New phenyl derivatives from endophytic fungus Aspergillus flavipes AIL8 derived of mangrove plant Acanthus ilicifolius

Zhi-Qiang Bai; Xiuping Lin; Yizhu Wang; Junfeng Wang; Xuefeng Zhou; Bin Yang; Juan Liu; Xianwen Yang; Yi Wang; Yonghong Liu

doi:10.1016/j.fitote.2014.03.021

New phenyl derivatives from endophytic fungus Aspergillus flavipes AIL8 derived of mangrove plant Acanthus ilicifolius

Fitoterapia. 2014 Jun:95:194-202. doi: 10.1016/j.fitote.2014.03.021. Epub 2014 Apr 2.

Authors

Zhi-Qiang Bai¹, Xiuping Lin², Yizhu Wang³, Junfeng Wang², Xuefeng Zhou², Bin Yang², Juan Liu², Xianwen Yang², Yi Wang⁴, Yonghong Liu⁵

Affiliations

¹ CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China; Key Laboratory of Marine Materia Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China; Guangdong Institute of Microbiology, Guangzhou 510070, China.
² CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China; Key Laboratory of Marine Materia Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China.
³ Experimental Research Center, China Academy of Chinese Medical Sciences, Beijing 100700, China; Department of Genetics, School of Basic Medical Sciences, Jilin University, Changchun 130021, China.
⁴ Experimental Research Center, China Academy of Chinese Medical Sciences, Beijing 100700, China.
⁵ CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China; Key Laboratory of Marine Materia Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China. Electronic address: yonghongliu@scsio.ac.cn.

PMID: 24704337
DOI: 10.1016/j.fitote.2014.03.021

Abstract

Two new aromatic butyrolactones, flavipesins A (1) and B (2), two new natural products (3 and 4), and a known phenyl dioxolanone (5) were isolated from marine-derived endophytic fungus Aspergillus flavipes. The structures of compounds 1-5 were elucidated by 1D- and 2D-NMR and MS analysis, the absolute configurations were assigned by optical rotation and CD data, and the stereochemistry of 1 was determined by X-ray crystallography analysis. 1 demonstrated lower MIC values against Staphylococcus aureus (8.0 μg/mL) and Bacillus subtillis (0.25 μg/mL). 1 also showed the unique antibiofilm activity of penetration through the biofilm matrix and kills live bacteria inside mature S. aureus biofilm.

Keywords: Acanthus ilicifolius; Aspergillus flavipes; Butyrolactones; Endophytic fungus; Mangrove plant.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acanthaceae / microbiology*
Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / isolation & purification*
Anti-Bacterial Agents / pharmacology
Aspergillus / chemistry*
Aspergillus / physiology
Bacillus subtilis / drug effects
Bacillus subtilis / physiology
Biofilms / drug effects*
Biological Products / chemistry
Biological Products / isolation & purification
Biological Products / pharmacology
Biosynthetic Pathways
Cell Line, Tumor
Cell Proliferation / drug effects
Crystallography, X-Ray
Dioxolanes / chemistry
Dioxolanes / isolation & purification
Dioxolanes / pharmacology
Endophytes
Humans
Lactones / chemistry
Lactones / isolation & purification*
Lactones / pharmacology
Magnetic Resonance Spectroscopy
Microbial Sensitivity Tests
Molecular Structure
Staphylococcus aureus / drug effects
Staphylococcus aureus / physiology*

Substances

Anti-Bacterial Agents
Biological Products
Dioxolanes
Lactones