α-Pyrone and decalin derivatives from the marine-derived fungus Trichoderma harzianum PSU-MF79

Abstract

Two new compounds, one α-pyrone (trichoharzianone) and one decalin (trichoharzianin), along with eight known compounds including three decalins, two δ-lactones, two carboxylic acids and one isochroman were isolated from the marine-derived fungus Trichoderma harzianum PSU-MF79. The structures were determined by spectroscopic methods. The relative configuration of trichoharzianin was assigned based on NOEDIFF data and coupling constants whereas the absolute configurations were established by comparison of electronic circular dichroism data with those of the co-metabolites. Known (-)-massoia lactone exhibited mild antifungal activity against Cryptococcus neoformans ATCC90113 flucytosine-resistant, Candida albicans ATCC90028 and C. albicans NCPF3153 with MIC values of 128, 200 and 200 µg/mL, respectively, and weak cytotoxic activity against HCT-116 and MCF-7 cell lines with the respective IC₅₀ values of 17 and 32 µM. In addition, it was noncytotoxic against noncancerous Vero cells with an IC₅₀ value of >100 µM.

Graphical Abstract

Keywords:

• Trichoderma harzianum
• marine-derived fungus
• α-pyrone
• decalin
• δ-lactone
• antifungal activity
• cytotoxic activity

Acknowledgments

V.R. thanks the NSTDA Chair Professor grant (the Fourth Grant) of the Crown Property Bureau and the National Science and Technology Development Agency. C.M. acknowledges the grant DBG6180029 from Thailand Research Fund (presently Thailand Science Research and Innovation) and National Research Council of Thailand. S.N. acknowledges the NSTDA Chair Professor grant for a scholarship 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 and Faculty of Science, Prince of Songkla University for partial support.

Disclosure statement

No potential conflict of interest was reported by the authors.

Funding

This work was supported by the NSTDA Chair Professor grant (the Fourth Grant) of the Crown Property Bureau, the grant DBG6180029 from Thailand Research Fund (presently Thailand Science Research and Innovation) and National Research Council of Thailand, and the Graduate School and Faculty of Science, Prince of Songkla University.

Figure 1. Structures of compounds 1-10 isolated from Trichoderma harzianum PSU-MF79.

Additional information

Funding

V.R. thanks the NSTDA Chair Professor grant (the Fourth Grant) of the Crown Property Bureau and the National Science and Technology Development Agency. C.M. acknowledges the grant DBG6180029 from Thailand Research Fund (presently Thailand Science Research and Innovation) and National Research Council of Thailand. S.N. acknowledges the NSTDA Chair Professor grant for a scholarship 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 and Faculty of Science, Prince of Songkla University for partial support.