Synthesis of Higher Oxidized Metabolites of Dibenz[<i>a</i>,<i>j</i>]anthracene Implicated in the Mechanism of Carcinogenesis

Zhang, Jintao; Dai, Wei; Harvey, Ronald G.

doi:10.1021/jo980416j

Cited by 27 publications

(16 citation statements)

References 14 publications

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“…Pterostilbene, but not resveratrol, inhibited mycelial growth of fungi involved in esca of grapevine (27). Resveratrol has shown activity against some human pathogenic bacteria (20,(28)(29)(30) and fungi (31), as well as the protozoan parasite Leishmania major (32). While 15 and 16 reportedly show activity against various types of microorganisms, these compounds were not active against O. perornata.…”

Section: Resultsmentioning

confidence: 98%

“…To a solution of phosphonium salt 20 (300 mg, 0.6 mmol), 4-fluorobenzaldehyde 22 (133 mg, 1.07 mmol), and catalytic amounts of 18 crown-6 was added 1.5 mL of a 50% sodium hydroxide (NaOH) in aqueous solution (20). The reaction was stirred at room temperature for 12 h. The reaction was poured into water and extracted with ethyl acetate (3 × 10 mL).…”

Section: E)-2-[4-(35-dimethoxystyryl)phenoxy]-6-(hydroxymethyl)tetramentioning

confidence: 99%

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Algicidal Activity of Stilbene Analogues

Mizuno

Schrader

Rimando

2008

J. Agric. Food Chem.

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Continuing our search for natural product and natural product-based compounds for the control of off-flavor in catfish, 29 stilbene analogues were synthesized and evaluated for algicidal activity against the 2-methylisoborneol (MIB)-producing cyanobacterium Oscillatoria perornata. The cis and trans isomers of 4-(3,5-dimethoxystyryl)aniline showed moderate and selective algicidal activity toward O. perornata with the lowest observed inhibitory concentration and lowest complete inhibition concentrations of 10 muM. This is the first report on selective stilbene algicidal activity toward a MIB-producing cyanobacteria species.

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Section: Resultsmentioning

confidence: 98%

Section: E)-2-[4-(35-dimethoxystyryl)phenoxy]-6-(hydroxymethyl)tetramentioning

confidence: 99%

Algicidal Activity of Stilbene Analogues

Mizuno

Schrader

Rimando

2008

J. Agric. Food Chem.

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“…At present, the production of skin-whitening cosmetics with oxyresveratrol as its basis depends on Mori cortex extract, because the quantity of the ingredient is limited and an effective method of synthesis has yet to be established. 24,25) Therefore, a search for alternative materials continues, as with polyphenolic compounds, which have high bioactivity and easy accessibility. Through our continuous effort, we have found several potent tyrosinase inhibitors from natural materials 26,27) that have an even greater potency than the well-known kojic acid.…”

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confidence: 99%

4-(6-Hydroxy-2-naphthyl)-1,3-bezendiol: A Potent, New Tyrosinase Inhibitor

Chung

Song

et al. 2007

Biological & Pharmaceutical Bulletin

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Melanin is secreted by melanocytes localized in the basal layer of the dermis 1) and is the major cellular component responsible for skin color. Although normal melanin pigmentation in the skin is the major defense mechanism against ultraviolet light, the production of abnormal pigmentation such as melasma, freckles, senile lentigines, and other forms of melanin hyperpigmentation can be a serious problem aesthetically.2)The novo synthesis of melanin involves the conversion of the amino acid, L-tyrosine to L-DOPA (3,4-dihydroxyphenylalanine), and then the oxidation of L-DOPA by tyrosinase, a rate-limiting enzyme, catalyzing step in melanin biosynthesis 3) that yields dopaquinone. This altered tyrosinase process often causes abnormal accumulation of melanin pigments.3) Therefore, it has been common practice to include tyrosinase inhibitors such as kojic acid 4) in the depigmentation ingredients of cosmetic products. 5)Various tyrosinase inhibitors that have been reported include hydroquinone, 6) ascorbic acid derivatives, 7) azelaic acid, 8) corticosteroids, 9) retinoids 10) and arbutin. 11) Recently, phenolic compounds were shown to have a tyrosinase inhibitory effect, in addition to their known anti-oxidative and free radical-scavenging efficacies.12) These compounds also are shown to exhibit anti-inflammatory, 13) antiviral, 14) and anti-allergic activities in various biological systems.15) Some stilbenes have polyphenolic compounds that are reported to possess various biological activities that are anti-carcinogenic, 16) anti-inflammatory, 17) and inhibit tyrosinase. 18-22)Resveratrol, a hydroxystilbene present at high concentrations in grape seeds and red wine, was recently shown to have a wide range of biological and pharmacological activities including as a potent antioxidant. Oxyresveratrol, one of the ingredients of the Mori cortex, 23) is reported to exert a potent inhibitory effect on tyrosinase's DOPA oxidase activity. At present, the production of skin-whitening cosmetics with oxyresveratrol as its basis depends on Mori cortex extract, because the quantity of the ingredient is limited and an effective method of synthesis has yet to be established. 24,25) Therefore, a search for alternative materials continues, as with polyphenolic compounds, which have high bioactivity and easy accessibility. Through our continuous effort, we have found several potent tyrosinase inhibitors from natural materials 26,27) that have an even greater potency than the well-known kojic acid.28) Recently, we succeeded in the synthesis of a new compound (patent application number: 10-2006-0071433), "HNB", as a polyphenolic compound (Fig. 1).The aim of this current study was to characterize the inhibition mode of HNB on mushroom-derived tyrosinase. We also investigated the inhibitory effects of HNB on melanin biosynthesis, cell viability, and its depigmenting effect on the murine B16F10 melanoma cell line (B16 cells). Tyrosinase is a key enzyme for melanin biosynthesis and known to be sensitive to ultraviolet light in the prese...

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“…1) MBMPA is synthesized via a single step process. However, resveratrol needs to pass many synthetic steps 25) and only very small quantities of resveratrol are found in natural resources. Therefore, MBMPA can be more easily obtained than resveratrol.…”

Section: Discussionmentioning

confidence: 99%

Protective Effect of (4-Methoxybenzylidene)-(3-methoxynophenyl)amine against Neuronal Cell Death Induced by Oxygen and Glucose Deprivation in Rat Organotypic Hippocampal Slice Culture

Choi

Kim

Son

et al. 2007

Biological & Pharmaceutical Bulletin

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Resveratrol (trans-3,4',5-trihydroxystilbene) is a natural phytoalexin found in grape skin, and has been suggested to be an antioxidant agent, an anticancer agent and a cardioprotective agent. In particular, recent experimental evidence has demonstrated that resveratrol exhibits neuroprotective effects in various assay systems. During the study on the resveratrol derivatives, we found that (4-methoxybenzylidene)-(3-methoxyphenyl)amine (MBMPA), which has blocked free phenolic groups, strongly protects neuronal cells against ischemic damage on a higher activity than resveratrol. The MBMPA potently reduced the level of neuronal cell death in an oxygen and glucose deprivation-exposed rat organotypic hippocampal slice culture. In addition, ATP depletion following the onset of oxygen and glucose deprivation in an adult hippocampal slice was blocked by the MBMPA treatment. These results suggest that MBMPA has a neuroprotective effect on an in vitro ischemia model, and may be useful for treating stroke.

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Synthesis of Higher Oxidized Metabolites of Dibenz[a,j]anthracene Implicated in the Mechanism of Carcinogenesis

Cited by 27 publications

References 14 publications

Algicidal Activity of Stilbene Analogues

Algicidal Activity of Stilbene Analogues

4-(6-Hydroxy-2-naphthyl)-1,3-bezendiol: A Potent, New Tyrosinase Inhibitor

Protective Effect of (4-Methoxybenzylidene)-(3-methoxynophenyl)amine against Neuronal Cell Death Induced by Oxygen and Glucose Deprivation in Rat Organotypic Hippocampal Slice Culture

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