Microsphaerol and Seimatorone: Two New Compounds Isolated from the Endophytic Fungi, Microsphaeropsis sp. and Seimatosporium sp.

Abstract

A new polychlorinated triphenyl diether named microsphaerol (1), has been isolated from the endophtic fungus Microsphaeropsis sp. An intensive phytochemical investigation of the endophytic fungus Seimatosporium sp., led to the isolation of a new naphthalene derivative named seimatorone (2) and eight known compounds, i.e., 1-(2,6-dihydroxyphenyl)-3-hydroxybutan-1-one (3), 1-(2,6-dihydroxyphenyl)butan-1-one (4), 1-(2-hydroxy-6-methoxyphenyl)butan-1-one (5), 5-hydroxy-2-methyl-4H-chromen-4-one (6), 2,3-dihydro-5-hydroxy-2-methyl-4H-chromen-4-one (7), 8-methoxynaphthalen-1-ol (8), nodulisporins A and B (9 and 10, resp.), and daldinol (11). The structures of 1 and 2 were elucidated by detailed spectroscopic analysis including (1) H- and (13) C-NMR, COSY, HMQC, HMBC, and HR-EI-MS, while the structures of the known compounds were deduced from comparison of their spectral data with those in the literature. Preliminary studies revealed that microsphaerol (1) showed good antibacterial activities against B. Megaterium and E. coli, and good antilagal and antifungal activities against C. fusca, M. violaceum, respectively. On the other hand, seimatorone (2) exhibited moderate antibacterial, antialgal, and antifungal activities.

Volatiles from the xylarialean fungus Hypoxylon invadens

“…The compound 5-hydroxy-2-methylchroman-4-one ( 18 ), one of the major constituents in the H. invadens headspace extracts, has been reported before from various ascomycetes, especially from the genus Daldinia and other endophytic fungi [ 16 – 25 ]. It did, however, not constitute a major metabolite during the screening of numerous other species of Hypoxylon and the related Annulohypoxylon using HPLC/DAD–MS detection of organic extracts from standardised submerged cultures [ 26 ].…”

Endophytic Fungi: A Source of Potential Antifungal Compounds

“…In antifungal assay, compounds 27 and 28 showed activity against Microbotryum violaceum with 9 and 5 mm zone of inhibition (0.05 mg was pipetted onto 9 mm sterile filter paper disk). In addition, there was some growth within the zone of inhibition [ 26 ].…”

Potential Pharmacological Resources: Natural Bioactive Compounds from Marine-Derived Fungi

“…coli , and good antilagal and antifungal activities against Chlorella fusca and Microbotryum violaceum , respectively. On the other hand, compound 153 exhibited moderate antibacterial, antialgal, and antifungal activities ( Figure 33 ) [ 83 ].…”