[PMID]: | 28647482 |
[Au] Autor: | Simmler C; Lankin DC; Nikolic D; van Breemen RB; Pauli GF |
[Ad] Endereço: | UIC/NIH Center for Botanical Dietary Supplements Research, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, College of Pharmacy, 833 S. Wood Street, Chicago, IL 60612, USA. Electronic address: simmler@uic.edu. |
[Ti] Título: | Isolation and structural characterization of dihydrobenzofuran congeners of licochalcone A. |
[So] Source: | Fitoterapia;121:6-15, 2017 Sep. |
[Is] ISSN: | 1873-6971 |
[Cp] País de publicação: | Netherlands |
[La] Idioma: | eng |
[Ab] Resumo: | In an effort to explore the residual complexity of naturally occurring chalcones from the roots of Glycyrrhiza inflata (Fabaceae), two new licochalcone A (LicA) derivatives were isolated as trace metabolites from enriched fractions. Both constituents contain a dihydrofuran moiety linked to carbons C-4 and C-5 of the retrochalcone core. Compound 1 (LicAF1) represents a new chemical entity, whereas compound 2 (LicAF2) has previously been reported as a Lewis acid catalyzed rearrangement of LicA. Evaluation of chirality revealed that both dihydrofuran derivatives existed as a mixture of R and S enantiomers. Interestingly, when solutions were exposed to sunlight, both dihydrofuran retrochalcones, initially isolated as trans isomers, were found to rapidly isomerize yielding trans and cis isomers. Analysis of the 1D H NMR spectra of the photolysis products revealed the presence of two sets of proton resonances ascribed to each of the geometric isomers. An up-field shift of all proton resonances arising from the cis isomer was observed, suggesting that anisotropic shielding effects were introduced through an overall perturbation of the 3-dimensional structure upon photoisomerization. Similar up-field shifts were observed in the C spectrum of the cis isomer, except for the CO, C-α, and C-6 carbons, which experienced downfield shifts. Analogous NMR results were observed for LicA. Hence, the results presented herein encompass the isolation and full characterization of LicAF analogs 1 and 2, and observations of their trans-to-cis photoisomerization through the systematic analysis of their NMR spectra. |
[Mh] Termos MeSH primário: |
Amidinas/química Benzofuranos/química Chalconas/química Glycyrrhiza/química
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[Mh] Termos MeSH secundário: |
Amidinas/isolamento & purificação Benzofuranos/isolamento & purificação Chalconas/isolamento & purificação Estrutura Molecular Extratos Vegetais/química Raízes de Plantas/química Espectroscopia de Prótons por Ressonância Magnética Estereoisomerismo
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[Pt] Tipo de publicação: | JOURNAL ARTICLE |
[Nm] Nome de substância:
| 0 (Amidines); 0 (Benzofurans); 0 (Chalcones); 0 (Plant Extracts); 0 (benzofuran-2-carboxamidine); JTV5467968 (licochalcone A) |
[Em] Mês de entrada: | 1710 |
[Cu] Atualização por classe: | 171116 |
[Lr] Data última revisão:
| 171116 |
[Sb] Subgrupo de revista: | IM |
[Da] Data de entrada para processamento: | 170626 |
[St] Status: | MEDLINE |
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