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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: Tetrahedron, 25 November 2012, Vol.68(47), pp.9694-9700
    Description: Nine new steroids, sclerosteroids A–I ( , , , – ), along with 18 known metabolites ( – , , – ), were isolated from the soft coral These structures were elucidated on the basis of detailed spectroscopic analysis. The absolute configurations of sugar moieties in steroidal glycosides – were determined by HPLC analysis of the -tolylthiocarbamate derivatives of the liberated sugars from hydrolysis of these steroidal giycosides. Cytotoxic and anti-inflammatory activities of these compounds were measured in vitro.
    Keywords: Scleronephthya Gracillimum ; Sclerosteroids ; O-Tolylthiocarbamate ; Cytotoxic Activity ; Anti-Inflammatory Activity ; Chemistry
    ISSN: 0040-4020
    E-ISSN: 1464-5416
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  • 3
    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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  • 4
    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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  • 5
    Language: English
    In: Bioorganic & Medicinal Chemistry Letters, 01 June 2015, Vol.25(11), pp.2421-2424
    Description: There are many reports for andrographolide modification regarding antitumor effects. Transformation of the five-membered lactone ring to furan aromatic ring still results in compounds with good cytotoxicity. To determine further the importance of the five-membered lactone ring and to obtain better lead compounds, we transformed the five-membered lactone ring in andrographolide. New types of -labdane diterpene derivatives were made, whose cytotoxic activities were measured in vitro. Preliminary SAR was summarized and two compounds, and , with good cytotoxic activity were obtained, which have the potential to be developed into new antitumor drugs.
    Keywords: Andrographolide ; Ent-Labdane Diterpene ; SAR ; Cytotoxic Activity ; Medicine ; Chemistry ; Anatomy & Physiology
    ISSN: 0960-894X
    E-ISSN: 1464-3405
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  • 6
    Language: English
    In: Phytochemistry, August 2016, Vol.128, pp.60-70
    Description: Phytochemical study of the methanolic root extract of allowed for the characterization of 18 non-alkaloid terpenoids. Their structures have skeletons composed of six rearranged -podocarpanes, 11 -podocarpanes, and a 3,4- -30- -friedelane. These were characterized based on 2D NMR, IR, UV, and MS spectroscopic analysis and their absolute configurations were determined by single-crystal X-ray studies, as well as by H NMR spectroscopic analysis for the corresponding chiral derivatives. The isolates were evaluated for therapeutic potential against hepatitis C virus (HCV) infection to human hepatoma Huh7.5 cells. Terpenoids with anti-HCV activity were identified from . The 9(10 → 20)- -podocarpanes were reported from this genus for the first time. The amide coupling reaction on 3,4- -30- -friedelane yielded unexpected compounds.
    Keywords: Flueggea Virosa ; Euphorbiaceae ; Anti-Hepatitis C Virus ; Ent-Podocarpane ; 3,4-Seco-30-nor-Friedelane ; Botany
    ISSN: 0031-9422
    E-ISSN: 1873-3700
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  • 7
    Language: English
    In: Phytochemistry, 2010, Vol.71(2), pp.271-279
    Description: Tricin-type flavonolignans ( – ), along with six known phenolic compounds ( – ), were isolated from the EtOAc extract of . Tricin-type flavonolignans, (2 )-dihydrotricin 4′- -( -β-guaiacylglyceryl) ether, (2 )-dihydrotricin 4′- -( -β-guaiacylglyceryl) ether, (2 )-dihydrotricin 4′- -( -β-4-hydroxyphenylglyceryl) ether, tricin 4′- -( -β-4-hydroxyphenylglyceryl) ether, tricin 4′- -( -β-4-hydroxylphenylglyceryl) ether, and (2 )-dihydrotricin 4′- -(β-6′′-methoxy-4′′-oxo-chroman-3′′-yloxy) ether namely calquiquelignan A–F, respectively, were isolated and characterized from the EtOAc extract of . Additionally, six known phenolic compounds, including dihydrotricin, tricin, salcolin A, -hydroxybenzoic acid, (2 , 3 )- -dihydrokapempferol and (2 )-naringenin, were also obtained and identified from the extract. Structures of the flavonolignans were assigned based on spectroscopic analyses that included 1D and 2D NMR spectroscopic techniques, such as HMQC, HMBC, and NOESY. Bioassay results showed that calquiquelignan A, dihydrotricin and (2 )-naringenin exhibited significant vasodilatory potencies, as indicated by 60.3%, 80.3% and 60.9% relaxations, respectively, at 100 μM. Salcolin A showed potent platelet aggregation inhibition, compared with aspirin. Most of the tricin-type derivatives (calquiquelignan A–B, dihydrotricin and tricin) also exhibited more potent hydroxyl radical ( OH) scavenging activity than trolox as characterized by the ultraweak chemiluminescence assay.
    Keywords: Calamus Quiquesetinervius ; Arecaceae ; Vasodilatory Potencies ; Platelet Aggregation ; Hydroxyl Radical ; Flavonolignan ; Calquiquelignan A–F ; Botany
    ISSN: 0031-9422
    E-ISSN: 1873-3700
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  • 8
    Language: English
    In: Phytochemistry, February 2016, Vol.122, pp.184-192
    Description: 3-Methyl-4,5-dihydro-oxepine ( ), four polyoxygenated seco-cyclohexenes ( – ) and two polyoxygenated cyclohexenes ( – ), along with four known compounds, were isolated from . The phytochemical investigation of the methanolic extract of (Annonaceae) leaves led to the isolation of seven compounds including, 3-methyl-4,5-dihydro-oxepine (flexuvaroxepine A), four polyoxygenated seco-cyclohexene (flexuvarin A–D) and two polyoxygenated cyclohexene (flexuvarol A–B) derivatives, together with four known flavones. The structures of the isolated compounds were elucidated using different spectroscopic techniques. A plausible biogenetic route of the new compounds was discussed. The anti-inflammatory activity of the isolated compounds was evaluated by superoxide anion generation and elastase release assays. Among the tested compounds, flexuvarol B and chrysin showed the most potent anti-inflammatory effect by inhibiting superoxide anion generation and elastase release from human neutrophils in response to fMLP with IC 2.25–5.55 μM. Moreover, 5-hydroxy-6,7-dimethoxy-flavone showed selective inhibitory activity on superoxide anion generation (IC = 1.19 ± 0.34 μM).
    Keywords: Uvaria Flexuosa ; Annonaceae ; 3-Methyl-4,5-Dihydro-Oxepine ; Polyoxygenated Cyclohexenes ; Polyoxygenated Seco-Cyclohexenes ; Anti-Inflammatory ; Botany
    ISSN: 0031-9422
    E-ISSN: 1873-3700
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  • 9
    Language: English
    In: Phytochemistry, November 2016, Vol.131, pp.124-129
    Description: Phytochemical investigation of the ethanolic extract of led to isolation of gramaderins A–D, together with thirteen known compounds. All isolates were assayed for their anti-inflammatory activities. Consequently, 5,7-dihydroxy-3,6,3′,4′,5′-pentamethoxyflavone and 5,3′-dihydroxy-3,6,7,4′,5′-pentamethoxyflavone showed significant bioactivities by inhibiting superoxide anion generation. 8-Acetoxy-pentadeca-1,9 ,14-trien-4,6-diyne-3-ol also demonstrated potent inhibition on elastase release. The gramaderins A/C ( -alkyl linked -lactone) and gramaderins B/D ( -alkyl linked -lactone) co-exist in this plant material, of which the latter derivatives are few in nature. Gramaderins C/D possess a special linear dilactone diterpene skeleton, which never been reported. Phytochemical investigation of the ethanolic extract of led to the isolation of gramaderins A–D. Gramaderins C and D possess a linear dilactone diterpene skeleton.
    Keywords: Grangea Maderaspatana ; Asteraceae ; Diterpenes ; Anti-Inflammatory ; Botany
    ISSN: 0031-9422
    E-ISSN: 1873-3700
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  • 10
    Language: English
    In: Phytochemistry, November 2013, Vol.95, pp.315-321
    Description: Torvpregnanosides A and B ( – ), two pregnane glycosides, and torvoside Q ( ), a 23-keto-spirostanol glycoside, along with twelve known steroidal saponins were isolated from . All structures were identified from spectroscopic data, and the compounds were tested for anti-neutrophilic inflammation activity. Structure-activity relationships are discussed. Torvpregnanosides A and B, two pregnane glycosides, and torvoside Q, a 23-keto-spirostanol glycoside, along with twelve known steroidal saponins were isolated from aerial parts of . Of the latter, four of the 23-hydroxy-spirostanol glycosides, and, a yamogenin glycoside, were in this plant discovered. All structures were identified from spectroscopic data, and all the compounds were tested for anti-neutrophilic inflammatory activity. Two compounds showed selective inhibition against elastase release and superoxide anion generation, respectively, by human neutrophils with IC values of 5.66 and 3.59 μM, while two others inhibited both inflammatory mediators with IC values of 0.66–3.49 μM. Structure-activity relationships are discussed.
    Keywords: Solanum Torvum ; Solanaceae ; Steroidal Glycoside ; Anti-Neutrophilic Inflammation ; Botany
    ISSN: 0031-9422
    E-ISSN: 1873-3700
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