Infrared spectral evidence and DFT calculations of hydrogen-bonding and molecular structures of acetogenins

Afonso, Sabrina; Silva, Fabiano B.; Silva, Arnaldo F.; Scarmínio, Ieda Spacino; Bruns, Roy E.

doi:10.1016/j.molstruc.2016.10.007

Cited by 5 publications

(2 citation statements)

References 21 publications

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“…Finally, it has to be underlined that annopurpuricins A-D ( 1 – 4 ) had a relative configuration trans / threo between both THF rings, similar to bullatacin, an acetogenin characterized by notable antiproliferative activity [10,11]. Moreover, the molecular model of annopurpuricin A (Figure 3) highlighted structural attributes in agreement with a recent theoretical study which correlates very strong O-H stretching intensities, characteristic of hydrogen bonding, with bent V -type equilibrium geometry structures [41]. Furthermore, comparisons of the 3D-structures of highly bioactive acetogenins seem to indicate that this special feature could improve the interactions with the target.…”

Section: Resultssupporting

confidence: 84%

Cytotoxic Acetogenins from the Roots of Annona purpurea

Hernandez-Fuentes

García-Argáez

Peraza-Campos

et al. 2019

IJMS

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Annona purpurea, known in Mexico as “cabeza de negro” or “ilama”, belongs to the Annonaceae family. Its roots are employed in folk medicine in several regions of Mexico. Taking that information into account, a chemical and biological analysis of the components present in the roots of this species was proposed. Our results demonstrated that the dichloromethane (DCM) extract was exclusively constituted by a mixture of five new acetogenins named annopurpuricins A–E (1–5). These compounds have an aliphatic chain of 37 carbons with a terminal α,β unsaturated γ-lactone. Compounds 1 and 2 belong to the adjacent bis-THF (tetrahydrofuran) α-monohydroxylated type, while compounds 3 and 4 belong to the adjacent bis-THF α,α’-dihydroxylated type; only compound 5 possesses a bis-epoxide system. Complete structure analysis was carried out by spectroscopy and chemical methods. All compounds were evaluated for their antiproliferative activity on three human tumor cell lines (MSTO-211H, HeLa and HepG2). Compounds 1–4 inhibited significantly the growth of HeLa and HepG2 cells, showing GI50 values in the low/subnanomolar range, while 5 was completely ineffective under the tested conditions. The investigation of the mechanism of action responsible for cytotoxicity revealed for the most interesting compound 1 the ability to block the complex I activity on isolated rat liver mitochondria (RLM).

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Section: Resultssupporting

confidence: 84%

Cytotoxic Acetogenins from the Roots of Annona purpurea

Hernandez-Fuentes

García-Argáez

Peraza-Campos

et al. 2019

IJMS

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“…Compared with the summer, the winter shows higher intensity bands near 1740-1770 cm -1 that are of interest for the identification of acetogenin compounds because they are related to carboxylic ester groups or fatty acid esters and the γ-lactone. 41,42 Most characteristic bands associated with acetogenins are found, such as those for fatty and amino acids detected between 1500-1200 cm -1 , monoterpenes detected at 840 cm -1 and the carbonyl group found in aldehydes, ketones, acids, esters and amides with absorption between 1650 and 1850 cm -1 . Compared with the summer, the spring extracts show higher levels of glucose and fructose (1060 and 1031 cm -1 , respectively).…”

Section: Resultsmentioning

confidence: 99%

Influence of Seasonality and Sunlight Effects on Rollinia mucosa Leaves Fingerprint

Afonso¹,

Silva²,

Marcheafave³

et al. 2018

J. Braz. Chem. Soc.

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Rollinia mucosa fruit has generated great interest due to the presence of bioactive compounds, which exhibit promising biological activities. Fingerprinting analytical techniques, chromatographic-diode array detection (DAD), infrared, mass spectrometric, 1 H and 13 C nuclear magnetic resonance (NMR) spectra, associated with chemometric analysis and mixture design, were used to determine chemical discriminations of sun-exposed and self-shaded leaves of Rollinia mucosa in each of the four seasons. Sunlit leaves in winter presented higher metabolite signals related to the acetogenins, whereas shaded leaves have higher abundances of carbohydrates and terpenes. Sunlit leaves harvested in the summer had the smallest metabolite abundances. Fingerprints confirmed the presence of two acetogenins, annonacin A and annonastatin. Ternary and quaternary mixtures of the statistical mixture design were most effective for revealing important discriminations.

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