Abstract:A new neolignan glycoside (1) and four known aromatic compounds (2-5) were isolated from the roots of Vetiveria zizanioides. The structure of compound 1 was determined based on spectroscopic analysis and hydrolysis. The structure of known flavonoid glycoside 3 was confirmed by X-ray crystallography. Compound 5 showed weak cytotoxic activity against HL-60 cells with an IC 50 value of 13.1 ± 0.04 M.
“…The conformational preferences of glycosides are analyzed qualitatively as exo /non- exo and anti / gauche , or quantitatively by measuring the φ and ψ dihedral angles . The φ and ψ dihedral angles were defined by φ = C1″–X–C n –C n –1 and ψ = C n –X–C1″–C2″ (Figure b). , Seven flavonoids that have crystal structures were selected, quercitrin, isorhamnetin-3- O -glucoside, eupatolitin-3- O -glucoside, icariin, diosmin, tricin-5- O -glucoside, and apigenin-5- O -neohesperidoside (Figures c and S1). The crystal structures were obtained from the Cambridge Crystallographic Data Center (CCDC) .…”
Many glycosylated natural products display biological
activity
and are deglycosylated by the metabolic processes of the body. Although
unnatural CF2-glycosides have been proposed as nonhydrolyzable
analogues, CF2-derivatives of natural products are exceedingly
challenging to synthesize and few examples exist. These difluorinated
molecules may have unique conformational behavior as a consequence
of changing the glycosidic linkage. In this study, we performed conformational
searches using MacroModel followed by molecular dynamics simulations
to investigate the conformational behavior of the glycosidic bonds
in flavonoid-O-glycosides and in corresponding CF2-glycosylated derivatives. Compared to their O-glycosylated analogues, flavonoid-3-CF2-glycosides and
flavonoid-5-CF2-glycosides showed conformational bias,
whereas flavonoid-7-CF2-glycosides showed more flexibility.
Flavonoid-5-CF2-glycosides were the least flexible compared
to all others. Our results show that the site of the glycosylation
and the substitution pattern on the flavonoid determine the conformational
properties of these molecules. These two factors influence the steric
destabilization and/or stereoelectronic stabilization which govern
the conformational behavior of the flavonoid glycosides. Moreover,
a docking study of quercitrin and its CF2-analogue into
murine ribosomal kinase RSK2 demonstrated the potential for flavonoid-CF2-glycosides to retain a similar binding pose as the parent O-glycoside. These findings will assist in designing stable
flavonoid-CF2-glycosides for carbohydrate research.
“…The conformational preferences of glycosides are analyzed qualitatively as exo /non- exo and anti / gauche , or quantitatively by measuring the φ and ψ dihedral angles . The φ and ψ dihedral angles were defined by φ = C1″–X–C n –C n –1 and ψ = C n –X–C1″–C2″ (Figure b). , Seven flavonoids that have crystal structures were selected, quercitrin, isorhamnetin-3- O -glucoside, eupatolitin-3- O -glucoside, icariin, diosmin, tricin-5- O -glucoside, and apigenin-5- O -neohesperidoside (Figures c and S1). The crystal structures were obtained from the Cambridge Crystallographic Data Center (CCDC) .…”
Many glycosylated natural products display biological
activity
and are deglycosylated by the metabolic processes of the body. Although
unnatural CF2-glycosides have been proposed as nonhydrolyzable
analogues, CF2-derivatives of natural products are exceedingly
challenging to synthesize and few examples exist. These difluorinated
molecules may have unique conformational behavior as a consequence
of changing the glycosidic linkage. In this study, we performed conformational
searches using MacroModel followed by molecular dynamics simulations
to investigate the conformational behavior of the glycosidic bonds
in flavonoid-O-glycosides and in corresponding CF2-glycosylated derivatives. Compared to their O-glycosylated analogues, flavonoid-3-CF2-glycosides and
flavonoid-5-CF2-glycosides showed conformational bias,
whereas flavonoid-7-CF2-glycosides showed more flexibility.
Flavonoid-5-CF2-glycosides were the least flexible compared
to all others. Our results show that the site of the glycosylation
and the substitution pattern on the flavonoid determine the conformational
properties of these molecules. These two factors influence the steric
destabilization and/or stereoelectronic stabilization which govern
the conformational behavior of the flavonoid glycosides. Moreover,
a docking study of quercitrin and its CF2-analogue into
murine ribosomal kinase RSK2 demonstrated the potential for flavonoid-CF2-glycosides to retain a similar binding pose as the parent O-glycoside. These findings will assist in designing stable
flavonoid-CF2-glycosides for carbohydrate research.
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