- Photo-degradation of trans-caffeic acid in aqueous solution and influence of complexation by metal ions
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The photo-degradation of metal complexes of caffeic acid was compared to the photo-degradation of free caffeic acid by using UV-vis spectroscopy and HPLC-ESI-mass spectrometry. This article reports first the determination of the products that are formed from the photo-degradation of trans-caffeic acid in aqueous solution and the investigation of the mechanism by a kinetic approach. The good fit between the model and the experimental concentration profiles confirms the photo-isomerization route of the molecule to cis-caffeic acid which then undergoes a cyclization to form the esculetin photo-product. In addition, it reveals, for the first time, another route of major importance leading to the product vinylcatechol. The presence of oxygen leads to an increase of the photo-isomerization rate. Then we report that metallic cations such as Al(III), Pb(II) and Cu(II) can influence the rate and mechanism of caffeic acid photodegradation. Al(III) ions slow down the photo-degradation whereas Pb(II) and Cu(II) ions have a promoter effect on the production of esculetin. In all cases, the photo-isomerization is reduced by the presence of metal ions and the formation of vinylcatechol does not occur.
- Le Person, Anna?g,Lacoste, Anne-Sophie,Cornard, Jean-Paul
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- Colorimetric and fluorescence signalling of thioesculetin in presence of oxidising agent
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Abstract: Thioesculetin (TE) is a sulfur analogue of esculetin. The UV-Vis absorption maximum of TE at 470 nm shifted to 357 nm in the presence of oxidising agent such as m-chloroperoxy benzoic acid (m-CPBA). With gradual increase in the m-CPBA concentrat
- Shinde, Rupali G.,Khan, Ayesha A.,Barik, Atanu
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- Synthesis and evaluation of substituted 8,8-dimethyl-8H-pyrano[2,3-f]chromen-2-one derivatives as vasorelaxing agents
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A series of substituted 8,8-dimethyl-8H-pyrano[2,3-f]chromen-2-ones (chromeno-coumarin hybrids) was synthesized from scopoletin (11) as vasorelaxing agents. The synthesized compounds 21a-f, 22, 23a-e and scopoletin (11) were evaluated for vasorelaxation in endothelium intact rat main mesenteric artery (MMA). Compounds 11, 21a, 21c-f and 22 showed significant vasorelaxation in precontracted MMA within the range of EC50 value 1.58–5.02 μM. These derivatives presented 29.40–70.89 fold increased sensitivity for experimental tissue compared to scopoletin (11), the parent molecule. Among others, 22 was found to be the most active compound which had EC50 1.58 μM with 70.89 fold increased sensitivity. The mechanistic evaluation of 22 showed that it exerted vasorelaxation through Ca2+-activated K+ (BKca) channel and the effect was endothelium-independent.
- Singh, Sarita,Agarwal, Karishma,Iqbal, Hina,Yadav, Pankaj,Yadav, Deepika,Chanda, Debabrata,Tandon, Sudeep,Khan, Feroz,Gupta, Anil Kumar,Gupta, Atul
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- Study of umbelliferone hydroxylation to esculetin catalyzed by polyphenol oxidase
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We characterize umbelliferone, a derivative of 2,4-dihydroxycoumaric acid, as a substrate of polyphenol oxidase. This enzyme hydroxylates umbelliferone to esculetin, its o-diphenol, and then oxidizes it to o-quinone. The findings show that umbelliferone, an intermediate in one of the coumarin biosynthesis pathways, may be transformed into its o-diphenol, esculetin, which is also an intermediate in the same pathway. The activity of the enzyme on umbelliferone was followed by measuring the consumption of oxygen, spectrophotometrically and by HPLC. Kinetic constants characterizing the hydroxylation process were: k cat=0.09±0.02 s-1 and Km=0.17±0. 06 mm. The o-diphenol, esculetin, was a better substrate and when its oxidation was followed spectrophotometrically, the kinetic constants were: k cat=1.31±0.25 s-1 and Km=0.035±0. 002 mM. Both compounds therefore can be considered as alternative substrates to l-tyrosine and l-3,4-dihydroxyphenylalanine (l-DOPA), since both indirectly inhibit melanogenesis.
- Garcia-Molina, Sea,Munoz-Munoz, Joseph Louis,Garcia-Molina, Francis,Rodriguez-Lopez, Joseph Neptune,Garcia-Canovas, Francis
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- Structure-Activity Relationship Study of Hydroxycoumarins and Mushroom Tyrosinase
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The structure-activity relationships of four hydroxycoumarins, two with the hydroxyl group on the aromatic ring of the molecule and two with the hydroxyl group replacing hydrogen of the pyrone ring, and their interactions with mushroom tyrosinase were studied. These compounds displayed different behaviors upon action of the enzyme. The two compounds, ar-hydroxylated 6-hydroxycoumarin and 7-hydroxycoumarin, were both weak substrates of the enzyme. Interestingly, in both cases, the product of the catalysis was the 6,7-hydroxycoumarin, although 5,6- and 7,8-isomers could also theoretically be formed. Additionally, both were able to reduce the formation of dopachrome when tyrosinase acted on its typical substrate, l-tyrosine. Although none of the compounds that contained a hydroxyl group on the pyrone ring were substrates of tyrosinase, the 3-hydroxycoumarin was a potent inhibitor of the enzyme, and the 4-hydroxycoumarin was not an inhibitor. These results were compared with those obtained by in silico molecular docking predictions to obtain potentially useful information for the synthesis of new coumarin-based inhibitors that resemble the structure of the 3-hydroxycoumarin.
- Asthana, Shailendra,Zucca, Paolo,Vargiu, Attilio V.,Sanjust, Enrico,Ruggerone, Paolo,Rescigno, Antonio
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- Study of the Oxidative Cleavage Proposed in the Biogenesis of Transtaganolides/Basiliolides: Pyran-2-one Aromaticity-Mediated Regioselective Control and Biogenetic Implications
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The synthetic feasibility of the oxidative cleavage: epoxidation of 7-O-geranylscopoletin followed by electrocyclic ring-opening, proposed in the biogenesis of transtaganolides/basiliolides is studied. Unlike the proposed pericyclic reactions, this pathway has not yet been addressed. Three synthetic strategies have been tested consisting of: i) Baeyer–Villiger oxidation of p-quinoids, ii) hydrolysis of quinone monoketals, or iii) direct fragmentation by using oxygen donors. Oxidation of the benzene ring of hydroxylated coumarins has been achieved using peroxyacids, but cleavage took place between undesired positions. The aromaticity conservation of the pyran-2-one cycle during oxidation is the controlling factor of these observed regioselectivities. The use of a 4,5-dihydroxy-2-methoxycinnamate model, in which the pyran-2-one ring does not exert influence on oxidation, has allowed the design of a synthetic sequence toward an analogue of the natural pyran-2-one isolated from Thapsia transtagana, key in the biogenesis. Mechanistic proposals for the obtained results as well as their biogenetic implications are raised.
- álvarez, José María,Jorge, Zacarías D.,Massanet, Guillermo M.
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supporting information
(2020/03/05)
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- Anchimerically Assisted Selective Cleavage of Acid-Labile Aryl Alkyl Ethers by Aluminum Triiodide and N, N-Dimethylformamide Dimethyl Acetal
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Aluminum triiodide is harnessed by N,N-dimethylformamide dimethyl acetal (DMF-DMA) for the selective cleavage of ethers via neighboring group participation. Various acid-labile functional groups, including carboxylate, allyl, tert-butyldimethylsilyl (TBS), and tert-butoxycarbonyl (Boc), suffer the conditions intact. The method offers an efficient approach to cleaving catechol monoalkyl ethers and to uncovering phenols from acetal-type protecting groups such as methoxymethyl (MOM), methoxyethoxymethyl (MEM), and tetrahydropyranyl (THP) chemoselectively.
- Sang, Dayong,Yue, Huaxin,Zhao, Zhengdong,Yang, Pengtao,Tian, Juan
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p. 6429 - 6440
(2020/07/14)
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- Regioselective IBX-Mediated Synthesis of Coumarin Derivatives with Antioxidant and Anti-influenza Activities
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Different catechol and pyrogallol derivatives have been synthesized by oxidation of coumarins with 2-iodoxybenzoic acid (IBX) in DMSO at 25 °C. A high regioselectivity was observed in accordance with the stability order of the incipient carbocation or radical benzylic-like intermediate. The oxidation was also effective in water under heterogeneous conditions by using IBX supported on polystyrene. The new derivatives showed improved antioxidant effects in the DPPH test and inhibitory activity against the influenza A/PR8/H1N1 virus. These data represent a new entry for highly oxidized coumarins showing an antiviral activity possibly based on the control of the intracellular redox value.
- Bizzarri, Bruno M.,Botta, Lorenzo,Capecchi, Eliana,Celestino, Ignacio,Checconi, Paola,Palamara, Anna T.,Nencioni, Lucia,Saladino, Raffaele
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p. 3247 - 3254
(2018/01/02)
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- Gastroprotective activity of synthetic coumarins: Role of endogenous prostaglandins, nitric oxide, non-protein sulfhydryls and vanilloid receptors
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Natural or synthetic coumarins showed gastroprotective and antiulcer activity in animal models. In this study, we have synthetized twenty coumarins using classic methods to evaluate their gastroprotective effects on the ethanol/HCl-induced gastric lesion model in mice at 20?mg/kg. Among the coumarins synthetized, compounds 6 and 10 showed the greatest gastroprotective activity being as active as lansoprazole at 20?mg/kg and reducing gastric lesions by 75 and 76%, respectively. Then, in a second experiment, compounds 6 and 10 were re-evaluated in order to understand the possible mode of gastroprotective activity. Regarding coumarin 6, the protective effect was reduced by pre-treatment of the mice with N-ethylmaleimide and l-NAME suggesting that sulfhydryl compounds and endogenous nitric oxide are involved in its gastroprotective activity. While for coumarin 10 the effect was reduced by pre-treatment with indomethacin suggesting that prostaglandins are positively involved in its gastroprotective activity.
- Sepulveda, Beatriz,Quispe, Cristina,Simirgiotis, Mario,Torres-Benítez, Alfredo,Reyes-Ortíz, Johanna,Areche, Carlos,García-Beltrán, Olimpo
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p. 5732 - 5735
(2016/11/25)
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- METHOD OF PRODUCING COMPOUND HAVING DECREASED SUGAR FROM GLYCOSIDE, EXTRACT, AND PHARMACEUTICAL AND FOOD COMPOSITIONS INCLUDING THE COMPOUND
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Provided are a method of producing a compound in which a sugar of a glycoside is reduced or removed, and an extract, a pharmaceutical composition, and a food composition including the compound.
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Paragraph 52-55
(2015/01/07)
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- Biomimetic synthesis of santalin a,b and santarubin a,b, the major colorants of red sandalwood
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Better late than never! Almost 200 years after Pelletier's pioneering studies on the chemical constituents of red sandalwood, the major santalins and santarubins have been synthesized. This efficient approach integrates a Knochel isoflavonoid synthesis with Friedel-Crafts allylations or olefin metatheses, and a final biomimetic reaction cascade that furnishes the venerable benzoxanthenone dyes in a single operation (see scheme). Copyright
- Strych, Sebastian,Trauner, Dirk
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supporting information
p. 9509 - 9512
(2013/09/23)
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- Purification and characterization of a naringinase from Aspergillus aculeatus JMUdb058
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A naringinase from Aspergillus aculeatus JMUdb058 was purified, identified, and characterized. This naringinase had a molecular mass (MW) of 348 kDa and contained four subunits with MWs of 100, 95, 84, and 69 kDa. Mass spectrometric analysis revealed that the three larger subunits were β-d-glucosidases and that the smallest subunit was an α-l-rhamnosidase. The naringinase and its α-l-rhamnosidase and β-d-glucosidase subunits all had optimal activities at approximately pH 4 and 50 C, and they were stable between pH 3 and 6 and below 50 C. This naringinase was able to hydrolyze naringin, aesculin, and some other glycosides. The enzyme complex had a Km value of 0.11 mM and a kcat/Km ratio of 14 034 s-1 mM -1 for total naringinase. Its α-l-rhamnosidase and β-d-glucosidase subunits had Km values of 0.23 and 0.53 mM, respectively, and kcat/Km ratios of 14 146 and 7733 s -1 mM-1, respectively. These results provide in-depth insight into the structure of the naringinase complex and the hydrolyses of naringin and other glycosides.
- Chen, Yuelong,Ni, Hui,Chen, Feng,Cai, Huinong,Li, Lijun,Su, Wenjin
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p. 931 - 938
(2013/08/24)
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- A glucose-tolerant β-glucosidase from Prunus domestica seeds: Purification and characterization
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A glucose-tolerant β-glucosidase was purified to homogeneity from prune (Prunus domestica) seeds by successive ammonium sulfate precipitation, hydrophobic interaction chromatography and anion-exchange chromatography. The molecular mass of the enzyme was estimated to be 61 kDa by SDS-PAGE and 54 kDa by gel permeation chromatography. The enzyme has a pI of 5.0 by isoelectric focusing and an optimum activity at pH 5.5 and 55 °C. It is stable at temperatures up to 45 °C and in a broad pH range. Its activity was completely inhibited by 5 mM of Ag+ and Hg2+. The enzyme hydrolyzed both p-nitrophenyl β-d-glucopyranoside with a Km of 3.09 mM and a Vmax of 122.1 μmol/min mg and p-nitrophenyl β-d-fucopyranoside with a Km of 1.65 mM and a Vmax of 217.6 μmol/min mg, while cellobiose was not a substrate. Glucono-δ-lactone and glucose competitively inhibited the enzyme with Ki values of 0.033 and 468 mM, respectively.
- Chen, Lei,Li, Ning,Zong, Min-Hua
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experimental part
p. 127 - 132
(2012/06/29)
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- Hydroxycoumarin derivatives: Novel and potent α-glucosidase inhibitors
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A novel class of hydroxycoumarin derivatives were found to be potent α-glucosidase inhibitors. Their syntheses were reported and the structure-activity relationship was established. Kinetic enzymatic assays indicated that compound 10 was a slow-binding and noncompetitive inhibitor with a Ki value of 589 nM, while compound 11 was a competitive inhibitor with a Ki value of 4.810 μM. Among all hydroxycoumarin derivatives studied, compounds 10 and 11 exhibited the highest activities, were specific inhibitors of α-glucosidase, and could be exploited as the lead compounds for the development of potent α-glucosidase inhibitors. Compounds 10 and 11 were also selected for further discussion for the mechanism of enzymatic inhibition.
- Shen, Qiong,Shao, Jialiang,Peng, Quan,Zhang, Wanjin,Ma, Lin,Chan, Albert S. C.,Gu, Lianquan
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supporting information; experimental part
p. 8252 - 8259
(2011/02/23)
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- Hydrolysis of toxic natural glucosides catalyzed by cyclodextrin dicyanohydrins
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The hydrolysis of toxic 7-hydroxycoumarin glucosides and other aryl and alkyl glucosides, catalyzed by modified α- and β-cyclodextrin dicyanohydrins, was investigated using different UV, redox, or HPAEC detection assays. The catalyzed reactions all followed Michaelis-Menten kinetics, and an impressive rate increase of up to 7569 (kcat/kuncat) was found for the hydroxycoumarin glucoside substrate 4-MUGP. Good and moderate degrees of catalysis (kcat/kuncat) of up to 1259 were found for the natural glucosides phloridzin and skimmin. By using a newly developed catechol detection UV-assay, a weak degree of catalysis was also found for the toxic hydroxycoumarin esculin. A novel synthesized diaminomethyl β-cyclodextrin showed a weak catalysis of p-nitrophenyl β-D-glucopyranoside hydrolysis. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Bjerre, Jeannette,Nielsen, Erik Holm,Bols, Mikael
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p. 745 - 752
(2008/09/17)
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- Regioselective glucosylation of aromatic compounds: Screening of a recombinant glycosyltransferase library to identify biocatalysts
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(Chemical Equation Presented) A novel whole-cell screen for the identification of new glucosyltransferase (GT) biocatalysts within a recombinant enzyme library was developed. Following biotransformation, levels of D-glucose were used as a measure of biocatalysis. Twenty five enzymes that transfer D-glucose to trans-resveratrol were identified that have the regioselectivity shown in the picture.
- Weis, Markus,Lim, Eng-Kiat,Bruce, Neil,Bowles, Dianna
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p. 3534 - 3538
(2007/10/03)
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- PROCESS FOR PREPARATION OF ESCULETIN COMPOUNDS, ESCULETIN COMPOUNDS AND INTERMEDIATES THEREOF, AND USE OF BOTH
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An esculetin compound, an intermediate thereof, a process for manufacturing an esculetin compound, and an antifungal composition for agriculture and horticulture and an herbicide comprising an esculetin compound or an intermediate thereof are provided. The process for manufacturing an esculetin compound is a low-cost, high-yield, and industrially practicable process, and comprises the following step.A process for manufacturing an esculetin compound of the formula (2): characterized by cyclizing a trihydroxybenzaldehyde compound of the formula (1): in an aprotic polar solvent in the presence of a weak base, with acetic anhydride or the like.
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Page/Page column 12-13
(2010/01/31)
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- Partial purification and characterization of a soybean β-glucosidase with high specific activity towards isoflavone conjugates
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A β-glucosidase with high specific activity towards isoflavone conjugates was purified from soybean [Glycine max] roots by high salt extraction from a low speed centrifugal pellet and subsequent anion and cation exchange chromatography. Purification required stabilization throughout fractionation in 10% glycerol. The enzyme is most likely a dimer (approximate Mr 165 kDa) with potential subunits of Mr 80 and/or 75 kDa. The pH and temperature optima are pH 6 and 30 °C, respectively. The enzyme was highly heat-stable. Of the various potential effectors examined, silver and mercury ions were the most inhibitory. The IC50 of silver ions was increased from 140 μM to 14 mM in the presence of 250 μM β-mercaptoethanol. Glucono-δ-lactone was not strongly inhibitory (IC50 24 mM). The activity was highly active against isoflavone conjugates, with a specificity constant 160-1000 fold higher for isoflavone conjugates over the generic chromogenic substrate, p-nitrophenyl β-glucoside. The enzyme was inactive against the flavonol glycosides tested. The partially purified enzyme had similar Km and kcat towards 7-O-glucosyl- and 7-O-glucosyl-6″-malonyl-isoflavones, suggesting that it may be able to cleave the esterified glucosyl conjugate. We hypothesize that the enzyme is involved in the release of daidzein and genistein, both of which play central roles in soybean defense.
- Hsieh, Ming-Ching,Graham, Terrence L
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p. 995 - 1005
(2007/10/03)
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- Improved Synthesis of Esculetin
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An improved synthesis of esculetin (6,7-dihydroxycoumarin) and 3-hydroxy-6,7-dimethoxycoumarin (4a) is described.
- Jackson, Yvette A.
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p. 1979 - 1986
(2007/10/02)
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- Increasing 5-lipoxygenase inhibitory activities by oxidative conversion of o-methoxyphenols to catechols using a Cu2+ - ascorbic acid - O2 system
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Several complicated o-methoxyphenols were oxidized with high selectivity to catechols by a Cu2+ - ascorbic acid - O2 system. In this way, the RBL-1 5-lipoxygenase inhibitory activities of o-methoxyphenols were greatly increased. [6]-Norgingerol (4), a novel compound derived from [6]-gingerol (3), shows promise as a lead compound for new drugs because of its high inhibitory potency (IC50 = 5.0 x 10-8 M).
- Aihara,Higuchi,Hirobe
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p. 842 - 844
(2007/10/02)
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- Synthesis and Structural Elucidation of Coumarinolignans
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Coumarinolignans are a relatively new class of natural products combining a coumarin skeleton with a phenylpropene moiety.We describe here details of the first biomimetic syntheses of compounds in this series (1-16) utilizing both chemical and enzymatic approaches and the application of the selective INEPT nmr technique for unambiguous structure assignment.Chemical oxidation using silver oxide as an oxidizing agent typically produced two regioisomeric trans-substituted coumarinolignans.Enzymatic oxidation on the other hand normally gave rise to a single regioisomer.Almost all of the known natural coumarinolignans and several new compounds which may subsequently be obtained as natural products were synthesized.Three nmr strategies are described for the structure elucidation of the coumarinolignans, but only one of these techniques, the selective INEPT method, affords an unambiguous structure when only one regioisomer is present.Using this technique the structures and complete proton and carbon-13 chemical shift assignments of sixteen synthetic coumarinolignans were established.The described nmr strategy should prove useful for the unambiguous structure determination of all natural 2-aryl benzodioxanes, including the flavonolignans, the xanthonolignans and certain neolignans.
- Lin, Lee-Juian,Cordell, Geoffrey A.
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p. 3052 - 3080
(2007/10/02)
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- Characterization of a Product (Esculetin; 6,7-Dihydroxycoumarin) from the Phenolase-Caffeic Acid Reaction System
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Esculetin (6,7-dihydroxycoumarin) was isoleted in crystalline form from a reaction mixture containing phenolase and cis-caffeic acid.The oxygen atom in the lactone ring of esculetin thus formed was not derived from molecular oxigen or water, and it is suggested that the carboxyl group of caffeic acid may be involved.Keywords - phenolase (tyrosinase, polyphenol oxidase); caffeic acid; esculetin; coumarin
- Sato, Mitsuhiko,Hiraoka, Atsushi
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p. 1289 - 1292
(2007/10/02)
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- One-Electron Redox Potentials of Phenols. Hydroxy- and Aminophenols and Related Compounds of Biological Interest
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The rate constants for reversible electron transfer between a series of substituted phenolate ions and anilines and various substituted phenoxyl or anilino radicals in aqueous solution were measured by observing the formation or depletion of the radicals involved.Nonequilibrium concentrations of the radicals were produced in the presence of the corresponding phenols or anilines by using the pulse radiolysis technique.The relaxation of the system to equilibrium was monitored by optical detection methods.From the equilibrium constants for one-electron transfer, the one-electron redox potentials (E2) for 38 phenolic or anilino type compounds were determined, many of which are natural products.The redox potentials are strongly influenced by electron-donating or -withdrawing substituents at the aromatic system.
- Steenken, S.,Neta, P.
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p. 3661 - 3667
(2007/10/02)
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- Complexes of Cu(II) with Some Biologically Active Dihydroxycoumarins
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Complexes of Cu(II) with hydroxycoumarins, viz. esculetin, daphnetin and their 4-methyl and 4-phenyl derivatives have been prepared.The general composition of the complexes is .The water molecules are replaced on reaction with pyridine or ammonia to give complexes of the type (where X = NH3 or C5H5N).IR studies show that more acidic of the two phenolic hydroxyl groups present at C-7 in the ligand is involved in complexation in the parent complexes.Thermal studies on the parent complexes indicate the formation of two intermediate compounds which correspond to the compositions and but only one intermediate, , is formed on heating the pyridine or ammonia adducts.
- Singh, H. B.,Negi, R. K.,Srivastava, Smita
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p. 1026 - 1028
(2007/10/02)
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- 2-Acyl-5-substituted thiatetrahydrofuran-4-ones
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Described are 2-acyl-5-substituted thiatetrahydrofuran-4-ones having the generic structure: STR1 wherein R1, R2, R1 ' and R2 ' are the same or different and each represents hydrogen or methyl and wherein R3 represents one of C1 -C9 alkyl, benzyl, phenyl, substituted or unsubstituted allyl having the structure: STR2 substituted or unsubstituted 3-furyl having the structure: (wherein R4 and R8 are the same or different and each represents hydrogen or methyl) hydroxy alkyl, oxoalkyl, hydroxycycloalkyl or oxocycloalkyl having the structure: STR3 (wherein R5 and R6, taken separately, represent hydrogen or C1 -C3 alkyl or R5 and R6, taken together, complete a cycloalkyl group and wherein Q is one of the moieties: STR4 The 2-acyl-5-substituted thiatetrahydrofuran-4-ones of our invention have organoleptic properties which make them useful for augmenting or enhancing the aroma or flavor of foodstuffs, tobaccos and the aroma of perfumes and perfumed articles.
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- Process for preparing 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-[2H]furanones
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Described is a process for preparing 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-[2H]furanones by reacting one or more dimers of a C4 -C6 alpha, beta alkanedione with furfurylmercaptan to form one or more 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-[2H]furanones, said reaction taking place in an acidic medium and in the presence of an inert solvent. The processes of this invention give rise to compounds which can be used in flavor and aroma imparting, augmenting, modifying or enhancing compositions for foodstuffs, chewing gums, toothpastes, medicinal products and tobaccos and as foodstuff, chewing gum, toothpaste, medicinal product and tobacco aroma and flavor imparting, augmenting, enhancing or modifying materials.
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