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1.
Three new C19-diterpenoid alkaloids vilmotenitines A-C (1-3), together with seven known ones, vilmorine D (4), talatizidine (5), isotalatizidine (6), vilmorrianine B (7), vilmorrianine D (8), talatizamine (9), 8-deacetyl-yunaconitine (10), were isolated from Aconitum vilmorinianum var. patentipilum. Vilmotenitines A (1) and B (2) are the second natural occurrences of C19-diterpenoid alkaloids with a unique rearranged six-membered B ring formed by the C(8)–C(10) linkage. 相似文献
2.
《Bioorganic & medicinal chemistry》2014,22(12):3180-3186
By targeting the ThDP binding site of Escherichia coli PDHc-E1, two new ‘open-chain’ classes of E. coli PDHc-E1 inhibitors, amide and urea derivatives, were designed, synthesized, and evaluated. The amide derivatives of compound 6d, with 4-NO2 in the benzene ring, showed the most potent inhibition of E. coli PDHc-E1. The urea derivatives displayed more potent inhibitory activity than the corresponding amide derivatives with the same substituent. Molecular docking studies confirmed that the urea derivatives have more potency due to the two hydrogen bonds formed by two NH of urea with Glu522. The docking results also indicate it might help us to design more efficient PDHc-E1 inhibitors that could interact with Glu522. 相似文献
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4.
Codeinone reductase isoforms with differential stability,efficiency and product selectivity in opium poppy 下载免费PDF全文
Mehran Dastmalchi Limei Chang Miguel A. Torres Kenneth K. S. Ng Peter J. Facchini 《The Plant journal : for cell and molecular biology》2018,95(4):631-647
Codeinone reductase (COR) catalyzes the reversible NADPH‐dependent reduction of codeinone to codeine as the penultimate step of morphine biosynthesis in opium poppy (Papaver somniferum). It also irreversibly reduces neopinone, which forms by spontaneous isomerization in aqueous solution from codeinone, to neopine. In a parallel pathway involving 3‐O‐demethylated analogs, COR converts morphinone to morphine, and neomorphinone to neomorphine. Similar to neopine, the formation of neomorphine by COR is irreversible. Neopine is a minor substrate for codeine O‐demethylase (CODM), yielding morphine. In the plant, neopine levels are low and neomorphine has not been detected. Silencing of CODM leads to accumulation of upstream metabolites, such as codeine and thebaine, but does not result in a shift towards higher relative concentrations of neopine, suggesting a mechanism in the plant for limiting neopine production. In yeast (Saccharomyces cerevisiae) engineered to produce opiate alkaloids, the catalytic properties of COR lead to accumulation of neopine and neomorphine as major products. An isoform (COR‐B) was isolated from opium poppy chemotype Bea's Choice that showed higher catalytic activity than previously characterized CORs, and it yielded mostly neopine in vitro and in engineered yeast. Five catalytically distinct COR isoforms (COR1.1–1.4 and COR‐B) were used to determine sequence–function relationships that influence product selectivity. Biochemical characterization and site‐directed mutagenesis of native COR isoforms identified four residues (V25, K41, F129 and W279) that affected protein stability, reaction velocity, and product selectivity and output. Improvement of COR performance coupled with an ability to guide pathway flux is necessary to facilitate commercial production of opiate alkaloids in engineered microorganisms. 相似文献
5.
Richard B. Silverman Graham R. Lawton Hantamalala Ralay Ranaivo Laura K. Chico Jiwon Seo D. Martin Watterson 《Bioorganic & medicinal chemistry》2009,17(21):7593-7605
Several prodrug approaches were taken to mask amino groups in two potent and selective neuronal nitric oxide synthase (nNOS) inhibitors containing either a primary or secondary amino group to lower the charge and improve blood–brain barrier (BBB) penetration. The primary amine was masked as an azide and the secondary amine as an amide or carbamate. The azide was not reduced to the amine under a variety of in vitro and ex vivo conditions. Despite the decrease in charge of the amino group as an amide and as carbamates, BBB penetration did not increase. It appears that the uses of azides as prodrugs for primary amines or amides and carbamates as prodrugs for secondary amines are not universally effective for CNS applications. 相似文献
6.
The 1H NMR spectra of three pyrrolizidine alkaloids of the macrocyclic diester type, retrorsine, seneciphylline and senecionine, plus their three N-oxides have been assigned. Previous 1H NMR studies of these pyrrolizidine alkaloids have stressed the difficulties of spectral intrepretation. The results reported here will provide a useful resource for analysis of tertiary structure in these and related compounds. 相似文献
7.
《植物学报(英文版)》2005,47(7)
The Dai medicinal plant Winchia calophylla A. DC. (Apocynaceae) has efficacy as an anticough and anti-asthmatic medication. In order to investigate its relative bioactive components, we studied the chemical constituents of this plant. Using repeated column chromatography, 28 compounds, including loganin, six phenolic compounds, 17 indole alkaloids, three pyridine alkaloids, and a quinoline alkaloid,were isolated from the stem barks of W. calophylla. Loganin, paeonol, N (4)-methyl akuammicine, and cantleyine exhibited a moderate relaxation effect on isolated smooth muscles of guinea-pig tracheal spirals and lung strips and may be the bioactive components responsible for the bronchodilation produced by W. calophylla. 相似文献
8.
延胡索的化学成分研究(英文) 总被引:2,自引:0,他引:2
采用现代分离技术和方法,从延胡索根茎中分离得到17个化合物,通过波谱分析鉴定其结构。包括11个生物碱类化合物,二氢白屈菜红碱(1)、去氢紫堇碱(2)、四氢非洲防己胺(3)、异紫堇球碱(4)、紫堇碱(5)、四氢黄连碱(6)、药根碱(7)、黄连碱(8)、小檗碱(12)、巴马汀(13)和延胡索乙素(14);2个蒽醌类化合物,大黄素(9)和大黄素甲醚(10);1个三萜类化合物,即3β-羟基-齐墩果烷-111,3(18)-二烯-28-酸(11)和3个甾醇类化合物,豆甾醇(15)、β-谷甾醇(16)和胡萝卜苷(17)。其中,化合物9~11首次从该属植物中分离得到,1首次从该种中分离得到。 相似文献
9.
Synthetic soluble (—)-dopa melanin was prepared in deuteriated buffer, pH 8, by autooxidation of the precursor. At 6 mM of the precursor, the incorporation was over 90%. The changes in the line width measurements of N-CH3 protons of enantiomers of ephedrine in the soluble melanin were quantified by NMR spectroscopy. The dissociation constants of (—)-1R,2S-ephedrine, (+)-1S,2R-ephedrine, (—)-1R,2R-ψ-ephedrine, and (+)-1S,2S-ψ-ephedrine were 11.7, 4.20, 3.60, and 4.80 mM, respectively. Since the concentration of (—)-dopa was known and since the conversion of (—)-dopa to indole units of melanin was considered as 1:1, the stoichiometry of the interaction between the drug and the indole unit was calculated. Based on the dissociation constants of the enantiomers, it appears that up to four molecules of (—)-ephedrine can interact with one indole unit of the melanin, while such a ratio for other isomers appear to be 2:1. The preference by indole units of melanin is stereoselective. © 1992 Wiley-Liss, Inc. 相似文献
10.
Three undescribed aporphine alkaloids dasymaroine A (1), 3-methoxyoxoputerine N-oxide (2), and dasymaroine B (3), along with nine known analogues (4–12) were isolated from the stems of Dasymaschalon rostratum Merr. The structures were elucidated using spectroscopic methods and by comparison with published NMR spectroscopic data. Compound 1 is a rarely reported nitro aporphine alkaloid and its absolute configuration was defined based on negative specific rotation and single-crystal X-ray diffraction. Compound 2 represents the first example of oxoaporphine alkaloid N-oxide. All compounds were evaluated for their activities of six pathogenic bacteria, 1 exhibited significant inhibition against Escherichia coli and Saphylococcus aureus with MIC values of 1.2 and 2.5 μM, respectively. As well as compounds 1–5, 7, 10, 12 were evaluated for their anti-HIV activities with EC50 ranged from 1.93 to 9.70 μM. 相似文献