Phenolic Compounds with Anti-Inflammatory Activity from<i>Eupatorium buniifolium</i>

Muschietti, Liliana; Gorzalczany, Susana; Ferraro, Graciela; Acevedo, Cristina; Martino, Virginia

doi:10.1055/s-2001-18355

Cited by 48 publications

(28 citation statements)

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“…So far more than 1300 types of coumarin have been identified as natural or synthesized compounds. Coumarins have recently been reported to have interesting pharmacologic and biochemical properties such as antioxidative, 1,2) antiinflammatory, and antiallergic effects, 3,4) inhibition of platelet aggregation 5) and protein kinase, 6) induction of apoptosis, 7) and antiviral, 8) antidifferentiative, 9) and antimutagenic activity. 10) Melanin pigment is a heteropolymer of indole compounds synthesized within melanocytes in the epidermis.…”

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confidence: 99%

Inhibitory Effects of Esculetin on Melanin Biosynthesis

Masamoto

Murata

et al. 2004

Biological & Pharmaceutical Bulletin

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Coumarins are widely distributed in plants and are especially abundant in the bark, leaves, and roots of Umbelliferae and Rutaceae plants. So far more than 1300 types of coumarin have been identified as natural or synthesized compounds. Coumarins have recently been reported to have interesting pharmacologic and biochemical properties such as antioxidative, 1,2) antiinflammatory, and antiallergic effects, 3,4) inhibition of platelet aggregation 5) and protein kinase, 6) induction of apoptosis, 7) and antiviral, 8) antidifferentiative, 9) and antimutagenic activity. 10)Melanin pigment is a heteropolymer of indole compounds synthesized within melanocytes in the epidermis. Inhibitory compounds on melanogenesis are useful as skin-whitening agents used in cosmetics and as treatment of hyperpigmentation. Tyrosinase is known to play a critical regulatory role in melanin biosynthesis. 11) Therefore, many tyrosinase inhibitors that suppress melanogenesis in epidermal layers have been actively studied in cosmetics and pharmaceuticals. [12][13][14][15] These observations led us to search for naturally occurring tyrosinase inhibitors.Recently, we have isolated esculetin from the seeds of Euphorbia lathyris L. as a mushroom tyrosinase inhibitory compound.16) To the best of our knowledge, this is the first report of the tyrosinase-inhibitory effects of esculetin. In this study, 18 coumarins and four cinnamic acid derivatives were examined for antityrosinase activity and study of the structure-activity relationship. We evaluated further the inhibitory effect on melanin synthesis in B16 melanoma cells and guinea pig epidermal sheets of esculetin, which showed the strongest inhibitory activity among these compounds. MATERIALS AND METHODS MaterialsCoumarin, 4-hydroxycoumarin, umbelliferone, 7-methoxycoumarin, 6-hydroxy-4-methylcoumarin, 7-hydroxy-4-methylcoumarin, esculin, esculetin, scopoletin, 7-hydroxycoumarin-4-acetic acid, and 7-hydroxycoumarin-3-carboxylic acid were purchased from Aldrich Chemical Co. (Milwaukee, WI, U.S.A.). 4-Methylesculetin, 5,7-dihydroxy-4-methylcoumarin, isoscopoletin, and fraxetin were obtained from Extrasynthese Co. (Genay, France). Daphnetin, daphnin, and daphnetin-8-glucoside were isolated from Daphne odora. The chemicals purchased were used as received.Assay of Tyrosinase-Inhibitory Activity The assay was performed as previously described.16) One milliliter of a 1.5 mM L-3,4-dihydroxyphenylalanine (DOPA) solution, 0.1 ml of dimethyl sulfoxide (DMSO) with or without sample, and 1.8 ml of 1/15 M phosphoric acid buffer solution (pH 6.8) were mixed. The mixtures were preincubated at 25°C for 10 min. Then, 0.1 ml of the aqueous solution of mushroom tyrosinase (1000 U/ml, Sigma Chemical Co., St. Louis, MO, U.S.A.) was added, and the reaction was monitored at 475 nm. A control reaction was conducted with DMSO. The percentage of inhibition of tyrosinase activity was calculated as follows: inhibition (%)ϭ(AϪB)/Aϫ100, where A represents the difference in the absorbance of the control sample between the incub...

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Inhibitory Effects of Esculetin on Melanin Biosynthesis

Masamoto

Murata

et al. 2004

Biological & Pharmaceutical Bulletin

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“…Ursolic acid was also reported to suppress the expression of proinflammatory enzymes, cyclooxygenase-2 and inducible nitric oxide synthase (Suh et al, 1998), and to inhibit nuclear factor-κB activation (Shishodia et al, 2003). Scopoletin was found to inhibit 12-Otetradecanoylphorbol 13-acetate-induced mouse ear oedema (Muschietti et al, 2001), and to suppress the expression of inducible nitric oxide synthase from lipopolysaccharide-induced macrophages . These findings strongly suggest that ursolic acid and scopoletin may contribute, at least in part, to the antiinflammatory activity exerted by S. deltoides.…”

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confidence: 99%

Antiinﬂammatory activity of Synurus deltoides

Park

Son

Kim³

et al. 2004

Phytotherapy Research

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Synurus deltoides Aiton, Nakai, is an edible plant that has been used as a folk medicine for treating inflammatory disorders. This investigation was carried out to establish the antiinflammatory activity of this plant material using a 75% ethanol extract from the aerial part of S. deltoides. Against the acute inflammatory animal model of mouse croton oil-induced ear oedema assay, the extract did not show significant inhibition at 100-800 mg/kg by oral administration. On the other hand, the extract showed considerable inhibition against the chronic inflammatory animal model of rat adjuvant-induced arthritis (25% inhibition at 100 mg/kg/day) while prednisolone exerted 40% inhibition at 10 mg/kg/day. In addition, S. deltoides possessed strong analgesic activity (IC50 = 50 mg/kg) in the acetic acid-induced writhing test. From the extract, ursolic acid and scopoletin were successfully isolated and their contents were found to be 0.31% and 0.37% (w/w), respectively, based on the dried extract by HPLC analysis. All the results obtained indicate that this plant material may be used beneficially as an antiinflammatory agent having analgesic action.

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“…A variety of bioactivities have been ascribed to this compound, including antiinflammatory, antioxidation, antitumor, and anti-angiogenesis activities. These activities are potentially due to inhibition of nitric oxide synthesis, COX-2 expression, pro-inflammatory cytokine production, and endothelial cell migration and tube formation [Muschietti et al, 2001;Ng et al, 2003;Manuele et al, 2006;Ding et al, 2005;Pan et al, 2009]. Recently, we found that intraperitoneal injection of scopoletin effectively reduced the inflammation of joints and synovial thickening in AA rats.…”

Section: Introductionmentioning

confidence: 96%

Scopoletin induces apoptosis of fibroblast‐like synoviocytes from adjuvant arthritis rats by a mitochondrial‐dependent pathway

Liu¹,

Dai²,

Liu³

et al. 2009

Drug Development Research

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Scopoletin is a naturally occurring coumarin compound found in many medicinal plants, such as Erycibe obtusifolia Benth and Aster tataricus. Our previous studies have demonstrated that this compound could ameliorate adjuvant-induced arthritis in a rat model of human rheumatoid arthritis (RA). Since the proliferation of fibroblast-like synoviocytes (FLS) plays a pivotal role in the formation and growth of pannus, which leads to subsequent joint destruction in RA, we examined the effects of scopoletin on FLS apoptosis. Primary FLS from adjuvant arthritis rats were purified and cultured, and then treated with increasing concentrations of scopoletin (250, 500, 1,000 mM) for 24 h. Scopoletin decreased the viability of FLS in a dose-dependent manner and remarkably induced their apoptosis, as revealed by Hochest 33258 staining and flow cytometry analysis. Further experiments showed that scopoletin activated caspase-3, depolarized mitochondrial membrane potential, regulated expression of bcl-2 family members, and reduced the activation of NF-kB proteins. These results indicated that scopoletin induced apoptosis of FLS through a mitochondrial-dependent pathway, which may be mediated by inhibition of NF-kB activation and promotion of caspase-3 activation. Drug Dev Res 70 : 378-385, 2009. r

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Phenolic Compounds with Anti-Inflammatory Activity fromEupatorium buniifolium

Cited by 48 publications

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Inhibitory Effects of Esculetin on Melanin Biosynthesis

Inhibitory Effects of Esculetin on Melanin Biosynthesis

Antiinﬂammatory activity of Synurus deltoides

Scopoletin induces apoptosis of fibroblast‐like synoviocytes from adjuvant arthritis rats by a mitochondrial‐dependent pathway

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