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Berlin Brandenburg

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  • American Chemical Society (CrossRef)  (122)
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  • 1
    Language: English
    In: The Journal of organic chemistry, 04 April 2014, Vol.79(7), pp.3206-14
    Description: A diverse library of novel carbamates was synthesized utilizing copper-catalyzed oxidative C-O coupling of formamides and salicylaldehydes. Sensitive aldehyde groups remained intact in the presence of an oxidant and a transition-metal salt. Salicylaldehydes bearing electron-donating, electron-withdrawing, and halogen groups as well as 1-hydroxy-2-naphthaldehydes provided the desired carbamates in good to excellent yields.
    Keywords: Aldehydes -- Chemistry ; Carbamates -- Chemical Synthesis ; Copper -- Chemistry ; Formamides -- Chemistry
    ISSN: 00223263
    E-ISSN: 1520-6904
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  • 2
    Language: English
    In: Journal of agricultural and food chemistry, 14 September 2011, Vol.59(17), pp.9219-25
    Description: Recycling agricultural resources has become an important issue worldwide promoting the economical value of agricultural production processes. Desugared sugar cane extract (DSE) from Saccharum officinarum is a byproduct obtained during sugar production. Two new neolignan glucosides, saccharnan A (1) and saccharnan B (2), together with 10 known phenolics (3-12) were isolated from DSE, and their structures were elucidated on the basis of NMR spectral analysis. Compounds 3, 4, 8, and 9 showed good activity against DPPH radical (IC(50) ≤ 51.20 μM) and compounds 3-8 and 12 exhibited strong ABTS(+) free radical scavenging activity (IC(50) ≤ 51.57 μM) compared to those of the positive controls, ascorbic acid and Trolox. Moreover, compounds 7 and 12 acted as potent tyrosinase inhibitors (IC(50) ≤ 42.59 μM) compared to the positive control arbutin. Our results highlighted the economical value of recycling DSE for the future development of natural antioxidants and/or tyrosinase inhibitors.
    Keywords: Antioxidants -- Analysis ; Enzyme Inhibitors -- Analysis ; Monophenol Monooxygenase -- Antagonists & Inhibitors ; Plant Extracts -- Chemistry ; Saccharum -- Chemistry
    ISSN: 00218561
    E-ISSN: 1520-5118
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  • 3
    Language: English
    In: Organic letters, 04 April 2014, Vol.16(7), pp.1912-5
    Description: Iron catalyzed oxidative coupling of salicylaldehydes with cyclic ethers proceeded through the direct α-C-H functionalization of ethers, forming the corresponding acetals in moderate to excellent yields. This is the first example of iron catalyzed selective C-O bond formation in the presence of a sensitive aldehyde moiety.
    Keywords: Acetals -- Chemistry ; Aldehydes -- Chemistry ; Ethers, Cyclic -- Chemistry ; Iron -- Chemistry
    ISSN: 15237060
    E-ISSN: 1523-7052
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  • 4
    Language: English
    In: Journal of medicinal chemistry, 09 August 2012, Vol.55(15), pp.6985
    Keywords: Pharmacy, Therapeutics, & Pharmacology ; Chemistry;
    E-ISSN: 1520-4804
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  • 5
    Language: English
    In: Journal of agricultural and food chemistry, 24 February 2016, Vol.64(7), pp.1540-8
    Description: Cordyceps militaris (bei-chong-chaw, northern worm grass) is a precious and edible entomopathogenic fungus, which is widely used in traditional Chinese medicine (TCM) as a general booster for the nervous system, metabolism, and immunity. Saccharides, nucleosides, mannitol, and sterols were isolated from this fungus. The biological activity of C. militaris was attributed to the saccharide and nucleoside contents. In this study, the aqueous methanolic fraction of C. militaris fruiting bodies exhibited a significant anti-inflammatory activity. Bioactivity-guided fractionation of the active fraction led to the isolation of eight compounds, including one new and two known cerebrosides (ceramide derivatives), two nucleosides, and three sterols. Cordycerebroside A (1), the new cerebroside, along with soyacerebroside I (2) and glucocerebroside (3) inhibited the accumulation of pro-inflammatory iNOS protein and reduced the expression of COX-2 protein in LPS-stimulated RAW264.7 macrophages. This is the first study on the isolation of cerebrosides with anti-inflammatory activity from this TCM.
    Keywords: Cordyceps Militaris ; Lps-Stimulated Raw264.7 Macrophages ; Anti-Inflammatory ; Cerebrosides ; Fungal Fruiting Bodies ; Anti-Inflammatory Agents -- Chemistry ; Cerebrosides -- Chemistry ; Cordyceps -- Chemistry
    ISSN: 00218561
    E-ISSN: 1520-5118
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  • 6
    Language: English
    In: Journal of agricultural and food chemistry, 27 April 2011, Vol.59(8), pp.4288-93
    Description: We evaluated the possible anticancer performance of a natural compound, goniothalamin (GTN), against human lung cancer using as a non-small cell lung cancer (NSCLC) cell line, H1299, as the model system. Cellular proliferation was significantly inhibited by GTN. Using an improved alkaline comet-nuclear extract (comet-NE) assay, GTN was found to induce a significant increase in the tail DNA. Wound healing and zymography assays showed that GTN attenuated cell migration and caused a reduction in the activity level of two major migration-associated matrix metalloproteinases, MMP-2 and MMP-9. It can be concluded that the DNA-damaging effect of GTN against lung cancer cells leads to growth inhibition as well as a depression in migration ability. Therefore, GTN has potential as a chemotherapeutic agent against lung cancer.
    Keywords: Apoptosis -- Drug Effects ; Carcinoma, Non-Small-Cell Lung -- Pathology ; Cell Division -- Drug Effects ; Cell Movement -- Drug Effects ; DNA Damage -- Drug Effects ; Lung Neoplasms -- Pathology ; Pyrones -- Pharmacology
    ISSN: 00218561
    E-ISSN: 1520-5118
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  • 7
    Language: English
    In: Analytical chemistry, 03 September 2013, Vol.85(17), pp.8268-76
    Description: The weak and variable binding affinities exhibited by lectin-carbohydrate interactions have often compromised the practical utility of lectin in capturing glycoproteins for glycoproteomic applications. We report here the development and applications of a new type of hybrid biomaterial, namely a boronic acid-decorated lectin (BAD-lectin), for efficient bifunctional glycoprotein labeling and enrichment. Our binding studies showed an enhanced affinity by BAD-lectin, likely to be mediated via the formation of boronate ester linkages between the lectin and glycan subsequent to the initial recognition process and thus preserving its glycan-specificity. Moreover, when attached to magnetic nanoparticles (BAD-lectin@MNPs), 2 to 60-fold improvement on detection sensitivity and enrichment efficiency for specific glycoproteins was observed over the independent use of either lectin or BA. Tested at the level of whole cell lysates for glycoproteomic applications, three different types of BAD-lectin@MNPs exhibited excellent specificities with only 6% overlapping among the 295 N-linked glycopeptides identified. As many as 236 N-linked glycopeptides (80%) were uniquely identified by one of the BAD-lectin@MNPs. These results indicated that the enhanced glycan-selective recognition and binding affinity of BAD-lectin@MNPs will facilitate a complementary identification of the under-explored glycoproteome.
    Keywords: Boronic Acids -- Chemistry ; Glycoproteins -- Analysis ; Lectins -- Analysis
    ISSN: 00032700
    E-ISSN: 1520-6882
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  • 8
    Language: English
    In: Journal of medicinal chemistry, 24 July 2014, Vol.57(14), pp.6008-18
    Description: Twelve novel 20-sulfonylamidine derivatives (9a-9l) of camptothecin (1) were synthesized via a Cu-catalyzed three-component reaction. They showed similar or superior cytotoxicity compared with that of irinotecan (3) against A-549, DU-145, KB, and multidrug-resistant (MDR) KBvin tumor cell lines. Compound 9a demonstrated better cytotoxicity against MDR cells compared with that of 1 and 3. Mechanistically, 9a induced significant DNA damage by selectively inhibiting Topoisomerase (Topo) I and activating the ATM/Chk related DNA damage-response pathway. In xenograft models, 9a demonstrated significant activity without overt adverse effects at 5 and 10 mg/kg, comparable to 3 at 100 mg/kg. Notably, 9a at 300 mg/kg (i.p.) showed no overt toxicity in contrast to 1 (LD50 56.2 mg/kg, i.p.) and 3 (LD50 177.5 mg/kg, i.p.). Intact 9a inhibited Topo I activity in a cell-free assay in a manner similar to that of 1, confirming that 9a is a new class of Topo I inhibitor. 20-Sulfonylamidine 1-derivative 9a merits development as an anticancer clinical trial candidate.
    Keywords: Drug Design ; Amidines -- Chemistry ; Antineoplastic Agents -- Pharmacology ; Camptothecin -- Analogs & Derivatives ; DNA Topoisomerases, Type I -- Metabolism ; Neoplasms, Experimental -- Drug Therapy ; Sulfonamides -- Chemistry ; Topoisomerase I Inhibitors -- Pharmacology
    ISSN: 00222623
    E-ISSN: 1520-4804
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  • 9
    Language: English
    In: Journal of natural products, 27 May 2011, Vol.74(5), pp.1132-41
    Description: Six new withanolides, paraminabeolides A-F (1-6), along with five known compounds, minabeolides-1, -2, -4, -5, and -8 (7-11), were isolated from a Formosan soft coral, Paraminabea acronocephala. The structures of these compounds were elucidated by extensive spectroscopic analysis and chemical transformation. The absolute configuration of 4 was determined by the application of Mosher's method. Compounds 1 and 7 were cytotoxic toward Hep G2 cancer cells. Compounds 1-4 and 7-10 were found to significantly inhibit the accumulation of the pro-inflammatory iNOS protein. Compounds 7-10 also could effectively reduce the expression of COX-2 protein.
    Keywords: Anthozoa -- Chemistry ; Anti-Inflammatory Agents -- Isolation & Purification ; Antineoplastic Agents -- Isolation & Purification ; Cyclooxygenase 2 Inhibitors -- Isolation & Purification ; Nitric Oxide Synthase Type II -- Drug Effects ; Withanolides -- Isolation & Purification
    ISSN: 01633864
    E-ISSN: 1520-6025
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  • 10
    Language: English
    In: Journal of agricultural and food chemistry, 13 August 2003, Vol.51(17), pp.4916-9
    Description: Extracts of soapnut, Sapindus mukorossi Gaertn. (Sapindaceae) showed molluscicidal effects against the golden apple snail, Pomacea canaliculata Lamarck. (Ampullariidae) with LC(50) values of 85, 22, and 17 ppm after treating 24, 48, and 72 h, respectively. Bioassay-directed fractionation of S. mukorossi resulted in the isolation of one new hederagenin-based acetylated saponin, hederagenin 3-O-(2,4-O-di-acetyl-alpha-l-arabinopyranoside)-(1--〉3)-alpha-l-rhamnopyranosyl-(1--〉2)-alpha-l-arabinopyranoside (1), along with six known hederagenin saponins, hederagenin 3-O-(3,4-O-di-acetyl-alpha-l-arabinopyranoside)-(1--〉3)-alpha-l-rhamnopyranosyl-(1--〉2)-alpha-l-arabinopyranoside (2), hederagenin 3-O-(3-O-acetyl-beta-d-xylopyranosyl)-(1--〉3)-alpha-l-rhamnopyranosyl-(1--〉2)-alpha-l-arabinopyranoside (3), hederagenin 3-O-(4-O-acetyl-beta-d-xylopyranosyl)-(1--〉3)-alpha-l-rhamnopyranosyl-(1--〉2)-alpha-l-arabinopyranoside (4), hederagenin 3-O-(3,4-O-di-acetyl-beta-d-xylopyranosyl)-(1--〉3)-alpha-l-rhamnopyranosyl-(1--〉2)-alpha-l-arabinopyranoside (5), hederagenin 3-O-beta-d-xylopyranosyl-(1--〉3)-alpha-l-rhamnopyranosyl-(1--〉2)-alpha-l-arabinopyranoside (6), and hederagenin 3-O-alpha-l-arabinopyranoside (7). The bioassay data revealed that 1-7 were molluscicidal, causing 70-100% mortality at 10 ppm against the golden apple snail.
    Keywords: Molluscacides -- Pharmacology ; Plant Extracts -- Chemistry ; Sapindus -- Chemistry ; Saponins -- Pharmacology ; Snails -- Drug Effects
    ISSN: 0021-8561
    E-ISSN: 15205118
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