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

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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 αβ-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 αβ-dehydrocurvularin have similar level of anti-fungal and anti-tumorous activity, while αβ-dehydrocurvularin is active against Staphylococcus aureus with a minimal inhibitory concentration of 375 μg/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 π electrons in the presence of a 3,4-double bond and the carbonyl group at position C-2 in αβ-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.

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Acknowledgements

This research was partially funded by the Knowledge Innovation Program of the Chinese Academy of Sciences (KZCX2-YW-216, KZCX2-YW-211) and National Supportive Plan Project of Science and Technology (2006BAB19B02). Parts of this study were carried out at the Key Laboratory of Microbial Application and Innovative Technology of Guangdong Province as an open funding project. We also thank the financial support of the Hundred Talents Program of Chinese Academy of Sciences. Many thanks to Dr. K. J. Lee for identification of the marine sponge, to Prof. Zanmin Hu and Prof. Honghui Zhu for providing some of the indicator organisms, and to Dr. Donna Smith for critical reading of this manuscript.

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Authors and Affiliations

  1. Key Laboratory of Marine Bio-resources Sustainable Utilization (LMB-CAS), Guangdong Key Laboratory of Marine Materia Medica (LMM-GD), South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, People’s Republic of China

    Lian Wu Xie, Yong Chang Ouyang, Guang Hua Wang, Min Jie Chen, Hui Min Sun, Shi Kun Dai & Xiang Li

  2. Central South University of Forestry & Technology, Changsha, 410004, People’s Republic of China

    Lian Wu Xie

  3. Medical Science College of China Three Gorges University, Yichang, 443002, People’s Republic of China

    Kun Zou

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  1. Lian Wu Xie
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Correspondence to Xiang Li.

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Lian Wu Xie and Yong Chang Ouyang contributed equally to this work.

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Xie, L.W., Ouyang, Y.C., Zou, K. et al. Isolation and Difference in Anti-Staphylococcus aureus Bioactivity of Curvularin Derivates from Fungus Eupenicillium sp.. Appl Biochem Biotechnol 159, 284–293 (2009). https://doi.org/10.1007/s12010-009-8591-2

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