Bioactive oxaphenalenone dimers from the fungus Talaromyces macrosporus KKU-1NK8

Boonyanoot Chaiyosang; Kwanjai Kanokmedhakul; Wareerat Sanmanoch; Sophon Boonlue; Sarinya Hadsadee; Siriporn Jungsuttiwong; Somdej Kanokmedhakul

doi:10.1016/j.fitote.2019.03.015

Bioactive oxaphenalenone dimers from the fungus Talaromyces macrosporus KKU-1NK8

Fitoterapia. 2019 Apr:134:429-434. doi: 10.1016/j.fitote.2019.03.015. Epub 2019 Mar 18.

Authors

Boonyanoot Chaiyosang¹, Kwanjai Kanokmedhakul¹, Wareerat Sanmanoch², Sophon Boonlue², Sarinya Hadsadee³, Siriporn Jungsuttiwong³, Somdej Kanokmedhakul⁴

Affiliations

¹ Natural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand.
² Department of Microbiology, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand.
³ Center for Organic Electronic and Alternative Energy, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Ubon Ratchathani University, Ubon Ratchathani 34190, Thailand.
⁴ Natural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand. Electronic address: somdej@kku.ac.th.

PMID: 30898727
DOI: 10.1016/j.fitote.2019.03.015

Abstract

Six new polyketide-derived oxaphenalenone dimers, talaromycesone C (1) and macrosporusones A-E (2-6), together with eight known analogs, were isolated from the mycelium of the fungus Talaromyces macrosporus KKU-1NK8. Their structures were established based on their spectroscopic data and MS. The absolute configurations of new compounds 1-6 were determined by ECD analyses. Compounds 3 and 8 exhibited antimalarial activity against Plasmodium falciparum. Compound 3 showed activity against NCI-H187 cells, while compound 8 displayed activity against KB, MCF-7 and NCI-H187 cell lines. In addition, compound 11 showed antibacterial activity against Bacillus cereus, Staphylococcus aureus and MRSA.

Keywords: Antibacterial; Cytotoxicity; Oxaphenalenone dimers; Talaromyces; Talaromyces macrosporus.

MeSH terms

Animals
Anti-Bacterial Agents / isolation & purification
Anti-Bacterial Agents / pharmacology*
Antimalarials / isolation & purification
Antimalarials / pharmacology*
Bacillus cereus / drug effects
Cell Line, Tumor
Chlorocebus aethiops
Forests
Humans
Molecular Structure
Plasmodium falciparum / drug effects
Soil Microbiology
Staphylococcus aureus / drug effects
Talaromyces / chemistry*
Thailand
Vero Cells

Substances

Anti-Bacterial Agents
Antimalarials