Phelligridimer A, a Highly Oxygenated and Unsaturated 26-Membered Macrocyclic Metabolite with Antioxidant Activity from the Fungus Phellinus igniarius

• Published in: Organic letters Vol. 7; no. 21; pp. 4733 - 4736
• Main Authors: Wang, Ying, Wang, Su-Juan, Mo, Shun-Yan, Li, Shuai, Yang, Yong-Chun, Shi, Jian-Gong
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 13.10.2005; Amer Chemical Soc
• Subjects: Animals; Antioxidants - isolation & purification; Antioxidants - pharmacology; Basidiomycota - metabolism; Cell Line, Tumor; Cell Survival - drug effects; Chemistry; Chemistry, Organic; Humans; Lipid Peroxidation - drug effects; Macrocyclic Compounds - isolation & purification; Macrocyclic Compounds - pharmacology; Medicine, Chinese Traditional; Models, Molecular; Molecular Structure; Physical Sciences; Protein Tyrosine Phosphatases - antagonists & inhibitors; Pyrones - isolation & purification; Pyrones - pharmacology; Rats; Science & Technology; PIGMENT; DERIVATIVES; MUSHROOM
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol0520875

A highly oxygenated and unsaturated 26-membered macrocyclic metabolite, phelligridimer A (1), has been isolated from the Chinese medicinal fungus Phellinus igniarius. Its structure was elucidated by spectroscopic methods. A possible biogenesis of 1 mediated by the fungal metabolite hispidin was postulated. Phelligridimer A showed antioxidant activity (IC50 of 10.2 μM) but was inactive to several human cancer cell lines (IC50 > 50 μM) and enzymes PTP1B (IC50 > 25 μM) and thrombin (IC50 > 10 μM).