High-performance liquid chromatographic separation and chiroptical properties of the enantiomers of naringenin and other flavanones

Caccamese, Salvatore; Caruso, Carmelo; Parrinello, Nunziatina Laura; Savarino, Andrea

doi:10.1016/j.chroma.2005.04.024

Cited by 52 publications

(51 citation statements)

References 26 publications

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“…It should be noted that we had originally imagined degrading naringin (35) to afford optically active (S)-C(2) flavanone 9. However, in our hands, hydrolysis of the sugar results in formation of racemic 9 as determined by a Chiralcel OD-H column.…”

Section: Our Synthetic Studiesmentioning

confidence: 99%

(±)-Diinsininone: made nature's way

Selenski

Pettus

2006

Tetrahedron

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We report the synthesis of diinsininone (33), the aglycone of (±)-diinsinin (2). Thereby, we complete the first construction of a proanthocyanidin (PA) type-A compound incorporating a [3.3.1]-bicyclic ketal as its characteristic core. Our strategy utilizes a coupling between a benzopyrilium salt and a flavanone that proves applicable to other PA type-A compounds. During this undertaking, treatment of naringenin (9) with 2-iodoxybenzoic acid (IBX) followed by reductive work-up affords eriodictyol (10). This reactivity mirrors that of catechol hydroxylase (F3H) found in the flavonoid pathway. Other interesting transformations include the formation of flavonoids through an ortho-quinone methide (o-QM) cycloaddition-oxidation sequence and regioselective β-glycosidations of several unprotected flavanones suggesting a likely synthesis of 2 from the aglycone 33.

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Section: Our Synthetic Studiesmentioning

confidence: 99%

(±)-Diinsininone: made nature's way

Selenski

Pettus

2006

Tetrahedron

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“…Flow rate was 5 mL·min −1 , and the column temperature was 40°C. Separation of hesperetin C-2 enantiomers (Caccamese et al, 2005) were performed on a Chiralpak AS-H (cellulose tris-(S)-1-phenylethylcarbamate) column (4.6 × 250 mm) coated on 5 µm silica gel (Daicel Chemical Industries, Ltd. Tokyo, Japan). The mobile phase was n-hexane/2-propanol (80/20).…”

Section: Isolation Of Samplesmentioning

confidence: 99%

Protective effects of hesperidin derivatives and their stereoisomers against advanced glycation end-products formation

Mitsuhashi

Ubukata

2012

Pharmaceutical Biology

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“…To our knowledge there are only three sterochemically pure flavanones that are currently marketed internationally. Eriodictyol is marketed as the pure S-(−)-enantiomer by Fluka (Buchs, Switzerland); however it has been demonstrated by Caccamese et al that the marketed eriodictyol is indeed a R, S mixture of eriodictyol enantiomers [58]. Homoeriodictyol is marketed as the pure S-(−)-enantiomer by Indofine Chemical Company (Hillsborough, NJ), Extrasynthese (Genay, France), and ITI International Inc. (Miami.…”

Section: Introductionmentioning

confidence: 99%