Isolation and Difference in Anti-Staphylococcus aureus Bioactivity of Curvularin Derivates from Fungus Eupenicillium sp.

Abstract

With the anti-microbial and anti-tumor composite screening model, bioassay-guided fractionation led to the isolation of two structurally related bioactive compounds, curvularin and alphabeta-dehydrocurvularin, from ethyl acetate extract of Eupenicillium sp. associated with marine sponge Axinella sp. Further study on the structure-activity relationship demonstrated that both compounds exhibited differences in bioactive profiles which are highly associated with their minor structural differences. Both curvularin and alphabeta-dehydrocurvularin have similar level of anti-fungal and anti-tumorous activity, while alphabeta-dehydrocurvularin is active against Staphylococcus aureus with a minimal inhibitory concentration of 375 microg/ml but curvularin does not. No detectable activity against Gram-negative bacteria such as Escherichia coli and Pseudomonas aeruginosa exists for both compounds. It is suggested that the partial planar backbone structure, due to the conjugation of pi electrons in the presence of a 3,4-double bond and the carbonyl group at position C-2 in alphabeta-dehydrocurvularin, acts as a key factor for the inhibition of S. aureus, a Gram-positive low G + C bacteria that are often the hospital-acquired and/or community-acquired pathogen.

Phylogenetic diversity of culturable fungi associated with two marine sponges: Haliclona simulans and Gelliodes carnosa, collected from the Hainan Island coastal waters of the South China Sea

“…Further chemical investigations are needed to clarify the bioactive material basis. The marine environment is a rich source of both biological and chemical diversity (Raghukumar 2008;Raghukumar et al 2008;D'Souza-Ticlo et al 2009;Hochmuth and Piel 2009;Jones et al 2009b;Xie et al 2009). To date, almost all forms of life in the marine environment have been investigated (Bhadury et al 2006;Blunt et al 2009;Lang et al 2009), but the described species appear to represent only a fraction of the total number of species that have yet to be discovered.…”

Recent progress regarding the bioactivities, biosynthesis and synthesis of naturally occurring resorcinolic macrolides

“…Two DALs, curvularin (50) and 10,11-dehydrocurvularin (51), were reported to be produced by various genera of fungi including Curvularia sp [47,48] , Aspergillus aureofulgens [49] , Alternaria cinerariae [50] , C eragrostidis [51] , Penicillium sp [52] , Nectria galligena [53] , Eupenicillium sp [54] , and Chrysosporium lobatum [55] . Both compounds were found to have a variety of bioactivities.…”

Produtos naturais marinhos: isolamento e identificação de metabólitos inéditos a partir de fungos endofíticos e cianobactérias utilizando técnicas de eliciação química epigenética e desreplicação via redes moleculares

“…Preparação do material microbiológico, solventes, análises em CCDC, CLV, Para fermentação em meio líquido, foram utilizados os seguintes meios de cultivos: Curvularinas são macrolídeos ou policetídeos bastante ocorrentes em fungos, inclusive do gênero Penicillium (Xie et al, 2009). São compostos responsáveis por uma série de atividades biológicas, como por exemplo, antifúngico, citotóxico (Dai et al, 2010) e antibacteriano -contra S. aureus (Xie et al, 2009), dentre outras (Zhan, Gunatilaka, 2005).…”

“…São compostos responsáveis por uma série de atividades biológicas, como por exemplo, antifúngico, citotóxico (Dai et al, 2010) e antibacteriano -contra S. aureus (Xie et al, 2009), dentre outras (Zhan, Gunatilaka, 2005). Por esta razão, a síntese de seus derivados vem sendo frequentemente explorada na literatura (Dai et al, 2010), e tornaram-se estruturas quimicamente interessantes.…”

“…Ainda, estes metabólitos tem apresentado atividade citotóxica (Greve et al, 2008;Meng et al, 2013), antibacteriana (Xie et al, 2009;Dai et al, 2010), dentre outros (incluindo estudos de mecanismos de ação). Porém, quanto ao metabólito (10E, 15R)-deidrocurvularina, existem apenas duas referências, ambas sobre linhagens de Curvularia isoladas de algas marinas vermelhas (Greve et al, 2008;Dai et al, 2010), sendo que em um dos estudos, foi comprovada a ação antitumoral do metabólito, independente da estereoquímica do carbono-15 (Greve et al, 2008).…”