Structure-Guided Discovery of Diverse Cytotoxic Dimeric Xanthones/Chromanones from Penicillium chrysogenum C-7-2-1 and Their Interconversion Properties.

Autor: Guan J; State Key Laboratory Cultivation Base for TCM Quality and Efficacy, School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, People's Republic of China., Zhang PP; State Key Laboratory Cultivation Base for TCM Quality and Efficacy, School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, People's Republic of China., Wang XH; State Key Laboratory Cultivation Base for TCM Quality and Efficacy, School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, People's Republic of China., Guo YT; State Key Laboratory Cultivation Base for TCM Quality and Efficacy, School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, People's Republic of China., Zhang ZJ; State Key Laboratory Cultivation Base for TCM Quality and Efficacy, School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, People's Republic of China., Li P; State Key Laboratory Cultivation Base for TCM Quality and Efficacy, School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, People's Republic of China., Lin LP; State Key Laboratory Cultivation Base for TCM Quality and Efficacy, School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, People's Republic of China.
Jazyk: angličtina
Zdroj: Journal of natural products [J Nat Prod] 2024 Feb 23; Vol. 87 (2), pp. 238-251. Date of Electronic Publication: 2024 Feb 14.
DOI: 10.1021/acs.jnatprod.3c00907
Abstrakt: 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 IC 50 values of 6.9, 6.4, 3.9, and 2.6 μM, respectively.
Databáze: MEDLINE