benzofurans and 3-3--4-5--tetrahydroxystilbene

Cardiovascular disease is a global health problem. According to the World Health Organization, ischemic heart disease was the leading cause of death globally in 2019, followed by stroke. The French paradox, which has been known since the early 1990s, describes the lower incidence of ischemic heart disease in French people despite the consumption of a diet rich in saturated fatty acids. This phenomenon has been attributed to the high intake of red wine, which is rich in polyphenols, namely, resveratrol and piceatannol. It is becoming clear that scirpusin B, a dimer of piceatannol, has anti-atherosclerotic properties such as vasodilation, antioxidant effects, and suppression of postprandial hyperglycemia; nonetheless, the effects of scirpusin B on the cardiovascular system have not been fully elucidated. This review aimed to describe the cardiovascular effects of piceatannol and scirpusin B on aortic and coronary artery dilation and cardiac function and to outline the cardiovascular effects of prostacyclin and nitric oxide, as these substances are involved in the vasodilatory effects exerted by these polyphenols.

Topics: Benzofurans; Cardiovascular System; Fruit; Humans; Passiflora; Polyphenols; Seeds; Stilbenes

Dietary stilbenes comprise a class of natural compounds that display significant biological activities of medicinal interest. Among them, their antioxidant, anti-aging and anti-angiogenesic properties are well established and subjects of numerous research endeavors. This mini-review aspires to account and present the literature reports published on research concerning various natural and synthetic stilbenes, such as trans-resveratrol. Special focus was given to most recent research findings, while the mechanisms underlying their anti-aging and anti-angiogenic effects as well as the respective signaling pathways involved were also presented and discussed.

Topics: Aging; Angiogenesis Inhibitors; Animals; Antineoplastic Agents, Phytogenic; Benzofurans; Dibenzocycloheptenes; Dietary Supplements; Humans; Plants; Resorcinols; Resveratrol; Rodentia; Stilbenes

The currently accepted paradigm is that fruits and vegetables should be consumed fresh and that their quality deteriorates during storage; however, there are indications that some metabolic properties can, in fact, be improved. We examined the effects of low temperature and high-CO

Topics: Acetates; Anaerobiosis; Benzofurans; Carbon Dioxide; Cold Temperature; Food Storage; Metabolomics; Pyruvic Acid; Signal Transduction; Stilbenes; Transcription Factors; Transcriptome; Up-Regulation; Vitis

Resveratrol and related oligostilbenes are defense molecules produced by grapevine in response to stresses including various elicitors or signal molecules. Together with their prominent role in planta, these compounds have been the center of much attention in recent decades due to their pharmacological properties. The cost-effective production of resveratrol derivatives such as viniferins or more structurally complex stilbene oligomers remains a challenging task. In this study, the chemical diversity of stilbenes produced by Vitis vinifera Pinot Noir hairy roots was investigated after elicitation for 4 days with a mixture of methyl jasmonate (100 μM) and cyclodextrins (50 mM). Two crude extracts obtained from the culture medium and from the hairy roots were fractionated by centrifugal partition chromatography. The fractions were chemically investigated by two complementary identification approaches involving a

Topics: Benzofurans; Chromatography, Liquid; Cyclopentanes; Flavanones; Flavonoids; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Oxylipins; Phenols; Plant Roots; Polycyclic Compounds; Resveratrol; Stilbenes; Vitis

The use of naturally occurring botanicals with substantial antioxidant activity to prevent photoageing is receiving increasing attention. We have previously identified piceatannol and scirpusin B, which is a dimer of piceatannol, as strong antioxidants that are present in passion fruit (Passiflora edulis) seeds. In the present study, the effects of passion fruit seed extract, piceatannol, and scirpusin B on human keratinocytes were investigated. The passion fruit seed extract and piceatannol upregulated the glutathione (GSH) levels in keratinocytes in a dose-dependent manner, indicating that piceatannol is an active component of the passion fruit seed extract in keratinocytes. The pretreatment with piceatannol also suppressed the UVB-induced generation of reactive oxygen species (ROS) in the keratinocytes. In addition, the transfer of the medium from the UVB-irradiated keratinocytes to non-irradiated fibroblasts enhanced matrix-metalloproteinase (MMP)-1 activity, and this MMP-1 induction was reduced when the keratinocytes were pretreated with piceatannol. These results suggest that piceatannol attenuates the UVB-induced activity of MMP-1 along with a reduction of ROS generation in keratinocytes. Thus, piceatannol and passion fruit seed extract containing high amounts of piceatannol are potential anti-photoageing cosmetic ingredients.

Topics: Benzofurans; Cell Line; Cells; Glutathione; Humans; Keratinocytes; Matrix Metalloproteinase 1; Passiflora; Plant Extracts; Radiation-Protective Agents; Reactive Oxygen Species; Seeds; Skin Aging; Stilbenes; Ultraviolet Rays

Grapevine canes are rich in resveratrol and its complex derivatives. These compounds have many biological activities and are needed mainly for health purposes. Canes, which are often wasted, can be used to produce these high-value compounds at low cost. We studied sixteen Vitis vinifera L. cultivars among the most widely cultivated ones worldwide. Polyphenols were extracted from their canes and identified by liquid chromatography-nuclear magnetic resonance spectroscopy. We accurately determined the content of E-ε-viniferin, E-resveratrol, E-piceatannol, and vitisin B and, for the first time, that of hopeaphenol and miyabenol C. The canes did not contain these major stilbene compounds in similar proportions, and their abundance and order of abundance varied according to the cultivar. For instance, Pinot noir has very high levels of E-resveratrol and E-ε-viniferin; Gewurztraminer has very high levels of vitisin B, and Carignan and Riesling have very high levels of hopeaphenol. These findings suggest that the right cultivar should be used to obtain the highest yield of a polyphenol of interest.

Topics: Benzofurans; Chromatography, Liquid; Phenols; Plant Stems; Polyphenols; Resveratrol; Species Specificity; Stilbenes; Vitis

We present stilbenoid profiles of canes from 16 grapevines. Fifteen stilbenoids were obtained through isolation and structure identification using MS, NMR, and [α](D) or as commercial standards. An HPLC-UV method for the simultaneous quantification of nine of these stilbenoids was developed and applied to canes of Vitis amurensis, Vitis arizonica, Vitis berlandieri, Vitis betulifolia, Vitis cinerea, Vitis × champini, Vitis × doaniana, Vitis labrusca, Vitis candicans (syn. Vitis mustangensis), Vitis riparia, Vitis rupestris, Vitis vinifera, Muscadinia rotundifolia, and a V. vinifera × M. rotundifolia hybrid. In these species, E-ampelopsin E, E-amurensin B, E-piceid, E-piceatannol, E-resveratrol, E-resveratroloside, E-ε-viniferin, E-ω-viniferin, and E-vitisin B were quantified, when found in sufficient amounts. Total concentrations ranged from ~2.2 to 19.5 g/kg of dry weight. Additional stilbenoids, E-3,5,4'-trihydroxystilbene 2-C-glucoside, Z-ampelopsin E, Z-trans-miyabenol C, E-trans-miyabenol C, scirpusin A, and Z-vitisin B, were identified but not quantified. Our results indicate that canes, particularly those of non-vinifera species, have substantial quantities of valuable, health-promoting stilbenoids.

Topics: Benzofurans; Chromatography, High Pressure Liquid; Flavonoids; Glucosides; Magnetic Resonance Spectroscopy; Phenols; Resveratrol; Stilbenes; Vitis

From stem bark of Callistemon rigidus (Myrtaceae), piceatannol and scirpusin B were isolated as components that exhibit inhibitory effects on alpha-amylase activity in isolated mouse plasma. In particular, scirpusin B also inhibited alpha-amylase in mouse gastrointestinal tract. Thus, we expect the depressive effect on the elevation of postprandial blood glucose may be a new medicinal use of this compound as well as the plant itself.

Topics: Administration, Oral; alpha-Amylases; Animals; Benzofurans; Blood Glucose; Enzyme Inhibitors; Gastrointestinal Tract; Hypoglycemic Agents; Male; Mice; Mice, Inbred Strains; Molecular Structure; Myrtaceae; Plant Bark; Plant Extracts; Plant Stems; Stilbenes

We examined the structure-activity relationships of isocoumarins, phthalides and stilbenes isolated from Hydrangeae Dulcis Folium and related compounds for the inhibition of histamine release in rat peritoneal mast cells. The activities of isocoumarins such as thunberginols A and B were more potent than those of dihydroisocoumarins such as hydrangenol and thunberginol G. The double bond at the 3-position seemed to be essential to potentiate the activity. The hydroxyl groups at the 8-, 3'- and 4'-positions of isocoumarin were essential for the activity, while the hydroxyl group at the 6-position was scarcely needed. Since the activities of benzylidenephthalides such as thunberginol F were more potent than those of hydramacrophyllols A and B, the presence of a double bond at the 3-position was needed to increase the activity. Moreover, the hydroxyl group at the 8-position was essential for the activity. On the time course study, thunberginols A, B and F completely inhibited histamine release by pretreatment at 100 microM for 1 to 15 min, whereas DSCG inhibited histamine release only following 1-min pretreatment at 1000 microM. These results suggested that the mechanisms of the inhibitory effect of thunberginols are different from that of DSCG.

Topics: Animals; Antigen-Antibody Reactions; Benzofurans; Benzopyrans; Bibenzyls; Calcimycin; Coumarins; Histamine Release; Immunoglobulin E; Inhibitory Concentration 50; Ionophores; Isocoumarins; Male; Mast Cells; p-Methoxy-N-methylphenethylamine; Peritoneum; Phenols; Phthalic Acids; Plant Leaves; Plants, Medicinal; Rats; Rats, Wistar; Stilbenes; Structure-Activity Relationship