Effects of chalcone derivatives on lipoxygenase and cyclooxygenase activities of mouse epidermis

Nakadate, Teruo; Aizu, Eriko; Yamamoto, Shozo; Kato, Ryuichi

doi:10.1016/0090-6980(85)90112-1

Cited by 33 publications

(23 citation statements)

References 20 publications

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“…Interestingly, staurosporine alone (10 nM final concentration) was found to inhibit PMN transepithelial migration (93±5% inhibition vs vehicle control, n = 3, P < 0.001 ). These data were also confirmed using the PKC inhibitor H7 (33) (100 ,M final concentration, 91±4% inhibition compared to vehicle control, n = 3, P < 0.001 ). Likewise, the LXA4-elicited (10 nM) increment in transmigration was sensitive to staurosporine (89±7% inhibition compared to vehicle control, n = 3, P < 0.001).…”

Section: Introductionsupporting

confidence: 61%

Lipoxin A4 modulates transmigration of human neutrophils across intestinal epithelial monolayers.

Colgan

Serhan²,

Parkos³

et al. 1993

J. Clin. Invest.

210

143

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Neutrophil (PMN) migration across intestinal epithelial barriers, such as occurs in many disease states, results in modifications in epithelial barrier. Here, we investigated the impact of lipoxin A4 (LXA4), an eicosanoid with counterregulatory inflammatory roles, on PMN migration across cultured monolayers of the human intestinal epithelial cell line T84. Transepithelial migration of PMN was assessed in the apical-to-basolateral direction and in the basolateral-to-apical direction. In the apical-to-basolateral direction, preexposure of PMN to LXA4 (10 nM, 15 min) stimulated an 87±5% increase in transepithelial migration of PMN as determined by a PMN myeloperoxidase assay. The LXA4-elicited effect on transmigration was present throughout the 2-h assay period and was not secondary to LXA4 effects on epithelial monolayer integrity as judged by measurement of transepithelial resistance. PMN migration in the basolateral-to-apical direction was modulated by LXA4 with a comparable time-and concentration-dependence to that in the apical-to-basolateral direction. However, qualitative differences in how LXA4 modulates transmigration in the two opposing directions were observed. In the basolateral-to-apical direction, preexposure of PMN to LXA4 (10 nM, 15 min) diminished PMN transepithelial migration by 33±4%. Structure-function studies revealed that LXA4 and 1 1-trans-LXA4 (50% of LXA4 effect), but not LXB4, inhibited basolateral-toapical PMN transmigration. The action of LXA4 was not sensitive to inhibitors of cyclooxygenase or specific leukotriene biosynthesis, but was sensitive to staurosporine, a protein kinase C inhibitor. These results suggest that migration of PMN across epithelia in the physiological direction may be qualitatively different following PMN exposure to eicosanoids. We propose that such retention of PMN at this specific anatomic location may serve an important role in mucosal defense. (J. Clin. Invest. 1993. 92:75-82.)

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Section: Introductionsupporting

confidence: 61%

Lipoxin A4 modulates transmigration of human neutrophils across intestinal epithelial monolayers.

Colgan

Serhan²,

Parkos³

et al. 1993

J. Clin. Invest.

210

143

View full text Add to dashboard Cite

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“…Some chalcones having a 3,4-dihydroxycinnamoyl moiety (Fig. 2) were reported to inhibit COX and 12-LOX from mouse epidermis, being more active on LOX (21). While some flavonoid glycosides including rutin and hypolaetin-8-glucoside rather enhanced COX activity from sheep seminal vesicle (22), certain flavonoids such as flavone, kaempferol, and quercetin were repeatedly found to be COX inhibitors from rat peritoneal macrophages (8).…”

Section: Cellular Action Mechanismsmentioning

confidence: 99%

Anti-inflammatory Plant Flavonoids and Cellular Action Mechanisms

et al. 2004

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Abstract. Plant flavonoids show anti-inflammatory activity in vitro and in vivo. Although not fully understood, several action mechanisms are proposed to explain in vivo anti-inflammatory action. One of the important mechanisms is an inhibition of eicosanoid generating enzymes including phospholipase A 2 , cyclooxygenases, and lipoxygenases, thereby reducing the concentrations of prostanoids and leukotrienes. Recent studies have also shown that certain flavonoids, especially flavone derivatives, express their anti-inflammatory activity at least in part by modulation of proinflammatory gene expression such as cyclooxygenase-2, inducible nitric oxide synthase, and several pivotal cytokines. Due to these unique action mechanisms and significant in vivo activity, flavonoids are considered to be reasonable candidates for new anti-inflammatory drugs. To clearly establish the therapeutic value in inflammatory disorders, in vivo anti-inflammatory activity, and action mechanism of varieties of flavonoids need to be further elucidated. This review summarizes the effect of flavonoids on eicosanoid and nitric oxide generating enzymes and the effect on expression of proinflammatory genes. In vivo anti-inflammatory activity is also discussed. As natural modulators of proinflammatory gene expression, certain flavonoids have a potential for new anti-inflammatory agents.

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“…Isoliquiritigenin does not inhibit COX activity, however, it does suppress 5-lipoxygenase (LOX) activity. 24,25) These facts suggest that both COX and LOX may be involved in colorectal tumorigenesis.…”

Section: Fig 2 Experimental Protocol Of Colonic Carcinogenesis In Dmentioning

confidence: 99%

Studies on Cancer Chemoprevention by Traditional Folk Medicines XXV. Inhibitory Effect of Isoliquiritigenin on Azoxymethane-Induced Murine Colon Aberrant Crypt Focus Formation and Carcinogenesis.

Baba

Asano

Takigami

et al. 2002

Biological & Pharmaceutical Bulletin

101

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Licorice, the roots and long-stalks of various species of Glycyrrhiza genus, has been used as a traditional folk medicine and foodstuff all over the world.2) Isoliquiritigenin is one of the plant pigments of licorice, and is a simple chalcone derivative, 4,2Ј,4Ј-trihydroxy-chalcone (see Fig. 1). We have reported the isolation of this compound from Egyptian licorice (Glycyrrhiza grabla), along with new and known 3-arylcoumarins.3) Shibata reported the anti-tumor promoter effects of various chalcone derivatives in vitro, and isoliquiritigenin exhibited potential activity. 4) Other biological activities for this compound have also been reported. For example, antitumor promoting activity on two-stage mouse skin carcinogenesis, 5) inhibitory effect on aldose reductase activity, 6) antiplatelet aggregation effect, 7) antioxidative and superoxide scavenging activities, 8) etc. However, all these experiments were in vitro or topical application in vivo, and there is no reported data of the effect by oral administration in vivo.Repetitive treatment with the organotropic colon carcinogen, azoxymethane (AOM), produces colon tumors in rodents exhibiting pathological features that are similar to sporadic forms in human colon cancer.9) The AOM-induced colon cancer model in rat has been used to evaluate the potency of chemopreventive agents against colon cancer. 10)Aberrant crypt foci (ACF) were first identified in methylene blue stained, whole-mount preparations of colonic mucosa from carcinogen-treated rodents, 11) and ACF have also been found in the colons of patients both with or without colorectal cancer.12,13) McLellan et al. reported that ACF may be a significant biological lesion in the development of colon tumors, and aberrant crypt (AC) formation is specific for exposure to colon carcinogens. 14) From these findings, the colonspecific, carcinogen-induced ACF model in rodents has been used as a short term screening to identify chemopreventive agents for colon cancer. 15,16) In the present studies, the effect of isoliquiritigenin on the AOM-induced ACF formation model in mice was studied. Based on the data obtained, AOM-induced murine colon carcinogenesis experiment was also studied. MATERIALS AND METHODSChemicals AOM was purchased from Sigma Chemical Co., Ltd. (St. Louis, MO, U.S.A.). Isoliquiritigenin (ILG) was synthesized by the methods of Hulle et al. 17) and purified by column chromatography (silica gel with a mixture of nhexane and ethyl acetate). After recrystallization, the purity was quantificated by HPLC (octadecyl silica (ODS) with a gradient of acetonitrile and water) as over 99.8%. The yield of this material was 38.6%.Animals Five-weeks old ddY male mice were obtained from Shizuoka Laboratory Animal Center (Hamamatsu, Shizuoka, Japan). Effect of Isoliquiritigenin on Murine Colon Aberrant Crypt FociFive-weeks old ddY mice were housed in temperature-and humidity-controlled animal quarters with a 12 h light/dark cycle and fed CE-2 diet. (CLEA Japan Co., Ltd.) On the 1st and 8th days, AOM (10 mg/kg b.w.) was...

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Effects of chalcone derivatives on lipoxygenase and cyclooxygenase activities of mouse epidermis

Cited by 33 publications

References 20 publications

Lipoxin A4 modulates transmigration of human neutrophils across intestinal epithelial monolayers.

Lipoxin A4 modulates transmigration of human neutrophils across intestinal epithelial monolayers.

Anti-inflammatory Plant Flavonoids and Cellular Action Mechanisms

Studies on Cancer Chemoprevention by Traditional Folk Medicines XXV. Inhibitory Effect of Isoliquiritigenin on Azoxymethane-Induced Murine Colon Aberrant Crypt Focus Formation and Carcinogenesis.

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