Isolation, X-ray crystal structure and theoretical calculations of the new compound 8-Eepicordatin and identification of others terpenes and steroids from the bark and leaves of Croton palanostigma Klotzsch

Brasil, Davi do Socorro Barros; Müller, Adolfo Henrique; Guilhon, Giselle Maria Skelding Pinheiro; Alves, Cláudio Nahum; Peris, Gabriel; Llusar, Rosa; Moliner, Vicent

doi:10.1590/s0103-50532010000400021

Cited by 11 publications

(6 citation statements)

References 12 publications

(27 reference statements)

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“…The differences in the data may be caused by the fact that most optimizations were obtained under the gas phase conditions, and the difference in the base group and method used for calculation could be neglected. Therefore, this manifested the veracity of the theoretical method 33,34 . Meanwhile, we could know that 1 had no intramolecular hydrogen bonds.…”

Section: Resultsmentioning

confidence: 94%

Potential chiral fluorescent molecular probes based on an α,β-unsaturated ketone for anion detection

Liu

Pan

et al. 2019

Sci Rep

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A series of potential chiral compounds containing an α,β-unsaturated ketone was developed for anion detection. The interplay of compounds and biological momentous anions (Cl−, H2PO4−, I−, AcO−, HS−, F−, and Br−) was evaluated by UV-vis experiments, fluorescence experiments, and electrochemical tests. By comparison, compound 1 had the best selectivity and compound 5 had the strongest binding ability among the five compounds. And compound 5 had the highest sensitivity to H2PO4− among the measured anions, and it also can be applied to actual samples, the content of H2PO4− tested in the potassium dihydrogen phosphate fertilizer solution reached above 97.5% of the marked content, and the recovery rates were within the range of 98.5–99.1%, attesting that this method was reliable for the test of H2PO4− in fertilizer. Through HRMS titration, circular dichroism and optical rotation experiments, the probable interacted mechanism was proved that the interaction site was the C=C of the α,β-unsaturated ketone structure. In addition, the interacted mechanism was researched from the perspective of chirality. Furthermore, theoretical investigation analysis was introduced to reveal that the roles of molecular frontier orbitals in molecular interplay were determined. Therefore, this series of potential chiral compounds has potential application prospects in anion recognition.

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Section: Resultsmentioning

confidence: 94%

Potential chiral fluorescent molecular probes based on an α,β-unsaturated ketone for anion detection

Liu

Pan

et al. 2019

Sci Rep

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“…The computational simulation of the 1 H-NMR spectra allowed the identification of the non-equivalent hydrogens presenting theoretical values relatively close to the experimental ones, as shown in Table II, which corroborates with works of the literature that used computational simulation to define Hα and Hβ protons of diterpenes that were not elucidated experimentally. 6,9…”

Section: Resultsmentioning

confidence: 99%

“…Papers are found in the literature comparing the experimental data of NMR with theoretical calculations, achieving accurate and satisfactory results. [3][4][5][6][7][8][9][10][11] The DFT methodology could be applied as a promising alternative in support of traditional NMR experimental techniques.…”

Section: Introductionmentioning

confidence: 99%

Theoretical study via DFT for prediction of 13C and 1H NMR data of two diterpenoids derived from the root of salvia grandifolia

Costa

Silva

et al. 2019

JSCS

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The DFT method has become a promising alternative in the support of traditional NMR experimental techniques, comparing experimental data with theoretical data, thereby achieving accurate and satisfactory results. In the present study, the experimental data of two diterpenes were compared to the theoretical data obtained by the GIAO method, applying DFT at the B3LYP/cc-pVDZ and B3PW91/DGDZVP levels to verify the degree of correlation, significance and predictability of the models obtained with the purpose of proving which of the computational methods is the most efficient for this class of substances. The theoretical NMR values obtained at B3LYP/cc-pVDZ were the more satisfactory, showing better linear correlations, presenting greater degrees of adjustments, significance and predictability compared to the B3PW91/DGDZVP method. Thus, these values were used to define H α and H β 1, 2, 3, 6 and 7 for diterpene 1 and 1, 2, 3, 6 and 7 for diterpene 2, which was not possible using experimental data. This showed that the quantum method used could help in the structural elucidation of natural products.

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“…Our research group has published several papers describing studies and structural identification of aparisthman and cordatin involving analysis of NMR, infrared and mass spectrometry. [ 4 5 10 11 12 ]…”

Section: Methodsmentioning

confidence: 99%

Biological activities of Croton palanostigma Klotzsch

et al. 2015

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Background:Different species of Croton are used in traditional Amazonian medicine. Among the popular uses are treatment of bacterial diseases, poorly healing wounds and fevers.Objective:This study evaluated the antileishmanial, antiplasmodial and antimicrobial activities of the extracts and diterpenes of Croton palanostigma Klotzsch (Euphorbiaceae).Materials and Methods:Leaves and bark were extracted with dichloromethane and methanol. The bark dichloromethane extract (BDE) was chromatographed on a column, obtaining cordatin and aparisthman. The extracts and diterpenes were assayed thought agar disk diffusion method and their bactericidal or fungicidal effects were evaluated by minimum bactericidal or fungicidal concentration. The antiplasmodial activity was evaluated after 24 and 72 h of exposition. The antileishmanial activity was performed on promastigotes forms of Leishmania amazonensis.Results:The bark methanol extract (BME) and cordatin were not active against any microbial strains tested; BDE and leaves methanol extract (LME) were positive for Pseudomonas aeruginosa and aparisthman was positive for Candida albicans. In the determination of the minimum bactericidal concentration, neither of them were active in the highest concentration tested. The extracts and diterpenes were inactive in Plasmodium falciparum, except the LME in 72 h. Any extract was shown to be active in promastigote forms of L. amazonensis.Conclusion:These results indicate that the BDE and LME did not inhibit the bacterial growth, then they probably had bacteriostatic effect. LME presented activity in P. falciparum.

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Isolation, X-ray crystal structure and theoretical calculations of the new compound 8-Eepicordatin and identification of others terpenes and steroids from the bark and leaves of Croton palanostigma Klotzsch

Cited by 11 publications

References 12 publications

Potential chiral fluorescent molecular probes based on an α,β-unsaturated ketone for anion detection

Potential chiral fluorescent molecular probes based on an α,β-unsaturated ketone for anion detection

Theoretical study via DFT for prediction of 13C and 1H NMR data of two diterpenoids derived from the root of salvia grandifolia

Biological activities of Croton palanostigma Klotzsch

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