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

A previously unreported chromene derivative, 1-hydroxy-12-methoxycitromycin ( ), and four previously undescribed chromone derivatives, including pyanochromone ( ), spirofuranochromone ( ), 7-hydroxy-6-methoxy-4-oxo-3-[(1 )-3-oxobut-1-en-1-yl]-4 -chromene-5-carboxylic acid ( ), a pyranochromone dimer...

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Published inMarine drugs Vol. 16; no. 8; p. 289
Main Authors Kumla, Decha, Pereira, José A, Dethoup, Tida, Gales, Luis, Freitas-Silva, Joana, Costa, Paulo M, Lee, Michael, Silva, Artur M S, Sekeroglu, Nazim, Pinto, Madalena M M, Kijjoa, Anake
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 20.08.2018
MDPI
Subjects
Animals
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Antibacterial activity
Aquatic Organisms - chemistry
Aspergillaceae
Bacteria
Bacteria - drug effects
Carboxylic acids
chromone derivatives
Chromones - chemistry
Chromones - pharmacology
Derivatives
Dimers
Ergosterol
Fungi
Fungi - chemistry
GKK 1032B
Gram-negative bacteria
Gram-positive bacteria
Marine invertebrates
marine sponge-associated fungus
Methicillin
Microbiological strains
Multidrug resistance
Neopetrosia sp
Penicillium
Penicillium - chemistry
Penicillium erubescens
Porifera - chemistry
pyranochromone
spirofuranochromone
Staphylococcus aureus
antibacterial activity
spirofuranochromone
GKK 1032B
Aspergillaceae
Neopetrosia sp
marine sponge-associated fungus
Penicillium erubescens
pyranochromone
chromone derivatives
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Abstract A previously unreported chromene derivative, 1-hydroxy-12-methoxycitromycin ( ), and four previously undescribed chromone derivatives, including pyanochromone ( ), spirofuranochromone ( ), 7-hydroxy-6-methoxy-4-oxo-3-[(1 )-3-oxobut-1-en-1-yl]-4 -chromene-5-carboxylic acid ( ), a pyranochromone dimer ( ) were isolated, together with thirteen known compounds: β-sitostenone, ergosterol 5,8-endoperoxide, citromycin ( ), 12-methoxycitromycin ( ), myxotrichin D ( ), 12-methoxycitromycetin ( ), anhydrofulvic acid ( ), myxotrichin C ( ), penialidin D ( ), penialidin F ( ), SPF-3059-30 ( ), GKK1032B ( ) and secalonic acid A ( ), from cultures of the marine sponge- associated fungus KUFA0220. Compounds ⁻ , , , , ⁻ , were tested for their antibacterial activity against Gram-positive and Gram-negative reference and multidrug-resistant strains isolated from the environment. Only exhibited an in vitro growth inhibition of all Gram-positive bacteria whereas showed growth inhibition of methicillin-resistant (MRSA). None of the compounds were active against Gram-negative bacteria tested.
AbstractList 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.
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-[(1 E )-3-oxobut-1-en-1-yl]-4 H -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.
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.
A previously unreported chromene derivative, 1-hydroxy-12-methoxycitromycin ( ), and four previously undescribed chromone derivatives, including pyanochromone ( ), spirofuranochromone ( ), 7-hydroxy-6-methoxy-4-oxo-3-[(1 )-3-oxobut-1-en-1-yl]-4 -chromene-5-carboxylic acid ( ), a pyranochromone dimer ( ) were isolated, together with thirteen known compounds: β-sitostenone, ergosterol 5,8-endoperoxide, citromycin ( ), 12-methoxycitromycin ( ), myxotrichin D ( ), 12-methoxycitromycetin ( ), anhydrofulvic acid ( ), myxotrichin C ( ), penialidin D ( ), penialidin F ( ), SPF-3059-30 ( ), GKK1032B ( ) and secalonic acid A ( ), from cultures of the marine sponge- associated fungus KUFA0220. Compounds ⁻ , , , , ⁻ , were tested for their antibacterial activity against Gram-positive and Gram-negative reference and multidrug-resistant strains isolated from the environment. Only exhibited an in vitro growth inhibition of all Gram-positive bacteria whereas showed growth inhibition of methicillin-resistant (MRSA). None of the compounds were active against Gram-negative bacteria tested.
Author Dethoup, Tida
Sekeroglu, Nazim
Freitas-Silva, Joana
Pereira, José A
Gales, Luis
Kijjoa, Anake
Silva, Artur M S
Pinto, Madalena M M
Kumla, Decha
Lee, Michael
Costa, Paulo M
AuthorAffiliation 4 Instituto de Biologia Molecular e Celular (i3S-IBMC), Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
6 Departamento de Química & QOPNA, Universidade de Aveiro, 3810-193 Aveiro, Portugal; artur.silva@ua.pt
8 Laboratório de Química Orgânica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
5 Department of Chemistry, University of Leicester, University Road, Leicester LE 7 RH, UK; ml34@leicester.ac.uk
3 Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, Thailand; tdethoup@yahoo.com
2 Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Universidade do Porto, Terminal de Cruzeiros do Porto de Lexões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, Portugal
7 Department of Food Engineering, Faculty of Engineering and Architecture, Kilis 7 Aralık University, 79000 Kilis, Turkey; nsekeroglu@gmail.com
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/30127313$$D View this record in MEDLINE/PubMed
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2018 by the authors. 2018
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Issue 8
Keywords antibacterial activity
spirofuranochromone
GKK 1032B
Aspergillaceae
Neopetrosia sp
marine sponge-associated fungus
Penicillium erubescens
pyranochromone
chromone derivatives
Language English
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Snippet A previously unreported chromene derivative, 1-hydroxy-12-methoxycitromycin ( ), and four previously undescribed chromone derivatives, including pyanochromone...
A previously unreported chromene derivative, 1-hydroxy-12-methoxycitromycin (1c), and four previously undescribed chromone derivatives, including pyanochromone...
A previously unreported chromene derivative, 1-hydroxy-12-methoxycitromycin ( 1c ), and four previously undescribed chromone derivatives, including...
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StartPage 289
SubjectTerms Animals
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Antibacterial activity
Aquatic Organisms - chemistry
Aspergillaceae
Bacteria
Bacteria - drug effects
Carboxylic acids
chromone derivatives
Chromones - chemistry
Chromones - pharmacology
Derivatives
Dimers
Ergosterol
Fungi
Fungi - chemistry
GKK 1032B
Gram-negative bacteria
Gram-positive bacteria
Marine invertebrates
marine sponge-associated fungus
Methicillin
Microbiological strains
Multidrug resistance
Neopetrosia sp
Penicillium
Penicillium - chemistry
Penicillium erubescens
Porifera - chemistry
pyranochromone
spirofuranochromone
Staphylococcus aureus
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Title Chromone Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Penicillium erubescens KUFA0220 and Their Antibacterial Activity
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