Butyrolactones Derivatives from the Fermentation Products of an Endophytic Fungus Aspergillus versicolor

Abstract

Two new butyrolactones, asperphenol A (1) and B (2), together with four known butyrolactones (3-6) were isolated from the fermentation products of an endophytic fungus Aspergillus versicolor. Their structures were elucidated by spectroscopic methods including extensive 1D-and 2D-NMR techniques. Compounds 1-6 were also tested for their anti-tobacco mosaic virus (anti-TMV) activities. The results showed that compound 2 exhibited high anti-TMV activity with inhibition rate of 46.7%. The other compounds also exhibited potential anti-TMV activities with inhibition rates in the range of 21.8-28.4%.

Butyrolactones derivatives from the fermentation products of a plant entophytic fungusPenicillium oxalicum

“…In addition, the other 2D data can further confirm the prenyl group to be located at C-5 00 , the phenolic hydroxy group at C-4 00 and another methoxy group at C-3 00 . Compound 1 showed the Cotton effects at 225 and 316 nm in the CD spectrum, and the optical rotation valve of þ 65.8, respectively, which was similar to those of the known compound Ye et al 2014), indicating the presence of R configuration at C-4 in 1.…”

“…Therefore, 1 must possess one aliphatic ring in addition to two aromatic rings. The typical carbon signals (d C 169.1 s, 139.5 s, 126.3 s, 85.8 s, 40.0 t and 170.2 s) indicated that 1 should be a phenyl butyrolactone derivative Ye et al 2014). A detailed comparison of the NMR data of 1 with those of the known compound, terrephenol A ) revealed that the only difference was due to the absence of a phenolic hydroxy group and the appearance of a methoxy group (d C 56.0 q, d H 3.81 s) in 1.…”

“…Since some butyrolactones are known to exhibit potential anti-virus activities (Zhang et al 2005;Gao et al 2013;Li et al 2014;Ye et al 2014), compounds 1 and 2 were tested for their anti-TMV activities. The inhibitory activities of compounds 1 and 2 against TMV replication were tested using the half-leaf method (Hu et al 2013).…”

Butyrolactone-I from Coral-Derived Fungus Aspergillus terreus Attenuates Neuro-Inflammatory Response via Suppression of NF-κB Pathway in BV-2 Cells

“…Butyrolactone-I was obtained as a yellowish oil by repeated column chromatography of the fermentation extract of marine fungal strain A. terreus XWC21-10. Its NMR and specific optical rotation data are listed as following and compared with a previous report [ 21 ].…”

γ-Butyrolactones from Aspergillus Species: Structures, Biosynthesis, and Biological Activities

“…The results showed that 33 exhibited high anti-TMV activity with an inhibition rate of 46.7% compared with ningnanmycin (30.6 inhibition %). The other compounds also exhibited anti-TMV activities with inhibition rates in the range of 21.8-28.4% [40]. Also, the anti-TMV activities of 1, 3, 16, 35, 36, and 74 were evaluated using the half-leaf method.…”