In our ongoing search for bioactive compounds originating from the endemic species in Korea, we found that the hexane and EtOAc fractions of the MeOH extract from the root of Dystaenia takeshimana (Nakai) Kitagawa (Umbelliferae) showed cyclooxygenase-2 (COX-2) and 5- lipoxygenase (5-LOX) dual inhibitory activity by assessing their effects on the production of prostaglandin $D_2\;(PGD_2)$ and leukotriene $C_4\;(LTC_4)$ in mouse bone marrow-derived mast cells. By activity-guided fractionation, five coumarins, viz. psoralen (2), xanthotoxin (3), scopoletin (4), umbelliferone (5), and (+)-marmesin (6), together with ${\beta}-sitosterol$ (1), were isolated from the hexane fraction, and two phenethyl alcohol derivatives, viz. 2-methoxy-2-(4'-hydroxyphenyl)ethanol (7) and 2-hydroxy-2-(4'-hydroxyphenyl)ethanol (8), three flavonoids, viz. apigenin (9), luteolin (10), and cynaroside (11), as well as daucosterol (12) were isolated from the EtOAc fraction using silica gel column chromatography. In addition, D-mannitol (13) was isolated from the BuOH fraction by recrystallization. Two of the coumarins, scopoletin (4) and (+)- marmesin (6), the two phenethyl alcohol derivatives (7, 8) and the three flavonoids (9-11) were isolated for the first time from this plant. Among the compounds isolated from this plant, the five coumarins as well as the three flavonoids showed COX-2/5-LOX dual inhibitory activity. These results suggest that the anti-inflammatory activity of D. takeshimana might in part occur via the inhibition of the generation of eicosanoids.
Conjugated linoleic acid (CLA) is the mixture of positional and geometric isomers of linoleic acid (LA), which is found abundantly in dairy products and meats. This study was performed to investigate the anticarcinogenic effect of CLA in HepG2 hepatoma cells. HepG2 cell were treated with LA and CLA at the various concentrations of 10, 20, 40, 80 uM each at different incubation times. After each incubation times, cell proliferation, fatty acids incorporation into cell, peroxidation and postaglandin E$_2$ (PGE$_2$) and thromboxane $A_2$ (TXA$_2$) for the eicosanoid metabolism were measured. LA treated HepG2 cells were increased cell growth 6 - 70% of control whereas CLA increased cell death the half of those in LA group (p 〈 0.001). LA and CLA were incorporated very well into the cellular membranes four times higher than in control according to concentration and longer incubation times. Moreover, LA synthesized significantly arachidonic acids corresponding with LA concentration compared to CLA supplementation. The supplementation with LA increased intracellular lipid peroxides concentration corresponding with LA concentration and five times higher than those in CLA significantly at any incubation times (p 〈 0.001). PGE$_2$ and TXA$_2$ levels were three to twenty times lower in condition of CLA treatments than LA, respectively. Overall, the dietary CLA might change the HepG2 cell growth by the changes of cell composition, production of lipid peroxide. Since CLA have not changed the levels of arachidonic acid of cell membrane, which was sources of eicosanoids, eicosanoid synthesis was not increased in CLA compared to LA. Our results was suggest CLA has a possibility to protect the progress of atherosclerosis because CLA does not produce lipid production and endothelial contraction factors in liver.
Tumor necrosis factor alpha (TNF-α) is a principal regulator of inflammation and immunity. The proinflammatory properties of TNF-α can be attributed to its ability to activate the enzyme cytosolic phospholipase A2 (cPLA2), which generates potent inflammatory lipid mediators, eicosanoids. L-glutamine (Gln) plays physiologically important roles in various metabolic processes. We have reported that Gln has a potent anti-inflammatory activity via rapid upregulation of mitogen-activated protein kinases (MAPKs) phosphatase (MKP)-1, which preferentially dephosphorylates the key proinflammatory enzymes, p38 MAPK and cytosolic phospholipase A2 (cPLA2). In this study, we have investigated whether Gln could inhibit TNF-α-induced cPLA2 activation. Gln inhibited TNF-α-induced increases in cPLA2 phosphorylation in the lungs and blood levels of the cPLA2 metabolites, leukotrine B4 (LTB4) (lipoxygenase metabolite) and prostaglandin E2 (PGE2) (cyclooxygenase metabolite). TNF-α increased p38 and cPLA2 phosphorylation and blood levels of LTB4 and PGE2, which were blocked by the p38 inhibitor SB202190. Gln inhibited TNF-α-induced p38 and cPLA2 phosphorylation and production of the cPLA2 metabolites. Such inhibitory activity of Gln was no longer observed in MKP-1 small interfering RNA-pretreated animals. Our data indicate that Gln inhibited TNF-α-induced cPLA2 phosphorylation through MKP-1 induction/p38 inhibition, and suggest that the utility of Gln in inflammatory diseases in which TNF-α plays a major role in their pathogenesis.
Kim, Su Jeong;Choi, Min Yeong;Min, Keun Young;Jo, Min Geun;Kim, Jie Min;Kim, Hyung Sik;Kim, Young Mi
Biomolecules & Therapeutics
/
v.30
no.6
/
pp.520-528
/
2022
Mast cells are an effector cell that plays a pivotal role in type I hypersensitive immune responses. Mast cells exist in connective tissues, such as skin and mucosal tissue, and contain granules which contain bioactive substances such as histamine and heparin in cells. The granules of mast cells are secreted by antigen stimulation to cause the type I allergic hypersensitivity. In addition, stimulated by antigen, mast cells synthesize and secrete various eicosanoids and cytokines. While AT9283 is known to have anticancer effects, the therapeutic effect of AT9283 on allergic disorders is completely unknown. In this study, it was found that AT9283 reversibly inhibited antigen-IgE binding-induced degranulation in mast cells (IC50, approx. 0.58 μM) and suppressed the secretion of the inflammatory cytokines IL-4 (IC50, approx. 0.09 μM) and TNF-α (IC50, approx. 0.19 μM). For a mechanism of mast cell inhibition, while not inhibiting Syk phosphorylation, AT9283 suppressed the activation of LAT, a downstream substrate protein of Syk, in a dose-dependent manner. As expected, AT9283 also inhibited the activation of PLCγ1 and Akt, downstream signaling molecules of Syk/LAT, and MAP kinases such as JNK, Erk1/2, and P38. In an in vitro protein tyrosine kinase assay, AT9283 directly inhibited Syk activity. Next, AT9283 dose-dependently inhibited passive cutaneous anaphylaxis (PCA), an IgE-mediated allergic acute response, in mice (ED50, approx. 34 mg/kg, p.o.). These findings suggest that AT9283 has potential to use as a new drug for alleviating the symptoms of IgE-mediated allergic disorders.
Effects of various combinations of corn oil (CO) and perilla oil (PO) as respective dietary sources of ${\omega}$-6 and ${\omega}$-3 polyunsaturated fatty acids on fatty acid profiles of immune organs were studied in young chicks. Seventy-five 1-day-old male (ISA Brown) chicks were assigned to five treatments with three replications. Semi-purified-type diets containing glucose and soybean meal as major ingredients were added with 8% CO, 6% CO+2% PO, 4% CO+4% PO, 2% CO+6% PO and 8% PO and fed for 7 weeks. There were no significant differences in body weight gain, feed intake and relative weights of liver and immune organs (g/100g weight) among dietary groups. Dietary fatty acid patterns were generally reflected in the fatty acid compositions of all immune organs such as spleen, thymus and bursa of Fabricius. The levels of a-linolenic acid(LNA), eicosapentaenoic acid (EPA) and docosahexaenoic acid in various immune organs increased with increasing levels of perilla oil in the diets, whilet the levels of linoleic acid (LA) and arachidonic acid (AA) decreased. Thymus appeared to have capacity to retain remarkably higher (P<0.05) levels of LA and LNA up to 37 and 22%, respectively, compared to the other organs. Thymic tissue contained ${\omega}$-3 fatty acid and ${\omega}$-6 fatty acid 10~36 times and 3~5 times higher than the other organs, respectively. Spleen tissue was specifically higher (P<0.05) in the levels of AA and EPA and the ratios of AA/LA and EPA/LNA, compared to the other organs, suggesting that the tissue might have high desaturase activity to convert LA or LNA to AA or EPA, respectively. BSA antibody production tended to increase by 18 ~ 32% with higher levels of perilla oil in diet, although the increase was not statistically significant. In conclusion, fatty acid compositions of immune organs very depending on the lipid composition of the diets and each organ appears to respond differently for its fatty acid profile to dietary lipids. Considering AA and EPA are precursors of many important eicosanoids, further studies are required to clarify the responses of the immune organs to the dietary fatty acids.
Entomopathogenic fungus, Paecilomyces japonicus, has been commercially used as medicinal purpose . The silkworm, Bombyx mori, as an optimal host for the fungi, has been selected and used for the production of the fungal fruit bodies. In current method, newly molted fifth instal larvae should be exposed to the adverse stress environment of high temperature (3$0^{\circ}C$), high relative humidity ( 90%), and starvation for 24h for better fungal inoculation to the host insects. In this study, an alternative method using chemical agent, dexamethasone (DEX: an eicosanoid biosynthesis inhibitor), was tried to get the immunodepressive effect on the larvae to elevate the inoculation rate of the fungi to the silkworm without any harsh rearing environment. DEX (100$\mu\textrm{g}$) showed significantly synergistic effect on the hemocyte lethality of the fungus, and was effective to decrease cellular immune responses measured by the number of hemocyte microaggregation and phenoloxidase activity of the fifth instar larvae in response to the fungal injection. A detergent of 0.05% Triton-X was effective to increase the in- oculation rate of the fungi to the larvae and used in all fungal spraying solutions. Without any environ- mental stress treatment, only DEX (100$\mu\textrm{g}$) injection to the fifth instar larvae followed by the fungal spray was effective to get the inoculation rate equivalent to the current fungal spray method requiring harsh rearing environment. These results suggest that the inoculation of P. japonicus can be elevated by the help of DEX and that the silkworms use eicosanoids to elicit cellular immune response against fungal pathogen.
To compare the effect of three kinds of n-3 fatty acids-eicosapentaenoic acid(EPA), docosahexaenoic acid(DHA) and perilla oil (PO)-on serum and liver lipid levels and fatty acid composition of liver phospholipid(PL) at low fat level(5%, w/w), 4-weeks old Sprague-Dawley rats were fed with one of five different oil diets for 4 weeks. Beef tallow(BT) and corn oil(CO) was used as control for sturated or n-6 fatty acid respectively. Se겨m concentrations of cholesterol(TC) and phospholipid(PL) were lower in PO DHA and EPA groups than in BT and CO groups. HDL-cholesterol levels were higher in CO and PO groups than in EPA, DHA and BT groups. Liver PL concentrations were higher in DHA and EPA groups than in CO, PO and BT groups, but liver TC and heal PL and TC concentrations did not show any significant difference among groups. Hepatic fatty acid composition of phosphatidylcholine (PC) and phosphatidylethanolamine (PE), two major phospholipids in liver, reflected their dietary fatty acid composition. In PC and PE, total percentage own-6 series was higher in CO group than in any other groups, and that own-3 series was higher in DHA and PO groups than in EPA, CO and BT groups. Moreover, the ratio of 20 : 4/18 : 2 was lower in PO and DHA groups than in EPA, CO and BT groups. On the contrary, the percentage of C22 : 6 was lower in EPA, CO and BT groups than in PO and DHA groups. These results revealed that n-3 series(EPA, DHA and PO) were more effective in lowering um lipids than n-6 fatty acids or saturated fatty acid. Based on the results of fatty acid composition of hepatic phospholipid, we suggest that the dietary effect of PO and DHA on antiatherogenic characteristics seems to be similar extent. In addition, the effect of EPA might not be significantly different from that of BT or CO in the view of eicosanoids production from the precursor fatty acid. These difference of hepatic fatty acid composition might come from other characteristics of dietary oil as well as the type of unsaturation, not from the carbon chain length or the degree of unsaturation of n-3 fatty acid.
Park, Ye-Sol;Kim, Min-Je;Lee, Geon-Hyung;Chun, Won-Soo;Yi, Young-Keun;Kim, Yong-Gyun
The Korean Journal of Pesticide Science
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v.13
no.3
/
pp.185-189
/
2009
A monoterpenoid compound, benzylideneacetone (BZA), is a metabolite of an entomopathogenic bacterium, Xenorhabdus nematophila. Its primary biological activity is an inhibitor of phospholipase $A_2$, which catalyzes the committed step of biosynthesis of various eicosanoids that are critically important to mediate insect immune responses. When BZA was applied to two-spotted spider mite, Tetranychus urticae, it exhibited a dose-dependent mortality in leaf-disc assay. Subsequently BZA was tested against T. urticae infesting apples in a field orchard, in which it showed a significant control efficacy, which was not statistically different with that of a commercial acaricide. BZA also had significant antibacterial activities against three species of plant pathogenic bacteria when it was added to the bacterial cultures, in which it showed the highest inhibitory activity against a bacterial wilt-causing pathogen, Ralstonia solanacearum. The bacterial pathogen caused significant disease symptom to young potato plants. However, BZA significantly suppressed the disease occurrence. This study suggests that BZA can be used to develop a novel crop protectant to control mite and bacterial pathogen.
Seo, Hae-Ryun;Ahn, Changhwan;Kang, Byeong-Teck;Kang, Ji-Houn;Jeung, Eui-Bae;Yang, Mhan-Pyo
Journal of Veterinary Clinics
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v.33
no.4
/
pp.194-199
/
2016
The objective of this study was to examine the effect of trans-10, cis-12 conjugated linoleic acid (t10c12-CLA) on the expression of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) pathway in lipopolysaccharide (LPS)-stimulated porcine peripheral blood mononuclear cells (PBMCs). t10c12-CLA was treated with different concentrations in culture medium of LPS$na{\ddot{i}}ve$ and LPS-stimulated PBMCs. The mRNA expressions of prostaglandin $E_2$ ($PGE_2$)-synthase, COX-2 and 5-LOX were measured using quantitative real-time PCR. In addition, the production levels of $PGE_2$ and 5-LOX in culture supernatant from PBMCs with or without LPS were assessed by ELISA. In LPS$na{\ddot{i}}ve$ PBMCs, treatment of t10c12-CLA significantly (p < 0.05) increased the mRNA expressions of PGE2 synthase and 5-LOX compared to vehicle control. Expression of COX-2 mRNA did not show significant difference compared to vehicle control by t10c12-CLA treatment in LPS$na{\ddot{i}}ve$ PBMCs. However, the addition of LPS in PBMCs markedly (p < 0.05) increased the mRNA expression of COX-2, $PGE_2$ synthase and 5-LOX, and also significantly (p < 0.05) enhanced the production of $PGE_2$ and 5-LOX relative to LPS$na{\ddot{i}}ve$ PBMCs, respectively. However, the addition of t10c12-CLA significantly (p < 0.01) suppressed the LPS-induced excessive expression of COX-2, $PGE_2$ synthase, and 5-LOX compared to those of PBMCs treated with LPS alone. The production levels of $PGE_2$ and 5-LOX in culture supernatant from LPS-stimulated PBMCs were also significantly (p < 0.05) inhibited by the treatment of t10c12-CLA compared to LPS alone. These results suggested that t10c12-CLA has an anti-inflammatory effect via dual inhibition of COX-2 and 5-LOX with gene expression and production level in LPS-stimulated porcine PBMCs. Therefore, it was thought that t10c12-CLA can attenuate the inflammatory response by down-regulation of eicosanoids production.
Journal of the Korean Society of Food Science and Nutrition
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v.36
no.10
/
pp.1279-1286
/
2007
We investigated the effects of conjugated linoleic acid (CLA) on the fatty acid composition in the plasma and liver, and the expressions of delta-5 desaturase (D5D) and fatty acid desaturase2 (FADS2) genes in ICR male mice using two different sources of fats in the diets. The experimental groups were divided into four groups: beef tallow (BT) and fish oil (FO), BT with CLA supplementation (BTC), and FO with CLA supplementation (FOC) groups. Ten mice in each group were fed with the experimental diets for 4 weeks. All mice were fed experimental diets containing 12% of total dietary fat (w/w) either with or without 0.5% CLA (w/w). Fatty acid compositions were analyzed in the plasma and liver using gas chromatography. The levels of D5D and FADS2 expression were analyzed by RT-PCR in the liver The results showed that CLA participates competitively with C18:2 in the elongation and desaturation processes, leading to significant increase in the levels of C20:4 and C22:6 in BTC group (p<0.05). The expression levels of D5D and FADS2 were higher in BT and BTC group than those of FO and FOC group. In particular, the expression of D5D gene was greatly upregulated in BTC group. Furthermore, the conversion ratios from C18:2 to C20:4 in the liver were higher in BTC group than those in other groups. Thus our results suggest that increased expressions of DSD and FADS2 genes may be responsible for the enhanced CLA effects on the desaturation in the BT containing saturated fatty acids rather than the FO rich in n-3 PUFA.
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