Determination of the Absolute Configuration of a Flavanone Isolated from a Madagascar Plant

Su, Qingxi; Harinantenaina, Liva; Brodie, PJ; Callmander, MW; Rakotondrajaona, Roland; Rakotobe, Etienne; Rasamison, VE; Kingston, Dgi

doi:10.1055/s-0033-1348723

Cited by 4 publications

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…According to previous study, the absolute configuration of flavanones was defined by utilization of CD spectrum in conjunction with NMR spectroscopic data. [ 18 ] In the 1 H‐NMR spectra of 5,7,2'‐trihydroxyflavanone the signals of the H2 proton; and the diastereotopic H3ax and H3eq protons appeared at 5.80 ppm, 3.08, and 2.84 ppm as three doublets of doublets, respectively. The value of the coupling constant between H2 and H3ax was so large (J 2,3ax = 17.0 Hz) which can only arise from a trans‐diaxial coupling, thus H2 was axial, and the 2‐phenyl group had equatorial orientation.…”

Section: Resultsmentioning

confidence: 99%

Evaluating the enantioselective capability of a cellulose tris(3,5‐dimethylphenyl carbamate)‐based stationary phase towards 5,7,2'‐trihydroxyflavanone

Hung,

Thanh,

Luyen

et al. 2023

Vietnam Journal of Chemistry

View full text Add to dashboard Cite

In this study, an evaluation of the enantioselective of a chiral flavanone with 2'‐OH substitution (5,7,2'‐trihydroxyflavanone) on ring C was studied by high performance liquid chromatography using the cellulose tris(3,5‐dimethylphenyl carbamate)‐based stationary phase with n‐hexane and iso‐propanol doped with 0.1% (v/v) trifluoroacetic acid as a mobile phase. Column temperature and mobile phase composition were investigated in the assessment of the chiral separation by considering the enantiomeric resolution factor (Rs). Also, the absolute configurations of single enantiomers were determined by measuring CD spectra based on the exciton‐coupling method. The results pointed out that the 2'‐hydroxy group was capable of advancing the enantioselective of flavanones on the cellulose tris(3,5‐dimethylphenyl carbamate)‐based stationary phase when the column temperature was higher than 30 oC and the mobile phase was of 10% iso‐propanol doped with 0.1% (v/v) TFA in n‐hexane. The absolute configuration determination showed that the enantiomer with the 2S configuration was the first eluted and, consequently, the elution order of the enantiomers of 5,7,2'‐trihydroxyflavanone at optimal conditions was in contrast to 5,7,4'‐trihydroxyflavanone and 5,7‐dihydroxyflavanone. The 2'‐OH substitution on the phenyl moiety appears to be capable of inducing or altering the strength of inter‐and intramolecular interactions when the chiral selectors are immobilized on the silica stationary phase.

show abstract

Section: Resultsmentioning

confidence: 99%

Evaluating the enantioselective capability of a cellulose tris(3,5‐dimethylphenyl carbamate)‐based stationary phase towards 5,7,2'‐trihydroxyflavanone

Hung,

Thanh,

Luyen

et al. 2023

Vietnam Journal of Chemistry

View full text Add to dashboard Cite

show abstract

New Phenanthrenoid Dimer Derivative and Anti-Inflammatory Constituents from Juncus effusus var. decipiens

Chen,

Huang,

Chu

et al. 2024

Chem Nat Compd

View full text Add to dashboard Cite

Family Juncaceae: promising source of biologically active natural phenanthrenes

et al. 2018

View full text Add to dashboard Cite

Phenanthrenes represent a relatively small group of aromatic secondary metabolites, which can be divided into three main subgroups (mono-, di-, and triphenanthrenes). Phenanthrenes are reported as an intensively researched field in phytochemistry according to their structural diversity and promising biological activities. Because of their limited occurrence phenanthrenes are considered to be as important taxonomic markers. Juncaceae is a relatively large plant family divided into seven genera of which Juncus and Luzula are the most important ones from phytochemical and pharmacological points of view. To date, almost one hundred natural phenanthrenes have been isolated but only from eight (Juncus acutus, J. effusus, J. inflexus, J. maritimus, J. roemerianus, J. setchuensis, J. subulatus, and Luzula luzuloides) Juncaceae species, including mono-, and diphenanthrenes, and phenanthrene glucosides. Great deal of the isolated compounds are substituted with a vinyl group. This substitution is characteristic exclusively to Juncaceae species. Juncusol (2) was isolated from every investigated species. The richest source of phenanthrenes, as well as the most extensively investigated species is J. effusus. Several isolated compounds possessed different biological activities, e.g.antiproliferative, antimicrobial, anti-inflammatory, antioxidant, spasmolytic, anxiolytic, and antialgal effects. Among them, dehydroeffusol (60) is the most promising one, as it showed antimicrobial, anxiolytic, sedative, spasmolytic, cellular protective and antiproliferative activities. The aim of this review is to summarize the occurrence of phenanthrenes in the family Juncaceae, and give a comprehensive overview of their isolation, structural characteristics and biological activities.

show abstract

Determination of the Absolute Configuration of a Flavanone Isolated from a Madagascar Plant

Cited by 4 publications

References 0 publications

Evaluating the enantioselective capability of a cellulose tris(3,5‐dimethylphenyl carbamate)‐based stationary phase towards 5,7,2'‐trihydroxyflavanone

Evaluating the enantioselective capability of a cellulose tris(3,5‐dimethylphenyl carbamate)‐based stationary phase towards 5,7,2'‐trihydroxyflavanone

New Phenanthrenoid Dimer Derivative and Anti-Inflammatory Constituents from Juncus effusus var. decipiens

Family Juncaceae: promising source of biologically active natural phenanthrenes

Contact Info

Product

Resources

About