Isopentylated diphenyl ether derivatives from the fermentation products of an endophytic fungus Phomopsis fukushii

Abstract

Three new isopentylated diphenyl ethers, (1-3), together with two known isopentylated diphenyl ethers derivatives (4 and 5) were isolated from the fermentation products of an endophytic fungus Phomopsis fukushii. Their structures were elucidated by spectroscopic methods, including extensive 1D- and 2D NMR techniques. Compounds 1-3 were evaluated for their anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) activity. The results showed that compounds 1-3 showed strong activity with diameter of inhibition zone (IZD) of 21.8 ± 2.4 mm, 16.8 ± 2.2 mm, and 15.6 ± 2.0 mm, respectively.

Fungal Endophytes: A Potential Source of Antibacterial Compounds

“…Newly reported bioactive compounds have shown activity against various pathogenic bacteria and shown scaffold similarity with alkaloids, benzopyranones, chinones, cytochalasins, mullein, peptides, phenols, quinones, flavonoids, steroids, terpenoids, sesquiterpene, tetralones, xanthones, and others. The lowest in vitro activity in terms of minimum inhibitory concentrations (MICs) in the 0.1-1 µg/mL range against various pathogens was reported for the compounds vochysiamides A (23) and B (24), colletotrichone A (376), 15-hydroxy-1,4,5,6-tetra-epi-koninginin G (322), trichocadinin G (330) and eupenicinicol D (435). Compounds like fusarubin (287), chetomin (62), chaetocochin C (63), and dethiotetra(methylthio)chetomin (64), pretrichodermamide A (296), terpestacin (105), fusaproliferin (106), mutolide (108), isoeugenitol (120) and nigrosporone B (417) were reported to have significant in vitro anti-mycobacterial activity and could be developed as potential drugs against resistant mycobacterial infections.…”

“…yunnanensis yielded three new isopentylated diphenyl ethers, 1-(4-(3-methoxy-5-methylphenoxy)-2-methoxy-6methylphenyl)-3-methylbut-3-en-2-one (14), 1-(4-(3-(hydroxymethyl)-5-methoxyphenoxy)-2-methoxy-6-methylphenyl)-3-methylbut-3-en-2-one (15) and 1-(4-(3-hydroxy-5-(hydroxym ethyl) phenoxy)-2-methoxy-6-methylphenyl)-3-methylbut-3-en-2-one (16, Figure 1). Compounds 14-16 displayed anti-MRSA activity with 21.8, 16.8 and 15.6 mm inhibition zones, respectively (50 µg/6 mm disc) [24].…”

Bioactive Secondary Metabolites of the Genus Diaporthe and Anamorph Phomopsis from Terrestrial and Marine Habitats and Endophytes: 2010–2019

“…yunnanensis , gave three new isopentylated diphenyl ethers ( 123 – 125 ). Compounds ( 123 – 125) had notable anti-MRSA activities, and their IZD were 21.8 ± 2.4 mm, 16.8 ± 2.2 mm, and 15.6 ± 2.0 mm, respectively [ 66 ]. Two new diphenyl ethers ( 126 – 127 ) were obtained from the fermentation products of P .…”

Molecular Insight into Gene Response of Diorcinol- and Rubrolide-Treated Biofilms of the Emerging Pathogen Stenotrophomonas maltophilia

“…Despite the studies that demonstrated an antibacterial effect for the diorcinols ( 36 , 40 , 43 , 44 ), no study has so far analyzed their effect on biofilm architecture. Thus, the observations made here may imply that rubrolides and diorcinols are potentially interesting compounds for antibiofilm treatment.…”

“…1A ) substitute both phenyl groups. They are mostly isolated from fungi ( 38 – 41 ) and are known to have antifungal ( 42 ) and antibacterial effects ( 36 , 40 , 43 , 44 ). In addition, they have cytotoxic activity against tumorous cells ( 38 , 39 , 41 ).…”