Experimental and NMR Theoretical Methodology Applied to Geometric Analysis of the Bioactive Clerodane<i>trans</i>-Dehydrocrotonin

Soares, Breno Almeida; Firme, Caio Lima; Maciel, Maria Aparecida Medeiros; Kaiser, Carlos R.; Schilling, Eduardo; Bortoluzzi, Adaı́lton J.

doi:10.5935/0103-5053.20140010

Cited by 5 publications

(7 citation statements)

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“…Notably, the bioactive type V 19- nor -clerodane-type diterpenoid trans -dehydrocrotonin ( 1076 ), with a cyclohexenone decalin ring A, is one of the most investigated clerodanes in the current literature. 389 Two of the three hydroxy groups in syspiresin A ( 1078 ) from T. chamaedrys are replaced by hydrogen (C-2) and a methoxy group (C-6) in teupolin IX ( 1079 ) from T. polium . 92,277 Crotoeurin A ( 1084 ) from C. euryphyllus was the first nor -clerodane diterpenoid dimer connected through a unique cyclobutane ring via a [2 + 2] cycloaddition; its structure was confirmed by single-crystal X-ray diffraction analysis.…”

Section: Structure Classifications and Sources Of Clerodane Diterpmentioning

confidence: 99%

Clerodane diterpenes: sources, structures, and biological activities

2016

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The clerodane diterpenoids are a widespread class of secondary metabolites and have been found in several hundreds of plant species from various families and in organisms from other taxonomic groups. These substances have attracted interest in recent years due to their notable biological activities, particularly insect antifeedant properties. In addition, the major active clerodanes of Salvia divinorum can be used as novel opioid receptor probes, allowing greater insight into opioid receptor-mediated phenomena, as well as opening additional areas for chemical investigation. This article provides extensive coverage of naturally occurring clerodane diterpenes discovered from 1990 until 2015, and follows up on the 1992 review by Merritt and Ley in this same journal. The distribution, chemotaxonomic significance, chemical structures, and biological activities of clerodane diterpenes are summarized. In the cases where sufficient information is available, structure activity relationship (SAR) correlations and mode of action of active clerodanes have been presented.

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Section: Structure Classifications and Sources Of Clerodane Diterpmentioning

confidence: 99%

Clerodane diterpenes: sources, structures, and biological activities

2016

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“…The analysis of 1 H NMR showed major amount for t-CTN-a-OL, in a 2.81(a-OH):1(b-OH) proportion. NMR theoretical protocol previously developed for structural analyses of organic molecules confirmed structures assignments [12].…”

Section: Introductionmentioning

confidence: 80%

“…In a previous work, we investigated the magnetic, electronic and geometrical properties of the bioactive clerodane t-DCTN by means of a theoretical-experimental comparative analysis, in order to give full support for the NMR characterization of natural products [12]. In this work we studied the NMR chemical shifts and coupling constants for the new semi-synthetic t-CTN, t-CTN-b-OL and t-CTNa-OL compounds by applying the same previously developed protocol.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, NMR data and theoretical study of semi-synthetic derivatives from trans-dehydrocrotonin

Soares

Maciel

Castro

et al. 2016

Journal of Molecular Structure

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“…Through the rise of reliable quantum chemical computational methods, such as Density Functional Theory (DFT), the DFT-NMR spectra of different organic compounds have been extensively reported. A comparison between the experimental and theoretical spectra in most cases reveals that they show the same profile [17][18][19]. Figures S1B and S2B show the theoretical DFT spectra ( 1 H-and 13 C-NMR) for the compound 7 and Table S1 compares the δexp and δcalc values (experimental and theoretical, respectively).…”

Section: Organic Synthesis and Structure Determinationmentioning

confidence: 87%

2-Chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]styryl}pyrimidine: Synthesis, Spectroscopic and Computational Evaluation

Chaves

Sueth-Santiago

Pinto

et al. 2021

Molbank

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A novel curcumin analog namely 2-chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]-styryl}pyrimidine (compound 7) was synthesized by three-step reaction. The condensation reaction of protected vanillin with 2-chloro-4,6-dimethylpyrimidine (6) was the most efficient step, resulting in a total yield of 72%. The characterization of compound 7 was performed by 1H and 13C nuclear magnetic resonance (NMR), as well as high-resolution mass spectrometry. The experimental spectrometric data were compared with the theoretical spectra obtained by the density functional theory (DFT) method, showing a perfect match between them. UV-visible spectroscopy and steady-state fluorescence emission studies were performed for compound 7 in solvents of different polarities and the results were correlated with DFT calculations. Compound 7 showed a solvatochromism effect presenting higher molar extinction coefficient (log ε = 4.57) and fluorescence quantum yield (ϕ = 0.38) in toluene than in acetonitrile or methanol. The simulation of both frontier molecular orbitals (FMOs) and molecular electrostatic potential (MEP) suggested that the experimental spectra profile in toluene was not interfered by a possible charge transfer. These results are an indication of a low probability of compound 7 in reacting with unsaturated phospholipids in future applications as a fluorescent dye in biological systems.

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Experimental and NMR Theoretical Methodology Applied to Geometric Analysis of the Bioactive Clerodanetrans-Dehydrocrotonin

Cited by 5 publications

References 1 publication

Clerodane diterpenes: sources, structures, and biological activities

Clerodane diterpenes: sources, structures, and biological activities

Synthesis, NMR data and theoretical study of semi-synthetic derivatives from trans-dehydrocrotonin

2-Chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]styryl}pyrimidine: Synthesis, Spectroscopic and Computational Evaluation

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