New Bioactive β-Resorcylic Acid Derivatives from the Alga-Derived Fungus Penicillium antarcticum KMM 4685

被引：8

作者：

Leshchenko, Elena V. ^{[1
,2
]}

Antonov, Alexandr S. ^{[1
]}

Borkunov, Gleb V. ^{[1
,2
]}

Hauschild, Jessica ^{[3
,4
]}

Zhuravleva, Olesya I. ^{[1
,2
]}

Khudyakova, Yuliya V. ^{[1
]}

Menshov, Alexander S. ^{[1
]}

Popov, Roman S. ^{[1
]}

Kim, Natalya Yu ^{[1
]}

Graefen, Markus ^{[4
]}

Bokemeyer, Carsten ^{[3
]}

von Amsberg, Gunhild ^{[3
,4
]}

Yurchenko, Anton N. ^{[1
]}

Dyshlovoy, Sergey A. ^{[3
,4
]}

机构：

[1] Russian Acad Sci, GB Elyakov Pacific Inst Bioorgan Chem, Far Eastern Branch, 159 Prospect 100-letiya Vladivostoka, Vladivostok 690022, Russia

[2] Far Eastern Fed Univ, Inst High Technol & Adv Mat, Vladivostok 690922, Russia

[3] Univ Canc Ctr Hamburg UCCH, Univ Med Ctr Hamburg Eppendorf, Dept Oncol Hematol & Bone Marrow Transplantat Sect, Hubertus Wald Tumorzentrum, Martinistr 52, D-20246 Hamburg, Germany

[4] Univ Hosp Hamburg Eppendorf, Prostate Canc Ctr, Martini Klin, Martinistr 52, D-20246 Hamburg, Germany

来源：

MARINE DRUGS | 2023年 / 21卷 / 03期

基金：

俄罗斯科学基金会;

关键词：

marine-derived fungus; secondary metabolites; Penicillium antarcticum; p-glycoprotein inhibitory activity; prostate cancer; beta-resorcylic acid; ASPERGILLUS-FLAVUS; METABOLIC PRODUCTS; ASPERENTIN;

D O I：

10.3390/md21030178

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Five new beta-resorcylic acid derivatives, 14-hydroxyasperentin B (1), b-resoantarctines A-C (3, 5, 6) and 8-dehydro-b-resoantarctine A (4), together with known 14-hydroxyasperentin (5 '-hydroxyasperentin) (2), were isolated from the ethyl acetate extract of the fungus Penicillium antarcticum KMM 4685 associated with the brown alga Sargassum miyabei. The structures of the compounds were elucidated by spectroscopic analyses and modified Mosher's method, and the biogenetic pathways for compounds 3-6 were proposed. For the very first time, the relative configuration of the C-14 center of a known compound 2 was assigned via analyses of magnitudes of the vicinal coupling constants. The new metabolites 3-6 were biogenically related to resorcylic acid lactones (RALs); however, they did not possess lactonized macrolide elements in their structures. Compounds 3, 4 and 5 exhibited moderate cytotoxic activity in LNCaP, DU145 and 22Rv1 human prostate cancer cells. Moreover, these metabolites could inhibit the activity of p-glycoprotein at their noncytotoxic concentrations and consequently synergize with docetaxel in p-glycoprotein-overexpressing drug-resistant cancer cells.

引用

页数：17

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