Tremmel, Martina and Kiermaier, Josef and Heilmann, Joerg (2021) In Vitro Metabolism of Six C-Glycosidic Flavonoids from Passiflora incarnata L. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 22 (12): 6566. ISSN , 1422-0067
Full text not available from this repository. (Request a copy)Abstract
Several medical plants, such as Passiflora incarnata 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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PHENOLIC-COMPOUNDS; DRUG-METABOLISM; ORIENTIN; VITEXIN; QUANTIFICATION; ISOORIENTIN; KAEMPFEROL; SULFATION; FOOD; flavonoids; metabolism; C-glycosides; C-C cleavage; Caco-2 cells; Passiflora incarnata L |
| Subjects: | 600 Technology > 615 Pharmacy |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann) Chemistry and Pharmacy > Central Analytical Services |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 22 Aug 2022 06:16 |
| Last Modified: | 22 Aug 2022 06:16 |
| URI: | https://pred.uni-regensburg.de/id/eprint/46187 |
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