A nonadride derivative from the marine-derived fungus Aspergillus chevalieri PSU-AMF79

Abstract

One new nonadride enantiomer, ent-epiheveadride, along with five known dioxopiperazine derivatives were isolated from the marine-derived fungus Aspergillus chevalieri PSU-AMF79. Their structures were identified by extensive spectroscopic analysis. The absolute configuration of ent-epiheveadride was determined by comparison of the specific rotation and electronic circular dichroism data with those of related known compounds. It exhibited antifungal activity against Cryptococcus neoformans ATCC90113 flucytosine–resistant and Candida albicans NCPF3153 with the MIC values of 128 and 200 µg/mL, respectively. In addition, the known L-alanyl-L-tryptophan anhydride displayed TMEM16A inhibitory activity with 65.0% inhibition at a concentration of 5 µg/mL.

Graphical Abstract

Keywords:

• Aspergillus chevalieri
• marine-derived fungus
• nonadride
• dioxopiperazine
• enantiomer
• antimicrobial activity
• TMEM16A inhibitory activity

Acknowledgments

V. Rukachaisirikul thanks the NSTDA Chair Professor grant (the fourth Grant) of the Crown Property Bureau and the National Science and Technology Development Agency, Thailand. B. N. S. Ningsih acknowledges Thailand's Education Hub for the Southern Region of ASEAN Countries (TEH-AC) Scholarship from Prince of Songkla University (Contract No. TEH-AC 029/2018), and to the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Ministry of Higher Education, Science, Research and Innovation, Thailand and the Graduate School, Prince of Songkla University for partial support.

Disclosure statement

No potential conflict of interest was reported by the authors.

Correction Statement

This article has been corrected with minor changes. These changes do not impact the academic content of the article.

Additional information

Funding

This work was supported by the NSTDA Chair Professor grant (the Fourth Grant) of the Crown Property Bureau and National Science and Technology Development Agency and Thailand's Education Hub for ASEAN Countries (TEH-AC) scholarship (contract no. 029/2018).