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

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New Bioactive β-Resorcylic Acid Derivatives from the Alga-Derived Fungus Penicillium antarcticum KMM 4685. / Leshchenko, Elena V; Antonov, Alexandr S; Borkunov, Gleb V; Hauschild, Jessica; Zhuravleva, Olesya I; Khudyakova, Yuliya V; Menshov, Alexander S; Popov, Roman S; Kim, Natalya Yu; Graefen, Markus; Bokemeyer, Carsten; von Amsberg, Gunhild; Yurchenko, Anton N; Dyshlovoy, Sergey A.

In: MAR DRUGS, Vol. 21, No. 3, 178, 14.03.2023.

Research output: SCORING: Contribution to journal › SCORING: Journal article › Research › peer-review

Harvard

Leshchenko, EV, Antonov, AS, Borkunov, GV, Hauschild, J, Zhuravleva, OI, Khudyakova, YV, Menshov, AS, Popov, RS, Kim, NY, Graefen, M, Bokemeyer, C, von Amsberg, G, Yurchenko, AN & Dyshlovoy, SA 2023, 'New Bioactive β-Resorcylic Acid Derivatives from the Alga-Derived Fungus Penicillium antarcticum KMM 4685', MAR DRUGS, vol. 21, no. 3, 178. https://doi.org/10.3390/md21030178

APA

Leshchenko, E. V., Antonov, A. S., Borkunov, G. V., Hauschild, J., Zhuravleva, O. I., Khudyakova, Y. V., Menshov, A. S., Popov, R. S., Kim, N. Y., Graefen, M., Bokemeyer, C., von Amsberg, G., Yurchenko, A. N., & Dyshlovoy, S. A. (2023). New Bioactive β-Resorcylic Acid Derivatives from the Alga-Derived Fungus Penicillium antarcticum KMM 4685. MAR DRUGS, 21(3), [178]. https://doi.org/10.3390/md21030178

Vancouver

Leshchenko EV, Antonov AS, Borkunov GV, Hauschild J, Zhuravleva OI, Khudyakova YV et al. New Bioactive β-Resorcylic Acid Derivatives from the Alga-Derived Fungus Penicillium antarcticum KMM 4685. MAR DRUGS. 2023 Mar 14;21(3). 178. https://doi.org/10.3390/md21030178

Bibtex

@article{f0f5eaea90f646a2879e00fd7ab6f2b3,
title = "New Bioactive β-Resorcylic Acid Derivatives from the Alga-Derived Fungus Penicillium antarcticum KMM 4685",
abstract = "Five new β-resorcylic acid derivatives, 14-hydroxyasperentin B (1), β-resoantarctines A-C (3, 5, 6) and 8-dehydro-β-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.",
keywords = "Humans, Molecular Structure, Penicillium/chemistry, Fungi/chemistry",
author = "Leshchenko, {Elena V} and Antonov, {Alexandr S} and Borkunov, {Gleb V} and Jessica Hauschild and Zhuravleva, {Olesya I} and Khudyakova, {Yuliya V} and Menshov, {Alexander S} and Popov, {Roman S} and Kim, {Natalya Yu} and Markus Graefen and Carsten Bokemeyer and {von Amsberg}, Gunhild and Yurchenko, {Anton N} and Dyshlovoy, {Sergey A}",
year = "2023",
month = mar,
day = "14",
doi = "10.3390/md21030178",
language = "English",
volume = "21",
journal = "MAR DRUGS",
issn = "1660-3397",
publisher = "MDPI AG",
number = "3",

}

RIS

TY - JOUR

T1 - New Bioactive β-Resorcylic Acid Derivatives from the Alga-Derived Fungus Penicillium antarcticum KMM 4685

AU - Leshchenko, Elena V

AU - Antonov, Alexandr S

AU - Borkunov, Gleb V

AU - Hauschild, Jessica

AU - Zhuravleva, Olesya I

AU - Khudyakova, Yuliya V

AU - Menshov, Alexander S

AU - Popov, Roman S

AU - Kim, Natalya Yu

AU - Graefen, Markus

AU - Bokemeyer, Carsten

AU - von Amsberg, Gunhild

AU - Yurchenko, Anton N

AU - Dyshlovoy, Sergey A

PY - 2023/3/14

Y1 - 2023/3/14

N2 - Five new β-resorcylic acid derivatives, 14-hydroxyasperentin B (1), β-resoantarctines A-C (3, 5, 6) and 8-dehydro-β-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.

AB - Five new β-resorcylic acid derivatives, 14-hydroxyasperentin B (1), β-resoantarctines A-C (3, 5, 6) and 8-dehydro-β-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.

KW - Humans

KW - Molecular Structure

KW - Penicillium/chemistry

KW - Fungi/chemistry

U2 - 10.3390/md21030178

DO - 10.3390/md21030178

M3 - SCORING: Journal article

C2 - 36976227

VL - 21

JO - MAR DRUGS

JF - MAR DRUGS

SN - 1660-3397

IS - 3

M1 - 178

ER -