, which have an unsaturated double bond between positions C-2 and C-3 (Table 1), showed remarkable inhibition of GTF activity; in contrast, flavanones and dihydroflavonols, which lack a double bond between C-2 and C-3, exhibited only modest inhibitory activities. Results from previous studies have shown that flavones and flavonols are the main flavonoids related to inhibition of several mammalian enzymes, which suggests that a double bond between C-2 and C-3 is required for inhibitory effects (15,52). The presence of a double bond between C-2 and C-3 may provide a site for nucleophilic addition by side chains of amino acids in GTFs.…”

Section: Vol 46 2002 Biological Effects Of Propolis Compounds 1305mentioning

confidence: 98%

Effects of Compounds Found in Propolis onStreptococcus mutansGrowth and on Glucosyltransferase Activity

Koo

Rosalen²,

Cury³

et al. 2002

Antimicrob Agents Chemother

297

246

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Propolis, a resinous bee product, has been shown to inhibit the growth of oral microorganisms and the activity of bacterium-derived glucosyltransferases (GTFs). Several compounds, mainly polyphenolics, have been identified in this natural product. The present study evaluated the effects of distinct chemical groups found in propolis on the activity of GTF enzymes in solution and on the surface of saliva-coated hydroxyapatite (sHA) beads. Thirty compounds, including flavonoids, cinnamic acid derivatives, and terpenoids, were tested for the ability to inhibit GTFs B, C, and D from Streptococcus mutans and GTF from S. sanguinis (GTF Ss). Flavones and flavonols were potent inhibitors of GTF activity in solution; lesser effects were noted on insolubilized enzymes. Apigenin, a 4,5,7-trihydroxyflavone, was the most effective inhibitor of GTFs, both in solution (90.5 to 95% inhibition at a concentration of 135 g/ml) and on the surface of sHA beads (30 to 60% at 135 g/ml). Antibacterial activity was determined by using MICs, minimum bactericidal concentrations (MBCs), and time-kill studies. Flavanones and some dihydroflavonols, as well as the sesquiterpene tt-farnesol, inhibited the growth of S. mutans and S. sobrinus; tt-farnesol was the most effective antibacterial compound (MICs of 14 to 28 g/ml and MBCs of 56 to 112 g/ml). tt-Farnesol (56 to 112 g/ml) produced a 3-log-fold reduction in the bacterial population after 4 h of incubation. Cinnamic acid derivatives had negligible biological activities. Several of the compounds identified in propolis inhibit GTF activities and bacterial growth. Apigenin is a novel and potent inhibitor of GTF activity, and tt-farnesol was found to be an effective antibacterial agent.

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“…The effect of n-PG, NDGA and SHAM was related to their antioxidant activity; these compounds are supposed to act as free radical scavengers, inhibiting all types of oxygenases. Flavonoid compounds such as esculetin (6,7-dihydroxycoumarin), quercetin (3,3',4',5,7-pentahydroxyflavone) and flavonol (3-hydroxyflavone) have been reported to inhibit lipoxygenase and cyclooxygenase in animal cells (Wheeler and Berry, 1986) with a strong structure-activity relationship. Only esculetin and quercetin inhibited tobacco lipoxygenase; the same specificities have been reported for soybean lipoxygenase (Wheeler and Berry, 1986).…”

Section: Characterization Of Lipoxygenase Inhibitorsmentioning

confidence: 99%

“…Flavonoid compounds such as esculetin (6,7-dihydroxycoumarin), quercetin (3,3',4',5,7-pentahydroxyflavone) and flavonol (3-hydroxyflavone) have been reported to inhibit lipoxygenase and cyclooxygenase in animal cells (Wheeler and Berry, 1986) with a strong structure-activity relationship. Only esculetin and quercetin inhibited tobacco lipoxygenase; the same specificities have been reported for soybean lipoxygenase (Wheeler and Berry, 1986). Anti-inflammatory drugs such as indomethacin, salicylic acid, ibuprofen, mefenamic acid and piroxicam, which inhibit cyclooxygenase enzymes and soybean lipoxygenase (Sircar et al, 1983), did not inhibit tobacco lipoxygenase, even at concentrations much higher than the lCso reported for soybean lipoxygenase.…”

Section: Characterization Of Lipoxygenase Inhibitorsmentioning

confidence: 99%

Purification and characterization of elicitor‐induced lipoxygenase in tobacco cells

et al. 1993

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SummaryLipoxygenase activity was induced in a tobacco cell suspension culture by treatment with glycopeptide elicitors prepared from the cell walls of Phytophthora parasitica var, nicotianae, and in tobacco seedlings infected by this fungal pathogen. Upon purification and characterization, the enzyme appeared to have a molecular weight of 96000, a pl of 5.1 and a Km of 20.9 μM with linoleic acid as substrate. According to its acidic optimum pH, it belongs to type‐2 lipoxygenases. Using linoleic, linolenic and arachidonic acids as substrates, the products formed in vitro by lipoxygenase were characterized. 9‐ and 5‐hydroperoxides were the main products obtained from the C18 and C20 fatty acids, respectively, thereby indicating that a 5‐lipoxygenase accounts for most of the elicitor‐induced activity, since the main site of insertion of molecular oxygen is on C‐5 of arachidonic acid. Small amounts of 13‐hydroperoxides were also formed from the C18 fatty acids. In vitro, the strongest inhibitors of tobacco lipoxygenase were n‐propylgallate and nordihydroguaiaretic acid. The possible involvement of this enzyme in signaling phenomena leading to defense induction in plants via jasmonic acid and other fatty acid‐derived products is discussed.

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In vitro inhibition of mouse epidermal cell lipoxygenase by flavonoids: structure—activity relationships

Cited by 26 publications

References 0 publications

Effects of <i>Apis mellifera</i> Propolis on the Activities of Streptococcal Glucosyltransferases in Solution and Adsorbed onto Saliva–Coated Hydroxyapatite

Effects of <i>Apis mellifera</i> Propolis on the Activities of Streptococcal Glucosyltransferases in Solution and Adsorbed onto Saliva–Coated Hydroxyapatite

Effects of Compounds Found in Propolis onStreptococcus mutansGrowth and on Glucosyltransferase Activity

Purification and characterization of elicitor‐induced lipoxygenase in tobacco cells

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