Stilbene

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Classified as a diarylethene , it features a central ethylene moiety with one phenyl group substituent on each end of the carbon—carbon double bond. It has an E stereochemistry, meaning that the phenyl groups are located on opposite sides of the double bond, the opposite of its geometric isomer , cis -stilbene. Trans -stilbene occurs as a white crystalline solid at room temperature and is highly soluble in organic solvents. It can be converted to cis -stilbene photochemically , and further reacted to produce phenanthrene. Stilbene was discovered in by the French chemist Auguste Laurent.

Stilbene

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First, cAMP is able to induce Nrf2 expression in cells [ ].

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Federal government websites often end in. The site is secure. Box , Kuopio, Finland. Numerous studies have highlighted the key roles of oxidative stress and inflammation in aging-related diseases such as obesity, type 2 diabetes, age-related macular degeneration AMD , and Alzheimer's disease AD. In aging cells, the natural antioxidant capacity decreases and the overall efficiency of reparative systems against cell damage becomes impaired. There is convincing data that stilbene compounds, a diverse group of natural defence phenolics, abundant in grapes, berries, and conifer bark waste, may confer a protective effect against aging-related diseases. This review highlights recent data helping to clarify the molecular mechanisms involved in the stilbene-mediated protection against oxidative stress. The therapeutic potential of stilbene compounds against the most common aging-related diseases is discussed. Aging is one of the major risk factors for a wide range of chronic, metabolic, and neurodegenerative diseases.

Stilbene

Stilbenes are naturally occurring compounds with valuable properties such as antioxidant, anticancer, anti-diabetic, and anti-hypercholesterolemia activities. However, stilbene derivatives such as arylbenzofurans, bibenzyls, as well as stilbene oligomers also occur. Both aglycones and glycosylated forms can be found in plants, fruits, and vegetables. The most studied stilbene aglycone is resveratrol. It can be especially found in grapes Vitis vinifera L. Vitis species also contain rhapontigenin, piceatannol, pterostilbene from the stilbene aglycone class, viniferins and vitisins from stilbene oligomer class, astringin piceatannol 3- O -glucoside , and viniferin and vitisin glycosides from stilbene glycoside class. Other stilbenes found in food-related sources are gnetol, gnetifolin, and gnetofuran in Gnetum species, prenylated or geranylated stilbenes such as chiricanines from Lonchocarpus chiricanus or Arachis hypogaea , phyllodulcin natural sweetener , hydrangenol and thunberginol O -glucosides from some Hydrangea species, or mulberrosides oxyresveratrol glycosides from Morus alba. The presence of phenolic hydroxyl groups on the stilbene skeleton provides important antioxidant activity and further biological activities. Stilbene glycosides are less hydrophobic and more water soluble than the corresponding aglycones. Various interconversion methods using enzymatic synthesis exist.

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Nrf2 signaling is impaired in the aging RPE given an oxidative insult. Planta Medica. Combined effects of genistein, quercetin, and resveratrol in human and 3T3-L1 adipocytes. Molecular Endocrinology. In another recent work, a modification of the liposome with polyethylene glycol PEG was used to improve the bioavailability of rhaponticin RA and its plasma protein binding ability [ 45 ]. Nrf2-p62 couple seems to form a regulatory loop where Nrf2 is able to activate p62 expression and consequently Nrf2 nuclear localization is facilitated by p62 [ 96 , 97 ]. Activation of stress signaling pathways by electrophilic oxidized and nitrated lipids. It has long been known that anti-inflammatory agents may be one therapeutic means to reduce the risk of developing this disease. Keap1 -null mutation leads to postnatal lethality due to constitutive Nrf2 activation. Table 1. Cheng Q. Resveratrol analogs: promising chemopreventive agents. HSL is active against diglycerines while ATGL selectively act on the first step in the triglycerine hydrolysis resulting in the formation of diglycerines and free fatty acids [ ]. Melanosome-iron interactions within retinal pigment epithelium-derived cells.

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Kim J. For example, using tert -butyl hydroperoxide , oxidation of cis -stilbene produces 0. Molecular Endocrinology. Omar B. Activation of AMPK stimulates heme oxygenase-1 gene expression and human endothelial cell survival. Heterogeneity in red wine polyphenolic contents differentially influences Alzheimer's disease-type neuropathology and cognitive deterioration. In addition to the devastating general actions of ROS in cells, increased levels of oxidative stress may specifically disturb fundamental functions of the RPE such as POS phagocytosis [ ], visual cycle [ 93 ], and the integrity of the RPE barrier functions [ ]. Stilbene synthase STS is the key enzyme that catalyzes the biosynthesis of stilbenic compounds. Nrf2 induces interleukin-6 IL-6 expression via an antioxidant response element within the IL-6 promoter. The Journal of Biological Chemistry. Crabtree M. Chung J.