Brominated Azaphilones from the Sponge-Associated Fungus Penicillium canescens Strain 4.14.6a

Marian Frank, Rudolf Hartmann, Malte Plenker, Attila Mándi, T. Kurtán, Ferhat Can Özkaya, Werner E.G. Müller, Matthias U. Kassack, Alexandra Hamacher, Wenhan Lin, Zhen Liu, Peter Proksch

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The fungus Penicillium canescens was isolated from the inner tissue of the Mediterranian sponge Agelas oroides. Fermentation of the fungus on solid rice medium yielded one new chlorinated diphenyl ether (1) and 13 known compounds (2-14). Addition of 5% NaBr to the rice medium increased the amounts of 4-6, while lowering the amounts of 8, 12, and 14. Furthermore, it induced the accumulation of 17 and two new brominated azaphilones, bromophilones A and B (15 and 16). Compounds 15 and 16 are the first example of azaphilones with the connection of a benzene moiety and the pyranoquinone core through a methylene group. The structures of the new compounds were elucidated based on the 1D and 2D NMR spectra as well as on HRESIMS data. The absolute configuration of the condensed bicyclic moiety of 15 and 16 was determined by sTDA ECD calculations. Compound 16 exhibited moderate cytotoxicity against the mouse lymphoma cell line L5178Y (IC50 8.9 μM), as well as against the human ovarian cancer cell line A2780 (IC50 2.7 μM), whereas the stereoisomer 15 was considerably less active.

Original languageEnglish
Pages (from-to)2159-2166
Number of pages8
JournalJournal of Natural Products
Volume82
Issue number8
DOIs
Publication statusPublished - Aug 23 2019

Fingerprint

Penicillium
Porifera
Fungi
Inhibitory Concentration 50
Agelas
Cells
Halogenated Diphenyl Ethers
Cell Line
Stereoisomerism
Cytotoxicity
Benzene
Ovarian Neoplasms
Fermentation
Lymphoma
Nuclear magnetic resonance
Tissue
Oryza
azaphilone

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Cite this

Brominated Azaphilones from the Sponge-Associated Fungus Penicillium canescens Strain 4.14.6a. / Frank, Marian; Hartmann, Rudolf; Plenker, Malte; Mándi, Attila; Kurtán, T.; Özkaya, Ferhat Can; Müller, Werner E.G.; Kassack, Matthias U.; Hamacher, Alexandra; Lin, Wenhan; Liu, Zhen; Proksch, Peter.

In: Journal of Natural Products, Vol. 82, No. 8, 23.08.2019, p. 2159-2166.

Research output: Contribution to journalArticle

Frank, M, Hartmann, R, Plenker, M, Mándi, A, Kurtán, T, Özkaya, FC, Müller, WEG, Kassack, MU, Hamacher, A, Lin, W, Liu, Z & Proksch, P 2019, 'Brominated Azaphilones from the Sponge-Associated Fungus Penicillium canescens Strain 4.14.6a', Journal of Natural Products, vol. 82, no. 8, pp. 2159-2166. https://doi.org/10.1021/acs.jnatprod.9b00151
Frank, Marian ; Hartmann, Rudolf ; Plenker, Malte ; Mándi, Attila ; Kurtán, T. ; Özkaya, Ferhat Can ; Müller, Werner E.G. ; Kassack, Matthias U. ; Hamacher, Alexandra ; Lin, Wenhan ; Liu, Zhen ; Proksch, Peter. / Brominated Azaphilones from the Sponge-Associated Fungus Penicillium canescens Strain 4.14.6a. In: Journal of Natural Products. 2019 ; Vol. 82, No. 8. pp. 2159-2166.
@article{01eeb038a3f14a92b9b18533c96ef2b9,
title = "Brominated Azaphilones from the Sponge-Associated Fungus Penicillium canescens Strain 4.14.6a",
abstract = "The fungus Penicillium canescens was isolated from the inner tissue of the Mediterranian sponge Agelas oroides. Fermentation of the fungus on solid rice medium yielded one new chlorinated diphenyl ether (1) and 13 known compounds (2-14). Addition of 5{\%} NaBr to the rice medium increased the amounts of 4-6, while lowering the amounts of 8, 12, and 14. Furthermore, it induced the accumulation of 17 and two new brominated azaphilones, bromophilones A and B (15 and 16). Compounds 15 and 16 are the first example of azaphilones with the connection of a benzene moiety and the pyranoquinone core through a methylene group. The structures of the new compounds were elucidated based on the 1D and 2D NMR spectra as well as on HRESIMS data. The absolute configuration of the condensed bicyclic moiety of 15 and 16 was determined by sTDA ECD calculations. Compound 16 exhibited moderate cytotoxicity against the mouse lymphoma cell line L5178Y (IC50 8.9 μM), as well as against the human ovarian cancer cell line A2780 (IC50 2.7 μM), whereas the stereoisomer 15 was considerably less active.",
author = "Marian Frank and Rudolf Hartmann and Malte Plenker and Attila M{\'a}ndi and T. Kurt{\'a}n and {\"O}zkaya, {Ferhat Can} and M{\"u}ller, {Werner E.G.} and Kassack, {Matthias U.} and Alexandra Hamacher and Wenhan Lin and Zhen Liu and Peter Proksch",
year = "2019",
month = "8",
day = "23",
doi = "10.1021/acs.jnatprod.9b00151",
language = "English",
volume = "82",
pages = "2159--2166",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "American Chemical Society",
number = "8",

}

TY - JOUR

T1 - Brominated Azaphilones from the Sponge-Associated Fungus Penicillium canescens Strain 4.14.6a

AU - Frank, Marian

AU - Hartmann, Rudolf

AU - Plenker, Malte

AU - Mándi, Attila

AU - Kurtán, T.

AU - Özkaya, Ferhat Can

AU - Müller, Werner E.G.

AU - Kassack, Matthias U.

AU - Hamacher, Alexandra

AU - Lin, Wenhan

AU - Liu, Zhen

AU - Proksch, Peter

PY - 2019/8/23

Y1 - 2019/8/23

N2 - The fungus Penicillium canescens was isolated from the inner tissue of the Mediterranian sponge Agelas oroides. Fermentation of the fungus on solid rice medium yielded one new chlorinated diphenyl ether (1) and 13 known compounds (2-14). Addition of 5% NaBr to the rice medium increased the amounts of 4-6, while lowering the amounts of 8, 12, and 14. Furthermore, it induced the accumulation of 17 and two new brominated azaphilones, bromophilones A and B (15 and 16). Compounds 15 and 16 are the first example of azaphilones with the connection of a benzene moiety and the pyranoquinone core through a methylene group. The structures of the new compounds were elucidated based on the 1D and 2D NMR spectra as well as on HRESIMS data. The absolute configuration of the condensed bicyclic moiety of 15 and 16 was determined by sTDA ECD calculations. Compound 16 exhibited moderate cytotoxicity against the mouse lymphoma cell line L5178Y (IC50 8.9 μM), as well as against the human ovarian cancer cell line A2780 (IC50 2.7 μM), whereas the stereoisomer 15 was considerably less active.

AB - The fungus Penicillium canescens was isolated from the inner tissue of the Mediterranian sponge Agelas oroides. Fermentation of the fungus on solid rice medium yielded one new chlorinated diphenyl ether (1) and 13 known compounds (2-14). Addition of 5% NaBr to the rice medium increased the amounts of 4-6, while lowering the amounts of 8, 12, and 14. Furthermore, it induced the accumulation of 17 and two new brominated azaphilones, bromophilones A and B (15 and 16). Compounds 15 and 16 are the first example of azaphilones with the connection of a benzene moiety and the pyranoquinone core through a methylene group. The structures of the new compounds were elucidated based on the 1D and 2D NMR spectra as well as on HRESIMS data. The absolute configuration of the condensed bicyclic moiety of 15 and 16 was determined by sTDA ECD calculations. Compound 16 exhibited moderate cytotoxicity against the mouse lymphoma cell line L5178Y (IC50 8.9 μM), as well as against the human ovarian cancer cell line A2780 (IC50 2.7 μM), whereas the stereoisomer 15 was considerably less active.

UR - http://www.scopus.com/inward/record.url?scp=85071712121&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85071712121&partnerID=8YFLogxK

U2 - 10.1021/acs.jnatprod.9b00151

DO - 10.1021/acs.jnatprod.9b00151

M3 - Article

C2 - 31359750

AN - SCOPUS:85071712121

VL - 82

SP - 2159

EP - 2166

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 8

ER -