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Chromone Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Penicillium erubescens KUFA0220 and Their Antibacterial Activity

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posted on 2018-10-10, 14:38 authored by Decha Kumla, José A. Pereira, Tida Dethoup, Luis Gales, Joana Freitas-Silva, Paulo M. Costa, Michael Lee, Artur M. Silva, Nazim Sekeroglu, Madalena M. M. Pinto, Anake Kijjoa
A previously unreported chromene derivative, 1-hydroxy-12-methoxycitromycin (1c), and four previously undescribed chromone derivatives, including pyanochromone (3b), spirofuranochromone (4), 7-hydroxy-6-methoxy-4-oxo-3-[(1E)-3-oxobut-1-en-1-yl]-4H-chromene-5-carboxylic acid (5), a pyranochromone dimer (6) were isolated, together with thirteen known compounds: β-sitostenone, ergosterol 5,8-endoperoxide, citromycin (1a), 12-methoxycitromycin (1b), myxotrichin D (1d), 12-methoxycitromycetin (1e), anhydrofulvic acid (2a), myxotrichin C (2b), penialidin D (2c), penialidin F (3a), SPF-3059-30 (7), GKK1032B (8) and secalonic acid A (9), from cultures of the marine sponge- associated fungus Penicillium erubescens KUFA0220. Compounds 1a–e, 2a, 3a, 4, 7–9, were tested for their antibacterial activity against Gram-positive and Gram-negative reference and multidrug-resistant strains isolated from the environment. Only 8 exhibited an in vitro growth inhibition of all Gram-positive bacteria whereas 9 showed growth inhibition of methicillin-resistant Staphyllococus aureus (MRSA). None of the compounds were active against Gram-negative bacteria tested.

Funding

: This work was partially supported through national funds provided by FCT/MCTESFoundation for Science and Technology from the Minister of Science, Technology and Higher Education (PIDDAC) and European Regional Development Fund (ERDF) through the COMPETE—Programa Operacional Factores de Competitividade (POFC) programme, under the project PTDC/MAR-BIO/4694/2014 (reference POCI-01-0145-FEDER-016790; Project 3599-Promover a Produção Científica e Desenvolvimento Tecnológico e a Constituição de Redes Temáticas (3599-PPCDT)) in the framework of the programme PT2020 as well as by the project INNOVMAR-Innovation and Sustainability in the Management and Exploitation of Marine Resources (reference NORTE-01-0145-FEDER-000035, within Research Line NOVELMAR), supported by North Portugal Regional Operational Programme (NORTE 2020), under the PORTUGAL 2020 Partnership Agreement, through the European Regional Development Fund (ERDF). Decha Kumla thanks the Alfabet Project of the Erasmus Mundus for a PhD’s scholarship

History

Citation

Marine Drugs 2018, 16(8), 289.

Version

  • VoR (Version of Record)

Published in

Marine Drugs 2018

Publisher

MDPI

issn

1660-3397

eissn

1660-3397

Acceptance date

2018-08-18

Copyright date

2018

Available date

2018-10-10

Publisher version

https://www.mdpi.com/1660-3397/16/8/289

Notes

The following are available online at http://www.mdpi.com/1660-3397/16/8/ 289/s1, Figure S1: Structures of β-sitosteanone and ergosterol-5,8-endoperoxide, isolated from the marine sponge-associated fungus Penicillium reubescens KUFA0220, Figures S2–S50 and S52–S53: 1D and 2D NMR spectra of isolated compounds, Figure S51: Ortep view of GKK1032B (8).

Language

en

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