An anti-inflammatory isoflavone from soybean inoculated with a marine fungus Aspergillus terreus C23-3

Jing-Ming Yang; Ya-Yue Liu; Wen-Cong Yang; Xiao-Xiang Ma; Ying-Ying Nie; Evgenia Glukhov; Lena Gerwick; William H Gerwick; Xiao-Ling Lei; Yi Zhang

doi:10.1080/09168451.2020.1764838

An anti-inflammatory isoflavone from soybean inoculated with a marine fungus Aspergillus terreus C23-3

Biosci Biotechnol Biochem. 2020 Aug;84(8):1546-1553. doi: 10.1080/09168451.2020.1764838. Epub 2020 May 20.

Authors

Jing-Ming Yang^{1

2}, Ya-Yue Liu¹, Wen-Cong Yang¹, Xiao-Xiang Ma¹, Ying-Ying Nie², Evgenia Glukhov³, Lena Gerwick³, William H Gerwick³, Xiao-Ling Lei¹, Yi Zhang^{1

2

3}

Affiliations

¹ College of Food Science and Technology, Guangdong Provincial Key Laboratory of Aquatic Product Processing and Safety, Guangdong Province Engineering Laboratory for Marine Biological Products, Research Institute for Marine Drugs and Nutrition, Guangdong Ocean University , Zhanjiang, China.
² Marine Medicine Research and Development Center, Shenzhen Institute of Guangdong Ocean University , Shenzhen, China.
³ Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California , San Diego, CA, USA.

PMID: 32434451
DOI: 10.1080/09168451.2020.1764838

Abstract

A new isoflavone derivative compound 1 (psoralenone) was isolated from soybean inoculated with a marine fungus Aspergillus terreus C23-3, together with seven known compounds including isoflavones 2-6, butyrolactone I (7) and blumenol A (8). Their structures were elucidated by MS, NMR, and ECD. Psoralenone displayed moderate in vitro anti-inflammatory activity in the LPS-induced RAW264.7 cell model. Compound 2 (genistein) showed moderate acetylcholinesterase (AChE) inhibitory activity whereas compounds 2, 5 (biochanin A), 6 (psoralenol), and 7 exhibited potent larvicidal activity against brine shrimp. Compounds 3 (daidzein), 4 (4'-hydroxy-6,7-dimethoxyisoflavone), and 5-7 showed broad-spectrum anti-microbial activity, and compound 7 also showed moderate 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging activity.

Keywords: Aspergillus terreus; Soybean; anti-inflammation; isoflavone; marine fungus.

MeSH terms

4-Butyrolactone / analogs & derivatives
4-Butyrolactone / isolation & purification
4-Butyrolactone / pharmacology
Acetylcholinesterase
Animals
Anti-Infective Agents / isolation & purification
Anti-Infective Agents / pharmacology
Anti-Inflammatory Agents / isolation & purification*
Anti-Inflammatory Agents / pharmacology
Aspergillus / chemistry*
Aspergillus / physiology
Cholinesterase Inhibitors / isolation & purification
Cholinesterase Inhibitors / pharmacology
Cyclohexanones / isolation & purification
Cyclohexanones / pharmacology
Free Radical Scavengers / isolation & purification
Free Radical Scavengers / pharmacology
Furocoumarins / isolation & purification
Furocoumarins / pharmacology
Genistein / isolation & purification
Genistein / pharmacology
Glycine max / chemistry*
Glycine max / microbiology
Inflammation
Isoflavones / isolation & purification*
Isoflavones / pharmacology
Lipopolysaccharides / antagonists & inhibitors*
Lipopolysaccharides / pharmacology
Mice
RAW 264.7 Cells

Substances

Anti-Infective Agents
Anti-Inflammatory Agents
Cholinesterase Inhibitors
Cyclohexanones
Free Radical Scavengers
Furocoumarins
Isoflavones
Lipopolysaccharides
blumenol A
daidzein
butyrolactone I
Genistein
Acetylcholinesterase
4-Butyrolactone
biochanin A

Supplementary concepts

Aspergillus terreus