- New long-chained feruloyl ester from the bark of Cedrelinga catenaeformis
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Tetradecyl ferulate and a new n-alkyl ester of 3-hydroxy-4-methoxy-trans- cinnamate (hexacosanylisoferulate) have been isolated from Cedrelinga catenaeformis Duke (Leguminoseae). The structures were determined by 1D- and 2D-NMR spectroscopy, mass spectrometry, chemical transformations and finally from unambiguous synthesis. This is the first report of long chained cinnamic acid ester derivative from the genus.
- El-Seedi
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- Isoferuloyl derivatives of five seed glucosinolates in the crucifer genus Barbarea
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Five acylated glucosinolates (GSLs) were isolated as desulfated derivatives after enzymatic desulfation of anionic metabolites from seeds of two chemotypes of Barbarea vulgaris, and their structures were elucidated by a combination of spectroscopic methods and HPLC analysis of products of enzymatic de-acylation. The acyl group was in all cases found to be a trans isoferuloyl group at the 6′-position of the thioglucose moiety. The GSL moieties of the native metabolites were found to be one Trp derived; indol-3-ylmethylGSL, as well as four homoPhe derived; phenethylGSL, (S)-2-hydroxy-2-phenylethylGSL, (R)-2-hydroxy-2-phenylethylGSL, and (R)-2-hydroxy-2-(4-hydroxyphenyl)ethylGSL. GSL analysis of B. vulgaris seed extracts by the commonly employed 'desulfoGSL' method (based on binding to anion exchange columns, enzymatic desulfation, elution and HPLC) was optimized for 6′-isoferuloyl derivatives of GSLs. From peak areas before and after de-acylation of the isolated desulfoGSL, the response factor of the 6′-isoferuloyl derivative of (S)-2-hydroxy-2- phenylethylGSL was estimated to be 0.37 (relative to 1.00 for sinigrin), allowing us to estimate the level in B. vulgaris to 3 μmol/g dry wt. in mature seeds and less than 0.1 μmol/g dry wt. in seedlings and floral parts of the insect resistant G-type of B. vulgaris var. arcuata. HPLC analysis of intact GSLs in crude extracts and after group separation did not reveal additional derivatives, but confirmed the existence of the deduced intact GSLs. A taxonomic screen showed that most (14/17) B. vulgaris accessions (with the exception of three accessions of var. vulgaris) contained relatively high levels of 6′-isoferuloyl GSLs. The profiles of 6′-isoferuloylated GSLs matched the profiles of non-acylated GSLs in the same seed accessions, suggesting a low side chain specificity of the isoferuloylation mechanism. A minor peak tentatively identified as a dimethoxycinnamoyl derivative of (S)-2-hydroxy-2-phenylethylGSL was detected by HPLC-MS of one accession, suggesting that GSLs with other acyl groups may occur at low levels. A single analyzed B. plantaginae accession contained relatively high levels of 6′-isoferuloylated phenethylGSL and (S)-2-hydroxy-2-phenylethylGSL. Five other tested Barbarea species (B. australis, B. bracteosa, B. intermedia, B. stricta, B. verna) also contained isoferuloylated GSLs, albeit at lower levels than in B. vulgaris and B. plantaginae, suggesting that seed GSL acylation is a general character of the Barbarea genus and possibly also of related genera including Arabidopsis.
- Agerbirk, Niels,Olsen, Carl Erik
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- ERYTHRINASINATE, AN ESTER FROM THREE ERYTHRINA SPECIES
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The novel ester n-octacosanyl-3-hydroxy-4-methoxy cinnamate has been isolated from the stem bark of Erythrina senegalensis, E. glauca and E. mildbaedii and its structure determined by spectroscopic data and degradative studies.The known pterocarpan erythrabyssin-1 has also been isolated from E. glauca.Key Word Index - Erythrina senegalensis; E. glauca; E. mildbraedii; Leguminosae; erythrinasinate; pterocarpan; erythrabyssin-1.
- Fomum, Z. Tanee,Ayafor, J. Foyere,Wandji, Jean,Fomban, W. Gana,Nkengfack, A. Ephrem
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- Bioassay of ferulic acid derivatives as influenza neuraminidase inhibitors
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Four series of ferulic acid derivatives were designed, synthesized, and evaluated for their neuraminidase (NA) inhibitory activities against influenza virus H1N1 in vitro. The pharmacological results showed that the majority of the target compounds exhibited moderate influenza NA inhibitory activity, which was also better than that of ferulic acid. The two most potent compounds were 1m and 4a with IC50 values of 12.77 ± 0.47 and 12.96 ± 1.34 μg/ml, respectively. On the basis of the biological results, a preliminary structure–activity relationship (SAR) was derived and discussed. Besides, molecular docking was performed to study the possible interactions of compounds 1p, 2d, 3b, and 4a with the active site of NA. It was found that the 4-OH-3-OMe group and the amide group (CON) of ferulic acid amide derivatives were two key pharmacophores for NA inhibitory activity. It is meaningful to further modify the natural product ferulic acid to improve its influenza NA inhibitory activity.
- Cui, Man-Ying,Xiao, Meng-Wu,Xu, Lv-Jie,Chen, Yun,Liu, Ai-Lin,Ye, Jiao,Hu, Ai-Xi
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- Copper and L-(?)-quebrachitol catalyzed hydroxylation and amination of aryl halides under air
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L-(?)-Quebrachitol, a natural product obtained from waste water of the rubber industry, was utilized as an efficient ligand for the copper-catalyzed hydroxylation and amination of aryl halides to selectively give phenols and aryl amines in water or 95percent ethanol. In addition, the hydroxylation of 2-chloro-4-hydroxybenzoic acid was validated on a 100-g scale under air.
- Bao, Xuefei,Chen, Guoliang,Dong, Jinhua,Du, Fangyu,Li, Hui,Liang, Xinjie,Wu, Ying,Zhang, Yongsheng
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supporting information
(2020/08/03)
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- Regioselectivity of Cobalamin-Dependent Methyltransferase Can Be Tuned by Reaction Conditions and Substrate
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Regioselective reactions represent a significant challenge for organic chemistry. Here the regioselective methylation of a single hydroxy group of 4-substituted catechols was investigated employing the cobalamin-dependent methyltransferase from Desulfitobacterium hafniense. Catechols substituted in position four were methylated either in meta- or para-position to the substituent depending whether the substituent was polar or apolar. While the biocatalytic cobalamin dependent methylation was meta-selective with 4-substituted catechols bearing hydrophilic groups, it was para-selective for hydrophobic substituents. Furthermore, the presence of water miscible co-solvents had a clear improving influence, whereby THF turned out to enable the formation of a single regioisomer in selected cases. Finally, it was found that also the pH led to an enhancement of regioselectivity for the cases investigated.
- Pompei, Simona,Grimm, Christopher,Farnberger, Judith E.,Schober, Lukas,Kroutil, Wolfgang
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p. 5977 - 5983
(2020/10/06)
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- Structural features and antioxidant activities of Chinese quince (Chaenomeles sinensis) fruits lignin during auto-catalyzed ethanol organosolv pretreatment
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Chinese quince fruits (Chaenomeles sinensis) have an abundance of lignins with antioxidant activities. To facilitate the utilization of Chinese quince fruits, lignin was isolated from it by auto-catalyzed ethanol organosolv pretreatment. The effects of three processing conditions (temperature, time, and ethanol concentration) on yield, structural features and antioxidant activities of the auto-catalyzed ethanol organosolv lignin samples were assessed individually. Results showed the pretreatment temperature was the most significant factor; it affected the molecular weight, S/G ratio, number of β-O-4′ linkages, thermal stability, and antioxidant activities of lignin samples. According to the GPC analyses, the molecular weight of lignin samples had a negative correlation with pretreatment temperature. 2D-HSQC NMR and Py-GC/MS results revealed that the S/G ratios of lignin samples increased with temperature, while total phenolic hydroxyl content of lignin samples decreased. The structural characterization clearly indicated that the various pretreatment conditions affected the structures of organosolv lignin, which further resulted in differences in the antioxidant activities of the lignin samples. These results can be helpful for controlling and optimizing delignification during auto-catalyzed ethanol organosolv pretreatment, and they provide theoretical support for the potential applications of Chinese quince fruits lignin as a natural antioxidant in the food industry.
- Cheng, Xi-Chuang,Guo, Xin-Ran,Liu, Hua-Min,Liu, Yu-Lan,Qin, Zhao,Wang, Xue-De
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p. 4348 - 4358
(2020/09/22)
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- Synthesis and biological evaluation of 2,2-dimethylbenzopyran derivatives as potent neuroprotection agents
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The development of novel neuroprotection agents is of great significance for the treatment of ischemic stroke. In this study, a series of compounds comprising 2,2-dimethylbenzopyran groups and cinnamic acid groups have been synthesized. Preferential combination principles and bioisostere that improved the neuroprotective effect of the compounds were identified for this series via biological activity assay in vitro. Meanwhile, a functional reversal group of the acrylamide amide resulted in the most active compounds. Among them, BN-07 significantly improved the morphology of neurons and obviously increased cell survival rate of primary neurons induced by oxygen glucose deprivation (OGD), superior to clinically used anti-ischemic stroke drug edaravone (Eda). Overall, our findings may provide an alternative strategy for the design of novel anti-ischemic stroke agents with more potency than Eda.
- Du, Fangyu,Zhou, Qifan,Fu, Xiaoxiao,Shi, Yajie,Chen, Yuanguang,Fang, Wuhong,Yang, Jingyu,Chen, Guoliang
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p. 2498 - 2508
(2019/02/01)
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- Substituted cinnamic anhydrides act as selective inhibitors of acetylcholinesterase
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Cinnamic anhydrides have been shown to be more than reactive reagents, but they also act as inhibitors of the enzyme acetylcholinesterease (AChE). Thus, out of a set of 33 synthesised derivatives, several of them were mixed type inhibitors for AChE (from electric eel). Thus, (E)-3-(2,4-dimethoxyphenyl)acrylic anhydride (2c) showed Ki = 8.30 ± 0.94 μM and Ki′ = 9.54 ± 0.38 μM, and for (E)-3-(3-chlorophenyl)acrylic anhydride (2u) Ki = 8.23 ± 0.93 μM and Ki′ = 13.07 ± 0.46 μM were measured. While being not cytotoxic to many human cell lines, these compounds showed an unprecedented and noteworthy inhibitory effect for AChE but not for butyrylcholinesterase (BChE).
- Gie?el, Josephine M.,Serbian, Immo,Loesche, Anne,Csuk, René
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- Specific Residues Expand the Substrate Scope and Enhance the Regioselectivity of a Plant O-Methyltransferase
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An isoeugenol 4-O-methyltransferase (IeOMT), isolated from the plant Clarkia breweri, can be engineered to a caffeic acid 3-O-methyltransferase (CaOMT) by replacing three consecutive residues. Here we further investigated functions of these residues by constructing the triple mutant T133M/A134N/T135Q as well as single mutants of each residue. Phenolics with different chain lengths and different functional groups were investigated. The variant T133M improves the enzymatic activities against all tested substrates by providing beneficial interactions to residues which directly interact with the substrate. Mutant A134N significantly enhanced the regioselectivity. It is meta-selective or even specific against most of the tested substrates but para-specific towards 3,4-dihydroxybenzoic acid. The triple mutant T133M/A134N/T135Q benefits from these two mutations, which not only expand the substrate scope but also enhance the regioselectivity of IeOMT. On the basis of our work, regiospecific methylated phenolics can be produced in high purity by different IeOMT variants.
- Tang, Qingyun,Bornscheuer, Uwe T.,Pavlidis, Ioannis V.
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p. 3227 - 3233
(2019/07/04)
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- Application of quebrachitol in hydrolysis reaction of copper-catalyzed aryl halide
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The invention belongs to the technical field of drug synthesis, and provides application of quebrachitol in a hydrolysis reaction of a copper-catalyzed aryl halide. According to the hydrolysis reaction, copper serves as a catalyst, quebrachitol serves as a ligand, and the hydrolysis reaction is carried out on the aryl halide. The invention further provides a catalytic system of the hydrolysis reaction of the aryl halide. The reaction system comprises the copper catalyst, the quebrachitol, alkali and water, and the system is environmentally friendly and is suitable for industrial application.
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Paragraph 0072-0074
(2019/07/16)
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- Discovery of caffeic acid phenethyl ester derivatives as novel myeloid differentiation protein 2 inhibitors for treatment of acute lung injury
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Myeloid differentiation protein 2 (MD2) is an essential molecule which recognizes lipopolysaccharide (LPS), leading to initiation of inflammation through the activation of Toll-like receptor 4 (TLR4) signaling. Caffeic acid phenethyl ester (CAPE) from propolis of honeybee hives could interfere interactions between LPS and the TLR4/MD2 complex, and thereby has promising anti-inflammatory properties. In this study, we designed and synthesized 48 CAPE derivatives and evaluated their anti-inflammatory activities in mouse primary peritoneal macrophages (MPMs) activated by LPS. The most active compound, 10s, was found to bind with MD2 with high affinity, which prevented formation of the LPS/MD2/TLR4 complex. The binding mode of 10s revealed that the major interactions with MD2 were established via two key hydrogen bonds and hydrophobic interactions. Furthermore, 10s showed remarkable protective effects against LPS-caused ALI (acute lung injury) in vivo. Taken together, this work provides new lead structures and candidates as MD2 inhibitors for the development of anti-inflammatory drugs.
- Chen, Lingfeng,Jin, Yiyi,Chen, Hongjin,Sun, Chuchu,Fu, Weitao,Zheng, Lulu,Lu, Min,Chen, Pengqin,Chen, Gaozhi,Zhang, Yali,Liu, Zhiguo,Wang, Yi,Song, Zengqiang,Liang, Guang
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p. 361 - 375
(2017/12/07)
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- 2,2-dimethylbenzopyran derivative and preparation method and use thereof
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The invention belongs to the technical field of medicines, and discloses a 2,2-dimethylbenzopyran derivative and a preparation method and use of the 2,2-dimethylbenzopyran derivative. The derivative and pharmaceutically acceptable salt of the derivative have the structural formulae shown in the description, wherein Ar, Ar, X, Y and R1 are as described in the claims and the description. The preparation methods of the derivative and the pharmaceutically acceptable salt of the derivative comprise the following steps: the formula (I) is obtained by mainly taking acetaminophen as a raw material, and subjected to the reactions of Williamson ether formation, cyclization, hydrolysis, amide formation and the like; the formula II is obtained by mainly taking p-hydroxybenzaldehyde as a raw material, and subjected to the reactions of the Williamson ether formation, cyclization, Knoevenagel condensation, amide formation and the like. The derivative and the pharmaceutically acceptable salt ofthe derivative disclosed by the invention can be used for preparing neuroprotective agents and have better neuroprotective effects on ischemic stroke.
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Page/Page column 13; 14
(2019/01/16)
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- Synthesis and biological evaluation of novel neoflavonoid derivatives as potential antidiabetic agents
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Various substituted neoflavonoid derivatives were synthesized using sulfated montmorillonite K-10 as a catalyst. This method is environmental friendly, sustainable and economical, convenient in isolation and purification processes, with little byproducts, using earth-abundant catalysts and has relatively high yield. Those neoflavonoid derivatives were screened for antioxidant, a-glucosidase inhibitory, aldose reductase 2 (ALR2) inhibitory and advanced glycation end-product formation inhibitory effects. Most compounds exhibited significant antioxidant and advanced glycation end-product (AGE) formation inhibitory activities. It was interesting to note that out of thirty compounds, 8k and 8l were found to have greater ALR2 inhibitory activity than the standard drug quercetin. The pharmacological studies suggested neoflavonoid with adjacent 7,8-dihydroxy groups were more effective in inhibiting ALR2. Antidiabetic activity studies had shown that compounds 8l and 8m were equipotent to the standard drug glibenclamide in vivo. In summary, the target compound 8l provided a potential drug design concept for the development of therapeutic or prophylactic agents of diabetes and diabetes complications.
- Wang, Bing,Li, Na,Liu, Teng,Sun, Jie,Wang, Xiaojing
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p. 34448 - 34460
(2017/07/22)
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- Preparation method of 3,4-dihydro-4-arylcoumarin compounds
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The invention relates to the field of chemical synthesis, and concretely relates to a preparation method of 3,4-dihydro-4-arylcoumarin compounds. The method is characterized in that: substituted benzaldehyde is used as an initial raw material, propane diacid is added, a reaction is carried out with catalysis of piperidine, and substituted phenyl acrylic acid derivatives are obtained; montmorillonite K-10 which is acidified by sulfuric acid is used as a catalyst, a reaction between the substituted phenyl acrylic acid derivatives and phenolic compounds is carried out with heating, and the 3,4-dihydro-4-arylcoumarin compounds are obtained. Compared with the prior art, the preparation method of the 3,4-dihydro-4-arylcoumarin compounds has the advantages of easily available and cheap raw materials, simple operation, recyclable catalyst, environmental protection, simple post-treatment, low production cost, good promotion application, etc.
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Paragraph 0065
(2016/11/14)
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- Preparation method of neoflavonoids
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The invention relates to the field of chemical synthesis, in particular to a preparation method of neoflavonoids. The preparation method is characterized by comprising the following steps of using substituted benzaldehyde as an initial raw material to be reacted with malonic acid to generate a substituted phenylacrylic acid compound; performing an addition reaction, an elimination reaction and the like on the substituted phenylacrylic acid compound, or performing acetylation so as to protect a phenolic hydroxyl group, then performing a bromination reaction and the elimination reaction so as to synthesize the substituted phenylpropiolic acid compound ; and using montmorillonite K-10 after being acidulated by sulfuric acid as a catalyst, enabling the substituted phenylpropiolic acid compound and a phenolic compound to perform a heating reaction so as to generate the neoflavonoids. Compared with the prior art, the preparation method of the neoflavonoids, disclosed by the invention, has the characteristics that raw materials are cheap, and easy to obtain, the operation is simple, the catalyst can be recovered for use, and the method is environmentally-friendly, the post-treatment is simple, and the production cost is low, and the method has a high popularization and application value.
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Paragraph 0094; 0095
(2017/04/26)
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- Monoamine Oxidase Inhibitory Activity of Ferulic Acid Amides: Curcumin-Based Design and Synthesis
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Ferulic acid has structural similarity with curcumin which is being reported for its monoamine oxidase (MAO) inhibitory activity. Based on this similarity, we designed a series of ferulic acid amides 6a-m and tested for their inhibitory activity on human MAO (hMAO) isoforms. All the compounds were found to inhibit the hMAO isoforms either selectively or non-selectively. Nine compounds (6a, 6b, 6g-m) were found to inhibit hMAO-B selectively, whereas the other four (6c-f) were found to be non-selective. There is a gradual shift from hMAO-B selectivity (6a,b) to non-selectivity (6c-f) as there is an increase in chain length at the amino terminus. In case of compounds having an aromatic nucleus at the amino terminus, increasing the carbon number between N and the aromatic ring increases the potency as well as selectivity toward hMAO-B. Compounds 6f, 6j, and 6k were subjected to membrane permeability and metabolic stability studies by in vitro assay methods. They were found to have a better pharmacokinetic profile than curcumin, ferulic acid, and selegiline. In order to understand the structural features responsible for the potency and selectivity of 6k, we carried out a molecular docking simulation study.
- Badavath, Vishnu N.,Baysal, Ipek,Uar, Gülberk,Mondal, Susanta K.,Sinha, Barij N.,Jayaprakash, Venkatesan
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- Design, Synthesis and Pharmacological Evaluation of Novel Piperlongumine derivatives as Potential Antiplatelet Aggregation Candidate
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A series of novel piperlongumine derivatives (4a-i, 6a-i) were designed and synthesized. The inhibitory activities of platelet aggregation induced by ADP and AA in vitro have been evaluated by bron turbidimetry and liver microsomal incubated assay. The assay results show that compounds 4e and 6e exhibited remarkable potency to that of the positive control piplartine and aspirin.
- Wang, Yujun,Wang, Jie,Li, Jiaming,Zhang, Yanchun,Huang, Weijun,Zuo, Jian,Liu, Huicai,Xie, Di,Zhu, Panhu
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p. 833 - 840
(2016/05/19)
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- Alkaloids and phenolic glycosides from Clematis mandshurica and their inhibitory effects against NO production in LPS-induced RAW 246.7 macrophages
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Two new alkaloids (1 and 2), one new phenolic glycoside (3), and five known structures (4–8) were isolated from the roots and rhizomes of Clematis mandshurica. Their structures were elucidated on the basis of spectroscopic evidence and hydrolysis products
- Fu, Qiang,Chen, Jiang,Yuan, Hai-Mei,Ma, Yu,Yu, Tian,Zou, Liang
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p. 238 - 241
(2016/08/15)
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- Recyclable Hypervalent-Iodine-Mediated Dehydrogenative α,β′-Bifunctionalization of β-Keto Esters under Metal-Free Conditions
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We have developed a method for recyclable hypervalent-iodine-mediated direct dehydrogenative α,β′- bifunctionalization of β-ketoesters and β-diketones under metal-free conditions, which affords a straightforward way to synthesize benzo-fused 2,3-dihydrofurans. This efficient, mild method, which has a wide substrate scope and good functional-group tolerance, was used for the multistep synthesis of the protected aglycone of a naturally occurring phenolic glycoside. A mechanism involving Michael addition to an enone intermediate and subsequent oxidative cyclization is proposed.
- Duan, Ya-Nan,Cui, Li-Qian,Zuo, Lin-Hong,Zhang, Chi
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supporting information
p. 13052 - 13057
(2015/09/07)
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- Search for novel histone deacetylase inhibitors. Part II: Design and synthesis of novel isoferulic acid derivatives
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Previously, we described the discovery of potent ferulic acid-based histone deacetylase inhibitors (HDACIs) with halogeno-acetanilide as novel surface recognition moiety (SRM). In order to improve the affinity and activity of these HDACIs, twenty seven isoferulic acid derivatives were described herein. The majority of title compounds displayed potent HDAC inhibitory activity. In particular, IF5 and IF6 exhibited significant enzymatic inhibitory activities, with IC50 values of 0.73 ± 0.08 and 0.57 ± 0.16 μM, respectively. Furthermore, these compounds showed moderate antiproliferative activity against human cancer cells. Especially, IF6 displayed promising profile as an antitumor candidate with IC50 value of 3.91 ± 0.97 μM against HeLa cells. The results indicated that these isoferulic acid derivatives could serve as promising lead compounds for further optimization.
- Lu, Wen,Wang, Fang,Zhang, Tao,Dong, Jinyun,Gao, Hongping,Su, Ping,Shi, Yaling,Zhang, Jie
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p. 2707 - 2713
(2014/05/06)
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- Design, synthesis and biological evaluation of novel trimethylpyrazine-2- carbonyloxy-cinnamic acids as potent cardiovascular agents
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A series of novel trimethylpyrazine-2-carbonyloxy-cinnamic acids and esters were designed, synthesized and evaluated for their inhibitory effect on adenosine diphosphate (ADP)-induced platelet aggregation in vitro and also assayed for their protective effect against hydrogen peroxide (H 2O2)-induced oxidative damage on Ea.hy926 cells. The results showed that many compounds exhibited high activity in one or both of the assays, of which, compound F′10 displayed the highest protective effect on the proliferation of the damaged Ea.hy926 cells (EC50 = 1.7 μM), presenting almost 40 times higher potency than that of lipoic acid, and compound F3 was the most active anti-platelet aggregation agent with IC 50 = 9.6 μM, comparable to that of clopidogrel. The structure-activity relationships of these compounds were also discussed.
- Chen, Hongfei,Li, Guoning,Zhan, Peng,Li, Hong,Wang, Shouxun,Liu, Xinyong
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supporting information
p. 711 - 718
(2014/06/10)
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- Synthesis, cytotoxicity and molecular modelling studies of new phenylcinnamide derivatives as potent inhibitors of cholinesterases
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The present study reports the synthesis of cinnamide derivatives and their biological activity as inhibitors of both cholinesterases and anticancer agents. Controlled inhibition of brain acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) may slow neurodegeneration in Alzheimer's diseases (AD). The anticholinesterase activity of phenylcinnamide derivatives was determined against Electric Eel acetylcholinesterase (EeAChE) and horse serum butyrylcholinesterase (hBChE) and some of the compounds appeared as moderately potent inhibitors of EeAChE and hBChE. The compound 3-(2-(Benzyloxy)phenyl)-N- (3,4,5-trimethoxyphenyl)acrylamide (3i) showed maximum activity against EeAChE with an IC50 0.29 ± 0.21 μM whereas 3-(2-chloro-6- nitrophenyl)-N-(3,4,5-trimethoxyphenyl)acrylamide (3k) was proved to be the most potent inhibitor of hBChE having IC50 1.18 ± 1.31 μM. To better understand the enzyme-inhibitor interaction of the most active compounds toward cholinesterases, molecular modelling studies were carried out on high-resolution crystallographic structures. The anticancer effects of synthesized compounds were also evaluated against cancer cell line (lung carcinoma). The compounds may be useful leads for the design of a new class of anticancer drugs for the treatment of cancer and cholinesterase inhibitors for Alzheimer's disease (AD).
- Saeed, Aamer,Mahesar, Parvez Ali,Zaib, Sumera,Khan, Muhammad Siraj,Matin, Abdul,Shahid, Mohammad,Iqbal, Jamshed
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- 1,5-DI-O-Isoferuloylquinic acid and other phenolic compounds from pollen of calendula officinalis
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A new phenylpropanoid that was identified as 1,5-di-O-isoferuloylquinic acid (1) and 17 known compounds including 1,5-di-O-feruloylquinic acid (2), which was obtained for the first time from a plant and was synthesized previously, were isolated from pollen of Calendula officinalis. Compounds 1 and 2 were the dominant phenolic compounds from pollen of C. officinalis. It was found that 1 possessed pronounced inhibitory activity against tyrosinase (IC50 11.26μg/mL).
- Olennikov,Kashchenko
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p. 589 - 593
(2015/02/02)
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- Three new triterpene saponins from Clematis chinensis
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Three new triterpene saponins, clematochinenosides H-J (1-3), were isolated from the roots and rhizomes of Clematis chinensis. Their structures were elucidated on the basis of spectroscopic means including 1D and 2D NMR experiments and hydrolysis products
- Fu, Qiang,Zan, Ke,Zhao, Ming-Bo,Zhou, Si-Xiang,Shi, She-Po,Jiang, Yong,Tu, Peng-Fei
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p. 610 - 618
(2013/07/26)
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- Catalytic enamines from dialkylamide-dialkylacetals
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The formation of a transient enamine derived from DMF-DMA provides an effective alternative to the harsh conditions normally required for the nucleophilic addition of base-activated methylene compounds to a carbonyl group. Organocatalysts formed from dialkylamide-dialkylacetals in this manner may provide extensive synthetic utility for a number of well-established reactions in which the formation of enolates and enamines has been employed.
- Davey, Roger M.,Stamford, N. Patrick J.
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experimental part
p. 2537 - 2539
(2012/06/30)
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- Synthesis of some phenylpropanoid glycosides (PPGs) and their acetylcholinesterase/xanthine oxidase inhibitory activities
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In this research, three categories of phenylpropanoid glycosides (PPGs) were designed and synthesized with PPGs isolated from Rhodiola rosea L. as lead compounds. Their inhibitory abilities toward acetylcholinesterase (AChE) and xanthine oxidase (XOD) were also tested. Some of the synthetic PPGs exhibited excellent enzyme inhibitory abilities.
- Li, Xiao-Dong,Kang, Shuai-Tao,Li, Guo-Yu,Li, Xian,Wang, Jin-Hui
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experimental part
p. 3580 - 3596
(2011/07/07)
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- Triterpene saponins from clematis chinensis and their potential anti-inflammatory activity
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Seven new triterpene saponins, clematochinenosides A-G (1-7), together with 17 known saponins (8-24), were isolated from the roots and rhizomes of Clematis chinensis. Their structures were elucidated on the basis of spectroscopic evidence and hydrolysis products. Compounds 1, 3-7, and 20-24 showed inhibitory activities against COX-1 and COX-2 enzymes.
- Fu, Qiang,Zan, Ke,Zhao, Mingbo,Zhou, Sixiang,Shi, Shepo,Jiang, Yong,Tu, Pengfei
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experimental part
p. 1234 - 1239
(2010/11/04)
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- Aphyllin, the first isoferulic acid glycoside and other phenolics from Tamarix aphylla flowers
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The first glycosylated isoferulic acid, isoferulic acid 3-O-β-glucopyranoside, together with the new phenolics, tamarixetin 3,3′-di-sodium sulphate and dehydrodigallic acid dimetyl ester have been characterized from a flower extract of Tamarix aphylla. Th
- Nawwar, Mahmoud A. M.,Hussein,Ayoub,Hofmann,Linscheid,Harms,Wende,Lindequist
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body text
p. 342 - 347
(2010/07/10)
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- One-pot two-step synthesis of 4-vinylphenols from 4-hydroxy substituted benzaldehydes under microwave irradiation: a new perspective on the classical Knoevenagel-Doebner reaction
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The classical Knoevenagel-Doebner reaction is reinvestigated wherein the direct synthesis of substituted 4-vinylphenols instead of the expected 4-hydroxycinnamic acids is described. The condensation reaction is performed on 4-hydroxy substituted benzaldehydes and malonic acid with a mixture of acetic acid-piperidine as condensing agent under focused microwave irradiation. The occurrence of simultaneous condensation-double decarboxylation without the use of any decarboxylating agent is a new finding, the reaction being facilitated solely by the hydroxy substituent and microwave irradiation effect.
- Sinha, Arun K.,Sharma, Anuj,Joshi, Bhupendra P.
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p. 960 - 965
(2007/10/03)
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- An efficient and fast synthesis of 4-aryl-3,4-dihydrocoumarins by (CF3SO3)3Y catalysis under microwave irradiation
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A new and efficient synthesis of eleven 4-aryl-3,4-dihydrocoumarins, in which six are new compounds, was performed using (CF3SO3)3Y as catalyst under microwave irradiation. The target compounds were obtained in good yields (68-80%) and remarkable time (7-20 min) when compared to the literature reports (1-40 h).
- Rodrigues-Santos, Cláudio E.,Echevarria, Aurea
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p. 4505 - 4508
(2008/02/03)
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- ISOQUINOLINE AMINOPYRAZOLE DERIVATIVES, THEIR MANUFACTURE AND USE AS PHARMACEUTICAL AGENTS FOR THE TREATMENT OF CANCER
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Objects of the present invention are the compounds of formula (I) their pharmaceutically acceptable salts, enantiomeric forms, diastereoisomers and racemates, the preparation of the above-mentioned compounds, medicaments containing them and their manufacture, as well as the use of the above-mentioned compounds in the control or prevention of illnesses such as cancer.
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Page/Page column 246
(2008/06/13)
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- Degradation of neohesperidin dihydrochalcone by human intestinal bacteria
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The degradation of neohesperidin dihydrochalcone by human intestinal microbiota was studied in vitro. Human fecal slurries converted neohesperidin dihydrochalcone anoxically to 3-(3-hydroxy-4-methoxyphenyl)propionic acid or 3-(3,4-dihydroxyphenyl)propionic acid. Two transient intermediates were identified as hesperetin dihydrochalcone 4′-β-D-glucoside and hesperetin dihydrochalcone. These metabolites suggest that neohesperidin dihydrochalcone is first deglycosylated to hesperetin dihydrochalcone 4′-β-D-glucoside and subsequently to the aglycon hesperetin dihydrochalcone. The latter is hydrolyzed to the corresponding 3-(3-hydroxy-4-methoxyphenyl)propionic acid and probably phloroglucinol. Eubacterium ramulus and Clostridium orbiscindens were not capable of converting neohesperidin dihydrochalcone. However, hesperetin dihydrochalcone 4′-β-D-glucoside was converted by E. ramulus to hesperetin dihydrochalcone and further to 3-(3-hydroxy-4-methoxyphenyl)propionic acid, but not by C. orbiscindens. In contrast, hesperetin dihydrochalcone was cleaved to 3-(3-hydroxy-4-methoxyphenyl)propionic acid by both species. The latter reaction was shown to be catalyzed by the phloretin hydrolase from E. ramulus.
- Braune, Annett,Engst, Wolfram,Blaut, Michael
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p. 1782 - 1790
(2007/10/03)
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- Very short and efficient syntheses of the spermine alkaloid kukoamine A and analogs using isolable succinimidyl cinnamates
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Direct selective acylation of the primary amino functions of spermine and spermidine with a variety of isolable succinimidyl cinnamates, followed by catalytic hydrogenation, gave high yields of the spermine alkaloid kukoamine A and analogs suitable for structure-activity relationship studies. Suitable succinimidyl cinnamates were readily obtained through Wittig reaction of aromatic aldehydes with the ylides Ph3P=CRCO2Me, followed by saponification and activation with N-hydroxysuccinimide in the presence of N,N'-dicyclohexylcarbodiimide. Copyright
- Garnelis, Thomas,Athanassopoulos, Constantinos M.,Papaioannou, Dionissios,Eggleston, Ian M.,Fairlamb, Alan H.
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p. 264 - 265
(2007/10/03)
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- Macrocyclic polyamine lactam synthesis by diphenyl ether closure of 23-, 24- And 28-membered rings
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Novel 23-, 24- and 28-membered cyclic polyamine amides (cinnamamides) have been prepared by closure of diphenyl ethers; functionalized conjugates of spermidine and spermine underwent intramolecular aromatic nucleophilic substitution to afford nitro-substituted analogues of cadabicine class (24-membered polyamine lactam) alkaloids.
- Carrington, Simon,Fairlamb, Alan H.,Blagbrough, Lan S.
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p. 2335 - 2336
(2007/10/03)
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- Spectromagnetic investigation of the active species in the oxidation of propenoidic phenols catalysed by [N,N′-bis(salicylidene)-ethane-1,2-diaminato]cobalt(II)
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The oxidation of propenoidic phenols by molecular oxygen, catalysed by [N,N′-bis(salicylidene)ethane-1,2-diaminato]cobalt(II) [Co(salen)], was studied in different solvents and for variously substituted phenols to find processes alternative to those reported for the removal of polyphenols from waste waters in the paper industry. The reaction of methyl E-4-hydroxy-3-methoxycinnamate (E-methyl ferulate) selectively gave the corresponding 4-hydroxybenzoic acid and 4-hydroxybenzaldehyde; yields are highest in chloroform, good in methanol and very low in pyridine. Conversion was high with E-methyl ferulate, lower with methyl E-4-hydroxycinnamate, while the other phenols, methyl E-3-hydroxy-4-methoxycinnamate (E-methyl isoferulate) and methyl E-3-chloro-4-hydroxycinnamate, did not react. An EPR investigation of the reaction mixtures, performed on samples taken at different reaction times, demonstrated that the most probable mechanism involves reactions (i)-(iii). The [CoII(salen)] + ROH + O2 ? [CoIII(salen)(ROH)(O2)]- (i) [CoIII(salen)(ROH)(O2)- + ROH ?[CoIII(salen)(ROH)(RO?)] + HO2- (ii) [CoIII(salen)(ROH)(RO?)] + HO2- = [CoIII(salen)(RO-)(RO?)] + H2O2 (iii) superoxocobalt radical, [CoIII(salen)(ROH)(O2)]-, and the phenoxy cobalt radical, [CoIII(salen)(RO-)(RO?)], are the EPR-active species; RO? is suggested easily to dissociate from [CoIII(salen)(RO-)(RO?)] and, reacting with O2 at the β-carbon of the allyl substituent, probably gives a dioxethane. This decomposes to aldehyde and acid. The phenol electron-donor properties promote the formation of the superoxocobalt derivative and consequently favour the formation of the phenoxy cobalt radical; a too high stability of this radical does not favour its evolution into oxidation products.
- Bolzacchini, Ezio,Canevali, Carmen,Morazzoni, Franca,Orlandi, Marco,Rindone, Bruno,Scotti, Roberto
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p. 4695 - 4699
(2007/10/03)
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- An Ullmann ether reaction involving an alkynyl substrate: A convergent route to a combretastatin intermediate
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We found that we could employ a disubstituted alkynyl halide in an Ullmann ether reaction to produce the cis-alkene intermediate 3 of the combretastatin natural products.
- Blase,Banerjee
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p. 3187 - 3197
(2007/10/02)
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- A Formal Total Synthesis of the ACE Inhibitor K-13. An Application of Arene-Ruthenium Chemistry to Complex Chemical Synthesis
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Stoichiometric ruthenium activation of 4-chlorophenylalanine derivatives toward nucleophilic substitution, using phenoxide nucleophiles that are derived from protected dipeptides, allowed the formation of isodityrosine derivatives that are synthetic precursors to the ACE inhibitor K-13.An evaluation of carboxyl blocking groups revealed that a 2-bromoethyl ester is the most useful in terms of its compatibility with ruthenium complexation and subsequent nucleophile addition but that its removal is problematic.Conversion to iodoethyl ester using Finkelstein reaction conditions, in the presence of the peptide and amino acid functionality, provided a solution to this problem, since the iodoethyl group was easily removed on treatment with samarium diiodide.
- Pearson, Anthony J.,Lee, Kieseung
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p. 2304 - 2313
(2007/10/02)
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- Structural Analysis of Eukovoside, A New Phenylpropanoid Glycoside from Euphrasia rostkoviana HAYNE
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The isolation and structure determination of a phenylpropanoid glycoside from Euphrasia rostkoviana HAYNE, named eukovoside (1), are reported.
- Sticher, Otto,Salama, Osama,Chaudhuri, Ratan K.,Winkler, Tammo
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p. 1538 - 1542
(2007/10/02)
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