Cyathane diterpenoids and drimane sesquiterpenoids with neurotrophic activity from cultures of the fungus Cyathus africanus

• Published in: Journal of antibiotics 2019-01, Vol.72 (1), p.15-21
• Main Authors: Kou, Rong-Wei, Du, Shuang-Tian, Li, Yi-Xiao, Yan, Xi-Tao, Zhang, Qiang, Cao, Chen-Yu, Yin, Xia, Gao, Jin-Ming
• Format: Article
• Language: English
• Subjects: 101/58; 101/6; 631/1647/2230; 631/92/349; Animals; Antibiotics; Bacteriology; Biomedical and Life Sciences; Bioorganic Chemistry; Culture Media - chemistry; Cyathus - growth & development; Cyathus - metabolism; Diterpenes - chemistry; Diterpenes - isolation & purification; Diterpenes - pharmacology; Fungi; Life Sciences; Magnetic Resonance Spectroscopy; Medicinal Chemistry; Microbiology; Molecular Structure; Neurons - drug effects; Neurons - physiology; Neuroprotective Agents - chemistry; Neuroprotective Agents - isolation & purification; Neuroprotective Agents - pharmacology; Organic Chemistry; PC12 Cells; Rats; Sesquiterpenes - chemistry; Sesquiterpenes - isolation & purification; Sesquiterpenes - pharmacology; Spectrometry, Mass, Electrospray Ionization
• ISSN: 0021-8820; 1881-1469
• DOI: 10.1038/s41429-018-0106-3

Five terpenoids, including two new cyathane diterpenoids neocyathin S ( 1 ) and neocyathin T ( 2 ), together with three drimane sesquiterpenoids, one known 3 β ,6 β -dihydroxycinnamolide ( 3 ), two new ones 3 β ,6 α -dihydroxycinnamolide ( 4 ) and 2-keto-3 β ,6 β -dihydroxycinnamolide ( 5 ), were isolated from the cultures of the basidiomycete Cyathus africanus . Their structures were established based on extensive spectroscopic methods including 2D NMR (HSQC, 1 H‒ 1 H-COSY, HMBC, ROESY) and HRESIMS experiments. The absolute configurations of two pairs of epimers, 1 and 2 as well as 3 and 4 , were determined by ECD quantum chemical calculation. All the five compounds enhanced nerve growth factor (NGF)-mediated neurite outgrowth using rat pheochromocytoma (PC12) cells at concentration 10  µ M.