Phelligridins C-F: cytotoxic pyrano[4,3-c][2]benzopyran-1,6-dione and furo[3,2-c]pyran-4-one derivatives from the fungus Phellinus igniarius

• Published in: Journal of natural products (Washington, D.C.) Vol. 67; no. 5; pp. 823 - 828
• Main Authors: Mo, S, Wang, S, Zhou, G, Yang, Y, Li, Y, Chen, X, Shi, J
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01-05-2004; Glendale, AZ American Society of Pharmacognosy
• Subjects: Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Benzofurans - chemistry; Benzofurans - isolation & purification; Benzofurans - pharmacology; Benzopyrans - chemistry; Benzopyrans - isolation & purification; Benzopyrans - pharmacology; Biological and medical sciences; China; Drug Screening Assays, Antitumor; General pharmacology; Humans; Medical sciences; Molecular Conformation; Molecular Structure; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Phellinus igniarius; Polyporaceae - chemistry; Stereoisomerism; Tumor Cells, Cultured; Asia; China; Antineoplastic agent; Liver; Lung; Basidiomycetes; Cytotoxicity; Oxygen heterocycle; Diphenols; Medicinal plant; Fungi; Folk medicine; Sporophore; Bicyclic compound; Aromatic compound; Tumor cell; Thallophyta; Human; Pharmacognosy; Lactone; Tricyclic compound; In vitro; Biological activity; Spiran; Cell line; Plant origin; Benzenic compound; Isolation; Structural analysis; Phellinus igniarius
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np030505d

Three unique pyrano[4,3-c][2]benzopyran-1,6-dione derivatives and a new furo[3,2-c]pyran-4-one, named phelligridins C-F (2-5), together with hispolon (8), (E)-4-(3,4-dihydroxyphenyl)but-3-en-2-one (9), 4-hydroxybenzaldehyde, protocatechualdehyde, syringic acid, protocatechuic acid, caffeic acid, isoergosterone, and octadecyl ferulate were isolated and identified from the ethanolic extract of Phellinus igniarius. Their structures were determined by spectroscopic methods including IR, MS, and 1D and 2D NMR experiments. The structures of the new compounds were characterized as 3-(4-hydroxystyryl)-8,9-dihydroxypyrano[4,3-c]isochromene-4-one (2), 3-(3,4-hydroxystyryl)-8,9-dihydroxypyrano[4,3-c]isochromene-4-one (3), 8,9-dihydroxy-3-[5',6'-dihydroxy-5' '-methyl-3' '-oxo-spiro[fural-2' '(3' 'H),1'-indene]-2'-yl]-1H,6H-pyrano[4,3-c][2]benzopyran-1,6-dione (4), and (3Z)-3-(3,4-dihydroxybenzylidene)-6-(3,4-dihydroxystyryl)-2,3-dihydro-2-methoxy-2-(2-oxo-propyl)furo[3,2-c]pyran-4-one (5), respectively. Some compounds including 2 and 3 showed in vitro selective cytotoxicity against a human lung cancer cell line (A549) and a liver cancer cell line (Bel7402). Possible biogenetic sequences to the formation of 1-9 are postulated.