5-Hydroxycyclopenicillone, a New β-Amyloid Fibrillization Inhibitor from a Sponge-Derived Fungus Trichoderma sp. HPQJ-34

• Published in: Marine drugs Vol. 15; no. 8; p. 260
• Main Authors: Fang, Fang, Zhao, Jiaying, Ding, Lijian, Huang, Chunhui, Naman, C Benjamin, He, Shan, Wu, Bin, Zhu, Peng, Luo, Qijun, Gerwick, William H, Yan, Xiaojun, Wang, Qinwen, Zhang, Zaijun, Cui, Wei
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 19.08.2017; MDPI
• Subjects: Absolute configuration; Alzheimer's disease; Amyloid - drug effects; Animals; Biphenyl Compounds - chemistry; Cell culture; Cell Line - drug effects; Cells; Circular Dichroism; Cyclopentanes - chemistry; Cyclopentanes - pharmacology; cyclopentenone; Dichroism; Fibrillogenesis; Free Radical Scavengers - chemistry; Free Radical Scavengers - pharmacology; Free radicals; Fungi; Humans; Hydrogen peroxide; In vitro methods and tests; Neuroprotection; Neurotoxicity; Phytotherapy; Picrates - chemistry; Porifera - microbiology; Spectra; sponge-derived fungus; Trichoderma; Trichoderma sp. HPQJ-34; β-Amyloid; cyclopentenone; Trichoderma sp. HPQJ-34; Alzheimer’s disease; sponge-derived fungus
• ISSN: 1660-3397; 1660-3397
• DOI: 10.3390/md15080260

A new cyclopentenone, 5-hydroxycyclopeni cillone ( ), was isolated together with three known compounds, -turmerone ( ), citreoisocoumarin ( ), and 6-O-methyl-citreoisocoumarin ( ), from a culture of the sponge-derived fungus sp HPQJ-34. The structures of - were characterized using comprehensive spectroscopic analyses. The absolute configuration of was determined by comparison of electronic circular dichroism (ECD) spectra with literature values used for the reported analogue, cyclopenicillone ( ), which was not isolated in this research. Compound 1 was shown to scavenge 2,2-diphenyl-1-picrylhydrazyl free radicals, and decrease β-amyloid (Aβ) fibrillization in vitro. Moreover, 1 significantly reduced H₂O₂-induced neurotoxicity in SH-SY5Y cells. These findings suggested that compound 1, a newly discovered cyclopentenone, has moderate anti-oxidative, anti-Aβ fibrillization properties and neuroprotective effects, and might be a good free radical scavenger.