Galewone, an Anti-Fibrotic Polyketide from Daldinia eschscholzii with an Undescribed Carbon Skeleton

• Published in: Scientific reports Vol. 9; no. 1; pp. 14316 - 7
• Main Authors: Zhang, Ai Hua, Jiang, Nan, Wang, Xing Qi, Tan, Ren Xiang
• Format: Journal Article
• Language: English
• Published: London Nature Publishing Group UK 04.10.2019; Nature Publishing Group
• Subjects: 119/118; 631/92; 692/308; Animals; Ascomycota - chemistry; Carbon; Cell adhesion & migration; Cell culture; Cell Line; Cotton; Daldinia; Enantiomers; Extracellular matrix; Female; Fungi; Hepatic Stellate Cells - drug effects; Humanities and Social Sciences; Humans; Liver; Metabolites; Mice; Mice, Inbred BALB C; Molecular Structure; multidisciplinary; Natural products; Polyketides - chemistry; Polyketides - pharmacology; Proteins; Rats; Science; Science (multidisciplinary); Stereochemistry
• ISSN: 2045-2322; 2045-2322
• DOI: 10.1038/s41598-019-50868-9

A novel polyphenolic natural product, galewone, with undescribed carbon skeleton, was isolated as a racemate from the culture of Daldinia eschscholzii IFB-TL01, a fungus obtained from the mantis (Tenodera aridifolia) gut. The galewone structure was elucidated by a combination of MS and NMR spectra, and substantiated by X-ray crystallographic diffraction. The absolute stereochemistry of each galewone enantiomers was determined by the CD spectrum. In compliance of the structural similarities, galewone might be the shunt products of the dalesconol biosynthetic pathway. Both (−)- and ( + )-galewones were evaluated to be anti-fibrotic against activated hepatic stellate cell line, CFSC-8B, with the IC 50 values being 3.73 ± 0.21 and 10.10 ± 0.41 μM, respectively. Thus, galewone may serve as a starting molecule for the discovery of new anti-fibrotic drug.