Meroterpenoids from a Medicinal Fungus Antrodia cinnamomea
Journal
Journal of Natural Products
Journal Volume
80
Journal Issue
9
Pages
2439 - 2446
Date Issued
2017-09
Author(s)
Abstract
Antrodia cinnamomea, a medicinal fungus indigenous to Taiwan, has been shown to exhibit a broad spectrum of bioactivities for the treatments of alcoholic intoxication, diarrhea, abdominal pain, and fatigue, and a number of active principles have been identified. Among the bioactive entities, clinical trials of antroquinonol and 4-acetyl antroquinonol B are being carried out for curing cancer, hypercholesterolemia, and hyperlipidemia. The total synthesis of antroquinonol has been achieved; however, investigating the structure-activity relationship of this class of compounds remained difficult due to the lack of available analogues. Twenty antroquinonols isolated from A. cinnamomea IFS006 are reported herein. Their structures were elucidated using spectral analysis and by comparison with literature values. Of these, 11 antroquinonol analogues, namely, antroquinonols N-X (1-11), were previously unreported. The growth inhibitory activity of all the antroquinonol analogues was evaluated against human A549 and PC-3 cancer cell lines, and antroquinonol A exhibited the most potent activity, with GI50 values of 5.7 ± 0.2 and 13.5 ± 0.2 μM, respectively. Antroquinonols V (9) and W (10) also showed growth inhibitory activity against A549 cells with GI50 values of 8.2 ± 0.8 and 7.1 ± 2.1 μM, respectively, compared to 5-fluorouracil (GI50 = 4.2 ± 0.2 μM). ? 2017 The American Chemical Society and American Society of Pharmacognosy.
SDGs
Other Subjects
antroquinonol N; antroquinonol O; antroquinonol P; antroquinonol Q; antroquinonol R; antroquinonol S; antroquinonol T; antroquinonol U; antroquinonol V; antroquinonol W; antroquinonol X; cytotoxic agent; fluorouracil; natural product; terpenoid derivative; unclassified drug; 4-acetyl antroquinonol B; antroquinonol; antroquinonol V; antroquinonol W; fluorouracil; terpene; ubiquinone; A-549 cell line; antineoplastic activity; Antrodia camphorata; Article; cancer inhibition; carbon nuclear magnetic resonance; controlled study; drug isolation; drug potency; drug screening; electrospray mass spectrometry; heteronuclear multiple bond correlation; heteronuclear single quantum coherence; human; human cell; male; nonhuman; nuclear Overhauser effect; PC 3 cell line; prostate cancer cell line; proton nuclear magnetic resonance; structure activity relation; analogs and derivatives; Antrodia; chemical structure; chemistry; fungus; isolation and purification; synthesis; Taiwan; Antrodia; Fluorouracil; Fungi; Humans; Molecular Structure; Structure-Activity Relationship; Taiwan; Terpenes; Ubiquinone
Type
journal article