Several medical plants, such as L., contain C-glycosylated flavonoids, which may contribute to their efficacy. Information regarding the bioavailability and metabolism of these compounds is essential, but not sufficiently available. Therefore, the metabolism of the C-glycosylated flavones orientin, isoorientin, schaftoside, isoschaftoside, vitexin, and isovitexin was investigated using the Caco-2 cell line as an in vitro intestinal and epithelial metabolism model. Isovitexin, orientin, and isoorientin showed broad ranges of phase I and II metabolites containing hydroxylated, methoxylated, and sulfated compounds, whereas schaftoside, isoschaftoside, and vitexin underwent poor metabolism. All metabolites were identified via UHPLC-MS or UHPLC-MS/MS using compound libraries containing all conceivable metabolites. Some structures were confirmed via UHPLC-MS experiments with reference compounds after a cleavage reaction using glucuronidase and sulfatase. Of particular interest is the observed cleavage of the C-C bonds between sugar and aglycone residues in isovitexin, orientin, and isoorientin, resulting in unexpected glucuronidated or sulfated luteolin and apigenin derivatives. These findings indicate that C-glycosidic flavones can be highly metabolized in the intestine. In particular, flavonoids with ortho-dihydroxy groups showed sulfated metabolites. The identified glucuronidated or sulfated aglycones demonstrate that enzymes expressed by Caco-2 cells are able to potentially cleave C-C bonds in vitro.
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http://dx.doi.org/10.3390/ijms22126566 | DOI Listing |
Molecules
December 2024
UMRT INRAE 1158 BioEcoAgro, BIOlogie des Plantes et Innovation (BIOPI), Université de Picardie Jules Verne, IUT GB, Avenue des Facultés, Le Bailly, 80025 Amiens, France.
Flavonoids have been documented to have good antioxidant activities in vitro. In recent years, reports on the antioxidant activities of flavone glycosides, a subclass of flavonoids, have attracted great attention. Despite the wealth of information on this subject, the correlation between structure and function is not well understood.
View Article and Find Full Text PDFFitoterapia
January 2025
Laboratory of Bioprospection and Applied Ethnopharmacology, Federal University of Rio de Janeiro (UFRJ), 21941-902 Rio de Janeiro, Brazil. Electronic address:
Lippia origanoides Kunth (LO, Verbenaceae), commonly known in Brazil as salva-de-marajó, is an aromatic plant native to the Americas. Quilombola women from Oriximiná (Pará State, Brazil) use decoctions and decoction vapors of LO aerial parts orally or in sitz baths to alleviate symptoms of dysmenorrhea. This study aimed to evaluate LO decoctions and essential oils through a chemo-qualitative approach.
View Article and Find Full Text PDFSe Pu
October 2024
International Centre for Bamboo and Rattan, Key Laboratory of National Forestry and Grassland Administration/Beijing for Bamboo and Rattan Science and Technology, Beijing 100102, China.
The flavonoid contents of different bamboo-leaf extracts and their relationships to antioxidant activity were investigated in this study by preparing nine samples using two commercially available bamboo-leaf extract products and seven bamboo-leaf extracts such as . A high performance liquid chromatography (HPLC) method was established to determine seven flavonoid components (orientin, isoorientin, vitexin, isovitexin, tricin, luteolin and luteoloside) in these samples, which were separated using a SymmetryShield RP8 column (250 mm×4.6 mm, 5 μm) under gradient-elution conditions using acetonitrile as mobile phase A and 0.
View Article and Find Full Text PDFChem Biodivers
November 2024
Nucleo de Estudos e Pesquisas de Plantas Medicinais (NEPLAME), Federal University of Vale do São Francisco, 56304-205, Petrolina, Pernambuco, Brazil.
Int J Biol Macromol
October 2024
Key Laboratory of Biofuels, Shandong Provincial Key Laboratory of Energy Genetics, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Shandong Energy Institute, Qingdao New Energy Shandong Laboratory, Qingdao 266101, China. Electronic address:
C-glycosylated flavones (CGFs) are the main flavonoids in duckweed (Lemna turionifera), known for their diverse pharmacological activities and nutritional values. However, the molecular mechanisms underlying flavonoid metabolism in duckweed remain poorly understood. This study identified a P1-Like R2R3-MYB transcription factor, LtP1L, as a crucial regulator of CGF biosynthesis and transport in L.
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