Metabolites of Antroquinonol Found in Rat Urine Following Oral Administration

Chen, Chien Kuang; Kang, Jaw Jou; Wen, Wu; Chiang, Hui Fen; Lee, Shoei‐Sheng

doi:10.1021/np400670a

Cited by 7 publications

(5 citation statements)

References 11 publications

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“…Moreover, a recent study identified four major metabolites from the urine of ANQtreated rat. 41 However, the bioactivity of these metabolites has not been determined yet. After much effort to improve the productivity and exciting biological properties of ANQ, ANQ is currently undergoing phase II clinical trials (in the United States and Taiwan) for non-small-cell lung cancer and was granted orphan drug status for pancreatic cancer.…”

Section: ■ Discussionmentioning

confidence: 99%

“…Our study shows consistent results with previous findings that ANQ at 5 μM concentration exhibits antitumor activities; therefore, it is an achievable dosage from the supplement. Moreover, a recent study identified four major metabolites from the urine of ANQ-treated rat . However, the bioactivity of these metabolites has not been determined yet.…”

Section: Discussionmentioning

confidence: 99%

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Antroquinonol, a Ubiquinone Derivative from the Mushroom Antrodia camphorata, Inhibits Colon Cancer Stem Cell-like Properties: Insights into the Molecular Mechanism and Inhibitory Targets

Lin

Liao

et al. 2016

J. Agric. Food Chem.

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Antroquinonol (ANQ) is a ubiquinone derivative from the unique mushroom Antrodia camphorata, which exhibits broad-spectrum bioactivities. The effects of ANQ on cancer stem cell-like properties in colon cancer, however, remain unclear. In this study, we found that ANQ inhibited growth of colon cancer cells. The 50% growth inhibitions (GI) of ANQ on HCT15 and LoVo were 34.8 ± 0.07 and 17.9 ± 0.07 μM. Moreover, ANQ exhibited inhibitory activities toward migration/invasion and tumorsphere formation of colon cancer cells. Mechanistically, ANQ inhibited pluripotent and cancer stem cell-related genes and down-regulated β-catenin/T-cell factor (TCF) signaling. Moreover, activation of the phosphatidylinositol-3-kinase (PI3K)/AKT/β-catenin signaling axis was identified to be crucial for regulating the expressions of pluripotent genes, whereas suppression of PI3K/AKT by ANQ inhibited expressions of β-catenin and downstream targets. Molecular docking identified the potential interaction of ANQ with PI3K. Our data show for the first time that the bioactive component of A. camphorata, ANQ, suppresses stem cell-like properties via targeting PI3K/AKT/β-catenin signaling. ANQ could be a promising cancer prevention agent for colon cancer.

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Section: ■ Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Antroquinonol, a Ubiquinone Derivative from the Mushroom Antrodia camphorata, Inhibits Colon Cancer Stem Cell-like Properties: Insights into the Molecular Mechanism and Inhibitory Targets

Lin

Liao

et al. 2016

J. Agric. Food Chem.

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“…Besides 1a-d, their transpositional isomers 2a-d were obtained as a new chemical entity for potential evaluation of their bioactivities. 27 The analogous compounds 15a-d and 16a-d having a benzyl substituent at the C-5 position were also prepared. Their structures were rigorously established by meticulous NMR analyses with the assistance of X-ray diffraction measurements of some of the crystalline compounds.…”

Section: Discussionmentioning

confidence: 99%

A short synthesis of (±)-antroquinonol in an unusual scaffold of 4-hydroxy-2-cyclohexenone

2015

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Antroquinonol, which was first isolated from a mushroom, Antrodia cinnamomea, found in Taiwan, is an anticancer compound with a unique core structure of 4-hydroxy-2,3-dimethoxycyclohex-2-enone carrying methyl, farnesyl and hydroxyl substituents in the 4,5-cis-5,6-trans configuration. A short synthesis of (±)-antroquinonol is accomplished in seven steps from 2,3,4-trimethoxyphenol, which is oxidized in methanol to a highly electron-rich substrate of 2,3,4,4-tetramethoxycyclohexadienone and then a Michael reaction with dimethylcuprate is performed as the key step, followed by alkylation, reduction and epimerization to incorporate the required substituents at three contiguous stereocenters.

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“…The mean elimination half-life ranged from 1.30 to 4.33 h, regardless of the treatment dose. Four metabolites of antroquinonol were identified by NMR spectroscopic analysis from the male Wistar rats’ urine following oral treatment ( Chen et al, 2014 ). These results suggest that antroquinonol has good bioavailability, but the biological activity of four metabolites of antroquinonol was not determined.…”

Section: Metabolism and Blood-brain Barrier Penetration Of Acmentioning

confidence: 99%

Current and further outlook on the protective potential of Antrodia camphorata against neurological disorders

Li,

Wan,

Qiao

et al. 2024

Front. Pharmacol.

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Prevalent neurological disorders such as Alzheimer’s disease, Parkinson’s disease, and stroke are increasingly becoming a global burden as society ages. It is well-known that degeneration and loss of neurons are the fundamental underlying processes, but there are still no effective therapies for these neurological diseases. In recent years, plenty of studies have focused on the pharmacology and feasibility of natural products as new strategies for the development of drugs that target neurological disorders. Antrodia camphorata has become one of the most promising candidates, and the crude extracts and some active metabolites of it have been reported to play various pharmacological activities to alleviate neurological symptoms at cellular and molecular levels. This review highlights the current evidence of Antrodia camphorata against neurological disorders, including safety evaluation, metabolism, blood-brain barrier penetration, neuroprotective activities, and the potential on regulating the gut-microbiome-brain axis. Furthermore, potential strategies to resolve problematic issues identified in previous studies are also discussed. We aim to provide an overview for the ongoing development and utilization of Antrodia camphorata in cerebral neuropathology.

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Metabolites of Antroquinonol Found in Rat Urine Following Oral Administration

Cited by 7 publications

References 11 publications

Antroquinonol, a Ubiquinone Derivative from the Mushroom Antrodia camphorata, Inhibits Colon Cancer Stem Cell-like Properties: Insights into the Molecular Mechanism and Inhibitory Targets

Antroquinonol, a Ubiquinone Derivative from the Mushroom Antrodia camphorata, Inhibits Colon Cancer Stem Cell-like Properties: Insights into the Molecular Mechanism and Inhibitory Targets

A short synthesis of (±)-antroquinonol in an unusual scaffold of 4-hydroxy-2-cyclohexenone

Current and further outlook on the protective potential of Antrodia camphorata against neurological disorders

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