Antcamphorols A–K, Cytotoxic and ROS Scavenging Triterpenoids from Antrodia camphorata

• Published in: Journal of natural products (Washington, D.C.) Vol. 83; no. 1; pp. 45 - 54
• Main Authors: Li, Bin, Kuang, Yi, He, Jun-Bin, Tang, Rui, Xu, Lu-Lu, Leung, Chung-Hang, Ma, Dik-Lung, Qiao, Xue, Ye, Min
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 24.01.2020; Amer Chemical Soc
• Subjects: Agaricales - drug effects; Antineoplastic Agents - chemistry; Chemistry, Medicinal; cytotoxicity; Ergosterol - analogs & derivatives; Ergosterol - chemistry; human cell lines; human diseases; Humans; Inhibitory Concentration 50; Life Sciences & Biomedicine; medicinal fungi; moieties; Molecular Structure; neoplasm cells; neoplasms; nuclear magnetic resonance spectroscopy; Pharmacology & Pharmacy; Plant Sciences; Polyporales - chemistry; Reactive Oxygen Species - analysis; Science & Technology; Steroids - chemistry; Taiwanofungus camphoratus; Triterpenes - chemistry; triterpenoids; X-ray diffraction; OXIDATIVE STRESS; DISRUPTION; LIVER-INJURY; ANTIINFLAMMATORY TRITERPENOIDS; BIOSYNTHESIS
• ISSN: 0163-3864; 1520-6025; 1520-6025
• DOI: 10.1021/acs.jnatprod.9b00580

Antrodia camphorata is a rare and valuable medicinal mushroom. In this work, 11 new triterpenoids, namely, antcamphorols A–K (1–11), together with 10 known triterpenoids, 12–21, were isolated from dish-cultured A. camphorata. Compound 1 is an unprecedented C31 lanostane-type triterpenoid featuring a methyl group at C-15 and a C-21–O–C-24 tetrahydropyran ring at C-17. Compounds 2–11 are ergostane-type triterpenoids, and they include two pairs of norergostanes 2–5. The structures of the new compounds were identified by NMR, 2D NMR, and HRESIMS data analyses. The absolute configurations of 1 and 6 were defined by X-ray diffraction data, and the absolute configuration at C-25 of 4 was determined by the modified Mosher’s method. Compounds 7, 9, 10, 16, and 19 showed significant ROS scavenging activities (63.9–70.5% at 20 μM) in high-glucose-induced HUVECs. Compounds 3 and 8 exhibited moderate cytotoxic activities against U251 (IC50, 9.2 μM) and MCF-7 (IC50, 8.1 μM) human cancer cell lines, respectively.