Antiviral Activity of Some Hydroxycoumarin Derivatives

Galabov, Angel S.; Iosifova, Tanya; Vassileva, Elka; Kostova, I.

doi:10.1515/znc-1996-7-815

Cited by 18 publications

(8 citation statements)

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“…They are characterized by a variety of oxygenation pat terns on the benzopyrone nucleus (Murray, 1997) and display a remarkable array of biochemical and pharmacological actions (Bourinbaiar et al, 1993;Egan et al, 1990;Galabov et al, 1996;Maucher and von Angerer, 1994;Lee et al, 1994;Paya et al, 1994). We have recently reported on some biological activities of a series of simple coumarins including antimutagenic properties with respect to the mutagenic heterocyclic arom atic amine, 2-amino-3-methylimidazo[4,5-f]quinoline (Edenharder et al, 1995), and cytotoxic effects to human tum our cell lines .…”

Section: Introductionmentioning

confidence: 99%

Antibacterial Activity of Simple Coumarins: Structural Requirements for Biological Activity

Kayser

Kolodziej

1999

Zeitschrift Für Naturforschung C

128

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The antibacterial activity of a series of simple coumarins was evaluated against 8 microor ganisms, including three Gram-positive (Staphylococcus aureus, beta-hemolytic Streptococcus and Streptococcus pneum oniae) and five Gram-negative bacteria (Escherichia coli, Klebsiella pneum oniae, Pseudom onas aeruginosa, Proteus mirabilis and H aemophilus influenzae), using the microdilution broth method. The coumarins tested showed broad diversity regarding growth inhibitory activity with minimum inhibitory concentrations ranging from 0.9 to >12.4 (j.M . This study, presenting the first systematic analysis of structure-activity relationships among this group of coumarins, revealed some interesting structural requirements. While coumarins with a methoxy function at C-7 and, if present, an OH group at either the C-6 or C-8 position are invariably effective against the spectrum of tested standard bacteria (Gramnegative microorganisms including the Gram-positive bacterium Staphylococcus aureus), the presence of an aromatic dimethoxy arrangement is apparently favourable against those mi croorganisms which require special growth factors (beta-hemolytic Streptococcus, Streptococ cus pneum oniae and Haem ophilus influenzae). A combination of these structural features, two methoxy functions and at least one additional phenolic group as reflected by the highly oxygenated coumarins, identify promising candidates with antibacterial broad-spectrum ac tivity.

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Section: Introductionmentioning

confidence: 99%

Antibacterial Activity of Simple Coumarins: Structural Requirements for Biological Activity

Kayser

Kolodziej

1999

Zeitschrift Für Naturforschung C

128

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“…1) by a comparison of its spectral data with those of an authentic sample. Esculetin has already been reported to be contained in Euphorbia lathyris L., [14][15][16] Fraxinus japonica Blume and Cichorium intybus L. [17][18][19][20] Many scientiˆc papers have also reported the pharmacological properties of esculetin such as anti-in‰ammatory eŠects, 17,21) antioxidative, 22) antiviral, 23) antimutagenic 24) and antiproliferative activities, 25) ultraviolet absorption eŠect, 26) and inhibition of lipoxygenase activity. [27][28][29] However, there is no report on the eŠect of esculetin against tyrosinase activity.…”

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confidence: 99%

Mushroom Tyrosinase Inhibitory Activity of Esculetin Isolated from Seeds ofEuphorbia lathyrisL.

Masamoto

Ando

Murata

et al. 2003

Bioscience, Biotechnology, and Biochemistry

203

127

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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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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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Antiviral Activity of Some Hydroxycoumarin Derivatives

Cited by 18 publications

References 0 publications

Antibacterial Activity of Simple Coumarins: Structural Requirements for Biological Activity

Antibacterial Activity of Simple Coumarins: Structural Requirements for Biological Activity

Mushroom Tyrosinase Inhibitory Activity of Esculetin Isolated from Seeds ofEuphorbia lathyrisL.

Inhibitory Effects of Esculetin on Melanin Biosynthesis

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