Abstract
A chemical study of the ethyl acetate (EtOAc) extract from the deep-sea-derived fungus Penicillium thomii YPGA3 led to the isolation of a new austalide meroterpenoid (1) and seven known analogues (2−8), two new labdane-type diterpenoids (9 and 10) and a known derivative (11). The structures of new compounds 1, 9, and 10 were determined by comprehensive analyses via nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data. The absolute configurations of 1, 9, and 10 were determined by comparisons of experimental electronic circular dichroism (ECD) with the calculated ECD spectra. Compound 1 represented the third example of austalides bearing a hydroxyl group at C-5 instead of the conserved methoxy in other known analogues. To our knowledge, diterpenoids belonging to the labdane-type were discovered from species of Penicillium for the first time. Compound 1 showed cytotoxicity toward MDA-MB-468 cells with an IC50 value of 38.9 μM. Compounds 2 and 11 exhibited inhibition against α-glucosidase with IC50 values of 910 and 525 μM, respectively, being more active than the positive control acarbose (1.33 mM).
Highlights
Austalides are a class of natural meroterpenoids with attractive scaffolds
The results showed that compounds 2 and 11 inhibited α-glucosidase with IC50 values of 910 ± 4 and 525 ± 2 μM, being more active than the positive control acarbose (1.33 mM)
As results, compounds 1, 2, and 10, possessing inhibition rates of more than 50% on NO production, showed obvious cytotoxic effects, which suggested that the inhibitory effects of NO
Summary
Previous biosynthetic studies revealed that they are biosynthesized by cyclization and oxidative modification of 6-[(2E, 6E)farnesyl]-5,7-dihydroxy-4-methylphthalide [1] These meroterpenoids were mainly produced by the species of the fungal genera Aspergillus and Penicillium, especially those from marine environments. YPGA3 afforded new YPGA3 afforded a newaaustalide austalide meroterpenoid (1) and seven known analogues (2 8) 1). Two new labdane-type diterpenoids (9 and 10) and a known analogue (11). The labdane-type diterpenoids are mainly produced by plants and are plants and are rarely found in fungus. Diterpenoids belonging to the labdane-type were discovered were discovered from species of Penicillium for the first time. Against α-glucosidase and NO (nitric oxide) production in lipopolysaccharide (LPS)-activated RAW activated RAW 264.7 macrophages, and cytotoxicity toward two types of human breast carcinoma.
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