- Structure-activity relationship studies of resveratrol and its analogues by the reaction kinetics of low density lipoprotein peroxidation
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Resveratrol (3,5,4′-trans-trihydroxystibene) is a natural phytoalexin present in grapes and red wine, which possesses a variety of biological activities including antioxidative activity. To find more active antioxidants, with resveratrol as the lead compo
- Cheng, Jin-Chun,Fang, Jian-Guo,Chen, Wei-Feng,Zhou, Bo,Yang, Li,Liu, Zhong-Li
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Read Online
- Evaluation of Manassantin A Tetrahydrofuran Core Region Analogues and Cooperative Therapeutic Effects with EGFR Inhibition
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Tumors adapt to hypoxia by regulating angiogenesis, metastatic potential, and metabolism. These adaptations mediated by hypoxia-inducible factor 1 (HIF-1) make tumors more aggressive and resistant to chemotherapy and radiation. Therefore, HIF-1 is a validated therapeutic target for cancer. In order to develop new HIF-1 inhibitors for cancer chemotherapy by harnessing the potential of the natural product manassantin A, we synthesized and evaluated manassantin A analogues with modifications in the tetrahydrofuran core region of manassantin A. Our structure-activity relationship study indicated that the α,α′-trans-configuration of the central ring of manassantin A is critical to HIF-1 inhibition. We also demonstrated that a combination of manassantin A with an epidermal growth factor receptor inhibitor shows cooperative antitumor activity (~80% inhibition for combination vs ~30% inhibition for monotherapy). Our findings will provide important frameworks for the future therapeutic development of manassantin A-derived chemotherapeutic agents.
- Kwak, Seung-Hwa,Stephenson, Tesia N.,Lee, Hye-Eun,Ge, Yun,Lee, Hyunji,Min, Sophia M.,Kim, Jea Hyun,Kwon, Do-Yeon,Lee, You Mie,Hong, Jiyong
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p. 6821 - 6833
(2020/07/14)
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- Synthesis of potential bisphenol A substitutes by isomerising metathesis of renewable raw materials
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Isomerising metathesis is introduced as a sustainable method to produce dihydroxystilbene derivatives from eugenol, a clove oil ingredient, and cardanol from cashew nut shell liquid. Hydrogenation of the dihydroxystilbenes provided their di(hydroxyphenyl)ethane analogues. Initial studies to convert these monomers into polycarbonates and thiol-ene polymers support their potential to replace the petrol-derived bisphenol A (BPA). The estrogenic activity of the monomers derived from cardanol was found to be in the same range as that of BPA, a known endocrine disruptor. In contrast, eugenol-derived materials were found to be non-estrogenic, opening up new perspectives for bio-based food packaging materials.
- Trita,Over,Pollini,Baader,Riegsinger,Meier,Goo?en
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supporting information
p. 3051 - 3060
(2017/07/15)
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- A One-Pot Cascade Reaction Combining an Encapsulated Decarboxylase with a Metathesis Catalyst for the Synthesis of Bio-Based Antioxidants
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The combination of enzymes with traditional chemical catalysts unifies the high selectivity of the former with the versatility of the latter. A major challenge of this approach is the difference in the optimal reaction conditions for each catalyst type. In this work, we combined a cofactor-free decarboxylase with a ruthenium metathesis catalyst to produce high-value antioxidants from bio-based precursors. As suitable ruthenium catalysts did not show satisfactory activity under aqueous conditions, the reaction required the use of an organic solvent, which in turn significantly reduced enzyme activity. Upon encapsulation of the decarboxylase in a cryogel, the decarboxylation could be conducted in an organic solvent, and the recovery of the enzyme after the reaction was facilitated. After an intermediate drying step, the subsequent metathesis in pure organic solvent proved to be straightforward. The synthetic utility of the cascade was demonstrated by the synthesis of the antioxidant 4,4′-dihydroxystilbene in an overall yield of 90 %.
- Gómez Baraibar, álvaro,Reichert, Dennis,Mügge, Carolin,Seger, Svenja,Gr?ger, Harald,Kourist, Robert
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p. 14823 - 14827
(2016/11/23)
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- Synthesis of bio-based epoxy monomers from natural allyl- and vinyl phenols and the estimation of their affinity to the estrogen receptor α by molecular docking
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Diepoxydized diphenyls from eugenol, 4-vinyl guaiacol and 4-vinyl syringol (canolol) were synthesized as sustainable alternatives to the diglycidyl ether of bisphenol A (DGEBA). In the first step, glycidylated derivatives were produced by reaction with epichlorohydrin. Then, the dimerization of these derivatives was performed by cross metathesis (CM) reaction in the presence of the Grubbs II catalyst. From the CM reaction, a set of epoxy phenolic dimers was obtained in good yields with a high diastereoselectivity. Estimation by molecular docking calculations of the affinity of the synthesized products and their hydrolysed structures to the intranuclear estrogen receptor ERα showed that the epoxy forms presented a moderate affinity to the antagonistic conformation of the receptor (six to forty times lower than bisphenol A and in the same order of magnitude as DGEBA) and mostly no binding in the agonist conformation. The hydrolysed forms of the epoxy products, which are expected to be predominant in the human body cells, exhibited a relatively weak affinity to the ERα LBD in its both agonistic and antagonistic conformations.
- Zago, Erika,Dubreucq, Eric,Lecomte, Jér?me,Villeneuve, Pierre,Fine, Frédéric,Fulcrand, Hélène,Aouf, Chahinez
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p. 7701 - 7710
(2016/09/12)
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- NOVEL 1,2-DIPHENYLETHYLENE GLYCOL COMPOUNDS FOR COMBATING AGING OF THE SKIN, AND COSMETIC USE THEREOF
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The present invention relates to novel compounds of formula (I) to cosmetic compositions comprising same, and also to the use thereof for preventing and/or cosmetically treating the signs of aging of the skin.
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Page/Page column 25
(2016/07/05)
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- Flash-metathesis for the coupling of sustainable (poly)hydroxyl β-methylstyrenes from essential oils
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A cross-metathesis procedure was developed to synthetize symmetrical and non symmetrical stilbenes from sustainable resources. The reaction proceeds under solvent-free conditions and at low catalyst loading (down to 0.01 mol%) within a couple of minutes only (TOF up to 6.9 s-1), on multi-gram scale. The highly reactive β-methylstyrene substrates were homo-coupled not only as pure synthons but also as components of essential oils that were reacted directly in order to eliminate prior substrate isolation from the overall process.
- Hitce,Crutizat,Bourdon,Vivès,Marat,Dalko-Csiba
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p. 3756 - 3761
(2015/07/15)
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- Renewable thermosetting resins and thermoplastics from vanillin
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Two cyanate ester resins and a polycarbonate thermoplastic have been synthesized from vanillin. The bisphenol precursors were prepared by both an electrochemical route as well as by a McMurry coupling reaction. 1,2-Bis(4-cyanato-3-methoxyphenyl)ethene (6) had a high melting point of 237 °C and did not cure completely under a standard cure protocol. In contrast, the reduced version, 1,2-bis(4-cyanato-3-methoxyphenyl)ethane (7) melted at 190 °C and underwent complete cure to form a thermoset material with Tg = 202 °C. 7 showed thermal stability up to 335 °C and decomposed via formation of phenolics and isocyanic acid. A polycarbonate was then synthesized from the reduced bisphenol by a transesterification reaction with diphenylcarbonate. The polymer had Mn = 3588, Mw/Mn = 1.9, and a Tg of 86 °C. TGA/FTIR data suggested that the polycarbonate decomposed via formation of benzodioxolones with concomitant elimination of methane. The results show that vanillin is a useful precursor to both thermosetting resins and thermoplastics without significant modification. This journal is
- Harvey, Benjamin G.,Guenthner, Andrew J.,Meylemans, Heather A.,Haines, Shannon R. L.,Lamison, Kevin R.,Groshens, Thomas J.,Cambrea, Lee R.,Davis, Matthew C.,Lai, William W.
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p. 1249 - 1258
(2015/03/04)
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- Tandem heck/decarboxylation/heck strategy: Protecting-group-free synthesis of symmetric and unsymmetric hydroxylated stilbenoids
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Ride the (micro)wave: The title strategy has been developed for the synthesis of various symmetric or unsymmetric hydroxylated stilbenoids utilizing 4-halophenols and acrylic acid as coupling partners (see scheme; DMA=N,N-dimethylacetamide, MW=microwave). Protecting groups are not necessary and a single palladium catalyst is used. Copyright
- Shard, Amit,Sharma, Naina,Bharti, Richa,Dadhwal, Sumit,Kumar, Rajesh,Sinha, Arun K.
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supporting information
p. 12250 - 12253
(2013/02/22)
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- Stereoselective synthesis of (E)-hydroxystilbenoids by ruthenium-catalyzed cross-metathesis
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An efficient and highly stereoselective synthetic procedure is reported for the construction of symmetrical and unsymmetrical (E)-polymethoxystilbene and (E)-polyhydroxystilbene derivatives. The strategy rests on a cross-metathesis reaction catalyzed by stable, well-defined (alkylidene)ruthenium complexes, in particular the second-generation Grubbs catalyst [RuCl2(=CHPh)(SIMes) (PCy3)] [SIMes = 1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2- ylidene]. The metathesis of unprotected phenolic styrenes is illustrated by the synthesis of the important phytoalexins (E)-3,4′,5-trihydroxystilbene (resveratrol) and (E)-3,3′,4,5′-tetrahydroxystilbene (piceatannol). Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
- Ferre-Filmon, Karine,Delaude, Lionel,Demonceau, Albert,Noels, Alfred F.
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p. 3319 - 3325
(2007/10/03)
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- Low-valent titanium mediated synthesis of hydroxystilbenoids: Some new observations
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A series of phenolic stilbenoids possessing different numbers and positions of hydroxylation, partial methoxyl substituents and nature of olefinic moieties has been synthesized by McMurry coupling. It is found that the McMurry coupling of the phenolic aldehydes furnishes the dihydrostilbenes via an in situ hydrogenation, while the phenolic ketones give the stilbenes. Interestingly, the study also reveals that the low-valent titanium reagent (TiCl 3-Zn-THF) could selectively depyranylate phenolic -OTHP function without affecting alcoholic -OTHP group.
- Shadakshari,Rele,Nayak,Chattopadhyay
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p. 1934 - 1938
(2007/10/03)
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- Purification and Some Properties of the Enzyme Catalyzing the Cγ-Elimination of a Diarylpropane-type Lignin Model from Pseudomonas paucimobilis TMY 1009
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A novel enzyme catalyzing the Cγ-elimination of a diarylpropane-type lignin model, erythro-1,2-bis(4-hydroxy-3-methoxyphenyl)-propane-1,3-diol, was purified from a cell free extract of Pseudomonas paucimobilis TMY 1009.When the diarylpropane was decomposed by the purified enzyme, equimolar amounts of 1,2-bis(4-hydroxy-3-methoxyphenyl)-ethylene and formaldehyde were produced as reaction products, suggesting that the enzymatic reaction is Cγ-deformylation accompanied with dehydroxylation at the Cα-position.Consequently, this enzyme was designated tentatively as diarylpropane formaldehyde lyase.The optimum pH for the enzyme acti vity was around 7.5 and the Km value for the diarylpropane was 71 μM.This enzyme was seemed to be composed of two identical subunits and the molecular weight of the native enzyme was estimated to be 80,000.
- Kishi, Katsuyuki,Habu, Naoto,Samejima, Masahiro,Yoshimoto, Tomotaka
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p. 1319 - 1323
(2007/10/02)
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- SELECTIVE DEACETYLATION OF AROMATIC ACETATES BY AMINOLYSIS
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Pyrrolidine was shown to deacetylate aromatic acetyl groups considerably faster than aliphatic groups.
- Mansson, Per
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p. 1845 - 1846
(2007/10/02)
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