Racemization at C-2 of naringin in pummelo (Citrus grandis) with increasing maturity determined by chiral high-performance liquid chromatography

Journal of Chromatography. a
Salvatore Caccamese, Rosa Chillemi

Abstract

The relative content of (2S)- and (2R)-naringin in the albedo of pummelo during maturation in the entire season was determined by normal-phase HPLC using Chiralpak IB, a polysaccharide-derived chiral stationary phase, and n-hexane/ethanol doped with 0.5% TFA as mobile phase. A sigmoid curve was obtained showing variation from 95.3% of (2S)-naringin in very immature fruits to 53% in mature fruit samples (2.3 and 14.4cm diameter, respectively). A comparison was made with previous results obtained for grapefruit and sour orange and a tentative explanation of the bitter taste of sour orange is proposed. The Chiralpak IB is much more efficient with respect to the Chiralcel OD used for the other two Citrus species and separation and resolution factors of 1.73 and 9.2, respectively, were achieved. Authentic samples of naringin and neohesperidin were also separated into their C-2 diastereomers with Chiralpak IB and isolation of the pure diastereomers of naringin was accomplished.

Citations

Feb 23, 2013·Journal of Agricultural and Food Chemistry·Charlotte SimmlerGuido F Pauli
Sep 3, 2014·Journal of Analytical Methods in Chemistry·Lidércia C R Cerqueira E SilvaRoy E Bruns
Aug 30, 2011·Phytochemistry·Cristiano Soleo FunariDulce Helena Siqueira Silva
Apr 11, 2015·Phytochemical Analysis : PCA·Charlotte SimmlerGuido F Pauli
Aug 16, 2016·Journal of Pharmaceutical and Biomedical Analysis·Dauh-Rurng WuArvind Mathur
Aug 3, 2012·Cellular Physiology and Biochemistry : International Journal of Experimental Cellular Physiology, Biochemistry, and Pharmacology·Nazneen ShaikFlorian Lang
Jan 16, 2018·Chirality·Meriem BouaniniHassan Y Aboul-Enein
Feb 13, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·María Del Carmen Cortés-ChitalaIrma López-Muraira

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