Abstract
Chemical study of the secondary metabolites of a deep-sea-derived fungus Aspergillus sydowii MCCC 3A00324 led to the isolation of eleven compounds (1–11), including one novel (1) and one new (2) osmane-related monoterpenoids and two undescribed polyketides (3 and 4). The structures of the metabolites were determined by comprehensive analyses of the NMR and HRESIMS spectra, in association with quantum chemical calculations of the 13C NMR, ECD, and specific rotation data for the configurational assignment. Compound 1 possessed a novel monoterpenoid skeleton, biogenetically probably derived from the osmane-type monoperpenoid after the cyclopentane ring cleavage and oxidation reactions. Additionally, compound 3 was the first example of the α-pyrone derivatives bearing two phenyl units at C-3 and C-5, respectively. The anti-inflammatory activities of 1–11 were tested. As a result, compound 6 showed potent inhibitory nitric oxide production in lipopolysaccharide (LPS)-activated BV-2 microglia cells with an inhibition rate of 94.4% at the concentration of 10 µM. In addition, a plausible biosynthetic pathway for 1 and 2 was also proposed.
Highlights
Deep-sea-derived fungi inhabiting extreme sea environments have proven to be a new source for a wide array of structurally intriguing and biologically active secondary metabolites [1,2,3].As of December 2019, about 700 new secondary metabolites were reported from deep-sea-derived fungi, such as terpenoids, polyketides, alkaloids, and steroids
A literature retrieval discovered that 52 out of 59 new compounds were isolated from the marine-derived Aspergillus sydowii fungus
Www.mdpi.com/journal/marinedrugs common secondary metabolites of the A. sydowii, some of which exhibited a wide range of pharmacological activities
Summary
Deep-sea-derived fungi inhabiting extreme sea environments have proven to be a new source for a wide array of structurally intriguing and biologically active secondary metabolites [1,2,3]. As of December 2019, about 700 new secondary metabolites were reported from deep-sea-derived fungi, such as terpenoids, polyketides, alkaloids, and steroids. In our continuing efforts to discover new or bioactive secondary metabolites from deep-sea-derived fungi [12,13,14,15,16], the fungus. A literature retrieval discovered that 52 out of 59 new compounds were isolated from the marine-derived Aspergillus sydowii fungus. Only three undescribed polyketides, namely asperentin B [32], 2,3,5-trimethyl-6-(3-oxobutan-2-yl)-4H-pyran-4-one, and (2R)-2,3-dihydro-7-hydroxy-6,8-dimethyl2-[(E)-propl-enyl]
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