pinosylvin and pterostilbene

Stilbenes are small molecular weight (approximately 200-300 g/mol), naturally occurring compounds and are found in a wide range of plant sources, aromatherapy products, and dietary supplements. These molecules are synthesized via the phenylpropanoid pathway and share some structural similarities to estrogen. Upon environmental threat, the plant host activates the phenylpropanoid pathway and stilbene structures are produced and subsequently secreted. Stilbenes act as natural protective agents to defend the plant against viral and microbial attack, excessive ultraviolet exposure, and disease. One stilbene, resveratrol, has been extensively studied and has been shown to possess potent anti-cancer, antiinflammatory and anti-oxidant activities. Found primarily in the skins of grapes, resveratrol is synthesized by Vitis vinifera grapevines in response to fungal infection or other environmental stressors. Considerable research showing resveratrol to be an attractive candidate in combating a wide variety of cancers and diseases has fueled interest in determining the disease-fighting capabilities of other structurally similar stilbene compounds. The purpose of this review is to describe four such structurally similar stilbene compounds, piceatannol, pinosylvin, rhapontigenin, and pterostilbene and detail some current pharmaceutical research and highlight their potential clinical applications.

Topics: Humans; Resveratrol; Stilbenes

Resveratrol and its methyl ethers, which belong to a class of natural polyphenol stilbenes, play important roles as biologically active compounds in plant defense as well as in human health. Although the biosynthetic pathway of resveratrol has been fully elucidated, the characterization of resveratrol-specific O-methyltransferases remains elusive. In this study, we used RNA-seq analysis to identify a putative aromatic O-methyltransferase gene, AcOMT1, in Acorus calamus. Recombinant AcOMT1 expressed in Escherichia coli showed high 4'-O-methylation activity toward resveratrol and its derivative, isorhapontigenin. We purified a reaction product enzymatically formed from resveratrol by AcOMT1 and confirmed it as 4'-O-methylresveratrol (deoxyrhapontigenin). Resveratrol and isorhapontigenin were the most preferred substrates with apparent K

Topics: Acorus; Cloning, Molecular; Kinetics; Methylation; Methyltransferases; Plant Proteins; Resveratrol; Stilbenes

Aiming at the development of an active food packaging, the goal of this study was to increase stilbenes (resveratrol (RV), pterostilbene (PT) and pinosylvin (PS)) aqueous solubility and stability using hydropropyl-cyclodextrins (HP-CDs) and bile salts. To evaluate stilbene concentration, an HPLC-DAD method was validated. Stilbene solubility was improved by the formation of inclusion complexes and micellar systems with higher solubility values obtained for the inclusion complexes with cyclodextrins. Inclusion complexes revealed a 1:1 stoichiometry for RV and PT and a 1:2 for PS. Solid state characterisation was carried out using X-ray diffraction, Fourier transform infrared spectroscopy and differential scanning calorimetry. (1)H NMR studies were also performed to characterise the prepared complexes. Photostability studies revealed that CDs were able to increase stilbene photostability at 4 °C. This work showed that stable stilbene solutions can be achieved using hydroxypropyl-CDs, contributing for their incorporation in several materials for the food and pharmaceutical industries.

Topics: Antioxidants; Bile Acids and Salts; Calorimetry, Differential Scanning; Chromatography, High Pressure Liquid; Cyclodextrins; Magnetic Resonance Spectroscopy; Resveratrol; Solubility; Solutions; Spectroscopy, Fourier Transform Infrared; Stilbenes; X-Ray Diffraction

The aim of this study was to evaluate the effects of pinosylvin (PIN) and pterostilbene (PTE), natural substances from the stilbenoid group, on the development of adjuvant arthritis in rats.. Adjuvant arthritis (AA) was induced by a single intradermal injection of Mycobacterium butyricum in incomplete Freund's adjuvant in male Lewis rats. Our experiments included healthy intact animals as reference controls, arthritic animals without any drug administration, and arthritic animals with administration of PIN and PTE in the oral daily dose of 30 mg/kg b.w. The treatment involved administration of the substances tested from day 0, i.e. the day of immunization, to the experimental day 28. The following parameters were monitored: change of the hind paw volume (HPV) on day 14, 21 and 28, luminol-enhanced chemiluminescence (CL) of the joint and myeloperoxidase (MPO) activity in hind paw joint homogenates (day 28).. Arthritic animals treated with PIN showed a decrease in HPV, significantly on days 14 and 28. PIN decreased CL of the joint as well as MPO activity of the joint homogenate, in comparison with untreated animals. PTE had no effect on HPV and MPO activity in hind paw joint homogenates and exerted only a partial effect on luminol-enhanced CL.. On the basis of our results we conclude that the effect of PTE on CL was only partial. PIN, on the other hand, had a beneficial anti-inflammatory and antioxidant effect on oxidative stress induced biochemical changes occurring in AA, as determined by all three functional parameters.

Topics: Animals; Anti-Inflammatory Agents; Antioxidants; Arthritis, Experimental; Disease Models, Animal; Dose-Response Relationship, Drug; Drug Therapy, Combination; Male; Oxidative Stress; Peroxidase; Rats; Rats, Inbred Lew; Reactive Oxygen Species; Stilbenes

Oxidative stress is related to a number of autoimmune diseases, e.g. rheumatoid arthritis, cancer, etc. The main source of pathologically working reactive oxygen species (ROS) are activated polymorphonuclear leukocytes (PMNL).. There are some papers comparing structure - pharmacological efficiency relationship of vegetal substances from the stilbenoid group. We compared the effect of trans-resveratrol, which is well-known by its antioxidative activity, with the effect of pinosylvin and pterostilbene.. Luminol-enhanced chemiluminescence (CL) was used to study the antioxidative action. The effect was observed in whole blood and in isolated PMNL. The concentrations of substances tested were 0.01-100 microM. Due to the different abilities of luminol and isoluminol to pass through the cell membrane, we studied the effect of the substances tested on intracellular and extracellular ROS. To stimulate the production of ROS we used phorbol-myristate-acetate (PMA), which activates PMNL via protein kinase C.. Resveratrol, pinosylvin and pterostilbene inhibited significantly the CL of whole blood and extra- and intracellular CL of isolated PMNL in a dosedependent manner. Depending on different functional groups of the stilbene molecule, resveratrol inhibited CL of whole blood and isolated PMNL, whereas pinosylvin influenced mainly intracellular CL and pterostilbene extracellular CL.. The presence of different functional groups in the molecules of stilbenoids influence their antioxidative effect. Modification of these functional groups may result in derivatives with required antioxidative properties, targeting mainly extracellular ROS which are responsible for tissue damage during chronic inflammation.

Topics: Adenosine Triphosphate; Antioxidants; Cell Survival; Dose-Response Relationship, Drug; Humans; Luminescence; Neutrophils; Reactive Oxygen Species; Resveratrol; Stilbenes; Structure-Activity Relationship

A method of analysis of pterostilbene [trans-3,5-dimethoxy-4'-hydroxystilbene] is necessary to study the kinetics of in vitro and in vivo metabolism and determine its concentration in foodstuffs. A novel and simple high-performance liquid chromatographic method was developed for determination of pterostilbene in rat serum. Serum proteins (0.1 mL) are precipitated with cold acetonitrile after addition of the internal standard, pinosylvin. Separation was achieved on a Phenomenex C18 column (250 mm x 4.60 mm) with fluorescence excitation at 330 nm and emission at 374 nm. The calibration curves were linear ranging from 0.5 to 100 microg/mL. The mean extraction efficiency was >99%. Precision of the assay was <15% (CV), and was within 14% at the limit of quantitation (0.5 microg/mL). Bias of the assay was lower than 14%, and was within 9% at the limit of quantitation. The assay was applied successfully to the study of pterostilbene pharmacokinetics in rats.

Topics: Animals; Calibration; Chromatography, High Pressure Liquid; Data Interpretation, Statistical; Indicators and Reagents; Male; Rats; Rats, Sprague-Dawley; Reference Standards; Reproducibility of Results; Solutions; Spectrometry, Fluorescence; Stilbenes