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Iron Supply Affects Anthocyanin Content and Related Gene Expression in Berries of Vitis vinifera cv. Cabernet Sauvignon 铁供应对葡萄果实花青素含量及相关基因表达的影响赤霞珠
Pub Date : 2017-02-01 DOI: 10.3390/molecules22020283
P. Shi, Bing Li, Haiju Chen, Chang-zheng Song, Jiangfei Meng, Zhumei Xi, Zhen-wen Zhang
Anthocyanins are important compounds for red grape and red wine quality, and can be influenced by supply of nutrients such as nitrogen, phosphorus, potassium, zinc, and iron. The present work aims to gain a better understanding of the effect of iron supply on anthocyanins concentration in grape berries. To this end, own-rooted four-year-old Cabernet Sauvignon grapevines (Vitis vinifera) were fertigated every three days with 0, 23, 46, 92, and 184 μM iron (Fe) from ferric ethylenediamine di (o-hydroxyphenylacetic) acid (Fe-EDDHA) in a complete nutrient solution. Fe deficiency or excess generally led to higher concentrations of titratable acidity and skin/berry ratio, and to lower reducing sugar content, sugar/acid ratio, pH, berry weight, and concentration of anthocyanins. Most of the individual anthocyanins detected in this study, except cyanidin-3-O-glucoside, delphinidin-3-O-glucoside, and cyanidin-3-O-(6-O-coumaryl)-glucoside, in moderate Fe treatment (46 μM) grapes were significantly higher than those of other treatments. Genes encoding chalcone isomerase (CHI), flavanone 3-hydroxylase (F3H), leucoanthocyanidin dioxygenase (LDOX), and anthocyanin O-methyltransferase (AOMT) exhibited higher transcript levels in berries from plants cultivated with 46 μM Fe compared to the ones cultivated with other Fe concentrations. We suggest that grape sugar content, anthocyanins content, and transcriptions of genes involved in anthocyanin biosynthesis were correlated with Fe supply concentrations.
花青素是红葡萄和红葡萄酒品质的重要化合物,它可以受到氮、磷、钾、锌和铁等营养物质供应的影响。本研究旨在更好地了解铁供应对葡萄果实花青素浓度的影响。为此,研究人员在完全营养液中分别用0、23、46、92和184 μM的铁(Fe) (Fe- eddha)对4年生赤霉素(Cabernet Sauvignon)葡萄(Vitis vinifera)进行每3天一次的补铁。铁缺乏或过量通常会导致可滴定酸度浓度和果皮/浆果比升高,还原糖含量、糖/酸比、pH、浆果重量和花青素浓度降低。在中等铁处理(46 μM)葡萄中,除花青素-3- o -葡萄糖苷、飞鸽苷-3- o -葡萄糖苷和花青素-3- o -(6- o -香豆基)-葡萄糖苷外,本研究检测到的大部分花青素均显著高于其他处理。在46 μM铁处理下,查尔酮异构酶(CHI)、黄酮3-羟化酶(F3H)、浅色花青素双加氧酶(LDOX)和花青素o -甲基转移酶(AOMT)基因的转录水平高于其他铁处理。我们认为葡萄的糖含量、花青素含量和参与花青素生物合成的基因转录与铁供应浓度相关。
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引用次数: 26
Efficient Catalytic Oxidation of 3-Arylthio- and 3-Cyclohexylthio-lapachone Derivatives to New Sulfonyl Derivatives and Evaluation of Their Antibacterial Activities 3-芳基硫代和3-环己基硫代拉帕酮衍生物的高效催化氧化合成新的磺酰基衍生物及其抗菌活性评价
Pub Date : 2017-02-01 DOI: 10.3390/molecules22020302
M. Cardoso, A. Gomes, C. Moreira, M. Simões, M. Neves, D. D. da Rocha, F. D. da Silva, C. Moreirinha, A. Almeida, V. Ferreira, J. Cavaleiro
New sulfonyl-lapachones were efficiently obtained through the catalytic oxidation of arylthio- and cyclohexylthio-lapachone derivatives with hydrogen peroxide in the presence of a Mn(III) porphyrin complex. The antibacterial activities of the non-oxidized and oxidized lapachone derivatives against the Gram-negative bacteria Escherichia coli and the Gram-positive bacteria Staphylococcus aureus were evaluated after their incorporation into polyvinylpyrrolidone (PVP) micelles. The obtained results show that the PVP-formulations of the lapachones 4b–g and of the sulfonyl-lapachones 7e and 7g reduced the growth of S. aureus.
在Mn(III)卟啉络合物的存在下,用过氧化氢催化氧化芳基硫代和环己基硫代拉帕酮衍生物,得到了新的磺酰基拉帕酮。将未氧化和氧化拉帕酮衍生物掺入聚乙烯吡咯烷酮(PVP)胶束后,评价其对革兰氏阴性菌大肠杆菌和革兰氏阳性菌金黄色葡萄球菌的抑菌活性。结果表明,拉帕醌4b-g和磺酰基拉帕醌7e和7g的pvp配方可抑制金黄色葡萄球菌的生长。
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引用次数: 7
Emerging Cytotoxic Alkaloids in the Battle against Cancer: Overview of Molecular Mechanisms 抗癌新出现的细胞毒性生物碱:分子机制综述
Pub Date : 2017-02-01 DOI: 10.3390/molecules22020250
Zeina Habli, Georgio Toumieh, Maamoun Fatfat, O. Rahal, H. Gali-Muhtasib
Considered as the second deadliest disease globally, cancer has captured the attention of researchers who have been trying with perseverance to decode its hidden aspects, to find new prognosis methods, and to develop better and more effective treatments. Plants have continuously offered an excess of unique secondary metabolites with remarkable biological applications. Alkaloids, one of the most abundant metabolites, constitute a large conglomerate of basic heterocyclic nitrogen-containing natural compounds which are normally produced by plants as toxic substances. Out of the 27,000 different alkaloids, more than 17,000 have displayed diversified pharmacological properties including anticancer activities. These metabolites have been classified either according to their chemical structures or their taxonomic origin. None of the researched alkaloids have been classified according to their molecular mechanism of action against cancer. In fact, only a fraction of the tremendous number of anticancer alkaloids has been copiously mentioned in journals. Here, we aim to provide a summary of the literature on some of the promising anticancer alkaloids that have not been well discussed previously and to classify them according to their molecular mechanisms of action. This review will provide a better understanding of the anticancer mechanisms of these promising natural products that are a rich reservoir for drug discovery.
癌症被认为是全球第二大致命疾病,已经引起了研究人员的注意,他们一直在坚持不懈地试图破解其隐藏的方面,寻找新的预后方法,并开发更好更有效的治疗方法。植物不断提供过量独特的次生代谢物具有显著的生物学应用。生物碱是最丰富的代谢物之一,是一大类碱性杂环含氮天然化合物,通常由植物作为有毒物质产生。在27,000种不同的生物碱中,超过17,000种显示出多种药理特性,包括抗癌活性。这些代谢物已经根据它们的化学结构或它们的分类起源进行了分类。所研究的生物碱都没有根据其抗癌的分子机制进行分类。事实上,在数量庞大的抗癌生物碱中,只有一小部分在期刊上被大量提及。在这里,我们旨在对一些有前途的抗癌生物碱的文献进行综述,并根据它们的分子作用机制对它们进行分类。这一综述将有助于更好地了解这些有前途的天然产物的抗癌机制,这些天然产物是药物发现的丰富储存库。
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引用次数: 94
Bioactive Benzofuran Derivatives from Cortex Mori Radicis, and Their Neuroprotective and Analgesic Activities Mediated by mGluR1 桑皮生物活性苯并呋喃衍生物及其由mGluR1介导的神经保护和镇痛作用
Pub Date : 2017-02-01 DOI: 10.3390/molecules22020236
Ya-Nan Wang, Mao-feng Liu, Wei-zhen Hou, R. Xu, Jie Gao, An-qi Lu, Mei-ping Xie, Lan Li, Jian-Jun Zhang, Ying Peng, Li-Li Ma, Xiao-Liang Wang, Jiangong Shi, Su-Juan Wang
Four new benzofuran-type stilbene glycosides and 14 known compounds including 8 benzofuran-type stilbenes and 6 flavonoids were isolated from the traditional Chinese medicine, Cortex Mori Radicis. The new compounds were identified as (9R)-moracin P 3′-O-α-l-arabinopyranoside (1), (9R)-moracin P 9-O-β-d-glucopyranoside (2), (9R)-moracin P 3′-O-β-d-glucopyranoside (3), and (9R)-moracin O 10-O-β-d-glucopyranoside (4) based on the spectroscopic interpretation and chemical analysis. Three benzofuran-type stilbenes, moracin O (5), R (7), and P (8) showed significant neuroprotective activity against glutamate-induced cell death in SK-N-SH cells. In addition, moracin O (5) and P (8) also demonstrated a remarkable inhibition of the acetic acid-induced pain. The molecular docking with metabotropic glutamate receptor 1 (mGluR1) results indicated that these neuroprotective benzofuran-type stilbenes might be the active analgesic components of the genus Morus, and acted by mediating the mGluR1 pathway.
从中药桑皮中分离得到4个新的苯并呋喃型二苯乙烯苷类化合物和14个已知化合物,包括8个苯并呋喃型二苯乙烯类化合物和6个黄酮类化合物。经波谱分析和化学分析鉴定为(9R)-moracin p3′-O-α-l-arabinopyranoside(1)、(9R)-moracin p3′-O-β-d-glucopyranoside(2)、(9R)-moracin p3′-O-β-d-glucopyranoside(3)和(9R)-moracin O 10-O-β-d-glucopyranoside(4)。三种苯并呋喃型二苯胺,moracin O (5), R(7)和P(8)对谷氨酸诱导的SK-N-SH细胞死亡具有显著的神经保护作用。此外,moracin O(5)和P(8)对醋酸引起的疼痛也有显著的抑制作用。与代谢性谷氨酸受体1 (mGluR1)的分子对接结果表明,这些具有神经保护作用的苯并呋喃型二苯胺可能是桑属植物的有效镇痛成分,并通过介导mGluR1通路发挥作用。
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引用次数: 33
Special Issue on Ruthenium Complexes 钌配合物特刊
Pub Date : 2017-02-01 DOI: 10.3390/molecules22020255
I. Dragutan, V. Drǎgutan, A. Demonceau
The organic chemistry of ruthenium has been one of the most vigorously growing research areas over the past decades. Considerable effort has been extended towards the design and application of a broad series of ruthenium complexes, which culminated with the development by Ryoji Noyori (2001 Nobel Prize for Chemistry) of chiral ruthenium catalysts for stereoselective hydrogenation reactions [1], and the discovery by Robert H. Grubbs (2005 Nobel Prize for Chemistry) of well-defined ruthenium- benzylidene catalysts for olefin metathesis [2] [...].
钌的有机化学是近几十年来发展最为活跃的研究领域之一。在设计和应用一系列广泛的钌配合物方面付出了相当大的努力,其中以Ryoji Noyori(2001年诺贝尔化学奖获得者)开发的用于立体选择性加氢反应[1]的手性钌催化剂和Robert H. Grubbs(2005年诺贝尔化学奖获得者)发现的用于烯烃复分解反应[1]的定义明确的钌-苄基催化剂达到高潮[…]。
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引用次数: 6
Towards Precision Engineering of Canonical Polyketide Synthase Domains: Recent Advances and Future Prospects 典型聚酮合酶结构域的精密工程研究进展与展望
Pub Date : 2017-02-01 DOI: 10.3390/molecules22020235
C. Bayly, Vikramaditya G. Yadav
Modular polyketide synthases (mPKSs) build functionalized polymeric chains, some of which have become blockbuster therapeutics. Organized into repeating clusters (modules) of independently-folding domains, these assembly-line-like megasynthases can be engineered by introducing non-native components. However, poor introduction points and incompatible domain combinations can cause both unintended products and dramatically reduced activity. This limits the engineering and combinatorial potential of mPKSs, precluding access to further potential therapeutics. Different regions on a given mPKS domain determine how it interacts both with its substrate and with other domains. Within the assembly line, these interactions are crucial to the proper ordering of reactions and efficient polyketide construction. Achieving control over these domain functions, through precision engineering at key regions, would greatly expand our catalogue of accessible polyketide products. Canonical mPKS domains, given that they are among the most well-characterized, are excellent candidates for such fine-tuning. The current minireview summarizes recent advances in the mechanistic understanding and subsequent precision engineering of canonical mPKS domains, focusing largely on developments in the past year.
模块化聚酮合成酶(mPKSs)构建功能化聚合物链,其中一些已成为重磅治疗药物。组织成独立折叠域的重复簇(模块),这些装配线一样的巨型合酶可以通过引入非本地组件来设计。然而,糟糕的引入点和不兼容的领域组合会导致意想不到的产品和显著减少的活动。这限制了mpks的工程和组合潜力,阻碍了获得进一步的潜在治疗方法。给定mPKS结构域上的不同区域决定了它如何与底物和其他结构域相互作用。在装配线中,这些相互作用对于反应的正确顺序和有效的聚酮构建至关重要。通过在关键区域进行精密工程,实现对这些域功能的控制,将大大扩展我们可获得的聚酮产品目录。考虑到典型的mPKS域是最具特征的,它们是这种微调的极好候选者。当前的迷你综述总结了最近在典型mPKS域的机制理解和随后的精确工程方面的进展,主要集中在过去一年的发展。
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引用次数: 21
Anticancer Activities of C18-, C19-, C20-, and Bis-Diterpenoid Alkaloids Derived from Genus Aconitum 乌头属C18-、C19-、C20-和双二萜类生物碱的抗癌活性研究
Pub Date : 2017-02-01 DOI: 10.3390/molecules22020267
Mengyue Ren, Qingtian Yu, Chunyu Shi, Jia-bo Luo
Cancer is one of the most common lethal diseases, and natural products have been extensively studied as anticancer agents considering their availability, low toxicity, and economic affordability. Plants belonging to the genus Aconitum have been widely used medically in many Asian countries since ancient times. These plants have been proven effective for treating several types of cancer, such as lung, stomach, and liver cancers. The main effective components of Aconitum plants are diterpenoid alkaloids—which are divided into C18-, C19-, C20-, and bis-diterpenoid alkaloids—are reportedly some of the most promising, naturally abundant compounds for treating cancer. This review focuses on the progress of diterpenoid alkaloids with different structures derived from Aconitum plants and some of their derivatives with potential anticancer activities. We hope that this work can serve as a reference for further developing Aconitum diterpenoid alkaloids as anticancer agents.
癌症是最常见的致死性疾病之一,天然产物因其可获得性、低毒性和经济可承受性而被广泛研究作为抗癌剂。乌头属植物自古以来就在许多亚洲国家被广泛用于医学。这些植物已被证明对治疗几种癌症有效,如肺癌、胃癌和肝癌。乌头属植物的主要有效成分是二萜生物碱——分为C18-、C19-、C20-和双二萜生物碱——据报道,它们是最有前途的、天然丰富的治疗癌症的化合物。本文综述了乌头属植物中不同结构的二萜类生物碱及其具有潜在抗癌活性的衍生物研究进展。希望本研究能为进一步开发乌头二萜生物碱作为抗癌药物提供参考。
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引用次数: 24
Characterization of Polysaccharides with Antioxidant and Hepatoprotective Activities from the Edible Mushroom Oudemansiella radicata 食用菌根茎菇多糖抗氧化和保肝活性的研究
Pub Date : 2017-02-01 DOI: 10.3390/molecules22020234
Qin Liu, Mengjuan Zhu, Xueran Geng, Hexiang Wang, T. Ng
The preliminary structure, in vitro antioxidant and in vivo hepatoprotective activities of water-soluble polysaccharides (ORWP) and alkali-soluble polysaccharides (ORAP), prepared from the mushroom Oudemansiella radicata, were investigated. Both ORWP and ORAP were heteropolysaccharides with mannose, glucose and galactose being the main monosaccharide components. Regarding the antioxidant activities, ORWP and ORAP showed effective 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity, hydrogen peroxide scavenging activity and lipid peroxidation inhibitory effects, as well as moderate reducing power and Fe2+ chelating activity. For the hepatoprotective activity, administration of ORWP and ORAP prevented the increase in serum alanine aminotransferase and aspartate aminotransferase activities in a carbon tetrachloride-induced acute liver damage model, suppressed hepatic malondialdehyde formation and stimulated the activities of hepatic superoxide dismutase and glutathione peroxidase. Thus, we speculate that ORWP and ORAP may protect the liver from CCl4-induced hepatic damage via antioxidant mechanisms.
研究了蘑菇根茎水溶性多糖(ORWP)和碱溶多糖(ORAP)的初步结构、体外抗氧化活性和体内保肝活性。ORWP和ORAP均为以甘露糖、葡萄糖和半乳糖为主要单糖组分的杂多糖。在抗氧化活性方面,ORWP和ORAP具有较强的DPPH自由基清除能力、过氧化氢清除能力和抑制脂质过氧化作用,并具有一定的还原能力和螯合Fe2+活性。在肝保护作用方面,ORWP和ORAP可抑制四氯化碳急性肝损伤模型血清丙氨酸转氨酶和天冬氨酸转氨酶活性的升高,抑制肝脏丙二醛的形成,刺激肝脏超氧化物歧化酶和谷胱甘肽过氧化物酶的活性。因此,我们推测ORWP和ORAP可能通过抗氧化机制保护肝脏免受ccl4诱导的肝损伤。
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引用次数: 59
Novel Magnetic Cross-Linked Cellulase Aggregates with a Potential Application in Lignocellulosic Biomass Bioconversion 新型磁性交联纤维素酶聚集体在木质纤维素生物质生物转化中的潜在应用
Pub Date : 2017-02-01 DOI: 10.3390/molecules22020269
Junqi Jia, Weiwei Zhang, Zeng‐Jie Yang, Xian-Ling Yang, Na Wang, Xiao‐Qi Yu
The utilization of renewable biomass resources to produce high-value chemicals by enzymatic processes is beneficial for alternative energy production, due to the accelerating depletion of fossil fuels. As immobilization techniques can improve enzyme stability and reusability, a novel magnetic cross-linked cellulase aggregate has been developed and applied for biomass bioconversion. The cross-linked aggregates could purify and immobilize enzymes in a single operation, and could then be combined with magnetic nanoparticles (MNPs), which provides easy separation of the materials. The immobilized cellulase showed a better activity at a wider temperature range and pH values than that of the free cellulase. After six cycles of consecutive reuse, the immobilized cellulase performed successful magnetic separation and retained 74% of its initial activity when carboxylmethyl cellulose (CMC) was used as the model substrate. Furthermore, the structure and morphology of the immobilized cellulase were studied by Fourier transform infrared spectroscopy (FTIR) and scanning electron microscopy (SEM). Moreover, the immobilized cellulase was shown to hydrolyze bamboo biomass with a yield of 21%, and was re-used in biomass conversion up to four cycles with 38% activity retention, which indicated that the immobilized enzyme has good potential for biomass applications.
由于化石燃料的加速枯竭,利用可再生生物质资源通过酶促过程生产高价值化学品对替代能源生产是有益的。由于固定化技术可以提高酶的稳定性和可重复使用性,一种新型的磁性交联纤维素酶聚合体被开发出来并应用于生物质生物转化。交联聚集体可以在一次操作中纯化和固定酶,然后可以与磁性纳米颗粒(MNPs)结合,从而提供了易于分离的材料。固定化后的纤维素酶在较宽的温度范围和pH值下均表现出较好的活性。以羧甲基纤维素(CMC)为模型底物时,连续重复使用6个循环后,固定化纤维素酶进行了成功的磁分离,并保持了74%的初始活性。利用傅里叶变换红外光谱(FTIR)和扫描电镜(SEM)对固定化纤维素酶的结构和形态进行了研究。此外,固定化纤维素酶水解竹子生物量的产率为21%,可重复利用4次,活性保持率为38%,表明固定化酶具有良好的生物质应用潜力。
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引用次数: 75
Experimental Evidence and In Silico Identification of Tryptophan Decarboxylase in Citrus Genus 柑桔属色氨酸脱羧酶的实验证据和硅晶鉴定
Pub Date : 2017-02-01 DOI: 10.3390/molecules22020272
L. De Masi, D. Castaldo, D. Pignone, L. Servillo, A. Facchiano
Plant tryptophan decarboxylase (TDC) converts tryptophan into tryptamine, precursor of indolealkylamine alkaloids. The recent finding of tryptamine metabolites in Citrus plants leads to hypothesize the existence of TDC activity in this genus. Here, we report for the first time that, in Citrus x limon seedlings, deuterium labeled tryptophan is decarboxylated into tryptamine, from which successively deuterated N,N,N-trimethyltryptamine is formed. These results give an evidence of the occurrence of the TDC activity and the successive methylation pathway of the tryptamine produced from the tryptophan decarboxylation. In addition, with the aim to identify the genetic basis for the presence of TDC, we carried out a sequence similarity search for TDC in the Citrus genomes using as a probe the TDC sequence reported for the plant Catharanthus roseus. We analyzed the genomes of both Citrus clementina and Citrus sinensis, available in public database, and identified putative protein sequences of aromatic l-amino acid decarboxylase. Similarly, 42 aromatic l-amino acid decarboxylase sequences from 23 plant species were extracted from public databases. Potential sequence signatures for functional TDC were then identified. With this research, we propose for the first time a putative protein sequence for TDC in the genus Citrus.
植物色氨酸脱羧酶(TDC)将色氨酸转化为吲哚烷基胺生物碱的前体色胺。最近在柑橘类植物中发现的色胺代谢物导致了该属植物中存在TDC活性的假设。本研究首次报道了在柑橘柠檬幼苗中,氘标记的色氨酸被脱羧为色胺,由色胺依次形成氘化的N,N,N-三甲基色胺。这些结果为TDC活性的发生和色氨酸脱羧产生的色胺的连续甲基化途径提供了证据。此外,为了确定TDC存在的遗传基础,我们以报道的Catharanthus roseus的TDC序列为探针,在柑橘基因组中进行了TDC的序列相似性搜索。我们分析了公共数据库中柑橘和中华柑橘的基因组,并确定了假定的芳香l-氨基酸脱羧酶的蛋白质序列。同样,从公共数据库中提取了23种植物的42个芳香l-氨基酸脱羧酶序列。然后确定功能性TDC的潜在序列特征。通过这项研究,我们首次提出了柑橘属植物TDC的推定蛋白序列。
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引用次数: 12
期刊
Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry
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