32507-66-7

Usage

Biochem/physiol Actions

Isorhapontigenin or 4-methoxyresveratrol is a stilbene derivative isolated from a number of plants including Chinese medical herbs Gnetum Cleistostachyum and Iris Domestica (Belamcanda chinensis, leopard lily), and wine grapes. Similarly to resveratrol, isorhapontigenin is a potent antioxidant that attenuates ROS generation. Also, Isorhapontigenin exhibits pro-apoptopic and anti-cancer activities through downregulation of XIAP (X-linked inhibitor of apoptosis protein).

InChI:InChI=1/C15H14O4/c1-19-15-8-10(4-5-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h2-9,16-18H,1H3/b3-2+

Upstream product

• 900515-78-8 C₂₁H₁₉IO₂ 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 58605-10-0 methyl 3,5-bis(benzyloxy)benzoate 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 10083-24-6 trans-piceatannol 
• 74-88-4 methyl iodide 
• 29680-76-0 3,5-diacetoxybenzyl-(triphenyl)phosphonium bromide 
• 121-33-5 vanillin 
• 29654-55-5 5-(hydroxymethyl)benzene-1,3-diol 
• 24131-31-5 3,5-dibenzyloxybenzyl alcohol 
• 20767-14-0 3,4',5-Triacetoxy-3'-methoxy-stilben-α-carbonsaeure 
• 32727-29-0 3-hydroxy-5-[(1E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]phenyl β-D-glucopyranoside 
• 250778-33-7 (E)-1-(3-methoxy-4-benzyloxyphenyl)-2-(3,5-dibenzyloxyphenyl)ethylene 

Downstream Products

• 83088-26-0 (E)-tetramethylpiceatannol 
• 865474-98-2 6-hydroxy-3-(3,5-dihydroxyphenyl)-2-(3-methoxy-4-hydroxyphenyl)-4-(E)-(3-methoxy-4-hydroxystyryl)-2,3-dihydrobenzofuran 
• 291535-65-4 rac-shegansu B 
• 913556-40-8 rac-lehmbachol D 
• 291535-65-4 5-[2-(3-methoxy-4-hydroxyphenyl)-3-(3,5-dihydroxyphenyl)-7-methoxy-2,3-dihydro-5-benzofuranyl]vinyl-1,3-benzenediol 
• 291535-65-4 cis-shegansu B 
• 139101-67-0 Tristin 

Relevant academic research and scientific papers

Method for synthesizing artificially all-trans-resveratrol and derivative thereof

The invention discloses a method for synthesizing artificially all-trans-resveratrol and a derivative thereof. In the method, the precursors of all-trans-resveratrol and the derivative thereof are prepared by means of constructing a conjugated fused ring, thus the all-trans-spatial structure of resveratrol and the derivative thereof is restricted completely, to prepare all-trans-resveratrol and the derivative thereof. The resulting product of the preparation method of 1,2-stilbene or the derivative thereof in the invention is of all-trans configuration, so as to meet the demand of biologically active substance chemicals. Compared to the previous processes, the method provided by the invention has the advantages of simple processes and mild conditions, thereby meeting the green chemistry concept.

A method for the synthesis of hydroxy [...] composition of the new method (by machine translation)

The present invention discloses a new method for the synthesis of hydroxy [...] compound. The claimed method is: in the organic solvent, under a certain temperature, ammonium formate/through the palladium catalytic removal of benzyl protecting group system, to obtain hydroxyl [...] compound. The method has the mild reaction conditions, the operation is simple, small reagent toxicity, safety, high yield, wide range of application, low cost, relatively suitable for mass production and the like. (by machine translation)

Alkyl derivative manufacturing method

PROBLEM TO BE SOLVED: To provide a new method for producing an alkyl derivative of a polyphenol. SOLUTION: The method for producing an alkyl derivative of a polyphenol includes a step of reacting an acetic acid salt and an alkylating agent with the polyphenol. COPYRIGHT: (C)2013,JPOandINPIT

Biomimetic synthesis of active isorhapontigenin dimers

Synthetic isorhapontigenin was treated with several kinds of inorganic reagents and peroxidase so as to prepare active stilbene dimers. Among them, silver acetate in methanol gave two new isorhapontigenin dimers 4 and 5, together with four known natural stilbene dimers 2, 3, 6, and 7. Their structures and relative configurations were determined on the basis of spectral analysis, and their possible formation mechanisms were discussed, respectively. Compounds 2, 6, and 7 were artificially synthesized for the first time. All the products were evaluated for anti-inflammatory activities.

Antioxidant constituents from rhubarb: Structural requirements of stilbenes for the activity and structures of two new anthraquinone glucosides

The methanolic extracts from five kinds of rhubarb were found to show scavenging activity for DPPH radical and ·O2-. Two new anthraquinone glucosides were isolated from the rhizome of Rheum undulatum L. together with two anthraquinone glucosides, a naphthalene glucoside, and 10 stilbenes. In the screening test for radical scavenging activity of rhubarb constituents, stilbenes and a naphthalene glucoside showed activity, but anthraquinones and sennosides did not. In addition, most stilbenes inhibited lipid peroxidation of erythrocyte membrane by tert-butyl hydroperoxide. Detailed examination of the scavenging effect on various related compounds suggested the following structural requirements; 1) phenolic hydroxyl groups are essential to show the activity; 2) galloyl moiety enhances the activity; 3) glucoside moiety reduces the activity; 4) dihydrostilbene derivatives maintain the scavenging activity for the DPPH radical, but they show weak activity for ·O2-. In addition, several stilbenes with both the 3-hydroxyl and 4′-methoxyl groups inhibited xanthine oxidase.

Inhibitors from rhubarb on lipopolysaccharide-induced nitric oxide production in macrophages: Structural requirements of stilbenes for the activity

By bioassay-guided separation, three stilbenes (rhapontigenin, piceatannol, and resveratrol), two stilbene glucoside gallates (rhaponticin 2″-O-gallate and rhaponticin 6″-O-gallate), and a naphthalene glucoside (torachrysone 8-O-β-D-glucopyranoside) with inhibitory activity against nitric oxide (NO) production in lipopolysaccharide-activated macrophages were isolated (IC50=11-69μM). The oxygen functions (-OH, -OCH3) of stilbenes at the benzene ring were essential for the activity. The glucoside moiety reduced the activity, while the α,β-double bond had no effect. Furthermore, the active stilbenes (rhapontigenin, piceatannol, and resveratrol) did not inhibit inducible NO synthase activity, but they inhibited nuclear factor-κB activation following expression of iNOS. Copyright