- Ladroside (=6'-Caffeoyl-mussaenoside), a New Iridoid Glucoside from Veronica officinalis L. (Scrophulariaceae) and the Elucidation of the Absolute Configuration at C(8) of Mussaenoside
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A new iridoid glucoside, named ladroside, together with mussaenoside (1) , has been isolated from Veronica officialis L.The structure of ladroside (4) and the identity of mussaenoside have been established by spectral analysis.Additionally, the absolute configuration at C(8) carrying hydroxyl group has been established by chemical evidence.
- Affifi-Yazar, Fatma Ue.,Sticher, Otto,Uesato, Shinichi,Nagajima, Kimiko,Inouye, Hiroyuki
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- A New Glycoside, Kusaginin Isolated from Clerodendron trichotomum
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A new glycoside, kusaginin was isolated from Clerodendron trichotomum Thunb. and 2-(3,4-dihydroxyphenyl)ethyl 3-O-α-L-rhamnopyranosyl-4-O-(3,4-dihydroxycinnamoyl)-β-D-glucopyranoside was assigned to this substance from studies on the hydrolysis products and from analyses of the 1H NMR and 13C NMR spectra.
- Sakurai, Atsushi,Kato, Takahiko
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- MALONATED FLAVONOL GLYCOSIDES AND 3,5-DICAFFEOYLQUINIC ACID FROM PEARS
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Key Word Index--Pyrus communis; Rosaceae; pears; malonated flavonol glucosides; 3,5-dicaffeoylquinic acid.Abstract--3-O-(6''-O-malonyl)-β-Glucosides of quercetin, kaempferol, isorhamnetin and 3,5-dicaffeoylquinic acid were isolated and identified from leaves of pears.The compounds are also present in the fruits.
- Wald, Burkard,Wray, Victor,Galensa, Rudolf,Herrmann, Karl
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- Two new monoterpenes and one dicaffeic acid ester from Sibiraea angustata with hypolipidemic activities in HepG2 cells in Vitro
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Two new monoterpenes, named sibiscolacton B (1) and sibiscolacton C (2), together with a sorbate obtained from the natural product 1, 6-sorbitol-O-dicaffeic acid ester (3), were isolated from an aqueous extract of the aerial portion of Sibiraea angustata. The compounds' structures were elucidated on the basis of extensive spectroscopic analysis, as well as literature comparisons. A preliminary in vitro bioassay showed that all of the compounds exhibited hypolipidemic effects in HepG2 cells.
- Li, Bin,Chen, Xiaotian,Wang, Zhangwei,Liu, Hongdong,Liu, Bo,Yu, Shishan,Lai, Xuewen,Xu, Xianghong,Hayashi, Toshimitsu
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- Rhamnetin Glycosides from the Genus Spiraea
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Rhamnetin (7-O-methylquercetin,1) and its glycosides were found for the first time in the genus Spiraea (Rosaceae) during chromatographic studies of representatives from the subgenus Protospiraea. Leaves of S. salicifolia yielded1, rhamnetin-3-O-β-D-glucopyranoside (2), and two new flavonoids3and4that were identified by UV, IR, and NMR spectroscopy and mass spectrometry as rhamnetin-3-O-(6″-O-p-coumaroyl)-β-D-glucopyranoside (spiraearhamnin A,3) and rhamnetin-3-O-(6″-O-caffeoyl)-β-D-glucopyranoside (spiraearhamnin B,4). Leaves of S. betulifolia and S. betulifolia var. aemiliana afforded1and2and glycosides of kaempferol, quercetin, and isorhamnetin. Species of the subgenus Metaspiraea (S. alpina, S. chamaedryfolia, S. dahurica, S. hypericifolia, and S. media) did not contain1or its derivatives.
- Olennikov,Chirikova
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- Bioactive constituents from Chinese natural medicines. XXXVI.1) four new acylated phenylethanoid oligoglycosides, kankanosides J1, J2, K1, and K2, from stems of cistanche tubulosa
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Four new acylated phenylethanoid oligoglycosides, kankanosides J 1 (1), J2 (2), K1 (3), and K2 (4), were isolated from stems of Cistanche tubulosa (Orobanchaceae) together with isocampneoside I (5). Their struct
- Pan, Yingni,Morikawa, Toshio,Ninomiya, Kiyofumi,Imura, Katsuya,Yuan, Dan,Yoshikawa, Masayuki,Muraoka, Osamu
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- Analysis of protein-phenolic compound modifications using electrochemistry coupled to mass spectrometry
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In the last decade, electrochemical oxidation coupled with mass spectrometry has been successfully used for the analysis of metabolic studies. The application focused in this study was to investigate the redox potential of different phenolic compounds such as the very prominent chlorogenic acid. Further, EC/ESI-MS was used as preparation technique for analyzing adduct formation between electrochemically oxidized phenolic compounds and food proteins, e.g., alpha-lactalbumin or peptides derived from a tryptic digestion. In the first step of this approach, two reactant solutions are combined and mixed: one contains the solution of the digested protein, and the other contains the phenolic compound of interest, which was, prior to the mixing process, electrochemically transformed to several oxidation products using a boron-doped diamond working electrode. As a result, a Michael-type addition led to covalent binding of the activated phenolic compounds to reactive protein/peptide side chains. In a follow-up approach, the reaction mix was further separated chromatographically and finally detected using ESI-HRMS. Compound-specific, electrochemical oxidation of phenolic acids was performed successfully, and various oxidation and reaction products with proteins/peptides were observed. Further optimization of the reaction (conditions) is required, as well as structural elucidation concerning the final adducts, which can be phenolic compound oligomers, but even more interestingly, quite complex mixtures of proteins and oxidation products.
- Kallinich, Constanze,Schefer, Simone,Rohn, Sascha
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- New thiophene and flavonoid from tagetes minuta leaves growing in saudi arabia
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Phytochemical investigation of the methanolic extract of Tagetes minuta L. (Asteraceae) leaves resulted in the isolation and identification of two new compounds: 5-methyl-2,2',5',2'',5'',2''',5''',2''''-quinquethiophene (1) and quercetagetin-6-O-(6-Ocaffe
- Al-Musayeib, Nawal M.,Mohamed, Gamal A.,Ibrahim, Sabrin R. M.,Ross, Samir A.
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- Antiestrogenic constituents of the Thai medicinal plants Capparis flavicans and Vitex glabrata
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Antiestrogenic compounds were investigated from Thai indigenous plants for galactogogues since estrogen is reported to suppress lactation in breastfeeding women. The aerial parts of the Thai medicinal plant Capparis flavicans, which has traditionally been
- Luecha, Prathan,Umehara, Kaoru,Miyase, Toshio,Noguchi, Hiroshi
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- Cytotoxic triterpenoid saponins from Clematis tangutica
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Eight previously undescribed oleanane-type triterpenoid saponins, clematangoticosides A-H, together with eight known saponins, were isolated from the whole plants of Clematis tangutica (Maxim.) Korsh. Their structures were elucidated by extensive spectroscopic analysis, in combination with chemical methods (acid hydrolysis and mild alkaline hydrolysis). Clematangoticosides D-G were found to be unusual 23, 28-bidesmosidic glycosides. The cytotoxic activities of all of the isolated saponins were evaluated against the four human cancer cell lines SGC-7901, HepG2, HL-60 and U251MG. Clematoside S, sapindoside B, kalopanax saponin A, and koelreuteria saponin A exhibited cytotoxicity against all of the test cancer cell lines with IC50 values in the range of 1.88–27.20?μM, while clematangoticoside D and F showed selective cytotoxicity against SGC-7901 with IC50 values of 24.22 and 21.35?μM, respectively.
- Zhao, Min,Da-Wa, Zhuo-Ma,Guo, Da-Le,Fang, Dong-Mei,Chen, Xiao-Zhen,Xu, Hong-Xi,Gu, Yu-Cheng,Xia, Bing,Chen, Lei,Ding, Li-Sheng,Zhou, Yan
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- Caffeoyl sugar esters and an ellagitannin from Rubus sanctus
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The new natural caffeoyl esters, 3,6-di-O-caffeoyl-(α/β) -glucose and 1-O-caffeoyl-β-xylose, together with the hitherto unknown natural tannin, 2,3-O-hexahydroxydiphenoyl-4,6-O-sanguisorboyl-(α/β)-glucose, have been isolated from the aqueous alcohol aeria
- Hussein, Sahar A.M.,Ayoub, Nahla A.,Nawwar, Mahmoud A.M.
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- A new isoflavone from Blepharis ciliaris of an Egyptian origin
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A phytochemical study of the aerial parts of Blepharis ciliaris (L.) B.L. Burtt. led to the isolation of one new isoflavone glycoside caffeic acid ester: genistein-7-O-(6″-O-E-caffeoyl-β-d-glucopyranoside) (4), along with seven known compounds: methyl veratrate (1), methyl vanillate (2), protocatechuic acid (3), naringenin-7-O-(3″-acetyl-6″-E-p-coumaroyl- β-d-glucopyranoside) (5), naringenin-7-O-(6″-E-p-coumaroyl-β-d- glucopyranoside) (6), apigenin-7-O-(6″-E-p-coumaroyl-β-d- glucopyranoside) (7), and acteoside (8). Their structures were established on the basis of detailed analyses of physical, chemical, and spectral data. Compounds 1, 2, 3, 6, and 8 were isolated for the first time from this plant. The antioxidant activity of the different extracts as well as for some of the isolated compounds was evaluated.
- El-Shanawany, Mohamed A.,Sayed, Hanaa M.,Ibrahim, Sabrin R. M.,Fayed, Marwa A. A.,Radwan, Mohamed M.,Ross, Samir A.
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- Coumarin glucosides from Cruciata taurica
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Two new coumarin glycosides (1 and 2) along with two known coumarin glucosides, daphnin (3) and daphnetin glucoside (4) were isolated from the aerial parts of Cruciata taurica. The structures of the new compounds were elucidated by spectral methods and ch
- De Rosa, Salvatore,Mitova, Maya,Handjieva, Nedjalka,Cals, Ihsan
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- Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa1
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The methanolic extract from fresh stems of Cistanche tubulosa (Orobanchaceae) was found to show hepatoprotective effects against d-galactosamine (d-GalN)/lipopolysaccharide (LPS)-induced liver injury in mice. From the extract, three new phenylethanoid oligoglycosides, kankanosides H1 (1), H2 (2), and I (3), were isolated together with 16 phenylethanoid glycosides (4-19) and two acylated oligosugars (20, 21). The structures of 1-3 were determined on the basis of spectroscopic properties as well as of chemical evidence. Among the isolates, echinacoside (4, IC50 = 10.2 μM), acteoside (5, 4.6 μM), isoacteoside (6, 5.3 μM), 2′-acetylacteoside (8, 4.8 μM), and tubuloside A (10, 8.6 μM) inhibited d-GalN-induced death of hepatocytes. These five isolates, 4 (31.1 μM), 5 (17.8 μM), 6 (22.7 μM), 8 (25.7 μM), and 10 (23.2 μM), and cistantubuloside B1 (11, 21.4 μM) also reduced TNF-α-induced cytotoxicity in L929 cells. Moreover, principal constituents (4-6) exhibited in vivo hepatoprotective effects at doses of 25-100 mg/kg, po.
- Morikawa, Toshio,Pan, Yingni,Ninomiya, Kiyofumi,Imura, Katsuya,Matsuda, Hisashi,Yoshikawa, Masayuki,Yuan, Dan,Muraoka, Osamu
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- Novel bioactive dammarane caffeoyl esters from Celastrus rosthornianus
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Three new dammar-type triterpenoid caffeates (1-3) were isolated from the stalks of Celastrus rosthornianus Loes. Their structures were established through various spectral studies as 3β,20(S),24(S)-trihydroxyldammar-25-ene 3-caffeate (1), 3β,20(S),24(R)-trihydroxyldammar-25-ene 3-caffeate (2) and 3β,20(S),25-trihydroxyldammar-23(Z)-ene 3-caffeate (3), respectively. The three new compounds (1-3) showed strong antitumor activity against the human cervical squamous carcinoma cell line with IC50 values of 6.4, 5.3 and 6.5 μg/mL, respectively. The biological analyses of 1-3 and their hydrolysates 1a-3a indicated that the caffeoyl group could increase the bioactivity. Georg Thieme Verlag KG Stuttgart.
- Wang, Kui-Wu,Sun, Cui-Rong,Wu, Xiao-Dan,Pan, Yuan-Jiang
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- Three antibacterial compounds from the roots of Pteris multifida
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A new eudesmane-type sesquiterpenoid, 3β-caffeoxyl-1β,8α- dihydroxyeudesm-4(15)-ene (1), together with two known compounds including ludongnin V (2) and isoneorautenol (3), were isolated from the roots of Pteris multifida. Their structures were determined
- Hao-Bin, Hu,Xu-Dong, Zheng,Huai-Sheng, Hu,Hong, Cao
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- Hemiterpene glucosides with anti-platelet aggregation activities from Ilex pubescens
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Two new hemiterpene glucosides named pubescenosides A and B were isolated from the root of Ilex pubescens. Their structures were elucidated on the basis of spectroscopic and chemical evidence as 2-(trans-caffeoyloxy)methyl-3-hydroxy- 1-butene-4-O-β-D-glucopyranoside and 2-hydroxymethyl-3-caffeoyloxy-1- butene-4-O-β-D-glucopyranoside, respectively. Pharmacological investigation on pubescenosides A and B indicated that both possess potent anti-platelet aggregation activities.
- Jiang, Zhi-Hong,Wang, Jing-Rong,Li, Min,Liu, Zhong-Qiu,Chau, Ka-Yee,Zhao, Chi,Liu, Liang
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- A new naphthoquinone and a new neolignan from ligularia vellerea rhizomes
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In the course of phytochemical investigations of Ligularia vellerea rhizomes, a new naphthoquinone, 2,5-dihydroxy-6,7-dimethylnaphthoquinone (1), and a new neolignan, 4-[(3',4'-dihydroxycinnamoyl)-oxy]-methyl cinnamate (2), have been isolated and characterized on the basis of spectroscopic methods (1H NMR, 13C NMR, 2D NMR, and MS).
- Wang,Zhao,Shi,Li,Zhang,Liu
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- Ballodiolic acid a and b: Two new ros, (? oh), (onoo? ) scavenging and potent antimicrobial constituents isolated from ballota pseudodictamnus (l.) benth.
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Bioassays guided phytochemical investigations on the ethyl acetate-soluble fraction of the root material of Ballota pseudodictamnus (L.) Benth. led to the isolation of two new compounds, ballodiolic acid A (1) and ballodiolic acid B (2), along with three known compounds ballodiolic acid (3), ballotenic acid (4), and β-amyrin (5), which were also isolated for the first time from this species by using multiple chromatographic techniques. The structures of the compounds (1–5) were determined by modern spectroscopic analysis including 1D and 2D NMR techniques and chemical studies. In three separate experiments, the isolated compounds (1–5) demonstrated potent antioxidant scavenging activity, with IC50 values ranging from 07.22–34.10 μM in the hydroxyl radical (? OH) inhibitory activity test, 58.10–148.55 μM in the total ROS (reactive oxygen species) inhibitory activity test, and 6.23–69.01 μM in the peroxynitrite (ONOO? ) scavenging activity test. With IC50 values of (07.22 ± 0.03, 58.10 ± 0.07, 6.23 ± 0.04 μM) for? OH, total ROS, and scavenge ONOO?, respectively, ballodiolic acid B (2) showed the highest scavenging ability. Antibacterial and antifungal behaviors were also exposed to the pure compounds 1–5. In contrast to compounds 4 and 5, compounds 1–3 were active against all bacterial strains studied, with a good zone of inhibition proving these as a potent antibacterial agent. Similarly, compared to compounds 3–5, compounds 1 and 2 with a 47 percent and 45 percent respective inhibition zone were found to be more active against tested fungal strains.
- Ahmad, Ijaz,Ahmad, Nisar,Alobaid, Abdulrahman,Amin, Syed Badar,Bari, Ahmed,Fozia,Mahmood, Hafiz Majid,Shaheen, Asmat,Sohaib, Muhammad,Ullah, Riaz
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- Chemical structures of constituents from the whole plant of Bacopa monniera
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Two new dammarane-type triterpene oligoglycosides, bacomosaponins A and B, and three new phenylethanoid glycosides, bacomosides A, B1, and B2, were isolated from the whole plant of Bacopa monniera Wettst. The chemical structures of the new constituents were characterized on the basis of chemical and physicochemical evidence. In the present study, bacomosaponins A and B with acyl groups were obtained from the whole plant of B. monniera. This is the first report of acylated dammarane-type triterpene oligoglycosides isolated from B. monniera. In addition, dammarane-type triterpene saponins significantly inhibited the aggregation of 42-mer amyloid β-protein.
- Ohta, Tomoe,Nakamura, Seikou,Nakashima, Souichi,Oda, Yoshimi,Matsumoto, Takahiro,Fukaya, Masashi,Yano, Mamiko,Yoshikawa, Masayuki,Matsuda, Hisashi
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- Phenylpropanoid glucosides from leaves of Coussarea hydrangeifolia (Rubiaceae)
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Phenylpropanoid glycosides, 1′-O-benzyl-α-l-rhamnopyranosyl- (1″ → 6′)-β-d-glucopyranoside (1) and α-l- xylopyranosyl-(4″ → 2′)-(3-O-β-d-glucopyranosyl)-1′- O-E-caffeoyl-β-d-glucopyranoside (2), together with the known derivatives, 1,6-di-O-caffeoyl-β-d-glucopyranoside (3), 1-O-(E)-caffeoyl-β-d- glucopyranoside (4) and 1-O-(E)-feruloyl-β-d-glucopyranoside (5), were isolated from leaves of Coussarea hydrangeifolia. Their structures were determined by IR, HRESIMS, and 1D and 2D NMR experiments, and their antioxidant activities, evaluated by assaying the free radical scavenging capacity using the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical as substrate. The antioxidant activities of 3 and 4 (IC50 values of 15.0 and 19.2 μM, respectively) were comparable to that of the standard positive control caffeic acid, whilst 2 and 5 were only weakly active and 1 was inactive.
- Hamerski, Lidilhone,Bomm, Mauro Dionei,Silva, Dulce Helena Siqueira,Young, Maria Claudia Marx,Furlan, Maysa,Eberlin, Marcos Nogueira,Castro-Gamboa, Ian,Cavalheiro, Alberto Jose,Da Silva Bolzani, Vanderlan
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- A new caffeoylgluconic acid derivative from the nearly ripe fruits of Evodia rutaecarpa
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A new caffeoylgluconic acid derivative, trans-caffeoyl-6-O-d-gluconic acid methyl ester (1), together with two known compounds named trans-caffeoyl-6-O-d-glucono-γ-lactone (2) and trans-caffeoyl-6-O-d-gluconic acid (3), was isolated from the nearly ripe fruits of Evodia rutaecarpa (Juss.) Benth. These compounds were isolated by various separation methods associated with the UPLC-Q-TOF-MS technique. Their structures were elucidated on the basis of extensive spectroscopic methods.
- He, Ying,Li, Jie,Wu, Hong-Hua,Chai, Xin,Yang, Jing,Wang, Yue-Fei,Zhang, Peng,Zhu, Yan,Gao, Xiu-Mei
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- Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites
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The Fujiwara-Moritani reaction has had a profound contribution in the emergence of contemporary C-H activation protocols. Despite the applicability of the traditional approach in different fields, the associated reactivity and regioselectivity issues had
- Ali, Wajid,Anjana, S. S.,Bhattacharya, Trisha,Chandrashekar, Hediyala B.,Goswami, Nupur,Guin, Srimanta,Maiti, Debabrata,Panda, Sanjib,Prakash, Gaurav,Saha, Argha,Sasmal, Sheuli,Sinha, Soumya Kumar
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supporting information
p. 1929 - 1940
(2022/02/01)
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- Engineered Bacterial Flavin-Dependent Monooxygenases for the Regiospecific Hydroxylation of Polycyclic Phenols
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4-Hydroxyphenylacetate 3-hydroxylase (4HPA3H), a flavin-dependent monooxygenase from E. coli that catalyzes the hydroxylation of monophenols to catechols, was modified by rational redesign to convert also more bulky substrates, especially phenolic natural products like phenylpropanoids, flavones or coumarins. Selected amino acid positions in the binding pocket of 4HPA3H were exchanged with residues from the homologous protein from Pseudomonas aeruginosa, yielding variants with improved conversion of spacious substrates such as the flavonoid naringenin or the alkaloid mimetic 2-hydroxycarbazole. Reactions were followed by an adapted Fe(III)-catechol chromogenic assay selective for the products. Especially substitution of the residue Y301 facilitated modulation of substrate specificity: introduction of nonaromatic but hydrophobic (iso)leucine resulted in the preference of the substrate ferulic acid (having a guaiacyl (guajacyl) moiety, part of the vanilloid motif) over unsubstituted monophenols. The in vivo (whole-cell biocatalysts) and in vitro (three-enzyme cascade) transformations of substrates by 4HPA3H and its optimized variants was strictly regiospecific and proceeded without generation of byproducts.
- Dippe, Martin,Funke, Evelyn,Herrmann, Susann,Pecher, Pascal,Pietzsch, Markus,Wessjohann, Ludger A.
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- A chlorogenic acid esterase from a metagenomic library with unique substrate specificity and its application in caffeic and ferulic acid production from agricultural byproducts
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Soil microbes are an abundant source of enzymes with unique properties that may be useful for industrial applications. As most wild-type strains show low chlorogenic acid esterase expression and activity, and most microbes cannot be cultured in the laboratory, a metagenomic approach provides methods of identifying new enzymes. In this study, a gene encoding a chlorogenic acid esterase, named Tan410, was isolated from a soil metagenomic library and overexpressed in Escherichia coli BL21 (DE3). The recombinant enzyme, with a predicted molecular weight of 54.88 kDa, was purified to homogeneity. The K m and V max values for Tan410 were 1.26 mM and 0.33 mM min–1, respectively, with chlorogenic acid as the substrate. Its optimum temperature and pH for reaction were 30 °C and 7.5, respectively. The enzyme exhibited moderate thermostability and broad pH stability (3.0–10.0). Tan410 was also able to hydrolyse ethyl ferulate, methyl caffeate, propyl gallate, ethyl gallate, methyl vanillate, methyl benzoate, ethyl benzoate, methyl 2,5-dihydroxybenzoate, and methyl 3,5-dihydroxybenzoate, and it released caffeic and ferulic acids from agricultural byproducts (destarched wheat bran and coffee pulp). Tan140 has potential for industrial application in biomass valorization.
- Gui, Lun,Long, Qizhang,Yao, Jian
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- Herbicide based on haloxyfop, flumetsulam and halosulfuron-methyl
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The invention discloses a herbicide based on haloxyfop, flumetsulam and halosulfuron-methyl. The herbicide is prepared from the following raw materials in parts by weight: 1-15 parts of haloxyfop-R-methyl, 1-15 parts of flumetsulam, 1-37 parts of halosulfuron-methyl, 1-2 parts of a modified antioxidant, 10-12 parts of borax, 6-8 parts of a surfactant, 10-12 parts of triethanolamine, 10-12 parts of vegetable oil and 40-42 parts of deionized water. After the haloxyfop-R-methyl, the flumetsulam and the halosulfuron-methyl are mixed, the effects are complementary, the weeding spectrum is wider, the weeding activity is high, the weeding effect is more excellent. In addition, the modified antioxidant is added into the herbicide formula, so that the composite herbicide has the effects of resisting oxidation aging and ultraviolet aging, effective components are prevented from decomposing and losing efficacy in the presence of light, the pesticide effect is kept lasting, and the application prospect and popularization value are remarkably improved.
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Paragraph 0038; 0046; 0053; 0061; 0068; 0076
(2021/06/21)
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- Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation
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A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.
- Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei
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supporting information
p. 5905 - 5908
(2021/06/18)
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- Acylated pelargonidin and cyanidin 3-sambubiosides from the flowers of Aeschynanthus species and cultivars
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Thirteen anthocyanins were isolated from the flowers of two Aeschynanthus species, A. fulgens and A. pulcher, and six cultivars, ‘Mahligai’, ‘Mona Lisa’, ‘SoeKa’, ‘Redona’, ‘Freshya’ and ‘Bravera’, and identified as pelargonidin and cyanidin 3-O-sambubiosides and their malonates, succinates, p-coumarates and caffeates, and pelargonidin 3-O-glucoside by acid hydrolysis, HR-MS and NMR. Of their anthocyanins, pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-malonylglucoside)] (2), pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-succinylglucoside)] (3), pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-E-p-coumaroylglucoside)] (4), pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-Z-p-coumaroylglucoside)] (5), pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-E-caffeoylglucoside)] (6) and cyanidin 3-O-[xylosyl-(1 → 2)-(6''-succinylglucoside)] (9) were reported in nature for the first time.
- Iwashina, Tsukasa,Mizuno, Takayuki,Rahayu, Sri,Sugahara, Kohtaro,Tsutsumi, Chie,Widyatmoko, Didik
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- Anti-inflammatory glycosides from the roots of Paeonia intermedia C. A. Meyer
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Three new phenolic glycosides, intermedia A–C (1–3), one new acyclic alcohol glycoside, intermedia D (4), together with 3 known glycosides (5–7), were isolated from the dried roots of Paeonia intermedia C. A. Meyer. Their structures were established by means of extensive spectroscopic analysis (HRESIMS, NMR). Compound 1 have a rare benzo[1,5]dioxepine skeleton. The bioassay results showed that compound 3 exhibited inhibitory activity against proinflammatory cytokines nitric oxide (NO) secretion in LPS-activated RAW264.7 cells with an IC50 value of 85.76 ± 1.36 μM.
- Yu, Liang,Zhu, Ling-Juan,Wang, An-Hua,Qin, Yu,Zhang, Xue,Jia, Jing-Ming,Yao, Xin-Sheng
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p. 1452 - 1458
(2019/08/30)
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- Optimization of the biosynthesis of b-ring ortho-hydroxy lated flavonoids using the 4-hydroxyphenylacetate 3-hydroxylase complex (Hpabc) of escherichia coli
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Flavonoids are important plant metabolites that exhibit a wide range of physiological and pharmaceutical functions. Because of their wide biological activities, such as anti-inflammatory, antioxidant, antiaging and anticancer, they have been widely used in foods, nutraceutical and pharmaceuticals industries. Here, the hydroxylase complex HpaBC was selected for the efficient in vivo production of ortho-hydroxylated flavonoids. Several HpaBC expression vectors were constructed, and the corresponding products were successfully detected by feeding naringenin to vector-carrying strains. However, when HpaC was linked with an S-Tag on the C terminus, the enzyme activity was significantly affected. The optimal culture conditions were determined, including a substrate concentration of 80 mg·L?1, an induction temperature of 28?C, an M9 medium, and a substrate delay time of 6 h after IPTG induction. Finally, the efficiency of eriodictyol conversion from P2&3-carrying strains fed naringin was up to 57.67 ± 3.36%. The same strategy was used to produce catechin and caf-feic acid, and the highest conversion efficiencies were 35.2 ± 3.14 and 32.93 ± 2.01%, respectively. In this paper, the catalytic activity of HpaBC on dihydrokaempferol and kaempferol was demonstrated for the first time. This study demonstrates a feasible method for efficiently synthesizing in vivo B-ring dihydroxylated flavonoids, such as catechins, flavanols, dihydroflavonols and flavonols, in a bacterial expression system.
- Chen, Yang,Gao, Liping,Gui, Lin,Guo, Lina,Lei, Ting,Li, Yan,Ma, Xiubing,Ruan, Haixiang,Wang, Longji,Wang, Yunsheng,Xia, Tao
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- Thiols Act as Methyl Traps in the Biocatalytic Demethylation of Guaiacol Derivatives
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Demethylating methyl phenyl ethers is challenging, especially when the products are catechol derivatives prone to follow-up reactions. For biocatalytic demethylation, monooxygenases have previously been described requiring molecular oxygen which may cause oxidative side reactions. Here we show that such compounds can be demethylated anaerobically by using cobalamin-dependent methyltransferases exploiting thiols like ethyl 3-mercaptopropionate as a methyl trap. Using just two equivalents of this reagent, a broad spectrum of substituted guaiacol derivatives were demethylated, with conversions mostly above 90 %. This strategy was used to prepare the highly valuable antioxidant hydroxytyrosol on a one-gram scale in 97 % isolated yield.
- Grimm, Christopher,Kroutil, Wolfgang,Pompei, Simona,Schiller, Christine,Schober, Lukas
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supporting information
p. 16906 - 16910
(2021/07/02)
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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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- Understanding the role played by protic ionic liquids (PILs) and the substituent effect for enhancing the generation of: Z-cinnamic acid derivatives
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Photoisomerization of a series of substituted E-cinnamic acids in MeCN in their acid forms and as their corresponding protic ionic liquids (PILs) with light of 300 nm is studied. The nature, strength, number, and position effects of substituents on the photochemical behavior of E-cinnamic derivatives are investigated. The photosensitization of the reaction in the presence of Michler's ketone is also studied at 366 nm and it demonstrates that the triplet-excited state is involved in the reaction. As the presence of n-butylamine needed to form the PILs significantly increases the photoproduct yields in all cases, the role of the PILs is also discussed. Thus, understanding of these fundamental aspects has allowed us to establish an excellent and practical synthetic protocol for successfully synthesizing Z-cinnamic acids. This journal is
- Rodríguez, Roció B.,Rodríguez, Roció B.,Zapata, Ramiro L.,Salum, Mariá L.,Salum, Mariá L.,Erra-Balsells, Rosa,Erra-Balsells, Rosa
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p. 819 - 830
(2020/07/03)
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- Oxidative metabolism of typical phenolic compounds of Danshen by electrochemistry coupled to quadrupole time-of-flight tandem mass spectrometry
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An electrochemistry coupled to online quadrupole time-of-flight tandem mass spectrometry (EC/Q-TOF/MS) was applied to investigate the oxidative transformation and metabolic pathway of five phenolic acids in Danshen sample. Simulation of the phase I oxidative metabolism was carried out in an electrochemical reactor equipped with a glassy carbon working electrode. The phase II reactivity of the generated oxidative products towards biomolecules (such as glutathione) was investigated by ways of covalent adduct formation experiments. The results obtained by EC/MS were compared with well-known in vitro studies by conducting rat liver microsome incubations. Structures of the electrochemically produced metabolites were identified by accurate mass measurement and previously results in vivo metabolites. It was indicated that the electrochemical oxidation was in good accordance with similar products found in vivo experiments. In conclusion, this work confirmed that EC/Q-TOF/MS was a promising analytical tool in the prediction of metabolic transformations of functional foods.
- Cao, Jun,Chen, Yan,Dong, Xin,Yang, Juan,Ye, Li-Hong,Zhen, Xiao-Ting,Zheng, Hui
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- Expeditious and sustainable two-step synthesis of sinapoyl-l-malate and analogues: Towards non-endocrine disruptive bio-based and water-soluble bioactive compounds
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Faced with the increasing demand from both the cosmetic industries and consumers for bio-based, safe and natural skin products, sinapoyl-l-malate, widely described for its UV protection in plants, appears to be an excellent alternative to substitute chemical filters in sunscreens. Unfortunately, the only synthetic routes described in the literature were not only tedious but also exhibit a strong negative environmental impact, thus seriously limiting the industrialization and commercialization of sinapoyl-l-malate. Herein, a shorter and greener synthetic pathway involving Meldrum's acid opening with unprotected naturally occurring hydroxy acids and its subsequent Knoevenagel-Doebner condensation with biomass-derived p-hydroxybenzaldehydes was designed and developed. This two-step procedure, whom sustainability has been assessed using green metrics (atom economy (AE), process atom economy (PAE), E-factor and LCA), is a great alternative to the already reported procedures and allows the access to sinapoyl-l-malate and several analogs in average to good yield. The study of the anti-UV properties, stability against UV radiation, radical scavenging and antimicrobial activities of the targets revealed attractive properties as photostable UV filters, antioxidants and preservatives. Moreover, the water solubility brought by the free carboxylic acids facilitates the incorporation of these molecules in cosmetic formulations. Finally, their innocuousness toward endocrine disruption was demonstrated.
- Peyrot, Cédric,Mention, Matthieu M.,Fournier, Robin,Brunissen, Fanny,Couvreur, Julien,Balaguer, Patrick,Allais, Florent
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supporting information
p. 6510 - 6518
(2020/11/09)
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- Caffeic acid synthesis and refining process
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The invention relates to a caffeic acid synthesis and refining process, a raw material 3,4-dihydroxybenzaldehyde and a raw material propane diacid are condensed in a solvent under the effect of an organic base condensation catalyst and a decarboxylation catalyst to form caffeic acid, After the reaction is completed, the acid is added to obtain a caffeic acid crude product, the caffeic acid crude product is added to water to dissolve, and the activated carbon is added for decolouring, and the pale yellow solid is precipitated, filtered, and dried under vacuum to obtain the caffeic acid. The process improves the reaction yield, controls the generation of impurities, has simple operation, and mild reaction conditions, and the reaction time is greatly shortened; the process innovatively selects other solvents, reduces the amount of pyridine, and has the advantages of low cost and easy recovery, at the same time, the molar ratio, reaction temperature and reaction time of each initial raw material are further optimized, the organic solvent extraction is avoided, the post-treatment step is simplified, and the direct crystallization is performed after adding hydrochloric acid, and the pressure of the three-waste treatment can be reduced. The caffeic acid content is greater than 99.5%, and the single impurity of the caffeic acid which can stably controlled being not more than 0.1%.
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Paragraph 0015-0022
(2019/01/10)
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- Synthesis and biological evaluation of 4-arylcoumarins as potential anti-Alzheimer's disease agents
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Alzheimer's disease (AD) is a progressive neurological degenerative disease that has complex pathogenesis. A variety of studies in humans indicate that several enzymes inhibitors can be useful in the treatment of AD, including acetylcholinesterase (AchE), butyrylcholinesterase (BuChE) and monoamine oxidase (MAO). Various substituted 4-arylcoumarin derivatives were synthesised, and their activity in vitro were investigated, including AChE/BuChE inhibitory activity, MAO inhibitory activity, and antioxidant activity. Most of the compounds were found to exhibit high inhibitory activity, and individual compounds have extremely excellent activities. Therefore 4-arylcoumarins provides an idea for drugs design for the development of therapeutic or preventive agents for AD.
- Miao, Yuhang,Sun, Jie,Wang, Xiaojing,Yang, Jie,Yun, Yinling
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- New Flavonoids and Turkesterone-2-O-Cinnamate from Leaves of Rhaponticum uniflorum
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Leaves of Rhaponticum uniflorum (L.) DC. (Asteraceae) afforded 46 compounds including seven new flavonoids that were identified using UV, IR, and NMR spectroscopy and mass spectrometry as 6-hydroxyluteolin-7-O-(2′-O-caffeoyl)-β-D-glucopyranoside (rhaunoside A, 1), 6-hydroxyluteolin-7-O-(6″-O-cinnamoyl)-β-D-glucopyranoside (rhaunoside B, 2), 6-hydroxyluteolin-4′-O-β-D-glucopyranoside (rhaunoside C, 3), nepetin-7-O-(6″-O-caffeoyl)-β-D-glucopyranoside (rhaunoside D, 4), nepetin-7-O-(6″-O-cinnamoyl)-β-D-glucopyranoside (rhaunoside E, 5), nepetin-3′-O-β-D-glucopyranoside (rhaunoside F, 6), and luteolin-7-O-(2″-O-caffeoyl)-β-D-glucopyranoside (rhaunoside G, 7) and the new ecdysteroid turkesterone-2-O-cinnamate (8).
- Olennikov,Kashchenko
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p. 256 - 264
(2019/05/06)
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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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- Lasianosides A–E: New iridoid glucosides from the leaves of lasianthus verticillatus (Lour.) Merr. and their antioxidant activity
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The genus Lasianthus (Rubiaceae) consists of approximately 180 species, of which the greatest species diversity is found in tropical Asia. Some of the Lasianthus species have been used in folk medicine to treat tinnitus, arthritis, fever, and bleeding. Lasianthus verticillatus (Lour.) Merr. (Syn. Lasianthus trichophlebus auct. non Hemsl.) is a shrub, branchlets terete about 1.5–3 m in height. This paper studies the chemical composition of the leaves of L. verticillatus for the first time, which resulted in the isolation of five undescribed iridoid glucosides, lasianosides A–E (1–5), together with three known compounds (6–8). The undescribed structures of isolated compounds (1–5) were characterized by physical and spectroscopic data analyses, including one-dimensional (1D) and two-dimensional (2D) NMR, IR, UV, and high-resolution electrospray ionization mass spectra (HR-ESI-MS). Furthermore, the electronic circular dichroism data determined the absolute configurations of the new compounds. The free radical scavenging properties of isolated compounds was assessed by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay, and their cytotoxicity was assessed toward human lung cancer cell line A549 by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. Among the isolated compounds, 3 and 4 displayed potent radical scavenging activities with IC50 values of 30.2 ± 1.8 and 32.0 ± 1.2 μM, which were comparable to that of Trolox (29.2 ± 0.39 μM), respectively, while 5 possessed moderate activity with an IC50 value of 46.4 ± 2.3 μM. None of the isolated compounds exerted cytotoxicity against human cell line A549. As a result, lasianosides C, D, and E have the potential to be non-toxic safe antioxidant agents.
- Al-Hamoud, Gadah Abdulaziz,Orfali, Raha Saud,Perveen, Shagufta,Mizuno, Kenta,Takeda, Yoshio,Nehira, Tatsuo,Masuda, Kazuma,Sugimoto, Sachiko,Yamano, Yoshi,Otsuka, Hideaki,Matsunami, Katsuyoshi
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- CHEMICAL COMPOSITIONS FOR COMBATING HONEY BEE PESTS AND PATHOGENS
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Compositions and methods that reduce Varroa mite populations within a honey bee colony are disclosed. The compositions and methods utilize relatively high concentrations of one or more naturally occurring molecules that are found within honey and/or propolis within a honey bee colony at low concentrations.
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Paragraph 0035
(2019/12/15)
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- METHOD FOR THE SYNTHESIS AND PRODUCTION OF ALKENYL COMPOUND
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PROBLEM TO BE SOLVED: To provide a method for producing an efficient alkenyl compound conveniently and inexpensively. SOLUTION: A first compound represented by formula (1) reacts with a second compound represented by formula (3), in the presence of amino acid, in solvent containing amine, in a range of 50-200°C, to produce an alkenyl compound represented by formula (A) [where R1 is hydrogen or an optionally substituted C1-C30 alkyl group, R2 is a carboxyl group or the like, R3 and R4 are hydrogen, an optionally substituted C1-C30 alkyl group or the like]. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0049; 0087
(2018/09/20)
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- Design, synthesis of N-phenethyl cinnamide derivatives and their biological activities for the treatment of Alzheimer's disease: Antioxidant, beta-amyloid disaggregating and rescue effects on memory loss
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Gx-50 is a bioactive compound for the treatment of Alzheimer's disease (AD) found in Sichuan pepper (Zanthoxylum bungeanum). In order to find a stronger anti-AD lead compound, 20 gx-50 (1-20) analogs have been designed and synthesized, and their molecular structures were determined based on nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis, as well as comparison with literature data. Compounds 1-20 were evaluated for their anti-AD potential by using DPPH radical scavenging assay for considering their anti-oxidant activity, thioflavin T (ThT) fluorescence assay for considering the inhibitory or disaggregate potency of Ab, and transgenic Drosophila model assay for evaluating their rescue effect on memory loss. Finally, compound 13 was determined as a promising anti-AD candidate.
- Chai, Tian,Zhao, Xiao-Bo,Wang, Wei-Feng,Qiang, Yin,Zhang, Xiao-Yun,Yang, Jun-Li
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- Novel piperazine amides of cinnamic acid derivatives as tyrosinase inhibitors
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Background: A series of novel cinnamic acid piperazine amide derivatives has been designed and synthesized, and their biological activities were also evaluated as potential tyrosinase inhibitors. Methods: Compounds 9, 11 and 17 showed the most potent biological activity (IC50 = 66.5, 61.1 and 66 μM, respectively). In silico docking simulation was performed to position compound 11 into the Agaricus bisporus mushroom tyrosinase’s active site to determine the putative binding interactions. Results and Conclusion: The results indicated that compound 11 could serve as a promising lead compound for further development of potent tyrosinase inhibitors.
- Gür, Zehra Tu??e,?enol, Fatma Sezer,Shekfeh, Suhaib,Orhan, ?lkay Erdo?an,Bano?lu, Erden,?ali?kan, Burcu
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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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- Preparation method of 3,4-diacetoxystyrene
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The invention relates to a preparation method of 3,4-diacetoxystyrene. The method comprises the steps of allowing 3,4-dihydroxy benzaldehyde and malonic acid to react in the presence of at least one organic solvent and a catalyst at 60-70 DEG C to generate a first reaction mixture containing 3,4-dihydroxy cinnamic acid, heating up to 80-90 DEG C to allow the first reaction mixture to continue reaction to generate a second reaction mixture containing 3,4-dyhydroxy styrene, allowing 3,4-dyhydroxy styrene to react with an acetylation reagent to generate a third reaction mixture containing 3,4-diacetoxystyrene, and purifying the third reaction mixture to form 3,4-diacetoxystyrene. The invention further provides a preparation method of an acetylation derivative of styrene. The method has the benefits that raw materials for preparation are easy to obtain; the cost is low; a synthesis condition is mild; a technology is simple and convenient; a post-treatment procedure is quick; and industrialization is easy to achieve.
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Paragraph 0074; 0097; 0107; 0109
(2018/07/06)
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- Palladium nanoparticles immobilized on amphiphilic and hyperbranched polymer-functionalized magnetic nanoparticles: An efficient semi-heterogeneous catalyst for Heck reaction
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To address the obstacles facing the use of palladium-based homogeneous and heterogeneous catalysts in C─C cross-coupling reactions, a novel semi-heterogeneous support was developed based on hyperbranched poly(ethylene glycol)-block-poly(citric acid)-functionalized Fe3O4 magnetic nanoparticles (Fe3O4@PCA-b-PEG). Because of the surface modification of the Fe3O4 nanoparticles with amphiphilic and hyperbranched polymers (PCA-b-PEG), these hybrid materials are not only soluble in a wide range of solvents (e.g. water, ethanol and dimethylformamide) but also are able to trap Pd2+ ions via complex formation of free carboxyl groups of the PCA dendrimer with metal ions. The reduction of trapped palladium ions in the dendritic shell of Fe3O4@PCA-b-PEG leads to immobilized palladium nanoparticles. The morphology and structural features of the catalyst were characterized using various microscopic and spectroscopic techniques. The catalyst was effectively used in the palladium-catalysed Mizoroki–Heck coupling reaction in water as a green solvent. In addition, the catalyst can be easily recovered from the reaction mixture by applying an external magnetic field and reused for more than ten consecutive cycles without much loss in activity, exhibiting an example of a sustainable and green methodology.
- Tabatabaei Rezaei, Seyed Jamal,Shamseddin, Azin,Ramazani, Ali,Mashhadi Malekzadeh, Asemeh,Azimzadeh Asiabi, Pegah
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- Photocaging of Single and Dual (Similar or Different) Carboxylic and Amino Acids by Acetyl Carbazole and its Application as Dual Drug Delivery in Cancer Therapy
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A new fluorescent photoremovable protecting group (FPRPG) based on acetylcarbazole framework has been explored for the first time release of single and dual (similar or different) substrates from single chromophore. Mechanistic studies of the photorelease process revealed that photorelease of two (similar or different) substrates from acetyl carbazole proceeds via a stepwise pathway. Further, we constructed photoresponsive dual drug delivery system (DDS) to release two different anticancer drugs (caffeic acid and chlorambucil, 1 equiv each). In vitro study reveals that our DDS exhibit excellent properties like biocompatibility, cellular uptake, and photoregulated dual drug release.
- Venkatesh, Yarra,Rajesh,Karthik,Chetan,Mandal, Mahitosh,Jana, Avijit,Singh, N.D. Pradeep
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supporting information
p. 11168 - 11175
(2016/11/28)
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- Discovery of a New Inhibitor of Myeloid Differentiation 2 from Cinnamamide Derivatives with Anti-Inflammatory Activity in Sepsis and Acute Lung Injury
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Acute inflammatory diseases, including acute lung injury and sepsis, remain the most common life-threatening illness in intensive care units worldwide. Cinnamamide has been incorporated in several synthetic compounds with therapeutic potentials including anti-inflammatory properties. However, the possible mechanism and direct molecular target of cinnamamides for their anti-inflammatory effects were rarely investigated. In this study, we synthesized a series of cinnamamides and evaluated their anti-inflammatory activities. The most active compound, 2i, was found to block LPS-induced MD2/TLR4 pro-inflammatory signaling activation in vitro and to attenuate LPS-caused sepsis and acute lung injury in vivo. Mechanistically, we demonstrated that 2i exerts its anti-inflammatory effects by directly targeting and binding MD2 in Arg90 and Tyr102 residues and inhibiting MD2/TLR4 complex formation. Taken together, this work presents a novel MD2 inhibitor, 2i, which has the potential to be developed as a candidate for the treatment of sepsis, and provides a new lead structure for the development of anti-inflammatory agents targeting MD2.
- Chen, Gaozhi,Zhang, Yali,Liu, Xing,Fang, Qilu,Wang, Zhe,Fu, Lili,Liu, Zhiguo,Wang, Yi,Zhao, Yunjie,Li, Xiaokun,Liang, Guang
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p. 2436 - 2451
(2016/04/10)
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- The efficient and selective catalytic oxidation of para-substituted cinnamic acid derivatives by the cytochrome P450 monooxygenase, CYP199A4
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The cytochrome P450 enzyme, CYP199A4, demethylated 4-methoxybenzoic acid, but not 4-methoxyphenylacetic acid, with high product formation activity. The oxidative demethylation of 3-(4-methoxyphenyl)propionic acid was 8-fold more active than 4-methoxyphenylacetic acid and 4-methoxycinnamic acid was efficiently oxidised at a product formation rate of 180 nmol nmol-P450-1 min-1. Accordingly the oxidation of cinnamic acid derivatives was investigated in order to determine the potential of CYP199A4 to act as a biocatalyst for this important class of biological molecules. 4-Methoxy- and 4-methyl-cinnamic acids bound tightly to CYP199A4 and were better substrates for CYP199A4 than cinnamic acid itself. The oxidations of both 4-methoxy- and 4-methyl-cinnamic acids was 100% selective for attack at the para substituent. Certain dimethoxy substituted cinnamic acids were demethylated more efficiently than 4-methoxycinnamic acid and retained the selectivity for the para-methoxy substituent. Only very low product turnover was observed with 3,5-dimethoxycinnamic acid. 4-Isopropylcinnamic acid was hydroxylated and desaturated by CYP199A4 at the isopropyl group. Cinnamic acids with a para-substituted alkyl- and alkyloxy-cinnamic acid framework were a good fit for the active site of the CYP199A4 enzyme and as a consequence were efficiently and selectively oxidised. Whole-cell oxidations resulted in high yields of product and CYP199A4 could be developed for applications in the biocatalytic oxidation of cinnamic acid derivatives and related phenylpropanoids.
- Chao, Rebecca R.,De Voss, James J.,Bell, Stephen G.
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p. 55286 - 55297
(2016/07/06)
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- A green chemical synthesis of coumarin-3-carboxylic and cinnamic acids using crop-derived products and waste waters as solvents
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Crop-derived products, like juices obtained from edible fruits and vegetables, and waste waters deriving from agricultural and industrial processing have been recently exploited to efficiently promote several ‘classic’ and innovative synthetic organic reactions. Such a green chemical approach prevented the use of toxic, polluting, and hazardous materials and in the mean time allowed to increase the commercial values of crop products and industrial byproducts. Coumarin-3-carboxylic and cinnamic acids represent classes of naturally occurring and semi-synthetic compounds with interesting and promising pharmacological activities. In this Letter a new and improved methodology for the Knoevenagel condensation yielding the title compounds using juices from edible fruits and vegetables (lemon, grapefruit, carrot, pomegranate, kiwi, vinegar, tomato), liqueurs (limoncello), and waste waters (buttermilk and residues of olive processing) as solvents is described. Coumarin-3-carboxylic and cinnamic acids have been synthesized in excellent yields by ultrasound irradiation from differently substituted 2-hydroxybenzaldehydes, 2-hydroxyacetophenones, and benzaldehydes, and Meldrum's acid as starting substrates. The findings described herein enforce the concept of the usefulness of products and byproducts derived from agriculture and food industry to accomplish green chemical processes.
- Fiorito, Serena,Taddeo, Vito Alessandro,Genovese, Salvatore,Epifano, Francesco
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supporting information
p. 4795 - 4798
(2016/10/05)
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- p-Hydroxyphenylacetate 3-Hydroxylase as a Biocatalyst for the Synthesis of Trihydroxyphenolic Acids
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Trihydroxyphenolic acids such as 3,4,5-trihydroxycinnamic acid (3,4,5-THCA) 4c and 2-(3,4,5-trihydroxyphenyl)acetic acid (3,4,5-THPA) 2c are strong antioxidants that are potentially useful as medicinal agents. Our results show that p-hydroxyphenylacetate (HPA) 3-hydroxylase (HPAH) from Acinetobacter baumannii can catalyze the syntheses of 3,4,5-THPA 2c and 3,4,5-THCA 4c from 4-HPA 2a and p-coumaric acid 4a, respectively. The wild-type HPAH can convert 4-HPA 2a completely into 3,4,5-THPA 2c within 100 min (total turnover number (TTN) of 100). However, the wild-type enzyme cannot efficiently synthesize 3,4,5-THCA 4c. To improve the efficiency, the oxygenase component of HPAH (C2) was rationally engineered in order to maximize the conversion of p-coumaric acid 4a to 3,4,5-THCA 4c. Results from site-directed mutagenesis studies showed that Y398S is significantly more effective than the wild-type enzyme for the synthesis of 3,4,5-THCA 4c; it can catalyze the complete bioconversion of p-coumaric acid 4a to 3,4,5-THCA 4c within 180 min (TTN ～ 23 at 180 min). The yield and stability of 3,4,5-THPA 2c and 3,4,5-THCA 4c were significantly improved in the presence of ascorbic acid. Thermostability studies showed that the wild-type C2 was very stable and remained active after incubation at 30, 35, and 40 °C for 24 h. Y398S was moderately stable because its activity was retained for 24 h at 30 °C and for 15 h at 35 °C. Transient kinetic studies using stopped-flow spectrophotometry indicated that the key improvement in the reaction of Y398S with p-coumaric acid 4a lies within the protein-ligand interaction. Y398S binds to p-coumaric acid 4a with higher affinity than the wild-type enzyme, resulting in a shift in equilibrium toward favoring the productive coupling path instead of the path leading to wasteful flavin oxidation.
- Dhammaraj, Taweesak,Phintha, Aisaraphon,Pinthong, Chatchadaporn,Medhanavyn, Dheeradhach,Tinikul, Ruchanok,Chenprakhon, Pirom,Sucharitakul, Jeerus,Vardhanabhuti, Nontima,Jiarpinitnun, Chutima,Chaiyen, Pimchai
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p. 4492 - 4502
(2015/08/18)
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- A highly efficient transformation of cis- to trans-cinnamic acid derivatives by iodine
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Cinnamic acid derivatives (CAs), which have proven to be versatile components, are present in abundance in biologically active natural products, and are widely used as intermediates in the manufacture of pharmaceuticals, and chemicals. The presence of cis- and trans-CAs created difficulties for natural product and organic synthetic studies. A highly efficient method that utilized iodine to entirely convert cis- CAs into their trans-forms was developed to solve this problem. The mechanism of study revealed this conversion occurred via an anti-diiodo intermediate.
- Li, Zhen-Jie,Cai, Le,Mei, Rui-Feng,Dong, Jian-Wei,Li, Shu-Quan,Yang, Xue-Qiong,Zhou, Hao,Yin, Tian-Peng,Ding, Zhong-Tao
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supporting information
p. 7197 - 7200
(2015/12/12)
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- Characterization of caffeoylglucoside derivatives and hypouricemic activity of the ethyl acetate fraction from Aster glehni
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In the search for xanthine oxidase (XOD) inhibitors as anti-gout agents from natural products, various chromatographic separations of the ethyl acetate-soluble fraction of Aster glehni (AGEF) led to the isolation of five new caffeoylglucoside derivatives, namely 6′-O-caffeoyl-(6S,9R)-roseoside (1), 6′-O-caffeoylampelopsisionoside (2), 6′-O-caffeoylsonchuinoside C (3), 6′-O-caffeoyldihydrosyringin (4), and (2E)-2-methyl-but-2-ene-1,4-diol-6′-O-caffeoyl-1-O-β-glucopyranoside (glehnoside, 5), together with 13 known compounds. The absolute stereochemistry of the 6′-O-caffeoylsonchuinoside C (3) was established with the help of spectroscopic analyses, enzymatic hydrolysis, and Mosher's method, as well as in comparison with literature data. All isolated substances were determined for their inhibitory activities on uric acid production by the xanthine/XOD system. Among them, 4,5-O-dicaffeoylquinic acid methyl ester (12) showed the most potent inhibitory activity with an IC50 value of 2.6 ± 0.1 μM, which was comparable to that of allopurinol used as a positive control. Furthermore, hypouricemic effects of AGEF were assessed by measuring serum uric acid levels 3 h after potassium oxonate treatment (250 mg/kg, i.p.) to induce hyperuricemia in rats. When preadministered orally once a day at doses of 50, 100, and 300 mg/kg for 7 days, AGEF reduced the potassium oxonate-induced elevated serum uric acid level by 15.4, 39.8, and 32.3%, respectively. The results suggest that AGEF has the potential to be a new source of agents for the prevention and/or treatment of hyperuricemia and gout.
- Son, Min Jeoung,Jin, Changbae,Lee, Yong Sup,Lee, Jae Yeol,Kim, Hyoung Ja
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p. 503 - 512
(2015/05/06)
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- Spinacetin, A New Caffeoylglycoside, and Other Phenolic Compounds from Gnaphalium uliginosum
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The new flavonoid gnaphaloside C, which was identified based on UV, MS, and NMR spectral data as spinacetin-7-O-(6-O-caffeoyl)-β-D-glucopyranoside, and 24 known compounds including for the first time from this species quercetagetrin, quercetagetin-7-O-(6-O-caffeoyl)glucoside, patulitrin, tinctoside, and spinacetin-7-O-glucoside were isolated from the aerial part of Gnaphalium uliginosum. HPLC determined that G. uliginosum contained mainly caffeoylquinic acids (10.54-48.48 mg/g). The flavonoid content was 1.20-16.55 mg/g.
- Olennikov,Chirikova,Kashchenko
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p. 1085 - 1090
(2016/02/18)
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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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- 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 and biological evaluation of hydroxycinnamic acid hydrazide derivatives as inducer of caspase-3
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In order to generate compounds with superior antitumor activity and reduced toxicity, twelve new hydroxycinnamic acid hydrazide derivatives were synthesized and evaluated for their antiproliferative activities against two cancer cell lines (H1299 lung carcinoma cells and MCF-7 breast cancer cells), and compared to two normal counterparts (NL-20 lung epithelial cells and H184B5F5/M10 breast cells) by MTT method. The results demonstrated that some of these compounds possessed good antiproliferative activity against the two cancer cell lines. Among them, compound 2c was active against the growth of H1299 lung carcinoma cells with IC50 values of 1.50 μM, which was more active than the positive topotecan (IC50 = 4.18 μM). Simultaneously, it showed lower cytotoxic effects on normal NL-20 lung epithelial cells (IC50 > 10 μM). Mechanism studies indicated that it induced cell cycle arrest at G2/M phase followed by activation of caspase-3, and consequently caused the cell death. Further studies on the structure optimization are ongoing.
- Wu, Zheng-Rong,Liu, Jian,Li, Jian-Ying,Zheng, Li-Fang,Li, Yang,Wang, Xing,Xie, Qing-Jian,Wang, Ai-Xia,Li, Ying-Hui,Liu, Rong-Hui,Li, Hong-Yu
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p. 778 - 783
(2014/11/08)
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- Novel flavonol glycosides from the aerial parts of lentil (Lens culinaris)
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While the phytochemical composition of lentil (Lens culinaris) seeds is well described in scientific literature, there is very little available data about secondary metabolites from lentil leaves and stems. Our research reveals that the aerial parts of lentil are a rich source of flavonoids. Six kaempferol and twelve quercetin glycosides were isolated, their structures were elucidated using NMR spectroscopy and chemical methods. This group includes 16 compounds which have not been previously described in the scientific literature: quercetin 3-O-P-D-glucopyranosyl(1→2)-β-D-galactopyranoside-7-O-β-D-glucuropyranoside (1), kaempferol 3-O-β-D-glucopyranosyl(1→2)-β-D-galactopyranoside-7-O-β-D-glucuropyranoside (3), their derivatives 4-10,12-15,17,18 acylated with caffeic, p-coumaric, ferulic, or 3,4,5-trihydroxycinnamic acid and kaempferol 3-O-{[(6-O-E - p-coumaroyl)-β-D-glucopyranosyl(1→2)]-α-L-rhamnopyranosyl(1-6)}-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside (11). Their DPPH scavenging activity was also evaluated. This is probably the first detailed description of flavonoids from the aerial parts of lentil.
- Zuchowski, Jerzy,Pecio, Lukasz,Stochmal, Anna
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p. 18152 - 18178
(2015/02/19)
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- Monoterpene glycosides, phenylpropanoids, and acacetin glycosides from Dracocephalum foetidum
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Chemical investigation of the acetone extract from the aerial parts of the Mongolian medicinal plant Dracocephalum foetidum resulted in the isolation of three limonene glycosides, a caffeic acid trimer, four rosmarinic acid glucosides, and five acacetin acyl glycosides, together with 13 known natural products. The chemical structures of all of the compounds were determined by spectroscopic analyses. Among these compounds three showed hyaluronidase inhibitory activity. In addition, one other compound showed stronger 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity than the positive control Trolox, whereas three other compounds demonstrated a similar activity to that of Trolox.
- Selenge, Erdenechimeg,Murata, Toshihiro,Tanaka, Shiho,Sasaki, Kenroh,Batkhuu, Javzan,Yoshizaki, Fumihiko
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- Cinnamic anilides as new mitochondrial permeability transition pore inhibitors endowed with ischemia-reperfusion injury protective effect in vivo
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In this account, we report the development of a series of substituted cinnamic anilides that represents a novel class of mitochondrial permeability transition pore (mPTP) inhibitors. Initial class expansion led to the establishment of the basic structural requirements for activity and to the identification of derivatives with inhibitory potency higher than that of the standard inhibitor cyclosporine-A (CsA). These compounds can inhibit mPTP opening in response to several stimuli including calcium overload, oxidative stress, and thiol cross-linkers. The activity of the cinnamic anilide mPTP inhibitors turned out to be additive with that of CsA, suggesting for these inhibitors a molecular target different from cyclophylin-D. In vitro and in vivo data are presented for (E)-3-(4-fluoro-3-hydroxy-phenyl)-N-naphthalen-1-yl- acrylamide 22, one of the most interesting compounds in this series, able to attenuate opening of the mPTP and limit reperfusion injury in a rabbit model of acute myocardial infarction.
- Fancelli, Daniele,Abate, Agnese,Amici, Raffaella,Bernardi, Paolo,Ballarini, Marco,Cappa, Anna,Carenzi, Giacomo,Colombo, Andrea,Contursi, Cristina,Di Lisa, Fabio,Dondio, Giulio,Gagliardi, Stefania,Milanesi, Eva,Minucci, Saverio,Pain, Gilles,Pelicci, Pier Giuseppe,Saccani, Alessandra,Storto, Mariangela,Thaler, Florian,Varasi, Mario,Villa, Manuela,Plyte, Simon
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p. 5333 - 5347
(2014/07/08)
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- Acylated sucroses and acylated quinic acids analogs from the flower buds of Prunus mume and their inhibitory effect on melanogenesis
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The methanolic extract from the flower buds of Prunus mume, cultivated in Zhejiang Province, China, showed an inhibitory effect on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells. From the methanolic extract, five acylated sucroses, mumeoses A-E, and three acylated quinic acid analogs, 5- O-(E)-p-coumaroylquinic acid ethyl ester, and mumeic acid-A and its methyl ester, were isolated together with 13 known compounds. The chemical structures of the compounds were elucidated on the basis of chemical and physicochemical evidence. Inhibitory effects of the isolated compounds on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells were also investigated. Acylated quinic acid analogs substantially inhibited melanogenesis. In particular, 5-O-(E)-feruloylquinic acid methyl ester exhibited a potent inhibitory effect [inhibition (%): 21.5 ± 1.0 (P 97% at 10 μM]. It is concluded that acylated quinic acid analogs are promising therapeutic agents for the treatment of skin disorders.
- Nakamura, Seikou,Fujimoto, Katsuyoshi,Matsumoto, Takahiro,Nakashima, Souichi,Ohta, Tomoe,Ogawa, Keiko,Matsuda, Hisashi,Yoshikawa, Masayuki
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p. 128 - 136
(2013/10/21)
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- A novel feruloyl esterase from a soil metagenomic library with tannase activity
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A gene (tan410) encoding a feruloyl esterase was isolated by screening a cotton soil metagenomic library. Sequence analysis revealed that tan410 encodes a protein of 520 amino acids with a predicted molecular weight of 55 kDa. The gene was further expressed in Escherichia coli BL21 (DE3) using a pET expression system. The recombinant enzyme was purified and characterized. Its optimum temperature and pH were 35 °C and 7.0, respectively. Tan410 activity was enhanced by the addition of Mn2+, Mg2+, NH 4+ and Ni2+. Besides ethyl ferulate, methyl caffeate, and methyl p-coumarate, Tan410 can also hydrolyze methyl gallate, tannic acid, epicatechin gallate, and epigallocatechin gallate which makes Tan410 an interesting enzyme for biotechnological applications.
- Yao, Jian,Chen, Qing Long,Shen, Ai Xi,Cao, Wen,Liu, Yu Huan
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- 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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