Catalytic approach to in vivo metabolism of atractylenolide III using biomimetic iron-porphyrin complexes
- Authors
- Lim, Hanae; Jeon, Hyeri; Hong, Seungwoo; Kim, Jung-Hoon
- Issue Date
- Oct-2021
- Publisher
- ROYAL SOC CHEMISTRY
- Citation
- RSC ADVANCES, v.11, no.52, pp 33048 - 33054
- Pages
- 7
- Journal Title
- RSC ADVANCES
- Volume
- 11
- Number
- 52
- Start Page
- 33048
- End Page
- 33054
- URI
- https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/146308
- DOI
- 10.1039/d1ra05014a
- ISSN
- 2046-2069
2046-2069
- Abstract
- Atractylenolide III (AT-III) is a pharmacologically effective phytochemical and is known to be oxygenated during systemic metabolism mainly by cytochrome P450 enzymes (CYP450s), iron-containing porphyrin-based oxygenases. In rat plasma samples, the oxygenated metabolite of orally ingested AT-III was determined using liquid chromatography/mass spectrometry and the oxygenated form of AT-III was maintained at higher levels than the original form of AT-III. In situ catalytic reactions using the iron(iv)-oxo porphyrin pi-cation radical complex, [(tmp(+))Fe-IV(O)](+), demonstrated that both H-atom abstraction and an oxygen rebound mechanism participated in the oxygenation process of AT-III. Density functional theory (DFT) confirmed the oxidative transformation occurred at the 4th and 10th carbon positions of AT-III. Co-treatment with acetaminophen had different effects between in vivo and in situ models of AT-III metabolism. AT-III was metabolized via an oxygenation process in the rat body, where CYP450 and other O-2-activating metalloenzymes might participate in the metabolism. The present work provided the oxidative metabolism of AT-III using an in vivo model parallel with in situ biomimetic reaction models.
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