Cis-Resveratrol is a polyhydroxy stilbene compound extracted from the plant Polygonum cuspidatum. In 1989, as the answer to the “French Paradox” – the cardiovascular protective effect of resveratrol contained in red wine was discovered, related research on resveratrol has attracted widespread attention. Studies have found that resveratrol has a very wide range of pharmacological and pharmacological activities and health care effects. Resveratrol has effects on the three stages of cancer initiation, promotion and development, and can inhibit and treat tissue canceration and tumor occurrence; the antioxidant and estrogen activity of Cis-Resveratrol is not only effective for cardiovascular diseases (such as: Hypertension, hyperlipidemia, atherosclerosis, etc.) have preventive and therapeutic effects, and also have a protective effect on the nervous system; Cis-Resveratrol is a phytoalexin produced when plants are attacked by pathogens and the environment deteriorates, and has antibacterial and anti-inflammatory effects
Cis-Resveratrol is a natural estrogen, which can significantly promote bone formation, prevent and treat osteoporosis; in addition, resveratrol also has the functions of protecting liver and gallbladder, resisting pathogenic microorganisms, and activating Sirtuins enzymes , prolong cell life, beautify and so on. At present, resveratrol has been widely used in medicine, health products, food, cosmetics and other fields, and its market demand is huge.
Preparation of Cis-Resveratrol
cis-resveratrol was prepared as follows:
(1) Synthesis of the compound of formula (V)
Take 0.47g (0.02mol) of sodium metal and add it to 10mL (0.17mol) of absolute ethanol. After the sodium metal is completely dissolved, mix 1.66g (0.01mol) of 3,5-dimethoxybenzaldehyde with 1.47g ( 0.01mol) of p-methoxyphenylacetonitrile was dissolved in 10mL (0.17mol) of ethanol and added to the reaction flask, refluxed at 75°C for 12 hours, cooled, a large amount of light yellow crystals were precipitated, and recrystallized with ethanol to obtain 2.1g of the compound of formula (V), The yield was 71%.
(2) Synthesis of the compound of formula (VI)
Weigh 2.95g (0.01mol) of the compound of formula (V) and dissolve it in 75mL (1.34mol) of ethylene glycol, add 75mL of 15% (0.3mol) sodium hydroxide solution, stir, react at 120°C for 72 hours, cool , acidified to acidity by adding dilute hydrochloric acid, extracted with ethyl acetate, dried and concentrated, and recrystallized from ethanol/water to obtain 2.12 g of light yellow needle crystals, namely the compound of formula (VI), with a yield of 67%.
(3) Synthesis of the mixture of formula (VII) compound and formula (VIII) compound
Weigh 3.14g (0.01mol) of the compound of formula (VI), 3.00g (0.047mol) of copper powder and 30g (0.23mol) of quinoline, stir, react at 220°C for 2 hours, cool to room temperature, and add an appropriate amount of ethyl acetate , washed with dilute hydrochloric acid to acidity, mass fraction 5% sodium hydroxide solution was washed to alkaline, the organic layer was dried, concentrated to obtain light yellow oily liquid 1.92g, i.e. the mixture of formula (VII) compound and formula (VIII) compound, yield 71%.
(4) separation of the mixture of formula (VII) compound and formula (VIII) compound
Add 3.0 g of the obtained mixture of the compound of formula (VII) and compound of formula (VIII) into 1 mL of ethyl acetate to dissolve, load the sample on a column filled with 100 g of silica gel, and wash with a mixed solvent of petroleum ether-chloroform at a volume ratio of 1:8. Elution was carried out by removing solvent, and compound a(VII) 1.2g (yield 60%) and compound b(VIII) 0.6g (yield 20%) were successively obtained.
(5) The compound of formula (II) is the synthesis of trans-resveratrol
Weigh 2.70g (0.01mol) compound of formula (VIII) into a 100mL three-neck round bottom flask, add 40mLCH2Cl2, stir for a while under ice-water bath, slowly add 8mL (0.08mol) BBr3 solution dropwise, after the dropwise addition Stir at room temperature for 13 hours, add a large amount of water, extract with ethyl acetate, dry, concentrate, and recrystallize to obtain 1.90 g of light yellow solid with a yield of 81.5%. The obtained product was analyzed and confirmed to be the compound of formula (II), ie trans-resveratrol.
(6) The compound of formula (I) is the synthesis of cis-resveratrol
Weigh 2.70g (0.01mol) of the compound of formula (VII) into a 100mL three-necked round-bottomed flask, add 40mL (0.63mol) CH2Cl2, stir for a while under ice-water bath, slowly add dropwise 8mL (0.08mol) BBr3 solution , after the dropwise addition, stirred at room temperature for 12 hours, added a large amount of water, extracted with ethyl acetate, dried, concentrated, and recrystallized to obtain 1.75 g of white crystals, with a yield of 76.8%. The obtained product was analyzed and confirmed to be the compound of formula (I), namely cis-resveratrol.
Anti-Inflammatory Effect of Cis-Resveratrol
Resveratrol is a normally taking place phenolic compound uncovered in red grapes along with gewurztraminer as cis as well as trans isomers. Current investigates have in fact shown that trans-resveratrol has anti-inflammatory, antioxidant, anticancer, antitumor, and also immunomodulatory houses. Nonetheless, it was unclear whether cis-resveratrol may show comparable job. The objective of this research study was to analyze the results of cis- as well as trans-resveratrol on the production of pro-inflammatory cytokines along with conciliators in human macrophages. We analyzed the opportunity that cis and likewise trans resveratrol might influence cytokine secretion by modulating the inflammasome, an intracellular multiprotein center whose assembly creates caspase-1 activation as well as likewise secretion of energised IL by macrophages -1 β. Our end results disclosed that pretreatment of macrophages with cis-resveratrol not simply decreased pro-IL-1β manufacturing as well as IL-1β secretion, nonetheless likewise inhibited ATP-induced transcription as well as likewise expression of caspase-1 in addition to caspase-4. activation. Substantially, cis-resveratrol stopped the expression of the purinergic receptor P2X( 7 )R as well as additionally the endoplasmic reticulum tension marker Glc controling healthy and balanced protein 78, yet similarly minimized responsive oxygen kinds production. Additionally, cis-resveratrol undermined cyclooxygenase 2 expression and prostaglandin E2 production. Cis-resveratrol furthermore decreased p38 MAPK phosphorylation in addition to c-Jun healthy protein expression. These outcomes suggest that cis-resveratrol produces anti-inflammatory effects by inhibiting typical along with irregular inflammasomes as well as likewise associated courses in human macrophages. Nonetheless also inhibits ATP-induced transcription as well as activation of caspase-1 as well as likewise caspase-4. Significantly, cis-resveratrol impeded the expression of the purinergic receptor P2X( 7 )R along with the endoplasmic reticulum stress pen Glc controling healthy and balanced protein 78, however also minimized responsive oxygen varieties production. In addition, cis-resveratrol undermined cyclooxygenase 2 expression as well as prostaglandin E2 manufacturing. Cis-resveratrol also lowered p38 MAPK phosphorylation and additionally c-Jun healthy and balanced protein expression. These results recommend that cis-resveratrol creates anti-inflammatory outcomes by stopping normal and likewise irregular inflammasomes and likewise relevant paths in human macrophages. However in addition hinders ATP-induced transcription and also activation of caspase-1 and also caspase-4. Especially, cis-resveratrol prevented the expression of the purinergic receptor P2X( 7 )R along with the endoplasmic reticulum stress and anxiety pen Glc regulative healthy and balanced protein 78, however furthermore lowered reactive oxygen selections making. In addition, cis-resveratrol weakened cyclooxygenase 2 expression as well as prostaglandin E2 manufacturing. Cis-resveratrol additionally decreased p38 MAPK phosphorylation and also c-Jun healthy and balanced protein expression. These outcomes advise that cis-resveratrol produces anti-inflammatory impacts by hindering usual and also irregular inflammasomes and additionally relevant courses in human macrophages. It in addition lessens the production of energetic oxygen. In addition to that, cis-resveratrol threatened cyclooxygenase 2 expression in addition to prostaglandin E2 production. Cis-resveratrol also lowered p38 MAPK phosphorylation as well as c-Jun protein expression. These results suggest that cis-resveratrol generates anti-inflammatory effects by preventing normal as well as irregular inflammasomes and also related courses in human macrophages. It also decreases the production of energetic oxygen. In addition, cis-resveratrol attenuated cyclooxygenase 2 expression and also prostaglandin E2 manufacturing. Cis-resveratrol also decreased p38 MAPK phosphorylation as well as c-Jun healthy protein expression. These outcomes recommend that cis-resveratrol produces anti-inflammatory results by inhibiting normal along with atypical inflammasomes and additionally relevant paths in human macrophages.
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ZhiShang Chemical is owned by ZhiShang Group is a professional new-type chemicals enterprise combined into research and development, production and sales .
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