Catalytic approach to in vivo metabolism of atractylenolide III using biomimetic iron-porphyrin complexes

Hanae Lim, Hyeri Jeon, Seungwoo Hong, Jung Hoon Kim

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2 Scopus citations


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 π-cation radical complex, [(tmp+)FeIV(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 O2-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.

Original languageEnglish
Pages (from-to)33048-33054
Number of pages7
JournalRSC Advances
Issue number52
StatePublished - 18 Sep 2021

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© 2021 The Royal Society of Chemistry.


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