Bisthiodiketopiperazines and Acorane Sesquiterpenes Produced by the Marine-Derived Fungus Penicillium adametzioides AS-53 on Different Culture Media

Chemical investigation of the marine-sponge-derived
fungus Penicillium adametzioides AS-53
resulted in the identification
of two new bisthiodiketopiperazine derivatives, adametizines A (1) and B (2), from cultivation in a liquid potato–dextrose
broth (PDB) culture medium, whereas two new acorane sesquiterpenes,
adametacorenols A (3) and B (4), were isolated
from a rice solid culture medium. The structures of these compounds
were elucidated on the basis of spectroscopic analysis. The absolute
configuration of compound 1 was determined by X-ray crystallographic
analysis, and that of 3 was determined by modified Mosher’s
method. Compound 1 exhibited lethality against brine
shrimp (Artemia salina) with an LD50 value of 4.8 μM and inhibitory activities against Staphyloccocus aureus, Aeromonas hydrophilia, Vibrio spp. V. harveyi and V. parahaemolyticus, and Gaeumannomyces graminis with minimum inhibitory concentration
values of 8, 8, 32, 8, and 16 μg/mL, respectively. Chlorination
at C-7 significantly increased the brine shrimp lethality and antimicrobial
activity of the bisthiodiketopiperazines.