Herqueilenone A, a unique rearranged benzoquinone-chromanone from the Hawaiian volcanic soil-associated fungal strain Penicillium herquei FT729.
Bioorg Chem
; 105: 104397, 2020 12.
Article
in En
| MEDLINE
| ID: mdl-33130348
ABSTRACT
The study of a Hawaiian volcanic soil-associated fungal strain Penicillium herquei FT729 led to the isolation of one unprecedented benzoquinone-chromanone, herqueilenone A (1) and two phenalenone derivatives (2 and 3). Their structures were determined through extensive analysis of NMR spectroscopic data and gauge-including atomic orbital (GIAO) NMR chemical shifts and ECD calculations. Herqueilenone A (1) contains a chroman-4-one core flanked by a tetrahydrofuran and a benzoquinone with an acetophenone moiety. Plausible pathways for the biosynthesis of 1-3 are proposed. Compounds 2 and 3 inhibited IDO1 activity with IC50 values of 14.38 and 13.69 µM, respectively. Compounds 2 and 3 also demonstrated a protective effect against acetaldehyde-induced damage in PC-12 cells.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Penicillium
/
Phenalenes
/
Enzyme Inhibitors
/
Indoleamine-Pyrrole 2,3,-Dioxygenase
Type of study:
Risk_factors_studies
Limits:
Animals
/
Humans
Language:
En
Journal:
Bioorg Chem
Year:
2020
Document type:
Article