Anti-inflammatory metabolites from endophytic fungus Fusarium sp. (February 2019)

• Record Type: Journal Article
• Authors: Khayat, Maan T.; Ibrahim, Sabrin R.M.; Mohamed, Gamal A.; Abdallah, Hossam M.
• Is Part Of: Phytochemistry letters. Volume 29(2019)
• Page Start: 104
• Page End: 109
• Publication Date: 2019-02
• Subjects: Fusarium sp. -- Ergosterol -- Fusaristerol -- Endophytic fungi -- Anti-inflammatory -- 5-Lipoxygenase inhibitory -- Structural activity relationship; Botanical chemistry -- Periodicals; Chimie végétale -- Périodiques; 572.205
• DOI: 10.1016/j.phytol.2018.11.024
• Languages: English
• ISSNs: 1874-3900

Abstract

Graphical abstract: Highlights: The CHCl3 /MeOH extract of the endophytic fungus Fusarium sp. was investigated. Three new ergosterol derivatives and two known compounds were isolated. Their structures were established by various spectroscopic analyses. 5-LOX inhibitory capacity of all metabolites was evaluated. Abstract: Three new ergosterol derivatives, namely, fusaristerols B [(22 E, 24 R )-3-palmitoyl-19(10→6)-abeo-ergosta-5, 7, 9, 22-tetraen-3β-ol] (1 ), C [(22 E, 24 R )-ergosta-7, 22-diene-3 β, 6 β, 9 α -triol] (3 ), and D [(22 E, 24 R )-ergosta-7, 22-diene-3β, 5α, 6β, 9 α -tetraol 6-acetate] (4 ), along with (22 E, 24 R )-5 β, 8 β -epidioxyergosta-22-en-3 β -yl decanoate (2 ) and (22 E, 24 R )-ergosta-7, 22-dien-3 β -ol (5 ), were isolated and characterized from the endophytic fungus Fusarium sp. isolated from Mentha longifolia L. (Labiatae) roots growing in Saudi Arabia. The structures of the isolated metabolites were verified based on UV, IR, NMR (1D and 2D), HRMS, and a comparison with the literature. All the metabolites were assessed for 5-lipoxygenase (5-LOX) inhibitory potential. Compounds1 and2 possessed 5-LOX inhibitory potential with an IC50 s of 3.61 and 2.45 μM, respectively, compared to that of indomethacin (IC50 1.17 μM). In addition, their structure-activity relationship was discussed.