Peptides and polyketides isolated from the marine sponge-derived fungus Aspergillus terreus SCSIO 41008

Xiao-Wei Luo; Yun Lin; Yong-Jun Lu; Xue-Feng Zhou; Yong-Hong Liu

doi:10.1016/S1875-5364(19)30017-2

Peptides and polyketides isolated from the marine sponge-derived fungus Aspergillus terreus SCSIO 41008

Chin J Nat Med. 2019 Feb;17(2):149-154. doi: 10.1016/S1875-5364(19)30017-2.

Authors

Xiao-Wei Luo¹, Yun Lin², Yong-Jun Lu², Xue-Feng Zhou³, Yong-Hong Liu⁴

Affiliations

¹ CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China; University of Chinese Academy of Sciences, Beijing 100049, China.
² School of Life Sciences, Sun Yat-Sen University, Guangzhou 510275, China; Biomedical Center of Sun Yat-Sen University, Guangzhou 510275, China.
³ CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China; University of Chinese Academy of Sciences, Beijing 100049, China. Electronic address: xfzhou@scsio.ac.cn.
⁴ CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China; University of Chinese Academy of Sciences, Beijing 100049, China. Electronic address: yonghongliu@scsio.ac.cn.

PMID: 30797421
DOI: 10.1016/S1875-5364(19)30017-2

Abstract

Two new isomeric modified tripeptides, aspergillamides C and D (compounds 1 and 2), together with fifteen known compounds (compounds 3-17), were obtained from the marine sponge-derived fungus Aspergillus terreus SCSIO 41008. The structures of the new compounds, including absolute configurations, were determined by extensive analyses of spectroscopic data (NMR, MS, UV, and IR) and comparisons between the calculated and experimental electronic circular dichroism (ECD) spectra. Butyrolactone I (compound 11) exhibited strong inhibitory effects against Mycobacterium tuberculosis protein tyrosine phosphatase B (MptpB) with the IC₅₀ being 5.11 ± 0.53 μmol·L^-1, and acted as a noncompetitive inhibitor based on kinetic analysis.

Keywords: Aspergillamides; Aspergillus terreus; MptpB inhibitor; Polyketides.

MeSH terms

4-Butyrolactone / analogs & derivatives
4-Butyrolactone / chemistry
4-Butyrolactone / isolation & purification
4-Butyrolactone / pharmacology
Animals
Aspergillus / chemistry*
Chemistry Techniques, Analytical
Dipeptides / chemistry
Dipeptides / isolation & purification
Dipeptides / pharmacology
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / isolation & purification
Enzyme Inhibitors / pharmacology
Indoles / chemistry
Indoles / isolation & purification
Indoles / pharmacology
Molecular Structure
Mycobacterium tuberculosis / drug effects
Peptides / chemistry
Peptides / isolation & purification*
Peptides / pharmacology
Polyketides / chemistry
Polyketides / isolation & purification*
Polyketides / pharmacology
Porifera / microbiology*
Protein Tyrosine Phosphatases / chemistry

Substances

Dipeptides
Enzyme Inhibitors
Indoles
Peptides
Polyketides
aspergillamide
butyrolactone I
Protein Tyrosine Phosphatases
4-Butyrolactone