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Insect immunity - Constitutive expression of a cysteine-rich antifungal and a linear antibacterial peptide in a termite insect

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JOURNAL OF BIOLOGICAL CHEMISTRY 2001年第6期276卷 4085-4092页

作者： Lamberty, M Zachary, D Lanot, R Bordereau, C Robert, A Hoffmann, JA Bulet, P CNRS Inst Biol Mol & Cellulaire Unite Propre Rech 9022 F-67084 Strasbourg France Univ Bourgogne Zool Lab CNRS Unite Mixte Rech 5548 F-21000 Dijon France

Two novel antimicrobial peptides, which we propose to name termicin and spinigerin, have been isolated from the fungus-growing termite Pseudacanthotermes spiniger (heterometabole insect, Isoptera). Termicin is a 36-amino acid residue antifungal peptide, with six cysteines arranged in a disulfide array similar to that of insect defensins. In contrast to most insect defensins, termicin is C-terminally amidated. Spinigerin consists of 25 amino acids and is devoid of cysteines. It is active against bacteria and fungi, Termicin and spinigerin show no obvious sequence similarities with other peptides. Termicin is constitutively present in hemocyte granules and in salivary glands. The presence of termicin and spinigerin in unchallenged termites contrasts with observations in evolutionary recent insects or insects undergoing complete metamorphosis, in which antimicrobial peptides are induced in the fat body and released into the hemolymph after septic injury.

关键词：氨基酸序列抗菌药/化学抗菌药/分离和提纯抗菌药/药理学抗真菌药/化学抗真菌药/分离和提纯抗真菌药/药理学碱基序列色谱法高压液相半胱氨酸/化学 DNA引物免疫组织化学等翅目/免疫学分子序列数据肽类蛋白质构象重组蛋白质类/化学重组蛋白质类/分离和提纯重组蛋白质类/药理学序列同源性氨基酸动物

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Pilot-scale purification of zeamatin, an antifungal protein from maize

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BIOTECHNOLOGY PROGRESS 2000年第1期16卷 38-43页

作者： Wilson, S Mahiou, B Reiger, R Tentler, S Schimoler, R Orndorff, S Selitrennikoff, CP MycoLog Inc Denver CO 80262 USA Univera Pharmaceut Inc Broomfield CO 80021 USA

Zeamatin is an antifungal protein isolated from the seeds of Zea mays. A practical process for isolation and purification was developed to increase recovery yields for future testing of zeamatin as a novel therapeutic drug. Zeamatin was extracted with buffer from corn meal milled to flour. Solids were removed from the extract using pressure filtration, and zeamatin was purified using two separate reverse-phase chromatography steps. Determination of the amino-terminal amino acid sequence, Western blotting using anti-zeamatin antibody, and activity against Candida albicans were used to confirm that the purified protein was zeamatin. From 5 kg of corn meal, similar to 110 mg of zeamatin was purified to apparent homogeneity.

关键词：氨基酸序列抗真菌药/化学抗真菌药/分离和提纯抗真菌药/药理学生物技术念珠菌白色/药物作用色谱法/仪器和设备色谱法/方法试点项目植物蛋白质类/化学植物蛋白质类/遗传学植物蛋白质类/分离和提纯胰蛋白酶抑制剂玉米/化学玉米/遗传学

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Purification, characterization, and molecular cloning of the gene of a seed-specific antimicrobial protein from pokeweed

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PLANT PHYSIOLOGY 2000年第4期122卷 1015-1024页

作者： Liu, YF Luo, IC Xu, CY Ren, FC Peng, C Wu, CY Zhao, JD Peking Univ Coll Life Sci Natl Lab Membrane Biol Beijing 100871 Peoples R China

A small cysteine-rich protein with antimicrobial activity was isolated from pokeweed (Phytolacca americana) seeds and purified to homogeneity. The protein inhibits the growth of several filamentous fungi and gram-positive bacteria. The protein was highly basic, with a pi higher than 10. The entire amino acid sequence of the protein was determined to be homologous to antimicrobial protein (AMP) from Mirabilis jalapa. The cDNA encoding the P. americana AMP (Pa-AMP-1) and chromosomal DNA containing the gene were cloned and sequenced. The deduced amino acid sequence shows the presence of a signal peptide at the amino terminus, suggesting that the protein is synthesized as a preprotein and secreted outside the cells. The chromosomal gene shows the presence of an intron located within the region encoding the signal peptide. Southern hybridization showed that there was small gene family encoding Pa-AMP. Immunoblotting showed that Pa-AMP-1 was only present in seeds, and was absent in roots, leaves, and stems. The Pa-AMP-1 protein was secreted into the environment of the seeds during germination, and may create an inhibitory zone against soil-borne microorganisms. The disulfide bridges of Pa-AMP-1 were identified. The three-dimensional modeling of Pa-AMP-1 indicates that the protein has a small cystine-knot folding, a positive patch, and a hydrophobic patch.

关键词：氨基酸序列抗真菌药/分离和提纯抗微生物阳离子肽类碱基序列克隆分子 DNA 植物模型分子分子序列数据植物蛋白质类/化学植物蛋白质类/遗传学植物蛋白质类/分离和提纯序列同源性氨基酸

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Terpenoids and flavonoids from Artemisia species

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PLANTA MEDICA 2000年第4期66卷 391-393页

作者： Tang, HQ Hu, J Yang, L Tan, RX Nanjing Univ Sch Life Sci State Key Lab Pharmaceut Biotechnol Nanjing 210093 Peoples R China Nanjing Univ State Key Lab Coordinat Chem Nanjing 210093 Peoples R China Acad Sinica Shanghai Inst Mat Med State Key Lab New Drug Res Shanghai 200031 Peoples R China Lanzhou Univ State Key Lab Appl Organ Chem Lanzhou 730000 Peoples R China

A phytochemical reinvestigation of the aerial parts of Artemisia sieversiana gave a new guaianolide and two known flavones (chrysosplenetin and 5-hydroxy-3',4',6,7-tetramethoxyflavone). Antifungal fractions derived from the chloroform extract of A. annua afforded two cadinane derivatives (arteannuin B and artemisinin), oleanolic acid, beta-sitosterol, stigmasterol, and the four flavones artemetin, bonanzin, eupalitin and chrysosplenetin. Their structures were elucidated by spectral methods. All isolates from the two species were tested in vitro for antifungal activity. Arteannuin B, a main sesquiterpenoid in A. annua, showed antifungal activity against one human (Candida albicans, MIC: 100 mu g/ml) and four plant pathogenic fungi (Gaeumannomyces graminis var. tritici, Rhizoctonia cerealis, Gerlachia nivalis and Verticillium dahliae, MICs: 150, 100, 150 and 100 mu g/ ml, respectively) whereas others showed no antifungal activity. The MIC value of ketoconazole to C. albicans was 1.0 mu g/ml. and those of triadimefon to G. graminis var. tritici and R. cerealis 150 and 100 mu g/ml.

关键词：抗真菌药/化学抗真菌药/分离和提纯抗真菌药/药理学蒿属/化学类黄酮物质/化学类黄酮物质/分离和提纯类黄酮物质/药理学微生物敏感性试验植物药用萜类/化学萜类/分离和提纯萜类/药理学

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Possible role of xanthobaccins produced by Stenotrophomonas sp strain SB-K88 in suppression of sugar beet damping-off disease

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APPLIED AND ENVIRONMENTAL MICROBIOLOGY 1999年第10期65卷 4334-4339页

作者： Nakayama, T Homma, Y Hashidoko, Y Mizutani, J Tahara, S Hokkaido Univ Fac Agr Dept Appl Biosci Kita Ku Sapporo Hokkaido 0608589 Japan Hokkaido Natl Agr Expt Stn Upland Agr Res Ctr Sapporo Hokkaido 0820071 Japan Japan Sci & Technol Corp CREST Kawaguchi 3320012 Japan

Three antifungal compounds, designated xanthobaccins A, B, and C, were isolated from the culture fluid of Stenotrophomonas sp, strain SB-K88, a rhizobacterium of sugar beet that suppresses damping-off disease. Production of xanthobaccin A in culture media was compared with the disease suppression activities of strain SB-K88 and less suppressive strains that were obtained by subculturing,train SB-K88 was applied to sugar beet seeds, and production of xanthobaccin A in the rhizosphere of seedlings was confirmed by using a test tube culture system under hydroponic culture conditions;3 mu g of xanthobaccin A was detected in the rhizosphere on a per-plant basis. Direct application of purified xanthobaccin A to seeds suppressed damping-off disease in soil naturally infested by Pythium spp. We suggest that xanthobaccin A produced by strain SB-K88 plays a key role in suppression of sugar beet damping-off disease.

关键词：抗菌药/药理学抗真菌药/分离和提纯抗真菌药/药理学藜科/微生物学大环内酯类腐霉菌属/药物作用土壤微生物学黄单胞菌属/生理学

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An unusual structural motif of antimicrobial peptides containing end-to-end macrocycle and cystine-knot disulfides

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PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA 1999年第16期96卷 8913-8918页

作者： Tam, JP Lu, YA Yang, JL Chiu, KW Vanderbilt Univ Dept Microbiol & Immunol Nashville TN 37232 USA

Four macrocyclic cystine-knot peptides of 29-31 residues, kalata, circulin A and B (CirA and CirB), and cyclopsychotride, have been isolated from coffee plants but have undetermined physiological functions. These macrocycles and 10 of their analogs prepared by chemical synthesis were tested against nine strains of microbes. Kalata and CirA were specific for the Gram-positive Staphylococcus aureus with a minimum inhibition concentration of approximate to 0.2 mu M. They were relatively ineffective against Gram-negative bacteria such as Escherichia coli and Pseudomonas aeruginosa. However, CirB and cyclopsychotride mere active against both Gram-positive and Gram-negative bacteria. In particular, CirB showed potent activity against E. coli with a minimum inhibitory concentration of 0.41 mu M. All four cyclic peptides were moderately active against two strains of fungi, Candida kefyr and Candida tropicalis, but were inactive against Candida albicans, These macrocycles are cytotoxic and lysed human red blood cell with a lethal dose 50% of 400 mu M. Modifying the Arg residue in kalata with a keto aldehyde significantly reduced its activity against S. aureus whereas blocking the arg in CirA produced no significant effect. The two-disulfide variants and their scrambled disulfide isomers exhibited antimicrobial profiles and potency similar to their native peptides, However, in high-salt assays (100 mM NaCl), few of these macrocyclic peptides, natives or analogs, retained antimicrobial activity, These results show that the macrocyclic peptides possess specific and potent antimicrobial activity that is salt-dependent and that their initial interactions with the microbial surfaces may be electrostatic, an effect commonly found in defensin antimicrobial peptides, Furthermore, their end-to-end cyclic structure with a cystine-knot motif represents a molecular structure of antimicrobials and may provide a useful template for the design of novel peptide antibiotics.

关键词：氨基酸序列抗菌药/化学抗菌药/分离和提纯抗菌药/药理学抗真菌药/化学抗真菌药/分离和提纯抗真菌药/药理学念珠菌属/药物作用细胞存活/药物作用咖啡/化学计算机模拟植物环蛋白质类胱氨酸二硫化物类红细胞/细胞学红细胞/药物作用大肠杆菌/药物作用革兰氏阴性菌/药物作用革兰氏阳性菌/药物作用溶血/药物作用微生物敏感性试验模型分子分子序列数据肽类环/化学肽类环/分离和提纯肽类环/药理学蛋白质构象铜绿假单胞菌/药物作用金黄色葡萄球菌/药物作用人类

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Experimental and theoretical analysis of the interaction of (±)-cis-ketoconazole with β-cyclodextrin in the presence of (+)-L-tartaric acid

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JOURNAL OF PHARMACEUTICAL SCIENCES 1999年第6期88卷 599-607页

作者： Redenti, E Ventura, P Fronza, G Selva, A Rivara, S Plazzi, PV Mor, M Chiesi Farmaceut SpA Chem & Biopharmaceut Dept I-43100 Parma Italy Politecn Milan Dipartimento Chim CNR Ctr Studio Sostanze Organ Nat I-20131 Milan Italy Univ Parma Dipartimento Farmaceut I-43100 Parma Italy

H-1 NMR spectroscopy was used for determining the optical purity of cis-ketoconazole enantiomers obtained by fractional crystallization. The chiral analysis was carried out using beta-cyclodextrin in the presence of (+)-L-tartaric acid. The mechanism of the chiral discrimination process, the stability of the complexes formed, and their structure in aqueous solution were also investigated by H-1 and C-13 chemical shift analysis, two-dimensional NOE experiments, relaxation time measurements, and mass spectrometry experiments. Theoretical models of the three-component interaction were built up on the basis of the available NMR data, by performing a conformational analysis on the relevant fragments on ketoconazole and docking studies on the components of the complex. The model derived from a folded conformation of ketoconazole turned out to be fully consistent with the molecular assembly found in aqueous solution, as inferred from NOE experiments. An explanation of the different association constants for the complexes of the two enantiomers is also provided on the basis of the interaction energies.

关键词：抗真菌药/化学抗真菌药/分离和提纯环糊精类/化学药物相互作用药物稳定性酮康唑/化学酮康唑/分离和提纯质谱分析法模型分子分子构象核磁共振生物分子质子溶液/化学立体异构现象酒石酸盐类/化学热力学水/化学 β环糊精类

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Cyclodextrin inclusion complexes of miconazole and econazole - isolation, toxicity on human cells, and confirmation of a new interpretation of the drug supersaturation phenomenon

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DRUG DEVELOPMENT AND INDUSTRIAL PHARMACY 1999年第4期25卷 463-470页

作者： Pedersen, M Jacobsen, J Sorensen, AM PEDCY DK-7620 Lemvig Denmark Royal Danish Sch Pharm Dept Pharmaceut DK-2100 Copenhagen O Denmark Royal Danish Sch Pharm Dept Analyt & Pharmaceut Chem DK-2100 Copenhagen O Denmark

Parameters that influence the precipitation of the beta-cyclodextrin (beta-CD) inclusion complexes of the antimycotics miconazole and econazole were investigated. The mechanistic reason for the superior antimycotic activity of the miconazole inclusion complex was studied The toxicity of the complex was estimated. The temperature, the buffer strength, and the effect of the addition of hydrotropic agents on the CD solubility diagrams far the antimycotics were estimated The miconazole and the CD dissolution rate for the complex was measured. The hemolytic activity of the miconazole inclusion complex, the physical mixture, miconazole, and the nitrate salt were compared. The toxicity on TR146 oral cell layers was measured. Lowering the temperature meant that both complexes precipitated at lower CD concentrations. Addition of hydrotropic agents and variation of the buffer strength affected the solubility diagrams. The dissolution medium was supersaturated with miconazole. The supersaturation was not disclosed by the traditional method to analyze for drug supersaturation. The miconazole complex was more toxic to erythrocytes than the physical mixture. On the other hand, the toxic effects of the two products on the TR146 cell layers were similar. Lowering the temperature eased the isolation of genuine CD inclusion complexes of miconazole and econazole. The miconazole supersaturation is likely to be the reason for the superior antimycotic activity of the complex. The complex and the physical mixture had about the same toxicity on TR146 cell layers.

关键词：抗真菌药/化学抗真菌药/分离和提纯抗真菌药/药理学细胞培养技术细胞系细胞存活环糊精类/化学药物相互作用益康唑/化学益康唑/分离和提纯益康唑/毒性红细胞/药物作用溶血/药物作用氢离子浓度咪康唑/化学咪康唑/分离和提纯咪康唑/药理学咪康唑/毒性口腔/细胞学硝酸盐类/毒性溶解度温度水/分析 β环糊精类人类

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Antifungal biflavones from Cupressocyparis leylandii

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PLANTA MEDICA 1999年第6期65卷 572-573页

作者： Krauze-Baranowska, M Cisowski, W Wiwart, M Madziar, B Med Acad Gdansk Dept Pharmacognosy PL-80416 Gdansk Poland Univ Agr & Technol Dept Plant Breeding & Seed Prod Olsztyn Poland

From the leaves of Cupressocyparis leylandii (Cupressaceae) cupressuflavone, 4'-O-methylcupressuflavone, amentoflavone, 7-O-methylamentoflavone, 4"'-O-methylamentoflavone and hinokiflavone were isolated. H-1- and C-13-NMR data for 4'-O-methylcupressuflavone are given for the first time. The biflavones from cultivar varieties of C. leylandii (Naylor's Blue, Castlewellan Gold) were chromatographically (HPLC) compared. The antifungal activity of cupressuflavone and 4'-O-methylcupressuflavone against Alternaria alternata, Cladosporium oxysporum, Fusarium culmorum and F. avenaceum was assayed.

关键词：链格孢属/药物作用抗真菌药/化学抗真菌药/分离和提纯抗真菌药/药理学分枝孢子菌属/药物作用类黄酮物质/化学类黄酮物质/分离和提纯类黄酮物质/药理学镰刀菌属/药物作用微生物敏感性试验植物提取物植物叶

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从白鹤灵芝中分离和鉴定抗真菌苯并吡喃衍生物

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国外医药·植物药分册 1993年第6期8卷 268页

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