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Simultaneous formulation of terbinafine and salvia monoterpenes into chitosan hydrogel with testing biological activity of corresponding dialysates against C. albicans yeast 特比萘芬与鼠尾草单萜同时配制壳聚糖水凝胶并测定其对白色念珠菌的生物活性
Pub Date : 2016-10-22 DOI: 10.1515/znc-2016-0161
Alexandra Kodadová, Z. Vítková, J. Oremusová, P. Herdová, Anton Ťažký, P. Mikuš
Abstract This work was aimed at a progressive formulation of drugs into chitosan hydrogels. It was taken into consideration that a therapeutic effect of the drugs could be enhanced by a combination of natural compounds with chemical (synthetic) drugs. In this work, sage essential oil (SEO) bicyclic monoterpenes with antiflogistic, antiseptic, and antimycotic properties were combined with terbinafine (TB) having a strong antimycotic activity. Detail optimization of the hydrogel-drugs composition (SEO monoterpenes, TB, chitosan, and polysorbate 80 concentrations), based on permeation experiment and UV absorption/GC-MS analysis of permeated species (eucalyptol, camphor, borneol, thujone, TB) in dialysates, was made. Concerning the active drugs formulation, an optimum concentration of TB was set at the level providing maximum release of the SEO monoterpenes. In vitro activity of the dialysates from the optimized hydrogel was tested against Candida albicans showing that a minimum inhibition concentration was significantly exceeded. The experimental results revealed that the chitosan hydrogel was suitable for the simultaneous formulation of the natural drugs (SEO) with chemical drug (TB) resulting in the preparation with acceptable stability, required gel properties, and significant biological activity. Such preparation should be effective in an antimycotic dermal use.
摘要:研究了壳聚糖水凝胶中药物的递进配方。考虑到药物的治疗效果可以通过天然化合物与化学(合成)药物的组合来增强。本研究将具有抗炎、抗菌和抗真菌特性的鼠尾草精油(SEO)双环单萜烯与具有较强抗真菌活性的特比萘芬(TB)结合。通过渗透实验和对透析液中渗透物质(桉叶油、樟脑、冰片、土桐油、TB)的紫外吸收/GC-MS分析,对水凝胶药物组成(SEO单萜烯、TB、壳聚糖、聚山梨酸80浓度)进行了详细优化。在活性药物配方方面,将最佳浓度设定为能最大限度释放SEO单萜的水平。优化后的水凝胶透析液对白色念珠菌的体外活性测试表明,其最低抑制浓度显著超过。实验结果表明,壳聚糖水凝胶适用于天然药物(SEO)和化学药物(TB)的同时配制,制备的水凝胶具有可接受的稳定性、所需的凝胶性能和显著的生物活性。这种制剂在抗真菌的皮肤使用中应该是有效的。
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引用次数: 1
NMR reassignment of stictic acid isolated from a Sumatran lichen Stereocaulon montagneanum (Stereocaulaceae) with superoxide anion scavenging activities 具有超氧阴离子清除活性的苏门答腊地衣Stereocaulon montagneanum (Stereocaulon montagneanum)胶酸的核磁共振重分配
Pub Date : 2016-10-22 DOI: 10.1515/znc-2016-0148
F. Ismed, F. L. Dévéhat, I. Rouaud, S. Ferron, A. Bakhtiar, J. Boustie
Abstract The phytochemical study of Stereocaulon montagneanum harvested in Sumatra (Indonesia) led to the isolation of 11 known compounds including two metabolites not previously described in the genus Stereocaulon, peristictic acid (8) and menegazziaic acid (10). The complete 1H and 13C NMR spectral assignments of stictic acid derivatives are reported with some revisions. Five depsidones belonging to the stictic acid chemosyndrome were superoxide anion scavengers as potent as ascorbic acid and with no toxicity on two human cell lines.
摘要对印度尼西亚苏门答腊岛产的Stereocaulon montagneanum进行了植物化学研究,分离出11种已知化合物,其中包括两种以前未在Stereocaulon属中描述的代谢物,peristicacid(8)和menegazziaic acid(10)。完整的1H和13C核磁共振谱分配报告了一些修订。属于粘酸化学综合征的五种depsidones是超氧阴离子清除剂,与抗坏血酸一样有效,对两种人类细胞系没有毒性。
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引用次数: 14
Structural diversity in echinocandin biosynthesis: the impact of oxidation steps and approaches toward an evolutionary explanation 棘白菌素生物合成的结构多样性:氧化步骤的影响和进化解释的途径
Pub Date : 2016-10-05 DOI: 10.1515/znc-2016-0156
Wolfgang Hüttel
Abstract Echinocandins are an important group of cyclic non-ribosomal peptides with strong antifungal activity produced by filamentous fungi from Aspergillaceae and Leotiomycetes. Their structure is characterized by numerous hydroxylated non-proteinogenic amino acids. Biosynthetic clusters discovered in the last years contain up to six oxygenases, all of which are involved in amino acid modifications. Especially, variations in the oxidation pattern induced by these enzymes account for a remarkable structural diversity among the echinocandins. This review provides an overview of the current knowledge of echinocandin biosynthesis with a special focus on diversity-inducing oxidation steps. The emergence of metabolic diversity is further discussed on the basis of a comprehensive overview of the structurally characterized echinocandins, their producer strains and biosynthetic clusters. For the pneumocandins, echinocandins produced by Glarea lozoyensis, the formation of metabolic diversity in a single organism is analyzed. It is compared to two common models for the evolution of secondary metabolism: the ‘target-based’ approach and the ‘diversity-based’ model. Whereas the early phase of pneumocandin biosynthesis supports the target-based model, the diversity-inducing late steps and most oxidation reactions best fit the diversity-based approach. Moreover, two types of diversity-inducing steps can be distinguished. Although incomplete hydroxylation is a common phenomenon in echinocandin production and secondary metabolite biosynthesis in general, the incorporation of diverse hydroxyprolines at position 6 is apparently a unique feature of pneumocandin biosynthesis, which stands in stark contrast to the strict selectivity found in echinocandin biosynthesis by Aspergillaceae. The example of echinocandin biosynthesis shows that the existing models for the evolution of secondary metabolism can be well applied to parts of the pathway; however, thus far, there is no comprehensive theory that could explain the entire biosynthesis.
棘白菌素是一类重要的环状非核糖体肽,具有较强的抗真菌活性。它们的结构以大量羟基化的非蛋白质原氨基酸为特征。近年来发现的生物合成簇含有多达六种加氧酶,它们都与氨基酸修饰有关。特别是,由这些酶诱导的氧化模式的变化解释了棘白菌之间显着的结构多样性。本文综述了棘白菌素生物合成的最新知识,重点介绍了诱导多样性氧化的步骤。在对棘白菌素的结构特征、产生菌和生物合成菌群进行综述的基础上,进一步讨论了代谢多样性的出现。对于由Glarea lozoyensis产生的尘肺菌、棘球白菌,分析了单个生物代谢多样性的形成。它与二级代谢进化的两种常见模型进行了比较:“基于目标”的方法和“基于多样性”的模型。尽管肺结核菌生物合成的早期阶段支持基于靶标的模型,但诱导多样性的后期步骤和大多数氧化反应最适合基于多样性的方法。此外,可以区分两种类型的多样性诱导步骤。虽然不完全羟基化是棘球菌素生产和次生代谢物生物合成中普遍存在的现象,但在6号位置上多种羟基脯氨酸的结合显然是肺菌素生物合成的独特特征,这与曲霉科棘球菌素生物合成中严格的选择性形成鲜明对比。棘白菌素生物合成的例子表明,现有的次级代谢进化模型可以很好地应用于部分途径;然而,到目前为止,还没有一个全面的理论可以解释整个生物合成过程。
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引用次数: 19
Leaves of Cordia boissieri A. DC. as a potential source of bioactive secondary metabolites for protection against metabolic syndrome-induced in rats Cordia boissieri A. DC的叶子。作为一种具有生物活性的次生代谢物的潜在来源,可以保护大鼠免受代谢综合征的影响
Pub Date : 2016-10-04 DOI: 10.1515/znc-2016-0073
A. Owis, Amira M. Abo-Youssef, A. Osman
Abstract Cordia boissieri A. DC. (Boraginaceae) is traditionally used as an herbal remedy for diabetes by Hispanic women in Southwestern USA. A recent investigation showed the significant protective effect of ethyl acetate extract against metabolic syndrome (MS). However, the corresponding active principles responsible for this effect and relations between their structure and biological actions remain unclear. Thus, ethyl acetate extract was subjected to column chromatography, which yielded seven compounds identified on the basis of spectroscopic data as rutin, hesperidin, kaempferol-3-O-β-d-glucopyranoside, rosmarinic acid, β-sitosterol-3-O-β-d-glucopyranoside, quercetin, and kaempferol. The isolated compounds (5 mg/kg/day) were tested in a fructose enriched-diet rat model using metformin as a standard drug. Blood samples were withdrawn for estimation of MS-associated biomarkers and liver samples were subjected to histopathological and immunohistochemical examination. The isolated compounds impaired most of the changes associated with MS as evidenced by improved insulin sensitivity, glucose tolerance, kidney function, lipid profiles and reduced oxidative stress and inflammation by different degrees. It is worth noting that quercetin and kaempferol showed the most potent effect. Structure-activity relationship study revealed that the presence of 2,3-double bond in ring C and ortho-hydroxylation in ring B increases the flavonoids activity while glycosylation or methylation decreased this activity.
[摘要];(Boraginaceae)传统上被美国西南部的西班牙裔妇女用作治疗糖尿病的草药。最近的一项研究表明乙酸乙酯提取物对代谢综合征(MS)有显著的保护作用。然而,其相应的作用原理及其结构与生物作用之间的关系尚不清楚。因此,对乙酸乙酯提取物进行柱层析,得到7个化合物,根据光谱数据鉴定为芦丁、橙皮苷、山奈酚-3- o -β-d-葡萄糖苷、迷迭香酸、β-谷甾醇-3- o -β-d-葡萄糖苷、槲皮素和山奈酚。将分离的化合物(5 mg/kg/天)在以二甲双胍作为标准药物的富果糖饮食大鼠模型中进行测试。提取血液样本用于估计ms相关的生物标志物,肝脏样本进行组织病理学和免疫组织化学检查。分离的化合物损害了与MS相关的大多数变化,如改善胰岛素敏感性,葡萄糖耐量,肾功能,脂质谱,不同程度地减少氧化应激和炎症。值得注意的是,槲皮素和山奈酚的效果最为显著。构效关系研究表明,C环上2,3-双键的存在和B环上邻羟基化的存在使黄酮类化合物的活性增加,而糖基化或甲基化则使其活性降低。
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引用次数: 7
Caspase-1 from the silkworm, Bombyx mori, is involved in Bombyx mori nucleopolyhedrovirus infection 家蚕Caspase-1与家蚕核多角体病毒感染有关
Pub Date : 2016-10-04 DOI: 10.1515/znc-2016-0133
Qiang Wang, Xiaoli Ju, Liang Chen, Keping Chen
Abstract Caspase-1 is one of the effector caspases in mammals that plays a central role in apoptosis. However, the lepidopteran caspase-1, especially the Bombyx mori caspase-1 (Bm-caspase-1), has not been investigated in detail. In this study, Bm-caspase-1 was identified from an expressed sequence tag database in B. mori by BLAST search. The open reading frame of Bm-caspase-1 contained 879 nucleotides and encoded 293 amino acids with a predicted molecular mass of 33 kDa. Bm-caspase-1 contained two consensus amino acid motifs of caspase cleavage sites, DEGDA and TETDG. Caspase activity assays revealed significant proteolytic activity of the Ac-DEVD-pNA substrate. Bm-caspase-1 can be detected in all tissues and developmental stages by a semi quantitative polymerase chain reaction assay. More importantly, the expression level of Bm-caspase-1 is increased upon baculovirus infection and up-regulated in BmNPV-resistant silkworms. Taken together, these results indicate that Bm-caspase-1 plays an important role during baculovirus infection.
Caspase-1是哺乳动物的效应caspase之一,在细胞凋亡中起核心作用。然而,鳞翅目caspase-1,特别是家蚕caspase-1 (Bm-caspase-1)尚未被详细研究。本研究通过BLAST检索从家蚕表达序列标签数据库中鉴定出Bm-caspase-1。Bm-caspase-1的开放阅读框包含879个核苷酸,编码293个氨基酸,预测分子质量为33 kDa。Bm-caspase-1含有两个公认的caspase裂解位点氨基酸基序:DEGDA和TETDG。Caspase活性测定显示Ac-DEVD-pNA底物具有显著的蛋白水解活性。Bm-caspase-1可以通过半定量聚合酶链反应在所有组织和发育阶段检测到。更重要的是,Bm-caspase-1在杆状病毒感染后表达水平升高,在bmnpv抗性家蚕中表达水平上调。综上所述,这些结果表明Bm-caspase-1在杆状病毒感染过程中起重要作用。
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引用次数: 8
Cytochalasin P1, a new cytochalasin from the marine-derived fungus Xylaria sp. SOF11 海洋真菌Xylaria sp. SOF11新发现的细胞松弛素P1
Pub Date : 2016-10-04 DOI: 10.1515/znc-2016-0122
Ziming Chen, Yuchan Chen, Hongbo Huang, Hongyan Yang, Weimin Zhang, Yulin Sun, J. Wen
Abstract A new cytochalasin, named cytochalasin P1 (1), together with four known analogs (2–5) was isolated from marine-derived fungus Xylaria sp. SOF11 from the South China Sea. The structure of the new compound was elucidated on the basis of MS and NMR (1H, 13C, HSQC, HMBC, and NOESY) data analyses. Compounds 1–5 were tested for their cytotoxicities against four tumor cell lines (SF-268, MCF-7, NCI-H460, and HepG-2). Compounds 1–5 showed significant cytotoxicity against two tumor cell lines MCF-7 and SF-268, with the IC50 values varying between 0.33 and 4.17 μM.
摘要从南海海洋真菌Xylaria sp. SOF11中分离到新的细胞松弛素P1(1)和4个已知类似物(2-5)。通过MS和NMR (1H, 13C, HSQC, HMBC和noesi)数据分析,对新化合物的结构进行了鉴定。化合物1 ~ 5对4种肿瘤细胞系(SF-268、MCF-7、NCI-H460和HepG-2)的细胞毒性进行了测试。化合物1 ~ 5对肿瘤细胞系MCF-7和SF-268表现出显著的细胞毒性,IC50值在0.33 ~ 4.17 μM之间。
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引用次数: 10
Aspernolides L and M, new butyrolactones from the endophytic fungus Aspergillus versicolor 内生真菌杂色曲霉的新丁内酯
Pub Date : 2016-09-21 DOI: 10.1515/znc-2016-0138
S. Ibrahim, G. Mohamed, S. Ross
Abstract During the systematic search of active compounds from endophytic fungi, two new butyrolactones, namely aspernolides L (2) and M (4), together with four known compounds: 1-O-acetylglycerol (1), butyrolactone I (3), butyrolactone VI (5), and (+) alantrypinone (6) were characterized from the EtOAc extract of the endophytic fungus Aspergillus versicolor isolated from the roots of Pulicaria crispa (Asteraceae). Extensive spectroscopic analysis, including 1D, 2D NMR, and HRESIMS, was used to elucidate their structures. Compounds 1, 5, and 6 are reported for the first time from this fungus.
摘要在对内生真菌活性化合物的系统检索中,从鸢尾根内生真菌versicolor Aspergillus versicolor的EtOAc提取物中分离得到了2个新的丁内酯类化合物aspernolides L(2)和M(4),以及4个已知的化合物:1- o -乙酰甘油(1)、丁内酯I(3)、丁内酯VI(5)和(+)alantrypinone(6)。广泛的光谱分析,包括1D, 2D NMR和hremsim,被用来阐明它们的结构。化合物1、5、6为首次从该真菌中分离得到。
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引用次数: 15
Isolation, antimicrobial and antitumor activities of a new polyhydroxysteroid and a new diterpenoid from the soft coral Xenia umbellata 软珊瑚中一种新的多羟基类固醇和二萜类化合物的分离及其抑菌和抗肿瘤活性
Pub Date : 2016-09-14 DOI: 10.1515/znc-2015-0228
S. Ayyad, W. Alarif, K. Al-Footy, E. A. Selim, Mohamed A Ghandourah, M. Aly, H. Alorfi
Abstract A new C-30 steroid, 3β-,5α-,6β-,11α-,20β-pentahydroxygorgosterol (1), and a new diterpenoid, xeniumbellal (2), along with three known aromadendrane-type sesquiterpenes, aromadendrene (3), palustrol (4) and viridiflorol (5), were isolated from the soft coral Xenia umbellata. Chemical structures were determined by analyzing their NMR and MS data. The antimicrobial and antitumor activities of the isolated compounds were examined. Both 1 and 2 showed moderate antibacterial activities, especially against the multidrug-resistant Acinetobacter baumannii (MIC 0.22 and 0.28 mM, respectively); while 2 showed antitumor activity against a lymphoma cell line with LD50 0.57 mM and was nontoxic to Artemia salina at all tested concentrations up to about 4 mM.
摘要从软珊瑚中分离到一种新的C-30甾体,3β-,5α-,6β-,11α-,20β-五羟基山茱萸甾醇(1)和一种新的二萜类,xeniumbellal(2),以及三种已知的芳香腺嘌呤型倍半萜,芳香腺嘌呤(3),棕榈醇(4)和绿双酚(5)。通过分析其核磁共振和质谱数据确定了化学结构。对分离得到的化合物进行了抑菌和抗肿瘤活性研究。1和2均表现出中等抑菌活性,特别是对多药耐药鲍曼不动杆菌(MIC分别为0.22和0.28 mM);2对一株淋巴瘤细胞系具有抗肿瘤活性,LD50为0.57 mM,在4 mM以下的所有浓度下对青蒿素均无毒。
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引用次数: 9
Picturing pathogen infection in plants 植物中病原体感染的图像
Pub Date : 2016-09-01 DOI: 10.1515/znc-2016-0134
M. Barón, M. Pineda, M. Pérez-Bueno
Abstract Several imaging techniques have provided valuable tools to evaluate the impact of biotic stress on host plants. The use of these techniques enables the study of plant-pathogen interactions by analysing the spatial and temporal heterogeneity of foliar metabolism during pathogenesis. In this work we review the use of imaging techniques based on chlorophyll fluorescence, multicolour fluorescence and thermography for the study of virus, bacteria and fungi-infected plants. These studies have revealed the impact of pathogen challenge on photosynthetic performance, secondary metabolism, as well as leaf transpiration as a promising tool for field and greenhouse management of diseases. Images of standard chlorophyll fluorescence (Chl-F) parameters obtained during Chl-F induction kinetics related to photochemical processes and those involved in energy dissipation, could be good stress indicators to monitor pathogenesis. Changes on UV-induced blue (F440) and green fluorescence (F520) measured by multicolour fluorescence imaging in pathogen-challenged plants seem to be related with the up-regulation of the plant secondary metabolism and with an increase in phenolic compounds involved in plant defence, such as scopoletin, chlorogenic or ferulic acids. Thermal imaging visualizes the leaf transpiration map during pathogenesis and emphasizes the key role of stomata on innate plant immunity. Using several imaging techniques in parallel could allow obtaining disease signatures for a specific pathogen. These techniques have also turned out to be very useful for presymptomatic pathogen detection, and powerful non-destructive tools for precision agriculture. Their applicability at lab-scale, in the field by remote sensing, and in high-throughput plant phenotyping, makes them particularly useful. Thermal sensors are widely used in crop fields to detect early changes in leaf transpiration induced by both air-borne and soil-borne pathogens. The limitations of measuring photosynthesis by Chl-F at the canopy level are being solved, while the use of multispectral fluorescence imaging is very challenging due to the type of light excitation that is used.
几种成像技术为评估生物胁迫对寄主植物的影响提供了有价值的工具。利用这些技术,可以通过分析叶片代谢在发病过程中的时空异质性来研究植物与病原体的相互作用。本文综述了基于叶绿素荧光、多色荧光和热成像的成像技术在病毒、细菌和真菌感染植物研究中的应用。这些研究揭示了病原菌胁迫对光合性能、次生代谢和叶片蒸腾的影响,为田间和温室病害管理提供了一种有前景的工具。在叶绿素荧光诱导动力学过程中获得的标准叶绿素荧光(Chl-F)参数图像与光化学过程和能量耗散有关,可以作为监测发病机制的良好胁迫指标。用多色荧光成像技术检测到的紫外诱导的蓝色荧光(F440)和绿色荧光(F520)的变化似乎与植物次生代谢的上调以及参与植物防御的酚类化合物(如东莨菪碱、绿原酸或阿魏酸)的增加有关。热成像显示了发病过程中的叶片蒸腾图,强调了气孔在植物先天免疫中的关键作用。同时使用几种成像技术可以获得特定病原体的疾病特征。这些技术也被证明是非常有用的症状前病原体检测,以及精准农业的强大的非破坏性工具。它们在实验室规模、遥感领域和高通量植物表型分析方面的适用性使它们特别有用。热传感器被广泛应用于作物田间,用于检测空气传播和土壤传播病原体引起的叶片蒸腾的早期变化。在冠层水平上通过Chl-F测量光合作用的局限性正在得到解决,而由于所使用的光激发类型,使用多光谱荧光成像非常具有挑战性。
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引用次数: 44
Ascidian bioresources: common and variant chemical compositions and exploitation strategy – examples of Halocynthia roretzi, Styela plicata, Ascidia sp. and Ciona intestinalis 海鞘生物资源:常见和变异的化学成分及开发策略——以海鞘、皱海鞘、海鞘和海鞘为例
Pub Date : 2016-05-01 DOI: 10.1515/znc-2016-0012
Yadong Zhao, Jiebing Li
Abstract To explore abundant marine ascidian bioresources, four species from two orders have been compared in their chemical compositions. After a universal separation of the animal body into two fractions, all tunics have been found rich in carbohydrate contents, while all inner body tissues are richer in proteins. Cellulose is present almost exclusively in the tunics and more in the order Stolidobranchia, while more sulfated polysaccharides are present in Phlebobranchia species. Almost all proteins are collagens with a high essential amino acid index and high delicious amino acid (DAA) content. All fractions also have high contents of good-quality fatty acids and trace minerals but low toxic element contents, with different sterols and glycosaminoglycans. There are species-specific characteristics observed for vanadium accumulation and sterol structures which are also meaningful for ascidian chemotaxonomy and resource exploitation. It is suggested that in addition to the present utilizations of tunics for cellulose production and of some species’ inner body tissues as human food, one should explore all species’ inner body tissues as human foods and all tunics as food or animal feed with the contained cellulose as dietary fiber. Collagens, sulfated polysaccharides, glycosaminoglycans, sterols and trace elements could be explored as byproducts for, e.g. pharmaceutical and chemical industries.
摘要为了发掘丰富的海洋海鞘生物资源,对2目4种海鞘的化学成分进行了比较。在将动物身体普遍分成两部分后,所有的外衣都含有丰富的碳水化合物,而所有的体内组织都含有丰富的蛋白质。纤维素几乎完全存在于被膜中,更多的存在于匍匐茎目,而更多的硫酸酸化多糖存在于细鳃目。几乎所有的蛋白质都是胶原蛋白,具有高必需氨基酸指数和高美味氨基酸(DAA)含量。各馏分优质脂肪酸和微量矿物质含量高,毒性元素含量低,甾醇和糖胺聚糖含量不同。在钒积累和甾醇结构上观察到的物种特异性特征对海鞘的化学分类和资源开发具有重要意义。建议在目前利用被毛生产纤维素和利用某些物种体内组织作为人类食物的基础上,进一步探索将所有物种体内组织作为人类食物,将所有被毛作为含有纤维素的食物或动物饲料。胶原蛋白、硫酸酸化多糖、糖胺聚糖、甾醇和微量元素可作为副产品用于制药和化工等行业。
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引用次数: 21
期刊
Zeitschrift für Naturforschung C
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