Structure-Guided Discovery of Diverse Cytotoxic Dimeric Xanthones/Chromanones from Penicillium chrysogenum C-7-2-1 and Their Interconversion Properties.
J Nat Prod
; 87(2): 238-251, 2024 02 23.
Article
in En
| MEDLINE
| ID: mdl-38354306
ABSTRACT
Xanthone-chromanone homo- or heterodimers are regarded as a novel class of topoisomerase (Topo) inhibitors; however, limited information about these compounds is currently available. Here, 14 new (1-14) and 6 known tetrahydroxanthone chromanone homo- and heterodimers (15-20) are reported as isolated from Penicillium chrysogenum C-7-2-1. Their structures and absolute configurations were unambiguously demonstrated by a combination of spectroscopic data, single-crystal X-ray diffraction, modified Mosher's method, and electronic circular dichroism analyses. Plausible biosynthetic pathways are proposed. For the first time, it was discovered that tetrahydroxanthones can convert to chromanones in water, whereas chromone dimerization does not show this property. Among them, compounds 5, 7, 8, and 16 exhibited significant cytotoxicity against H23 cell line with IC50 values of 6.9, 6.4, 3.9, and 2.6 µM, respectively.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Penicillium
/
Penicillium chrysogenum
/
Chromones
/
Xanthones
/
Antineoplastic Agents
Language:
En
Journal:
J Nat Prod
Year:
2024
Type:
Article