Integrated approaches to the configurational assignment of marine natural products

Molinski, Tadeusz F.; Morinaka, Brandon I.

doi:10.1016/j.tet.2011.12.070

Cited by 81 publications

(77 citation statements)

References 365 publications

(218 reference statements)

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“…6,7 As molecules become progressively more proton-deficient, the challenge of assembling a structure increases significantly. The inherent challenge in determining the structure of proton-deficient molecules leads to what is now known among natural products chemists as the so-called Crews Rule, 8 the name derived from a work by Professor Phil Crews and a colleague. 9 In large part, the difficulty in dealing with proton-deficient structures is based on the necessity of being able to access 4 J CH and longer range 1 H-13 C heteronuclear couplings, which cannot be readily carried out with HMBC data even when optimized for small coupling constants, e.g., 3 Hz.…”

Section: Introductionmentioning

confidence: 99%

“…3 J CC Correlations provide structural information equivalent to the sought after 4 J CH coupling information that can be vital in elucidating the structure of proton-deficient molecules that fall under the so-called Crews Rule. 8 The second major point of difference between 1,n-and 1,1-ADEQUATE experiments is that the latter is more sensitive than the former in the same sense that HSQC experiments are more sensitive than HMBC experiments.…”

Section: Introductionmentioning

confidence: 99%

“…The structurally complex alkaloid staurosporine (14) 53 was used as a model compound to further evaluate the utilization of the dual-optimized inverted 1 J CC 1,n-ADEQUATE experiment to extract 3 J CC (equivalent to 4 J CH ) correlations that are often necessary to determine the structure of severely proton-deficient molecules. 8 In DMSO, the resonances of the two aromatic four-spin systems were heavily overlapped but were readily disentangled using a series of IDR-(Inverted Direct Response)-HSQC-total correlation spectroscopy (TOCSY) spectra. 54 The dual optimized inverted 1 J CC 1,n-ADEQUATE spectrum of extremely congested aromatic region of 14 is shown in Figure 13.…”

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confidence: 99%

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Application of 1,n-ADEQUATE and Modified Variants to Structure Elucidation and Spectral Assignment Problems

Martin

Reibarkh

Buevich

et al. 2014

eMagRes

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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confidence: 99%

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Application of 1,n-ADEQUATE and Modified Variants to Structure Elucidation and Spectral Assignment Problems

Martin

Reibarkh

Buevich

et al. 2014

eMagRes

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“…It proves that the marine reservoir holds infinite pharmacologically promising and exciting drug candidates for human health [20][21][22].…”

Section: The Marine Diversitymentioning

confidence: 99%

Marine Carbohydrate Based Therapeutics for Alzheimer Disease-Mini Review

Manig¹,

Ramachandran²,

Saravanan³

2015

J Neurol Neurosci

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Neurological disorders occur due to recognition of neurological repairs and resources are indirectly scarce, especially in low income and developing countries. They are disorders of the central nervous system and common cause of physiological and economic burden worldwide. Alzheimer's disease (AD) and other dementias is one of the progressive neurodegenerative disorders which causes memory loss and cognitive impairment due to aggregation of misfolded proteins and neurofibrillar tangles in brain. The failure of the conventional drugs to decline disease progression accompanied with numerous adverse effects has forced the researchers to look for efficient drug candidates from alternate natural resources. The marine reservoir with its large biodiversity and untapped resource potential holds numerous molecules of biomedical and clinical importance. In this review, we hypothesize the utilization of the sulfated polysaccharides as glycobased mimetics, leading to the prevention of aggregation of plaques and protein tangles. With further screening and validation, the carbohydrates from the marine sources, thus hold immense potentials to function as alternative therapeutic agent against neurological disorders.

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“…A estereoquímica é um importante aspecto da pesquisa de produtos naturais. Recentemente, abordagens integradas para determinação da configuração baseadas em banco de dados de RMN, propriedades opticas, inferências da biossíntese ou bioinformática, cristalografia de raio-X e síntese química tem sido amplamente aplicadas a produtos naturais marinhos (MOLINSKI & MORINAKA, 2012).…”

Section: Abordagens Modernas Da Pesquisa Com Produtos Naturais Marinhosunclassified

Estudo químico de cianobactérias marinhas e do cultivo misto entre a linhagem Geitlerinema sp CENA556 e o fungo Trichoderma atroviride, endófito da alga marinha Bostrychia tenella

Silva¹

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Estudo químico de cianobactérias marinhas e do cultivo misto entre a linhagem Geitlerinema sp CENA556 e o fungoMarine organisms are recognized as a rich reservoir of natural products with exceptional molecular structures. In this context, cyanobacteria and endophytic fungi has emerged as source of promising bioactive compounds. The aim of this work was to look for biologically active compounds from the marine cyanobacteria strains, collected in Ubatuba, coast of the São Paulo state (Brazil), and to explore the biosynthetic potential of the fungus Trichoderma atroviride (endophyte isolated from marine seaweed Bostrychia tenella, collected in the rocky Shore of Praia de Fortaleza, Ubatuba, SP) by coculture with the cyanobacteria strain Geitlerinema sp CENA556. Initially, five species of marine cyanobacteria were isolated from the sample collected at the coast of São Paulo, and then characterized phylogenetically. Among them, the strains coded as Geitlerinema sp CENA552 and Geitlerinema sp CENA556 were cultured in mimicking seawater medium and extracted with a mix of CH 2 Cl 2 / MeOH (2:1), and then EtOAc. The concentrated extract was partitioned into hexane fraction and MeOH/H2O (95: 5) fraction. Four known compounds were identified from the hexane fraction of the Geitlerinema sp CENA552 extract by GC-MS analysis: 2-hexyl-1-decanol, 3-octadecene, neophytadiene, and methyl palmitate. Similarly, the compounds dodecanal, 8-heptadecene, palmitaldehyde, neophytadiene, phytol, methyl palmitoleate, methyl 7-hexadecenoate, and methyl 9-hexadecenoate were identified from the hexane fraction of the Geitlerinema sp CENA556 extract. Starting of MeOH/H2O (95: 5) fraction of Geitlerinema sp CENA556 extract, seven compounds were isolated by semi preparative HPLC-PDA and identified by NMR spectroscopy and HR-MS analysis. Among them, five known nucleosides first isolated from cyanobacteria: 2'-deoxyuridine, thymidine, adenosine, 2'-deoxyadenosine, and uridine. Also two amino acids: D-leucine and L-phenylalanine. Trichoderma atroviride was grown alone in rice and Czapeck media and the coculture between the fungus and the cyanobacteria (Geitlerinema sp CENA556) were performed using the same media. The CH 2 Cl 2 / MeOH (2:1) and EtOAc pooled extract from the coculture of the fungus T. atroviride and the cyanobacteria Gleiterinema sp CENA556 in Czapek medium shows significant difference in the metabolites production when compared to individually cultured fungus and cyanobacteria. Four catechol type siderophores were isolated from MeOH/H2O (95: 5) fraction of this extract: agrobactin, agrobactin A, photobactin and one novel compound. Agrobactin, the major compound, showed substantial antibacterial activity against P. mirabilis, E. coli, S. saprophyticus, S. aureus and P. aeruginosa. Thus, the studied brazilian cyanobacteria Geitlerinema sp appeared to be promising for isolation of nucleosides with biological activity. Furthermore, the fungus T. atroviride proved to be a prolific source of antibacterial siderophores obtained by biologic...

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Integrated approaches to the configurational assignment of marine natural products

Cited by 81 publications

References 365 publications

Application of 1,n-ADEQUATE and Modified Variants to Structure Elucidation and Spectral Assignment Problems

Application of 1,n-ADEQUATE and Modified Variants to Structure Elucidation and Spectral Assignment Problems

Marine Carbohydrate Based Therapeutics for Alzheimer Disease-Mini Review

Estudo químico de cianobactérias marinhas e do cultivo misto entre a linhagem Geitlerinema sp CENA556 e o fungo Trichoderma atroviride, endófito da alga marinha Bostrychia tenella

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