Novel Synthetic Methodologies. Part 2. Vicarious Nucleophilic Substitution in Enamine Derivatives of 1‐Hydroxynaphthalene‐2,4‐dicarbaldehyde.

Sashidhara, Koneni V.; Rosaiah, Jammikuntla N.

doi:10.1002/chin.200732095

Cited by 6 publications

(12 citation statements)

References 1 publication

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“…No entanto, só os analitos que absorvem na região UV/Visível são detectados. Já o uso da NMR vem crescendo exponencialmente nos últimos anos devido a sua robustez e alta sensibilidade na quantificação dos núcleos orgânicos ativos mais populosos: 1 H, 13 C, 15 N, 31 P. Seu uso pode ser feito a partir de hifenação com LC em fluxo contínuo (on-flow) para determinação dos constituintes majoritários, ou por coleta de frações em micro colunas de extração de fase sólida (SPE) permitindo a realização de espectros bidimensionais (off-line) e a detecção dos compostos minoritários. Além disto, por meio do uso de sequências de pulso adequadas, é possível a detecção in situ de compostos conhecidos por meio da obtenção de espectros de NMR de moléculas individuais em mistura sem haver a necessidade de separação.…”

Section: Discussionunclassified

“…Até recentemente, muitos métodos de fracionamento e purificação de produtos naturais presentes num extrato constituído por centenas de substâncias, além de pouco sensíveis, frequentemente resultavam em substâncias já conhecidas, presentes em várias espécies ou gêneros. 13 Estima-se que são necessários cerca de US$ 50,000 e de três meses de trabalho para isolar e identificar um composto inédito ativo a partir de uma espécie ou de um organismo. 14 Portanto, métodos analíticos avançados capazes de mapear e identificar substâncias bioativas novas em quantidades mínimas de extrato, sem a necessidade de fracionamento e isolamento trabalhosos e custosos, são extremamente importantes desde o início da pesquisa de biodescoberta.…”

Section: Introductionunclassified

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Metabolômica, uma abordagem otimizada para exploração da biodiversidade brasileira: estado da arte, perspectivas e desafios

Funari¹,

Castro‐Gamboa²,

Cavalheiro³

et al. 2013

Quím. Nova

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Recebido em 9/9/13; aceito em 8/10/13; publicado na web em 24/10/13 METABOLOMICS, AN OPTIMIZED APPROACH FOR THE RATIONAL EXPLOITATION OF BRAZILIAN BIODIVERSITY: STATE OF THE ART, NEW SCENARIOS, AND CHALLENGES. Brazilian biodiversity is a colossal source of secondary metabolites with remarkable structural features, which are valuable in further biodiscovery studies. In order to fully understand the relations and interactions of a living system with its surroundings, efforts in natural product chemistry are directed toward the challenge of detecting and identifying all the molecular components present in complex samples. It is plausible that this endeavor was born out of recent technological sophistication in secondary metabolite identification with sensitive spectroscopic instruments (MS and NMR) and higher resolving power of chromatographic systems, which allow a decrease in the amount of required sample and time to acquire data. Nevertheless, the escalation of data acquired in these analyses must be sorted with statistical and multi-way tools in order to select key information. Chromatography is also of paramount importance, more so when selected compounds need to be isolated for further investigation. However, in the course of pursuing a "greener" environment, new policies, with an aim to decrease the use of energy and solvents, are being developed and incorporated into analytical methods. Metabolomics could be an effective tool to answer questions on how living organisms in our huge biodiversity work and interact with their surroundings while also being strategic to the development of high value bio-derived products, such as phytotherapeutics and nutraceuticals. The incorporation of proper phytotherapeutics in the so-called Brazilian Unified Health System is considered an important factor for the urgent improvement and expansion of the Brazilian national health system. Furthermore, this approach could have a positive impact on the international interest toward scientific research developed in Brazil as well as the development of high value bio-derived products, which appear as an interesting economic opportunity in national and global markets. Thus, this study attempts to highlight the recent advances in analytical tools used in detection of secondary metabolites, which can be useful as bioproducts. It also emphasizes the potential avenues to be explored in Brazilian biodiversity, known for its rich chemical diversity.

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Section: Discussionunclassified

Section: Introductionunclassified

Metabolômica, uma abordagem otimizada para exploração da biodiversidade brasileira: estado da arte, perspectivas e desafios

Funari¹,

Castro‐Gamboa²,

Cavalheiro³

et al. 2013

Quím. Nova

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“…A vast number of reviews describing the enhanced technological progress of hyphenated tools and combined dereplication strategies that have been pivotal to accelerate the speed of novel NPs isolation process have been reported. [3][4][5][6][7] Others particularly debate the emerging advances in chromatography, mass spectrometry (MS) and NMR technologies to overcome the challenges encountered in screening NPs libraries, increasing the role of NPs in high-throughput screening (HTS) based drug discovery. [8][9][10][11] The approaches used in biodiversity-and taxonomy-guided microbial NPs library construction, combined with HTS and with Liquid Chromatography-Mass Spectrometry (LC-MS) have been promoted as efficient dereplication processes.…”

Section: Reviewsmentioning

confidence: 99%

“…HPLC-DAD-SPE-NMR, LC-MS-ELSD), 68 and exhaustive detailed descriptions have been reported. 4,6,[69][70][71][72][73][74][75][76][77][78][79][80][81][82][83] The introduction of X-hitting algorithm, 84 capillary scale NMR probes, 85 MALDI-TOF imaging, [86][87][88] advanced public and commercial database availability (e.g. Dictionary NPs, Antibase, MarinLit, AntiMarin, Pubchem, ZINC, NAPROC-13, NMRShiDB, GNPS), 12,89-95 de novo sequencing techniques, 96 in silico dereplication, 24 computer assisted numerical analysis, 97,98 bioinformatics, 24,29 genomics, 99 proteomics, 80 metabolomics have all been reported.…”

Section: Dereplication Trends and Approachesmentioning

confidence: 99%

Dereplication: racing to speed up the natural products discovery process

2015

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Covering: 1993-2014 (July)To alleviate the dereplication holdup, which is a major bottleneck in natural products discovery, scientists have been conducting their research efforts to add tools to their "bag of tricks" aiming to achieve faster, more accurate and efficient ways to accelerate the pace of the drug discovery process. Consequently dereplication has become a hot topic presenting a huge publication boom since 2012, blending multidisciplinary fields in new ways that provide important conceptual and/or methodological advances, opening up pioneering research prospects in this field.

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“…Various methods of early stage dereplication have been proposed. 5 Recently, one of our laboratories has developed a rapid method to identify novel compounds from actinomycetes using HPLC-HRMS-based metabolomics. 6 The method relies on careful processing of bacterial extracts and principal component analysis (PCA) of preprocessed LC-MS traces ( Supporting Information ).…”

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confidence: 99%

Microtermolides A and B from Termite-Associated Streptomyces sp. and Structural Revision of Vinylamycin

et al. 2012

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Microtermolides A (1) and B (2) were isolated from a Streptomyces sp. strain associated with fungus-growing termites. The structures of 1 and 2 were determined by 1D- and 2D-NMR spectroscopy and high-resolution mass spectrometry. Structural elucidation of 1 led to the re-examination of the structure originally proposed for vinylamycin (3). Based on a comparison of predicted and experimental 1H and 13C NMR chemical shifts, we propose that vinylamycin’s structure be revised from 3 to 4.

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Novel Synthetic Methodologies. Part 2. Vicarious Nucleophilic Substitution in Enamine Derivatives of 1‐Hydroxynaphthalene‐2,4‐dicarbaldehyde.

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cited by 6 publications

References 1 publication

Metabolômica, uma abordagem otimizada para exploração da biodiversidade brasileira: estado da arte, perspectivas e desafios

Metabolômica, uma abordagem otimizada para exploração da biodiversidade brasileira: estado da arte, perspectivas e desafios

Dereplication: racing to speed up the natural products discovery process

Microtermolides A and B from Termite-Associated Streptomyces sp. and Structural Revision of Vinylamycin

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