Abstract
Three new prenylated phenol derivatives, terreprenphenols A–C (1–3), along with four known related compounds (4–7), were isolated from Aspergillus terreus EN-539, an endophytic fungus obtained from the marine red alga Laurencia okamurai. The structures of these compounds were established by extensive analysis of 1D/2D NMR data, mass spectrometric data, and optical rotation (OR). The corresponding relationship between absolute configuration and optical rotation for known compounds anodendroic acid (4) and asperterreusine C (5) was ambiguous in literature, and their absolute configurations were therefore discussed and confirmed for the first time by time-dependent density functional (TDDFT) ECD and OR calculations. Compounds 1–7 inhibited some common aquatic bacteria with MIC values ranging from 2 to 64 μg/mL.
Highlights
The growing trend in the discovery of new marine natural products from marine microorganisms has continued increasing over the last few years and represented 57% of the total new marine natural products reported in 2017 [1]
O, along with related derivatives have been reported from A. terreus EN-539, which was cultured on rice-solid medium [7]
A. terreus EN-539 was further cultivated on MH2 medium, which resulted in the production of different metabolites compared with that culturing on rice-solid medium, as evidenced by HPLC analysis
Summary
The growing trend in the discovery of new marine natural products from marine microorganisms has continued increasing over the last few years and represented 57% of the total new marine natural products reported in 2017 [1]. In our previous research on new bioactive secondary metabolites from marine-derived fungi [5,6,7,8], a fungal strain Aspergillus terreus EN-539 was isolated from marine red alga Laurencia okamurai, which has been reported as a prolific producer of halogenated organic molecules, such as sesquiterpenes and nonterpenoid C15 -acetogenins [9]. O, along with related derivatives have been reported from A. terreus EN-539, which was cultured on rice-solid medium [7]. Three new prenylated phenol derivatives including terreprenphenol A (1), terreprenphenol B (2), and terreprenphenol C (3), along with four known related compounds (4–7), were isolated and identified. As the corresponding known related compounds (4–7), were isolated and identified. DPPHthe radical, were antioxidative activity against DPPH (2,2-diphenyl-1-picrylhydrazyl) radical, were evaluated
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