Stilbenoid
Stilbenoids are hydroxylated derivatives of stilbene. They have a C6–C2–C6 structure. In biochemical terms, they belong to the family of phenylpropanoids and share most of their biosynthesis pathway with Chalconoid, chalcones. Most stilbenoids are produced by plants, and the only known exception is the antimicrobial stilbenoid drug tapinarof which is biosynthesized by the Gram-negative bacterium ''Photorhabdus luminescens.'' Chemistry Stilbenoids are hydroxylated derivatives of stilbene and have a C6–C2–C6 structure. They belong to the family of phenylpropanoids and share most of their biosynthesis pathway with Chalconoid, chalcones. Under UV irradiation, stilbene and its derivatives undergo intramolecular cyclization, called stilbene photocyclization to form dihydrophenanthrenes. Oligomeric forms are known as oligostilbenoids. Types ;Aglycones * Piceatannol in the roots of Norway spruces * Pinosylvin is a fungal toxin protecting wood from fungal infection, found in t ... [...More Info...]       [...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]   |
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Oligostilbenoid
Oligostilbenoids (oligo- or polystilbenes) are oligomeric forms of stilbenoids. Some molecules are large enough to be considered polyphenols and constitute a class of tannin Tannins (or tannoids) are a class of astringent, polyphenolic biomolecules that bind to and Precipitation (chemistry), precipitate proteins and various other organic compounds including amino acids and alkaloids. The term ''tannin'' is widel ...s. Examples Dimers * Ampelopsin A * Epsilon-viniferin * Pallidol * Quadrangularin A Trimers * α-Viniferin * Ampelopsin E * ''trans''-Diptoindonesin B * Gnetin H Tetramers * cajyphenol A * cajyphenol B * Flexuosol A * Hemsleyanol D * Hopeaphenol * Vaticanol B * R2-Viniferin (syn. Vitisin A) Modified * Diptoindonesin C can be isolated from the bark of '' Shorea pinanga'' Other * Diptoindonesin F can be isolated from the bark of '' Shorea gibbosa'' Glycosides * Diptoindonesin A References External links * {{oligostilbenoid ... [...More Info...]       [...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]   |
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Resveratrol
Resveratrol (3,5,4′-trihydroxy-''trans''-stilbene) is a stilbenoid, a type of natural phenol or polyphenol and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacterium, bacteria or fungus, fungi. Sources of resveratrol in food include the skin of grapes, blueberries, raspberries, mulberries, and peanuts. Although commonly used as a dietary supplement and studied in laboratory models of human diseases, there is no evidence-based medicine, high-quality evidence that resveratrol improves longevity, lifespan or has a substantial effect on any human disease. Research Resveratrol has been studied for its potential therapeutic use, with little evidence of anti-disease effects or health benefits in humans. Cardiovascular disease There is no evidence of benefit from resveratrol in people who already have heart disease. A 2018 meta-analysis found no effect on systolic blood pressure, systolic or diastolic blood pr ... [...More Info...]       [...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]   |
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Pterostilbene
Pterostilbene () (trans-3,5-dimethoxy-4-hydroxystilbene) is a stilbenoid chemically related to resveratrol. In plants, it serves a defensive phytoalexin role. Natural occurrence Pterostilbene is found in almonds, various ''Vaccinium'' berries (including Blueberry, blueberries), grape leaves and vines. It is also encountered in the xylem, particularly in the heartwood of ''Pterocarpus marsupium'' as well as in other species of the ''Pterocarpus'' family, including Malay padauk, the Narra tree (''Pterocarpus indicus''), Muninga and African padauk (''Pterocarpus erinaceus''), thus contributing to the high natural durability as a known phytoalexin. Safety and regulation Pterostilbene is considered to be a corrosive substance, is dangerous upon exposure to the eyes, and is an environmental toxin, especially to aquatic life. A preliminary study of healthy human subjects given pterostilbene for 6–8 weeks, showed pterostilbene to be safe for human use at dosages up to 250 mg p ... [...More Info...]       [...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]   |
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3,5-Dihydroxy-4-isopropyl-trans-stilbene
Tapinarof, also known as benvitimod and sold under the brand name Vtama among others, is a medication used for the treatment of plaque psoriasis. The medication is applied to the skin. Besides its use in medicine, tapinarof is a naturally occurring compound found in bacterial symbionts of nematodes which has antibiotic properties. The medication acts as an aryl hydrocarbon receptor agonist. Tapinarof was approved for medical use in the United States in May 2022. The US Food and Drug Administration (FDA) considers it to be a first-in-class medication. Medical uses Tapinarof is indicated for the treatment of plaque psoriasis in adults. Side effects In case of short term use the most common adverse effects are folliculitis, contact dermatitis, headache, pruritus (itching), and upper respiratory tract infection. Pharmacology Mechanism of action Tapinarof binds directly to topical aryl hydrocarbon receptor (AhR), suppressing inflammatory cytokines, modulating skin bar ... [...More Info...]       [...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]   |
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Ampelopsin B
Ampelopsin B is a stilbenoid dimer found in ''Ampelopsis glandulosa ''Ampelopsis glandulosa'', with common names creeper, porcelain berry, Amur peppervine, and wild grape, is an ornamental plant, native to temperate areas of Asia including China, Japan, India, Nepal, Myanmar, Vietnam, and the Philippines. It is g ...'' var. ''hancei'' (formerly ''Ampelopsis brevipedunculata'' var. ''hancei'').Chemical determination of the absolute structures of resveratrol dimers, ampelopsins A, B, D and F. Yoshiaki Takaya, Ke-Xu Yan, Kenji Terashima, Junko Ito and Masatake Niwa, Tetrahedron, 2002, 58, pages 7259–7265, References Stilbenoid dimers Ampelopsis {{aromatic-stub ... [...More Info...]       [...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]   |
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Tapinarof
Tapinarof, also known as benvitimod and sold under the brand name Vtama among others, is a medication used for the treatment of plaque psoriasis. The medication is applied to the skin. Besides its use in medicine, tapinarof is a naturally occurring compound found in bacterial symbionts of nematodes which has antibiotic properties. The medication acts as an aryl hydrocarbon receptor agonist. Tapinarof was approved for medical use in the United States in May 2022. The US Food and Drug Administration (FDA) considers it to be a first-in-class medication. Medical uses Tapinarof is indicated for the treatment of plaque psoriasis in adults. Side effects In case of short term use the most common adverse effects are folliculitis, contact dermatitis, headache, pruritus (itching), and upper respiratory tract infection. Pharmacology Mechanism of action Tapinarof binds directly to topical aryl hydrocarbon receptor (AhR), suppressing inflammatory cytokines, modulating skin bar ... [...More Info...]       [...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]   |
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Secondary Metabolite
Secondary metabolites, also called ''specialised metabolites'', ''secondary products'', or ''natural products'', are organic compounds produced by any lifeform, e.g. bacteria, archaea, fungi, animals, or plants, which are not directly involved in the normal cell growth, growth, Biological development, development, or reproduction of the organism. Instead, they generally mediate ecological biological interaction, interactions, which may produce a Natural selection, selective advantage for the organism by increasing its survivability or fecundity. Specific secondary metabolites are often restricted to a narrow set of species within a phylogenetic group. Secondary metabolites often play an important role in plant defense against herbivory and other interspecies defenses. Humans use secondary metabolites as medicines, flavourings, pigments, and recreational drugs. The term secondary metabolite was first coined by Albrecht Kossel, the 1910 Nobel Prize laureate for medicine and physio ... [...More Info...]       [...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]   |
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Ampelopsin A
Ampelopsin A is a resveratrol dimer found in ''Ampelopsis glandulosa ''Ampelopsis glandulosa'', with common names creeper, porcelain berry, Amur peppervine, and wild grape, is an ornamental plant, native to temperate areas of Asia including China, Japan, India, Nepal, Myanmar, Vietnam, and the Philippines. It is g ...'' var. ''hancei'' (formerly ''A. brevipedunculata'' var. ''hancei''). References External links (-)-Ampelopsin A, Metabolite Information Resveratrol oligomers Stilbenoid dimers Ampelopsis {{aromatic-stub ... [...More Info...]       [...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]   |
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Phytoalexins
Phytoalexins are antimicrobial substances, some of which are antioxidative as well. They are defined not by their having any particular chemical structure or character, but by the fact that they are defensively synthesized ''de novo'' by plants that produce the compounds rapidly at sites of pathogen infection. In general phytoalexins are broad spectrum inhibitors; they are chemically diverse, and different chemical classes of compounds are characteristic of particular plant taxa In biology, a taxon (back-formation from ''taxonomy''; : taxa) is a group of one or more populations of an organism or organisms seen by taxonomists to form a unit. Although neither is required, a taxon is usually known by a particular name and .... Phytoalexins tend to fall into several chemical classes, including terpenoids, glycomics, glycosteroids, and alkaloids; however, the term applies to any phytochemicals that are induced by microbial infection. Function Phytoalexins are produced in plants to ... [...More Info...]       [...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]   |
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Astringin
Astringin is a stilbenoid, the 3-β-D-glucoside of piceatannol. It can be found in the bark of ''Picea sitchensis'' and ''Picea abies'' (Norway spruce). It is also present in ''Vitis vinifera'' cells cultures and in wine Wine is an alcoholic drink made from Fermentation in winemaking, fermented fruit. Yeast in winemaking, Yeast consumes the sugar in the fruit and converts it to ethanol and carbon dioxide, releasing heat in the process. Wine is most often made f .... See also * Phenolic compounds in wine References Stilbenoid glycosides Phenol glucosides {{aromatic-stub ... [...More Info...]       [...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]   |
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Piceid
Piceid is a stilbenoid glucoside and is a major resveratrol derivative in grape juices. It can be found in the bark of the Sitka spruce (''Picea sitchensis''), hence its name. It can also be isolated from Japanese knotweed (''Reynoutria japonica''). Resveratrol can be produced from piceid by the mold ''Aspergillus oryzae'', the mold used to make sake and soy sauce Soy sauce (sometimes called soya sauce in British English) is a liquid condiment of China, Chinese origin, traditionally made from a fermentation (food), fermented paste of soybeans, roasted cereal, grain, brine, and ''Aspergillus oryzae'' or ''A ..., as the fungus produces a potent beta-glucosidase. ''trans''-Piceid is the glucoside formed with ''trans''-resveratrol, while ''cis''-piceid is formed with ''cis''-resveratrol. ''trans''-Resveratrol-3-''O''-glucuronide is one of the two metabolites of ''trans''-piceid in rat. Resveratrol glucoside from transgenic alfalfa prevents aberrant crypt foci in mice.R See a ... [...More Info...]       [...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]   |