Back to Search Start Over

New Zosteropenillines and Pallidopenillines from the Seagrass-Derived Fungus Penicillium yezoense KMM 4679

Authors :
Elena V. Leshchenko
Ekaterina A. Chingizova
Alexandr S. Antonov
Nadezhda P. Shlyk
Gleb V. Borkunov
Dmitrii V. Berdyshev
Viktoria E. Chausova
Natalya N. Kirichuk
Yuliya V. Khudyakova
Artur R. Chingizov
Anatoly I. Kalinovsky
Roman S. Popov
Natalya Yu. Kim
Ksenia A. Chadova
Ekaterina A. Yurchenko
Marina P. Isaeva
Anton N. Yurchenko
Source :
Marine Drugs, Vol 22, Iss 7, p 317 (2024)
Publication Year :
2024
Publisher :
MDPI AG, 2024.

Abstract

Ten new decalin polyketides, zosteropenilline M (1), 11-epi-8-hydroxyzosteropenilline M (2), zosteropenilline N (3), 8-hydroxyzosteropenilline G (4), zosteropenilline O (5), zosteropenilline P (6), zosteropenilline Q (7), 13-dehydroxypallidopenilline A (8), zosteropenilline R (9) and zosteropenilline S (10), together with known zosteropenillines G (11) and J (12), pallidopenilline A (13) and 1-acetylpallidopenilline A (14), were isolated from the ethyl acetate extract of the fungus Penicillium yezoense KMM 4679 associated with the seagrass Zostera marina. The structures of isolated compounds were established based on spectroscopic methods. The absolute configurations of zosteropenilline Q (7) and zosteropenilline S (10) were determined using a combination of the modified Mosher’s method and ROESY data. The absolute configurations of zosteropenilline M (1) and zosteropenilline N (3) were determined using time-dependent density functional theory (TD-DFT) calculations of the ECD spectra. A biogenetic pathway for compounds 1–14 is proposed. The antimicrobial, cytotoxic and cytoprotective activities of the isolated compounds were also studied. The significant cytoprotective effects of the new zosteropenilline M and zosteropenillines O and R were found in a cobalt chloride (II) mimic in in vitro hypoxia in HEK-293 cells. 1-Acetylpallidopenilline A (14) exhibited high inhibition of human breast cancer MCF-7 cell colony formation with IC50 of 0.66 µM and its anticancer effect was reduced when MCF-7 cells were pretreated with 4-hydroxitamoxifen. Thus, we propose 1-acetylpallidopenilline A as a new xenoestrogen with significant activity against breast cancer.

Details

Language :
English
ISSN :
16603397
Volume :
22
Issue :
7
Database :
Directory of Open Access Journals
Journal :
Marine Drugs
Publication Type :
Academic Journal
Accession number :
edsdoj.76c171564a844e2ca64f86268a70d6a6
Document Type :
article
Full Text :
https://doi.org/10.3390/md22070317