22255-22-7Relevant articles and documents
Complete assignment of the1H and13C NMR spectra of resveratrol derivatives
Koh, Dongsoo,Park, Kwan Ha,Jung, Jihyun,Yang, Heejung,Hun Mok,Lim, Yoongho
, p. 768 - 770 (2001)
Contract/grant sponsor: Korea Ministry of Marine Affairs and Fishery The complete 1H and 13C chemical shift assignments of six derivatives of resveratrol [(E)-5-[2-(4-hydroxyphenyl)ethenyl]-1,3-benzenediol] that possess leukotriene D
η6-arene-tricarbonylchromium complexes in the syntheses of trans-resveratrol and pinostilbene
Polunin, Konstantin E.,Polunina, Irina A.,Schmalz, Hans-Guenther
, p. 178 - 179 (2002)
New syntheses of trans-resveratrol (trans-3,5,4′-trihydroxystilbene) and pinostilbene (trans-3,4′-dihydroxy-5-methoxystilbene) via nucleophilic demethylation of trimethoxystilbene were performed, whereby trans-3,5,4′-trimethoxystilbene was obtained through facilitated benzylic deprotonation of an η6-benzene-Cr(CO)3 derivative and subsequent coupling with para-anisaldehyde in an aldol-type or Wittig-Horner reaction.
Heterogeneous heck coupling in multivariate metal-organic frameworks for enhanced selectivity
Brown, Jonathan W.,Jarenwattananon, Nanette N.,Otto, Trenton,Wang, James L.,Gl?ggler, Stefan,Bouchard, Louis-S.
, p. 105 - 107 (2015)
Abstract Highly selective heterogeneous Heck coupling has been demonstrated inside a series of metal-organic frameworks (MOFs). These MOFs, Zn4O(BDC-NH2)n(BDC)(3 - n) (n = 3, 2.4, 1.8, 1.2, 0.9, 0.75, 0.6, 0.3,
Anti-allergic action of resveratrol and related hydroxystilbenes
Cheong, Ho,Ryu, Shi-Yong,Kim, Kyeong-Man
, p. 266 - 268 (1999)
Resveratrol (1) and nine related hydroxystilbene compounds (2-9) isolated from plants were evaluated for the anti-allergic activities in vitro. Resveratrol (1) and rhapontigenin (5) demonstrated significant inhibitions upon the release of β-hexosaminidase
Novel resveratrol-based flavonol derivatives: Synthesis and anti-inflammatory activity in vitro and in vivo
Chen, Liu Zeng,Yao, Li,Jiao, Ming Ming,Shi, Jing Bo,Tan, Yue,Ruan, Ban Feng,Liu, Xin Hua
, p. 114 - 128 (2019)
In order to discover novel anti-inflammatory agents, total thirty-seven new resveratrol-based flavonol derivatives were designed and synthesized. All compounds have been screened for their anti-inflammatory activity by evaluating their inhibition effect of LPS-induced NO production in RAW 264.7 macrophages. Their toxicity was also assessed in vitro. Structure-activity relationships (SARs)have been concluded, and finally 2-(2,4-dimethoxy-6-(4-methoxystyryl)phenyl)-3-hydroxy-4H-chromen-4-one was found to be the most active scaffold with low toxicity. This compound could significantly decrease productions of NO, IL-6 and TNF-α with IC50 values of 1.35, 1.12 and 1.92 μM, respectively in RAW 264.7 macrophages. Preliminary mechanism studies indicated that it could inhibit the expression of TLR4 protein, resulting in activation of the NF-?B cell signaling pathway. The in vivo anti-inflammatory activity of this compound could reduce pulmonary inflammation by mouse model of LPS-induced acute lung injury (ALI). We believe these findings would further support studies of rational design of more efficient acute lung injury regulatory inhibitors.
A new synthesis of resveratrol
Lara-Ochoa, Francisco,Sandoval-Minero, Leticia C.,Espinosa-Pérez, Georgina
, p. 5977 - 5979 (2015)
Resveratrol was synthesized in a 4-step synthesis using a simple Sonogashira type reaction with 93% yield using commercially available 3,5-dimethoxy-1-ethynyl-benzene and 4-iodoanisole, followed by reduction, isomerization, and deprotection and with an overall yield of 63%.
Resveratrol and trimethylated resveratrol protect from acute liver damage induced by CCI4 in the rat
Rivera, Horacio,Shibayama, Mineko,Tsutsumi, Victor,Perez-Alvarez, Victor,Muriel, Pablo
, p. 147 - 155 (2008)
The importance of hydroxyl groups in the antioxidant and hepatoprotective properties of resveratrol was investigated. To achieve this, resveratrol or its trimethylated analog were administered (10 mg kg-1, p.o.) to male Wistar rats and liver damage was induced by acute administration of CCl 4 (4 g kg-1, p.o.); appropriate controls were performed. The animals were killed 24 h after CCl4 intoxication. The amount of reduced glutathione (GSH) in the liver was not modified by any treatment; interestingly, the GSH/GSSG (oxidized glutathione) ratio decreased in the groups receiving CCl4 and resveratrol associated with an increase in GSSG. In blood GSH and the GSH/GSSG ratio were decreased by CCl4; both effects were completely prevented by any of the compounds tested. Lipid peroxidation and the activity of γ-glutamyl transpeptidase were increased significantly after CCl4. Resveratrol partially prevented these increases and surprisingly, trimethylated resveratrol completely prevented the increase of these markers. Both compounds partially but significantly prevented the increase in the activity of alanine aminotransferase; this result agrees with observations in the histological analysis. Both tested compounds administered alone produced no effect. The results of the present study suggest that OH groups are important for the antioxidant and hepatoprotective properties of the molecule of resveratrol; nevertheless, these effects can be improved by replacing hydrogen by a methyl in these groups. The differences in the antioxidant and hepatoprotective effects of these compounds could be due to the possibility that the trimethylated resveratrol acts like a prodrug, prolonging, probably, the half-life of the original compound. Copyright
Application of chromium-arene complexes in the organic synthesis. Efficient synthesis of stilbene phytoalexins
Polunin,Schmalz
, p. 252 - 261 (2004)
Planar chiral η6-arene-Cr(CO)3 complexes represent highly valuable building blocks for the diastereo- and enantioselective synthesis. Their employment as synthons offer new and unique opportunities for the stereoselective multistep synthesis of complex natural products. The strategy of novel efficient synthesis of stilbene phytoalexins was based on arene chromium chemistry and the chemical and stereochemical effects of the metal unit on the reactivity of complexed arene ligand and stereochemical features of such compounds. Two variants for the construction of the trans-stilbene and diarylethanol framework via facilitated benzylic deprotonation of an η6benzene-Cr(CO)3 complex and subsequent coupling with para-anisaldehyde in an aldol-type or a Wittig-Horner reaction were suggested.
An expedient synthesis of resveratrol through a highly recoverable palladium catalyst
Martínez, Alejandro V.,García, José I.,Mayoral, José A.
, p. 5581 - 5584 (2017)
A straightforward two-step synthesis of resveratrol is described, with total isolated yields in the range of 75–80%. The key synthetic step, a Heck–Mizoroki C[sbnd]C cross-coupling reaction, is efficiently promoted by a heterogeneous catalyst consisting of palladium nanoparticles supported on synthetic clay. This solid catalyst is quite handy and displays high stability and robustness under reaction conditions. The catalyst can be easily recovered and reused at least 10 times, which improves the overall catalytic efficiency of the system. Moreover, the use of solvents is limited, and the reaction procedure allows a facile separation and purification of the desired product, free from the concomitant ionic by-product and from palladium contamination.
PACHARIN: A NEW DIBENZO(2,3-6,7)OXEPIN DERIVATIVE FROM BAUHINIA RACEMOSA LAMK
Anjaneyulu, A. S. R.,Raghava Reddy, A. V.,Reddy, D. S. K.,Ward, R. S.,Adhikesavalu, D.,Cameron, T. Stanley
, p. 4245 - 4252 (1984)
The isolation of resveratrol and a new dibenzoxepin derivative, pacharin, from the heartwood of Bauhinia racemosa Lamk is reported.The structure of pacharin has been established as 1,7-dihydroxy-3-methoxy-2-methyl-dibenzo(2,3-6,7)oxepin (Va) by a study of its chemical and spectroscopic properties, including X-ray analysis.
