Biotransformation of cyclocanthogenol by the endophytic fungus Alternaria eureka 1E1BL1. (July 2018)

• Record Type: Journal Article
• Authors: Ekiz, Güner; Duman, Seda; Bedir, Erdal
• Is Part Of: Phytochemistry. Volume 151(2018)
• Page Start: 91
• Page End: 98
• Publication Date: 2018-07
• Subjects: Astragalus -- Fabaceae -- Biotransformation -- Cycloartanes -- Cyclocanthogenol -- Endophytic fungus -- Alternaria eureka; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2018.04.006
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: The microbial transformation of cyclocanthogenol (CCG), Astragalus sp. originated sapogenin, by the endophytic fungus Alternaria eureka 1E1BL1 isolated from Astragalus angustifolius was investigated. Hydroxylation, oxidation, epoxidation, O -methylation, ring-expansion and methyl migration reactions were observed on the triterpenoid skeleton. As a result, eight metabolites were isolated and the structures of the previously undescribed compounds were established by 1-D, 2-D NMR and HR-MS analyses. Graphical abstract: The incubation of cyclocanthogenol (CCG) with the endophytic fungus A. eureka 1E1BL1 afforded seven previously undescribed compounds. Highlights: Microbial transformation of cyclocanthogenol yielded eight metabolites. Endophytic fungus Alternaria eureka 1E1BL1 was used as biocatalyst. Hydroxylation, oxidation, epoxidation, O -methylation, ring-expansion and methyl migration reactions were observed. Microbial hydroxylation of cycloartane nucleus at C-17 and C-22 positions was reported for the first time.