Abstract

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.

Highlights

  • The fungi of the genus Penicillium (Family Aspergillaceae) are the most common fungi occurring in a diverse range of habitats from soil to vegetation to various food products, air, indoor environments, and marine environments

  • 19434, Enterococcus faecalis ATCC 29212, methicillin-resistant Staphylococcus aureus (MRSA) 66/1 isolated from public buses [28], and vancomycin-resistant enterococci (VRE) Enterococcus faecium 1/6/63 and Enterococcus faecalis B3/101 isolated from river water [29]

  • Polyketides are the major secondary metabolites isolated from marine-derived Penicillium species, other structural classes of secondary metabolites such as alkaloids, terpenoids, and sterols are isolated

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Summary

Introduction

The fungi of the genus Penicillium (Family Aspergillaceae) are the most common fungi occurring in a diverse range of habitats from soil to vegetation to various food products, air, indoor environments, and marine environments. They have a worldwide distribution and a large economic impact on human life [1]. In our ongoing search for antibiotics from marine-derived fungi from the tropical sea, we investigated secondary metabolites from cultures of Penicillium erubescens KUFA 0220, which was isolated from the marine sponge Neopetrosia sp., collected from the coral reef at Samaesan Island, Chonburi province, in the Gulf of Thailand.

Results and Discussion
The most stable
General Experimental Procedures
Fungal Material
Extraction and Isolation
X-ray Crystal Structure of 4
X-ray Crystal Structure of 5
Bacterial Strains and Growth Conditions
Antimicrobial Susceptibility Testing
Biofilm Formation Inhibition Assay
Antibiotic Synergy Testing
Conclusions
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