Herqueilenone A, a unique rearranged benzoquinone-chromanone from the Hawaiian volcanic soil-associated fungal strain Penicillium herquei FT729

Cited 19 time in scopus
Metadata Downloads
Title
Herqueilenone A, a unique rearranged benzoquinone-chromanone from the Hawaiian volcanic soil-associated fungal strain Penicillium herquei FT729
Author(s)
J S Yu; C Li; Mincheol Kwon; Taehoon Oh; T H Lee; D H Kim; Jong Seog AhnSung-Kyun Ko; C S Kim; S Cao; K H Kim
Bibliographic Citation
Bioorganic Chemistry, vol. 105, pp. 104397-104397
Publication Year
2020
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.
Keyword
Soil-associated fungusPenicillium herquei FT729Benzoquinone-chromanonePhenalenone derivativeIndoleamine 2,3-dioxygenase 1Acetaldehyde-induced damage
ISSN
0045-2068
Publisher
Elsevier
DOI
http://dx.doi.org/10.1016/j.bioorg.2020.104397
Type
Article
Appears in Collections:
Ochang Branch Institute > Chemical Biology Research Center > 1. Journal Articles
Files in This Item:
  • There are no files associated with this item.


Items in OpenAccess@KRIBB are protected by copyright, with all rights reserved, unless otherwise indicated.