Flavanone

About: Flavanone is a research topic. Over the lifetime, 1965 publications have been published within this topic receiving 54729 citations. The topic is also known as: flavanones.

Synthesis of non-natural flavanones and dihydrochalcones in metabolically engineered yeast

Abstract: Flavonoids are plant phenolic compounds that have many interesting medicinal properties. Therefore, there is interest in the synthesis of non-natural flavonoids as they may possess new or enhanced biological activities. In this study, metabolically engineered Saccharomyces cerevisiae expressing 4-coumaroyl:CoA-ligase (4CL) and chalcone synthase (CHS) was explored as a platform for producing non-natural flavanones and dihydrochalcones. By precursor addition of cinnamic acid analogues to the engineered yeast, numerous non-natural flavanones and dihydrochalcones were formed in vivo. Also, several CHS derailment products were formed. Of the isolated compounds, one flavanone and three derailment products were found to be novel compounds.

Minor flavanones from Erythrina abyssinica

Abstract: Four new prenylated flavanones, abyssinone-V 4'-methyl ether (1) and abyssinoflavanones IV (2), V (3), and VI (4), have been isolated as minor flavanones from the African medicinal plant, Erythrina abyssinica, together with a known flavanone, sigmoidin D. The structure elucidation of compounds 1-4 by spectroscopic studies is described.

Synthesis of Both Enantiomers of Flavanone and 2-Methylchromanone

Abstract: An efficient enantiospecific synthesis of the (R)- and (S)-enantiomers of flavanone and 2-methylchromanone is described. The key steps are a C,C-bond formation by ring opening of a chiral epoxide with a dithiane anion, followed by a Mitsunobu cyclization. The products obtained have high enantiomeric purity.

Phenolic profiling and quantitative determination of common sage (Salvia plebeia R. Br.) by UPLC-DAD-QTOF/MS

Abstract: Salvia plebeia R. Br. is a medicinal herb that contains important active compounds such as flavonoid and phenolic acid which are responsible for remarkable biological properties. The phenolic composition of S. plebeia was quantitatively investigated using ultra-performance liquid chromatograph coupled with photodiode array detection and quadrupole time of flight mass spectrometry. A total of 16 flavonoids were classified into 10 flavones and 6 flavanones based on UV-spectra and ion fragmentation patterns. Individual flavonoids, including apigenin, luteolin, hispidulin, nepetin, and some flavanones, were glycosylated with glucose at the 5- or 7-position of flavonoid structure. The three major flavones were determined to be 6-hydroxyluteolin 7-O-glucoside [2,452.7 mg/100 g dry weight (DW)], hispidulin 7-O-glucoside (2,281.0 mg/100 g DW) and nepetin 7-O-glucoside (2,002.6 mg/100 g DW). The six flavanones containing the hydroxyl and methoxy groups were determined and, among them, 5,7,3′,4′- tetrahydroxy-6-methoxyflavanone 7-O-glucoside have the highest level (938.3 mg/100 g DW). Two hydroxyl flavanone glycosides, 5,6,7,3′,4′- pentahydroxyflavanone 7-O-glucoside and 5,6,7,4′- tetrahydroxyflavanone 7-O-glucoside, were presumed to be newly identified compounds, on the basis of the library data from S. plebeia. In addition, higher concentration of rosmarinic acid was also identified.

Quasi-MSn identification of flavanone 7-glycoside isomers in Da Chengqi Tang by high performance liquid chromatography-tandem mass spectrometry.

Abstract: Da Chengqi Tang (DCT) is a common purgative formula in Chinese medicine. Flavanones are its major active compounds derived from Fructus Aurantii Immaturus. The present study developed an LC-MS/MS method to characterize two pairs of flavanone 7-glycoside isomers, i.e., hesperidin versus neohesperidin and naringin versus isonaringin. After solid phase purification, components in sample were separated on a Agilent zorbax SB-C18 (5 μm, 250 mm × 4.6 mm) analytical column. ESI-MS and quasi-MSn were performed in negative ion mode to obtain structural data of these two pairs of flavanone 7-glycoside isomers. Moreover, UV absorption was measured. There was no intra-pairs difference in the UV-Vis and MS/MS spectra of the two pairs of 7-glycoside isomers, whereas the mass spectrometry fragmentation pathways between pairs were different. The present study developed a LC-MS/MS method to explore the inter- and intra-pair difference of two pairs of flavanone 7-glycoside isomers.